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Why Has Nobody Built a Truly Global STR Operator? Inside the Real Challenges of Scale with Forge Group, Casago, and MadeComfy

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Every major player in short-term rentals has chased the idea of building a truly global operator. None have cracked it.

In this panel, Simon Lehmann brings together three leaders shaping the next phase of professionalization: Graham Donoghue (Forge Group, UK), Steve Schwab (Casago, US), and Quirin Schwaighofer (MadeComfy, Australia). Together, they break down what it really takes to scale across borders and why local expertise still defines success.

This episode goes beyond theory. You’ll hear how operators balance growth with cultural nuance, how investors think about scale, and why the future of short-term rentals depends on blending technology with human judgment.

In this conversation, we discuss:

  • Why no operator has cracked the code for a global STR brand, and what makes each market uniquely difficult?
  • How Casago’s decentralized franchise model builds community-level trust while scaling across the Americas.
  • The MadeComfy playbook for partnering with real estate agents to grow fast and stay capital-light.
  • How Forge Group uses technology, AI, and long-term planning to drive operational excellence through 2030.
  • What private equity and strategic investors really measure when defining “value creation” in the STR sector.
  • Why the next generation of operators will need both AI-driven systems and human talent to stay competitive.

 Learn more about our guests:

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1Transcript

Introduction: [00:00:00] We have different ownership structures now within the three of you.

Introduction: [00:00:02] This maybe isn’t quite as good a deal as it used to be. The rules are changing.

Introduction: [00:00:07] The very first thing I did was get punched in the nose and realized that I wasn’t a local.

Introduction: [00:00:11] I was looked at the capital of Sunda, and I literally went in the cellar and cried.

Introduction: [00:00:17] I don’t want it to sound crude.

Introduction: [00:00:19] And ugly, but, um, as blunt as it sounds, it’s.

Introduction: [00:00:26] You’ve just given your secret sauce away that probably a lot of people around the world weren’t even aware of.

Introduction: [00:00:31] They think it’s just twice as hard. But I always say it’s quadratically more difficult.

Introduction: [00:00:34] I love thinking five years ahead. And then again, you get this call that puts you back into reality.

Introduction: [00:00:41] Box clever into this market. And in order to sort of survive, you know, bluntly.

Simon Lehmann: [00:00:46] Things are going fast and uh, and definitely more to come. You are listening to STR Global Unlocked, brought to you by AGL artillery, the show where I speak with the leaders shaping short term rentals worldwide. I am Simon Lehman, and after two decades buying, selling, advising and investing, I’ve built a network that spans continents and categories. This podcast brings that network to you. Real conversations, global insight. No PR fluff. Let’s get started. Today we’re recording a very special panel discussion. We brought together three incredible leaders from across the world of short term rentals, each of whom has built scale in very different but also difficult markets. Graham Donaghue, CEO of forge Group in the United Kingdom. Scotland at the moment, Steve Schwab, CEO of Kasargod in the US, which recently took over inventory from Vacasa United States. And last but not least, Quirin Schweighofer, co-founder and CEO of my Comfy in Australia, which have just recently been sold to Oyo. The big question will tackle today is why has nobody built a truly global SDR operator, and what the next five years might look like will cover a lot of ground today. So let’s get this started straight away. It’s fantastic to have you gentlemen, and I want to thank Steve for getting up very, very early in the morning.

Simon Lehmann: [00:02:25] And I want to thank Quirin for still being awake on a Friday night. And this shows to build an SDR global podcast has also its challenges with the different time zones. But these gentlemen made it happen. And I’m very thankful for that. And the kick off topic I want to bring up today is the elusive global brand forge. Sykes has become one of the largest operators in the UK, has been around for decades, and you’ve dipped into international expansion with an acquisition in New Zealand of a company called Bachcare. But apart from that, you sort of stay very true to the UK market and the roots of Sykes originally and have really focused your expansion, your market share, your professionalism, your brand and everything like that. In the UK market, you have a very strong direct distribution brand, and it’s interesting that you haven’t dipped your toes into other markets, and I would love to hear from you. Graham, what are your thoughts behind building a truly global property management company? Is that really necessary and what are the challenges behind that?

Graham Donoghue: [00:03:32] Well, what a question to start with. I mean, um, I think what I step back, I look at the facts, um, it’s deeply frustrating for me as someone running, you know, running our business, that we haven’t been able to expand internationally because you know what is true? It’s a big market. It’s global. There’s 20 odd million properties. It’s super fragmented. And ultimately what we’re all doing is taking people on holiday and making sure they have a really good time. You know, as you know, as I’ve looked at this many times and you’ve helped me, Simon, look at this many times. And every time I look at it, every time I look at it, I realize that on the surface, we all, all these markets look the same. But when you get under the skin of them, they’re all very, very different in terms of how to behave, how they operate, the consumer behaviors and the distribution, consumer acquisition, etc., etc.. Um, and I think one of the challenges I found is every time I’ve looked and I’ve tried to understand, can I create value and can I take all the lessons that I know about the business I run, which is pretty successful in the UK, and deploy that into other markets and create value. And the answer comes back, I’m not really sure. And we’ve tried it. As you mentioned on Bachcare, um, the idea of Bachcare was to deploy our technology and our capability to understand how could we add value? And we found it really hard. You know, we underestimated the difference in consumer behaviors. We underestimated the difference in the way that consumers look at distribution. You know, because the UK is predominantly a lot of them are direct distribution, you know, very reliant on sort of, you know, direct rebuke, whereas it’s much more fragmented and there’s much more choices in sort of in New Zealand.

Simon Lehmann: [00:05:17] Can I jump in here for a second? Because it’s an interesting one, because if you look at it from an outside, you can say there’s a lot of similarities with the exception of Time Zone, right? Same language. It’s an island. A lot of domestic demand, a lot of domestic supply, uh, sort of a lot of things that, for Sykes, are absolutely key. You know, all your customers come from the UK. Most of them your suppliers in the UK. You have one language and you build a lot of knowledge and marketing, um, experience and expertise. Is it really coming down to different consumer behaviour?

Graham Donoghue: [00:05:50] Yeah I think different consumer behaviour. You’re different, uh, desires, different needs. Different way that the owners use the properties. Um, you know, it’s much more ingrained in the culture, the idea of a batch. And in southern New Zealand, the the distribution was a big one for me. You know, the OTAs in particular were much more powerful, much more dominant in the way they behave and operate, um, which we really underestimated our ability to build a direct brand and to get high, rebook and invest in that digital marketing and that consumer brand to think, you know, requires a deeper purse than we really appreciate and realized. And just the way that the technology needs to behave as well. There’s ever so slightly different, you know, we couldn’t just easily lift and shift our technology and deploy it into one country. There was so many nuances that were market specific that we didn’t really appreciate and recognize at the time. So yeah, we found it pretty tough. And every time I’ve looked at other geographies, be that in Europe or be that in the US and in the US in particular. Obviously, I’ve looked at many times. Um, I thought, God, this is hard. Uh, there’s probably a good reason why it’s successful. But at the end of the month that that has then retrenched me back into the UK to say, um, can I get more headroom in the UK and can I go more, uh, horizontal in the way that I look at our product and move into more controlled distribution, other acquisitions and, and so far it’s sort of a, you know, there’s been enough headroom, but I do think someone will crack it. I do think generally someone will. But maybe it’s Steve, maybe it’s I don’t know. Um, it’s not high on our agenda at the moment, I have to say. Uh. Pretty hard.

Simon Lehmann: [00:07:35] Well, thank you for sharing that. It’s super interesting. It gives us a massive, massive segue. Um, also, you know, when we consult customers, they always want to expand in more destinations. And the first question I’m always asking them, how big is your Tam? And then stay where you are and get that to 10% market share or more. And then and then you can think about getting into new markets. If there’s no not enough supply of the quality that you’re looking for. So Steve, um, obviously categories international because you also are in Latin America joining the United States as well. But I want to focus a little bit more on Vacasa in this particular instance, because Vacasa has, uh, tried very hard to internationalize its business. So it’s risen and fallen its strategy, and now you’re trying to take over as much inventory as you possibly can into franchises and whatever. I think everybody is very familiar. What what you’re what you’re trying to do. What is your view on the internationalization and and what your next focus is and strategy with these combined inventories?

Steve Schwab: [00:08:35] Yeah. You know, when it comes to, uh, you know, going international and going to different markets that have completely different laws, labor laws, uh, you would have different, uh, you know, uh, property laws, Cause, uh, it seems a pretty big challenge to be able to run it from a central ops. And one of the, uh, you know, one of the solves that we have with the business model with Chicago is finding people who are, you know, on the ground and understand, you know, the culture of the local community, understand the labor laws, understands, you know, the regulatory issues that are going on and just being able to operate, uh, even just within the culture of, of the labor force. And we saw that a lot in, in, you know, vacasa where just not understanding the, the local business, especially internationally, was, uh, one of the biggest challenges there. And I think when we look at Casa and what we’re trying to do, um, you know, breaking this down into a decentralized franchise model, um, you know, we’re trying to solve for it by finding those people who are hyper local and can deal with the local issues, Use, uh, you know, block by block. Um, and I think that’s really where the, the differences between the two different business models.

Simon Lehmann: [00:09:54] So would you would that imply that, uh, Steve, that your main strategy is definitely domestic market us and and joining Latin American market for now.

Steve Schwab: [00:10:04] For now. Yeah. For now, you know, we’re we’re in the, uh, you know, us, Canada, the Caribbean and Latin America, uh, focusing on what we have right now is, uh, importance. You know, we’re going through this entire transformation of taking a very centralized model and decentralizing it, you know, and breaking it down to where we’re finding people who truly love their communities, aren’t using the communities and, uh, building the reputation, you know, you know, one community at a time and that’s, that’s that’s going to be our that’s going to be our focus for a while.

Simon Lehmann: [00:10:39] Well, definitely a topic we could fill an entire panel decentralizing versus decentralization. We’ve seen plenty of trials and errors out there as well to to make that happen. Also with European players, how much power they give to the local PMCs versus centralizing. And I want to with that move on to a query out of Australia. I, I’m obviously being fortunate enough to serve as a chairman for a while for made comfy, uh, because some distinct reasons, one of which I’m a huge Australia fan, but everybody can see that anyway. And and second and second, I found the business model very interesting. And I think it’s no big secret. Uh, when you started as a, as a, as a startup in United in Australia, starting with building your business and then thinking about expansion, uh, and then also truly being international. I think that was one of the challenges as well, when raising capital where the Australian market or local investment market is more challenging, to raise capital if it’s not truly international. So it was a chicken and egg for you guys as well. But let’s allude a little bit on, on my comfy and, and then obviously, uh, where were you thought, uh, before the transaction happened with, uh, in terms of internationalization and what you can do with your business?

Quirin Schwaighofer: [00:11:56] I think for, for us, Australia is a country where it’s a continent. So there are so many different different markets and pockets. So when we started in Sydney about ten, ten years ago, we had this big vision. We built a global, um, short term rental brand, uh, B2C. And the markets will be very similar to, to Sydney. We thought that about Melbourne. We thought about Brisbane and uh, sort of Central Coast. But we quickly realized that even in Australia, if you, for example, you come from New South Wales and you, you launch in Queensland, it’s pretty much like a different country. Um, a bit what, what Graham. So I’ve talked about before, um, so when we were managing property owners directly, we, we, we realized that it is tricky. Um, so how do you acquire, how do you keep, how do you build local operations and all of this? And how do you replicate that in every sort of location where you really can’t drive? You could fly everywhere and different time zones and sort of during Covid, um, the whole thing we were thinking about, how do we scale with little capital, um, and how do we get access to, to properties? We played a little bit with, with the franchise idea. Um, but what is a bit unique, maybe in Australia is that 76% of properties are in general managed by, um, real estate agents, property managers, um, Australians love to invest in property.

Quirin Schwaighofer: [00:13:24] Um, investment properties turn around every 7 to 10 years. So, um, if you write a little bit, um, you get in front of every single property if you are an agent. Um, and what we were wondering is like, why are they not doing short term rentals? Vacation rentals? Some do, but really, um, not many. And we were competing with some. We were trying to partner with a few. But what we identified is that opportunity to have that hyperlocal approach by enabling and partnering with real estate agents powered by McAfee, and they have a local community. They’re there, they’re in the footy club, and they’re selling those properties, and they are appraising long term rentals or. Yeah. Now also short term rentals. And that’s what we changed. That’s when I think also we met Simon. And I remember when I think we were driving to a meeting somewhere in Switzerland, and I sort of shared this idea with you, and it was a bit of a moment like, oh, that works out. That would be, uh, interesting. Um, and yeah, four years later, now you have 70% of our inventory is managed by real estate agents, and we mainly grow with that. So we’re solving the problems of our real estate agents. They acquire the properties. And with that we’re able to launch quite capital light. And in markets like Australia and New Zealand.

Simon Lehmann: [00:14:46] You’ve just given your secret sauce away that probably a lot of people around the world weren’t even aware of, but it had to happen at one stage. And obviously internationalisation is becoming pretty obvious that any Anglo-Saxon market where the real estate markets have similar dynamics, like the US and UK and Ireland and New Zealand, and you already have an office in New Zealand. So that’s going to be interesting. And we’ll talk about scale in a minute as well. But I guess we can allude that for Oyo this was also an internationalisation acquisition right.

Quirin Schwaighofer: [00:15:18] Yeah I mean I’ve given the secret sauce away. The secret sauce is not that. The secret sauce is how do you actually connect with agents and enable them to be successful. So it’s super complex. You’re adding another layer of stakeholders in an already very complex value chain between OTAs, guests, OTAs, property manager, property owner and now you’re adding an agent that needs to know everything about the property because they are managing the property owner. So yeah, I’m highly complex, but I think it’s sort of for Oyo, it’s Oyo, Oyo sort of. Um, I remember when I read that they acquired um, uh, Villa, uh, in, in Europe and then in 2019, I was like, oh, wow, they’re entering the short term rental space now. And I’ve been following them since and, and yeah, I think for, for you, um, of course, I wanted to enter Australia and New Zealand, but um, our business model being unique and applicable, um, within Oyo’s network was definitely also one reason that we were talking, uh, started talking last year.

Simon Lehmann: [00:16:22] Excellent. Interesting news all the way today. We heard that Interhome has now been finally fully taken over by Hometogo. So interesting times. Management changes have already been announced. Uh, things are going fast and, uh, and definitely more to come back to, Steve. I want to move on to scale an investment appetite. Right. So, you know, from a US perspective, what level of scale do you think you really need in order to go to the next level in terms of investment and growing the business forward? And what is scale for you and what you’re focusing on in creating value?

Steve Schwab: [00:17:01] Yeah. You know, I think that’s we’re sort of doing the the opposite of a normal scale where, you know, we’re going global, but local, local, if you want to call it that. The local, um, the, the investment appetite is certainly out there. We’re seeing it. There’s a lot of interest at a, at a pretty large levels of, you know, trying to come in and see what we’re doing. You’re seeing that across the entire United States right now. There’s a ton of activity happening. Um, you know, for us, uh, you know, seeing that, uh, that institutional money coming in and looking to play um, is certainly a big part of of the dynamics going forward. Uh, it’s just important to remember that, you know, as you look at what’s different between, uh, vacation rentals and hotels and airlines is unlike the hotels or airlines where you have a homogenized, you know, seat or, or room, um, in which the company, you know, actually owns it. We don’t own the market, and we have a lot of, uh, a very local culture that happens with the homeowners. I always talk about when I first got started here in Puerto Penasco and went to my first city, I thought I was pretty smart.

Steve Schwab: [00:18:14] I was just going to rubber stamp this thing. The very first thing I did was get punched in the nose and realized that I wasn’t a local, you know, in San Carlos as opposed to Porto Penasco, and learned pretty quickly. I wasn’t as smart as I thought I was because the homeowners there, it’s not just the travelers, it’s not just the the behaviors of those who are booking. It’s also, uh, homeowners who have a very different expectation in one city compared to another, and even having the same owner in multiple markets, they’ll have an expectation of how you operate their properties in different cities. So, um, really looking to mix that, uh, when you go when you think about going to scale, how are you going to take that scale and keep it local? Uh, because at the end of the day, every property is so unique and every market is so hyper localized. Uh, until you’re on the ground operating it, it’s just really difficult to bring that investment level to local markets.

Simon Lehmann: [00:19:12] Yeah, that’s super interesting. Uh, scaling while trying to be local, uh, is definitely a massive challenge. And, and definitely going to be interesting as you onboard more properties at from a casa as well within your within your system. We’ll talk about the business model. Uh, in a short while moving that to Graham. Graham uh, Forge Forge Group, Sykes is owned by a large cap private equity company. So you could probably talk to us about KPIs and scale for the next half hour. But still, I’d be super interested. I mean, we have different ownership structures now within the three of you. Uh, one owned by strategic, uh, another also by an investment group, a new, uh, by a really traditional large cap, private equity. Uh, you probably get grilled most in relation to scale and KPIs. What can you share in terms of your, you know, what is measured or what counts? Also from an investment perspective, it’s you know, we talk a lot on, on uh, on the day to day conversations about units, revenue, ADR, occupancy, RevPAR, this type of stuff. But I think you have taken this, uh, totally to the next level.

Graham Donoghue: [00:20:23] Yeah. I mean, we have a lot of data, we have a lot of KPIs, etc., that we we tend to think more around value creation, you know, and I think being owned obviously private equity owned, as you mentioned. You know, I think you spend a lot of time thinking about where’s the value going to come from knowing that you’re on a journey and could be five years time, could be ten years time, but eventually there’ll be a transaction that happens. And so you have to try and work your way back from that. So we spent a lot of time. So at the moment we’re 2025. Most of my thinking is in 2030. And so when I’m talking to, you know, my executive team and I’m talking to the.

Simon Lehmann: [00:21:01] 2030, did you say.

Graham Donoghue: [00:21:03] Yeah yeah, yeah. So most of my thinking is like what does the business look like in 2030? You know, whether I’m there or not in 2030 is irrelevant because it’s more around, like, you know, we need to create a legacy for this business. We need to understand what the value creation looks like. And, and there’ll be a set of numbers that drive that, and there’ll be there’ll be things that fuel that likely to be stock count, but also maybe around, you know, your revenue, your income, your customer acquisition. At the moment, we’re obsessing quite a lot around, um, operational efficiency, operational gearing and actually leveraging AI in particular. As you know, I’m a sort of a fan of AI in terms of how we use it in the business and trying to crystal ball gaze. How do I believe owners and consumers and our employees will be using tools and technology in the future, in 2030, and how do we sort of lean into that and think about a more authentic way of designing and developing our business? So I have to have people in my business that are, you know, I think in these three horizons, horizon one, two and three, I’ve got, you know, day to day operational people looking at horizon one, which is like the next 12 months trading, and then have a group of people looking at horizon two, which is like, you know, maybe in two years time, you know, beyond that. And then I have to have enough people looking at horizon three, which is 2030 and working our way back. And then we started thinking about like, how do we scale? What’s the The technology was the investment. What do you think that will do to revenue? What do you think will do to EBITDA? What’s the story we want to tell which is critically important? Um, and then how do we execute against it? And that’s a you know, that’s how we play into it.

Simon Lehmann: [00:22:46] Super interesting. So when I asked you about, you know, in relation to scale your, your core, the answer was we want to create value. And how do you break that down and how do you measure that with where you want to go with the business?

Graham Donoghue: [00:23:03] Well, I don’t want it to sound crude and ugly. Um, but but um, as blunt as it sounds, it’s around the, uh, equity value we think we’ll create in the business. And now you can create equity value in a business multiple different ways. You can, um, um, have a very high multiple of your earnings, or you can have high earnings with a lower sort of multiple and then everything in between. Um, and who knows because the markets ebb and flow. We’re probably in a bit of a depressed there are at the moment where, you know, values are not as high as they were and debt is difficult, it’s expensive, etc., etc. but we tend to work on, um, you know, what do we need to look like in the future? How do we think that equity value will be derived? What are the levers we’re going to pull to create that? And then we work our way back. And generally you need things like supply. You need things like margin expansion. You need to know how you’re going to convert. You need to know how many customers you’re going to have, how many property owners you’re going to have, how your revenue is going to flow.

Graham Donoghue: [00:24:13] You know, your occupancy, your ADR, all that sort of stuff. And we model all of that. Um, and we get it wrong all the time. And, but we have to start with a model and work our way back, um, and then say, okay, then how do we get there? And then that it normally comes to a point where you say what investment do we require to get there as well. And then that requires another conversation around do we have to refi the business or do we have to go and find additional investors. You know, do we need to, you know, are we planning to make a big acquisition because we can’t get there? So that’s generally how we we model that, how we sort of begin with the end in mind and we work our way back. But we make we make sure we have enough people looking at those three horizons to understand what the story, what the story sort of look like and, and how it plays into value.

Simon Lehmann: [00:25:04] Fantastic. Well, I’m glad I did a little bit more digging there. And, uh, you know, at the end of the day, we need to think about our markets and our ownerships and maximizing value has, uh, different, different, uh, different levels as well. Um, bringing that back to querying and probably get a little bit more concrete in terms of your recent transaction with selling a business to a strategic buyer, you know, and, and and talk a little bit about this process, what what was sort of what was the key drivers in relation to scaling your business? For any strategic investor looking at your business in relation to unit economics, growth and things like that, and specifically your, your, um, your buyer that has acquired you. But what I mean, make comfy was always a company that was already extremely well call it documented. Your management information system was well above average. From what I have seen in many property management companies of your size. But what was the key that they were looking at in terms of scale and driving value for the acquisition?

Quirin Schwaighofer: [00:26:12] I think we we both started the business with um, um, setting it up for, for, for scale. And we always talked about, um, 2030. I think we for a long time. And that was the main thing. Um, where do we head to? And let’s build the business according to that? Um, we’ve been audited after a year three, and we’ve been, um, we’ve been we’ve run a board, um, also after year three already. So we, we, um, got involved and first to advise us and then being, um, as I would say on our board. So we, we always had this kind of vision to, to set the business up and to be run professionally. Um, on the other side, uh, our big business model being B to B to C is all about serving customers, making short term rentals, professional, um, helping housekeeping partners who are in a professional business, helping our traders to be, um, more structured and more organized. Um, our real estate partners. Um, um, what I didn’t really think at the beginning, but there’s a lot we can help them. So there’s a lot of, um, there’s professionalism and structure that we require and has been something we always had. Now we were not looking at and we were not looking at selling the business.

Quirin Schwaighofer: [00:27:31] We had our plan to keep growing in Australia, and we were preparing for some international markets and did quite an analysis there where we think that our business model could work as well. Our platform is already international. We do multiple time zones, multiple currencies. We operate in New Zealand as well. So that was our plan and we have been approached by three US three strategic buyers last year, which was interesting. And the first two, it was a very easy now, very easy now. And we were really not and like, you know me, we were not looking to be to be bought. Um, it was only really when, um, when I met Shirish and then Ritesh that I for the first time thought They think very similar to to me. Super quick, super sharp. Down to the detail. Passion for the supply side, but also for the operational side and significantly bigger. Like like executional excellence than. And we got to in a very similar time frame. Um, and yeah, it um on our side we were we, we, I’d say in a much smaller scale, but we were able to answer questions really quickly around certain metrics and like of course, down to, um, sellable home nights and, and, uh, by market by, um, uh, sort of the evolution of RFP by year.

Quirin Schwaighofer: [00:29:07] Does your stock go down or go up in the RFP over years? So all of that, we were able to provide, um, overnight, pretty much. And I think that was quite impressive. Um, and then going to the to those, those sort of business model, and the flask, because we really did not have much access to capital. When I looked at the capital raises of Sonda and Vacasa, I literally went in the cellar and cried for like just a 10th of that. We could do so much with this. Um. And we yeah, we raised we still raised close to 20 million over a year, but we really didn’t have this one lump where we said, okay, now let’s focus, do something with that. And so we were we had to look after every dollar all the time. So the business model that we developed was pretty much, um, a evolution of our strategic thinking, growing big and being structured. And then, yeah, looking after every penny and, uh, ensuring that we’re not spending this on supply acquisition especially or demand acquisition.

Simon Lehmann: [00:30:06] Super interesting. Um, and you gave me a beautiful segue to talk about business model. I’ve had a lot of recent conversations with different executives in this industry and seeing some moves, uh, where, you know, we somebody tried to build a large United States company as a SaaS business, but we didn’t know what the abbreviation meant. Is it software as a service or service as a software? Right. And and a lot of things have been learned along the way in terms of and we had super interesting conversations this year with Ashley Graham and Steve, uh, to talk about, you know, proprietary technology, helping you to, um, to differentiate yourself or you going with off the shelf software. And we see a lot of movements in this space. But I want to talk about more the core business model right now. And I want to start with Graham on that. I mean, obviously Sykes is definitely more an exclusive distribution business than it is an operating business. And but that’s also come historically where homeowners in the UK live closer to the properties. They manage it themselves. But you do the distribution. But I would love to hear your general view you and how you viewed, or how you’re viewing all the different business models that are out there from an end to end, full service property management service that more like a Query and Steve are providing to their owners and their guests. And you are clearly differentiated, and maybe New Zealand is maybe more a full service business as well. But what is sort of your view, Graham, on the different business models out there and how you foresee the future and how is that going to be evolving?

Graham Donoghue: [00:31:49] Well, it’s been interesting the last 12 months because, um, so I’ve been doing this job for almost ten years and for at least maybe eight of those years, the thing that used to worry about constantly was supply. And I used to always say, I have more demand than I need now it’s about about supply, supply, supply, supply. That’s what I need. But in the last 24 months, I’m not 100% sure why, which is scary. It seems to have flipped a little bit. Demand actually has become more of a challenge and supply seems to be, like, rolling in. Uh, weirdly. Um, I have a hypothesis, um, which again, I don’t have a huge amount of data. I’ve got some data, and I can only really speak about the UK market in particular. But when we look at the market, we think of the market in sort of a three core segments, like property managers and professionally run, um, you know, there’s three big ones in the UK and then there’s a lost trail, to be honest with you. You know, those three big ones have acquired most of them. Um, you know, and we’ve read a lot of that over the years. You then obviously have um, uh, homes in the UK that haven’t been rented out but are second homes. And there’s, you know, a lot of them, hundreds of thousands of them, maybe 150,000 of them. Wow. And then you have homes in the UK that we call the RBL market oriented by Owner Direct, which, which, you know.

Simon Lehmann: [00:33:14] Which is that about half of the supply.

Graham Donoghue: [00:33:16] Okay, well, we think it’s about another 100, 130,000 roughly. So, you know, you know, so market size in the UK, half a million properties. And what have we got on the agency business. 2024 25,000 properties. So you step back and you think well supply shouldn’t be an issue. But I think what I’m seeing is as regulation has increased in the UK and the cost of living, of operating and running a second home has gone up significantly in the UK. And now seeing more of those second homes that are not rented out, those owners are now choosing to say, well, maybe we should rent it out, maybe we should try to generate some income and that and that’s bringing in, you know, more supply into our into our sort of a market. And then more recently, I would say in the last maybe ten months, I’m seeing the Rbo market. And so people who used to rent, particularly with Airbnb less so Booking.com particularly Airbnb. Um, moving to saying, well, do you know what? This maybe isn’t quite as good a deal as it used to be. The rules are changing. They’re changing the way that they’re treating hosts. Um, and actually, for not a lot more commission. I can have someone who just takes away all the pain and, you know, does everything that you know, that that that I’m sort of spending all my waking hours to do. Now, there is a segment of people that clearly love that interaction, but there’s a segment of people who don’t.

Graham Donoghue: [00:34:46] And so is that a different business model? I don’t entirely know. Um, but, you know, we’re now sitting here saying, actually supply is, is, is is doing incredibly well and demand is becoming more of the challenge. And that has then forced us as an organization to say, I can’t really sit on a business that’s 80% direct anymore. Um, because it’s getting too hard to find. What I need to then do is to utilize some of the other distribution channels that exist, particularly for OTAs, and recognize there’s just a different cohort of customers out there, of course, utilizing those channels and lean into them, particularly for international guests, which they can do a lot better. But more recently, what I’m seeing is for guests that want like real last minute and minimum stay of, say, one night, which is something we would never have considered of doing 12 months ago. But now, you know, by opening up our portfolio. So I think the world is getting really confusing, you know, in terms of what the business models is. And I’m not speaking about franchise here or various different things. I’m talking more just around how we look at them and how we have to trade our way and box clever into this market and in order to sort of survive, you know, bluntly super interesting.

Simon Lehmann: [00:36:05] So I find that very interesting. And there’s so many Segways here. Uh, also about, you know, the one night and now, especially since Airbnb announced the rate hike and the split with that’s going to have a massive impact. I’ve just written a newspaper article in Switzerland about that today. Actually, I was asked to comment. And what does that really mean for the consumer? And and I’ve just came back from a consulting mandate this week, three days in the mountains. And, you know, they deal with the one day stay with fortnight price in the high season. And it and it works. It works fantastically. So it’s interesting how we are forced in a way to operate smarter because we need to always question to tradition to be better and, and and be ahead of the game. And but I hear from you, Graham, you’re not hiring an armada of cleaners and get into the service business.

Graham Donoghue: [00:36:58] No, sorry. And yes, I mean, we’re still we’re still of of the you know, we do a million bookings a year roughly in the UK and of those million bookings a year, but 150,000 of those bookings. We facilitate the cleaning and management. Everything else is done either by a third party or by the owner themselves. However, every single one of them we monitor and we facilitate and through our software. So there’s quite a high degree of rigor around the feedback, the net promoter score. Sure, the the cleaning score and all that sort of stuff. So, you know, although we don’t have direct control, we monitor because ultimately it’s about delivering a good guest experience and helping owners, um, you know, improve their service because they just, you know, they don’t always know. Of course.

Simon Lehmann: [00:37:50] Excellent. So we have a bit of a different case, uh, across the pond. Uh, Steve. Well, I mean, looking at how you build and where you came from, what you thought, what sort of a hybrid, if we call it. But you can explain that a little bit better. And then going after a hard core, full service PMC that has had challenge to have good enough unit densities to operate profitably across all the different markets and other things. What does that mean and how you look at the business model going forward? Are you are you looking at entirely franchising it? How do you look at the service business?

Steve Schwab: [00:38:27] Yeah. So we’re uh, yeah, we’re we’re selling off every bit of it. We’re going completely to the franchise model, uh, a big believer in it. You know, when you think of, uh, uh, the different business models, I’m not sure there’s necessarily one. Right. Business model. I think what Graham is doing is working there. And if I tried to take my business model and transpose it where he’s at, you know, there’s a there’s a high probability of failure, uh, you know, making sure that you understand exactly, uh, what’s happening at the at, you know, at the part of the world that you’re working at is going to be the key to success here. Uh, we’re seeing this as the truth is, you can’t make large decisions for the entire country of 40,000, 50,000 units, uh, in 1 in 1 decision. I think it’s going to work in all places. You know, uh, making these macro decisions for a company, uh, that’s operating in different markets with different seasonality, with different expectations, with different unit size, unit type, um, you know, uh, even business model on the local level, you know, ski lease compared to, you know, short term compared to midterm, uh, making decisions across a large portfolio just doesn’t work in this business the way that I see it. So breaking this back down to there’s somebody who’s hyper local, there is somebody on the ground who can take care of those homeowners, uh, you know, the decisions that are being made when they’re closer to that front door of that property, uh, the better the outcomes are for all the stakeholders, you know.

Steve Schwab: [00:40:07] For the homeowner, for the guest, for the community itself, you know. Even for the teammates and employees that are there with them. So, you know, we see it over and over again when people try to scale, uh, from one market to another, they think it’s just twice as hard. But I always say it’s quadratically, more difficult. You know, it’s not just twice as hard. It’s four times as hard to go from one market to another. Um, and uh, you start adding on more and more markets, especially on a full service model. It becomes, uh, incredibly painful. So I think there’s a lot of different ways to get to success. I am not I’m not a I’m not a believer that, uh, the one that the model of consolidating it and trying to run it from a central operations is, uh, the probably the one way I would say is definitely not the right way to do it. Um, looking at, at it from a local level is going to have to be how you end up building this global brand.

Graham Donoghue: [00:41:04] Can I, And can I just suggest because maybe something I should clarify, which I don’t know. I don’t know if you’re aware, Steve, um, that we a little Sykes is like the parent company have had to forge the parent company. Sykes is the the power brand. We put a lot of marketing behind. We run 24 different brands in the UK with 40 offices all over the UK, and every single one of them has regional staff, employees that represent the local brand. So it’s not franchised because we own them. But the reason why we haven’t closed and consolidated them and turned them into like just just one power brand under Sykes is because we know the value of local relationships, the value of a local office, the value of being a good corporate citizen locally as well, you know, sponsoring the football team outside and stuff. And for us, it’s like a great way to maintain that, but also to hold on to the supply If I close them and get rid of them, I know deep down I would lose a big proportion of my supply because a lot of the owners we have, they don’t do it because they’re running it as a financially, you know, like lucrative business. It’s about relationships. So it’s not the same model, but actually it’s it has got similarities.

Steve Schwab: [00:42:22] Yeah, I totally see that. And the truth is, how many of your homeowners stay with you because of the local team, right? I mean, I can tell you that even in even in this, you know, a lot of the homeowners in Picasso said, I’m sticking with you guys because I love my local team. Right. So the fact that you’re empowering the locals, you know, and letting them make their own decisions and, uh, be close to the communities is a big part of what makes a property management company sticky.

Graham Donoghue: [00:42:47] Yeah. And it’s and it’s hospitality. Yeah. Because that’s that’s what, you know, they’re delivering hospitality to the owners, the hospitality to guests as well. So I apologize for interjecting there.

Simon Lehmann: [00:42:58] No, not at all. That’s a great, great input. So if I hear you, Steve, you know, I mean, you need to stay flexible. Um, you need to look at market by market. There is not one size fits all, uh, specifically. Also, you know, the type of homeowners and everything else. And at the same time, you could be devil’s advocate and say, hey, evolve has now 35,000 units on their platform exclusively as well. And, and run a, let’s say, a grand Donohue a business model in in the UK, in the US, which is quite interesting as well. So there’s room for a lot. But you know, the value creation. And I think one of the things I want to ask you, Steve, before we move to Corinne, uh, is in relation to that business model that a lot more operators are now trying to get rid of the service aspect, subcontract that, not doing the cleaning anymore, and more focus on the distribution and the brand. It’s it’s easier. It’s it’s it’s less of a headache and and and everything else. How do you deal with in your group or your organization with that aspect?

Steve Schwab: [00:44:08] You know, part of our vision talks about, uh, that we’re here to be invaluable to the homeowner when they’re away and a big part of our business model. And it’s not everybody’s business model, but our business model is to, uh, build a relationship that transcends business with the homeowners and to be their advocate on the ground when, uh, when they’re somewhere else, focused on something else. And, uh, we find that that’s our highest and best value, uh, and that’s how we build relationships and trust through competence, through intention, you know, through through being on the ground for them. Um, that’s how Casa is building our brand around it. And that’s not the only way to do it. Uh, going even more asset light than the franchise model to a a real, uh, you know, booking play, you know, is, is is certainly a valid business model. I don’t know if that’s going to ever be Chicago’s business model. I think we have components to that. But, you know, for us, uh, being the homeowners advocate on the ground and full services where we’re trying to put our values and build our brand from.

Simon Lehmann: [00:45:21] Chlorine before it gets too late. Um, in terms of your business model as well, uh, you’re not going to conquer the world and and scaling through real estate agents. Uh, what are your thoughts of your own? Um, because one thing that obviously the audience needs to know that that May Humphrey has Sydney and Melbourne running your own property management business, and the rest is run through real estate agents. What are your thoughts about now the business model you’re seeing scale through powering real estate agents with with a comfy pro versus running your own business. Well, how does how did that affect your or your how does that affect your strategic thinking in terms of your business model?

Quirin Schwaighofer: [00:46:02] Yeah.

Quirin Schwaighofer: [00:46:03] I think the advantage we have, we can do both. So we are definitely thinking about, um, like Sydney, Melbourne, we’ve been thinking a lot. We also sort of, uh, um, turn this into an Asian focused market. But in the end, we’re already here. We have a lot of relationships and, um, where our business model, like, really helps us with those relationships where it takes a long time. Um, if, if we launch a new market and with a new brand, um, to sort of build those, um, and for us, what we sort of have seen now and we then can be proud of, we call it a stealth for the first 2 to 3 years. And it’s only like 18 months ago that we announced it and we were growing, um, through purely through referrals. Um, it is something that, sort of enables the real estate agents that are losing properties to short term rental managers and of course, fast. Everyone that is missing out a little bit. Um, we, uh, we held them to create more value that gets us into those kind of communities. Um, they also sponsor the footy club of footy club. They also talk to the local developers. So yeah, for us, um, the core focus is on helping more real estate agents, um, helping them to be also like supply engines, um, giving them away a little bit from the hospitality side.

Quirin Schwaighofer: [00:47:33] So something that we’ve seen, um, real estate, especially the sales side, um, and the property management side is not really, uh, very close to what, what we do in regards to time, response time and, uh, on especially guest communication and things like that. So, so keeping those two things apart, um, really important part. But yeah we will and continue to focus in certain urban markets to run direct. We are part of oil now. Oil does not just do short term rentals. Um, but oil is not only operating in, in, uh, uh, in Australia. So, um, the, the idea is definitely to, to enable locations where all your operates, uh, to benefit from, from our business model. And that’s the exciting part as well. Like, for me, I’m a, um, entrepreneur throughout. Um, I love thinking, uh, five years ahead and then again, uh, you you get this call that puts you back into reality building. You don’t know what’s happening. If I know what’s happening in a year, I think that would be the end for me. Uh, just. I can’t add value anymore. But that’s the exciting part. Keep building, but also executing, um, writing things efficiently. Um, the whole AI time, um, that we’re currently in an incredible opportunity for everyone to, um, yeah, become especially more efficient as a person, um, and as a company. So. Yeah.

Simon Lehmann: [00:49:00] Fantastic. Thank you. And yeah, we managed exceptionally well for already 48 minutes without talking about AI. Graham brought it up after 20 minutes, which I thought was pretty pretty impressive.

Quirin Schwaighofer: [00:49:11] Typically begin.

Simon Lehmann: [00:49:13] And I.

Simon Lehmann: [00:49:14] Will do this.

Simon Lehmann: [00:49:15] We will definitely do a separate panel. There’s so many use cases out there. We really want to dig deep into AI. And we’ll definitely come back to that topic. Uh, when I see the use cases out there, uh, in today’s SDR world, already with all the agents, different languages, different, I mean, whatever it is, it’s just incredible. But at the end of the day, thank God we’re still the human capital. It still remains extremely important in the SDR space, and we’ll continue to do so being mindful of time. I want to wrap this up. And for the ones who sort of missed, uh, our investor panel in London in, uh, in, in May at the star, I want to bring that sort of last question to to my panelists in relation to what role plays technology, um, within, within our industry and um, and and then last and I include that what is sort of the global outlook for you, uh, in the next couple of years when we look at the short term rental industry. Are there going to be significant changes or not? But we talk about technology. How does that impact our business, and what do we need to be mindful about and what is the global outlook. Graham do you want to take that first?

Graham Donoghue: [00:50:23] Yeah. Well, I think as I’ve always said, technology for us is an enabler. Um, you know, we are a hospitality business, um, the blend of human capital to deliver exceptional or even unreasonable hospitality, if you want to gather with technology is what we think is our superpower. And again, I don’t we don’t really talk about AI, but for the moment, you know, I see this wave happening in terms of how AI can really help and unlock, um, you know, extreme sort of a competitive advantages for people who will lead into it. So technology is really important. Um, but I think the people who will win with the company, who can blend technology and the human capital sort of together because that acts as a moat around your business and, well, you know, unless you’re a pure play technology company, um, I think the outlook generally, this industry has been around for a hell of a long time. You know, I have brands in my portfolio that are 60 years old. Um, you know, it’s it’s very resilient. Um, you know, I think it’s been really tough the last 3 or 4 years. It’s been really tough. I do think there is some light at the end of the tunnel. I think we are coming out the other side, but I do think there will be more consolidation. I do think we will probably see some people sort of falling away, whether we’re going to see the level of investment in the sector that we’ve seen historically. I think the jury is still out, you know, on that one. Maybe we’ll wait the next 12 months. We’ll see what’s happening. Um, but I’m pretty optimistic about, you know, about the future. And I think I’m pretty confident that, um, you know, there’s going to be some great businesses that continue to evolve and do some incredible things, um, and, you know, and deliver exceptional experience.

Simon Lehmann: [00:52:11] Awesome. Thank you. Graham. Great summary, Steve.

Steve Schwab: [00:52:15] Yeah. So I think that over you know, we looked at the next five years, we’re going to see a lot more consolidation of tech and operators. Uh, you know, here in the US, uh, tech is going to evolve and accelerate. I think, uh, to Graham’s point, making sure that we’re using it to enable our people and, uh, you know, our interactions is going to be important, making this, you know, bionic so that we have more time to spend in the human element as opposed to robotic, where people are just getting to interface with chatbots. That doesn’t feel like there’s a true hospitality partner involved with them is, uh, is going to be important. Um, I think that we’re going to see a lot of resistance towards OTAs coming up. We’re already seeing, uh, you know, some, um, some certainly some people who feel like, you know, that they’ve, that the OTAs aren’t, uh, are being fair. Um, a lot more focus on book direct strategies and, uh, you know, and then hopefully we’re going to find some, uh, institutional capital backing brands with both, uh, scale and soul to them. And so, you know, over the next five years, I think that that’s going to be important as we take technology, mixed it into the human portion of our business, and then trying to just preserve jobs for our teammates to make sure that our, um, our face to face brand is there. It’s not a phase two, uh, AI brand. Uh, it’s going to be.

Simon Lehmann: [00:53:40] Important.

Steve Schwab: [00:53:40] As we go forward.

