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 been exploring how to reduce OTA dependency, this context matters. The tools exist. The barrier to entry is now $0.
🔒 What “Merchant of Record” Actually Means for Your Direct Bookings
This section deserves its own space, because it’s the part of the conversation most likely to change how you think about going direct.
When you take direct bookings, you’re not just running a calendar. You’re running a business with real exposure to chargebacks, tax remittance requirements, and fraudulent guest behavior. Pierre laid this out with a clear scenario: if a guest stays, then files a chargeback after checkout claiming the stay was unsatisfactory, a typical payment processor leaves you holding the bag. You lose the booking revenue, the processing fee, and pay a chargeback penalty on top.
As a merchant of record, Hospitable absorbs that liability. Tax filings across multiple jurisdictions are their problem. Identity verification — the kind that actually flags criminal networks, not just checks a box — is their cost. That coverage is priced into the take rate for direct transactions, but when you compare it to what you’d pay sourcing each of those services independently, the math typically favors the platform rate significantly.
This is directly relevant to anyone building out a direct booking funnel and wondering what’s missing. For most hosts, the missing piece isn’t traffic or a beautiful website. It’s the backend trust infrastructure that makes a guest feel safe paying you directly — and makes you protected when something goes wrong.
🤖 AI in Your PMS: What the MCP Server Actually Enables
The MCP server launch is the part of this episode that’s hardest to fully appreciate without seeing it in action. But Pierre’s description of the build-a-thon — where Hospitable customers built their own tools and workflows on top of the PMS using natural language — gives a glimpse of where this is heading.
The idea is straightforward: instead of navigating menus to pull a report or trigger an action, you ask in English. “Show me my revenue by property last month.” “What’s my average ADR for bookings that came through direct versus Airbnb?” “Send a message to all guests checking in this weekend.” The PMS executes.
What makes this different from a chatbot is that it’s connected to live, actual data — your data. Gil drew a direct parallel to how AI search is changing STR visibility, and Pierre echoed it from the operations side: hosts who embrace AI tools now will have compounding advantages over those who wait.
This also reinforces something Pierre said quietly but clearly: the software companies that stay closest to their customers — with tight feedback loops and fast release cycles — are the ones that will survive the AI disruption. The ones building in silos are already losing ground.
🏘️ The Village: Revenue Managers, Cleaners, and What’s Next
Pierre revealed — only half-jokingly — that the internal codename for the marketplace is “The Village.” It takes a village to run a short-term rental, and Hospitable is building one.
Cleaners are already connectable through a supplier partner. Property managers are now matchable through the marketplace. Insurance is live through Align. Revenue managers are next on the list — and Pierre made a specific point worth noting: most revenue management services are currently priced and structured for large operators. There’s a real gap for self-managers who want professional pricing strategy without the enterprise price tag. Hospitable is looking at how to close it.
Marketing and brand support is also on the roadmap, which is where Gil added something relevant from his own experience: the gap between hosts who have a brand-forward direct booking presence and those who don’t is enormous, and growing. Professional STR brand identity isn’t a luxury for large portfolios. It’s the thing that makes your direct channel actually convert.
⚡ Rapid-Fire Highlights
📚 What book has inspired you? Ender’s Game by Orson Scott Card. A science fiction staple that Pierre says influenced him more than he probably should admit — especially in difficult moments when he needs a reference point for thinking through complex, high-stakes decisions.
🧠 One piece of mindset advice for someone starting something new? “Congrats for trying. Congrats for starting.” Set a milestone three months out — something visible enough to measure traction. But here’s the contradiction Pierre lives by: he never hit a single one of his early milestones. Not one. And he still pushed through, because something was still moving. Set the end date. Then ignore it if the signal is still there.
🚀 One tactical move for someone starting or amplifying direct bookings? Photograph your property with a branded pillow or embroidered cushion with your company logo or website visible in the shot. On OTAs, they can’t hide it. Guests curious enough will search for you. It’s a simple, low-cost redirect that moves traffic from their platform to yours — and it starts in the photo shoot, not the marketing budget. And once you go direct, remember: you’re an entrepreneur now. Taxes, payments, compliance — you don’t have to do it alone. That’s exactly what the right infrastructure is for.
🔗 Connect with Pierre-Camille Hamana
🌐 Hospitable.com 💼 LinkedIn: @pchamana
🏡 Ready to Turn Your Traffic Into Direct Bookings?
If this episode sparked something, the next step is making sure your direct booking website is actually built to convert. Driving traffic to a site that isn’t optimized is the most common gap between hosts who grow their direct channel and hosts who stay stuck.
