Already in 2026, we’re seeing C-suite changes at several private equity (PE) funded companies in the short-term vacation rental industry. Among these enterprises is Casago Holdings where founder Steve Schwab reportedly will be transitioning out of the CEO role according to inside sources. Joseph Riley, who joined as president in September 2024, is expected to become the new CEO.
When Casago, a decentralized franchise company led by Steve Schwab and Joe Riley, completed its $130 million acquisition of Vacasa in the spring of 2025, the industry witnessed one of the most ambitious reverse takeovers in vacation rental history. The deal followed a period of financial distress for Vacasa, which saw its market valuation fall 97 percent from its SPAC-fueled $4.4 billion IPO in 2021. Strategic support and equity commitments for the transaction were provided by Roofstock, with Vacasa’s existing institutional investors Silver Lake, Riverwood Capital, and Level Equity rolling their stakes into the company and claiming seats on the board of directors.
Casago’s model relies on a decentralized franchise system where franchisees have demonstrated loyalty to Steve Schwab’s vision. This loyalty stems from his owner-centric philosophy and the “ORANGE” credo, which emphasizes local accountability and stewardship. Many franchisees joined because of Schwab’s leadership style, viewing the company as a “people-first” alternative to investor-driven growth stories.
Challenges Selling Vacasa’s Inventory
The goal of the acquisition was to convert Vacasa’s 35,000+ properties into Casago franchises. Execution has proven difficult. In some markets, Casago has sold inventory to the highest bidder, including operators who are not franchisees. Other markets that have not been sold remain under the Vacasa brand, using a skeletal crew of local employees and contractors to maintain operations as the industry moves toward its peak season.
Potential Culture Clash
The transition from a founder-led organization to one influenced by institutional investors has resulted in some friction among leadership, according to inside sources. The new board isn’t just a collection of property managers; it’s a roster of private equity powerhouses. With seats held by Silver Lake (Joerg Adams), Riverwood Capital (Jeff Parks), Level Equity, and Roofstock, the pressure to stabilize the combined entity’s bottom line is immense. This institutional influence often prioritizes standardized revenue growth over “cult of personality” leadership, which might explain the transition from Schwab’s RV-tour style of management to Riley’s operational oversight.
In addition, franchisees and homeowners are expressing frustration regarding new corporate fees introduced over the last 60 days. Internal sentiment indicates these charges resemble the centralized corporate model Schwab previously criticized. Loyalists who “signed up for Steve” are questioning their future with the brand as he moves into the background and institutional pressure for revenue increases.
Vacasa.com Branding and Ad Blitz
Casago Holdings recently initiated a seven-figure ad spend including TV commercials, to drive traffic specifically to Vacasa.com. This spend raises questions about the company’s long-term branding strategy. It remains unclear if this is a pivot to keep Vacasa as the consumer-facing brand or an attempt to transform Vacasa.com into an Airbnb-like OTA asset.
The leadership change and operational shifts mark a transition for Casago Holdings. As we wait to hear if Joe Riley is stepping into the CEO role, the company faces the challenge of managing legacy Vacasa assets and institutional board expectations while attempting to preserve the franchisee loyalty that fueled its original growth. The industry continues to monitor whether the “Owner-Centric” philosophy can survive this institutional phase.
VRM Intel reached out to Casago leadership for comment but has not yet heard back.