Simon Lehmann: [00:53:41] Thank you Steve. Amazing. I love the OTA input as well. Uh, had a recent conversation about that understanding where the demand is coming from in the future, something we need to spend a lot of time on. I’ve seen an article yesterday how Booking.com is utilizing TikTok for distribution, uh, while the channels are shifting. So it’s going to be super interesting to see that too. Corinne.

Quirin Schwaighofer: [00:54:04] Yeah. To sort of be the the last one here to add a few things, I think, uh, to be the last. Yeah. No, I think to summarize all of this, um, um, what will be key? Whoever builds trust at scale, um, will be able to reach this target of, uh, of what we talked about being really global. I do believe AI will help us to focus more on those moments of truth and which I personally interactions. That’s from the moment you meet a property owner for the first time, that’s when you, um, have to help a guest. That’s when you when you work with your, uh, cleaning teams, with your with your tradies. This will remain remain all hands on activities. Uh, I think until we see robots do that. That is maybe not in my lifetime or maybe not in my working lifetime. So yeah, technology will help us to to focus on those moments of truth. And I think business models are also sharpening further. And yeah, I think really exciting time to be to be in um, at the moment in our industry and in, in general with, uh, all the tools we have these days and in access to information, um, and those global panels.

Simon Lehmann: [00:55:14] Awesome, fantastic. Gentlemen, I really, truly want to thank you. I hope that Graham will find Loch Ness with his binoculars behind him. Um, and thank you.

Quirin Schwaighofer: [00:55:26] Is that what it’s for? It’s like.

Simon Lehmann: [00:55:28] Must be.

Quirin Schwaighofer: [00:55:29] It’s it’s for.

Graham Donoghue: [00:55:31] It’s 14 miles long. This loch. It’s big.

Quirin Schwaighofer: [00:55:35] Yeah.

Simon Lehmann: [00:55:35] So, uh, thank you for joining us today. This has been super intriguing. Some great takeaway. Trust at scale blend technology and human capital, is there more investment to come? Is a question more consolidation? We all see that too. Hey, and think about where OTAs are heading and where your booking is coming from in the future. Ladies and gentlemen, thank you so much. Steve Schwab. Have a wonderful day. You’re up early, so you have still a fright ahead of you. Graham, you’re close to a drink in the afternoon. And. Quirin. Good night. Thank you so much for joining us. Our global Unlocked and wishing you a wonderful evening and a great weekend ahead. That was STR Global Unlocked, where we say what others won’t. If you got value from today’s episode, send it to someone who is still playing it safe. Follow the show and get more global insight at Angel of Telecom, the globally recognized STR consultancy I founded, and that proudly brings to you this show. More bold conversations are on the way, so stay tuned.

Vacation Rental Companies Need Leaders With A Passion For Generativity

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There’s no doubt that today’s STR and VR leaders have to be technophiles, embracing
the ever-changing world of the business ecosystem and somehow managing to get all
their API- connected tech to work in unison. Unfortunately, the required attention on the tech stack comes at the opportunity cost of focusing equally on the “people stack.”

I read and hear a lot of talk bemoaning today’s workforce, with words like entitled,
unengaged, and unmotivated being thrown around. But from what I see as a hospitality industry trainer who spends 70+ days a year teaching lodging industry workshops filled mostly with Gen Z and Millennials, the real issue is the lack of inspired leadership.

My impression of the younger generations who are early on in their careers is that most of them are hungry and eager to learn, like a bottle of resin poured into a mold, waiting for a drop of catalyst to convert it to become solid and durable.

It’s clear to me that behind every smiling face greeting guests is an inspired leader with a passion for “generativity.”

Generativity is my new favorite word which I came across recently in reading an article on psychology. However, the word itself is certainly not new, and when I researched its etymology, the word became even more meaningful to me. The term generativity was a minted by Erik Erikson in the mid-20 th century as part of his theory of psychosocial development throughout one’s lifetime, which contrasted with the Freudian focus on childhood experiences having an oversized impact.

According to Erikson, humans go through 8 stages of development in life, each
presenting a sort of conflict of choices. In middle adulthood, the choice is between
stagnation or generativity, which he defined as a desire to mentor, guide and nurture the next generation.

One reason the word really hit with me is because at my phase of my career, when so
many peers are eagerly taking early retirement, what keeps me out on the road 38% of my life (138 days each year) is what I now know to be generativity.

While it’s always been rewarding to receive positive feedback at the end of my training workshops, or afterwards in the form of emails and DM’s, I now recognize that these messages are even more meaningful. I just love it when I bump into participants from many years ago who share comments about how our seemingly “micro” encounters have somehow had a lasting impact on their career paths.

Perhaps Erikson was right when he talked about that while parenthood is one way to
express generativity, teaching, sharing knowledge, and engaging in one’s community
provides another option for those who are not parents or for those who are empty-
nesters.

Generativity is Erikson’s positive alternative to the other option he identified, which is
the stagnation that results from self-absorption and unproductiveness in middle age.

There’s lots of great things that will come about when you foster a spirit of generativity among your leadership team. Not only will your frontline staff benefit from the mentorship and your guests benefit from the positive hospitality experiences delivered by satisfied staff, but your leaders also benefit as well from knowing they are leaving a legacy in this world.

I often teach a class I call “The 3M’s of Hospitality Leadership: Model, Measure,
Mentor,” which has a strong focus on mentoring, (which I will hereafter call generativity.) One of our activities is to break out in teams and share a story about someone from earlier in your career who mentored you, and how that impacted your career thus far. When I ask for volunteers to share their stories with the general session, nearly every hand goes up. And more than once a tear is shed as participants reflect gratefully on those who have touched their lives.

If you want to inspire a passion for generativity in your leadership team, I highly suggest an activity like this as a starting place.

RealTimeRental Assembles Industry Veterans to Drive Innovation in NewEra of Vacation Rental Technology

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[Ocean City, NJ — October 2025] RealTimeRental, the pioneer behind the vacation rental industry’s first cloud-based software platform, today announced the addition of key advisors and leadership talent to guide the company through its next major evolution – RealTimeRental 2.0, a comprehensive rebuild of its platform designed to meet the rising expectations of guests, owners, property managers, and real estate professionals.

Joining RealTimeRental’s Advisory Team are two respected industry voices:

  • Annie Holcombe, founder of Annie & Co, co-host of Alex & Annie Podcast – The Real Women of Vacation Rentals, and board member of The Vacation Rental Management Association (VRMA), brings decades of experience in marketing, operations, and brand storytelling across hospitality and vacation rental sectors.
  • Jeff Bedard, founder of Bridgefield Advisory and former President of Compass Real
    Estate, joins as a strategic advisor focused on customer insight and experience,
    innovation strategy, and product-market alignment.

Leading RealTimeRental’s expanded Executive Team is:

  • Tony Maganzini, formerly of Parakeet and Brivo, who will drive strategy and market expansion efforts as Chief Strategy Officer.

“RealTimeRental changed the industry more than 25 years ago when we launched the first web-based SaaS property-management system,” said RTR Founder, Joe Testa. “We’re about to do it again – not with a facelift, but a complete reinvention from the ground up, built to exceed the high expectations of our customers.”

RealTimeRental 2.0: Built for Rising Expectations

The company’s 18-month RealTimeRental 2.0 initiative represents a significant reinvestment in talent, technology, and customer research. This next-generation platform is designed with the financial and operational muscle to handle even the most complex, high-volume vacation rental operations while providing unmatched flexibility for boutique firms and growing teams alike.

“Guest and owner expectations are rising fast – faster than most software has evolved to keep up,” said Jeff Bedard. “RTR 2.0 is a direct response to that reality. RealTimeRental is listening to customers, building for the next generation, and delivering a platform that reflects where the industry is heading, not just where it’s been.”

RealTimeRental 2.0 will deliver:

  • Unmatched Flexibility: From the most complicated office workflows to simple streamlined setups.
  • Enterprise-Grade Financial Backbone: Designed to handle compliance and sophisticated accounting with ease.
  • Scalability for All: From established brokerages to startups entering the short-term rental market, RTR 2.0 delivers the foundation to grow.

“RealTimeRental 2.0 is not a version upgrade – it’s a generational leap,” added Tony
Maganzini
. “Our focus is on empowering professionals to deliver exceptional experiences to their guests and owners while operating at peak efficiency.”

In parallel with these product investments, RealTimeRental has launched an extensive
Customer Insights Discovery Program to ensure that every feature and workflow reflects the needs of its user community. The research, conducted over recent months, revealed a clear call for modernization, transparency, and mobility across every level of the rental ecosystem – from booking to accounting to owner relations.

“Once again, the industry is guessing what RealTimeRental is building,” said Joe Testa. “But just like when we launched, we’re stepping ahead. We’re engineering a platform that defines the next era of performance, reliability, and growth for our customers.”

For more information or to request future demo access to RealTimeRental 2.0, visit
www.RealTimeRental.com or follow RealTimeRental on LinkedIn.

The 2026 Workforce Wake-Up Call: How Engagement and Retention Will Define Business Success

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As we move toward 2026, one thing is clear: employee engagement and retention are no longer HR buzzwords—they’re the lifeblood of a sustainable business.

Across industries, organizations are facing a convergence of forces reshaping the workplace: rapid technological advancement, shifting workforce expectations, and the reality of a five-generation workforce sharing the same space.

In this environment, the organizations that thrive won’t just be those offering competitive pay—they’ll be those that create cultures where people feel valued, connected, and seen. High turnover and quiet quitting aren’t just symptoms of burnout—they’re signs of a disconnect between what employees need and what businesses provide. Engagement and retention strategies for 2026 must go beyond surface-level perks and focus on deeper, human-centered practices that meet employees where they are.

1. Create a Culture of Belonging

Diversity and inclusion have been center stage for years—but 2026 calls for the next evolution that has been percolating for a few years: belonging. It’s the difference between being invited to the meeting and being asked for your opinion. It’s the difference between having a seat at the table and having your voice heard and valued. Belonging fuels engagement. When employees feel that leadership and their direct manager are invested in them, then they are emotionally connected to their team and confident that their perspectives matter. They invest more energy and creativity in their work.

This sense of connection looks different across generations:

  • Baby Boomers value being recognized for their experience and want opportunities
    to mentor others.
  • Gen Xers seek autonomy and respect for their independence.
  • Millennials crave purpose and collaboration—they want to feel their work means
    something.
  • Gen Z expects authenticity and psychological safety; they engage best in
    environments where transparency and empathy are the norm.

To build belonging, leaders must listen intentionally and lead inclusively. That means
conducting stay interviews, encouraging open dialogue, listening to your people, validating people’s experience and feelings, and empowering managers to build genuine relationships through empathy and consistent communication. Owners and C-Suite mistakenly hyper-focus on senior leadership team. Where it is most impactful is the investment in your managers: recruit to retain.

Belonging doesn’t show up on a spreadsheet or engagement survey results—it shows up in small, human moments. When a leader asks, “How are you really doing?” and takes the time to genuinely listens. When a manager catches a change in tone and checks in with care. When someone in the office remembers what makes a teammate smile on their birthday. These moments of empathy and awareness are the real indicators of emotional intelligence—and the building blocks of a culture of belonging with measurable increases in retention metrics.

2. Prioritize Manager Capability as a Retention Strategy

People don’t leave companies—they leave managers. Since the phrase first gained traction in 1999, its truth still holds today—for good reason. In 2026, the ability of front-line managers to engage, develop, and retain talent will define organizational success. Yet many managers are stretched thin, juggling hybrid teams, shifting policies, and competing priorities—often without the training or support needed to lead effectively on the human side of work. The most forward-thinking organizations are changing that by investing intentionally in manager capability as a core driver of retention and performance.

Effective managers share a few traits: they communicate clearly, know their people, give timely feedback, and know how to coach rather than command, judge, or avoid. They don’t just manage performance—they manage people. From an HR perspective, this means providing tools, templates, and ongoing coaching. Regular one-on-one check-ins, use of engagement dashboards, and manager accountability metrics can turn performance conversations into retention moments.

Managers must also learn to adapt their leadership style by generation:

  • Boomers appreciate respect for legacy knowledge and visible acknowledgment of contribution.
  • Gen X thrives with flexibility, autonomy in their work, and trust in their independence.
  • Millennials look for mentorship, purpose, and feedback loops.
  • Gen Z wants transparency, clear boundaries and expectations, and career pathing early in their journey.

There is little accountability without trust. Trust is associated with words like truthfulness and reliability. It is built over time through repeated demonstrations. When trust levels are high in a relationship, conflicts can be more easily resolved and sometimes avoided entirely. When managers meet employees where they are, trust grows—and trust is the foundation of retention.

3. Design Flexible Work Models That Reflect Real Life

Flexibility is no longer a benefit—it’s a baseline expectation. The challenge heading into 2026 is to design flexibility that supports both productivity and well-being.

Different generations define flexibility differently:

  • Boomers may value predictable and traditional schedules and in-person collaboration.
  • Gen Xers, Millennials and Gen Z see flexibility as control—where, when, and how they work best. They prefer to work in hyper-productive blocks on time rather than on an eight-hour time block.

Organizations must shift from rigid structures to adaptive frameworks. This includes hybrid work options, flexible hours, and creative scheduling approaches that align with the business’s needs and the employee’s life.

Flexibility also means investing in cross-training, thoughtful seasonal workforce planning, and clear pathways for advancement. Knowledge and decision-making silos no longer serve today’s dynamic workplace. When employees see their employer providing real opportunities for access, collaboration, and balance—not just talking about it—loyalty and trust grow.

Flexibility doesn’t mean chaos—or catering to trends. It means clarity. Clear expectations, communication norms, and accountability systems allow flexibility to strengthen engagement rather than weaken it. As Brené Brown reminds us, clear is kind—and in today’s workplace, clarity is the foundation of trust.

The HR takeaway: flexibility is strategic, not operational. It’s a long-term investment in system adaptation, retention, and resilience.

4. Invest in Growth, Learning, and Purpose

Heading into 2026, employees want more than stability—they want growth and purpose. Career development and meaningful work consistently rank among the top drivers of engagement, especially for Millennials and Gen Z. However, Boomers and Gen X also crave opportunities to stay relevant, mentor others, and feel their experience matters.

The most effective leadership teams are reframing learning from a cost to a catalyst. They’re using training and development as engagement engines—embedding upskilling, mentorship, and leadership development into daily work life.

Here’s what that looks like in practice:

  • Personalized learning paths: Role-based development plans aligned with business goals, with mentorship flowing upstream and downstream. 
  • Cross-generational mentorship: Pairing Boomers’ expertise with Gen Z’s digital fluency builds connection and mutual respect.
  • Growth conversations: Shifting from annual reviews to ongoing career discussions keeps employees engaged in their own trajectory.
  • Purpose-driven storytelling: Communicate the “why” behind the work. Employees who understand the impact of their role—on guests, homeowners, or the community—stay motivated.

Learning fuels belonging and reinforces culture. When people see a future for themselves within an organization, they’re far less likely to look elsewhere.

5. Measure What Matters: Engagement, Retention, and the Employee Experience

Data has become HR’s superpower. But as we enter 2026, it’s not about more metrics—it’s about the right ones.

Engagement and retention are influenced by a blend of emotional, operational, and experiential factors. Organizations that use people analytics effectively can identify issues before they become turnover trends.

Key metrics to track include:

  • Engagement scores: Are employees connected, motivated, and aligned with your company’s mission?
  • Retention and turnover rates: Where are you losing people—and why?
  • Manager effectiveness: Do teams with stronger leaders show better engagement scores?
  • Training participation and impact: Are learning initiatives driving performance improvements?
  • Employee Net Promoter Score (eNPS): Would your employees recommend your organization as a great place to work?

Pair quantitative data with qualitative insight—stay interviews, pulse surveys, and roundtable discussions. Numbers reveal what’s happening; conversations explain why. In 2026, HR’s role is to translate data into dialogue and action. The goal isn’t simply to track turnover—it’s to understand the emotional temperature of the workforce and respond with intention.

6. Generations at Work: A Bridge, Not a Barrier

A multigenerational workforce isn’t a challenge—it’s a competitive advantage when led with intention. Each generation contributes unique strengths and perspectives that, when harnessed, can drive innovation, resilience, and connection.

  • Boomers offer legacy knowledge and mentorship.
  • Gen Xers bring adaptability and pragmatism.
  • Millennials drive collaboration and innovation.
  • Gen Z champions diversity, inclusion, and digital fluency.

The opportunity lies in creating connection points—through cross-generational projects, reverse mentoring, and team discussions that highlight shared values rather than differences.  A 2026-ready organization doesn’t try to homogenize its workforce; it harnesses diversity to strengthen engagement and fixes friction points. Leaders who understand generational dynamics build bridges instead of silos.

The conversation isn’t about who’s right or wrong—it’s about learning from each other. As one Gen Z professional recently said during a leadership panel: “I don’t want to replace the generation before me—I want to build on their legacy.” That mindset is the essence of modern engagement.

Looking Ahead: Engagement as a Strategic Imperative

As we approach 2026, employee engagement will continue to evolve from a cultural initiative to a business imperative. Engaged employees don’t just stay—they innovate, advocate, and elevate performance across the board.

Retention, in turn, is the outcome of trust, communication, and care. It’s earned, not expected. From an HR perspective, success lies in integrating engagement into every process—from recruitment and onboarding to performance management and leadership development. Engagement isn’t a program; it’s a promise—to value people as much as performance. Employees will go the extra mile when they believe their leaders will walk beside them.

The future of work isn’t just about technology or flexibility—it’s about humanity, practicing non-judgment, and staying curious. When organizations lead with empathy, invest in growth, and build cultures of belonging, they’ll not only keep their people—they’ll keep their edge.

Five HR Priorities for 2026—At a Glance

PriorityFocus AreaKey Actions
1. BelongingConnection & inclusionCreate safe spaces for dialogue; celebrate diversity; encourage storytelling.
2. Manager CapabilityLeadership & communicationTrain leaders in emotional intelligence, feedback, and coaching.
3. FlexibilityWork-life alignmentOffer hybrid and adaptive schedules; clarify expectations and accountability.
4. Growth & PurposeCareer developmentPersonalize learning paths; use mentorship to bridge generations.
5. Data-Driven EngagementInsight & actionTrack eNPS, turnover, and engagement; use feedback to drive continuous improvement.

Final Thought

As 2026 approaches, the war for talent is being replaced by a race for engagement. Employees want connection, not control; growth, not gimmicks; and leaders who listen more than they lecture.

Businesses that understand this shift—and act on it—will stand out not just as employers of choice, but as cultures of choice.

At its core, engagement and retention aren’t HR initiatives—they’re human ones. They thrive when people feel seen, valued, and connected to something bigger than a job. In hospitality, we work diligently to give guests reasons to stay and return. The same question applies internally: Do you know why your employees stay? Because in the end, engagement and retention aren’t HR’s responsibility alone—they’re everyone’s responsibility. They’re what happens when people feel part of something worth staying for.

Marketing Messaging That Actually Converts Vacation Rental Homeowners

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2025 vacation rental e-commerce website web store marketing

You’ve probably heard it before: some vacation rental manager claiming to be “the best in the city” or promising “guaranteed best revenue,” which sounds too good to be true. 

Here’s the uncomfortable truth: nearly any marketer can trick a handful of property owners into signing up with flashy promises and misleading statistics. But that’s not sustainable business. Those relationships crumble when reality doesn’t match the hype, and owner churn is the killer for vacation rental businesses both large and small. 

The vacation rental management companies thrive long-term? They’ve mastered something entirely different. They’ve built marketing messages that don’t just grab attention, they create genuine, lasting partnerships with homeowners. And it all comes down to understanding five critical elements that most managers completely overlook.

Why Most Vacation Rental Marketing Messages Fail (And How Yours Won’t)

Let’s start with why most vacation rental marketing falls flat on its face.

The typical approach sounds something like this: “We’re the #1 vacation rental management company in [City Name]. We guarantee maximum revenue and white-glove service.” Sound familiar? That’s because every other management company in your market is saying nearly the exact same thing.

The problem isn’t that these statements are necessarily false, though they often are. The real issue is that they’re meaningless. When everyone claims to be the best, being “the best” becomes worthless as a differentiator.

But here’s what’s even more damaging: these generic promises create unrealistic expectations. When a homeowner signs up expecting “maximum returns” and their property generates average revenue, they feel deceived, even if you delivered exactly what you said you would.

Sustainable marketing messaging works differently. Instead of making grandiose claims about being the best, it focuses on being the most relevant. It speaks directly to the specific concerns, goals, and situations of your ideal homeowners. And most importantly, it sets realistic expectations that you can consistently exceed.

Think about it this way: would you rather have 100 homeowners who signed up based on inflated promises (and will likely leave within a year), or 50 homeowners who joined because they genuinely understood and valued what you offer?

The companies that choose the latter approach don’t just survive, they dominate their markets through word-of-mouth referrals and long-term client relationships.

Attention: Why Traffic Is Your Foundation (But Not Your Solution)

Let’s address the elephant in the room: if homeowners aren’t seeing your marketing, none of this matters.

You could have the most compelling value proposition in the world, but if your website gets three visitors a month and your social media posts reach nobody, you’re essentially marketing to yourself. Attention, whether through digital advertising, SEO, referrals, or local networking, is the foundation of everything else.

But here’s where most vacation rental managers make a critical mistake: they think traffic alone equals success. They focus entirely on getting more eyeballs and completely ignore what happens after someone actually visits their website or sees their ad.

I’ve seen management companies spend thousands on Facebook ads that drive plenty of clicks but generate zero inquiries. Why? Because they treated attention as the end goal instead of the starting point.

Here’s what actually works: targeted attention that reaches the right homeowners at the right time. Instead of casting a wide net hoping to catch anyone with a vacation rental, successful managers identify their ideal clients and focus their attention-getting efforts specifically on reaching those people.

For example, rather than running ads that say “Vacation rental management services,” try “Own a vacation rental in [Specific Neighborhood] but tired of handling late-night guest complaints?” The second approach will get fewer total views, but significantly higher engagement from people who actually match your ideal client profile.

Remember: attention without relevance is just noise. Your goal isn’t to be seen by everyone, it’s to be seen by the right homeowners who are actively looking for what you provide.

Presentation: Every Touchpoint Is a Make-or-Break Moment

Here’s something most vacation rental managers don’t realize: your marketing message isn’t just your ad or your website’s homepage. It’s every single interaction a potential client has with your business.

Your presentation includes:

  • The initial ad that caught their attention
  • Your website’s design and content
  • How quickly you respond to inquiries
  • The professionalism of your email communications
  • Your sales pitch during the consultation
  • The contract terms and signing process
  • Your onboarding experience for new homeowners
  • How you handle the inevitable problems that arise

Each of these touchpoints either reinforces or undermines your marketing message. And here’s the kicker: homeowners judge the consistency between what you promise and what you deliver at every single step.

Let’s say your marketing message emphasizes “premium service and attention to detail.” But when a homeowner fills out your contact form, they get an automated response with typos and don’t hear from a real person for three days. What message does that actually send?

The most successful vacation rental managers treat every touchpoint as an opportunity to strengthen their brand. They audit their entire client journey, from first contact to ongoing management, looking for “rough edges” that contradict their marketing message.

This might mean:

  • Redesigning intake forms to feel more professional
  • Creating email templates that maintain your brand voice
  • Training your team on how to handle difficult situations in ways that align with your values
  • Streamlining your contract process so it feels as premium as your marketing promises

The beautiful thing about this approach? Every improvement you make compounds over time. A smoother onboarding process doesn’t just make new clients happier, it makes them more likely to refer their friends.

Your Unique Selling Proposition: The Difference Between Claims and Proof

Most vacation rental managers think a Unique Selling Proposition (USP) is just a catchy slogan or a list of services. They’re wrong. A true USP is a provable claim that separates you from every competitor in your market.

Here’s the test: if your USP can’t be disproven, it’s not actually unique. Anyone can claim to “maximize revenue” or “provide exceptional service.” But can you prove it?

Let’s break down what proof actually looks like:

Revenue Claims: Instead of “We maximize your rental income,” try “Our properties average 23% higher revenue than self-managed properties in the same neighborhoods.” Then show the data. Screenshots of actual performance comparisons, anonymized financial reports, or third-party revenue management platform data.

Service Claims: Rather than “We provide white-glove service,” demonstrate it: “We respond to guest issues in under 2 hours, 97% of the time.” Then show your response time dashboard.

Local Expertise Claims: Don’t just say “We’re the local experts.” Prove it: “We’ve managed properties in [Specific Area] for 8 years and maintain relationships with 12 local vendors who provide priority service to our homeowners.”

But here’s what makes a USP truly powerful: it should make your service sound like the obvious choice for your specific target market. If you specialize in luxury mountain cabins, your USP should make homeowners with luxury mountain cabins think, “These people clearly understand exactly what I need.”

The strongest USPs often combine multiple elements:

  • Unique Value Proposition (what specific benefit you provide)
  • Unique Timing Proposition (why now is the right time to work with you)
  • Unique Price Proposition (how your pricing structure benefits the homeowner)

Your USP should answer this question for every potential client: “Why should I choose you over every other option available to me, including managing my property myself?”

If you can’t answer that question with specific, provable facts, you don’t have a USP yet. You just have marketing copy.

The Offer: Transforming Your Service from Commodity to “Only Choice”

Even if you nail everything else, attention, presentation, and USP, a weak offer will kill your conversion rate. Because at the end of the day, homeowners don’t just choose based on who you are or what you promise. They choose based on what you’re offering and how it compares to their other options.

Most vacation rental managers make the same offer mistake: they present their service as a commodity. Standard management fee, standard services, standard terms. When your offer looks identical to everyone else’s, homeowners shop on price alone, and nobody wins a race to the bottom.

A strong offer does two things:

  1. It makes your service feel unique and non-interchangeable
  2. It prevents you from becoming a free marketing source for your competitors

Let me explain that second point. When you create demand for “vacation rental management” in general, but your offer isn’t compelling, you’re essentially doing marketing work that benefits your competitors. Homeowners start shopping around, and the company with the lowest price or the best salesperson wins, regardless of who actually created the initial interest.

Here’s how to craft an offer that positions you as the only logical choice:

Bundle Unique Components: Instead of charging a management fee plus extra charges for marketing, cleaning coordination, and maintenance oversight, create a package that includes everything under one transparent price. Call it something specific, like “The Complete Care Package” or “Hands-Free Revenue Management.”

Add Time-Sensitive Elements: “We’re currently accepting three new properties in the [Neighborhood] area for our 2024 program.” This creates urgency without feeling artificial.

Include Risk Reversal: “If your property doesn’t generate at least X% more revenue than your current management approach within the first six months, we’ll refund our management fees.” This shifts risk from the homeowner to you, but only make this guarantee if you can actually deliver.

Create Exclusive Access: “Homeowners in our program get priority access to our interior design consultation service and preferred pricing with our partner vendors.”

The goal is to make homeowners think, “I can’t get this exact combination of services and guarantees anywhere else.” When that happens, you’re no longer competing on price, you’re competing on value, which is exactly where you want to be.

Response Instructions: Making It Effortless for Homeowners to Say Yes

You’ve captured attention, delivered a strong presentation, proven your USP, and made a compelling offer. Now comes the moment of truth: how easy is it for interested homeowners to actually take the next step?

This is where many vacation rental managers snatch defeat from the jaws of victory. They make the response process so complicated, unclear, or intimidating that potential clients give up before they even start.

Your response instructions should answer three questions immediately:

  1. What exactly should the homeowner do next?
  2. What will happen after they take that action?
  3. How long will the process take?

Here’s what doesn’t work: “Contact us to learn more” or “Call for a free consultation.” These instructions are vague and put the burden on the homeowner to figure out what happens next.

Here’s what does work: “Click here to schedule a 15-minute property assessment call. We’ll review your property’s revenue potential and discuss how our program works. No sales pressure, just honest insights about your property’s opportunities.”

Notice the difference? The second version tells homeowners exactly what to do, what to expect, and how long it will take. It also removes the fear of being pressured into a decision.

For even better results, consider offering multiple response options that appeal to different personality types:

  • For research-oriented homeowners: “Download our Property Performance Analysis worksheet and see how your property compares to similar rentals in your area.”
  • For action-oriented homeowners: “Schedule a 15-minute call to discuss your property’s revenue potential.”
  • For cautious homeowners: “Join our monthly webinar where we share market insights and answer questions from local property owners.”

The key is making each option feel like a natural next step rather than a high-pressure sales situation.

Conclusion: Building a Marketing Message That Scales and Sustains

Here’s what separates vacation rental managers who build lasting businesses from those who constantly struggle to find new homeowners: sustainable marketing messages that attract the right clients for the right reasons.

When your marketing focuses on attention-grabbing gimmicks and unrealistic promises, you’ll always be chasing the next marketing tactic or dealing with disappointed clients. But when you build your message around genuine value, provable claims, and client-focused offers, something amazing happens: your marketing starts working for you instead of against you.

Homeowners who join your program actually stay. They refer their friends. They become advocates for your business instead of cautionary tales.

The five elements we’ve covered, strategic attention, consistent presentation, provable USP, compelling offers, and clear response instructions, aren’t just marketing tactics. They’re the foundation of a vacation rental management business that grows through reputation rather than constant prospecting.

Start with one element. Maybe that’s auditing your current presentation touchpoints, or developing proof points for your USP claims. Perfect that piece, then move to the next. Because sustainable success isn’t about having perfect marketing from day one, it’s about continually improving every aspect of how you attract and serve homeowners 

How Brian Egan Built Evolve Into a Profitable Short-Term Rental Business & What’s Next for Vacation Rentals

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Brian Egan is the Co-Founder and CEO of Evolve, a Denver-based hospitality company with a mission to become the most trusted brand in vacation rentals. Since launching Evolve in 2011 alongside Adam Sherry, Brian has grown the company to support over 35,000 properties and more than $5 billion in rental revenue.

If you’re navigating the complexities of short-term rentals, this episode offers insights you won’t find in a press release. Brian shares what it takes to build trust at scale, how to grow without losing your identity, and why consistency still beats tech when it comes to guest experience.

In this conversation, we discuss:

  • What inspired Brian Egan to leave a career in law and launch a brand focused on rebuilding trust between guests, owners, and property managers
  • How Evolve’s approach challenges the traditional property management model and redefines what it means to scale in a low-trust category
  • The early struggles of building Evolve and why Brian believes trust, not inventory, is the key to winning in vacation rental
  • How the short-term rental industry lost its identity and what it takes to build a brand in a fragmented, tech-dominated space
  • What most founders miss about balancing owner expectations, guest satisfaction, and profitability at scale
  • Why consistency, experience, and human connection, not just tech, are shaping the future of vacation rentals

Connect with Brian Egan on LinkedIn [https://www.linkedin.com/in/brianwegan/] to learn more about Evolve Vacation Rentals [https://evolve.com/].

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1Transcript

Introduction: [00:00:00] You don’t have to do it all on your own, and there’s no extra credit points for making it harder on yourself than it needs to be. And we saw that as a really important way to his internationalization.

Introduction: [00:00:10] Is that a topic for your investors, for yourself?

Introduction: [00:00:12] They’re looking at this as something that they want as a combination of an investment and a lifestyle asset. Right. And that blend. So it’s not for everyone.

Introduction: [00:00:20] You’ve opened probably about ten cans of worms to say the least.

Introduction: [00:00:24] At the end of the day, it’s a team that matters. And that’s why no matter what AI does, anyone doing it on their own is never the right answer.

Simon Lehmann: [00:00:34] You are listening to STR Global Unlocked, brought to you by AGL artillery, the show where I speak with the leaders shaping short term rentals worldwide. I am Simon Lehman and after two decades buying, selling, advising and investing, I’ve built a network that spans continents and categories. This podcast brings that network to you. Real conversations, global insight, no PR fluff. Let’s get started. Hi everyone! Today I’m joined by someone who has been right at the corner of our industry’s evolution. My guest is Brian Egan, a seasoned entrepreneur, an investor and advisor in the travel and hospitality space. Brian has spent his career building and scaling businesses that challenge traditional models, and he’s become one of the most respected voices in the short term rental industry. He brings a rare mix of founder experience, strategic perspective, a global insight, having navigated everything from startup grind to cross-border expansion, capital raising and scaling in a highly fragmented industry. Brian, I don’t want to spend the entire time of introducing you. Great to have you.

Brian Egan: [00:01:50] Good. We have much more interesting and important things to discuss, but it’s great to be here. Simon. Thanks for having me.

Simon Lehmann: [00:01:55] I really enjoyed, uh, our times we spent together over the last few years as, uh, industry thought leaders. And I have, uh, an utmost enormous respect for you and what you have built with evolve. And, uh, would love to hear a little bit about your personal story as a founder and operator, to start with.

Brian Egan: [00:02:16] Sure. Yeah. Um, you know, for me, I was not one of these kids who was nine years old, uh, you know, selling things on the school play yard and knowing what I wanted to be an entrepreneur. It actually, uh, struck me much later. Uh, I started my career, actually, in Silicon Valley, working in the tech and startup and venture capital industry as a lawyer. Uh, realized after a couple of years that wasn’t the path. I was at the right table, but in the wrong chair. Uh, switched over to go to my first hospitality business, Exclusive Resorts, based here in Denver, a luxury destination club. It was one of the first ten employees there, spent seven years helping to build that company and then really saw the opportunity, uh, along with my co-founder, Adam, uh, that the short term rental industry represented. You know, at that point, this was, uh, you know, 2010, early 2011 when we kind of made the decision to take the leap. We ended up beta launching evolve It by the end of 2011 with a whopping 21 homes on our platform. Uh, and you know, what we saw at that time was a mainstreaming industry, one that was still quite nascent with myriad unsolved problems. And we felt like there was a solution out there to be found between the idea of a DIY owner operating on their own and the traditional full service local property management model. So that’s what we set out to build. And here we are today.

Simon Lehmann: [00:03:36] Well that’s incredible. But let’s go a little bit deeper there. In terms of what was the the the initial idea, I mean, doing a DIY, uh, within a market where it was still clearly dominated by a lot of professional property management companies. I mean, Airbnb just started to ruffle feathers. Homeaway was around the corner trying to digitize Craigslist as well. Like what was sort of the starting thought points of you to build evolve to start with?

Brian Egan: [00:04:09] Yeah, so I’d say the core thesis was one this industry will mainstream. And that sounds obvious today. But let’s remember this is 2011 and it was anything but mainstream. I mean, as you just pointed out, Airbnb at that point I think had was a series a business still largely in the metro apartment sharing type of beachhead. We all knew where they were trying to go, but they hadn’t done it yet. Um, and at the time, you know what we now call Vrbo but at the time was HomeAway was a classified ad site. You couldn’t even book a property on the site. All you could do was request a book and you might hear back from an owner. I think at that time, if I recall correctly, you know, a rate table for a listing on HomeAway had six rows. So you could have like a spring rate and a summer rate and a holiday rate. Uh, and that was about it. So it was a it was a super nascent industry. Um, so thesis number one, this is going to mainstream ten years from now. It’ll be way more common and popular for either an owner to rent out their home or for a guest to choose vacation rental, uh, as their format for travel. Second thesis was with that, the market will become increasingly complex and competitive, and that that is going to mean that the bar is going to have to go up.

Brian Egan: [00:05:16] We’re going to reach that mainstream consumer, that mainstream guest. They are going to come into this category and expect to shop and buy and enjoy this wonderful business that we’re in the same way they do air, hotel and car, and they’re not going to be willing to put up with things like, oh, the rates were inaccurate, the calendar wasn’t updated, the listing wasn’t as advertised. The owner never got back to me. I mean, myriad things that were going on. So it is going to become more complex and competitive. And with that, it’s going to become more challenging for both DIY owners do it yourselfers or for rent by owners, as we call them, or the local property managers who had been operating in their world for 20 or 30 years. We thought that all created this kind of ground for disruption. And then the third point would be what does that disruption look like? We believed it needed to look like a management platform. So a vacation rental manager that could partner with these owners on an exclusive basis. So we become that calendar and system of record for them. We could do all the things you need to do to drive that booking, to take care of that guest, to take that work off of the owner’s plate and remove that fear and uncertainty and doubt that so many owners have.

Brian Egan: [00:06:21] They need that help, but also offer them some flexibility and some control and choice in the things they care about most, whether that be selecting the on site vendor that they want to use for housekeeping, or things like snow removal, whether that be elements of revenue management, you know, minimum rates and things that they may want to say that they really care about. Hey, if I’m not going to be in the home during Christmas, I want at least this much money. So we believe there was an opportunity to create something that was a bit lighter weight, faster moving and offered owners really a unique value proposition. And in exchange for all that, of course, also a lower management fee that we felt like was going to be very attractive in the market. That was the basic hypothesis. Um, and by the way, I mean, all these years later, I would say good news. We were right. We were probably early. Uh, we also convinced ourselves we were wrong at different points along the way and messed some stuff up. But if you go back and look at what we actually believed in the basement when we were just two people there, uh, a lot of it actually is pointing straight at what we’re still building today.

Simon Lehmann: [00:07:23] So what did you mess up? I mean, you just took one of my next questions, obviously. Fast forward 14 years to see, you know, in terms of your thesis. What what did you underestimate or overestimate in terms of challenges? And what did you mess up on the way?

Brian Egan: [00:07:35] Yeah. Well, I would say the first thing we messed up was, uh, we we sort of heard from everyone, right? That. Oh, this is going to be really hard. It’s going to be really hard to find these owners. And and that was right. I mean, it was harder than I think we expected to identify these individual owners out there in the market and partner directly with them. That was you know, it’s it’s not a consumer brand where 80% of the folks on the internet are actually the right clientele for you. So figuring out how to get there was difficult. We’re also trying to convince people to do something that no one’s ever offered them, so they don’t have a mental model for it, right? So all of that took a lot longer than we thought. That’s actually not the mess up, though. That’s just I think part of like trying to build a sort of model and come at an industry from a new angle. That’s part of the game and we were up for it. The part we messed up was actually losing our conviction. So we actually were about a year, year and a half into the business and we started to say, gosh, this just is not growing as fast. We’re going to figure this out.

Brian Egan: [00:08:34] But we can’t be 80 year olds, 80 year olds by the time we do. Right. And as we got to that point, we also had some property managers calling us and saying, we see what you’re doing. We’d love to partner with you. It won’t be exclusive, but we’d bring, you know, 20, 30, 50, 70 units onto your platform and have you serve as one of our distribution channels. And we tested it. It looked pretty good. We doubled down on it. It was a huge mistake. And once we got to the place where we were no longer in an exclusive partnership with the person who actually controlled that asset, the owner who paid that mortgage, you know, that was that left us kind of in a in a zone of being yet another layer and a middleman that could be disintermediated. And what we realized was it was a fast way to build a much bigger business, but not a good way to build a durable business. And so we actually spent another 6 or 12 months unwinding that and kind of going back to the original thesis and just bearing down on we’re going to figure this thing out one owner at a time and brick by brick, build this business up.

Simon Lehmann: [00:09:34] So all your owners are exclusive on the platform, correct? Yes. And you only do single channel distribution, which is evolve itself, right? So you don’t redistribute the content to other platforms?

Brian Egan: [00:09:45] No, no, we actually we distribute all over the place. So we distribute to Airbnb, Booking.com, Expedia, Vrbo, uh, and a longer tail from there. We’re a big partner of Marriott Homes and Villas uh, by Bonvoy. Uh, so yeah, no, we part of, part of our model is to handle all the distribution on behalf of that owner, in addition to having evolved as a direct channel.

Simon Lehmann: [00:10:06] Is that something you started right from the beginning that you said, hey, we’re so so that must have been very hard. I mean, even today to think about that, people still and even property managers, especially in the US, but also in other, uh, animal Saxton markets still do single channel distribution or like very few. That must have been very challenging to to offer a multi-channel distribution approach. If you see now all the companies that go after the long tail like small Bu and rentals and toolkit and and home to go with their brands and it’s unbelievable. So you started so early with that approach. And to see now that everybody is going after the long tail, uh, is quite interesting.

Brian Egan: [00:10:50] Yeah. You know, for us, the thesis was this OTAs, if you think about vacation rental or short term rental versus hotels, hotels have been in business for, you know, 2000, 3000 years before the OTAs came along. But especially in the US. And by the way, I mean, uh, I know you have a global audience for your podcast, which is wonderful. I want to make sure that I’m caveating my answers to your questions are our operation is, you know, vast majority domestic in the US. So, uh, in the US, the short term rental industry is actually quite nascent. And it was very unorganized. And, you know, the OTAs, so to speak, if you call the earliest version of Vrbo or HomeAway sure to they actually came of age on the internet at the same time as the short term rental industry came onto the internet right in the mid to late 90s. And so for us it was, hey, these marketplaces are actually a very helpful organizing function for an industry that needs to go through a massive mainstreaming curve. And we’re way better off getting on that wave and writing it and letting the then home away’s now vrbos, letting the Airbnbs, letting the ultimately Expedia’s and Booking.com, you know, letting them create some of that wave that we can ride. I mean, look, I’m, I’m an entrepreneur and I love building and being disruptive and taking new angles. But you don’t have to do it all on your own. And there’s no extra credit points for making it harder on yourself than it needs to be. And we saw that as a really important way to drive value for our owners.

Simon Lehmann: [00:12:17] Excellent. Yeah, I will definitely go back to your entrepreneurship a little bit later in our conversation and hear some of your learnings also with the team and to human capital you’re engaging with. I have, uh, the $100 billion question, uh, when we talk about market structure and, and supply structure as well. Um, we talked about supply structure for such a long time. And we differentiate between long tail, which is basically the DII, the RPO rent by owner, do it yourself, uh, owner. And uh, and let’s make the demarcation line 20 properties, uh, always said, you know, up to 20 properties. You can still keep your day job. And then after that it gets tricky. Um, call it, uh, the professional market 20 plus. I don’t want to ruffle anybody’s feather, but let’s, uh, settle on on 20 properties. One thing that I found very interesting over time to sort of follow these, the data of all the big data providers who, when you look at the long tail versus the manage tail, that this has not really shifted at all over, over all these periods of time. And I was always the one wearing the PMC and the professional hat and said, you know, that line that the professional supply is going to grow and the RPO, rbo are part of the business in terms of supply is going to shrink over time. And interestingly enough, if you consume data over the last even a decade or five years, seven years, half a decade, it hasn’t really shifted. And and why is that? And I would love to hear your opinion on that.