CraftedStays is purpose-built for short-term rental operators — fast to launch, connected to your PMS, mobile-first, and designed to turn visitors into guests. Whether you’re just starting out or ready to build a brand that compounds over time, the platform is built for exactly this moment in the industry.
👉 Start your free trial at CraftedStays.co
Transcription
Gil: Before we bring on our guest, I want to talk just a little bit about something that I’ve been hearing a lot from hosts. I keep on hearing the same thing: “I know my website isn’t converting, but I can’t afford $8,000 on an agency to rebuild it.”
Here’s the thing — you’re learning all these marketing strategies, you’re driving traffic, and you’re putting it all to work. But if your site isn’t really built to convert, you’re basically lighting your energy and money on fire. And even if you could afford an agency build, every time you want to test something or make a change, you’re having to pay them again. You can’t iterate, you can’t test, and you really can’t improve on things.
You don’t need a custom $10,000 website to get the conversion rates that really matter. You just need the right platform. That’s why I built CraftedStays. It’s purpose-built for short-term rentals and designed from the ground up to help you drive more direct bookings. You can finally turn that traffic into bookings, and you can keep on testing and improving as you learn. You can make changes all on the platform — you don’t need to learn something new.
So if you need some help or you want to get started, go ahead and go to craftedstays.co and start your free trial. Now let’s bring on our guest.
Hey folks, welcome back to the Booked Solid Show — the show where we bring in top operators to discuss hospitality, operations, and direct bookings. On today’s show, I have Pierre, the founder and CEO of Hospitable. He shares what’s changed in just the last 30 days within Hospitable, and it’s a lot. We also get to dive deep into his product thinking, how he’s shaping the company, and why he invests into the things that he’s been building with the team. It’s a fabulous show, and without further ado, let’s bring him in.
Hey, Pierre. Welcome to the show.
Pierre: Hey, Gil. Thank you so much for having me. It’s a pleasure to talk to you again.
Gil: Yeah, it’s been many, many months. I think it was probably eight months since we last talked.
Pierre: Probably something like that.
Gil: I remember — as a founder — you gave me some pretty pointed advice on how I should take care of myself and how I should take care of the team. So I appreciate you being very candid on that last call with me.
Pierre: Yeah. When you don’t have a co-founder, when you don’t have an investor, when you don’t have a board to tell you those kinds of things, it feels good to hear. I wish someone would have told that to me a long time ago. But I’m very happy with the impact that it had on you and your company, because you keep growing and it’s absolutely amazing to see from the outside.
Gil: Yeah. And I equally watch what Hospitable is doing — all the PMSs and what’s happening in the industry — and I’ve seen a lot of changes happening inside Hospitable. So I actually want to spend a good chunk of our talk today really discussing what the impetus of all this is, the philosophy behind some of these changes, and maybe dive deeper into what those changes are.
Over the last six months, you’ve introduced a few things. I think there’s one pretty big thing in the industry that we haven’t seen before — this whole freemium model. We’ve never heard of a PMS give things away for free. That’s very counter to what I see from PMSs more generically. What’s the thinking behind that?
Pierre: It’s definitely not in the culture of being a property management software company. And to just say it plainly — it’s not even across many months. It’s actually just this month. On the 1st of April, we released our new Essentials plan. That is indeed a no-subscription-fee plan that allows you to leverage all the integrations we have — unified inbox, centralized calendar, guest messaging, operations — everything we believe is really core to running and scaling a short-term rental.
There are some restrictions, but it’s basically at $0. No limit on the number of properties you can connect. No back-charged percentage of bookings generated through booking platforms. So it’s truly free. If you want to make it zero, you absolutely can.
That same day, we also released an MCP server — which means we are the first property management software in the space that you can connect to your AI assistant, your agent, your ChatGPT, your Claude account. That allows you to talk in English to the APIs of your property management software. We just finished a build-a-thon with our customers on what they’ve been building in that first month, and what’s happening is crazy. The era that we’re in is very, very exciting.
Two weeks ago, we released our property manager marketplace. We realized that many of our self-managing customers are leaving Hospitable to work with a property manager — and we wanted to accelerate that transition. But we’re also seeing plenty of users creating an account who are actually looking for a property manager themselves. So we’ve started providing deal flow — introducing owners who are looking for a property manager with a property manager in their area, where they can submit bids and see what happens.
And just yesterday, we announced our sister company, Align — an insurance company, a one-stop shop for asset protection. It allows you as an owner or property manager to find the best insurance for your business and your property. We’re talking about owner’s insurance — not damage protection or Airbnb-type coverage — but the actual policy you need as an owner. We hear so many stories of people paying feel-good policies that won’t actually cover them when something goes wrong — like a guest’s dog escaping a fence and biting a neighbor. That’s your liability. We want to make sure there’s appropriate coverage for that.
