“Short-term rental is mainstream hospitality. It accounts for 14% of the global hospitality industry. And mainstream industries must operate by a different set of rules.” – Simon Lehmann
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
- AJL Atelier – Global STR Consulting helping professional hosts, property managers, and investors succeed in the short-term rental industry [https://www.ajlatelier.com/].
- Connect with Simon Lehmann on LinkedIn [https://www.linkedin.com/in/simon-lehmann-8375753b/]
Stay connected:
- Apple Podcasts: https://podcasts.apple.com/us/podcast/str-global-unlocked-with-simon-lehmann-unfiltered/id1842946960
- Spotify: https://open.spotify.com/show/3kke4wOx0tNv0duq9MMWtO
- YouTube: https://www.youtube.com/playlist?list=PLWVkmUOkmhSHcFjzi28AhaQNR98vaG65O
- Website: https://www.ajlatelier.com/podcasts
- Newsletter: https://str-global-unlocked.beehiiv.com/
Transcript
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.