Brian Egan: [00:13:52] Yeah, it’s a fascinating question I agree. It is the $100 billion question. Um, here’s here’s my take for today. It’s a dynamic industry. And ask me again tomorrow. I think that you saw this immediate surge of DIY owners, and this is back when everything was hard and Vrbo was a kind of a crappy classified ad site, if we’re being honest. Right? They would say that.

Simon Lehmann: [00:14:16] College will be on the podcast as well.

Brian Egan: [00:14:18] I’m perfect. Nobody knows it better. Nobody knows it better. So, you know, that was like the minute that that was an offer. You saw a huge part of the market say, I’m ready to go right around this managed layer, because when you have a lack of competition, right. The managers in a lot of these markets before that was an option. There wasn’t a lot of competition. They could kind of price at the level they needed. They didn’t have to like, you know, fight it out for that business. We all know that competition is going to make markets improve. So immediately you kind of by the time we got into the market, it was already about a 5050 balance. Now, why hasn’t DIY taken over and owned 80% of the market? I think it’s because it’s hard. I mean, you’re taking on I think you really have to do this well as a craft. It is becoming a micro hotelier, and you can see the hosts and the, you know, DIYers who are so good at this, you know, it takes real energy, passion, time, skill. You know, you have to be willing to have your phone on on your bedside table. You got to be really excited about it. Now, good news. Millions of people are right. And I think that’ll be a part of our industry forevermore. And I think it’s a really important part of our industry.

Brian Egan: [00:15:27] But I’ll also say it’s not for everyone. And when you look at, for example, our owners, most of them have double income. You know, husband and wife are working. They’ve got kids in school or just out of school. I mean, they’ve got very busy lives and they are not looking at this as something they want to do as another job. They’re looking at this as something that they want as a combination of an investment and a lifestyle asset. Right. And that blend. So it’s not for everyone. But on the other side, you’ve got the professional management layer, what I’ll call like local full service management. Why hasn’t that grown. Well, because one it’s expensive. I mean, in order to do that business right, you have to be boots on the ground, local. You have to have installed teams. You have to have a pretty heavy infrastructure. There’s real opex involved, right? You got a lot of pieces that are moving around there. And at the end of the day, if you load up all the fees and look through the whole thing, you’re going to end up paying at least 35 and more likely 40 to 45% 5% for that service. Now, for many owners, that’s a great deal. It’s I don’t want to worry about it. I want to, you know, I want to be able to text the person taking care of the home.

Brian Egan: [00:16:35] Wonderful. So our whole point was, hey, why don’t we come into the middle of this and say, we can do a lot of the things that you need as a partner? We can allow you some of that flexibility. Um, so I think that’s why we’ve seen this relative stasis, uh, and I think as the business as the industry moves forward, you know, my view is that, uh, a disruptive offering is going to be increasingly attractive. I mean, I don’t think we’ve seen, for example, we’ve seen seven, eight, nine, ten years of better and better DIY tools come to market. You know, whether that was originally with the pricing apps, most recently with AI tools. I’m not sure any of it has actually changed the market share, you know, and we’ve also seen a lot of consolidation and movement on the full service local property management side. Again, not sure we’ve actually seen any shift in market share. So from our point of view, we look at activating new owners that evolve every month. We have hundreds and hundreds of people who are joining evolve and bringing their home on the platform. Uh, most of them are new to the market and have never rented that home out before. So we really view the expansion of the market and growing the pie as a big opportunity. Wow.

Simon Lehmann: [00:17:46] Very comprehensive answer. You’ve opened probably about ten cans of worms, to say the least. Uh, so let’s try to close my skills. Let’s try to close some of the Brian and, uh, you know, you used words like consolidation. And so if I understood you correctly, uh, you would argue that the market split in terms of professional versus long tail is going to remain about the same. Um, you know, people switch and whatever. But let’s talk about your business. Let’s let’s talk about Long Tail for a second. Um, obviously you’re you’re in North America. We’re having visibility across Southeast Asia, uh, um, Australia and also Europe and Latin America. And the market is slightly different. Um, but in a way, the split between between professional versus long tail is about the same. Depending on market. Certain markets are a lot lower and certain markets are higher. But in general, on average, it’s about the same. But what we’re seeing is that we’ve seen a lot of, um, technology transaction recently, a lot of, uh, capital flows into the industry, a lot of private equity capital flows into the industry. And we’ve seen a number of very interesting, uh, let’s say business plans and, and value creation plans in their pitch decks, uh, to private equity.

Simon Lehmann: [00:19:06] And interestingly enough, a lot of these, uh, technology platforms that are out there raising significant amount of capital or exiting as well, they put their growth strategy into the long tail. So so that means it’s going to get tough out there for you. Uh, because everybody says, you know, the professional managed market is is so competitive and it’s so hard to to gain more market share. You spend a lot on marketing. You go to conferences, you’re moving teams around the world to to grab more professional property managers. And and the acquisition on the long tail is obviously more online marketing and online acquisition, um, through communities, etc.. So I, I would argue that you are going to see a lot of competition of technology platforms who have built multi-channel distribution, channel management, revenue management, content management, PMS functionalities, and that stuff is there. And then it’s obvious that some of these companies can say, like, now with what we have built, we go after a long tail with a with a light solution and we can offer the same.

Brian Egan: [00:20:15] Right. So I would say a couple of things there. One, I totally agree with you that that is what’s happening out there too. It’s not new. I mean, I remember sitting in, uh, the basement and looking at there’s an accelerator, a seed accelerator program here in the US called Techstars. And we saw right as we were getting started, we saw somebody building a set of DIY tools that were going to be software based and become the big disruptor in the industry. And, you know, I guess I’ve just seen it come and go. Now, that said, I think these are the best tool sets out there to date. Um, and I think that’s great for owners, but if you’re not somebody who wants to do it yourself, who has the skill, the ability, the willingness and readiness to do that, it’s not going to matter. I mean, I can buy you a better and better power saw, but if you’re not somebody who’s actually a do it yourselfer, it doesn’t really help you. Right. A lot of people are going to need a partner in order to navigate a market that, by the way, what you’re what you’re saying there is that market is becoming increasingly complex and competitive. And for a lot of owners, that’s going to mean that they need to or want to have a partner to help them navigate that space.

Brian Egan: [00:21:25] Now, that all said, I think it’s also important to say, you know, we we view that as good. We view all the advancement. I mean, there is going to be ten, 15, 20 years from now. There are going to be DIY owners on the best tool sets we’ve ever seen. There’s going to be full service local management at a premium price, and I believe there’s going to be robust scaled hybrid solutions in which I believe evolve will be the winner. That’s how I see the world unfolding, and this isn’t going to be a winner take all. But I do believe that within those categories, there are winners take most. And that’s what I really see evolve as. My last thought is, you know, Simon, look, if if that’s what owners want, there’s no saying we can’t deliver it as well. Right? Because what we’re doing today is standing in the shoes of the owner. Right? We’re marketing and booking all of their properties under the evolve brand. We’re talking to their guests. We’re handling a lot of their revenue management, etc. if owners are really keen to to do it on their own, we have the toolsets, we’ve built them for ourselves and there’s no saying that we couldn’t offer them as well.

Simon Lehmann: [00:22:27] So where would you say robust? Where would be the biggest differentiators to these DIY tools, DIY tools that are out there in relation to evolve, with the exception of the brand that you have built?

Brian Egan: [00:22:40] Well, yeah, I mean, number one would be the end to end us taking the property from, hey, I’m thinking about entering this category to a high performing online listing that’s being distributed with high fidelity to every channel out there that’s being priced to its optimization point. That’s, uh, and revenue managed to that point where all the guest inquiries are being handled by us, where we’re coordinating with your on site provider of choice, in many cases, a, a partner that we’ve introduced you to, uh, through our vetted embedded network. Right? So yeah, it’s the I mean, this is basically a new format of management where the owners are able if they want, they’re able to sit back and more or less get, you know, booking notifications in their app and dollars in their bank account. Um, but on the other hand, we also have the ability for owners who want to lean in a bit and act a little bit more like that DIY, for example, we have revenue management, uh, levers that are available to our owners. They can actually use these tools to say, hey, this is the minimum price I want for that specific week. Great. No problem. You can do that. And you can do that really easily through our owner app.

Simon Lehmann: [00:23:50] So why so obviously now would be the great opportunity to move your business, uh, across borders and, and internationalize that business model because it’s obviously there’s clear differentiation. You have a lot more stickiness from a technology standpoint, from a branding standpoint and what you offer, uh, also to the to the owners. And this is not about, the marketing show of evolve, but it’s about talking. How do you navigate within that landscape? And and obviously you have raised a significant amount of capital as well for your for your business and growth. And, and is internationalization, is that a topic for your investors and for yourself?

Brian Egan: [00:24:30] Well, absolutely. I mean, let’s start. First of all, I remember you asking me this question the first time we met, uh, many, many moons ago at a conference, uh, which was a funny story unto itself, but, uh, it was one of the first three questions you asked me. And I think my answer is going to remain the same, which is from a vision perspective. It’s absolutely global. I don’t think there’s any reason why our innovation into building this hybrid management model, uh, a bit of a best of both worlds can’t be successful anywhere in the world. The answer to when is, uh, uh, by the way, the other thing would be, let’s also talk about whether that would be go to Europe, where that’s, you know, a much more mature market, many more established incumbents. Sure. Decades. Decades older than the US. Or whether that’s more like a Latam or APAC. Type of market where it’s much more nascent. So you can have all those debates. I can tell you the when answer, which is, as soon as we believe that it won’t distract us from becoming the market winner in the US. Right. As soon as we believe that we are at a point where that is the next best and heaviest lever to pull in order to grow. And right now we look at the US and it’s still the largest greenfield opportunity out there. I mean, you still have, uh, hundreds, thousands of owners every day, every week who are coming into this category. You still have a lot of people moving around between models trying different things out. You know, we believe this remains our biggest opportunity. And importantly, because of our model, we were always able to operate across the entire US, right. So we never went market by market. Yeah. And we didn’t take inventory from primary markets, secondary and tertiary markets. So for us, there’s just so much opportunity here in the US that we still want to make sure that we’re, you know, we’ll never be perfect, but we we see an opportunity to keep raising our bar here. And then eventually yeah, the vision is to be global. Certainly.

Simon Lehmann: [00:26:23] We have uh, we have seen a lot of pitch decks and fundraising decks that have put out international strategies to their investors, uh, raising an enormous amount of capital. And nobody in our industry has managed to become truly international. And we could we could, uh, talk a lot about different brands. I think Picasso is one that, uh, speaks for itself. They’ve tried an internationalization strategy. At the end of the day, synergies were not there. Wyndham sold their business in 2018, Wyndham Vacation Rental as well, uh, which is now away. So we’ve seen we’ve seen it. I’ve done it myself with Interhome. We looked at the US market. We couldn’t do any significant intercontinental cross-border business. It’s just there’s just no synergies. There’s nothing there. You’re not getting more guests from one place to another because of it. Um, in the traditional PMC business model and it just totally failed. Um, and it’s going to be extremely difficult. And we hear it all the time. Now we see franchise models. Um, so which model do you think? And what would be the advantages in terms of building internationalization? I think one of the biggest issues that we have in our industry, that we have not been capable of building a significant consumer facing brand to drive demand, right.

Brian Egan: [00:27:40] Yeah. So, I mean, I think the reason that it hasn’t worked with the traditional full service model is the same reason that it hasn’t worked to actually scale that model and centralize it nationally, even just in the US. Right. Because it’s a big country, uh, with a with a lot of different nuances and nooks and crannies to it. And so what I think happens in those businesses is two things. One, it’s inherently quite local. It’s inherently, uh, you know, there’s nuance to each market. And then two, as you point out, the synergies break down because there aren’t any, um, there are no economies of scale to performing that kind of manual labor. Right? That kind of fixing this, shoveling that, you know, pushing a vacuum cleaner that actually, in many cases has diseconomies of scale. Once the homes get further and further apart. Right, you got to put people back in a van and drive them down the road, the whole deal. So we’ve seen in the US, it’s interesting to note we’re now seeing the largest players that are full service are all pushing to highly localized models, whether that be through a franchise type of arrangement or whether that be through a roll up in which you let the underlying asset continue to operate locally. Yeah, that that seems to be, you know, what the market consensus has landed on in terms of that full service model. And I think that is also why it hasn’t really worked on these international. Expansion fronts. In terms of the model that can work.

Brian Egan: [00:29:09] I would say one, that’s where the software tools have an advantage, right? Certainly you’ve seen more of them make that leap, more of them operating in. I don’t know if anyone’s really built a big business doing it yet, but I think it could happen. Um, and then two, if you’re going to do it, I think our model is the right one where you’re partnering locally for local services, where we don’t have thousands of housekeepers and maintenance people and bus drivers on our payroll. We partner for all those services locally, and in some cases, the owner is the one actually securing that partnership because they have a preferred vendor. So for me, I think that is the model that could do it. The last thought I have on this topic too is, is, you know, look, we there’s no saying that we have to go do it on our own. I said earlier, no extra credit points for a degree of difficulty here. Right. Uh, so, you know, there is always an option of saying, hey, it may make sense at some point to look at establishing a foothold through inorganic growth. I mean, to date, we have nearly 35,000 properties on our platform. We have grown completely, 100% organically, brick by brick. We’ve won every single one of those owners individually. And so, uh, you know, that said, we’re not dogmatic about it. And if there was an acquisition opportunity that made sense as a way to, you know, look, cross border, we certainly would take a close look at that.

Simon Lehmann: [00:30:27] Yeah, maybe I would have some ideas here, but let’s, uh, take that offline. Uh, there’s always opportunities out there.

Brian Egan: [00:30:33] I didn’t mean to trigger your deal brain there.

Simon Lehmann: [00:30:37] Yeah, but, I mean, that’s what we do, right? We’re connecting dots and, uh, and and getting the right people together to, uh, to professionalize and grow this industry. That’s what makes us excited. Um, let’s talk about technology a little bit. Uh, overall and the way you look at, uh, the short term rental industry, you know, and I sort of feel, um, I’ve seen Brian, uh, more in the past than I’m seeing him now. Which, uh, tells me he’s not so much into the conferences anymore because of where you’re at, right? And it makes a ton of sense. I mean, you’re focusing on a different business. I mean, you’re not gonna you’re not adding property managers on your platform to do distribution that that you have done. That’s probably when we saw you more often at property management conferences. But now you’re running after your brand and your deal and you’re growing your business. So you’ve in a way created also some some of the distance with the learnings that you’ve had on the platform, uh, to have integrated the PMCs. I remember the days when we were the first property manager in the world, uh, with so many properties in Europe to integrate with HomeAway. It was a nightmare, right? But anyway, how how do you look at the traditional property management industry, like predominantly in the United States right now?

Brian Egan: [00:31:53] Yeah. And specifically, you know, from through a technology lens. Um, you know, I would say for us, we have a model that is unique. And therefore, while we did actually start and operated for maybe 18 months on a third party system that we were trying to customize the heck out of, ultimately what we concluded is we need to build our own operating system because there isn’t, uh, you know, there isn’t a market for a big software company to build something for us because we’d be the only ones using it. Uh, so, so, you know, uh, and by the way, I certainly, uh, I don’t mean to be under the radar screen. You’re right. The bigger conferences, I mean, we don’t really have anything to buy or sell at those conferences. Uh, but we do have, uh, you know, our teammates are there, uh, talking to our biggest partners, especially the OTAs and such. Uh, and just so everyone in the industry knows, I’m always available. Anyone can reach out. Uh, don’t mean to be, uh, don’t mean to be off the radar, uh, but, you know, from our from a technology perspective and a bit of, you know, to your point on focusing on the business, you know, we have just gone through an overhaul. So we had built a system in year two of our life or so. Uh, and that reached the end of its useful life and was ready to be replaced. And we have gone in the last 12 to 18 months, we have been systematically overhauling our entire tech stack.

Brian Egan: [00:33:10] Uh, and actually, that work will largely come to completion. You’re never done. But, uh, the, the sort of big migration will be complete by the end of this year, which I’m really excited about. It puts us on a much more modern, much more flexible tech stack and, uh, and allows us to unlock a lot of velocity of product development, a better owner and guest experiences. It certainly unlocks the future, uh, for our business in terms of leveraging AI. Uh, so we’re super excited about it. In terms of what I see out there, it’s interesting. I mean, I think there were a number of people that were trying to do more of their own platform development, uh, and ultimately concluded that that wasn’t the right path. And I see why. I mean, if you’re running a model that everyone else is, you know, that is largely the same model as other people. Well, then there’s going to be a market for people to build great software for it. And again, no extra credit points, like why would you go build your own PMS if yours isn’t going to be as good as whoever guessed streamline? Pick your pick your partner. Right. Uh, so to me that does make sense. But it’s interesting to see, you know, for example, I think Costco has recently, you know, in the wake of the acquisition of Picasa, has said we’re going to use, uh, I believe it’s, uh, streamlined. I can’t remember exactly which one.

Simon Lehmann: [00:34:24] Going from streamline and using GST as well.

Brian Egan: [00:34:26] Oh, to GST. Yeah. And then you know that they were partnering with uh, wheelhouse for revenue management. Right? I mean, that’s an interesting move for one of the largest companies in the space to make, you know, our version is that we’ve built those tools in-house. We’re perfecting those tools in-house. I’m not declaring right and wrong here. I’m just saying it’s a it’s interesting to see. And I think from a tech perspective, it seems like the legacy full service industry is more moving to the scaled third party tools, and that that motion is going to sort of settle there. And then again, people will continue to try to innovate on better DIY tools that’ll that’ll last forever. Um, and, you know, we’ll see where that goes. And as they make it easier and easier, it should be more attractive. But on the other hand, that’s been happening for ten years. And as we just discussed, it doesn’t mean that every owner is opting into that into that format.

Simon Lehmann: [00:35:15] Yeah, I would totally agree. I mean, the discussion of proprietary software versus what’s coming off the shelf, that has definitely shifted significantly also in Europe and and also in the in Australia and other markets where people, you know, in the early days, people had to build proprietary software because there was nothing there. But the evolution of technology within the SDR space has been huge for the last few years. And one of the pitches that Eric and Cliff has done to raise capital for Kosovo was obviously building a, you know, a technology company, but at the end of the day was a full service PMC and you’re still dealing with unit density, manpower, operation, opex and everything else. And I guess for, you know, being the devil’s advocate, it’s easier for you to say, because you’re looking at it from the SaaS lens. And and at the end of the day, you know, a lot of people try to combine that. And we had interesting conversations at at the conference last December in, in Florida about this and, and this proprietary tech play that’s gone, that’s history. Now, even, you know, Steve Schwab and others clearly said, you know, this this positioning also from from an investment standpoint, you know, we’re a we’re a SaaS driven service business. It’s sort of a service as a software instead of software as a service. It’s it’s it’s quite interesting.

Brian Egan: [00:36:39] Um, yeah. You know, and look, I, I mean, these are smart people and they’re making, you know, really, I think thoughtful, data driven, analytical decisions. I think it’s the right thing for their model. I can tell you it’s not the right path for our model, but again, that just sort of proves the point that what we’re doing is, is different. Um, and then, you know, I would say, you know, for us, a big part of this is setting the stage for where we can go with AI, which is just, I mean, the most exciting thing. What a gift. I mean, I, uh, I can’t believe that I am one of the few people who’s lucky enough to one be in the industry for a long time, you know, to get to take a journey like this. Um, and then to be at this stage of it and have, you know, the, you know, at least a generational and arguably the biggest technology shift in platform shift ever, uh, happen while we’re in a position to really take advantage of it. I mean, again, surfing that big wave, you know, for us, we look at AI and say, this is the it’s the perfect technology to do the things that we do. It’s not the perfect technology to vacuum homes. It’s not the perfect technology to shovel snow and, you know, fix toilets. But I’ll tell you what, it’s really going to be helpful when it comes to pricing, distribution. You know, uh, guest and owner support, uh, and all the things that are really at the core of our business, uh, in terms of providing incredible performance, incredible service and amazing experiences for guests.

Simon Lehmann: [00:38:10] Yeah, we manage 37 minutes and 20s not to talk about AI. That’s pretty impressive. I didn’t mean to do that, but.

Brian Egan: [00:38:17] He gets the best.

Simon Lehmann: [00:38:18] Of me because I wanted to ask you about it because your whiteboard behind you is is white. So that means you’re, uh, you’re introducing AI in your business.

Brian Egan: [00:38:27] I was furiously wiping this off, uh, before you hit record.

Simon Lehmann: [00:38:32] And I’m sure you have some other big buddies. And obviously Graham Donahue from Sykes is also a huge fan and has developed his business significantly into that direction as well. And I could not agree. I mean, it’s definitely going to be a game changer significantly for for good and worse in all different use cases. We need to see how this evolves. But we also have understood that we need to stay on top of that as good as we can, because it is revolutionizing. I’ve seen some incredible use cases within this industry already on AI and and it’s it’s happening. Um, absolutely. So let’s move on.

Brian Egan: [00:39:06] And look back back to the point that you made though, right? This isn’t just about narratives. I mean, you can get look, you can get by if you’re a clever, uh, you know, salesperson and everything else. And entrepreneurs are known for their, uh, their charm at times. Right? But ultimately, there’s a scoreboard. Ultimately, there’s the initial performance of the business. And at the end of the day, every business is ultimately worth their future cash flows. Right. And so I think it’s really important that, you know, my excitement about AI is not about a narrative. It is not about something flashy. You don’t see it written all over our website today. You don’t see me on stage at the conference shouting about it, because I think that we’re still at the very beginning, and I don’t think that we have the, you know, end results. And this isn’t just evolve. I would argue this is the industry. I would argue this is enterprises more broadly. We’re just now in 2025, I think, starting to see really interesting enterprise level use cases for what’s happening. And it’s only going to continue and compound. And I’m terribly excited about it. But not not for the glitz, not for the headline and the narrative. I’m incredibly excited about it because I think what it can do is elevate the experiences of our owners, our guests, our teammates, and ultimately improve the financial performance of our business. Free up more capital to invest in the growth of the business and the elevation of those experiences, rather than fundamental operations. That technology is going to ultimately be in a better position to perform for us. So so that’s that’s the why behind it for me?

Simon Lehmann: [00:40:39] Does that mean that Brian Egan is going to run away on his own? No, no.

Brian Egan: [00:40:44] First of all, that would be that would be a terrible decision for the business. Uh, I am wrong way too often for that to be. That would be a disaster. Uh, I need a smart team around me to keep me in check and keep me between the lines. Uh, no, not at all. And actually, I don’t view this as, um. You know, I think a lot of people start to talk about this as, like, technology just replacing people. I, I’m sure in some businesses that may be the case. It’s not how we think about it. How we think about it is how can this incredible technology change what that role is? You know, how how do you go and where do you go, by the.

Simon Lehmann: [00:41:21] Way, to human capital? Yeah.

Brian Egan: [00:41:22] You know, and and change what it means to be. So you’ve got somebody who’s in owner support, right. This is a critical function in our business providing incredible service to our owners. Well, we don’t really need I mean, our teammates aren’t dying to take a call that says I’m locked out of the website. Right. Our teammates aren’t dying to take a call to ask a question that they’ve been asked 14,000 times, and will be asked another 14,000 times. If owner and owners aren’t dying to log a case or place a phone call in order to get something done that they could get done with a push of a button in an app and an agent could take action on their behalf. So that is literally just making the owner experience better, and it’s making our teammate experience better. And of course, yeah, it’s also freeing up opex for us. But it’s not really about oh, that way we get rid of that teammate. What it’s really about is how can we take that talented person and then have them in a better position? Because guess what, there’s going to be another scenario because, as you know, short term rental, like, look it’s a great industry, but these are homes and things happen right. You can have somebody clean the home on Friday for a Saturday check in. And the person gets there on Saturday. And the tree fell on the back porch. Right. I mean, this is the stuff that happens. That’s when owners need incredible humans who are passionate and well trained and well versed in the industry. And I don’t think that that’s what AI is going to take over. Like, I think that’s where it’s human to human, and you’ve got to be really good, and we’ve got to have relationships with on site partners and all the rest. But hey, let’s take all the the stuff that our team would tell you is the least favorite part of the job. Let’s take that off the table and redirect our energy into the stuff where we can really make a difference.

Simon Lehmann: [00:42:56] Let’s move on. I totally agree with you. And, uh, you know, this is going to be definitely interesting how this evolves. Not everybody has the same opinion about it and how you do create efficiencies. And also what does it do to the human capital, but especially in the short term rental industry, the humans are real, are today and will in the future remain the most important capital, uh, within the industry being, um, on the SaaS side, uh, but also being on the operational side, you know, so that’s definitely what’s going to happen. So let’s talk about it.

Brian Egan: [00:43:29] It’s a team that matters. And that’s why, by the way, no matter what AI does, anyone doing it on their own is never the right answer.

Simon Lehmann: [00:43:36] Yeah, that’s why we love the short term rental industry. Let’s face it. Right? So, um, let’s, uh, as a closing topic, I would want to sort of talk about, uh, investment landscape and uh, especially once again, we’re talking to a global audience. Um, and, uh, you know, we’ve raised capital in Australia. We’ve seen the markets in Southeast Asia, Europe. It’s like raising capital has become significantly challenging. Uh, the narrative in relation to property managers has become more a service business than a software business is going to be interesting to see. But we’ve still seen for for large business a significant amount of capital flowing into this industry. We still see pretty big, uh, transactions. It’s going to be interesting to see if more and more is going to come in, uh, because it’s a service business that they’re financing. We’ve seen, uh, large transactions with thousands of units that have attracted capital. There’s a group out there right now who is trying it again to do a roll up, uh, private equity backed. So that’s going to be interesting. But I want to focus with you more on the technology front. And how do you view the landscape, uh, in relation to capital? We’ve seen some significant valuations in the PMS side with guests and Hostway and others who have raised significant amounts of capital, uh, from, uh, piece. We didn’t have that in the past because the growth and the size was just not there. And now, finally, these companies get to a level where it’s becoming interesting for mid and large cap private equities to invest into the into the business. So my question to you, how do you view the investment landscape in general. Also for smaller businesses fragmentation is not going to go away so quickly. Even though we felt the tax space is going to be consolidated very quickly. I say on the channel management a few other fronts, we have clearly seen it already. Also in the PMS side, I. I think markets will consolidate. Now. All these AI tools are popping up like mushrooms. They all need capital. So what’s happening there?

Brian Egan: [00:45:37] Yeah, well, my first answer is you probably know more than I do in the sense that I’m I’m proud to say that evolve is now a self-sustaining, profitable business. And so I haven’t personally been out in the capital markets in quite some time. Uh, that said, of course I keep my eyes open and my ear to the ground and, uh, you know what? I’m what I’m noticing is, is, is a couple of things that you touched on. First of all, I would say overall, I’m just tremendously excited to see capital flowing into the category. And you could define the category broadly as everything from the core tech tools to even the what I would say is kind of adjacent short term rental kind of hotel replacement. I saw, um, Casa, uh, raised around I saw that announced a couple days ago. So anywhere in that whole spectrum, I think any capital coming in is a great sign, because what it tells you is that the capital market is very smart. Investors who have been watching and watching and watching and analyzing have gotten to the place where they said, yep, it’s ready to grow again, right? Because we went through a period of time where everybody the bloom was kind of off the rose. Uh, you know, there was, uh, some, some big public offerings. And there was, you know, obviously significant decreases in stock prices thereafter. The whole growth company world went through a correction in pricing, interest rates went up, all the things that we all know.

Brian Egan: [00:46:59] And so I think for a minute there, the category just sort of became, uh, less attractive. Now I’ve been, you know, I’m 25 years into my career and I can tell you that, you know, those markets are the best ones to invest in, that when everyone’s talking about it, that, you know, the opportunity has already passed you. And so I think you’re starting to see the early signs that some investors believe this is a growth category. The second thing I would say is, yeah, to your point and to your global audience. The the PMS companies seem to be the ones attracting certainly healthy valuations, which is great to see, and I suspect that it’s the Tam. I suspect that it’s the idea that, hey, this is, you know, this is a big market that you can scale into, um, which is which is exciting. It’s also very interesting to see that, yes, capital and a significant amount of it is flowing into some of these more operational, more like traditional PE businesses, really, at the end of the day. Um, obviously at very different multiples, obviously, you know, with a different view of, of, of what’s happening. But I do think that there seems to be I mean, you know, what’s old is new and, uh, you know, the rollup I’ve been watching the rollup play since Resort Quest, uh, since Wyndham bought Resort Quest.

Brian Egan: [00:48:10] Since Picasso bought Wyndham. I mean, you know, we’ve been we’ve been watching it for a while. I do think there’s some new approaches. Uh, today, again, like a franchise model, you know, letting these companies operate more Independently in local markets, and I suspect they will be more successful with those approaches. But it’s really interesting to see that that’s you know, the consolidation piece seems to be the other thing that’s attracting capital. Now, that said, step back as a market. What does that mean? It doesn’t mean a lot right. The number of properties in the market didn’t change. The you know, it’s moving some chess pieces around on the board. Yeah. That’s true. The number of properties in the market didn’t change. And the market share of local full service management for a premium price also didn’t change. So from our perspective, it’s. Yeah. Well, I mean, are they bigger competitors? Sure. Um, but does that actually change the value proposition or anything that’s, you know, the dynamics of the market over the last ten years? Not really. Um, and I wish them all the success. I mean, I think for us, the better they perform, the more attractive the category, the more likely that new owners get interested in the category. And we’re going to win our fair share. Well.

Simon Lehmann: [00:49:20] First of all, congratulations on the performance. And that’s great. Uh, so obviously great not to have to go out and raise more capital. And, but you still have a very strong opinion on how the market looks like. And, and I’m sure you get plenty of phone calls instead. So you’re on the receiving end as well. And that’s part of the game, right? I mean, people investors are looking for opportunities and, and uh, and, and as you, as you said and I totally agree, that’s great for the category. Uh, you know, we’ve seen also some failures, uh, also the PMC side, which for sure didn’t help the industry at all because it didn’t work out, because I always made the argument that the largest for property management companies in Europe, with 50,000 properties, they’ve been around for 60 or 70 years. They’ve never lost money. Right. So, uh, it can be done. Uh, it just depends how you do it. So let’s wrap this up, Brian. You and I could talk for hours, and there’s still a lot of other things we could chat about. I’m sure we’ll see you around again. Very soon. Um, what is the outlook for you? Like, how is this industry going to look like? Uh, we’ve seen some recent announcements by Airbnb raising fees and getting rid of the guest fees. So obviously evolve is going to raise their fees as well. Just kidding. Um, but, you know, it’s a free pass for OTAs now to think how much dependency we have. And I guess your model remains naive and more attractive as well. But we don’t need to want to talk about it. For me, I want to general outlook for you. We talked about how’s supply going to evolve. We both agreed it’s going to probably stay about the same in terms of split. Uh, from from long tail versus, uh, manage inventory. What other significant changes, uh, and your outlook in the next couple of years, we’re going to see within the STR space.

Brian Egan: [00:51:09] Yeah. So let’s pick a time frame and call it three years. Right. Um, I am incredibly bullish on the industry. And I know that that could sound cliched, and I’m certainly not unbiased. Um, but I wouldn’t have said that three years ago. Uh, you know, and I didn’t I was on the record then, too. So here’s why I’m bullish. One, I think you’re seeing a market. And again, I, I spend 100% of my time on the US right now. So I don’t claim to have the dynamics of, of the, of other global markets down. So take this, uh, as the US analysis, I think we are seeing every sign of stabilization. We went through a massive supply and demand dislocation from Covid and then a massive spike post Covid, as you had, you know, think about everywhere, was everyone was locked up in their houses. Everyone wanted to get out and travel, but they didn’t want to go cross border. They didn’t want to get on an airplane. They didn’t want to go to a city. They didn’t want to be in a hotel with shared amenities. They wanted to drive to a home. Well, that was really good for our business, you know. But on the other hand, it was unsustainable because you were getting, you know, more than our fair share. Multiple years consolidated into one. All the rest. Right. So think about this. If you look at, you know, uh, in the hotel world, RevPAR revenue per available room in the in our world, we usually call it rev per available night. That number is down 38% from its peak in 2021. Wow. That’s hard when you’re selling the widgets you sell as a business every day for 38% less.

Brian Egan: [00:52:45] That’s hard. That’s hard to generate the kind of growth that attracts investment and all the other things we were just talking about. But let’s also step back and say this. That number is up double digits over 19 over the pre-pandemic baseline still. So this is a really healthy market. I mean, if you had if you and I the first time we met, I think that was probably 2013 or 14 or something like that. Right. If the first time we had met, you had handed me a snapshot and said, this is what the market’s going to look like in 2025. You didn’t tell me how we were going to get there. You just said this one’s going to look like. I would say, oh, my God, let me in. That’s that looks like a healthy, exciting, thriving market where we can really go step on the gas and do some damage. Right. And that’s like exactly my view now. It’s hard to get that perspective, because the last 2 to 3 years have been so volatile and so many ups and downs. But I think that stabilization point is here. I think that you’ve seen a lot of shakeout of different models. I think it’s very clear that, you know, for us at least, it’s clear that we’ve got a lane that we own. We know how to innovate in it. We’re proving that we can do that. We’ve launched new products in the last year. You know, we had one model for this whole time, and we went and said, you know what? We’re going to create a plus management plan where owners get that much more support, that much more performance, uh, a suite of different offerings that enhance the value proposition in exchange for a slightly higher management fee.

Brian Egan: [00:54:08] That’s been a wild success. We’re seeing 4,045% attach rates on on the plus product in an activation pipeline. So I just think the world is ready for more. I think we’re ready to regrow. And I’m incredibly bullish. And then you go back to oh, and we’re writing the macro wave of AI. We’re writing what I think this would be the big one. Simon I don’t know when this is going to happen, but the real estate market has been locked up. I mean, we have been in a standoff. We are seeing it in all the data. You know, you have a record low number of transactions. You’ve got a reasonable number of listings on the market, but they’re aged out longer than they ever have been. Uh, the number of homes getting pulled off the market is high. You’re just in a standoff between the seller and the buyer. That’s got to break eventually. I mean, again, 25 years of doing anything will teach you that markets go up and down. Right. And so I think that once that real estate market loosens, I think you’re going to see a wave of new owners coming into this category. Um, and yeah, I just I couldn’t be more excited. I excited. I think this is actually, in many ways, a market that we’ve been working really, really hard to get to ever since kind of 2018, 2019. It’s just been quite a rollercoaster ride in order to get there.

Simon Lehmann: [00:55:24] Thank you Brian. And I think the word stabilization is a good wrap up, but I couldn’t agree with you more. And also through a global lens, certain markets are more volatile than others obviously as well. But I would also support that very strongly. Ai still has an unknown impact also on the side of distribution, uh, which I think is something that everybody should focus on how this is going to impact your distribution, how people search for travel and search for accommodation. I think that’s fundamentally going to change. It’s going to be interesting how Google and and the large OTAs deal with that. Uh, my children, they don’t even search on Google anymore. Um, which is quite interesting as well. So that’s definitely going to be uh, having some impact as well. But hey Brian, I really want to thank you for being part of SDR Global Unlocked. Uh, today on this episode, you’ve given some great nuggets away. And, uh, I wish you a fantastic, uh, season and, uh, and continue growth. And hopefully we will see your business, uh, sometime more internationally. Uh, more than happy to.

Brian Egan: [00:56:32] Simon, thanks so much for having me. It was great to reconnect with you.

Simon Lehmann: [00:56:36] Thank you. That was SDR Global Unlocked, where we say what others want. If you got value from today’s episode, send it to someone who is still playing it safe. Follow the show and get more global insight at Angel Telecom, the globally recognized SDR consultancy I founded, and that proudly brings to you this show. More bold conversations are on the way, so stay tuned.

How Visual Storytelling Builds Stronger Vacation Rental Brands with Marissa Galle of Click Media

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In this episode, Alex & Annie are joined by Marissa Galle, founder of Click Media, to explore the real impact of photography, video, and social content on brand perception and booking behavior.

Marissa shares how vacation rental operators can move beyond generic listings and start using visual storytelling to connect with guests, stand out on OTAs, and bring more personality into their marketing. From FPV drone shots to content repurposing strategies, she breaks down what works and why.

We cover:

  • What “visual storytelling” means in a modern vacation rental business
  • How to turn property photos into content that inspires trust and excitement
  • The biggest mistakes operators make with social media and video
  • Why showing your team is just as important as showing your homes
  • How Click is making it easier to access high-quality media services at scale

If you’re looking for fresh ways to strengthen your brand and drive more direct demand, this episode is packed with practical ideas to help you do just that.

Connect with Marissa:
LinkedIn: https://www.linkedin.com/in/marissagalle/
Website: https://letsgoclick.com/ 


Transcript

Alex Husner  
Welcome to Alex & annie: the real women of vacation rentals. I’m Alex, and I’m Annie, and we are joined today by Marissa Galle, who is the founder of Click Media. And today, if you’re not watching on YouTube, you definitely should, because we are the ladies in orange, and Marissa is always a lady in orange at these shows. But it’s so good to see you, Marissa,

Marissa Galle  
thank you. It’s really nice to be here. Thank you for that.

Annie Holcombe  
So Marissa, we got to meet you at the women’s conference back in Charleston in August, and it was great to finally meet you, but we didn’t get a chance to spend a lot of time with you, so I don’t know a lot about you and your background. So I thought before we got started, you could introduce yourself to me and our guests, tell us a little bit about your your history and what brought you to start. You to start this company.

Marissa Galle  
Yeah, so I’m Marissa and I started click real estate photography. I’m actually the CEO of click real estate photography. We started this company, actually first as a video production company in 2018 in Las Vegas. So my husband and I, we met in Belgium, and he had this wild idea that he wanted to move to the US. And I was like, Okay, why not? Let’s just, let’s just try this, you know, let’s, let’s give it a year. And so, yeah, we moved to Vegas. We started our video production company, 2425 media, and a year later, like when we get our visas and everything ready, covid hits, and it hit, yeah, so we were a startup company, and what do you do? Then in 2023 we we pivoted all our whole idea of our company, and we moved to Orlando, where we started, where click was born, and where we actually started working together with costuilla vacation homes. So Frank started photographing all their properties. I already did their marketing, so their social media management, so I already knew Dennis, and that’s how everything, everything actually started. Yeah, wow.

Alex Husner  
I didn’t realize I knew you were from somewhere overseas, but I didn’t realize it was Belgium. But that’s also very interesting, because that’s where Dennis is from. How you met, or was there a connection before?

Marissa Galle  
Yeah, so Dennis and Frank, they knew each other from Belgium. Frank was in the media industry, and Dennis run a company where they where they print brochures,

Alex Husner  
and a couple times

Annie Holcombe  
and you chose, Vegas. Isn’t

Speaker 1  
that amazing

Annie Holcombe  
alternative reality?

Marissa Galle  
Yes, it gave a good connection. We already traveled to Vegas for vacation, and Frank came there a lot because he was in the media industry. He was a TV producer and a host in Belgium, so he knew the area and it is the place to be for video productions. Like it was close to La it was easy for him, like he worked together with Warner Brothers, for example, so it was easy for him to travel back and forth to LA to get those jobs done. Yeah, yeah, that’s why we picked Vegas. And, you know, we’re used to having red carpets and everything in Belgium because of Frank. So Vegas was kind of our, you know, it was the closest to our

Alex Husner  
lifestyle. Wow, that’s so cool. Well, and that so now you guys move to Orlando, which, I mean, Orlando is also not just like a run of the mill place, either. I mean, you know, not quite as the same hustle and bustle as Vegas, but also pretty, pretty busy area.

Marissa Galle  
Yeah, yeah. We love the theme parks here, and like the vacation rental industry, it’s, so big because of that, and that’s actually the best decision we made in 2023 to come over here and not just let the business fail, but really work for it. And we had to start from scratch again. Wow, yeah. So we already did that when we arrived in Vegas, and then we came here in Orlando, and we just had to start all over again.

Alex Husner  
Wow, wow. Well, you guys have done an incredible job. And I remember, I met you last year for the first time at favor in Orlando, and didn’t really know you guys there, but I saw saw you, and then I saw Frank, you know, running around taking pictures. Now, actually, I was on stage moderating a panel, and his drone video, like it came from the back of the room, and I thought it was gonna just like, hit me right in the face. And I was like, I don’t know what’s going on right now. Obviously, he knew exactly what he was doing. He was not gonna, not gonna hit me, but he did. He did such an incredible job. I remember watching the video of that event afterwards, and it was a great event. But you guys really know how to tell a story of an event and really just showcase, like capture the energy, you know, show, show the fun, show the interesting moments. And that’s really been something that’s been lacking within our industry, at most conferences, I would say there’s just, you know, there’s not enough of really being able to see what happened. And. And you know, that’s obviously what led you to to vrma, where you’re going to be back in Vegas. And by the time this airs, it will have already actually happened. But there’s, there’s so much that can be, you know, understood better when people can see things visually through video. And I love what you guys have done for the industry. You were at DARM, also you did a wonderful video for boom, when we won the battleground, that was super cool. I mean, you guys are very, very creative, so you’re a welcome addition into our conference.

