<aside> 🎥
Video coming soon — PC will record a Loom walking through this chapter. The notes below are what it will cover.
</aside>
By around November 2023, it became clear the company was burning through cash faster than made sense — some months, burning through more than its entire gross profit. A bridge investment (roughly $800,000, from the company's largest customer-investor, through an early version of what's now the $HOST-token program) bought time. But the real fix had to be structural.
For eight years, Hospitable's pricing had stayed close to its original joke of a formula: a base fee, loosely tied to the founder's rent, that had crept up over time from around $18–25/month to a $40 minimum but never been rebuilt from scratch. In 2024, that changed — a full pricing overhaul introduced tiered plans and brought legacy customers onto the new $40 minimum, with some previously-free features moving behind a paywall. The near-term effect was a jump in revenue, from the high $800,000s to just over $1 million a month.
2025 was explicitly a "catch up on the competition" year — Hospitable had fallen behind rivals like Guesty, HostAway, and Lodgify on features, and some customers were leaving as a result. The team shipped hard to close that gap, while also expanding beyond the core property-management product: a direct-booking and payments product, a new insurance line, marketplaces connecting cleaners and property managers with hosts, and the beginnings of a Vrbo integration.
A tariff-driven dip in April 2025 briefly slowed transactional revenue as US cardholders pulled back on discretionary spending, but the business recovered within a few months.
Hospitable remains founder-led: the substantial majority of the company is still owned by its founder and his family, with no private equity or venture capital investor ever having been involved. The company deliberately runs cash-flow-positive rather than accounting-profitable, reinvesting everything back into the business. Customers and team members can invest directly through the OATH token program — the closest thing to outside capital the company has ever taken on.
By the end of 2025, Hospitable was doing roughly $24 million in annualized revenue, representing somewhere between 10–15% of the entire US short-term rental supply — making it one of the largest and, by most measures, most innovative independent players in the space.