Hospitable’s Free PMS Plan Changed Everything for STR Hosts with Pierre-Camille Hamana, CEO and Founder of Hospitable
What would it look like if your property management software started working for you — not the other way around? In this episode of the Booked Solid Show, Gil sits down with Pierre-Camille Hamana, the founder and CEO of Hospitable, to unpack one of the most ambitious product months in short-term rental software history. Pierre breaks down a $0 subscription PMS plan, an MCP server that lets you talk to your own property data in plain English, a property manager marketplace, and a brand-new sister insurance company — all launched in April 2025. This isn’t a product announcement show. It’s a rare look inside the strategic mind of a founder who believes the STR software market is still wildly underserved — and is doing something about it. Summary and Highlights 👤 Meet Pierre-Camille Hamana Pierre-Camille Hamana is the founder and CEO of Hospitable, one of the most widely used property management platforms in the short-term rental industry. He started the company in 2016 after listing his spare bedroom in Brussels — a small bet that turned into a platform now processing over $5.2 billion in reservation income and sending more than 108 million guest messages annually. With a background in software engineering and business management, Pierre has spent nearly a decade transforming what it means to run a short-term rental — specifically for self-managers who want to operate like professionals without needing a full operations team behind them. His philosophy is simple: if the tools are good enough, hosts won’t burn out, and the industry grows. You can connect with Pierre directly on LinkedIn. 🚀 What Changed at Hospitable in 30 Days Pierre doesn’t do things incrementally. On April 1st, 2025, Hospitable announced four major launches simultaneously — and the timing was intentional. (More on that at the end.) The centerpiece is the new Essentials plan: a $0 subscription tier that gives hosts access to Hospitable’s core features — unified inbox, centralized calendar, guest messaging, and operations tools — with no property limit and no hidden percentage charged against bookings. As Pierre puts it, this plan is designed to be truly free, not a gateway drug to a paywall. Alongside it came an MCP server, making Hospitable the first PMS in the space that you can connect directly to AI assistants like ChatGPT or Claude. That means you can ask your property data questions in plain English. Their first internal build-a-thon with customers revealed what hosts started building almost immediately — and it’s the kind of thing that makes you rethink what “software” even means anymore. Then there’s the property manager marketplace, designed to introduce self-managing owners to vetted professional property managers — with performance metrics visible upfront. Think less cold outreach, more informed matchmaking. And finally, Align — a new sister company offering owners insurance designed specifically for the real risks STR hosts face, like guest liability and damage scenarios that standard feel-good policies often won’t actually cover. It’s a lot. But it’s also coherent, and the thread running through all of it is worth understanding. 🧠 The “Platform, Payments, People” Strategy Pierre shared something he described as almost an open secret — a strategic framework Hospitable has been executing since November 2023: platform, payments, people. The platform is the foundation — integrations, booking flow, centralized operations. That part isn’t new. What changed after ChatGPT’s release is the honest acknowledgment that software features alone are increasingly difficult to defend. If AI can help a host build their own automation, what’s the moat? For Pierre, the answer is payments. Specifically, being a merchant of record — not just a payment processor. This distinction is the most important thing in this episode that most hosts have never thought about. If a guest cancels a fully refundable reservation after paying $1,000, a standard payment processor (including Stripe-based PMS payment tools) charges you for a transaction that generated zero revenue. Hospitable charges nothing. On a chargeback for a non-refundable stay, the same protection applies. The liability shift is real. That payment infrastructure then unlocks the people layer: paying out property owners directly, paying cleaners through the platform, and now connecting hosts with property managers and insurance providers. As Pierre explained, once you’ve built the rails for compliant payment processing across every tax jurisdiction, you’re sitting on infrastructure that supports an entirely different category of product. This is why the direct booking site launched by Hospitable in 2020 initially struggled — not because of bad UX, but because hosts were blindsided by tax compliance, chargebacks, and the operational reality of being an entrepreneur taking online payments. The payment layer is what closes that gap. 💡 Why 65% of Hosts Still Don’t Use a PMS This is where Pierre gets candid — and a little urgent. Only 35% of STR listings in the US are connected to a property management software. That means 65% of the market is flying blind: no automation, no analytics, no multi-channel protection, no real foundation for building direct bookings. Pierre’s framing is stark: it’s been more than 12 years since STR software existed. That’s long enough for multiple unicorns to have emerged. Instead, the same segment of hosts keeps cycling between vendors, with no lasting loyalty and no category leader. He sees this as a systemic risk — not just a business problem. The Essentials plan is the response. Lower the commitment. Remove the price objection. Let hosts experience the tools before deciding whether to upgrade. If even a meaningful portion of that unconnected 65% starts using software, the compounding effects on host sustainability, direct booking adoption, and platform competitiveness could be significant. There’s also a strategic argument Pierre makes that’s worth sitting with: if 51% of the supply on any booking platform is connected to software, the dynamic between hosts and platforms shifts. Right now, hosts are captive. OTAs optimize for guests because hosts have no leverage. Software adoption changes that math — not by fighting the platforms, but by making supply mobile, informed, and portable. If you’ve