Marissa Galle  
Yeah, yeah, yeah. It’s actually all Frank, you know, he’s so creative, and he has it all in his head, and he knows exactly how to film it and how to make sometimes from something boring, just Yeah, they’ll make it entertaining and make it look fun. And that’s what they want on those conferences. That’s why they all start asking us, like, hey, we have all these things going on, like, like, DARM, they had fireworks, and they have all the good food and everything. But if you don’t capture it, then only the people that were there know about it exactly. Yeah, you also want to bring the people there that you know. You want to create a FOMO like the people that were not able to make it. They they want to make it next year. So, yeah, he’s, he’s really good at that. I’m really happy that we can do this team together, and we can, we can build a company that we both love,

Annie Holcombe  
yeah. So you, you started this out as, like, real estate stuff, right? So was it just to help realtors, or was this also within the rental side of things?

Marissa Galle  
So I was a realtor in Las Vegas there, I actually noticed that it was really hard to find a photographer that knew what he was doing, and I started asking Frank, like, Hey, can you take my photos? But of course, he has a background in video production, and that it’s not the same as photographing and making videos of properties, right? Yeah, so the first year, it was a little trial and error, but we, you know, we did it, and eventually he really listened to to what the client wanted. And we just, we just, you know, every feedback that we got, we just kept on changing it, changing it, changing it. That’s why we also tell our clients, like, hey, we will edit your pictures until you are happy, or we will edit your video until you are happy, because you’re paying us to get something that you want. It doesn’t have to be, you know, we have our own style. We we want to have everything bold, but it’s still the client that needs to like it. So we just keep on going until our client is happy.

Alex Husner  
Yeah, yeah. So as far as what you do for vacation rental companies? Now, obviously, you got a really good footing in Orlando with casiola and I’m sure many others in that area, but our property managers hiring you to come do their you know, pictures when they get a new rental on their program, virtual tours like, what’s, what’s the whole offering look like?

Marissa Galle  
We have a really close connection with a lot of property managers now here in Orlando, and it’s mostly going to start with pictures. So they all want to have interior, exterior photos of their properties, and then they’re going to look okay. How can we stand out in this market? Like the pictures are already great, but we want to have video. We want to have 3d tours, for example. And our strongest point in this is that Frank has his video production background so that he is able to create this video. So a lot of other real estate photography companies, they’re really good in making pictures, or, like, learning how to use the Matterport camera. But that video aspect is really something different, that that makes us the strongest in our market, in Orlando, that now everything, everyone wants to pivot to social media, they want to have reels and want to have videos. So that is that’s going to be the most, yeah, the core services that they that they’ll schedule. So

Annie Holcombe  
what are you seeing in terms of, like, I guess creativity within videos. You see people like, I’ve seen the matterports, and I’ve seen people who just kind of do those walk arounds with things, and it’s kind of like, you know, that’s nice, but the homes in Orlando, so many of them, they’re big, and to try to really show, showcase how big they are. I know some of those homes, like, just, you walk in, like, the main room, the ceilings are 20 feet tall, and they’re just, they’re just huge. And so how do you how are you guys differentiating yourself from other people that do video to, like, make them fun and captivating and really tell the story of what some of these homes have to offer?

Marissa Galle  
Well, it’s going to be our editing style. So the way how we film the property and then edit it afterwards, we try to make we try to put a lot of dynamic in it. And we also have an FPV drone that is actually the drone that you saw on the conference. It’s the little orange one that you. Thought that was always gonna hit your

Alex Husner  
head. It looks like an alien coming at you.

Marissa Galle  
So that drone is, it’s like, what kind of goggles on? So he has to hide in a closet somewhere. Yeah, it’s really cool to see, like is flying first person view through the property. So it’s really going to show you how how this property is, yeah, we make this, this nice combination of video with some of those shots to make it more dynamic. Like, if there’s a bunk bed and it’s, for example, a cave, the bunk bed is built into a cave or something, then the FPV drone can actually fly through the smallest holes, to just show them, like, Hey, this is not just bed. It’s not just a cave. But it’s also, wow, that’s

Alex Husner  
cool. So cool. Yeah.

Annie Holcombe  
Kids love that, because all the kids are like, I want to go down that slide, or I want to see what’s in there. And now they really get to experience

Marissa Galle  
it before they even get to the house. Very cool, the biggest house that Frank did, 23,000 square feet.

Alex Husner  
Wow, that was a long day of shooting. A lot of closets died and

Annie Holcombe  
oh my gosh,

Alex Husner  
yeah, wow. Well, I mean, you know, I think we all know this, and most people, most people do. But I mean, your picture quality, your video quality, it makes a night and day difference in terms of your performance, in terms of your revenue. I mean, it really is, is incremental as far as what you can achieve when you have the right, you know, media assets, to promote these properties. But I know in my days with running the company I was with for many years. We had different photographers. We use some of the different 3d tours, and it’s like, you know, it was, it was good for what those days were at the time. But when we started kind of upping our game, which was just kind of basic, as far as things are nowadays, the step below that basic was the property manager going out, not even on an iPhone, on whatever their flip phone was, and taking pictures of the property. So the pictures were terrible in the early days. And it’s like, I’m seeing kind of the evolution of, like, all right, there’s the professionalism kind of got there. And you still see on Airbnb plenty of listings that they still have not even gotten to that. But I think you know, the challenge that most managers face now too, especially, and this is why it’s interesting that you do social media with it is, okay, we’ve got these beautiful pictures of these properties, but it’s boring to go to a property manager’s social media page and just see pictures upon pictures upon pictures of properties like those posts get very little engagement. And you know, it’s typically done as a way to appease a homeowner, because they’ve reached out and they’ve said, you know, our bookings aren’t good. I need you need to push me, and they get pushed on social media in an email blast. But does it really do anything? You know, typically not. Doesn’t really move the needle a whole lot. No. But where property managers get stuck is okay, they’ve got these, maybe even video. They might have video. They might have great pictures, but they don’t have anybody to then edit it. And they’re not making, you know, interesting reels. That is like telling a story of why you would not only stay in that home, but why you would visit that destination, why you would stay with that company. And the companies that you know, I know that are really leaning into that they their social media is making an impact, and it’s like that that actually does drive bookings. And you’ve got to really tell that story, but it’s not easy if you don’t have the right people and expertise to be able to do it. So I’m curious how that works. Of like, what those services are once you’ve taken the pictures, you’ve done the video, like, what sort of assets, are property managers able to also get to promote the

Marissa Galle  
properties as a social media manager for seven years for casiola Already, I got the expertise, let’s say, into what does a property manager need to post? What do they need to talk about? Because it’s, you know, you have all these nice properties, but sometimes you also want to with a vacation rental. You actually want to sell the dream of the property. So you want to sell the vacation so we always tell them, like, hey, maybe it’s an idea to get people in there. Like, get, you know, make, make a video with some kids that are jumping in the pool, stuff like that. So once we have all the content for the client, they can actually come to us and choose a package where we help them create their social media marketing like they can choose their their platforms where they want to post them, and then I will have a monthly call with them, see like, Hey, what are you looking for? What do you want to talk about? Because it’s not only your property, it’s also what is happening around your property. Like in Orlando, it’s easy. You have Disney, you have sea world. Now it’s I’m already thinking about Christmas, because we’re already marketing Christmas, right? Now, yeah, so that is something we also want to we also offer our property managers like, Okay, you have all this content. Give it to us. I’ll make a schedule with you, and we make sure that everything goes online and that we create engaging content for

Annie Holcombe  
you. Do you have, like, a best practice for property managers? Say, if they’re just getting started, because I think that sometimes you see they flood it, and maybe they’re not seeing impact, so they stop it. And, you know, it’s consistency, like Alex and I’ve learned with the podcast, consistency is really key. But I think that some people get overwhelmed by it because they’re not seeing an impact. What it’s like for you? Is there a best practice of like consistent posting, and how long it should take before they start to see other click throughs to their direct site or something impactful that would be moving the needle for them.

Marissa Galle  
I always say it can take at least three months until, even especially if your page starts from from like Scratch, it can take up to three months until you’re really up and running. And like you say, consistency is the key. So I always tell my clients like that, posting like three to four times a week is definitely enough, but make a good mix between a static picture, but also an entertaining video and also, like I just said, not only your property, but maybe also, like a video from the surroundings. Is there a community pool? Is there a park close by? So that’s also something we do. They can book us for a community video, a walkthrough video, like, from the property to the community, for example, or like, even a property manager that that that talks and, you know, there’s an introduction about the property. Who knows the property best, and the property owner themselves, right? Yeah, yeah. So, yeah, I think it’s, it’s a good mix of that. And just keep the, keep the people entertained, like, try to come up with, with funky stuff.

Alex Husner  
Yeah, exactly. Yeah. We actually, we just got back from Italy last week, and we did a presentation, the same one that we did when we were at the women’s conference back in August. But one of the points was in trying to get away from losing the search visibility because of how SEO has changed, and AI and everything else, like, what are the ways you can really improve your conversion optimization, both of getting properties and then also getting bookings. And one of our tips was show your team, I mean, make a really robust About Us page, and show who you are, and like, what your story is. And you know why, why you do what you do. And there’s no better way to do that than video. And we showed an example of one of my clients, and Hilton had the video that we did for them. And it’s like, you know, if a potential homeowner is researching your company, it’s really nice to be able to go on and actually not only see the person, but listen to them speak, and, you know, understand what the values are of the company before you even reach out. But it’s definitely an area that most companies really don’t lean into, because one, you’ve got to have somebody that can kind of orchestrate it. You’ve got to figure out who’s going to film it. You know, they’re not all companies have a CMO or even a marketing director. So it’s like it’s out of reach in a lot of ways. But I think, you know, Colin, you guys probably would make a lot of sense. Definitely

Marissa Galle  
know what to do. And it’s like you say, like today, this day is so digital, it’s also AI. I think a company still needs that personal touch. Like, don’t forget about your personal touch, yeah, like showing your team and really talking to your guests talking to your owners too, because your owner also knows how they want you to sell their property, like how you know how they what guests they want and what they want to what they want to do with their property. So yeah, that personal touch is still really important, even in this AI tech driven world? Snap, yeah, absolutely.

Annie Holcombe  
You brought AI up, and I was actually going to ask you about that. I’m working with a property manager in Indianapolis, so not like a traditional vacation rental market, more of an urban market, but they have a lot of dynamic events, you know, conventions, big sporting events. They’ve got the Indianapolis Colts, there’s indie speedway. Is there that, you know, they have a lot of, like, car races and stuff. And one of the things that we were talking about was, how can they create kind of something, that they become the expert, like the expert of the area? There’s a lot to tell, but it’s on a traditional market. And we were talking about like, you know, making sure that you have a lot of content out there so AI can pick it up. So do you see AI being able to pick up the video content down the road? Because I know that there’s AI is creating videos, but is there something that it can go through the internet and find the videos as well, and the photos and things?

Marissa Galle  
I’m actually not sure. Yet about videos, I do know that it can read pictures for sure, because I use it a lot. I use it a lot for, for example, social media management, if I have a picture, I just upload it in AI. And I, I ask, AI, like, what? What do you see on here? How would you sell this? What? What would you say, like, you know, things like that. But I think there’s, there’s definitely a way that that video will be picked up with AI, or it will definitely come soon in the future too.

Alex Husner  
Yeah, and I feel, you know, there’s definitely platforms out there that make it way easier to edit video, but you know, I’m also hoping in the future, there are more that just make it even easier. I think you for sure, need someone with the style and the direction that you guys offer, but there’s a lot of the tools that I’ve played around with, they’re okay, but it’s like, it’s still pretty big learning curve to get really used to them, and at the end of the day, it’s easier for us to send it to our editor, so we don’t end up doing it. But yeah, it’ll be interesting to see you know, how what other tools come out, and how easy it really makes things, I guess. But was curious, too. I mean, I’m sure just this conversation has got people thinking of, okay, well, if I wanted to do a video about my team or wanted to get better videos for my properties. This sounds great, but how do I work with you and Frank, knowing that you’re based in Orlando, so how does that work for clients out of the area?

Marissa Galle  
So Frank travels a lot, especially like, if it’s corporate videos, or if we can, like, you know, bundle things together, make it a project, because mostly those companies. They don’t want to have just one property. They they have this idea, they have this marketing plan, and they want to have it worked out. So if you can work that out together with them, Frank flies out easily, like he’s gone every month, every month, like he was just in New York after Verma, after Vera May. He’s in San Francisco. He’s also, well, Miami is a little closer a bit, so he flies out. But we also have people, because we lived in in Vegas, we know a lot of people that you know have that know video production, if it’s like smaller objects, and it’s sometimes easier for us to just reach out to the people we know that are closer in the area, or we look for someone new, and we just see, like, Okay, what is your style? Do you fit our click DNA? And can we work with you? We will always make sure that we can, that we can manage it, that we can help the property manager, even if it’s far, far away. Yeah, gotcha. We still do jobs in Europe, even so, oh, really? Go to Europe? Like, yeah, it’s a long trip. Like, if Frank is why in the US, that’s nothing, but if he has to go all the way to Europe, but yeah, he had a TV station there. So he knows a lot of people in the industry, so it’s easy there to just send someone out. But I think it was in August he flew out because he was a host of an event. I don’t know if you know, but Frank was like, kind of the Jackass in Belgium show.

Alex Husner  
MTV, show, right?

Marissa Galle  
Yes, yeah. So yeah, in Belgium, they know him like that, so they still want him for that. So if there’s that really fits that kind of freakiness, they just what convention was it that he flew over? I think it was, I think it was a woman come the woman conference, actually, that he flew to Belgium, and then for one day, and then he came back, and then it was the woman, oh, my god,

Annie Holcombe  
wow, after flying to Italy, and it taken three days to get there for me, I can’t even turn around. That’s crazy. Yeah,

Alex Husner  
he worked on some other big name shows as well. I think he mentioned to us in Charleston, I’m trying to think what it was, but what wasn’t there another big national TV show that he was he worked on.

Marissa Galle  
He wasn’t the first big brother.

Alex Husner  
That’s right, big brother, yeah, I

Annie Holcombe  
just remember he told us that he’s like, he’s like, you know, the show jackass. He goes, I was the Jackass of Belgium, but don’t call me the jackass. Like, I’m not the jackass, but it’s not

Alex Husner  
me anymore.

Marissa Galle  
Yeah, they called him freaky Frank.

Alex Husner  
He’s like, the sweetest guy in the world to be like. He’s so great.

Marissa Galle  
Yeah, I actually met him, and he had his own TV show, his own production station, production company there. And that’s how I met him, because I was participating with Belgium, so I had. To be in all those red carpet events, just, you know, you know, sell myself. Let’s say yeah, yeah, wrong, but yeah, and that’s, that’s how we that’s how we

Speaker 3  
met. Wow, that’s so cool. We had

Marissa Galle  
this the same dream, like living in the US, and we just did it. Yeah, ups and downs, but now, click is almost three years now, and it’s going well, and our focus is expanding to so many cities as possible, so we can help as many property managers as possible.

Alex Husner  
Yeah, well, I have no doubt that

Speaker 1  
you’re gonna do it.

Annie Holcombe  
You have a, like a target size property manager that you work with. So like, do you work with somebody who maybe is just starting their business all the way up to, obviously, like a dentist at casiola who has hundreds of units, just anyone, anybody who’s interested,

Marissa Galle  
anybody who’s interested, because we also do a lot in in real estate, because I was a realtor, and I know how hard it is to find a good photographer, and we want them to be able to build a brand to keep that consistency. So that’s also why we want to be in different markets, because a realtor also has properties in different areas. The property manager, he can be in Miami, he can be in Orlando, he can be in Tampa, and that’s only Florida. Like, oh yeah. We have a robot, for example, too. We’re taking over the island there. We have a good photographer there. And it’s he’s actually coming to Vera, Ma, so you got to meet him. Oh, fine.

Alex Husner  
This is going to air once we get back, but maybe just tell us a little bit about what you’re going to be doing out there and just kind of what the plan is, in case. I’m sure there’s plenty people that that listen, that won’t necessarily be at the show, but just kind of to hear what you guys have going on.

Marissa Galle  
Yes, so we are the proud media partner this year of your May, and we’re gonna have our booth like we have on every conference, and everyone will probably recognize because it’s bright orange, yeah. But next to that, we’re also gonna operate the headshot booth so everyone can just come by get their headshots taken. I’m not sure where it is exactly, am I out of my head? But I can definitely give you the boot number. If people are looking for that, we will also post that on our social media. And then Frank is going to be running around with his camera. We don’t have a drone permission to fly there. They’re really strict in Vegas, drone flying around this time. But yeah, Frank is gonna, gonna cover the whole conference. Like, really try to get the flow, get the vibe out there, like happening there. Keynote speakers will be highlighted in there, the fun events. Hopefully. I heard there was horseback riding and things like that. Oh

Alex Husner  
yeah, I signed up for that, and I just found out that

Annie Holcombe  
Sunday. So no, it’ll

Alex Husner  
be, it’ll be. So he’s actually, he’s gonna be out there taking video of that.

Marissa Galle  
Well, I hope he will be. I’m actually still waiting someday. So, yeah, I think, I think as if we can get the entertainment stuff that that happened, the friends or like, the parties in the evening, that’s actually what makes those conferences, oh for

Alex Husner  
sure, yeah, yeah, yeah. I

Annie Holcombe  
think it’s so fun, though, when you look back, especially at a large conference like Vegas, like you don’t remember some of the stuff that happened because it went by so quickly, or maybe you didn’t get to a specific party, or you like, you saw somebody, but you didn’t get a chance to talk to them, and you’re like, Did I see them? Did I not see them? Like, having these recap videos is always, like, fun. It’s kind of kind of makes me think of like, you know, the end of the school year when they do those wrap ups of, like, all this stuff that was fun that just so it kind of supersedes all the, like, monotonous work that you had to do. It’s, like, all the fun parts of it, and you’re like, Oh yeah, that was actually a great time. And I really enjoyed it. So

Marissa Galle  
like, on the on the woman’s conference, I like the 80s party. Oh yeah. Was the 90s?

Annie Holcombe  
90s? Yeah, yeah.

Marissa Galle  
Just had an 80s one. That’s probably why 80s, they’re all the same, really, it makes it just, it makes it Yeah, and that’s for sure, yeah. That’s why you need to do what you property to, like, come up with something that’s, that’s fun. Like, yeah, he once had a client, and he was like, Hey, how would it look like if he would have, like, a mascot or something, giving a tour in the house. Oh, I love it. We’re with you. Come on. When can we start crazy ideas that that’s, that’s what we’re all for, like, we want to be bold,

Alex Husner  
yeah? Yeah. I mean, there’s normal stuff. Of course, there’s so many properties out there. I think that’s the main takeaway. Is like, there’s so many properties out there, especially if your main source of business is the OTAs, and you’ve got to do something to differentiate and whether that’s showing your team, whether it’s a mascot, whether it’s just using video way more than your competition. Because most of the competition is not using video. You know, those are, as those are the companies that win their market. So

Marissa Galle  
yeah,

Annie Holcombe  
so what is, what’s on the horizon for you guys? So you’re growing, you’re getting into more markets. Is there any new initiative that you’re going to unveil in Vegas, or maybe jump into next year that you’re not doing right now? Well, I wanted to

Marissa Galle  
introduce in Vegas that we’re actually gonna brand everything under click. So as I said in the beginning, we have 2425 media, which is a video production company that’s now going to become click media. Then have click photography, which is going to be the real estate and video vacation rental part. But next to that, we’re also going to launch click social or like this social hub, where we’re really going to make it easy for property managers to just like their as they’re booking services that they also can just book marketing services on our platforms. So right now they have to contact me in person and email me, but we want to make it all online. I’m really excited about that part, actually, because that’s even more what I was already doing. And I’m going to incorporate that a little bit more into click, but I’m afraid I’m not going to have it 100% ready by Vera may, because it has been so busy. But yeah, we want to help companies a little bit more with branding, like their head shops, their corporate videos, things like that, and make it easy to book it with us. Yeah, you want to do it all online?

Alex Husner  
Yeah? Oh, that makes it. That makes it easy. I already have a couple clients that I work with that I’m my wheels are turning and I will, yeah, I’ll be reaching out to you after, after we end this episode, but let me know, I love working with you guys. You guys are the best, but yeah, well, this has been long overdue. I know we had had you on the schedule earlier this spring. We had some scheduling conflicts, but I’m so glad that we got to have you on and especially at this time of the year, this is I think the conference is going to be amazing for you guys, and can’t wait to see the video of it afterwards and just how you capture that essence. But if anybody wants to get in touch with you, Marissa, what’s the best way to reach out?

Marissa Galle  
Well, I would say we do it all online. Go to a website and everything is up there. But if you want to contact me in person, it’s going to be my email. Marissa, at Let’s go click.com the website is indeed, let’s go click.com Yeah, it’s already a small part of our rebranding that now it’s not click real estate photography anymore. It’s, let’s go click. Yes,

Alex Husner  
I love that. I love that, especially when everybody’s trying to compete to get clicks right now, and it’s more complicated than ever from a marketing standpoint, and anything that you do. So, yeah, great, perfect, awesome. Well, if anybody wants to get in touch with Annie and I, you can go to Alex and Annie podcast.com and until next time, thanks for tuning in. Everybody.

6 Common Agentic AI Pitfalls and How to Avoid Them

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Avoiding Agentic Ai pitfalls

Hearing horror stories about agentic AI implementations? Your company needn’t be a victim.

There’s a vast gap between agentic AI’s promise and the current implementation reality. As vendors rush to rebrand existing automation as “agentic” and marketers scramble to avoid being left behind, organizations can easily stumble into predictable traps that waste budgets and damage brands. 

While researching Agentic AI, decoded: A practical guide for marketers, I learned about the approach and mindset that successful agentic AI implementation requires. Check out the full report for details; in the meantime, I’ll share six potential pitfalls that can derail agentic AI initiatives — and how to ensure your team avoids them.

Automation posing as agentic AI

The pitfall: Vendors are applying “agentic” labels to traditional, rules-based automation. You think you’re buying adaptive intelligence that learns and improves, but you’re getting glorified if-then scripts that break when scenarios drift outside predetermined parameters.

How to spot it: Ask vendors to walk through a specific decision the system made recently. If they can’t show you how it reasoned through trade-offs or adapted to unexpected inputs — if every explanation sounds like “when X happens, we do Y” — you’re looking at automation, not agency.

How to avoid it: Demand proof of autonomous decision-making in your proof-of-concept. True agents should demonstrate goal-oriented reasoning, meaning they work backward from objectives to determine actions, not forward from triggers to predetermined responses.

Characteristics Of Agentic AI 1

Data-set creep

The pitfall: Agents start accessing and processing data fields you never intended them to touch. For example, a customer service agent could start pulling from internal salary databases to “personalize” responses. Or a content agent could scrape competitor websites without authorization.

How to avoid it: Implement field-level access controls before deployment, not after. Create explicit data boundaries in your agent’s configuration and use data loss prevention tools to monitor what agents access. Maintain audit logs of every data source touched. If your vendor can’t show you exactly which fields an agent can access, that’s a red flag.

The integration iceberg

The pitfall: That “quick win” pilot turns into a six-month data engineering project. Organizations consistently underestimate the work required to connect customer data platforms, normalize formats across systems and maintain data quality standards that agents require.

How to avoid it: Map your data infrastructure gaps before selecting vendors. Agents need unified customer IDs, consistent event schemas and real-time data streams. Budget three to six months for data preparation and consider starting with single-channel implementations where data complexity is lower.

Governance by misstep

The pitfall: Imagine a team deploying agents that can autonomously publish content, adjust pricing or message customers — then scrambling to add controls after the first crisis. When Anthropic and Andon Labs put an AI model (dubbed Claudius for Anthropic’s Claude) in charge of an office snack set-up – allowing it to manage inventory, set prices and interact with customers – the AI did well at some tasks. However, it failed to adjust pricing based on demand and frequently offered discount codes and free merchandise. It even hallucinated a Venmo account and told buyers to send their payment to it. Oops!

How to avoid it: Build kill switches and rate limiters into initial deployment. Every autonomous action requires a maximum boundary (in terms of spend, volume or frequency) and a human-reviewable audit trail. Implement staged rollouts where agents operate in shadow mode first, with their decisions logged but not executed, until you’ve validated their judgment.

The skills gap issue

The pitfall: Organizations buy sophisticated agentic platforms, then realize nobody knows how to set outcomes for optimization, interpret agent decisions or troubleshoot when things go wrong. The technology sits underutilized while teams wait for “AI experts” who don’t exist in the current job market.

How to avoid it: Identify who will own agent operations before purchasing. This isn’t a part-time responsibility — you need dedicated staff who understand both marketing objectives and AI operations. Invest in upskilling current marketing ops teams. Start with vendor-managed solutions or training if you lack internal capabilities.

Traditional Vs Agentic Mindsets

Elusive ROI

The pitfall: Teams celebrate time savings and efficiency gains while overlooking the fact that agents aren’t actually driving revenue. You’ve automated bad tactics to make them occur faster.

How to avoid it: Measure revenue contribution and CLV, not just operational metrics. If your agents are perfectly executing a flawed strategy, you’ve only accelerated your way to poor results—set business outcome KPIs from day one, not just efficiency metrics.

Moving forward

You can avoid these pitfalls by using proper evaluation frameworks and implementing approaches in stages. Before deploying agentic AI, assess your organization’s readiness across data, skills and governance dimensions. Start with narrow, well-bounded use cases where you can validate performance before expanding the scope.

For a comprehensive framework including detailed evaluation checklists, maturity models and vendor assessment criteria, download MarTech’s new report — Agentic AI, decoded: A practical guide for marketers.

2026 Vacation Rental Industry Outlook: Staffing and Revenue Pressures Are Top Concerns

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key data dashboard

As the short-term rental industry looks ahead to 2026, new research from Key Data reveals that property managers are entering the year with a cautious but determined mindset.

According to Key Data’s 2026 Vacation Rental Industry Outlook, nearly three-quarters (73%) of property managers say staffing and revenue pressures are the biggest barriers to hitting their business goals in the coming year. The findings, based on responses from 244 professionals overseeing more than 43,000 properties across the U.S., paint a clear picture of an industry balancing optimism with operational strain.

Regulation and Operational Pressures Remain Top of Mind

Regulation continues to weigh heavily on short-term rental operators.

  • 42% of managers expect local or state regulations to impact their ability to meet 2026 targets.
  • 47% report facing strict permitting or licensing requirements, leading to higher compliance costs, operating caps, and ongoing uncertainty as local ordinances shift.

Meanwhile, operational and staffing challenges dominate daily management realities. Recruiting and retaining qualified staff, from cleaners to guest service teams, remains a top operational pain point. Combined with softer revenue growth and evolving market dynamics, many managers are focused on doing more with less.

Marketing, Distribution, and Technology Shifts

Beyond staffing and regulation, 23% of managers cited marketing and distribution pressures as an ongoing challenge. This serves as a reminder of just how competitive the booking landscape remains.

Interestingly, just 8% of respondents viewed technology or insights as limiting factors, underscoring a growing shift in perception: rather than seeing tech as a hurdle, most operators now view it as a key enabler for growth, efficiency, and smarter decision-making.

A Market Focused on Efficiency

Despite mounting pressures, a majority (60%) of property managers still expect modest revenue growth in 2026. To achieve that, operators are zeroing in on efficiency and operational excellence as their top strategic priorities ahead of marketing, guest experience, or portfolio expansion.

Nearly one in three managers stated they review market data weekly to guide pricing and performance decisions. This commitment to real-time insights reflects a maturing industry that understands the value of data in protecting margins and staying competitive.

A Market Bracing for Tougher Conditions and Steady Growth

“The data makes clear that property managers are feeling the pressure as they head into 2026,” said Quinn Monescalchi, Senior Data Analyst of Marketing & Insights at Key Data. “Staffing shortages, revenue concerns, and regulation are weighing heavily on the sector. What we also see is a shift in priorities: managers are putting operations and efficiency ahead of expansion, and leaning more on data to make decisions. It reflects a market that is bracing for tougher conditions while still looking for steady, sustainable growth.”

The full 2026 Vacation Rental Industry Outlook, including deeper insights into regional trends, operational benchmarks, and data-driven strategies, is coming soon. Visit Key Data’s website to learn more and follow Key Data on LinkedIn to be the first to access your copy of the 2026 Vacation Rental Industry Outlook. 

Hospitable Launches Owner Portals to Give Managers Control and Owners Confidence

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hospital owner manager

Property management software Hospitable has launched Owner Portals, a feature designed to reshape how managers and owners collaborate. For the first time, property managers can offer owners instant visibility into their property performance while maintaining full control and eliminating the repetitive admin that has long weighed on the relationship. 

For managers overseeing multiple homes, owner requests are constant. They want to see how bookings are tracking, how revenues are building, and how their properties are performing overall. Without the right tools, that visibility has come at the cost of countless hours spent on manual tasks, like compiling financial reports and replying to emails. 

Now, owners have a simple way to check their properties’ performance without being overwhelmed by features designed for property managers. Each owner receives a secure, personalized login to their portal, where they can view live calendars, occupancy levels, nightly rates, revenue summaries, and professional financial statements. The data is presented in real time and updated automatically, giving owners the clarity they need without adding to the manager’s workload.

The feature also accounts for personal use of a property. When owners block dates for themselves, those stays are clearly marked, excluded from guest communications, and seamlessly integrated into reports and financial records. Preferences for access, cleaning, payments, and commissions can be saved for reuse, making repeat stays simple and error-free.

At every step, managers remain in control. They decide exactly what information each owner sees, tailoring access to individual clients and keeping sensitive details private. The result is a professional, self-serve experience that builds trust, saves time, and raises the standard of modern property management.

Hospitable has designed the portals to be branded, intuitive, and effortless to set up. Managers can grant access with a single click, creating a polished experience for owners while streamlining operations and strengthening relationships.

Owner Portals are the latest step in Hospitable’s commitment to helping property managers run smarter, more efficient short-term rental businesses. The launch follows a series of recent feature releases designed to help property managers professionalize and scale, including automated owner statements, guest vetting, rental agreements, and flexible payment terms.

“Property managers shouldn’t have to choose between growing their business and keeping owners happy. Owners want visibility; managers need control. Owner Portals make both possible without the hassle. It’s about giving owners the transparency they expect while freeing managers to focus on what really matters.” – Pierre‑Camille  Hamana, CEO  &  Founder of Hospitable

Launched in 2016 as a time-saving PMS, Hospitable has evolved into a super app that goes beyond traditional property management, enabling thousands of hosts at every scale to automate guest messaging with AI, optimize nightly rates, simplify rental agreements and deposits, coordinate teams, and confidently launch direct booking websites with built-in payments and property protection.

Hospitable is the short-term rental industry’s premier super app, empowering hosts and property managers to streamline operations, grow their businesses, and reclaim valuable time. Initially launched in 2016 as a time-saving PMS, Hospitable has evolved into a powerful toolkit that goes beyond traditional property management. The platform enables hosts at every scale to automate guest messaging with AI, optimize nightly rates, simplify rental agreements and deposits, coordinate teams, and confidently launch direct booking websites with built-in payments and property protection. Hospitable supports tens of thousands of hosts worldwide, having automated nearly 25 million messages and processed $4.6 billion in reservation income in 2024. For more information, visit www.hospitable.com

The Future of Short-Term Rentals & What Hosts Need to Know

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beautiful vacation rental professionally styled

The short-term rental industry stands at a pivotal moment. While explosive growth promises unprecedented opportunities—with the market racing toward an $8.9 billion valuation by 2026—the landscape beneath hosts’ feet is shifting in ways that demand immediate attention and strategic adaptation.

 At Whimstay, we’ve positioned ourselves at the intersection of these changes as the leading last-minute vacation rental marketplace. Our unique vantage point—connecting spontaneous travelers with property owners looking to fill gap nights—gives us direct insight into the trends reshaping our industry. Let’s explore what they mean for your property’s future success.

Shrinking Booking Windows

One of the most significant shifts impacting the short-term rental market is the dramatic shrinking of booking windows. Travelers are increasingly making spontaneous decisions, with many bookings now happening within days or even hours of check-in. This trend toward last-minute accommodations is driven by flexible work arrangements, unpredictable travel schedules, and a growing preference for spontaneous getaways.

For property operators, this means maintaining higher availability and developing agile pricing strategies that can capture last-minute demand. Properties that can offer instant booking and seamless mobile experiences will have a significant advantage in capturing this spontaneous travel segment.

This is precisely why Whimstay exists. We’ve built our entire platform around the 30-day booking window, negotiating directly with property owners to offer rates that are consistently lower than those found on other major vacation rental sites. By partnering with platforms specifically designed for last-minute bookings, hosts can tap into the growing market of spontaneous travelers while filling nights that might otherwise remain vacant due to the day of the week, season, or unexpected cancellations.

The Experience Economy

Success in 2026’s short-term rental market will depend on delivering exceptional experiences rather than simply providing accommodation. The most successful operators are focusing on unique property features that photograph well for social media, personalized local experiences and recommendations, and seamless technology integration for booking and communication.

Sustainability is Non-negotiable

Environmental consciousness is no longer a nice-to-have; it’s becoming a fundamental expectation. Travelers are actively seeking accommodations that demonstrate genuine commitment to sustainability. This includes everything from renewable energy systems and waste reduction programs to partnerships with local conservation efforts.

Short-term rental operators who invest in sustainability initiatives will not only appeal to environmentally conscious travelers but may also benefit from local government incentives and reduced operational costs.

Off-the-Beaten-Path Becomes Mainstream

Social media and cultural trends are driving sudden, unexpected fluctuations in destination popularity. Travelers are increasingly seeking less-trafficked locations and embracing off-season travel to avoid crowds and find better value.

This trend creates opportunities for short-term rental operators in secondary cities and emerging destinations. Properties that can offer unique local experiences in these up-and- coming areas may see significant growth.

Whimstay’s portfolio spans vacation rental homes across the U.S., Canada, Mexico, and the Caribbean, giving travelers access to both popular destinations and hidden gems. For property owners in emerging markets or off-peak locations, this represents a valuable opportunity to reach travelers specifically seeking alternatives to overcrowded tourist hotspots.

The AI Revolution

Artificial Intelligence is no longer a futuristic concept in travel – it’s rapidly becoming a present reality that will significantly impact how we plan, book, and experience travel in 2026. The AI tourism market is forecasted to reach $1.2 billion by 2026, signaling that this technology has matured beyond experimental phases.

For short-term rental operators, AI presents opportunities to automate guest communications, optimize pricing strategies in real-time, and provide hyper-personalized local recommendations that can enhance guest experiences and drive higher satisfaction ratings.

The convergence of these trends—shrinking booking windows, experience-focused travel, sustainability demands, emerging destinations, and AI capabilities—is creating a fundamentally different short-term rental landscape than existed just a few years ago.

For hosts and property managers, success means embracing flexibility, maintaining high availability for last-minute bookings, and partnering with platforms that align with where the market is heading. By listing on specialized last-minute marketplaces alongside traditional platforms, you can capture the untapped market of off-peak days, last-minute cancellations, and shoulder season travelers—segments that are growing rapidly but underserved by conventional booking platforms. 

The 2025 M&A Playbook for Vacation Rental Management Companies

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The vacation rental management M&A market is experiencing significant shifts in 2025. Already, we’ve seen Awayday taking on additional capital from Ares, Nocturne’s investment partner Gladstone exiting, and, perhaps most notably, Casago acquiring Vacasa. 

Shifts like these are creating both opportunities and challenges. For companies considering an exit, it’s a seller-friendly market with well-funded buyers and more favorable terms. On the other hand, operators committed to independence are facing intensified competition with greater resources and aggressive growth strategies.

With that in mind, here’s what you need to know about who’s buying, what they value, and how to position your vacation rental management company for maximum advantage.

The Buyer Landscape in Vacation Rental Management M&A

There are three distinct buyer types in the vacation rental management M&A ecosystem, each with different motivations, evaluation criteria, and post-acquisition plans. 

Understanding these differences is crucial for sellers looking to target the right buyers and maximize their valuation.

Strategic Acquirers

These are existing property management companies hoping to acquire other similar businesses. They’re looking for synergies between their existing company and yours, evaluating whether you complement their team, revenue management systems, property management systems, or location. While they care about profitability, they tend to look past current numbers and at the potential of the combined businesses.

Private Equity Firms

These financially-driven groups have raised capital to make platform investments in the vacation rental management M&A space. They typically start with acquiring a company generating at least $2-3 million in EBITDA, which then serves as the foundation for smaller bolt-on acquisitions. PE firms are highly focused on EBITDA and growth potential, usually operating on a five-year horizon with plans to grow the business and sell it again.

Owner-Operators

These individuals are seeking lifestyle businesses that they can personally run. They often finance acquisitions through SBA 7(a) loans with personal guarantees, which typically limits them to smaller businesses generating less than $1 million in EBITDA. They end up being the day-to-day operators of the company, taking a hands-on approach to management rather than relying on existing teams.

Transaction Structures in Vacation Rental Management M&A

Vacation rental management companies have multiple exit options available to them, each with different structures and advantages depending on the owner’s goals.

Full Sale (100% Exit)

This involves selling 100% stake in the business, with the structure typically being approximately 75% cash at closing with the remaining 25% in retention payments. These payments are tied to homeowner contract continuity over a 12–24 month period, ensuring business stability post-acquisition. Buyers implement this structure to ensure continuity with the business moving forward, protecting their investment by maintaining key client relationships during the transition.

Majority Recap

Some business owners will sell majority equity (around 70%) while rolling the remaining portion (30%) into the acquiring company, providing immediate liquidity while still reaping the benefits of future business growth. The seller’s success here will depend heavily on their alignment with the acquirer, their business model, and their operating team. It’s also important to clearly define the seller’s role in the business post-acquisition.

Internal Succession

This involves stepping back from day-to-day operations and selling to your management team, either through an ESOP (employee stock ownership plan) or a direct sale. This creates continuity for the business while keeping your management team involved long-term. It also provides an internal succession plan that maintains stability for homeowner relationships and company operations.

Valuation Drivers in Vacation Rental Management M&A

We recently ran a buyer survey at VRNation’s spring conference, asking about the specific factors that drive valuations and influence acquisition decisions. The results paint a clear roadmap for companies looking to build value well before considering a transaction.

Financial Performance

First and foremost, buyers scrutinize how well your business is performing, profit generation, and operational trends. 

They’ll analyze:

  • ADR (average daily rate) 
  • RevPAR (revenue per available room) 
  • Occupancy patterns and seasonality

In the end, buyers want to see not just current performance but trends that indicate future potential.

Portfolio Stability

Buyers scrutinize the stability of your portfolio as a critical indicator of business health and future performance. 

They look at:

  • How well you retain clients
  • Your annual turnover rates
  • The likelihood of losing contracts post-acquisition

High client turnover immediately raises red flags as it suggests relationship weaknesses that could accelerate after acquisition. This stability directly impacts the predictability of future revenue streams, which is critical to accurate valuation models.

Management Team Strength

Your business cannot be dependent on you alone. Buyers want to see that the company can continue to operate effectively after the owner departs, with clearly defined roles and responsibilities distributed across a capable leadership team. That’s why building a strong management team and culture is paramount to attracting the right buyer and maximizing value in vacation rental management M&A. 

Regulatory Environment

Although it’s entirely out of your control, buyers will also evaluate the regulatory landscape, including any restrictions on vacation rental operations. This helps them understand potential risks and limitations to growth. Areas with stable, predictable regulatory frameworks command higher valuations than those facing uncertain or increasingly restrictive ordinances.

Strategic Positioning in a Consolidating Market

In light of a rapidly shifting acquisitions market, rental management business owners must make clear strategic decisions based on their goals and market position.

If you’re a business owner looking to potentially exit your company, now is a great time to consider your options. There’s fierce competition among various buyer types, which often means better valuations and terms — but only for well-positioned companies with strong financial performance, stable property portfolios, and solid management teams.

Meanwhile, companies committed to independence face challenges from newly consolidated competitors with substantial financial backing. As a business owner, you need to figure out how to differentiate your company and defend against these threats. This means solidifying your brand positioning, focusing on homeowner retention strategies, and finding ways to continue growing despite increased competition. Success requires developing specialized market knowledge, creating unique guest experiences, and strategically investing in technology to improve operational efficiency.

Maximizing Value in Vacation Rental Management M&A

Whether you’re planning to sell or stay independent, the time to prepare is now. The vacation rental management industry is changing rapidly, and waiting to react will only put you at a disadvantage. The companies that succeed will be those that start strengthening their businesses today.

If you’re considering selling, first decide which exit path makes sense for your goals — full sale, majority recap, or internal succession. Then, focus on improving the specific areas buyers care about most: financial performance, portfolio stability, management team strength, and addressing regulatory concerns. Finally, working with an experienced advisor who knows the vacation rental industry will help you navigate the landscape and maximize your sale price.

Raincatcher is a national business brokerage and M&A firm specializing in small and mid-market companies. We believe selling your business isn’t just a transaction. It’s a once-in-a-lifetime transition. One that’s deeply personal, complex, and too important to trust to the wrong partner.

Reach out today for a consultation to discover how we can help you find the right-fit buyer for your objectives and sell your business on your terms.

It’s Your People, Stupid

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Am I calling you stupid? Not really. Just grabbing your attention. But let me break down something I see in company after company that, frankly, is a little stupid.

We’ve become obsessed with everything except the one thing that actually drives results: our people.

The Industry’s Love Affair with Technology

If you walk the expo floor at any vacation rental conference, you’ll hear the same buzzwords on repeat: automation, AI, dynamic pricing, channel optimization. The booths all promise higher margins, fewer headaches, and more scalability. I love great tech. I use it. I invest in it. I’ve built entire companies around leveraging it.

But here’s the problem. The industry has become so fixated on technology, data, and revenue management that we’ve convinced ourselves those things are the business.

We’re tracking RevPAR to the decimal. We’re monitoring conversion rates in real time. We’re running weekly pricing syncs and A/B testing guest emails, yet when it comes to hiring, onboarding, and leading the people who make it all happen, most operators are winging it.

We’ve built entire dashboards to measure everything except the humans using them.

And I get it. Over the past 35 years, I’ve founded 16 companies, most of them in the vacation rental space. For more than half of those years, I did the same thing everyone else does: obsessed over systems, structure, and strategy while underestimating the single biggest variable, the people running those systems.

I’m a technologist. A nerd. I love automation and efficiency. But if there’s one thing I’ve learned the hard way, it’s this: you can’t build a world-class company without a world-class People Stack.

Your People Stack is the organizational counterpart to your tech stack. It’s the structure, alignment, and communication system that determines whether your team actually functions as designed. You can have the most advanced tech in the world, but if your People Stack is weak, your company will always be playing defense.

Don’t wait as long as I did to figure that out.

The Blind Spot: People Still Drive the Machine

Here’s the dirty little secret: every single company in this industry lives or dies by its people. Always has, always will.

And yet, most companies treat hiring and team development like a necessary evil. Something to rush through when someone quits, not something to design, measure, and optimize like any other system.

We’ll spend six months evaluating which property management software to use, but we’ll hire a general manager after a single “good vibe” interview over lunch. We’ll pay consultants to tune our pricing algorithm, but we won’t invest in leadership training for the people actually running the business day to day.

If that’s not an imbalance, I don’t know what is.

And here’s another one I hear all the time: “People don’t want to work anymore.” Really? Maybe they just don’t want to work for you. Maybe you haven’t inspired them, aligned them, or incentivized them the right way.

The truth is, most people want to contribute, grow, and be part of something meaningful. If they’re not showing up that way, it’s not because they’re lazy. It’s because leadership hasn’t given them a reason to care.

The result? Constant turnover. Burnout. Misalignment. And teams that are busy but not productive because everyone’s rowing in slightly different directions.

The Data Doesn’t Lie

At Better Talent, we’ve seen this play out hundreds of times across the 500-plus companies we’ve supported. The data tells a simple story: when you hire the wrong people, it’s expensive. When you fail to develop the right people, it’s even more expensive.

Turnover costs a company anywhere from 30 percent to 200 percent of a position’s annual salary. That doesn’t account for lost momentum, broken culture, or client churn caused by inconsistency.

Here’s another truth: hiring on gut might have worked when you had a five-person company. It doesn’t work when you’re managing 50 employees, 200 homes, and multiple markets.

Talent isn’t intuition anymore. It’s a science. Behavioral data, cognitive data, and structured hiring frameworks aren’t HR fluff. They’re how you build scalable, predictable performance in a business where people still do the heavy lifting.

You can’t scale chaos. And bad hiring is chaos.

The Real Tech Stack: Your Team

What if we treated our people like software?

We’d start by measuring how they’re wired. What are their drives, their strengths, their blind spots? We’d align them to the company’s mission, making sure they’re in roles that fit who they are instead of trying to force them into who we wish they were. We’d provide continuous updates through coaching, feedback, and development. And when things go sideways, we’d debug, not by blaming, but by diagnosing the system.

That’s what true talent optimization looks like. It’s what separates great companies from average ones. It’s the difference between a team that reacts and one that executes.

And yes, your team does in fact need to be highly technical. This isn’t about going soft. The modern vacation rental team has to be Iron Man–level capable. Think Tony Stark in a headset: data-driven, tech-fluent, and relentless about improvement. But those kinds of people don’t grow on trees. You have to invest in them. You have to develop them. You have to build the environment where they can become that capable.

Here’s the kicker: your team is your technology.

Every process, every guest interaction, every system runs through people. They’re the interface between your vision and your results.

If your people are inspired, aligned, and accountable, even imperfect systems will work. If they’re disengaged, burned out, or in the wrong seats, no system in the world will save you.

Leadership Has to Evolve

This industry talks endlessly about innovation, but innovation isn’t just about new platforms or APIs. It’s about evolving how we lead.

Most operators started out as entrepreneurs, not organizational architects. We learned to manage properties, not people. But as companies grow, your biggest constraint becomes leadership capacity, not market opportunity.

You can’t scale beyond the strength of your team, and your team can’t outperform your leadership.

That means it’s on you, the founder, the CEO, the GM, to build clarity, accountability, and culture. To define what “great” looks like for every role. To hold people to it. And to invest the same time and intentionality in your People Stack that you spend evaluating your tech stack or marketing spend.

I’ve watched companies double revenue simply by getting the right people in the right seats and aligning them with a clear purpose. No new software required.

The Punchline: No One Leaves Because of a PMS

Let’s be honest. No guest has ever left a review saying, “Five stars for their API integration.” They talk about the experience, the service, the feeling. The people.

And employees? They don’t quit because your pricing algorithm was off or your tech stack wasn’t sexy enough. They quit because of how they’re led. They quit because no one invested in their growth, listened to their ideas, or gave them a reason to stay.

So yes, we can keep chasing the next tool, the next dashboard, the next shiny object. But if your team isn’t aligned, inspired, and optimized, none of it matters.

The future of this industry won’t be won by whoever has the best software. It will be won by whoever has the best team.

Because at the end of the day, and I say this with love,

It’s your people, stupid.

Beyond Logos: Why Brand Strategy Comes Before Visual Design

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Your brand is an energy. It’s an experience. It’s the emotional connection people feel when they interact with you or your business. And if you’re starting with logos and colors before you define what your brand actually stands for, you’re putting the cart before the horse.

Why This Matters

Every year, businesses shell out a whopping $28.6 billion on market research. Yet, too many companies still kick off their branding efforts by asking, “What colors should we use?” or “Which font looks best?”

That’s like illustrating a storybook before you’ve even written the story.

Brand Strategy First, Always

Here’s what I’ve learned from working with businesses of all sizes and speaking to CEO groups across the country: A strong brand attracts the right people and the right opportunities. Period.

But here’s the thing, your brand is not about looking “nice.” It’s about being magnetic. It should make people instantly say, “Hell yes, this is for me!” or “Hello no, not my vibe.” Because if you’re trying to appeal to everyone, you’ll end up resonating with no one.

Know Your People (Like, Really Know Them)

Let me give you an example. I’m Gen X, and so are a lot of the CEOs I work with. We’re the MTV generation. We don’t trust easily (we watched Enron collapse and fancy watches at retirement go away). We were the first generation to navigate widespread divorce, the spread of AIDS/HIV, the dawning of terrorism impacting the USA, and so much more. These experiences shape how we, as a collective, approach business and where we spend our money.

So when I quote Sir Mix-a-Lot on LinkedIn, it’s not random. It’s strategic. It’s an emotional connection. And the data backs it up: Brands that create emotional connections see a 71% increase in customer referrals.

How to Build a Brand Strategy (Before You Touch Design)

Before you even think about picking out colors and fonts, focus on this:

  • Define who you are (and who you’re not).
  • Understand your audience’s psychographics (not just their demographics).
  • Develop your brand story.
  • Establish your voice and tone.

Here’s a pro tip: Call up your best customers and ask them why they chose you. What made them say yes? Why do they stay? Their answers will tell you more about your brand than any design consultation ever could.

When Design Finally Comes In

Once you’ve nailed your brand foundation, then (and only then) should you move on to visuals. And at that point, the choices become obvious:

Targeting a modern, digital-first audience? Skip the serif fonts.
Marketing to a luxury clientele? Those serif fonts might be exactly what you need.
Catering to a younger, high-energy crowd? Your color palette better match that vibe.

The Bottom Line

I’m not saying logos and colors don’t matter. They do. But they’re the outfit your brand wears, not its identity. And just like in life, if you don’t know who you are, no amount of fancy clothes will fix that.

So, here’s your gut-check question: Can you explain your brand–its essence, its promise, its vibe—without showing a single visual?

If not, it’s time to go back and do the real work. Because sure, great brands look good. More importantly, though, great brands make people feel something. And that’s what creates long-term loyalty and business success.

So, remember: We write the story first, then we illustrate it. Never the other way around.

Sand N Sea Properties Acquired by Continuum Management Group

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DENVER, CO, UNITED STATES, October 6, 2025 /EINPresswire.com/ — Raincatcher, a national M&A advisory and business brokerage firm serving small and mid-market companies, is pleased to announce that it served as the M&A advisor to Sand N Sea Properties (“Sand N Sea”) in its transfer of ownership to Continuum Management Group.

Founded in 1974, Sand N Sea has been a cornerstone of Galveston Island’s vacation rental and real estate market for more than 50 years. The company has built a reputation for exceptional service, long-standing relationships with homeowners, and a deeply local, hands-on approach to property management.

“For our family, choosing the right partner to carry Sand N Sea into the future was one of the most important decisions we’ve ever made,” said the former owners of Sand N Sea.

“Sand `N Sea has been an integral part of our family for so long.” said Anne Reiswerg. “We spent a lot of time considering the future of the company, and we knew that Raincatcher would help us find the right buyer to continue leading Sand `N Sea in our community.

They understand the vacation M&A market, and most importantly, they understood the value of the strong relationships we’ve built with our owners, real estate clients, team members, guests, and the community. We felt confident working with Raincatcher.”

“Raincatcher’s knowledge of the vacation rental M&A market, combined with their structured process and thoughtful guidance, gave us confidence at every step. They understood what mattered most to us and delivered an outcome that ensures Sand N Sea’s legacy will continue to thrive.”

Continuum Management Group acquires and grows premier vacation rental management businesses, with a philosophy centered on preserving the integrity of locally operated companies while providing resources to support long-term growth.

“Raincatcher’s expertise in vacation rental transactions was instrumental in making this partnership possible,” said Stacy Charlton, COO of Continuum Management Group. “Their team ran a highly professional process and helped us align with sellers who share our values. We are excited to build on Sand N Sea’s incredible foundation and continue delivering exceptional service to homeowners and guests.”

The transaction reflects the growing momentum of M&A activity within the vacation rental management industry, a sector where Raincatcher has deep expertise and a successful track record.

About Raincatcher

Raincatcher is a national M&A advisory and business brokerage firm serving small and mid-market companies. The firm guides business owners through complex M&A journeys by shaping strategy, building competitive tension, negotiating optimal terms, and supporting owners from preparation through to close and beyond. The Raincatcher team brings hands-on experience as founders, operators, and financial professionals, combining technical expertise with real-world perspective. Raincatcher is built on the belief that selling a business isn’t just a transaction, it’s a life-changing transition.

Certain principals of Raincatcher, LLC are registered representatives offering securities and investment banking services through Britehorn Securities, a registered broker-dealer (member FINRA/SIPC). Britehorn Securities and Raincatcher are not affiliated entities.

About Sand `N Sea Properties

Sand `N Sea Properties was founded by a family of Galvestonians more than 50 years ago, and over the years, the company has established itself as a leader in Galveston real estate sales and vacation rentals and as a staunch supporter of the community.

Sand `N Sea Properties manages approximately 190 vacation homes on West Galveston Island; and its experienced team of reservationists, inspectors, housekeepers, laundry techs, and maintenance personnel all make customer service their number one priority.

The company’s top-producing REALTORS® are known throughout the region for their coastal real estate experience and professional expertise.

About Continuum Management Group

Continuum Management Group acquires and grows premier vacation rental management businesses. The company’s philosophy is centered on preserving the integrity and legacy of locally operated businesses, while providing them with the resources and support to thrive for the long term in the vacation rental industry.

When Scale Backfires: The Hidden Risks of Growing Too Fast with Ashley Ching of Inhaven

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As the vacation rental industry matures, growth has become the holy grail for many property management companies. But what happens when scaling too fast starts doing more harm than good?

In this episode, Ashley ChingFounder & CEO of Inhaven, joins us to unpack her in-depth research on why many large property management companies fail and what separates the ones that last.

Drawing insights from over 100 executive interviews across the hotel, restaurant, and vacation rental sectors, Ashley reveals the five pillars of successful hospitality management and how losing sight of them leads to the downfall of even the biggest brands.

We cover:

  • Why diseconomies of scale are real in hospitality and how to avoid them
  • The five pillars that define sustainable hospitality businesses
  • Why curated portfolios and empowered local teams matter more than size
  • What Vacasa and Aimbridge’s struggles teach us about over-expansion
  • How Inhaven is helping property managers raise the standard for quality and consistency

Ashley also shares how her background with Tiffany & Co. and The Home Depot shaped her approach to brand standards and guest experience, and how those same principles can guide operators in today’s competitive landscape.

Connect with Ashley:
LinkedIn: https://www.linkedin.com/in/ashley-ching-7569a5240/
Website: https://inhaven.com/ 


Transcript

Alex Husner  
Welcome to Alex & Annie: the real women of vacation rentals. I’m Alex, and I’m Annie, and we are joined today for the first time with Ashley Ching, who is the CEO and founder of Inhaven. Ashley, it’s so great to have you on.

Ashley Ching  
Nice to be here. How

Annie Holcombe  
is this the first time I feel like we talked to you like, I just feel like we should have had you on, like, 10 times by now, but

Alex Husner  
we’ve done live interviews with you, yeah, never on the actual show,

Annie Holcombe  
yeah, yeah. But I guess in that maybe before we really dive into what we’re going to talk about, why don’t you give us a little introduction about you and in Haven?

Ashley Ching  
Yeah? So again, my name is Ashley Chang CEO and founder of en Haven. I started my career after consulting a Tiffany and Company, and I spent almost 13 years there. I went over to Asia, managed their Asia business from Merchandising perspective, and really learned about the importance of brand standards and creating a consistent customer experience, whether they were visiting our store in Beijing to Sydney, Australia, to Cincinnati. After I got back from Asia, I went in and ran their global merchandising operations and was responsible for all of the assortments and the product presentation in our stores globally. After Tiffany and Company, I left, and I joined the Home Depot and led merchandising for the company store, one of their private label brands, and that’s where I really got into sourcing home products, textiles. Traveled around the world, going to manufacturers in India and China, and there, for the first time, I noticed that each manufacturer, first of all, everything’s produced in the same places. So you go to these manufacturers, and you see things from the Home Depot, Costco, Pottery Barn Restoration Hardware. They’re all produced by the same people. Interesting, yeah. And what was really interesting was that they had their retail line. So the things that you and I buy for our own homes, and then in a separate area of the plant, they had all their hospitality grade supplies that they would produce so and they would be sold on different channels, right? They’re not sold through retail channels. They’re sold directly through hospitality distributors. And I learned at that time these products that are just so much more durable, they go through way more testing than the products that you and I buy for our own homes. And so it was sort of a mental note, an interesting mental note for me. Covid had hit during the time I was there, and so we’re stuck in our four walls. And so my family and I would travel, and we’d stay in vacation rentals, no longer hotels, and just the experience of staying in vacation rentals, you know, you’d find a perfect place on Airbnb or VRBO, but show up to, you know, really crappy mattresses, missing pots and pans, and it was a really frustrating experience as a guest. And so I thought to myself, Oh, why don’t I bring those products that are hospitality grade to the vacation rental space and really create a better guest experience? And so that’s really how inhaven was born. I actually went to the to the executives at the Home Depot and said, Hey, I’ve got this idea. They thought it was a great idea to get their products in these vacation rentals, especially their hospitality grade ones. But at the time, you know, covid had hit and we were our sales were going crazy gangbusters. So they just kept saying no next year. And so that’s, you know, I just said, You know what? This? I don’t think this is ever going to happen at $250 billion company. I’ll just go out and create it my own. And so in Haven was born in late 2022 and we help professional property managers set standards for their vacation rentals around the comfort of this day. So the Bed Bath and kitchen and cleaning we, you know, we focus on the areas that you can repeat across your portfolio of rentals. No one’s looking for a unique sleep experience. They just want a solid sleep experience. So we focus on setting those standards with our property managers, and then we’ve developed a bunch of inventory management tools that, you know, be able to maintain those standards through subscription services through notifications that they’re running low in stock, and they’re able now we’re connecting to various PMS platforms and breezeway to be able to push notifications back to the teams and back to their owners in terms of invoicing.

Annie Holcombe  
Yeah, yeah. But how fun, how fun to be able to get like, I guess, to know that information, like, I add that what you just told me. And Alex, of like, like, all the things I buy, I’m like, wait a minute, like, am I buying it from two places and it’s exactly the same, same source?

Alex Husner  
Yeah, yeah, well, but it also goes to show how important brand is, right? And so we were actually, we were just in Italy, and I was thinking about similar things that I was looking in these different high end stores and looking at different at different watches, and watches, I’m sure, are the exact same way too, right? That it’s like one watch is no different than another for the most part. I mean, they’re coming from the same manufacturers, but you pay for the super expensive one because you’re paying for brand and I think what you’ve kind of done with the linen program is kind of pushing vacation rentals, or assisting these companies that are investing in a higher level product to understand that, that it’s like, that’s why they’re not just an Airbnb to these guests, because it is a brand. There’s a reason that they stay with them, and there is a difference. And I think we as an industry have a lot more ability to control things like that. And you know, products do, like watches or, you know, these sheets like as across an industry, but it’s interesting to hear your history

Ashley Ching  
there. It’s It’s fascinating. I mean, I started in Haven because I was a frustrated guest. Stayed in these homes, and I thought, we just need to improve the guest experience. But what the most interesting finding I’ve had since founding in Haven is the people that actually want this most are the property managers, because as you start to grow and expand, you can have different sheet assortments in all your homes, or different coffee makers, and you really need to set up a system where you’ve got the same products, especially when it doesn’t it’s not related to decor, right? People just still want to feel like a local they want to go to a place and not feel like a cookie cutter hotel, but they don’t want to compromise on their bathing seat, sleeping and eating. And that’s where we’ve really helped create standards. And it’s it’s benefited the property managers and their team probably

Alex Husner  
the most. Yeah, yeah.

Annie Holcombe  
So you’ve had, you have this incredible passion for trying to solve problems, and one of the things that we wanted to talk with you about was not necessarily solving a problem, but looking into the root of a problem. And it was why so many of these large property management groups on not only on the hotel side, but also on the vacation rental side, just keep failing. And so you did this exhaustive study, and so I think we wanted to take a little bit of time to really dive into it and understand why you did this, where you started, what you learned from it. I know I’ve been able to see the presentation before, and it’s, it’s, you did some pretty exhaustive research, and so would really like to hear about kind of the, you know, the genesis of this, and how it came to be, and what you learned from it. Yeah.

Ashley Ching  
So late last year, vicasa announced its proposed sale to the Casa go Consortium, and at that point, a lot of the property managers we worked with immediately reached out and said, What’s going on here? Is our industry in trouble. And so at in Haven, we really started to follow this sale. And it was an incredible sale. There was, you know, two bidder, two main bidders, and so it kind of went back and forth, and what was actually going to happen here. But what was fascinating about the Vacasa moment. It’s just three weeks after vicasa announced its distress sale, the largest property manager on the hotel side. So the vicasa the hotel side, Ambridge, announced its out of court bankruptcy restructuring. And so these two concurrent events happening the largest property managers on both the hotel and the vacation rental side, you know, announcing their financial distress led us to really look into this and understand, you know, what’s happening here. And we went and tried to understand, you know what, what’s the journey of a casa and Ambridge, and they have, if you look in our case study, they have very similar corporate journeys of starting with, you know, just very moderate organic growth to a lot of acquisitions through private equity investments, and then eventually going into eventually just getting too big, and owners and guests starting to churn, and then going into financial distress. And we thought to ourselves, you know, is this just two coincidences that they just happen at the same time? But as we then look back another 25 years, you know, we saw this example of national property management, trying to scale and failing over and over again, whether it was resort quest on the vacation rental side or interstate on the hotel side. And so we really set out to understand, you know, why this happened? You know what does lead to successful property management? So we went out and we interviewed hundreds of executives across the vacation rental of Hotel and Restaurant industries, in Hospitality Management, in property management, and we interview people on the national side of things and the local side to just understand what makes for great hospitality management and where the failures occur. And what was interesting is, I think the media has said there’s three main reasons why these companies have failed. One, their CEO or Executive Team. Two, oh, it’s private equity. Or three, it’s these sort of exogenous events, like 911, we just, it just wasn’t enough. You know, there’s been 15 different executive teams that have tried for salt, for national property management. So can’t just be one person or one team, and it can’t be private equity, if we have examples where it doesn’t work in the public spaces as well. And then, you know, so many companies have been successful even throughout these, you know, terrible events like the financial crisis and covid. So we really, then tried to really peel back the onion of what, what does make for success. And so out of this case study, we were able to really uncover this five pillars of successful Hospitality Management was one of the one of the items that we uncovered. One of the insights was around economies of scale. So happy to kind of go through some of them and just

Alex Husner  
chat with you and get your

Annie Holcombe  
thoughts. Yeah, yeah. Listening. Go, go over to our YouTube channel, and Ashley’s going to share the presentation so we can walk

Alex Husner  
through it. Yeah, you definitely want to be able to see this. So,

Ashley Ching  
so in terms of the five key pillars of successful property management, we have five main key insights, and the first one is around curated portfolios. You know, we heard over and over again, you have to minimize the number of bad apples, and every single property management group has their bottom 10% it’s when you get to 20% or 30% that these properties become just. Distractions to the overall organization and almost become toxic. We heard one CEO say, you know, you really need four out of five. Your four out of five properties need to be drive by and wave properties, meaning that they’re profitable. You know, they’re just kind of doing well. You don’t need to spend time with them. But it’s when it becomes two out of five or three out of five that it really becomes distracting to the organization, and it can lead to a lot of failures. So you know, we give examples where vicasa and Ambridge, they both did a lot of acquisitions through M and A. And so when you acquire all these properties without doing the due diligence on every single you know property, you’re going to take on a lot of bad apples. And so we see a lot of success through organic like just general organic growth, and M and A can be very costly to organizations if they’re not doing the due diligence on each of the properties they’re

Alex Husner  
taking on, makes perfect sense. And honestly, even with companies that maybe haven’t grown through acquisition, I think that’s just a talking point that comes up often now, even if they’ve just taken on properties over the years, to get to that point they’re starting to realize, you know, I need, I need to, now that I have a good business here, I need to get rid of the ones that are holding me back

Ashley Ching  
totally I mean, I just think of my days at Tiffany and Company. I traveled the world. I probably have gone to most luxury malls around the world. And we would go and we would scout out exactly the location that we wanted, whether it be at the entrance or a specific location next to, like the Louis Vuitton store or whatnot, we would pay a premium for that location. But if we didn’t get that specific location, because we done all of our financial analysis knowing it would be profitable on its own, we would walk, yeah? And so, you know, it’s just making sure that you’re doing the due diligence on the locations that you’re taking on to make sure that they’re profitable on

Annie Holcombe  
their own, yeah? Like not compromising on what your brand integrity needs to be exactly. I have a question before you dive into this. So I meant to ask you this previous How did you get these interviews? I mean, because you’re, you know, I don’t know how many people you know in the industry, but I mean, it’s like, especially on the hotel side of it, was it something that you had a power broker that was able to get you in the doors? Or did you just continually ask and ask and ask until they finally, I guess you broke them.

Ashley Ching  
You know, we have a lot of relationships. Our team does with, you know, various players in each of these different sectors. I’m showing on the picture right now, on the screen where, you know, we know, sort of the different companies we talked to across the hotel, restaurants and vacation rental space. So obviously, in the vacation rental space, that’s very easy. We have a lot of great relationships. Lot of great relationships with people here. But in the restaurant and hotel space, it’s really through our network. So we’re able to get in front of in front of these, these key executives. The next key insight we heard over and over again was making sure that your property management companies, the properties that you take on, have similar demand drivers. So one of the examples here is evolution hospitality. They manage about 15 different hotel locations in LA and San Diego, or LA and San Diego, and so they’ve got this urban, you know, kind of upscale consumer that they’re targeting. And they said to themselves, let’s go out and let’s acquire hotel in Palm Springs. Palm Springs is only two and a half hours away. And so they did, and they they took on this hotel. They managed a property. However, in July in Palm Springs, there’s massive sandstorms. And so to get consumer, you know, get guests to book a hotel in Palm Springs in July is very different than getting, you know, occupancy up in LA and San Diego. And so they had to go up and set an entire team up in Palm Springs to try to figure out, you know, this very different market. And so when we talked to, you know, other property managers, it was, you know, making sure that you’re kind of that you’re very specific about the demand drivers that you’re going after. Because once you introduce, you know, many different markets, whether it be you’re in ski and now you’re going to the mountains, or you work with, you know, primarily one bedroom condos, and now you’re taking on mansions. The expectations of the guests, and getting the guests to book those properties are very different, and it forces you to, you know, either you don’t deliver on their expectations, or you just have to, you know, really expand your team to make sure that you’re developing the right marketing messages and you’ve got the right staff in place to manage these properties. So that was really the key insight there is to kind of stick with similar demand drivers as you scale your organization. The third key insight, which was really interesting, which I think is the least written about, at least in you know hospitality journals, is to really be careful and limit the number of owners that you take on, and be very picky with the owners you take on. So an example here, that’s a bit of an extreme. We talked to the Pappus group, which is a Restaurant Group, and primarily they’ve got restaurants in Texas, in the Midwest, Papa see those? Papa does, if you’ve ever dined in those locations, they are owned and managed by one family all of the all of the locations. And so they had gotten word that 15 of their restaurants in the Dallas area had substandard bathrooms, bathroom cleanliness. And so the executive team traveled immediately. Down to Dallas and confirm that, yes, those locations weren’t living up to their standards. And so that next Monday, they decided to replace every single General Manager with the Assistant General Managers, sending a very clear message to the team that these standards matter, and if they aren’t upheld, you know, the man the general managers will be replaced, and that can really only be done so swiftly because they it was all owned and managed by the same group. Now, on the flip side, you know, you have Ambridge, which, at their peak, we’re managing over 350 different owners. And so if they wanted to make changes quickly as a company, and they couldn’t, right? They had to get all of those different owners on board with what they were doing. And so the message that we heard over and over again here is be careful with the owner you’re bringing on and just, you know, make sure you’re limiting the numbers, because if you want to be able to drive change, having 100 owners is a lot different than having, you know, 20 or so,

Alex Husner  
yeah, and I think companies that have owners that are more like investor type owners, where they’ve come on and they’ve got, you know, five or 10 properties within that company, you know, if you have a bunch of those that, of course, it’s going to simplify things, right? I mean, it’s less conversations that you need to be having with people. And if you have software that answers a lot of the questions for those owners too, you know, that’s a big part

Ashley Ching  
of it. It’s interesting because we, we have the number in the vacate, sorry, in the hotel space, we, we haven’t seen a successful property management company in the hotel space really be able to manage more than 300 different owners. You know, you have Ambridge, but they had their out of court bankruptcy restructuring, and then the number two, Highgate, took on a very large distress Portfolio A couple of years ago, and going back to point number one of a curated portfolio, we know that they are probably in a bit of trouble. So we know that the number for hotels is around 300 what is that number for the vacation rental space? We don’t have that number. But, you know, just we’re really trying to understand how many, how many different owners you can manage at once. They’re owners of the properties. So in the hotel space, very similar to the vacation rental, the owners are separate than the managers, so they hire the property manager to manage that location.

Alex Husner  
Got you but I think the argument could go both ways, on homeowners and also owners in your company, because when you’ve got a smaller decision tree there, just like the example you gave on the bathrooms, like, if you’ve got to take it up the chain to get approval from five different ownership groups that are part of a company. And I work with companies that are set up that way. You know, things can take a lot longer, totally

Ashley Ching  
and I mean, I almost kind of want to skip the fourth pillar and go straight to the fifth pillar. Pillar is all about empowered local hospitality professionals feeling empowered to make decisions. We talked, we heard, you know, we talk a lot with about you in the hospitality industry, you you hire people with a hospitality gene, people that have a smile on their face after even getting yelled at by their owners or guests, they want to make for successful experiences, and they continue to show up every day with a smile on their face. And these types of people need to feel empowered, empowered to make decisions on their own. And so when companies like Ambridge would acquire these property management groups, and instead of doing what’s best for your owner, you know, they now are trying to do what’s best for Ambridge. And they would go to Ambridge and say, you know, we want to do do something different for our market. And Ambridge would say, well, that’s not really the Ambridge way. They would feel disempowered. And those types of people need to feel empowered, so they just leave and they go to other hospitality managements where they can deliver the experiences. And so what we found was there’s massive brain drain from some of these larger companies where you’re left with them the worst employees to manage those locations. So, you know, the feeling empowered to be able to make decisions, not having to wait, you know, many days. You know, really empowering your employees is critical to the success of your overall company. And then, you know, the last pillar was on local oriented operations, really making sure that you’re delivering your operations locally versus centralizing a lot of the various parts of your organization. So an example here is on Ambridge. They tried to centralize a lot of the finance functions and tax, and they just missed some of the local needs, like local jurisdictions tax needs on the tax side of things, or they tried to centralize reporting, you know, at the Ambridge way. But a lot of these hotel owners own multiple hotel properties, but not all of them are managed by Ambridge. So, so if they tried to roll up their financials, and they had to use this new Ambridge template that didn’t have all the information they need, it was very frustrating. So they couldn’t get, you know, a picture of their larger portfolio properties. And so that led to a lot of churn, you know, in the vacation rental side. I know we spoke to one of the executives that his company was bought out by a larger vacation rental company, and they did, you know, pre arrival check ins, and it was really important to their market that they did this. Was a differentiator, and this company said, no, no, we don’t do that here at this company, you know, so, and it led to a lot of frustration, because they needed, they needed to ensure that the guest experience was going to be great. And so that led to, you know, a lot of just angry owners and guests and team

Alex Husner  
members. I think that’s kind of like the pipe dream in our industry that we hear people ask us about this all the time. Of Well, I think if I can just, if I get some properties in one location, and then I get some in another state, but I’m going to keep everything centralized that’ll go across all the properties. And in theory that works, and in some in some areas, I think it can be applied. But there are very few examples of how that has worked. Well in our industry to this point, to be honest, because I think they’re like, as you mentioned, there’s just still so many nuances, especially on the marketing side. I think you can centralize some marketing, but you also have to have somebody that’s local boots on the ground, that actually understands what’s going on there and the destination and about the properties. So some of these things, it’s more like, you know, it’s better to be like a hybrid of centralization on on different assets, yeah.

Ashley Ching  
And then, you know, kind of To the Point on just scale and economies of scale. That was a really interesting finding. And sorry, I’m just going to flip Fast, fast forward a couple slides here. We found that through our interviews, is that in hospitality, as you scale, you experience diseconomies of scale versus economies of scale. And so let’s just take an example of ball. Corporation is the example we use in the case study. And ball is the largest manufacturer of aluminum cans in the US. And if you take labor as an example, when they set up a manufacturing line that manufacturing one manufacturing line can produce up to a billion cans a year, and it only takes 18 people to run that manufacturing line. So whether you’re producing 100,000 cans or billion cans, you only need 18 so the more volume you add to that manufacturing line, the unit economics improves, right? Because it doesn’t. You don’t need to hire more people. Yeah. Then on the service side, where we saw diseconomies of scale, we use an example in the case study called on Forney Independent School District. And this is one of the largest, or the fastest growing school districts in the country, and it’s based outside of Dallas. And so we show in the presentation that, you know, this school district grew from about 8500 students in 2013 to just under 19,000 in 2025 this year. Wow. And so they’ve grown a lot in their student population, but as they’ve grown in their student population, they’ve actually grown their staffing at a faster rate because you have to maintain the same student to teacher ratio, and then as you bring on more teachers, you need more administrators, and you need to invest in different programs like special education and after school programs and and so this the staff ratio actually grew at a higher rate than the student ratio. And we think about this a lot in service industries like hotels and restaurants. As you scale, you need more administrators, inspectors, you know, people to help manage that overall business. So we really don’t see economies of scale when it comes to labor. And then we looked at, you know, just, you know, economies of scale with when it’s comes to bulk purchasing, right? Well, in the example of ball manufacturing, 55% of their costs are just in materials. So as they go and they, you know, improve rates on aluminum, that can have a very significant impact to their bottom line. But if you take the hotel industry like Hilton, 55% of their costs are in labor. And so as they get bigger, people expect better wages, better benefits. You’re exposed to organized labor unions. And so actually the costs increase in terms of your biggest cost center then decrease. And so we really just overall see diseconomies of scale versus economies of scale in the service industries,

Annie Holcombe  
makes sense? Stuff? Yeah, yeah, yeah,

Alex Husner  
interesting to see. I mean, as you know, life evolves and AI becomes more a part of, you know, everything in business, like this study in a few years, I wonder how it would be impacted. What would your thoughts more than that.

Ashley Ching  
So it’s funny, um, you know, we talk about another example, except my mom of young kids is, like, preschools, right? You still need people to provide service. People expect people in the hospitality industry, and so I think AI can help on, like, the back end. But, you know, from a preschool perspective, you would not be okay if you’re like, wait, but I’ve got this AI bot that’s in the classroom, right? Yeah. And I think that’s very similar, you know, I think with AI, we’ve done some research outside of this, outside of the study. You know, one of the industries has probably embraced technology the most is the airline industry. You’ve got, you know, all the apps and the kiosks and whatnot. Yeah, and what we’ve seen over the last 30 years with airfares is they’ve dropped significantly, down 35% and the number of complaints have risen significantly. And so I think it’s just, you know, I think AI definitely has its place on, like, the back end stuff, but how much you introduce it into that guest facing interaction? There’s some lessons learned with the airline industry. We see it in economy hotels just people won’t pay for as much when there’s people pay for people and service. You know? The other area we see it in is in hotels and a chain scale pricing, right? Economy hotels may have one person there to check you in, but when you walk into a Ritz Carlton or four seasons. I mean, there are just so many people in the lobby swarming the lobby, ready to press the elevator button for you. And so people pay. We think that’s probably the biggest differentiator between an economy hotel and a luxury hotel is the number of people in the in the lobby. That’s what people pay for. They pay for service. And so it’ll be interesting to see how AI can be incorporated in that in a way that doesn’t impact, you know, the ADRs and the guest experience, yeah, for sure. So there’s lots of different information in here, you know, we hit on, you know, a lot of different topics, but I think these were the two main that were have been the most interesting to to our audience, that what

Annie Holcombe  
was your big takeaway from all this? Like, how? Like, if you had to write, you know, say, for, you know, Costa go as they venture down this path of taking Vacasa, like, what? What did you glean from this that you’d say was a recommendation that you could offer a company so they can succeed, or maybe pitfalls to avoid?

Ashley Ching  
Yeah, so there were two, you know, and we’ve been asked a lot like, Okay, well, what about these different models that we’re seeing out there? Like, you know, Casa goes model. And I think the, the biggest, the biggest takeaway that we have is any model can be successful if they, if they really consider the five key pillars of hospitality and really use those as guiding principles. You know, the failed companies really, they almost rejected these principles, and that’s why they failed. And then the other framework we bring up in the case study that I think is really important to consider is around your operations. Are you trying to achieve? There’s three main areas that companies try to achieve, whether it be service, scale or profitability. But we heard over and over again in our interviews that really, you can only get two out of three. You can’t be you can’t develop a service at in scale and be profitable. And so really aligning your business around two of those three principles is key. So for example, vicasa was really organized around service and scale right their property management and they’re trying to scale, but they were never profitable. We’ve got a company that we study in this case study called American homes for rent. They have about 60,000 single family homes that they rent out. They own them and manage them. They provide zero service, right? This is just, I mean, they’ll they’ll come in, maybe if your HVAC breaks, but they’ve been extremely profitable, and they’ve scaled to 60,000 homes. So, you know, we have examples in the case study of all three. You know, companies that have chosen two of the three, and sort of, who the success stories are of those of those

Alex Husner  
areas. Yeah, I think another way of saying that same thing that my former mentor used to always say was, you could have quick, cheap or good pick two, right? Because it’s like good, but it’s not going to be cheap. You can have something quick, but it’s going to be cheap. So, yeah, it’s a really good point, yeah.

Ashley Ching  
And I think about like, you know, we work with a lot of the local professional property managers, where they really excel at service and profitability, right? But they’re these local teams, like abode luxury rentals in Park City, or like Beverly Sorrell and bestness and Hilton Head, right? But that they’re not focusing on scale. They’re focusing more on service and profitability. So, you know, that’s where I think a lot of our in Haven customers are focused. You know, with property management, we found, and this is sort of another key insight, is, the more complex your business model is, the harder it is to scale. And so, you know, to scale, you have to have, really, you know, you need to be, have aligned demand drivers, and you need to be, you know, very aligned in your product and what, what guest experience you’re you’re delivering. And so the more differentiations that you have in these areas, the more complex your business model has, and complexity is, like the killer of scale. That’s a quick summary of what we what we uncovered.

Alex Husner  
Yeah, I think when you look at our industry too, I mean, there’s three categories. It’s really important for vendors in our space to understand the difference between what the motive is of the property management company, because it’s like, if you’re a product that like, really, the main benefit is that you help companies scale. But like you just mentioned, Beverly in Hilton Head, if she’s not interested in that, she’s interested in the service and profitability, what you’re talking about, scale means nothing to them. So, you know, just just understanding your ICP, I think is really important. And I feel like we see. Up really not done well at a lot of the trade shows when you’re walking around, because it’s like, you need to ask companies and managers, what is their goal before you start going down a rabbit hole, and maybe your product offers something that speaks to all three of those. But you know, it’s really understanding the pain points and the goal of the property management company 100%

Annie Holcombe  
Yeah, Discovery first. And yeah, discovery, yeah, no. I mean, it’s same from the channel side, no, as I say it’s same from the channel side, like, distribution, like, that’s one of the things that I always got frustrated about, is like, all channels are not good for everybody. All channel managers are not good for everybody. All PMS are not good for everybody. I mean, like, there’s, there’s everybody has a specific kind of niche, is the wrong way to say it, but they have a customer profile that works best for them. Can they service others Absolutely. But if you don’t understand what the customer’s core needs are, like, all you’re doing is just like throwing words like verbal vomit on them, you know, like they’re you’re not helping them. So they’re just not gonna, they’re not gonna buy from you. But so this is, I mean, like, this is the second time I would say it’s, like, so amazing that you did this. Are you gonna do like, a follow up in, again, you know, we can talk about Costa go, because that’s the one. That’s the Vacasa Costa go situation. Are you gonna do a follow up in like, 18 months to say, like, Okay, where are they at, and where is Ambridge at? You know, through their reorganization?

Ashley Ching  
Yeah. Yeah. So it’s interesting. The chairman of Ambridge, Steve Joyce, is actually on our advisory board at in Haven, so we’re watching, we’re watching Real Time the changes, and he’s come in now after and to make all these changes. So we’re matching real time. And we’ve taken him through the study, and, you know, he talks about the five key pillars, and he’s like, this is exactly, you know, we’re looking at curation, and we’re looking at our number of owners. And he’s like, we’re using these as guiding principles. He didn’t, he didn’t. Those are the things and and I’ve had a conversation now with Steve Schwab, we’re doing an event together at Verma, and he agrees. I mean, a lot of the things that he’s doing at Vacasa through casago. I mean, he’s very much bringing, you know, the operations back to the local teams, bringing the decision making back, and how he’s very pro local wins. And so it’s very what they’re doing are very aligned with what we found in terms of what makes for successful property management business. So it’ll be super interesting to follow up on this in 18 months.

Annie Holcombe  
Yeah, we’ll pencil you in for that, for sure.

Alex Husner  
Yeah, I remember during the, you know, this past spring, when everything was going back and forth on Costa go and vicasa, and, you know, it was anybody’s guess what was going to happen there. But, I mean, you put out, like, whenever you had a post, it was like everybody was living and dying by to see when the next one would come out, because you had such great information on that. But, I mean, you’re obviously, you know, you’re brilliant to put all this together, but you spent a lot of time on it, right? I mean, like, there was

Ashley Ching  
a lot of deep research. It’s, you know, there was hundreds of pages of financials to read through, but I think, you know, our customers were coming to us and asking, what is happening here, you know, what is the state of the vacation rental industry? And so it was a moment to say, Okay, here’s what’s going on. Kind of lead them through the process, but also, you know, give them the latest updates. And, you know, it was just, it deals like this don’t happen very often, right, right? We’re two competing bids, massive bids, and it was just, it was fascinating. It was so fun to follow and fascinating at the same time, and to be able to put out the information. And, you know, we were trying, we weren’t biased. We’re just literally presenting what was in these financial reports through either David Davidson keppner or through the cost of go Consortium. So it was a fascinating follow, and I’m really hopeful that the Casa go team can really turn this business around. Yeah.

Alex Husner  
And so as your customers are coming to you and asking questions about this, I mean, where, where does inhaven stand? Like, what are you telling them? Of, like, takeaways based on the information?

Ashley Ching  
Well, I think it’s just it, and that’s what really drove us to do this deep dive study. Is okay? So we’ve seen these failures sort of over and over again over the past 25 years. What does make for successful Hospitality Management? And so that’s where, that’s why we put out this case study, is through all these interviews that we did, we really feel confident that the five key pillars, the operating principles, that you choose, those are really great frameworks to deliver on successful Hospitality Management. One of the findings that we talk about briefly in this case study, that we’ll be spending a lot more time on, is that in every single hospitality management business, whether it be restaurants, hotels, airlines, rental cars, there is a quality framework or chain scale, right? So you know, and you mentally, you don’t think about, okay, am I booking an economy hotel versus laundry? But you have set your expectations on you don’t expect a Ritz Carlton experience at a Motel Six or I go in the restaurant industry. If you go and you show up at a McDonald’s, a fast food restaurant, right? You would, if you walk away in that restaurant to go to the bathroom, you’d be very surprised if the person behind the. The POS came over and folded your napkin while you were away, right? You wouldn’t, you wouldn’t be surprised. Of that type of experience at 11 Madison Park, you know, the fine dining and you don’t when you fly spirit air. You don’t expect the same sort of service that when you fly Delta. And so the these, this chain scale, does not exist. Exist in the hotel. In the vacation rental industry today, what booking on Airbnb or verbo is a complete roll of dice. You have no idea. You know, you can sort of see the pictures. You can see their super host status. But do you trust those reviews? And so it’s a complete roll of the dice. And there’s, there’s nothing that the consumer knows. Okay, this is what I’m paying for. This is what I should expect when I show up at these properties, unless you’ve been able to do research on the property management business, which most people don’t even know how to do that. And so what we’re doing is we are going to be delivering that the vacation rentals First Quality Framework, starting with our existing customers that have fully standardized within Haven, the Bed Bath and kitchen, but also are have these service level tiers as well. So we know, you know, Rachel and Rob at abode have about a one person, one staff member to every five property ratio. So their service is pretty high end, right? They’ve got very high end, I should say, you know, they’ve got concierge services. If you have an issue in your home, they’re probably there, but they’re probably there within two minutes, right? They’ve got the local team there to service you, versus, you know, a property management company that operates at more of like a one to 15 one, one staff to every 15 homes. And so we can pretty much chart what the service is going to look like. The service levels will look like in those homes, and then obviously the quality, because, you know, they’re using the inhabited standards. And so that is what we’re delivering starting this fall, is this First Quality Framework for the vacation rental industry, where guests can find these homes based on this, based on the quality framework.

Alex Husner  
Yeah, that makes sense. And I mean, since you’re so into the data and doing case studies and things, have you done any case studies on your clients, of people who have started using inhaven, what’s that done to the brand, the brand experience, to their bookings, to revenue. I mean, any anything on that side?

Ashley Ching  
Yeah, I was just talking to a large client in the mountain towns of Colorado yesterday, and she was saying, we’re going to do a case study with them. You know, three years ago, they didn’t have in Haven, and the reviews have consistently gotten better because now they’ve got their standards in place. And so, you know, people are consistently commenting that they loved at the kitchen, the dining experience. They love the beds, the pillows, etc, and so we see it in reviews. They’re able to charge more per night because of the standards and the overall look of these of these places. But at the same time, they’re seeing significant cost savings, because when you go and you standardize and you’re not you’re able to get much better bulk purchasing. So they’re saving anywhere between 20 and 75% on their purchases. So, you know, we just see it from a we see the better reviews. The staff are all lying on what they need to purchase. It’s very clear when something breaks or gets damaged, this is what we were punish it with, and then the cost savings are just huge.

Annie Holcombe  
Very cool. So this leads up to, we’re all going to be heading to vrma, and you mentioned that you’re doing a session with Steve Schwab. Are you? You’re always doing a lot of things at all these conferences. Are you presenting other things that people should look out for? And yes, beyond that, you know what’s what’s kind of on the roadmap for inhaven going into next year?

Ashley Ching  
Sure. So Verma is exciting for us. We’ve got a couple of different events happening. One is the hub session with Steve that we’ll be doing on just the vicasa turnaround, and the lessons learned. We’re going to go through the hospitality framework with him. The second is, I’ll be taking the main stage on day two with Tim Ross Leo from VRBO Steven from Marriott homes and villas, and Richie from price labs, and Jennifer mucho from arrive. Now we’ll be talking about future proofing the industry. And so we’ve got a lot of great topics to talk about, including AI and, you know, in terms of pricing and just trends that they’re seeing on their side, that’ll be an interesting conversation. And then I’m also going to be doing a session with Valerie Genghis and Julie George from movie mountains, on just the importance of brand standards and how you get started.

Alex Husner  
You got a busy schedule next week.

Ashley Ching  
So that’s so Burma is exciting. And then after that, you know, we’re really we were at Verma. We’re unveiling this, this quality framework and a distribution site where people can now find these properties, and throughout the remaining of the year, we’ll be announcing some pretty exciting partnerships with various lodging and credit card companies. So a lot to share there. Wow, as we get the distribution out, because we want you know these these property managers that we work with that, take the time and really set their standards. Now we want to help guests find these locations. And so, you know, getting, getting their locations in front of more eyeballs will be important. So, so that’s sort of the next step in the inhaven journey.

Alex Husner  
Yeah, I love it. I love it. It’s been fun to watch so far and just see, you know, I’ve been. So many of your customers were at these shows, and Valerie being one of them that they just rave about working with you guys.

Ashley Ching  
So that team is so awesome. I mean, we’re just lucky. We’re in the hospitality industry, and everyone is just so incredible that we’ve met and been able to work with. It’s just a joy. And our team loves all of all of the different property management companies that

Alex Husner  
we work with. Yeah, awesome. Well, this is going to come out on a week before vrma. So if anybody wants to get in touch with you or maybe set a meeting for the conference, what’s the best way for them to get in touch with you or your team?

Ashley Ching  
Yeah, so they can reach out directly to me at ashley@inhaven.com, or on LinkedIn, and happy to set up a meeting. Would love to meet anyone that wants to talk procurement or standards, or just this case study at Verma.

Annie Holcombe  
Well, Alex and I will be live at the RMA, so definitely love to catch up with you, kind of maybe the last led the last afternoon on Tuesday, get kind of your, you know, recap of how things were, and talk about some of these exciting new announcements that you’re going to be

Ashley Ching  
making. Great I would love

Alex Husner  
that. Yeah, yeah, yeah. I’m glad you mentioned that. Annie just wanted to also mention, for anybody, if you’re at vrma, we’re going to be in the vendor Hall. I believe it’s over when you walk in. I don’t know the booth number, but it’s over to the right hand side. But we’ll be set up with the podcast. And I know vrama is a rival podcast will be set up as well, and Amber hurdle is going to be kicking that off, so be sure to stop by. Got a quick interview. Say hi. We’d love to see everybody. But in the meantime, if you want to get in touch with Annie and I, you can go to Alex and Annie podcast.com and until next time, thanks, everybody.

6 Hot Takes on the Future and Growing Pains of Short-Term Rentals with Simon Lehmann

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The short-term rental industry is at a turning point. Regulation is tightening, OTAs are shifting power, and owners are demanding more transparency. Technology and AI promise efficiency, but they also raise new risks. Safety sits at the center of it all. This is the roadmap industry leaders will be referencing all year.

Simon Lehmann, your host, has more than 20 years of hands-on experience shaping STR worldwide. He is the founder of AJL Atelier, where he and his team have advised more than 100 companies across the sector. A board member, investor, and trusted voice at global industry events, Simon has seen every side of the market. His perspective comes from years in the field, guiding operators, tech founders, and investors through growth and disruption.

The 6 Hot Topics Shaping STR in 2025 and beyond:

  • Regulation – What new rules mean for growth and compliance.
  • OTAs – How platform dynamics will impact supply and demand.
  • Owners – Rising expectations from those who hold the keys.
  • Tech – Tools that will decide who scales and who stalls.
  • AI – Where intelligence meets disruption in STR.
  • Safety – Why trust remains the industry’s most valuable currency.

If you found this episode valuable, we encourage you to share it with colleagues or stakeholders in your network who are navigating the future of short-term rentals.

Resources

Stay connected:


1Transcript

Introduction: [00:00:00] He’s one of the world’s foremost experts on short-term rentals and vacation rentals.

Introduction: [00:00:04] He’s a man of many, many skills, and I would say a master in the industry.

Introduction: [00:00:08] Most of us know him from fireside chats. Others won’t forget his prediction that property managers could all become glorified cleaners one day.

Introduction: [00:00:16] Well, pull out a pen and paper because this gentleman is a wealth of knowledge in this industry.

Introduction: [00:00:21] We have been veterans for a long time, admire him, and we listen to what he has to say.

Introduction: [00:00:26] An absolute legend in our short-term rental space.

Introduction: [00:00:28] We got a legend in the industry. First round Hall of Famer for sure.

Introduction: [00:00:33] Unanimous, the one and only Simon Lehman.

Introduction: [00:00:37] Simon. Simon Lehman. That is a hell of a buyer. Mr. Lehman, welcome to the show. So happy to have you.

Simon Lehmann: [00:00:44] You are listening to STR Global Unlocked. Brought to you by AGL Artillery, the show where I speak with the leaders shaping short-term rentals worldwide. I am Simon Lehman, and after two decades buying, selling, advising, and investing, things. I’ve built a network that spans continents and categories. This podcast brings that network to you. Real conversations, global insight. No PR fluff. Let’s get started. Let me start with a bold statement. Short-term rentals are older than hotels. Long before Marriott, Hilton, or any other large hotel chain, long before Expedia, Airbnb or Booking.com, people were already sharing their homes with travelers. At the very beginning, we literally shared our caves with each other after hunting. Later it was barns, chalets, cottages. Hospitality began with trust. But today, short term rental is no longer just a side hustle or a quirky idea. It’s a global battleground. Billions are being invested. Cities are cracking down, technology companies are consolidating. And in the middle of it all, our owners, managers and our staff being squeezed between platforms, regulations and rising expectations from guests and owners. And in today’s first solo episode, we’re going deep into one of the biggest challenges in short term rental. How do we move from survival to sustainable growth when regulation, OTA, dependency and AI are all reshaping the game? Let me start with a story from my own career. When I was running Interhome, one of the world’s largest vacation rental company, our industry was still invisible to the mainstream. Hotels dominated, and very few believed vacation rental would ever be taken seriously as part of hospitality.

Simon Lehmann: [00:02:55] We were seen as a fringe, messy and unprofessional. Then along came platforms like HomeAway, now Vrbo and later Airbnb, Booking.com and everything changed. Suddenly short term rental became mainstream. It was tolerated. Guests began to choose them over hotels. Investors started paying attention. Regulators couldn’t ignore us anymore. Covid was a blessing to our industry. But here’s the catch. Even with all the money, tech and scale that has poured into this industry, the one thing that never changed is trust. Short term rental still relies on it completely. Trust is the most important asset we have in this industry, and sometimes that trust is very fragile. On a family trip just recently, my son Jack was asleep in an Airbnb apartment and a heavy picture frame came crashing on his head in the middle of the night. Thankfully he was fine, but he could have been a disaster. And it reminded us guest safety and therefore guest trust is still the foundation of everything we do in this industry. So how do we get there? I see the evolution of short term rental in three acts. Act number one the origins. Short term rental is older than hotels. Families sharing barns, caves, cottages, chalets and many others. Pure. Pure. Trust at the center of it. Act number two. The community area. Platforms like Airbnb tapped into spare rooms. Reviews. Trust badges. Belonging. It felt personal. Act number three. Professionalization and corporatization PMS systems. Institutional Crucial investments. Otas, acting like global gatekeepers, scale capital and consolidation took over.

Simon Lehmann: [00:05:12] And now we’re entering act number four. The future will define by whether we rediscover trust and uniqueness, or whether short term rental becomes commoditized into something that looks and feels like just another hotel product. And I don’t think we want that. That’s why today I want to set the stage for the podcast by walking through the six hot topics. These are the pressure points I see every day when I work with operators, investors, property managers, technology providers all around the world. They are universal. Think of them as the fault lines that will shape act four of this industry. Let me begin with the first hot topic regulation. It’s not a future problem. It’s here. It’s here to stay. New York has cracked down. Barcelona has cracked down. Amsterdam, Zurich, Berlin, Sydney all have to put restrictions into place. But why? Because short term rental has become a political issue. It’s tied up with housing affordability, community wellbeing, Anti-urban policy for too long. Many in our industry have acted like rebels, scrappy outsiders. But let’s be clear we’re not outsiders anymore. Short term rental is mainstream. Hospitality makes up 14% of global hospitality, and mainstream industries must operate by a different set of rules. If we don’t create real standards on safety, on transparency, on data, on accountability, then governments will improve their own standards on us, and I promise we won’t like their version. Key point the license to operate is no longer guaranteed. Regulation is existential. Ignore it at your peril. Point number two OTA dependency margin compression.

Simon Lehmann: [00:07:26] Now let’s talk about platforms like OTAs. Airbnb gets the headlines, but don’t forget Booking.com and Expedia and many others. They’re just as important. They deliver oxygen to the property managers. Booking demand reach. But here’s the uncomfortable thing. They also set the rules and the costs at the same time. Every operator I speak to is facing rising costs labor, cleaning, technology, compliance, payments, marketing, and many others and owners still expect maximum returns. That’s margin compression managers squeezed from all sides. If you’re listening from the US, let me make this clear. If you are relying on Airbnb as your only channel, you are fragile. One policy change, one algorithm update, one new fee structure and new business model is at risk. We have just seen it recently in Europe. By contrast, most professional managers distribute across ten or more channels plus direct bookings. That diversification makes them far more resilient. That’s why many European operators remain profitable, while some in the US have struggled in the past. Baltic Ota dependency is fragility, diversification and direct bookings are no longer optional. They are survival. Point number three owners decide outcomes. Here is something most operators get wrong. They think that they control the guest experience, but actually they don’t because the owners do. Remember, we still build our business on trust properties from homeowners. If an owner won’t invest in repairs, won’t upgrade the software, won’t fix the plumbing, put a new paint of code, a coat of paint on, or upgrade the curtains. It doesn’t matter how good your PMS is or how slick your guest messaging system is.

Simon Lehmann: [00:09:36] The guest will blame your brand for a bad experience. Cliff Johnson, co-founder of Okasa, told me bluntly, our conversation managers need to courage to fire some of their owners who won’t meet the standards that you set. That’s hard, but it’s necessary. And he’s right. Guests don’t care whose fault it is. They just want a safe, clean, enjoyable stay. The key point here protect trust. Even if it means saying no to owners. We don’t like to say no to owners. Sometimes you need to walk away from inventory that drags your brand down. Point number four tech consolidation and innovation tax. In the last decade, we’ve seen an explosion of innovation more than 500 tools in our space. Dynamic pricing, guest messaging, cleaning software, smart locks, IoT integrations and many more. But alongside that creativity we’ve seen consolidation and consolidation comes at a cost. Many property management systems have turned into gatekeepers. Startups have to pay five figure fees just to integrate. Apis come with revenue shares. In effect, it’s an innovation tech and that tax is suffocating the very creativity we need. Bold take the winners of the next decade in technology won’t be the companies that wall off their ecosystem. They’ll be the ones who open them, who empower integration, who let innovation thrive. Point number five AI equals discovery. Revolution. How could we not talk about AI today? Carl Shepherd, co-founder of HomeAway, reminded me in our conversation. Homeaway is early dominance came from SEO, who everyone.

Simon Lehmann: [00:11:39] Google was in demand. Today we’re living through another discovery shift. Guests won’t scroll through hundreds of properties anymore. They’ll just simply ask, find me a safe, family friendly three bedroom home with a pool close to the beach and near the shopping area. And AI will curate, not just search. Ai is also changing operation, yield management, guest communication, even owner reporting. But here is the catch. As Steve Schwab from Coarsegold told me, AI must make us bionic and not robotic. It should free humans to focus on hospitality, not to replace them. And with with chatbots, for example, put the humans where it creates smiles. Put technology where it creates efficiencies. Key point AI is the new SEO moment. Those who adapt will own the next decade of demand. Last but not least, point number six the least sexiest in our industry operation, safety and trust. It’s not glamorous, but it’s everything. I come back from my London trip story, my son Jack, asleep in an Airbnb apartment, picture frame crashing down on his head. Thankfully he was unharmed, but that incident reminded me. Guess trust is fragile. Cleanliness. Safety checks. Maintenance. These aren’t optional anymore. They are the foundation of trust. Guests don’t care how many integrations you have, what your tech stack is. If that smoke alarm doesn’t work. Bold tech. The winners of act four won’t be those who grow faster or raise more capital. They’ll be those who deliver consistent, safe, reliable hospitality that guests can trust. So let me quickly recap.

Simon Lehmann: [00:13:46] Point number one regulation is real and here to stay. And it’s existential. Number two OTA dependency creates fragility. Diversify or die. Number three owners decide outcomes. Fire bad ones. Number four tech consolidation. Risk. Choking. Innovation. Open. Beats. Closed. Number five. Ai is the new SEO. Adapt now. Number six. Operation and safety remain the foundation of trust in short term rental industry. If you only remember one thing from today, trust is still the currency of this industry. Whoever builds trust at scale will win the future. So give me time to for a quick preview in the coming weeks, you’ll hear directly from leaders shaping these debates, such as Carl Shepherd, co-founder of HomeAway, Glenn Fogel, CEO of Booking Holdings, cliff Johnson, co-founder of Okasa. Graham Donoghue, CEO of forge Group in the UK Steve Schwab, So we of course, ago just recently acquired the Casa Quirin Schweighofer, CEO of McAfee, recently transacted to Oyo in Australia and many more voices from around the world, not just in short term rental but also hotels, hotel CEOs, proptech and real estate. Subscribe now so you don’t miss those conversations. Bottom line don’t chase growth without trust. Thanks for listening. That was STR global unblocked where we say what others want. If you got value from today’s episode, send it to someone who is still playing it safe. Follow the show and get more global insight at Uptodate.com. The globally recognized SDR consultancy I founded, and that proudly brings to you this show. More bold conversations are on the way, so stay tuned.

40 Years of VRMA: A New Chapter for the Industry with Anne Gardner

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This year marks 40 years of the Vacation Rental Management Association (VRMA), a milestone that comes at a pivotal time for the industry. 

In this episode, Alex & Annie sit down with Anne Gardner, Executive Director of VRMA, to explore how the association is entering a new chapter of growth, engagement, and industry leadership.

Anne reflects on her first year as Executive Director and shares how listening to members, strengthening communication, and re-energizing volunteer leadership have reshaped VRMA’s direction. From transforming the design of its events to amplifying advocacy and expanding education for managers of every size, VRMA is building a foundation for the next 40 years.

In this conversation, we cover:

  • Why listening to members has been central to VRMA’s renewal.
  • How this year’s 40th anniversary conference in Las Vegas is setting a new standard for engagement, education, and networking.
  • The role of smaller operators in the future of professional property management.
  • How VRMA is working with local associations, DMOs, and even hotel groups to strengthen advocacy and industry collaboration.
  • What’s ahead for VRMA as it continues to evolve with the needs of its members.

Whether you’re a longtime member or new to the vacation rental space, this episode offers valuable insight into how VRMA is leading the industry into its next era.

Connect with Anne:
LinkedIn: https://www.linkedin.com/in/anne-gardner-mba-cae/

Connect with VRMA:
LinkedIn: https://www.linkedin.com/company/vrma/
Website: https://www.vrma.org/


Transcript

Alex Husner  
Welcome to Alex & ANnie, the real women of vacation rentals. I’m Alex and I’m Annie, and we are joined by Anne Gardner, the Executive Director of VRMA, the Vacation Rental Managers Association. Anne, so good to see you again.

Anne Gardner  
Absolutely Good to see you both. Thanks for having me on today.

Annie Holcombe  
Absolutely well. Before we get started, why don’t you give us a little bit about your background. Reintroduce yourself to our audience, for anybody that is not aware of who you

Anne Gardner  
are, sure glad to so I am the fairly new Executive Director for vrma. I joined the organization in spring of 2024, as your interim Executive Director, and then converted into being sort of your, your full time, permanent Executive Director of vrma in November of last year. And so this will be the second of our annual conferences that I’ve participated in, but it’s been a great opportunity to join and come from a background that I have in professional nonprofit management, specifically trade organizations, and so that’s I have an organizational leadership background, and have worked in a lot of tangential pieces of our industry, representing organized real estate and commercial real estate, being a sort of developer and an owner operator myself in the commercial sense, and just doing all those different pieces and parts managing an event center so hospitality front and focused, and weddings and corporate venues and whatnot as part of a structure. And so it’s been a nice opportunity to bring a lot of little pieces of some of what I’ve done in the past in helping other organizations grow and thrive to the work we’re doing right now with vrna.

Alex Husner  
Well, definitely from, you know, the outside slash inside, we’ve seen a lot of changes that have come, you know, to the surface since you’ve been involved since April 24 so just tell us maybe a little bit about the process that you’ve gone through. I know you’ve spent extensive time meeting with property managers and also the suppliers in the space and just trying to figure out, like, how do we improve what the Association offers, and how do we design for a better future? But just maybe tell us about how that has gone.

Anne Gardner  
Sure, it’s been a great process. First off, and I’ll say that after a year in the role, I can definitively say what I know fills a teacup and what I don’t fills the ocean, still in that regard, but the process is definitely one of listening, you know, being able to help assess an organization where you are and so what are those pain points? What are those areas where we know we have sort of an immediate need. And, you know, vrma was sort of no different. In that sense, we knew we had some challenges in 2024 as far as being able to, you know, reinforce and build the organization from what I think some external forces had considered some missteps or some you know, I heard people say that they thought that vrma had lost their way. And so what I found in interviews, connections, getting a chance to meet our industry partners all over the world, as well as our own members, and doing really deep dives on everyone’s experience with the RMA, including, I think both of you, I think that’s pretty much how I met both of you, is that I just reached out and wanted you to tell me about your experience, and not looking for good, not looking for bad, but just wanting an honest assessment so that we could understand and identify those pockets of similarity, and also, where are the gaps where we knew we didn’t have enough information in order to impanel our board of directors and our leaders who are really driving that change for vrma, what did we need to do in order to put the best data, information and opportunities for re engagement in front of them, so that they could really evaluate the whole picture and put VR may on a path that I think we all agree is new. It’s a bit of a pivot and a change, and I’m still keeping the listening tour going, because to me that’s really integral in any of these first few years of really being part of that fabric of an organization is you have to embody the culture, and you can do the work, and you know what might need to be done, but you have to make sure that you’re really that voice on behalf of a trade organization. And we’re here to move an industry forward and to unify and bring things forward, and you really have to do that in partnership, and it’s about listening in conversation and then being willing to engage everyone, to take action with you. So that’s really been that that next pivot that we’ve done is moving into action with what we’ve learned and not not really sitting on it or hesitating, because folks are looking at vrma for growth and change at this.

Annie Holcombe  
Point, yeah, and I think you and I had the conversation, and I told you early on that in all of my dealings with the Association, it was the first time that I felt as a supplier, just myself, that I felt heard, I felt respected, I felt like there was somebody at the organization that was absolutely listening to my perspective, and that really meant a lot. But on that note, this group of people is not shy about sharing opinions and experiences, which is great. You know, you’re going to get all you’re going to get all the things from everybody. But what did you, you know, probably, what were your biggest takeaways, in terms of, like, what the gaps are that needed to be filled? That’s a great

Anne Gardner  
question, and it’s one that I know I’ve been putting sort of those thoughts in place, but is there, if you will, the playbook of of what has taken VR may from 2024, to now, I would say the biggest thing I heard Annie is that VR may seem to have moved aside, or moved into a time Where we were really accelerating and we weren’t necessarily still engaged in conversation and community, but the VR Ma was moving very quickly, sort of post covid. We had tremendous growth the the October event grew really quickly after 2021 and so it almost sort of took off in a gallop, and seemed to sort of leave some of those critical conversations and really communicating, that was what I heard, more than anything, was that we were not necessarily accused of not doing the work. But does it count if you’re not able to connect it to your mission and vision, to connect it to your members, and really make sure that keep that alignment. And so I think that’s what I learned, first and foremost, is the need for us to make sure we’re communicating with the members, we’re engaging, we’re having conversation, and we’re really just finding out what are the challenges you have day to day, addressing those pain points of transition. That’s what we know now, is that the most value, I think I heard in those interviews and calls was vrma was foundational to my first few years in the business, and this is why, and folks got really specific about what were those areas where they really counted on their industry organization to help them grow their business. And what were those jumping off points as they were transitioning through the life cycles of their business?

Alex Husner  
Yeah, and, you know, I think we look back on the executive summit this year, there was a very big difference between that event and that’s kind of like the I didn’t go to foundations, so that was the first one that I’ve been to that I feel like really infused a lot of the research that you’ve done, and also, you know, putting together a team, you had Rachel and Tom that were kind of driving the content with with the in the program, and they did such an exceptional job. But how do you take what was accomplished at that conference that was, I think, above par for the other VMA events I’ve been to in recent years. How do you continue that momentum forward? And are you using a similar strategy of having Rachel and Tom or other people within the industry that are really working closely, besides your team, to make it

Anne Gardner  
happen? Absolutely, we have no fewer than 50 volunteers are working to organize, guide and produce the VR may 25 Las Vegas event that’ll be taking place in mid October. And so that is a real change. Previously, I think we just didn’t have enough communication, maybe we didn’t have enough input, and we really want our members to understand and own this event, because it is your event. It’s the largest gathering in the industry, and so we really need to make sure it’s representative. And so for us, it’s about engagement, and so engaging very intentionally, very different groups within the organization perspective. And so that’s where I really used a lot of these phone calls and conversations. And those were the first folks I called, because anyone who was sort of honest and candid with me about their their unvarnished experience with the organization, almost all of those calls ended with someone saying that they really wanted to see vrma succeed and grow. And so that, to me, that’s your kitchen cabinet, that’s your bench. And so just really leaning into those who are really, I think, see an opportunity for vrma to be strong, to be a vital organization and to represent their business, because we have a lot of challenges right now where we we need that strength, and we need that unity going forward to help our industry. And you know, we’re celebrating our 40th anniversary this year, and just that next 40 years, that next 50 years, and we’re really just getting started. And so it really has to be Alex, the voice of the member leading the way in.

Annie Holcombe  
Yeah, yeah, I love it. I think this is the first year that there’s actually a committee specifically for the fall event. Is that, am I correct in that I know I’m on it, but I don’t think that we’ve ever had like, a group of people just focused on kind of the look and feel and the overall experience of of the event, and the conversations that have been had have been wonderful. And I think that there’s, you know, definitely I have to laugh, because the the food always came up as as a hot button for some people, but the conversations that were had about ways to make it more engaging, and everybody’s different experiences, you know, from being a supplier or being a property manager attending, you know, the sessions. I mean, I think that we went pretty deep in a lot of those conversations about, like, what didn’t work and what would what could work. You know, it was really about dreaming what, what we could do to make it better. But was that something that you felt was, you know, with the board’s help, was going to be key to making this event sort of pivot in a new direction and really make it everything that it could be. Was putting together that committee?

Anne Gardner  
Oh, absolutely. I smile because, you know, sort of, I guess I would say back behind the green curtain, if you will, is that we actually had a food committee

Alex Husner  
this year. Oh, interesting,

Anne Gardner  
right down to that level. And so to your point, Annie, yes, I mean, we got really detailed, but we got detailed on everything. We got detailed on the things that everybody let us know we weren’t doing right and that had opportunity for improvement. And so we really just focused on what we knew we could achieve, what we believe we could achieve. You know, at the end of the event, everyone will have to tell us if we if we met the mark or not, but really knowing that we had several key areas that were important to address in this next year. The 2025 was really a year where folks were looking and seeing, okay, can VR may bounce back? Can they flex and pivot to be relevant with where the organization is needs to be and change? And so I’ll say that our chair of the board, Jody rifasko, and I, when we sat down together, she she knew, because I I share every single one of these conversations I have, especially in that first six months, I would recap it with our board, because I was, you know, and still am an agent of our leadership. And so it’s, it’s all information gathering. You can call it, you know, op research or something, that’ll inform where you’re headed. But you know, once I was doing that, the leadership knew that we needed to really get re engaged at a very deep level with the members, and that the vitality of our organization, our history, our culture, is about being volunteer led. And so when people were busy after covid, and I saw a lot of businesses do this, you say, well, I’ll come back to it, or I need to focus on and my business, or, you know, we had a lot of owner acquisition, a lot of company growth, and, you know, sometimes it was really galloping forward. And so during those times, your volunteer leadership role may be something that you say, well, maybe I’m not going to have as much time, or a few less hours here and there. And you get that multiplier effect of that and the fact that you know your management team, your admin team is doing the best they can, but nothing replaces folks having that instinct. You know your owner operators in the space your entrepreneurial we mimic your behavior. We follow your lead on that. And so to me, that’s what’s made the biggest difference. I think right now, we just went back home, if you will. Oh, I love that.

Alex Husner  
No, that’s a great explanation of it, too. And so October 2021, you were referencing. That was the show in San Antonio, and I remember that was when there’s a huge influx of solo operators, small hosts, that have joined the organization. How has that gone? I mean, have there? Have many of them stayed? I mean, have they? Have we been pushing more to get more into that audience,

Anne Gardner  
right? You know, that’s a great question. I appreciate it in that the folks who I think came in in 2021 2022 they were coming in purely, I think, as hosts, and they didn’t necessarily have a business plan or a goal or just their own career path. They were, if you will, trying us out. And I think to some extent, vrama might have been trying out the idea of working with the host community a bit. And so I’d say most of those folks kind of came in. They may have started a business, but what we know now, what we know today, in our own sort of analysis and our partners and our research partners in this, is that you know, you have roughly 43% of your I would say, qua. Qualified market is taken up with operators who are operating five or fewer properties and and that’s a US based nationwide. And so when you look at that, it’s not necessarily that we’re looking to sort of grab and only serve that group, but when you look at that outsized percentage, those are the folks who are your future property management firms of tomorrow? Not everyone will be, but these are folks that are on that path to that. And so we want to build educated, really fantastically well trained, well engaged members of their local community, who are part of CVBS, who are part of tourism bureaus who understand the needs within lodging and the role that we have in vacation rental as really just being such a stable part of not only your local tax base, but also just an ambassador for your community. And so we want to help people grow into that, because that’s a lot of detail to cover, a lot of responsibility that we have in our communities. And so we know that’s a growth place. At the same time, the majority of our members are operating 2525 to 100 units, 100 units and up and larger. And so we have a real core of our membership that has grown with us and is looking and has their own business challenges. We’ve got some really interesting things happening at the October event for this segment. And just Where are you taking your business Next, if you will. And so how do you continue to build efficiency and growth and things of that nature, and just where, where do you want to take the business next? And so making sure that we’re looking at, I think both sides Alex is super important for us, because we want to make sure that we serve the folks we have at the table. In addition to being a great example for those that are considering the career down the road,

Annie Holcombe  
why don’t you talk a little bit about, kind of, on that note, the education for this year, because I think that, you know, I was part of some of the reviews of some of the sections, and one of the things that I loved about some of the focus this year was really about forcing interaction, like making sure that people were not just standing up and presenting For the sake of presenting and doing, you know, a slide deck that everybody was just going to be sitting there staring at. And, you know, having somebody talk to them. They wanted to have something that was interaction. So why don’t we tell us a little bit about what the sessions we can expect and what we you know, we think the overall program

Anne Gardner  
is going to look like. I’m glad you mentioned that. So in addition to having workshops that will start on Sunday, the 12th of October. And we have some really interesting new topics there. We also have some deep dives, if you will, some workshop level programming that we have during the actual conference. We also have just some quick hits, if you will, some just small doses, almost micro courses, if you will, for sharing. And so we really wanted to move it away from the panel presentation going on for 45 or 60 Minutes, where you don’t have a lot of interaction, because we know that one of our biggest challenges Annie is to make sure that someone can come to this event, that you can either be new or newer in your career, you may be the only one or one of two or three who are representing your company or firm at an event like this. And so how do we bring together a year’s worth of knowledge information? How do we extend the trail on that after you’ve been at the event, and so being able to make sure that we have those deeper dives and those exposure and networking opportunities. Because one of the best things that I know I take from events when I attend them, is who are the people I met, and are they in a similar life transition point, business challenge? And so we wanted to really open up the program so that you have more opportunity to meet one another and dialog and identify people who may be facing a very similar business situation or business challenge, or maybe are exploring the growth opportunity that you’re exploring, because we know that the value is in what you take from the actual in person event, and how do you use it year round, right? And even down to the level of introducing the conference recordings, we know it’s not novel, you know, but it’s just one of those areas where we knew we wanted to personalize the event, give opportunity to meet and have connections, so that you can then take the event with you after, yeah.

Alex Husner  
And, you know, I think a big part of the success of any of the events that we go to is the venue. I mean, the food too, but the venues, it plays a big part in it. And I’m curious to hear, I know we had VMA in fall of 2022, in Vegas, but it’s at a different it’s the same property, but like a different part of it is, what I’ve heard is that true,

Anne Gardner  
it’s actually a whole new property. So when we were. When we were in 2022 we were in the Caesars Palace proper, the casino hotel there. And so our event actually has grown. It actually wouldn’t fit in a single venue property. And so we are, we are hosting this at a beautiful, relatively new facility that is built specifically for events like the RMA. And it is called Caesar’s forum, and so it is adjacent to our hotel and a couple of other properties, and it’s across the street from the Caesars Palace. But I think you will you both know that when you say you’re in Las Vegas and you’re across the street, that could be a 30 minute walk over and a few cross signals. But it’s really a space that was designed and built just specifically for this level of networking, this level of learning. You know, we have eight concurrent ballrooms. It’s really unusual to be able to say you have eight ballrooms right to be able to have your learning as well as your Expo. Yeah, it’s really an extraordinary facility and lots of indoor and outdoor space. I remember

Annie Holcombe  
talking to some of the board members when they got back from the site visit, and they were all very excited about the fact that we didn’t have a scenario where, like, suppliers were so far away from all the sessions and everything was going to be working more together. And I think that that that just, you know, that spoke to me like, Okay, this is going to be a much better event. So Anne, why don’t you tell us a little bit about the keynote speaker that we had this year. Is a pretty big name. I know that I had kind of heard everybody kind of say, Oh, wow. You know, they took notice. So it feels like it was a, it was a change to get somebody that was recognized along multiple kind of genres of speaking. But I, you know, I don’t know what the impetus was to get someone of his caliber to come speak with

Anne Gardner  
us. I think I’m glad you took notice. I’m glad other folks have because I think this was, you know, a real, I think, Hallmark moment for us, you know, as vrma has our 40th anniversary, and as we sort of are navigating, if you will, that bridge of hospitality and the fact that we are a preferred mode of travel lodging for an entire generation right now who is coming into their own and into their spending, and folks have options and flexibility in travel preferences. And so to be able to have the opportunity to welcome chip Connolly to the event, really, I think, signifies the the role that vrma has and that vacation rental management, professional management has in the overall sort of lodging and hospitality space. We were fortunate. You know, all good things come through relationships and sometimes referrals. And so we had a great opportunity. One of our planning committee members, Michelle Marquis, had an opportunity to help make an introduction for us. And so we’re super glad. We’re super excited to have him. And as a matter of fact, in addition to his keynote on disruptive hospitality and just sort of challenging that he’s also going to stay with us later in the day, and he actually has a breakout session as well. So we have eight ballrooms concurrent for sessions at this facility, and so he’ll be in one of those afterwards as well. So he’s going to specifically put that presentation to vacation rental industry. And it’s about, how do you cultivate and develop your innovation within our industry? And so we’re, we’re just real, super glad to have him part of it. Yeah, it’s

Annie Holcombe  
exciting. It’s exciting that the fervor behind him is, I mean, I think it’s, it’s good and people are interested. And that’s exactly what we wanted, is to have people be excited about coming to keynote. I mean, we know Alex isn’t going to get up that early, but I’m going to try

Alex Husner  
that early,

Anne Gardner  
but to that point, you know, it’s through the work of our members and our leaders, you know that are really, I think, making the difference. And so you can take that, that opportunity, that introduction, that resulted in our great keynote, get, I think, for this year, and just it’s the spirit of what that looks like, and what does engagement really mean, and it’s making such a difference for us. And we heard that as far as, I think you’d asked about what’s different and what’s how are we coming forward and bringing this event, which is our sort of our hallmark event forward. And you know, this year we have 12 tracks, you know, 12 distinct tracks that are pivoting everyone through various business stages that we know based on our research now are the areas that they look to vrma for guidance, and they look to their peer network for guidance. And so a lot of those areas where we knew people had needs and wants as far as training, and how do we make that stick throughout the whole year? So we curated a lot of this content, and we have sort of gone to the well of our industry in that sense. And so we’ve also learned from our partners in they’re also producing events and sort of where they were. Where that litmus is. And so we know it’s a fast moving things are changing. And so we’ve really moved away from what I think people used to think of as a pretty stodgy and historic sort of abstract presentation. Write up a session months before and then wait to find out with a letter, an actual letter, if you were going to be part of the program, and then you were really locked in. And we know that our industry and everything is just so much more dynamic than that, and for us to be responsive, we really have to bring together our folks and just listen and go serve it up.

Annie Holcombe  
Yeah, I think the one thing that I’ve seen being part of the committee and then some other committees, is that there’s a lot more interaction between the committees than there has been. The committees had been operating in kind of silos. I still think there’s a lot of opportunity to have more engagement between them, but I think that there is definitely more sharing of ideas that you know, the fact that the committee for the conference did look at sessions, and there are some people on that committee that are helping with the curation portion of it. It’s just it’s keeping things exciting and fresh. And I think there’s just having a different perspective of how the conference can and should be and could be, and really kind of dreaming about these, these wonderful changes to move us forward. And I’m like, for the first time in a really long time, I’m actually, like, super excited about it, one because I won’t be standing at a booth so good from that perspective, but I am really excited. And I think the people that I’ve talked to after people went to foundations in the spring, and then obviously the exact conference, people are feeling that momentum of the association moving forward in a good direction, and that change is coming, and change is good, and we all agree on it. And so I’m really hopeful that everybody that does attend this year will will feel the energy that has been put in it by not only your team, but like you said, the 50 plus volunteers that have been working on it

Anne Gardner  
absolutely and I know you will have a little bit of a different role at the event this year you’ve got, I know, an extra day added into your own conference schedule, because we were really pleased to learn that you were just elected to the VR ma Board of Directors starting in October at the event this year. So congratulations on that.

Annie Holcombe  
Yeah, thank you very excited. I you know I was, I have to admit, I was a little little hesitant to do it, but then I figured if I didn’t do it, I’d always regret not like going for it. So I appreciate everybody’s support and confidence to vote me in, so hopeful that the next two years I can make some impact. And, yeah, help change. Things are exciting.

Anne Gardner  
Alex, can we pivot a question to Annie? I’d love to know, sort of, what you absolutely what do you see Annie as opportunities for us? And you know what, what you see sort of on the near the near term horizon, if you will.

Annie Holcombe  
So it’s interesting. So like, specific to the conference, I think that the vendor Hall needs to be completely blown up and redone. I have lots of ideas on that, so, yeah, so I think that that’s one that could make a really big change for perception, but also engagement. But I do think, and it’s been a lot of conversations that we’ve had on the membership committee, is that you know, kind of what you were alluding to is, is tapping into the DMO, CVB chambers of commerce, and we, we’ve known for a long time that that’s kind of an opportunity to have kind of boots on the ground evangelists in these markets for us. But one of the things that I know you and I have been working on is to do a survey out to these people to understand, like, what do they know about brma, but what? How does the vacation rental industry impact their market? You know? Because I think we’re making a lot of assumptions based on the membership that we have, and certainly they’re probably right in some areas, but I think we just there’s a lot of markets out there that we don’t have any touch points in, and we don’t have anybody in the market that can talk about the association and the value that we bring. So I would like to see, you know, us get data from that survey and really be able to make some great changes there to grow membership. And then, you know, to your your other point about, you know, where, kind of the largest bucket of opportunity sits in growth, it’s one of the things that I’m now focusing on with my new business, Annie and CO, is that I want to really tap into education for these people that are new to the business since covid, because they don’t know what the real world is like outside of, you know, the last couple of years. And so now they’re really hitting kind of, we’ve joked, but, you know, we’re going to go back to 2019 and it’s not that you want to go back, but that’s the last year that anybody has that was sort of would be deemed normal. So there’s all these people that entered the space that don’t know what normal, can, should, could be. And so I think tapping into those people and getting them, as you know, someone said previously, like the tents big enough for all of them, let’s, let’s invite them into the tent. And we just haven’t been inviting them. And I’ve been talking to some managers that are smaller. And the amount of information that they don’t know and that they have had kind of poor guidance on it has been a detriment to the association, I think, in, you know, from an advocacy standpoint, from a messaging standpoint, so that tapping into the small, the smaller operators, where I really, really see our ability to grow and prosper in the in the industry, that’s great.

Anne Gardner  
That’s great. All good points, right? Yeah,

Alex Husner  
work to do, yeah? I mean, I think, you know, in associations that I’ve been a part of, and I served on VMA board for about a year and a half last year and beyond, but, you know, one of the things that we’ve talked about was similar what Annie mentioned, of like, how do we partner more with these different associations, whether, you know, at a local level, some of the other trade associations, both us and and abroad. And I think so far this year, I’ve seen and I’ve seen you at several conferences. You were at VR nation, you were at the vacation rental Women’s Summit. I’m sure you’ve been to some others too. But I think it’s really, it’s big. It’s important for us, us as vrama, to show our support for these other associations too. Because at the end of the day, you know, we serve different audiences. There is, of course, some crossover, but there’s always going to be some people that can’t make every show, and if they can’t make the RMA, but they can make VR nation, maybe next year. It’s the it’s the opposite, or maybe they go to both. But I mean, there’s values, and, you know, differences between the organizations. And I think when we work together, we’re stronger. And it’s less about seeing, you know, each different entity as competition, but it’s about, how do we grow the awareness of the professional industry? How do we get there’s how many 1000 vacation rental companies, like 18,000 US somewhere around there. I mean, there’s only, you know, our membership is much lower than that. So it’s like there’s so many more people to reach, and that’s, that’s how you reach, you know, to Annie’s point, it’s the local connections, you know, beyond just those trade associations, but the chambers and realtor associations. And, you know, I think that’s going to be where the growth comes, and how you figure out how to, how to work that together so that it’s a great partnership for both sides.

Anne Gardner  
Absolutely, I will, I will take all those suggestions to the bank on that, absolutely, absolutely, because it is true. There’s and I do have some interesting things too, that I can, that I can share with you is that we do know that affiliating with vrma increases your bottom line. You know, we know, we have an annual study that we do with our data, one of our data partners, key data, and so they work with us, sort of behind, behind the scenes, and we look at the last year, and we this year, we looked at the last four years, and, you know, just where we’re able to demonstrate and see that those who are part of vrma, you know you are learning, you are creating a community, you are growing. And so you know the results in your business are are 100% there as well. And so we have that evidence, those proof points. And so you have longer booking windows, and you also have larger and you have your paid stays are higher, as well as you have the length of stay is longer. So you have really three really strong points where, by virtue of being part of your community, part of your industry. We know your business is improving, if you will, and you have that opportunity. How are we as an industry protecting the industry, you know, fostering its ability to grow unfettered and to be able to, you know, work within markets and so to your points, Annie, about the smaller operators and that outreach, that’s something that we’re really putting a lot of focus on right now, and we’re being more proactive as an organization. And where are those areas where we know that there’s vulnerabilities, or where there’s, you know, challenges that could happen, or where it’s going to be an area that could be a good case study, if you will. And so we’re we’re starting to sort of differentiate ourselves in that we’re in a position to be able to do this work, and so it’s right and appropriate and needed to do these studies in this work. And so that’s a key part of what we’re doing with our newly relaunched Advocacy Fund. And so we know that our partners in the industry have funds. They’re doing fundraising, and they’re really specific in their channels, as far as whether it be capacity building and helping to grow the small and regional and statewide organizations. And so we know vrma has a role there. It’s a companion role we’re all there to lift, because the industry is is still in its early stages, if you will. And so we’re evolving just so quickly to where we need many hands and we need many voices in order to represent

Annie Holcombe  
us. Yeah, and I love, I love the the approach of that we can work together side by side in partnership, instead of having this, again, this kind of siloed mentality of like, each, you know, each, these entities have their own discipline. In there, not to, not to come together, to, you know, to partner. And I think that if we, we partner with all of these things, we’re just like you said, it’s like the rising tide lifts all boats. I mean, we’re going to be better as a as an industry, and we know we’re, we’ve got a lot of headwinds related to, to, you know, regulations, right? You know, some markets, it’s the hotel lobby, you know, and I think that we need to befriend them. I mean, that’s, let’s face it, the hotel brands are stepping into this space, so we need to, you know, I don’t, someone said to me once, it’s like inviting, you know, the wolf in the den. And I was like, you know, they need to be in. They’re they’re stepping in, whether we want them or

Alex Husner  
not, nothing can be improved by not working with them, right? Get any wars, so, yeah, I think, and we need to have a seat at the table, you know. I mean, if you’re not on the table, you’re on the menu. And as an industry, we’ve learned that, you know, in so many cases across the country. So I think the more that we can, you know, try and again, find that mutually beneficial way that it benefits both sides to work together, then that’s where the win is well, and we are super excited for vrma 25 and there’s no better place to have a conference than Las Vegas. So I think a lot of people are really excited, and just feeling the momentum of the past events that have gone really well this year, and just the opportunity to connect and network and learn. So if anybody wants to get in touch with you or learn more about brma, or potentially attend the show if they haven’t already booked, what’s the best way for them to get in touch with you?

Anne Gardner  
I’m pretty easy to find. I’m on LinkedIn, and so if you’re if you’re in channels or whatnot, you you usually can find me here and there. I’m also really accessible to get to. And I encourage everybody to reach out. Tell me your experience story with vrma at a Gardner, a G, A r, d, N, E R at V rma.org, so those are probably the two easiest ways to to hear from me.

Alex Husner  
Awesome. Okay, well, and if anybody wants to get in touch with Annie and I, you can go to Alex and Annie podcast.com and until next time and until Vegas, we’ll see you there.

The Danger of OTA Dependence: Building a Strong Direct Booking Strategy with Mark Simpson of Boostly

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When Airbnb changes its policies, the ripple effect can shake operators everywhere. For many, the problem is deeper than one policy update. Relying too heavily on a single platform leaves businesses vulnerable, and the cracks are starting to show.

In this episode, Mark Simpson, CEO and founder of Boostly, shares why now is the time for vacation rental operators to double down on direct bookings. Drawing from more than a decade of helping hosts grow beyond OTAs, Mark brings practical steps that any operator can put into action.

We cover:

  • Why overreliance on OTAs creates long-term risk for property managers
  • How to turn guest data into a foundation for repeat bookings
  • Simple strategies that work even without a large marketing budget
  • Ways to use referrals, user-generated content, and email campaigns to build stronger relationships with guests
  • What Boostly is creating to make direct bookings more accessible and effective

Mark also opens up about the importance of creativity in marketing, sharing real stories of campaigns that cut through the noise at conferences and online. His approach proves that building direct channels is not only possible but powerful.

Connect with Mark:
LinkedIn: https://www.linkedin.com/in/mrmarksimpson/
Website: https://boostly.co.uk/


Transcript

Alex Husner  0:00  
Welcome to Alex & Annie, the real women of vacation rentals. I’m Alex, and I’m Annie, and we are joined today with Mark Simpson, who is the CEO of Boostly, Mark, it’s so good to see you back again for the third time.

Annie Holcombe  0:12  
Yeah, thanks for having me back. Can’t believe you actually came back for a third time that yeah, punishment,

Mark Simpson  0:18  
and it’s the punishment,

Annie Holcombe  0:22  
and it’s late there, so it was nine o’clock,

Mark Simpson  0:25  
nine o’clock, 10 past nine. Just got the kids to bed, so it’s the perfect time just to have a little chat and catch

Annie Holcombe  0:30  
up. Awesome for our listeners that don’t know who you are, why don’t you tell us a little bit about you?

Mark Simpson  0:36  
Yeah, sure. So I created this little company called Bruce Lee, nearly 10 years ago. Now, after being born into the world of hospitality, I grew up in a 200 acre farm stay Bed and Breakfast, you know, worked full time in it from 2011 to about 2016 17. We eventually sold that business, and, yeah, for like, the last 10 years with Bruce Lee, I’ve just been helping host when it comes to, you know, direct bookings, whether you’ve got one property or, you know, we’ve got some clients now we’ve got a couple of 100 properties. We just give you, I say, like, my liver pitches, the tools, the tactics, the training and the confidence to increase your diet bookings without relying on these online travel agents. And, yeah, that’s what we’ve been doing, and it’s just sort of grown crazy over the last, I’d say, the last five years. It’s really sort of like ramped up, and I get to now travel the world, speak at events and all this cool stuff. So that’s my little me. The interesting

Alex Husner  1:27  
thing is, too, I bet, when you went into this business, that you, I mean, you knew what the situation was at the time that, like, there was a need for this, and there were, there were issues, but you probably had no idea how your business model would continuously be fed by the engine. Is Airbnb and the, you know, just problems and issues that people are having and how they’re looking for other options. But it’s been a wild ride. I mean, that last time we had you on was three years ago. I mean, that’s, it feels like an eternity compared to all the things that have happened in the world of OTAs since then.

Mark Simpson  1:57  
Yeah. I mean, truthfully, like, the way that I started the business was just for my little hometown in Scarborough, because there I just, there was no help from the from the local tourism board when it comes to, like, marketing and sales, yeah. And, you know, it’s a funny thing as soon as you start putting stuff on the internet, like people all over the world can see it and and want to be part of it. And I just started a little Facebook group, and, you know, I saw people requesting to join and and they’re off just from all over the world. And you know, when we got to 1000 members in that group, I was like that, there’s got to be something here. There’s got to be like a business here. And again, it’s just evolved over time. And I’ve sort of been on this sort of one, one man mission to piss off the OTAs as much as possible in any given chance that I get, and, yeah, it’s been a fun ride.

Annie Holcombe  2:43  
Well, that’s where we I actually wanted to get started was pissing off the OTA. So I’m sure you’ve been called a lot of names in some private rooms, but you like to poke at Airbnb specifically. And there has been a lot of changes the last, I would say, the last three months, specifically with Airbnb, specifically in the US, but I think globally. And so I think people lean on those that have always been poking at them to say, like, what am I supposed to do now? And so I know that’s the conversations that I’ve been having with people. Is they’re just their head is about to explode. It just feels like every time they open an email from them, there’s a new policy or a new change in it. And once again, just feels like another layer, or another statement of we’re not friendly to the property managers. We’re only friendly to the guest. So wanted to get your take on it, and kind of all the things that have happened, address them, and maybe get your thoughts on where we’re at with that channel.

Mark Simpson  3:34  
Yeah, it’s mad. I was trying to take the summer off.

Annie Holcombe  3:39  
They had other ideas. Yeah, every

Mark Simpson  3:41  
single week there was just something and yeah, obviously I like to react, and I do feel like it’s I try and keep it fair. I poke the bear with booking.com as much as VRBO as well as Airbnb. But yeah, this summer, Airbnb have seemed to be pivoting to more of a traditional OTA model. I feel obviously, Brian Chesky has mentioned it time and time again, that as good as their business is for every one night booked on Airbnb, he said somewhere like nine bookings are made on hotels. So obviously hotels is the play. Where do hotels most majority live is booking.com and Expedia. So that’s obviously where their whole sort of focus is going. And the changes that have been made, if you look at it from like a 60,000 foot view, it’s obvious that they’re trying to change their model their back end, so it mirrors what a traditional Ota booking.com X BD would look like. But when you do that, and you change the rate that they are doing, they are going to annoy a lot of people, and the people that they are upsetting the most are these, their sort of Avatar. Their hobbyist hosts, as we call them, all the smaller operators who have maybe been, you know, we talk about fees like 3% they’ve been paying 3% happily paying, paying 3% all of a sudden, they’ve been told it’s gone up to 15.5% which things like that, and then cancelation policies and things like services coming in, where. She’s like, you know, you give up all of the, all of the, all of the juice without the squeeze. You know what? I mean? It’s like, you get nothing back, and you take all the risk on board. And, you know, it’s, I’ve heard so many people talk about it, so many people give their opinions. But what’s really interesting to me is some of the Airbnb gurus, the Airbnb like number one fans, they’re actually now going, well, hang on a second. What is this? And that’s been fascinating to me, and I say Bruce Lee on the back end is just, I was saying offering our call calendar has never been this full. You know, it’s insane how busy our call calendar has

Alex Husner  5:32  
been. Yeah, it’s like you’ve been pushed and bullied so long that finally, eventually, like, you might take it for a little bit, but then you then that last one is just kind of throws you, know, really, really over the deep end. And I was just on a call with a pretty large operator in South Florida today, and they were asking about if I thought that Airbnb was going to make it mandatory for hosts to do a 24 hour cancelation policy, and if that would be different for large companies versus small companies. And I said, I don’t know. I don’t have a crystal ball, but I do have somebody coming on the podcast later today that might know a little bit more or have maybe some insights. But have you heard anything on that side?

Mark Simpson  6:09  
No, I feel, I mean, Airbnb will always try. And as you’ve said on a number of podcasts, I was, I was listening today, one with Dennis Shaw earlier, earlier today. And you know, he’s, he’s probably more connected than than all of us industry, and I feel it’s 100% that podcast was, was amazing, and it’s basically confined to everything that we’ve been thinking about is that Airbnb is their priority, is the guest and their shareholders, and it’s, unfortunately, the host have to sort of put up with it. But it all boils down to is that, you know, if, if you are so reliant on this one platform for your whole revenue coming in, then it’s, it’s your own fault. You know, I’ve said this a lot like, my issue isn’t so much with Airbnb. It’s not so much with Expedia, with booking.com, my issue with is with the host, the host who is so reliant, who refuses to do anything about it. And you know, luckily, now there’s so many resources. There’s fantastic podcasts and YouTube channels and books and everywhere wherever, is so much education that you can get for free. But it really is not an excuse not to learn how to do these, these things. So when these do these policy changes, do change, you can just go, Oh, that’s cool. But, you know, you’ve got this whole direct booking funnel and whatnot. But bringing it back to the 24 hour thing, I’ve not heard, I’m not privy to it, it wouldn’t surprise me to be honest with with all of the changes that are going on behind the scenes. But like I say, Nothing is surprising me at the moment with the things that are coming out from Airbnb, HQ,

Annie Holcombe  7:39  
at the moment, kind of touching on, you know, some of these hosts, and you and I go back and forth on Instagram a lot about some of these, the influencers that are the get rich quick guys as Alex and I always call them, you know, that they’ve started to take notice. And I think it’s like, I also fault them to some degree of like, giving people this false sense of what reality actually is. I’ve been meeting with a manager, and, you know, she said to me very, very pointedly right off the bat, like I am too reliant on them, that’s all I have. But then I looked into like her PMS, and her PMS only has connectivity to a few channels, so she doesn’t have a lot of opportunity to kind of diversify. They don’t offer a channel manager, so she’s very limited in what she can do. So some of it, you know, some of it, is a technology problem, but some of it is the messaging that gets in front of these people, and that’s all they’re seeing, is that, like, it’s an Airbnb empire. It’s you’re building it only on Airbnb. So they think it’s okay, like, almost like, this business is going to be their friend forever. And now they’re all seeing that maybe that’s not exactly the case. So I’m wondering, like, in your mind, what do you think some of these influencers who have staked their reputation and their business on this Airbnb Empire theme? You know, what do you think they’re going to do with

Mark Simpson  8:53  
this for every influencer that is out there on Instagram for the last sort of five years, they’ve had me in the comment section and then the message is trying to sort of educate them. And you know, to be fair, a lot of have listened. And, you know, I’ve ended up working with a lot of them, but it has been very, very funny and interesting. Like, there’s different things that become very popular topics. And you know, whether it is the shiny NFT coins or cryptocurrency or whatever that is, the flavor of the topic of the month, or if it’s this sub two thing that goes around the states, obvious, all these different strategies and whatnot. This year seems to be the year where everybody wants to talk about direct bookings. And it’s been fascinating to see people that maybe a year ago, they didn’t know what a direct booking meant, but now they’re talking about it like they’re the experts in it, which is really fascinating. I totally understand where there’ll be people talking about and just because they’re good at Instagram or YouTube, that they will get the attention. But I feel like what is really, really important for any host that is watching this or listening listening to this, is there are some fantastic resources out there, and I would never try and stand here and talk about the sub two movement or talk. Talk about arbitrage or talk about whatever, because that is not my skill set. I can talk about marketing because I’ve been doing it for Well, since 2011 and when it comes to Derek bookings, that is all I really love to talk about. When it comes to these other influences, and what they’re sort of been talking about, and they’ve literally put their nail to the mast on on Airbnb, and Airbnb being in the only channel, it is fascinating to me now to seeing how quickly they start talking about these, these, uh, things called direct bookings.

Alex Husner  10:29  
Yeah. I mean, it’s definitely something that has been built with awareness of why people are now finally understanding this is something they didn’t be cognizant of, and building a plan. But, you know, I, I get this question all the time from smaller hosts that, you know, they know, my background is mostly working with larger property management companies that have hundreds of units, and we can very, you know, not more easily, but, I mean, there’s, there’s a huge expense to it, but a company has a lot more resources than individual host does to drive marketing dollars and demand to a property. But a lot of people ask, you know, how do I how do I do direct bookings if I don’t have a big marketing budget? And my my response is, and I’m very curious here, what you also recommend mark, but it’s get as much of the lowest hanging fruit as you can. So if you’re whether you are you’re not, but if you’re in a market where you get a lot of direct like repeat business, for sure, make sure that your information is all over that property, that they know the brand, that there’s QR codes, that it’s super easy for them to stay in touch with you, and, you know, create an experience that people are going to actually remember and that makes them want to seek out, coming back to you. But you know, the not being able to get guest emails Now, if you’re just relying on Airbnb, also creates a lot of friction there. So it’s like, it’s now kind of the onus is on you to make sure that the guests go out of their way to follow you if you want to stay in touch with them. But curious, your thoughts on how smaller hosts really can move the

Mark Simpson  11:53  
needle? Yeah, so it’s a great question. And in 2021 I remember clubhouse being really popular, like the audio app that everybody was on, especially if you had an iPhone. And I used to sit in those rooms and I would join in. And these questions were coming up so much, even back then, like, you know, I want to do, you know, Dow bookings. Where do I start? Yada yada yada, which is why I put that book together, the book that I play, book, the one that I spoke about three years ago when I came on the podcast, which, which changed everything like for me, and there’s 101 tips in there. And the cool thing is about that is that majority of the tips in here don’t cost a penny, but what it really boils down to is data like you’ve got to get the data of your guest as soon as possible, whether that is through Google Forms or stay fi or QR codes, like you mentioned, as soon as you can start getting that data, it changes a lot. And we’ve got people within the boothly world, our booths community, our boothly customers. And whenever they join boothly, they get a CRM. So the CRM that we use is basically built on go high level, and you can import your contacts, from your PMS, from stay five, from wherever you get them into there. And we’ve got the agency level so I can see everything from like the agency level view. And it is fascinating to me, the customers of ours who do amazing work with direct bookings, as in going from zero direct bookings to maybe 50% direct bookings within a year or 18 months is the ones that are building the database but then do something with it, as in sending campaigns, sending SMS is sending emails, whether it’s individual or broadcast, they’re the ones that are truly doing doing work with it and making that Data go to work, the people that struggle, the people who don’t improve their direct bookings, even when they’ve got like a real snazzy direct booking website that’s integrated into their PMS of choice are the ones that don’t collect the data. But maybe there was one client who had 7000 emails, but they never sent an email.

Annie Holcombe  14:00  
They’ve got them, though,

Alex Husner  14:03  
I’m taking emails to the bank Absolutely.

Mark Simpson  14:06  
And I said, so we crafted this email that was built together with an AI bot that we had, and they sent out to the 7000 people. And it was a very friendly email. It was like the question was, do you know anyone? So basically, all of these guests that we sent it to had stayed with them in the past six months, and it was all emails that they had gathered through collection of Google Forms, stay, fire, etc. And this email was so easily put together. It took two minutes to put together, and it was just asking the question to the guest, hey, we loved having you as a guest. Thank you very much for staying with us. Do you know anybody that is coming to this area. It was such a simple question that to ask, and it wasn’t a massive tourist destination. This was like a, like a city in the United Kingdom. It was Chester. So it wasn’t like, you know, when you think of the UK, you don’t think of Chester, but it’s a kind of cool little light city. And that email generated so much rest. Revenue just off the back of it from people recommending people to it. There was a couple of business guests that they got in contact with. They put them in touch with their head office, because the head office was sending lots of people to Chester, but this guest in this client didn’t know about and it was just at the back of an email. So it was a case of a getting the data, B, doing something with it, and that’s what it literally, it all boils down to the people that I see that do data and email and communication, the best wins, basically.

Alex Husner  15:27  
And quite honestly, I would say that same issue applies to large managers just as much as small managers. That if you have a huge email list, if you’ve been in business for a long time, and it’s just sitting there and you’re not utilizing it, it’s, it’s also doing, you know, good, right? But that’s a really interesting idea, to see who they’re you know, who they would recommend you to. Was there an offer or, like, a referral bonus, or anything attached to it?

Mark Simpson  15:50  
Yeah, I’m a big fan of dangling the carrot. So if you’re going to ask the question, you got to have the incentive. And if you do it on a smaller scale, and I talk about a smaller scale, is that I always say that your phone book, your contact list, when you’re starting out as a host, is so powerful because you’ve got people in there that know, know you, love you and would want you to succeed. And a lot of people don’t even realize what you do for a business or a job or that you’re starting this new venture. So I always say just, just blast it out, text 10 people and just say, Hey, if you know anybody that’s coming to the area, and if they book and they reference you, I’ll send you x and if you know the person to dangle that carrot, even better. I’m a big Liverpool football fan, you know. And if someone wants to entice me, just offer me Liverpool football tickets. But even if you don’t know the person, you can just say, you know, I’ll send you $100 in amazon vouchers or cash or whatever, you know, you incentivize them to do it, and when you incentivize people, they’re more likely to to act. And that’s what we’re doing in a thread in that email Fred that we sent

Annie Holcombe  16:50  
out. Yeah, so you, I know one thing we talked about previously, and I’ve talked to you about it before. You’ve you’ve customers literally all over the world. You’re working in on every continent. Are you seeing anything that works better in one region than another? Or is does it work generally the same everywhere? I feel like Asia is one of those. It’s always kind of an enigma to work in. But what are you seeing?

Mark Simpson  17:15  
Sales and Marketing I feel just works all over the world, because at the end of the day, simple sales and marketing tactics work whether you’re a bigger company or a smaller company. You do have different things to contend with. Depends on where you are in the world, 100% and obviously, as well, Northern and hemisphere and southern hemisphere, you’ve got different times of the year where things work differently and others. And you know, this is before we even get into like regulations and tourism and licenses and etc. But when it when it really does boil down to sales and marketing, which is what this is, I think the same practices run parallel with hospitality, if they run parallel with around the niches, but it’s exactly the same. You can pick it up and put it into things like personal trainers, or you can put it into like barber shops or brick and mortar businesses. It’s the simple sales and marketing tactics that have just stood the test of time. We just repackage it and do it a little bit different, because it is the world of hospitality, and I always say that we’re in such a really favorable position in hospitality, because we’re in the industry of making memories. When, when we sell our product to the people, the guests, they are literally making memories. They will talk about that vacation that stay for forever, for the test of time, like and because of that, we are in such a favorable position. But also, as well, bringing it back to the OTAs, we are in very lucky position that we can literally just list our property on these free channels, booking.com, Expedia, verbo, Airbnb, and be pretty much guaranteed to get some revenue coming in. You know, Annie, you’re about to go into the world of, you know, solopreneurship, and there’s, like, there’s nowhere that you can go and list your services on that you’ll be guaranteed to get revenue in you know what I mean? You’ve got to like, you know, you build the brand. You’ve got to, like, do the market and do the sales, etc. So we’re very fortunate with hospitality, but at the same time, like, the curse is, is that, because it is so easy, so many hosts, especially smaller hosts, they just get so reliant on that one platform that will just drive them revenue and don’t do anything else, and that’s like, where the problems occur.

Alex Husner  19:23  
Yeah, you hit the nail on the head with the friends and family thing. And I know that ties into the email campaign idea that you did, but in my history, I mean, there’s been nothing that can more easily set you apart from your competition in the market. Is pretty cost effective to do as a program, but is to generate or to get your guests to submit user generated content. And I think where companies and hosts get stuck around that is just literally in the process, and the technology to be able to make it happen, facilitate it, get usage and rights to the pictures. But when you think about it, like you said in your phone, there’s probably in your. All of our phones, there’s a bunch of people that demographically are very similar to us, so you have to think about them the same way that it’s like if you incentivize your guests to share a memory or a picture from their stay and share that to their friends and family. And you’ve got some contests and, you know, gamifying that process, it’s just amazing what I’ve seen for success in that side. But it’s, you know, it’s one of those things that I think a lot of companies look at it as a nice to have, but the companies that really utilize it, it’s actually a key differentiator between them and the competition in the market. Yeah.

Mark Simpson  20:32  
Can you think about, when do you mostly post on social media? Is when you’re on vacation, because you want to show off to your friends and families at home that you’re on vacation. And the way that operators fall down is that there isn’t some form of signage or somewhere in digitality where it says, when you take pictures and you post it online, tag in our handle, or tag in that you are here. And for everybody that does, we’ll send you x like we used to do at our farm stay business is we used to do a monthly competition on social media. And this is back in 2011 2012 when this was all very new. But we would put on the on the in the property would have this, this cool little laminate that’s saying, when you take a picture, you upload it to social media, tagging the granary. Every month we pick our favorite one, and you will win a bottle of wine. It was so simple, so easy, but we gamified it. And everybody would go on Instagram and Facebook, and they would tag us in and then we would use those pictures for our social media posts. Yeah, exactly, yeah. People buy from people. People want to experience. They can see themselves staying at the place through other people on social media. And if they post it on Facebook and they tag you in and we all dream of working with these influences that have got hundreds of 1000s or millions of followers, but the best influences the friends and families of the people,

Alex Husner  21:54  
100% Yeah, yeah, 100% and this happens to me all the time, that even if it’s not somebody that I’m like, close friends with, but if I saw somebody that went to Grand Cayman, and I saw pictures, and I was like, God, that looks so beautiful there. And a month later, now I’m thinking about going somewhere, and I’m like, I remember that person went to Grand Cayman, I will definitely reach out to them and say, you know, where did you stay? What did you like to do? Even if it’s not somebody that I’m like, a close, close friend with, but you’d rather get advice from somebody that’s close to you, but even just people within your network that your network that like you, you know, a little bit more than just looking on a website. I mean, there’s a certain level of trust if you can, you know, see a little bit more about a person. But, yeah, I love that you do that. That’s great kind

Annie Holcombe  22:34  
of on the on the influencer note, one of the things that I think that you have done is influence people to think outside the box. You do a lot of kind of guerilla marketing around things and some unique, unique things. And one of the things that caught my eye that you did this year was you weren’t able to attend a conference. It was the SDR wealth conference in Nashville, and that’s always known, depending on what side of the industry you sit on, it has a flavor, and some people like that flavor and some people don’t like that flavor. And I’ll say it that way, but you weren’t able to attend, so you did these wanted posters, and so I really never got a chance to talk to you, and so we were talking about it off camera. I’d really like to understand what the impetus was behind that. And like, you know, what other other types of guerrilla marketing you’ve done for events and kind of, what you you know, it feels like it’s encouraging people to really, really do different things to get noticed. But you’ve done the stickers on the bathroom walls, yeah, done a couple of different things, so maybe talk us through that process.

Mark Simpson  23:30  
Yeah, I like to mess around with marketing. I like to be a guinea pig at marketing and and, you know, I’ve, I’ve always loved Richard Branson, and I love reading all of his books and how he would go and launch one of his virgin products, he would do something like crazy, like guerrilla marketing to get the get the attention. And I haven’t got the budget of a Richard Branson, but I I kind of look at what other people are doing outside of the world of short term rentals, and I try and bring it into this, this world. So toilet stickers, prime example when you’re at an event, and I used to do this, and I would get help in the women’s bathrooms, but basically, I would get these stickers done, and these stickers would have a QR code on it, and I’m always thinking, well, when do you have your phone out? Is when you’re sitting down on the toilet. And I would go into the men’s cubicles of any event I was speaking at. And I’ve done this at Verma in Orlando. I’ve done this SEO wealth. When it was in, like, the saloons at any event, I would just, I’ve got stickers, like, literally behind me. Now it was like a bag full of stickers. And I would go into the men’s toilets, and at the start of the day, and I was going stick them all on. And basically, the copy would change. I would AB test. The copy would vary from, would you like to flush Airbnb down the toilet. The copy was like, the guy that Airbnb don’t want you to know about, or the guy that the OTAs don’t want you to know about, with a QR code that they would scan. That QR code will go to my link tree. And the cool thing about link tree is it’s absolutely free, and then you can change the links on. Where people go on the link tree of a specific event, I would say, if you’re attending Verma or if you’re attending SDI wealth, click watch this video, and it’s a pre recorded video where I just explain about Bruce Lee, what we do, where you can book a call. I tried at an event. It cost maybe $100 say, to get all the stickers done, we would have calls booked on the back of it, because I could track it for a UTM code. When I had the success, I thought, well, what more can I do? And so I’ve done billboards. For example, when I was launching the second book, which was the book direct play blueprint, I discovered that there was a company that you could rent billboards in New York on Times Square. It was a bit of a cost, but I thought, this is, this is great to launch the book. And so I was able to get a billboard spot in Times Square, and I was able to get two of the co authors that I did the second book with who lived in New York to come down. We got pictures, and it flashed up for like a second, but we got the picture,

Alex Husner  25:56  
yeah, just a second, just for the picture. Looked at the OTAs

Mark Simpson  25:59  
don’t want you to know about which, yeah, didn’t generate sales for Bruce Lee, but the attention and the awareness of that post when we put it online just went through to her, yeah. And so

Alex Husner  26:12  
we’ve done some of the things that you just mentioned, but with a little bit when we went to Italy last year, we had a bunch of our stickers that we bring everywhere also. But actually, it’s funny that you mentioned it, because I just reordered these, and I put a QR code on them, because we’re out of the ones we have. But when we were in Italy, we put them on street poles, on buildings everywhere, and we’ve, we got, actually, an increase in people from Italy now listen to the

Annie Holcombe  26:40  
shows on a pole in Mexico City last year.

Alex Husner  26:42  
Yeah, all the straight balls, all the good places. I had never thought about the bathroom stalls, but I think that is super

Mark Simpson  26:49  
interesting to remember about the bathroom stalls for legal reasons. I do go and take those stickers down at the end of the day. I tell you what, though, when we were at Verma Orlando, I can’t remember the venue where it was, but their bathrooms people there were on it, and they, like, as soon, really,

Alex Husner  27:04  
straight down, keeps going in here,

Mark Simpson  27:07  
that’s this year. Like, like you saying, honey, I couldn’t make the STR wealth this, this year. And like you say, the the event is, is Marmite. So people love it, people hate it. But for me, from where my target audience is there’s like 2000 people in that room. That’s my target audience, everybody, yeah. And so I had two ideas this year, and I couldn’t be there because I was speaking event in in South Africa. So I organized for a mobile billboard. So I had the billboard in Nashville, which is great, but it’s right out on the interstate. Nobody sees it. So I thought, well, how can I get closer to the event? So I organized, I did a little search on Google, and I found this mobile billboard company that you could hire it for three days, cost about $1,000 and they were basically all day, just drive around the venue with the British National Anthem blaring out, and

Annie Holcombe  28:00  
the billboard

Mark Simpson  28:04  
was the old saying, like, the guy that the OTAs don’t want you know about with a QR code, with my face, and it’s like moving. And the amount of messages I got over those three days, I had Steve Schwab in a taxi sending me a picture, going, why are you on a billboard outside Nashville? Why not? I had Mike from happy guest with a video that you posted online and tag me in, and that was really cool. But at the same time I thought, Well, what else can I do? How can I actually get in the venue? This is why I had the idea of this wanted poster. And again, I quickly put it together on Canva. It looks shocking, but the best way to describe how I got the inspiration from this that there was a guy on YouTube called ampho, and he did this Timothy shall away look alike competition in New York round about February time it blew up and got a ton of exposure. And all that was, was a very simple look alike post a QR code, and it went everywhere. Well, I can do that. So I did it, sent it to FedEx. They print it, and it’s just waiting there to get picked up. I found somebody on TaskRabbit and basically paid for them for two days to take these. I think it was like 1000 posters, and would just hand them out. Obviously, you’ve got to be very careful with this, you know, if you you can’t do like soliciting, etc, within in the venue, but you can do it in public places around the venue. So I basically spoke to her, arranged for a few people that will remain nameless, to meet my task, grabber. Grab a load of posters that who were attending the venue, and they took the posters and walked into the venue, and again, they took pictures, and they left them lying around, etc. Again, this QR code on that had UTM tags on it, so I could tell how effective it was. And from a 200 I would say $400 that I spent on those posters we had, I think it’s just been clocked in about 12 to 60. $18,000 worth of revenue come back. So in terms of return of investment,

Annie Holcombe  30:04  
yeah, great. Roi

Mark Simpson  30:07  
social, social awareness was great. Again, it was a lot of exposure, shares, likes LinkedIn, DM saying, What are you doing now? And it’s just a ton of fun. Again, it’s just, it’s a bit of fun, little bit of, you know, being there, but not being there, and it’s got me thinking about what I can what I can do next. But what is really cool to see now is I’ve seen the likes of optimizer and auto rank. They are doing their own version of events and how they can sort of break the mold and get attention. And it’s really funny to see what they do at events with the Viagra rank. I don’t know if you’ve seen that.

Annie Holcombe  30:39  
And last year, the condoms,

Speaker 1  30:41  
the last year that was, I mean,

Alex Husner  30:42  
that’s right, yeah, what conference was that? I remember that earlier this year? That was

Mark Simpson  30:46  
Burma last year. Okay, yeah, again, yeah. It’s interesting, and it’s fun to see, because at the end of the day, when you go to a conference like before you even left, you can easily forget what’s being said on stage, right? People will always remember how you make them feel. And I like to do things with a little bit of fun, a little bit of joke, a little bit of just not gonna take myself too seriously. Well, that’s how I’ve run Bruce Lee. And, you know, the it’s worked, and I love doing it. I never take it too far. I don’t try and step over the line too much. I just try and have a bit of fun with it. And, you know, and Your vibe attracts your tribe, and the people that we work with are super cool, and the people that come to us are awesome, but at the end of the day, we just want to help them get get more bookings, get dark bookings, and we’re kind of a bit of fun while

Annie Holcombe  31:31  
we’re doing it. I can’t wait to see what you do for Verma this year. Talked about some ideas walking down the strip and get handed a picture of Mark.

Mark Simpson  31:43  
So I got in trouble last year at Verma, because remember Jeff and host GPO organized that pickleball. So I sent a boostly rep down. These were two of the top two pickleball players in the world.

Annie Holcombe  31:59  
Oh, my God.

Mark Simpson  32:02  
And they’re playing up against, you know, you know, the likes of

Alex Husner  32:05  
Robin Craig,

Mark Simpson  32:10  
oh my gosh. They won the competition, obviously. And they’ve got Bruce Lee shirts on, and they win it. And they social media was everywhere and spreading around.

Alex Husner  32:19  
They were just pickleball players. They weren’t related to the injury. Oh, my God, that is so kudos to you. I mean, like, this was super smart marketing.

Mark Simpson  32:29  
I’m not banned from taking part in any host GPO organized events.

Alex Husner  32:35  
We know Jeff, then we get you.

Annie Holcombe  32:38  
Oh, my goodness, I do. Like,

Mark Simpson  32:40  
it’s a lot of fun. So, yeah, I’m thinking about what the next one we can what we can do,

Alex Husner  32:44  
yeah, well, I think everybody you know from the vendor perspective is thinking about that at any of these events. Of like, how do we get, you know, more more opportunities to talk to people? There’s only so many opportunities to be on stage, and the vendor Hall is either super busy, which I definitely prefer that, or there it’s a ghost town. There’s no one in there. And it’s like, you pay all this money for booths and everything else, but you’ve gotta, you gotta get creative and think of different ways to just cut through the noise. And we talk about this on the show all the time. There’s a lot of noise. I mean, since last time we had you on the show, fascinating to know how many new suppliers have popped up since 2022 I mean, like it’s, it’s got to be hundreds, I would say at least, but yeah,

Mark Simpson  33:25  
especially the ones that have got aI at the end of the name. Oh gosh,

Alex Husner  33:31  
name, but it is AI.

Mark Simpson  33:34  
I was just with the boys at boom in South Africa for a lot of fun, so it’s great to see what boom I’ve done in the space and disrupt it. And, yeah, I’ve been, we have a lot of customers moving to boom at the moment. So it’s, we’ve had a lot of communications behind the scenes and figuring out API connections and integrations. But yeah, it’s, it’s good work. I was with the team when they signed up Rebecca cribben over in Oh God.

Alex Husner  34:00  
We were getting live pictures as that was happening.

Mark Simpson  34:04  
It’s awesome to see, and it’s great to see. And, yeah, there’s a lot of new people in the space, and it’s really interesting to I’ve been doing this now for, what, nearly 10 years, and I’ve been doing event space for maybe four or five of those years, and it’s cool to see. You know, I love going to events, catching up with people and saying hi to people, meeting people. And I’m doing the scale UK event in November, and they’ve given me permission to organize the icebreaker party the night before the event. Be prepared for the videos that are going to come out of that. I’ve got something. Oh boy,

Alex Husner  34:42  
we see you at the video camera. We’re probably gonna

Mark Simpson  34:45  
hide special lined up for that. It’s gonna be fun to see.

Annie Holcombe  34:49  
We won’t see you at scale Italia. Then,

Speaker 1  34:52  
No, I’m afraid. I’m afraid not. Because when is that again? Sorry, that is in

Alex Husner  34:56  
it’s a couple weeks early September right now.

Mark Simpson  35:00  
September is like, I am just not available in September. I have an idea.

Alex Husner  35:04  
Why don’t you come? It’s skill Italia, and then it’s the Women’s Conference, vacation rental Italian Women’s Conference. That could be your thing. You just show up at the Women’s Conference. Well, I mean, guys did it in Charleston. So that could be the big surprise. I’m here.

Speaker 1  35:17  
Hello, everybody.

Alex Husner  35:21  
I’m here to help. Oh, man. Well, I have actually have a serious question for you. So if somebody is looking at, you know, either building a website or redoing their website, I mean, there’s, I wouldn’t say, say quite a lot. I mean, I think there’s, like, a handful of vendors that are specific to vacation rentals that you can go to because they’ve got the API connections to the softwares, but, and I’ve worked with most of them at this point, some better experiences than others. But what’s the difference between Bruce Lee, would you say, compared to some of the more legacy website providers and like, what? What is the experience like for somebody when they come in to work with

Mark Simpson  35:58  
you? Yeah, I mean, I know all, all the guys that are doing website design that have got the connections and the connectivity, I think the connectivity is the key. Because anybody can put together a front end of a website. And, I mean, you can go on Fiverr, and you can find 100 people in India and Pakistan will do it for, like, less than, less than $100 now, but the connectivity is, really is the key, because the booking process from the point of where your future potential guest, that prospect, hits that map, hits that listing, and then wants to make the booking. That is so key. If you if you mess that up, the guest will just basically get fed up, get confused, and they’ll leave and they’ll just go straight back to Airbnb. So having that connectivity is is key. And I know that like Bruce Lee, we’ve got 27 connections and other guys at icnd, they do fantastic work, Gil at crafted stays, and you’ve got Eli Hudson and Conrad over at builder bookings. And we’ve all sort of, we’ve got this joint slack group between us, and we’re all we call ourselves the dark book and Avengers, and we’re just talking about the pain points and the pros and cons of what we’re doing and everything we share advice, I feel like what Bruce Lee separates from ourselves, from from others, and how we are a little bit different from others, is that we don’t just give you a website. We actually give you all of the tools as well behind the scenes that that you need to be able to succeed. So I talked about go high level. I talked about this. That’s a massive part, and I feel like we’re only scratching the surface of what we can do with that. So for email and social media, that’s bare basics of go high level. There’s so many other things that we can do, but we’re discovering with like AI and assistance and, you know, marketing flows and funnels, etc, so that gets plugged in, and that’s part of boostly. You don’t get charged anything extra for that. But we also do twice a week group coaching calls. So I do the Monday one. I’ve got Liam Caroline, who’s co hosted a podcast, who is a host himself, property manager himself. He’s got 20 to 30 properties in Norwich. He does the Thursday call. And we’ve got the community. So the community’s got about 10,000 years worth experiencing. You know, you come in and ask a question, you get answers from, like, really cool people who have been there, done that, bought, bought the t shirt. So it’s like the old package I always that’s why I say tools, tactics, training, confidence, to be able to go and practice being called short term rentals and growing your business. And everybody in there is from that, that two to 100 properties. That’s like, where our sort of world sort of sits. Yes, we get people with maybe one property or a couple of 100 of that. Two to 100 is sort of like where we sort of sit, and everybody in there is on that sort of path together, which is, which is really cool. And the thing that we’re doing next, which is the next thing that we’re going to launch, which is called Connect. I’m really fascinated at this, because it was sort of taking these API connections that I talk about that are really important, that I feel like as AI is going to grow. You can go onto any, probably, website builder, and get it to do a front end website for free very soon. But the thing that it can’t replicate is the thing behind the scenes, these API integrations that go into the pm are out there, and we’ve got 27 of them, and that’s growing every day, and that we’re going to take, we’re going to pull out, and we’re going to offer to people, and we’re going to call it connect. And what we can do with that, that’s really fascinating. So that’s, like the next sort of thing, I think

Alex Husner  39:11  
you, you told me about this, maybe even, like, a year or two ago. It was a while, but, I mean, basically it’s, like a universal API,

Mark Simpson  39:17  
yeah, that’s, that’s pretty much it. I’ve been talking about it for a year. It’s been taken a year to get to this stage. Oh, I’m sure. And what’s really cool is that I know Boris at flat away in Bulgaria, he’s creating his version of it. I know that Eli Hudson, he’s creating his version of it. So to see two industry peers creating something, knows that this is this is something that has legs. This is something for sure we can definitely, we can definitely achieve. And so yeah, that the goal from it would be that you can create a mini online travel agent, your own little mini listing site, within within minutes with this, and you’ll be able to do it all connected to this, to this dashboard. So that’s, that’s what we’re building now. And yeah, and the training will always be there. And I feel like, what. Truly like separates us is you get, you get a guy with a crazy British accent who does weird market instance, behind the scenes, access to my brain as well.

Annie Holcombe  40:10  
I think you keep people you keep people sharp, and you keep people thinking. And I think that that’s what’s really exciting. And I love watching what you do and how you interact with people because it’s, it’s, again, it’s, it’s constantly creative. It’s constantly retooling. It’s thinking outside the box, you know, the proverbial box all the time. And I think we need, we need more of that. There’s so many people that will say, a lot of people in this industry are sort of reticent to change, and I think they have upended that, and you’re making people see that, like you have to constantly be changing in order to adapt the industry is wanting you to be I just try and

Mark Simpson  40:44  
document it. I’ve tried to document it like a scrapbook since day one. And I talked about the good and the bad, you know, the good things and like, the like, the bad things that happened, the good things happen, and thankfully, now it’s all good. Last year was a little bit crazy, but, but, yeah, I try and sort of, like, I see what other people are doing in other industries, and package it up, and I sort of bring it into our industry. How can we do this in in here? And yeah, there’s some cool things that are going on, so I’m excited to see what the next sort of chapter looks like.

Alex Husner  41:11  
Yeah, I’ve got one question on that API, and then we’ll, we’ll wrap up. But is that going to be available for suppliers to access to, or is it for the purpose of if a vacation rental company wants to build their own OTA,

Mark Simpson  41:24  
yeah, no, I’m going to white label it. This is why I’m calling it connect and not boostly Connect, because then, with this we can. I would love to give it to like revenue managers or people who do Google ads, or we talk about Maddie mount. She’s got the content creator on me. I’d love to give dashboards to their content creators so they can then go and create their own little mini sites. So I’m looking to white label it for everybody, even website designers, even if you haven’t got property and you want to create like a listing site and go and market it, this is what this will be able to do, because you can, you can sync in more than one PMS into this dashboard at a time. So you could have free boom, customers sync their data, and you could have free whatever, customers sync their data and all into this one dashboard. So yeah, it’s really exciting. What we can do

Alex Husner  42:10  
that’s cool. That’s super exciting. I think that that’s probably one of the more interesting things I’ve heard about recently. So definitely keep us in the loop on that. But Mark, it’s always a pleasure having you. I can’t wait till the fourth time that you come back. If you come back four times, you will have hit a record. So we gotta make sure we get

Annie Holcombe  42:29  
that. But if

Alex Husner  42:31  
anybody wants to connect with you, obviously you’re going to be at scale UK, but any other conferences you’re you’ll be at

Mark Simpson  42:38  
fingers crossed, VR, nation, 2026 conversation, conversations have been had behind the scenes, so hopefully,

Alex Husner  42:47  
feeling I know where that’s going.

Mark Simpson  42:49  
So hopefully that one and I’m going to be back in Dubai next month for scale Dubai, which is a really cool conference, that what the guys are doing there is amazing. And I’m really excited to go back, because when we go to Dubai, the whole family comes with which I love. So have a bit of family time. Awesome.

Alex Husner  43:06  
Well, if anybody wants to get in touch with you, probably mark at Bruce lee.co.uk,

Annie Holcombe  43:11  
yeah, booster.co.uk.

Mark Simpson  43:13  
Is me, but Instagram, Instagram is my favorite channel. So Bruce Lee, UK or LinkedIn. Mark Simpson on LinkedIn.

Alex Husner  43:20  
Okay, great. Well, we will include links in the show notes for that, and if anybody wants to get in touch with Annie and I, you can go to Alex and Annie podcast.com and until next time, thanks everybody for tuning in.

Preserving People, Culture, and Legacy: Inside Nocturne’s Acquisition Strategy with CEO, Scott Wiseman

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In this episode, Alex & Annie welcome back Scott Wiseman, CEO of Nocturne Luxury Villas, for an inside look at how Nocturne approaches acquisitions in the luxury vacation rental space. 

Instead of treating acquisitions as one-size-fits-all deals, Scott explains how his team works with founders to create personalized exit plans that honor their legacy, protect employees, and keep guests at the heart of the business.

  • We discuss:
  • How Nocturne has grown to nearly 1,200 homes across six markets
  • Why culture and relationships are as important as financial outcomes
  • How Nocturne’s concierge services give vacation rentals an edge over resorts
  • What he sees ahead for the luxury travel sector
  • Honest advice for owners considering selling their business

Scott brings a grounded, people-first perspective to what’s often seen as a purely financial process. His approach reminds us that growth can happen without losing the heart of a company — its people, its culture, and the relationships that built it.

Connect with Scott Wiseman:
LinkedIn: https://www.linkedin.com/in/scottfwiseman/ 

Connect with Nocturne:
Website:https://www.nocturneluxuryvillas.com/ 


Transcript

Alex Husner  
Welcome to Alex & Annie: The Real Women of Vacation Rentals. I’m Alex, and I’m Annie, and we are joined today by Scott Wiseman, who is the CEO of Nocturne villas, and a second time repeat guest on the show. So good to see you, Scott.

Scott Wiseman  
Yeah, it’s great to be back. I miss I miss both of you.

Annie Holcombe  
No, we love talking with you. You’re always, you’re always, just like a breath of fresh air to talk to. And we were talking off camera. So there’s a definite difference in kind of the climates that we’re sitting in right now. You’ve got that you’re channeling your inner fall guy. And I’m still in the summer down in Florida, and Alex is right in between in Myrtle Beach. So we’re rolling into fall here.

Scott Wiseman  
Sounds about right? And it could change at any time for any one of us.

Alex Husner  
It could Exactly. Yeah,

Annie Holcombe  
absolutely. Well, why don’t you bring us up to speed on the world of Scott and what’s been going on for you?

Scott Wiseman  
Yeah, I’d love to, thankfully, it’s been really busy. Which is, which is great. We’ve seen the, you know, the slowdown, I think, in bookings that happened at the beginning of the year, with a little bit of uncertainty. And all of that was happening in the world has really started to heat up. And so particularly the last couple of months, booking pace has really taken off and getting back well into strong double digit year over year bookings for the back half of the year, which we’re really excited about. And kudos to our team that worked really hard to, you know, pull all the right levers, if you will, to kind of get us moving in that direction. And also, on the you know, acquisition front, we’ve had a lot of activity in the last couple of months, which we’re excited about. Met some amazing founders of great businesses over the last year for sure, and continued pretty heavily through this past summer as well. So there’s a lot of activity out there too, for people looking for that, that perfect next step for their for their businesses?

Alex Husner  
Yeah, definitely, a lot of people evaluating options right now. And you know, I mean, that’s really been going on for several years, really, but I think there’s just a lot of different ways that people can exit their companies now, and it’s becoming more of a reality for people that might have been thinking about it a few years ago, and they’re now they’re now seeing okay, this, this could make sense, but just to get our audience up to speed a little bit, in case they don’t know you, or if they didn’t listen to our last episode about a year ago, remind us how many markets Nocturne is in and how many properties that represents.

Scott Wiseman  
Yeah, we’ve since 2021 we’ve acquired seven different great local brands in six markets, and today we’re just about 1200 total

Alex Husner  
homes. Okay, yeah, and most of the portfolio is on the like luxury end. Is that correct?

Scott Wiseman  
Yeah, we do stay focused on the luxury side of the inventory, for sure, probably I can say that we’re somewhere between 25 and 50% of the luxury market in each of the markets where we’re operating. So we’ve got a strong presence in those in that space, in each of the local areas.

Annie Holcombe  
That’s impressive. I wanted to ask you, kind of you were, you know, talking about like people are assessing, and Alex alluded is assessing, like what they want to do with their business. And there seems to be a number of players in the market that are doing it in different ways to kind of help people either completely get out of it, or cash out some equity, or kind of buy into these various conglomerates of business. But there was one that came up as recently that I think, was the VR stakeholders, and I don’t, I still don’t understand a lot about it. We did have them on the show, and it’s a very interesting concept. But can you share a little bit of you know, what you know about the kind of that area and what maybe not turn offers differently for somebody that maybe does have a luxury portfolio and is thinking, Okay, what’s my next step?

Scott Wiseman  
Yeah, absolutely. I think, well, first, I think it’s good that, you know, high tide rises all boats. So we’re always very positive people’s success and experiences in the in the space, but they are very different. I mean, everyone kind of has a little bit different strategy. I know there’s is to kind of bring a big chunk of groups together and then kind of go to market all at once to bring some synergies. What we do is a little bit different in that we’re kind of staying really focused and committed towards the experience of going with companies that are looking for kind of that personalized exit strategy that really means a lot for them. It’s we don’t want to bunch anyone in to a larger group. We want them to feel that, you know what, their whether it’s their heritage being preserved, taking care of their employees, a transition. Many of them are so concerned, right, that they want to stick around for a year maybe or two, and help with the transition so that the homeowners are comfortable. But for us, it’s about a personalized exit strategy. So that means each person that we’re, you know, we’re working with to acquire we can cater to their needs, as opposed to kind of putting everybody into one bucket. Is really the big difference with us, and I think that’s. Been a great experience the last couple of months, specifically, of people feeling relieved and knowing that that’s even a possibility, and wait that can happen. And I can, you know, share, you know, the windfall with the team, but I can also do what I love to do, but not work 80 hours a week and still help the business be successful, or get involved in a little bit of earn out so they continue to get paid for the work that they put in. So that’s really been the secret to us, is that we’ve done it seven times. They’ve not all looked the same each seven times, but the success has always come out at the end, and everyone’s felt really happy with with where they’ve ended up.

Alex Husner  
Yeah, no, that’s great. And we all know some of the unsuccessful stories right of the industry over the past decade or so. And I think it’s just it’s more Top of Mind with companies as they’re assessing this because, you know, the people are the business in this industry for sure. And a lot of these people have been employees with these companies for some of them decades. You know, it’s a lifelong commitment that they’ve they’ve made to them, and they want to make sure that they’re taken care of, whether that’s staying in or, you know, being part of the exit. You know, some thoughtfully would fall thoughtfully done way. But I’m curious, when you’re looking at potential deals now, what’s the main thing that you’re looking at? I mean, I know you guys, you have mostly luxury properties, but is it the company size? Is it the brand? Is it just, you know, a good feeling from the owners that they be a good culture fit of what they’ve built like. How does that process work? Yes,

Scott Wiseman  
it is. It is really all of the above. I think first and foremost, it’s, you know, the quality of the homes, the reputation of the local brand, the ability to continue to grow within those those markets, the quality of the team that they have in place, and what they’ve been able to do over the years that all kind of plays into it. It’s not, it’s not a super complicated equation. You know, we don’t want to break anything we are looking for. You know, companies that have the bulk of the luxury share in that particular market. But we also don’t want to do anything that’s going to upset the apple car. We, I like to put it this way, we kind of take care of that nasty bits that they, you know, have looked for, not to be able to do going forward, like anything finance related or with it, helping with HR, driving more leads without worrying about, Do I need to know about SEO and PPC and anything that we can do to take away so that they’ve got more time with the homeowners and the employees and the guests, is really what we’re what we’re out to do. And so a lot of times we can really help that we’ve, you know, shown sustained growth with the local brands that we’ve bought, and there’s always a seamless transition during that same process and being able to kind of add the global scale that we have. So I’ve always learned something, even if it’s something that’s not in our wheelhouse, like maybe it isn’t enough luxury product to be able to, you know, sustain or what’s there. But I’m so appreciative anytime I get an opportunity to speak to someone, because I learn from them too. I mean, they’ve been so successful. And then often we’ll refer them to someone else who might be interested as well, for the type of business that they have too. So it’s always a good interaction, whether we move forward with them or not.

Annie Holcombe  
I wanted to ask you, from your day to day, when you’re assessing a business, how hands on are you? I know you’ve got a really strong team. We’ve met a fair amount of them, and all completely strong in all of their disciplines. And obviously you kind of the buck stops with you, so to speak. But how hands on do you get with these acquisitions and these conversations?

Scott Wiseman  
Yeah, very hands on. I think it’s important, not just from my side. I think they need to know, you know me as well, like, I don’t want to be like, you know, nameless, faceless CEO that they’re not quite sure. I think that the more they get to me, me and the team, the better, the better it is. And even when they are open to kind of sharing with their small group of leaders, if they have them, the sooner they let them know they’re interested, and we get to meet them as well. That’s a huge win, because it is still a cultural fit that does matter. I mean, it’s it doesn’t always have to be about money. It helps, but I think that a lot of them are looking for a connection to someone see what I’ve built, does someone respect it? And also, I find it’s helpful because they’ve probably never sold a business before, and it is scary if you don’t have an advisor or an investment bank, or even just the fact that you just don’t want to be taken advantage of, right? That’s what I hear a lot. Is someone said to me recently, actually, very recently, it was a great, a great question of, how do I know that you see something in my business that you’re not telling me so that you can take advantage of that benefit, and I’m not going to get it my sale price? Yeah. And I was like, well, quite honestly, we wouldn’t keep doing what we’re doing if anyone had a transaction with us and felt that they. Didn’t get what they wanted. We want raving fans, from people that have sold their business to us and got everything out of it that they wanted, from the, you know, their employees all the way through their financial satisfaction. And ironically enough, two weeks later, we went back and found something that was worth maybe a half a million in the business, and put it in front of in front of her, and said, We’re going to pay you on this because you missed it, but we found it, and we just just to prove what you said earlier, we’re not out to we’re not making money by cheating or paying you less for the business. We want to grow the business and keep the success going. And so it’s just a great opportunity to, coincidentally, the one person who asked it like that, we actually had something that we were able to come back and say, we’re going to give

Alex Husner  
you credit on this? Yeah, definitely. I’m sure it’s a lot of education from your side to these people too, if they haven’t, you know, gone to conferences and sat in on Jacoby and Jason sprinkles presentations on this. I mean, there’s just, and even if you have, there’s still so much to learn when it’s actually you behind the wheel going through it. But I’m curious. I mean, what is the main goal with Nocturne, or the opportunity that you see when you come into a company? Is it? And you’re probably gonna say both. But is it consolidation of resources so that they can operate more cost effectively? Is it growth or, like, where’s the opportunity that you guys see that you’re going to be able to make this a good investment, because, I mean, the companies are trading on pretty high multiples right now, so you’ve got to have some level of knowing where you’re trying to move the levers.

Scott Wiseman  
Yeah, I would say I put last on the list actually the savings or some type of cost structure changes, because you know, the businesses are usually not huge, and there’s very little redundancy, unless in one location, like, for example, we acquired two businesses in st BARTs years and years ago. And even that wasn’t an exercise in, you know, combining positions, because, again, no one’s retiring off of those savings. It is about growth. So I put two at the top of the list. It’s growth for the business. A lot of it has to do with using the marketing resources and tools that we have to drive the top line to get more leads. We have seen changes of 38 to 45% once moved on to our website platform and optimized in new leads and also conversions, just having better data to be able to make better decisions, to kind of grow the business. So that’s that that’s been good. But equally with that, though, is the talent within the company. So it kind of goes against the first point, which is, we’re not looking to cut we’re actually add a lot of staff, you know, usually to a lot of the businesses, to give them the resources that they maybe haven’t invested in. But more importantly, we have a huge percentage of current Nocturne employees today that came up from the local brands that we’ve acquired over the time. And that, to me, is great. I’d love to find talent when we can, you know, when we’re going to bring on a business where they can contribute. So we’ve got marketing, we’ve got finance, we have sales people that are all doing, you know, multiple brands, or at the nocturne level, that maybe would have even had a chance to do that, you know, staying with an individual, you know, local brands. So that, to me, those two things are the growth and then kind of taking advantage of great team members who wouldn’t have had an opportunity to do more is is probably the most exciting and the thing that we look for, yeah,

Annie Holcombe  
have you had any owners that have because, like you said, Some want to stay for a transition, but have you had any owners that have transitioned over to being an employee that because they were like, I love the business, I want to stay in it, but I just don’t want to own it anymore.

Scott Wiseman  
Yeah, we’ve got a great example, the first one with Christina cassis, who sold Telluride sold exceptional stays to us, is still part of the organization, being the first. And so she’s got the best of both worlds. She is unbelievably helpful to us. She was so connected. She built the business from scratch and just gave us a beautiful business that continues to flourish. And I, you know, find her to be an unbelievable resource to me and to the to the team. But again, it doesn’t necessarily mean that she’s working full time at this point, because she’s helped transition the business, but is available and at a beckons, call, beck and call. Sometimes she’ll travel with me to destinations to because she’s known people longer than I have in meetings when we’re looking at other places to acquire. So she’s been a great resource. So that’s the example on one end where, in a good way, she just won’t go away, and we love it, which is really good. And then we’ve had, you know, others that have exited shorter. But I’d say the average is that between, you know, one and two years somewhere in there is usually the average people will will stay on with the transition, which is usually fulfilling for them as well. Because. Not doing the day to day, you know, the rest that stuff’s all being handled, and they’re really focusing on what they loved in the business and why they got started in it in the beginning, which was taking care of the homeowners and those relationships, and have the freedom of just selling a business and be able to do that but still stick around enough to contribute and to continue to earn on that as well, with an earn out which so we’re not asking them to do that for free either. It gives them an opportunity if they believe in the upside still ahead then, and they stick around to help with that, it’s even better because they can make more over the initial price that they received.

Alex Husner  
Yeah, absolutely. And they’re there to answer your questions when many questions come up once you actually get, you know, totally behind the under the hood of understanding the business. So that’s a big part of it, too. But so, I mean, as far as some of the things that you guys have brought under one roof, I think when we spoke the last time, you talked about homeowner marketing, regular marketing, revenue management, is the tech stack all still whatever they’re on, or are you moving people onto the platforms that you prefer?

Scott Wiseman  
Yeah, we do move them to one tech stack. We think it’s vital in in in so many ways. One, it gives us a best practices, which is, you know, fantastic, because there’s always someone that’s figured out a better trigger and automation for customer contact. Oh, yeah, yeah. So, and all the bolt ons, right, the things that would concierge and for finances to be able to pull everything together, it makes life a lot easier. And we do all that heavy lifting. They do not have to worry about migrating anything from the old system into the to our system. We do it all behind the scenes. All they have to do is train on it, and we make sure they’re they’re ready, and sometimes it takes a while, we try not to disrupt like peak season and start from scratch. But the benefit far outweighs just leaving everyone on their own, individual PMS and other systems. It’s just too hard to help. It’s tough because people are used to one system, but we’re honest with them up front and said, Trust me, there will be benefits. I guarantee being able to do that. And it’s usually the general managers all talking to each other to solve a problem. You know. Now, if you’re a GM, you’ve got, you know, six, six different people you can ask doing the same job you’re doing in different markets, and say, how do you account for this? And how are you accounting for this? And when can you do that? And so it sets up a natural kind of communication between peers too, which is great.

Annie Holcombe  
So last time we talked, also, we talked about, kind of your expansion plans, and one of the things that you had mentioned that you had your site set on down the road was going into the European market. You have the some in the Caribbean, with the WIM CO and then you have Julie bird’s group in Cabo. And then you’ve got, I think you have, do you have do you have one in Canada? Or no, I can’t remember, not in Canada. Not yet, not yet. Yeah, so, I mean, is that still something that you’re thinking and I asked that just kind of like looking at where the market has been though, kind of the last year, I mean, Europe finally hit the peak that we did a year, you know, two years ago, and it started to slow down. So it’s like, you know, I imagine that there’s going to be some operators that are going to look towards next year and think, like, you know, maybe it’s time for me to start thinking, you know, in those terms. And actually, it’s funny, we’re going to be in Italy in a couple of weeks for some conferences. And I was thinking about, we were looking at places to stay, and just the amount of the variations from country to country, and what’s considered luxury, and what isn’t is pretty. It’s very stark, I think, in the terms of what we think as Americans, of what luxury is. But, you know, just maybe give us some, I don’t know, some bread crumbs, or maybe some, you know, magic eight ball of what’s going to happen for you guys down the road in that, in that realm?

Scott Wiseman  
Yeah. I mean, the good news is still within North America and the island, there’s still plenty for us to keep busy. So that’s good, but yes, down the down the road, and maybe sooner than later, probably since last time we talked, only because we’ve been able to realize that there are some that have a similar model to us, that are operating maybe a little bit smaller. Because to me, the biggest thing is the exclusivity part of it, and Europe, for the most part, is not necessarily an exclusive market when it comes to to villas. And in a past life, we used to do a high end Villa program, and you could have VIP checking in and in one day. And the you know, the owner of the villa decided his niece said she wanted to stay for the week, and so go do something else. Like it’s a very difficult thing to not have control those so doing it in the right way, which I think is there are some that have done that in Europe and have stayed committed to where they control the experience, and it doesn’t become too spread out, where it’s difficult to have consistency, and then you end up with a lot of potentially independent contractors that are taking care of disparate group of homes. We would do it in the same way that we’ve done with doctrine, which at concentration, where we control the experience and be able to do that. But I will say that there’s been, in a good way, in a positive way, some players. Out there that have been focusing in that way of building their business that could be really interesting for us.

Alex Husner  
Yeah, interesting as far as leveraging the brand to drive traffic or bookings to different locations, has that been a focus for Nocturne?

Scott Wiseman  
Yeah, absolutely. I think we’re still probably got room to go there, but to give credit to, you know, Erin, our CMO, and the work that she’s done on really assessing the customer profiles and database and really understanding who they are so we market to them better and more personalized has been really helpful. And there is a crossover between the brands, for sure, even though some are drive markets, some are fly markets, there’s a lot of room to improve. But yes, we have had a much stronger work done around the customer database to be able to customize communications, get them to stay more often, get them to experience others within the knock torn collection, too has been really helpful.

Annie Holcombe  
One thing that I it comes up in conversation a lot is that people will say that kind of the the luxury tier of travel, is kind of the last one that sort of gets impacted whenever there’s economic challenges and kind of when people get dicey about traveling. Have you guys seen any, any big impacts? I mean, I feel like I’ve talked to some people on 30 a that it’s kind of hit or miss. Some of them are just like they weren’t expecting it, so priced too high, waited too long. I mean, just kind of the the standard, if you’re not really watching, you know, watching things, but you know, have you guys seen anything? And like, what are you looking forward towards the future in terms of being able to isolate your groups, from maybe things that are happening, because I think that what people are saying is some of this stuff is going to, might take a lot, take longer, to kind of calm down, um, in terms of, like, international business and back and forth. I mean, what do you guys, I guess, what are you doing? Because that, you know, there’s, there’s so many schools of thought on it, but, I mean, you have a very specific model of business.

Scott Wiseman  
Yeah, we don’t take it for granted. I mean, everything you read says that, you know, the high net worth luxury traveler puts a higher priority on travel than they do other expenses and have more discretionary income to be able to do so. So we do see that as kind of a natural trend. But, you know, there’s all types of affluent, right? We have aspirational, affluent. We have high net worth, ultra high net worth. So well, you know, well over 50% is high net worth or above. That means we have 50% that are sitting, you know, probably in a fluent and they are going to be a little bit more impacted on on how that works. So we don’t ignore that at all. I think what we’ve been doing is leaning in on the things that we do really well, particularly when it comes to concierge services and the extra things that we can really build to make a perfect experience and competing much stronger against the resorts, because at this point, I feel really confident we could do everything you could do at a resort, and more except have strangers staring at you while you’re doing it. So yeah, I think that’s a that’s a good thing. So yes, we are working hard. It goes back to what I talked about on the database and understanding the needs and the booking patterns, reminding people of the experiences and where they stayed. You know, in in past years, maybe they skipped a year and going back and reminding them that now’s a good opportunity. But even in other industries, I’ve worked on the luxury side, what’s happening now? And I kind of brought it up in in the beginning, I do find that luxury, when it does slow, even with everything else it doesn’t slow, is bad, but it comes back faster, which is why the last couple of months, we’ve seen such a great ramp up, pretty much erasing that gap in the first, you know, part of the year that happened, when everyone was pausing, and so that that is definitely a strength of the luxury market, is when it comes back, it doesn’t trickle. It comes in full force. It’s like, switch goes off, and everyone’s like, Okay, I’m comfortable now, boom, we’re going to go ahead and spend so that’s that’s been nice. So we haven’t really, really had a plan to discount, you know, if anything, it’s a value add. And just reminding people why, why we’re here, we kind of take the philosophy that, you know, we still have owners that we have to take care of, and they have expectations, and they would prefer that we get them more money, even for less nights, so it’s less wear and tear than just keep it full for the sake of keeping it full. And they don’t panic, because we have a really good relationship with them, and they’re constantly getting information from us about how they’re doing. We tell them how the market’s doing. We’re honest if we’re under or above and what we can do to help them. So they look at us as good counsel and trust us, and so we take that pretty seriously, but it’s been a partnership with the owners, and also a shorter pattern of when things slowed up, which is great. I mean, the fact that it’s kind of roaring back before next year is a great sign, because it could have been all year. We could have waited at least a year to see when things might change from, you know, when things got a little glum there in February. Yeah. Yeah, people

Annie Holcombe  
will be glad to hear that. That’s

Alex Husner  
yeah, exactly. You’ve mentioned your concierge program a couple times now, maybe tell us a little bit about how that works and like, what’s similar or the same within Market to Market.

Scott Wiseman  
Yeah, it’s there different levels of concierge services or different amount of offerings, I think, just depending upon the destination and what people are into, I think it’s fair to say that we talked about Cabo a little bit earlier, that they kind of lead our company with the most amount of concierge services. Really creative team. I mean, they can do anything when it comes to providing services. And so, you know, they’re two out of three bookings. Are taking multiple concierge services with them, and then in other locations, we’re trying to be appropriate, right? Like using 38 as an example, beach bonfires, right? Become really important. Finally, pictures, celebration, events, milestone, you know, private chef experiences, so it’s a little bit different everywhere, but it’s something we’re doubling down on, and it’s not anything that we super mark up either, right? Our philosophy is it’s about the business, and that what we are as a brand. So I don’t really look to make a huge profit on the concierge services, because we want to be the company that people just know that we’re going to provide that. Because it’s about the home and the experiences. I don’t want to sit there and, you know, arbitrarily, you know, accelerate a profit on a private chef when I would rather them just know they can come to us, it’s going to be taken care of. Also, our partners that are working with us to do those things feel that they’re getting a fair shake as well. So that’s how we’re building it out. Is kind of coming from a real partnership level and making sure that it’s unique and special. And, you know, a lot of times just exclusive for us,

Annie Holcombe  
on the on the concierge. And actually, Julie had come into, Julie come from Cabo. She had come in with her, with George, her her partner, and they stayed here, I think, was last, last in the last summer, and she tried out some concierge services in the market. And we were talking about the differences and like, so her expectations, like you said, she’s kind of like the cream of the crop. She her team knows everything they do the best of the best. Her expectations are pretty high. And so how do you level, set that for your team? And then, like, maybe go in and provide feedback within a market to say how people can provide a better level of concierge service. Because I know just the Panhandle is very difficult to provide very high end services on a consistent level, from staffing and those type of things. And so I think that that’s where, from a brand perspective, it is very hard to be consistent. But do you find that you can go in and work with people within a market to help them level up that service?

Scott Wiseman  
Well, usually the best thing to do is that we bring people in on our own team to be able to do that. So we added on 30 a I guess you know services director that fully takes on and is familiar with the market and fully take on that relationship. So this is where I was saying before we like to invest and after we even, you know, buy a company, to be able to do the things they know. Every founder that I’ve met and sold the business they go. I just wish I had time to do all that in the past, haven’t really done it, so they know that the need is there for the most part. And we just try and make sure that we don’t overdo it, right? We don’t want to launch like 50 things when only like eight are really what mostly in demand and can be executed really well. So to your point, if we can’t do it well, we won’t do it. And we also try to be really careful. I’m not creating something that sounds really cool but isn’t really practical for what people you know want. So I think that’s a big, a big part of it is just understanding what the market is. Again, we don’t rush into that either, because it’s not anything that we want to disrupt. We want it to be accretive to the experience. So we take our time, we find the right people, and we build around a core group of services, and then expand from there again based on need. And if we’re listening to the guests and even the homeowners, know sometimes they’re like, I’d love for my home to be used with private chef experiences. What do I need to do? Should I up my pots and pans game and all fun stuff? But yeah, I think it’s just being aware what’s there and investing in your own people to help build it out and not just make it an independent contractor relationship, and hope that it works out for the best.

Alex Husner  
Yeah, yeah, we see a lot of companies that, as Annie mentioned, it’s like they either they want to do more on concierge or tours and activities, but they don’t really have time for it, and so there might be a little bit of effort that goes towards it at some point in the journey, but then the company isn’t set up to be, you know, handling that as as a as a big part of the business, I think that’s definitely a huge value add that you guys come in with, because that’s, it’s part of your brand promise, right? And I mean, you’re staffing your own people to make sure that the quality control is there. And, you know, even beyond just the revenue opportunity, even if it’s minimal. Mean, it’s guest retention that you’re you know, the experience could be vastly different if somebody booked at a home that did not have your team that’s setting all those things up, and they’re having to figure it out, or not figure it out, or have a bad experience because they didn’t, you know that the vendor properly. So it’s a big value add for you guys.

Scott Wiseman  
Yeah, and I think the guests also, if there are multiple destinations over a period of time, understand what’s happening within the local markets, that just because they had something you know, in one destination, it might not track or really be necessary in another, but all they care about is that there’s going to be a pre arrival concierge that’s talking to them about all the things that they can do and help you teach what’s important for them is really all they’re looking for is just that level of care and generosity when it comes to what they want to do while they’re there, I think matters more than the actual thing itself. So I mean, back to when you were saying, Annie, it’s really about how we deliver it that keeps it consistent and making it luxury and attentive, versus the specific service itself.

Annie Holcombe  
I wanted to ask you on that so I’m not sure. Do you guys use Airbnb at all for any of your properties? We do first for some of them. Yes, okay, so on that, the their their experiences, you know, obviously that kind of conflicts with the concierge services that you offer. How I’m assuming you probably opted out of having those at the properties, or maybe you didn’t, I don’t know. But how do you see that? Because that’s been a big talking point, a big bone of contention with a lot of people, and sort of the dynamics of it going into somebody’s property without the property manager and the property owner knowing that this is going on. Obviously, if they’re working with you, they know that this is a possibility, and you’ve already vetted the people, and there’s, you know, all the insurances in place and all the things that have been taken care of. But how do you see it with Airbnb trying to do that and be able and inserting experiences within properties?

Scott Wiseman  
I worked for a great British boss once who used the term, it’s chalk and cheese.

Annie Holcombe  
It’s chalk and cheese. What? Does that mean?

Scott Wiseman  
Yeah, I loved it. I didn’t have the accent. But to me, it for what we do. It’s, it’s not the same, yeah, and it’s not, you know, the experience and what we bring to it, I understand what they’re trying to do, which is what we’ve known all along, right? It’s about really being able to provide beyond just a house and beyond, you know, a villa or condo. It’s about the experience in wrapping people in as much or as little, you know, care and service that they want. So we think it’s, it’s very different than what we would bring to the table. I’m sure there’s clientele that would find that easy to do. But I think again, in the area that we play in, I think they feel a lot more comfortable speaking to us, the people that are actually putting it together, than dealing with an aggregator that’s putting together different experiences. So I mean, look, the there’s no reason they can’t be successful at it, I just don’t see it at the same level of attention to detail that we can provide.

Alex Husner  
Well, I mean, just, just the execution of it, but leading up to whenever the experience happens, and even when the vendor gets there to supply, if it’s a chef or, you know, photography, or whatever it is like. I mean, you guys know the properties. You know exactly when somebody should be there, what’s going to need to need to happen in order to get the home prepared for the service? And I mean, that doesn’t really happen necessarily when you’re using these outside vendors that they’ve never actually even been to the property or understand much about the stay. So definitely a different take on it. But I like how you guys are doing it better.

Scott Wiseman  
Well, the even the photographer, like our team, knows exactly when the perfect witching hour is, yeah, pictures, they’re like, they literally like, No, it has to be between this hour and this hour. Hurry up and get it done. And that’s when they need to do it. So just the fact that that that does make a difference in just even though it sounds like a little detail, but it literally is a picture, and so natural lighting kind of matters a bit.

Alex Husner  
Yeah, I’m interested, too. For the companies that you have acquired, were any of them doing their own concierge program before Nocturne came on?

Scott Wiseman  
Yeah, for for sure, some of them have had been doing it and that we’ve helped build out. Some have been doing it at a small level, some very basic but it’s all different, all different sizes and shapes.

Annie Holcombe  
I think, I think I know we, when we talked to Julie, we first met her, she was telling us, like, the elaborate things that they have done, I mean, talking about, like, you know, booking camel rides out in the desert and ATVs and fire walkers and all kinds of, all kinds of crazy things that I wouldn’t even think about going to Mexico. It just wasn’t stuff that entered my mind. But she had all these really great little kind of escapes from the, you know, the town to go see to go see things. I think that’s what she’s done there, is if they could replicate that everywhere. I mean, I think that would be, that would be impressive. But I did want to ask you kind of, you know, opening up. A crystal ball. What are you seeing in travel and hospitality, maybe specific to luxury that is going on right now? Or, like, what, what’s going to coming in the future? Like, do you see any big changes? Do you see any any things that are going to upend the industry, or maybe make people take notice, and specifically take notice of, like, vacation rentals? I think we’re in a spotlight. People have been noticing us for a couple us for a couple of years now. But do you think there’s any wholesale changes that are that are coming that maybe people need to be aware of?

Scott Wiseman  
It’s a great question. My crystal ball is really a magic eight ball, and it’s usually not very common to

Speaker 1  
me. I get a lot of Charles

Scott Wiseman  
it’s a good question. I do think what strengthened, though, the industry in itself, is that it really isn’t alternative accommodations anymore with what’s happened, right? I think that we’re kind of clearing that moniker in the space, and it’s it’s a real competitor to resort experiences, even those with Villa components within the resorts to be able to do that and put it forward. I see studies all the time that show that the demand for short term rental, particularly in the luxury side, actually can outstrip and is in some markets, the demand for resort and hotel, which I think is really exciting. So I think the big shift is, I think it’s going to be a more mainstream product. People are gonna have to pay more attention to it. It’s gonna be in the same conversations when you talk about what’s happening with demand, and you know, it’s usually what’s happening with the air lift into a place, or what’s happening then with on top of that, with the demand for hotels, short term rentals, are gonna be right there alongside kind of as a as its own industry, and standing tall. So I think that’s going to be good for us as as we go forward. I still think that people say that they realize it, but they really haven’t encountered fully what the short term rentals can do. At first, it was safety, security, you know, through the covid times. And to your point, what you mentioned about the concierge services, we’re finding more and more people. When they have a concierge service that takes them off the property and they’re into day four of their stay, that’s when they start to say, well, we want to change. We want to do something back at the house. We’re enjoying the house too much. We don’t want to leave. So we’re seeing that start to happen. So I think you’re going to see more of these services in home, in experience again, see real private because they realize they can do anything that they want in the homes. I think that’s going to continue to grow. So that’s why, you know the experiential side of it is it matters just as much as the home, for sure, going going forward and building, building all that, and having the flexibility and and doing all that. So I think that’s going to continue to strengthen in the next couple of years.

Alex Husner  
Yeah, that makes perfect sense, Scott, maybe to just kind of come back to where we started in the beginning as our wrap up. For anybody who’s listening and they are thinking about selling their business, like, what does that process look like when you start that conversation? And what should people kind of know going into that process?

Scott Wiseman  
Yeah, that’s it’s a great question. The first thing I always say is, what’s your dream like? What is your dream with this business? What did you hope for where where it is now? What would be the best possible scenario for you, and just listening and hearing whether it’s like, well, I originally thought maybe I’d leave it to my kids, but now I don’t want to do that. Or, you know, it is important for me that the, you know, employees I’ve had so long, or, you know, we would like to see them continue. We want to see the business prosper. It would, you know, break my heart if my name wasn’t, if the name of the business wasn’t still on there. I also would like to make sure I get X amount of money out of this, because I don’t want to work anymore, or I would like to invest in what Nocturne is doing. So I think it’s really understanding what they want first helps us understand what their motivation is. And kind of in the beginning, when I said, we’re been super flexible, because everyone has a different way they want to do it. I mean, it’s not like there’s 50 different ways, but everyone definitely has a different focus, a different way that they want to do it. What it looks like, what the transaction looks like, how much they want to take out of it, what happens with the team members? So that’s the first thing, is there. And then, of course, if they’ve got an advisor, an investment bank, it’ll help them with the valuation of what they think that they’re worth. Although I will say, I think the last two years, most people have spent the time trying to answer that question and preparing for a sale better so they’re more educated today than they have been in the past, because they made the time to figure out all the Add backs that they won’t run through the business that could count towards a stronger EBITDA and building the future bookings reports. So I do find that today, many of them are a lot more educated than were even a year ago or two years ago, because they put the time to try and figure it out and and see what’s what’s happening. It doesn’t have to be pain. Painful. There’s never any terrible conversations. Everything’s upfront. It’s, you know, again, it’s a good sharing experience, even if it’s someone that they’re not ready to sell. But we spend time together. I feel good that they at least understand more of the process and how things will be looked at and what recent valuations look like all of that stuff, very transparent, very open. You know, we want them to feel really comfortable in when they make the decision that they’re getting out of it what

Annie Holcombe  
they expected. That’s great. So if anybody wants to start a conversation with your team about potentially selling their business, or maybe looking down the road to sell their business, how can they get in touch with your

Scott Wiseman  
team? Yeah, they can. They can reach out to me, me directly, which is absolutely fine. I welcome it. And also, Anthony Barrera, on our team, is super helpful to reach out as well. He can provide initial information and some materials about Nocturne as well about what we’re doing. So either one of us, you can find us on the website, but we’d love to have a conversation. And again, I don’t mind if you even say I’m thinking about it, but haven’t done anything officially happy to you know, just have that conversation and set the table and give people something to think about.

Annie Holcombe  
Great. And we’ll see you at brma in Vegas, I assume. So if anybody’s wanting to tee up that conversation, they can grab you there. We’ll put the information on your con your contact information in the show notes, for sure.

Alex Husner  
Perfect. Thank you. Awesome. Yeah. Well, thank you for coming back again. Scott. There’s not too many people that we’ve had up back on as a repeat guest, but we were super excited to have you back on today with us. But if anybody wants to get in touch with Annie and I, you can go to Alex and Annie podcast.com and until next time, thanks for tuning in, everybody.

Koryn Okey Receives Crusader Award at 2025 Vacation Rental Women’s Summit

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Koryn Okey was honored with the Crusader Award during the 2025 Vacation Rental Women’s Summit, held August 21 at the Francis Marion Hotel in Charleston, South Carolina.

The Crusader Award is presented to individuals who challenge norms, lead with intention, and serve as catalysts for change within the vacation rental and hospitality sectors. Okey, Vice President of Client Experience at Breezeway, was selected for her dedication to elevating people and ideas across every level of the industry.

Over the past decade, Okey has become a widely respected leader in operations, service design, and customer success. Her work at Breezeway—a platform for property operations and guest experience—has not only helped shape how companies scale and support their teams, but has also centered on empowering professionals to reach their full potential. She has consistently used her platform to advocate for women in technology and leadership, helping create spaces where voices are heard and people are seen.

Okey is known for her integrity, approachability, and tireless commitment to improvement. Whether mentoring colleagues, leading workshops, or amplifying new voices on stage, she remains focused on impact—not credit. Her contributions reflect a quiet but powerful form of leadership that brings people together and moves the industry forward.

The Vacation Rental Women’s Summit, produced by VRM Intel, celebrates the contributions of women and allies in the short-term rental community and recognizes those who push boundaries, support others, and make space for progress.

Rachele Hobbs Receives Pioneer Award at 2025 Vacation Rental Women’s Summit

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Rachele Hobbs was recognized with the Pioneer Award during the 2025 Vacation Rental Women’s Summit, held August 21 at the Francis Marion Hotel in Charleston, South Carolina.

The Pioneer Award is presented to women whose leadership and innovation have created a lasting impact on the vacation rental industry. Hobbs, co-owner of Hobbs Realty in Holden Beach, North Carolina, was honored for her decades of service, her creative and operational leadership, and her enduring influence on the people and places she serves.

Hobbs formally joined the family-owned company in 1997, where she immediately began shaping both the guest and team experience. She launched Hobbs Realty’s first website in 1999, created the company’s iconic umbrella logo, and developed a series of memorable brand campaigns that became hallmarks in the industry. Her slogans—including “Once you’re booked, you’re hooked” and “Go the extra smile”—reflected a deep commitment to connection, service, and what she called “Hobbspitality.”

Though she had no formal training in marketing or operations, Hobbs took on nearly every role in the company over the years, from reservations to HR, housekeeping to accounting. She led the development of internal systems, including the company’s first employee handbook and HR department, oversaw the design of countless rental homes, and introduced hospitality features well ahead of industry standards—including stocked kitchens, keyless entry systems, and the area’s first guest loyalty program.

Her impact extended beyond the business itself. In 2023, Hobbs co-founded Hospitality Heroes, a nonprofit dedicated to supporting hospitality workers facing personal hardship. Her team describes her leadership style as one of “gracious professionalism,” a term reflective of her quiet strength and constant care for others.

Today, Hobbs Realty includes four generations of her family, with her grandson recently completing his first internship. Under her guidance, the company has grown into a widely respected name in the coastal vacation rental space.

Hobbs was honored at VRWS 2025 for her legacy of leadership, innovation, and compassion—a legacy that continues to shape the vacation rental industry from the inside out.

Michelle Marquis Receives Pioneer Award at 2025 Vacation Rental Women’s Summit

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Michelle Marquis was recognized with the Pioneer Award during the 2025 Vacation Rental Women’s Summit, held August 21 at the Francis Marion Hotel in Charleston, South Carolina.

The Pioneer Award is presented to women who have made foundational and lasting contributions to the vacation rental industry. Marquis was selected for her influence in advancing technology, building teams, supporting property managers, and mentoring professionals across the short-term rental sector.

Originally from Lahaina, Hawaii, Marquis entered the hospitality industry without a college degree, relying instead on persistence and a strong work ethic. After relocating to Oregon, she began her career in travel and hospitality at Mt. Bachelor Village and later spent nearly a decade with Navis, where she played a key role in the company’s growth and influence in the industry. Over time, she carved her own path, launching a personal brand and collaborating with a variety of technology and service companies.

In 2025, she joined Guesty as a strategic partner—marking the first time she would work directly alongside her daughter. During the awards presentation, a heartfelt letter written by her daughter was shared as a voiceover, describing her as inspiring, loyal, generous, intelligent, passionate, ambitious, and trustworthy. In the letter, she reflected on Marquis not only as a leader in the professional space, but as a mother who consistently encouraged others to believe in what’s possible. From pioneering sales operations before the discipline had a name to mentoring rising voices in the industry, Marquis was honored for her legacy of courage, innovation, and dedication to the people and companies she has served.

The Vacation Rental Women’s Summit, produced by VRM Intel, brings together leaders, founders, and professionals from across the vacation rental and hospitality landscape to share insights, celebrate contributions, and foster community.

Jodi Refosco Named 2025 Pioneer Award Recipient

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At the 2025 Vacation Rental Women’s Summit, held at the historic Francis Marion Hotel in Charleston, South Carolina, one of the Vacation Rental Pioneer Awards was presented to Jodi Refosco of Taylor-Made Deep Creek Vacations & Sales in McHenry, Maryland, for her invaluable contributions to the evolution and professionalization of the vacation rental industry.

As one of the earliest voices advocating for the legitimacy and long-term sustainability of vacation rentals, Jodi’s leadership and integrity have played a key role in shaping how property managers operate today. Through her work on national boards, state-level advocacy, and local tourism engagement, she has consistently championed both excellence in operations and unity in representation.

A West Virginia native with deep Appalachian roots, Jodi helped cofound Taylor-Made Vacations with her family in 2008. What started as a local property management company quickly grew into one of the region’s most trusted full-service vacation rental and real estate firms. Jodi’s commitment to quality, innovation, and staff development has earned her company recognition not only in the Deep Creek area but throughout the national industry.

Over the years, Jodi has served as president of the Vacation Rental Management Association (VRMA), contributed to advocacy initiatives at both the state and federal levels, and mentored countless professionals entering the field.