So — a free plan, an MCP server, a new AI layer, a new property manager marketplace, and a new insurance company. That was just this month. We’re cooking.
Gil: That’s a lot. I come from a product management background, and I always think about product strategy and the philosophy behind product development. The thread I keep picking up on is a sense of empowerment — almost embedded into all the features you’re building. The MCP server empowering folks to do their own analytics. The Essentials plan allowing hosts who are just starting out to have professional tools they would have felt they needed to grow to a certain volume to unlock. Is empowerment the core philosophy here? From the inside, do you see it the same way?
Pierre: I think this is great. I wish I would have come up with that framing. It’s not exactly how we talk about it internally, but I think it’s right. My own goal is basically: we need to expand the market. The market of software for short-term rentals is ridiculously small. It’s probably hundreds of thousands of customers — maybe at maximum — that are switching between different vendors almost every year, without any sense of loyalty because no solution is ever really compelling.
Every other industry in the world right now is seeing massive opportunity because of AI development. And you cannot risk an industry being completely sidetracked from this. For me, it’s almost a survival, systemic problem. What percentage of revenue is being invested into AI within short-term rentals? It barely registers.
Here’s the number that puts it in perspective: 35% of listings in the US — probably the market with the highest willingness to pay in the world — are connected to a property management software. That means 64% have nothing at all. And so much stems from that fact alone. Hosts burn out because they’re not pricing their own time. They can’t look at another channel for marketing because it feels too complex. It’s almost seen as a sign of a very mature operation.
If I ran a business and we were putting all our marketing dollars on one channel, I would call that absurd. I would call that concentrated risk. In short-term rentals it’s like, “I just want to be on that one platform.” This is amazing for the platform — but you don’t get a right to complain about those booking platforms always serving the guest, because the hosts are captive. Only the guest is the variable they’re optimizing for.
What I want to do is basically this: if we get to grow the market of software adoption, lower the level of commitment and effort required, we can perform what I would call a 51% attack. If the supply of any booking platform is 51% connected to software, what happens? They compete. All of a sudden hosts are no longer captive. It becomes about which platform books the most at the most friendly host terms. There is a lot that’s a consequence of this lack of software adoption. And if we don’t take action now, I don’t know what the world is going to look like in two years — but it’s going to be a lot more concentration and hegemonic power over entire industries.
Gil: So from your perspective, there’s this acknowledgment that there’s a very small concentration of hosts with professional tools. 65% are not connected to a PMS, meaning they’re highly dependent and will always be dependent on a single channel. And there’s also a lack of tools that allow them to effectively become independent. It sounds like Hospitable is also creating a bridge — so that if they do find themselves at capacity or don’t want to manage themselves, there’s a pathway within the ecosystem for others to help them. That’s the thread I’m seeing.
Pierre: Yes. And it’s really about being captive from booking platform tools and features. Property management software delivers a lot of features so that you have to do fewer and fewer things yourself. With AI in particular, we’re seeing such acceleration in what software can actually do for you — and the MCP is a great example of that.
The strategy at Hospitable — and I’ll tell you this, it’s probably been said on a few podcasts but nobody pays attention — is platform, payments, people. That’s the strategy we’ve been executing since November 2023, which is exactly when ChatGPT was released. We were on a retreat and said, “Okay, we need to project ourselves into the future. What actually stays after, in a world where this technology evolves?”
A property management software is a platform. It’s only as good as the quality of its integrations. But now we’re in a situation where there is less and less defensibility around those features. It’s a tremendous amount of work, and two years from now, some of it may be worth nothing. That’s just the reality. And so the booking platform integrations — Airbnb, Vrbo, Booking.com — are not open APIs. They’re extremely expensive, take months, and require certification. That’s still a real moat. But beyond that, we have payments.
Gil: Shopify is probably the one that comes to mind for me.
Pierre: Exactly. You start as a platform — your integrator is Stripe — and then eventually you’re intervening in the flow of funds. That’s only as good as the extra services you can offer. Being the merchant of record, facilitating transactions, handling chargebacks, tax compliance. That takes enormous work across every jurisdiction.
Last year we released owner payouts — property managers can now distribute funds directly to owner bank accounts from within Hospitable. We can pay your team, pay your cleaners on a schedule. Many of those features we don’t charge for. You get one payment per month for free.
And then the last part is people. It takes a village to run a short-term rental. If you don’t know a cleaner, we’ll connect you with one. The property manager marketplace means you can have a turnkey service with an experienced professional. Align means you’re covered on the insurance side. The platform is the foundation — without it, you can’t do the other two.
Gil: I like the framework. Right now in the SaaS industry broadly, there’s a real threat of “do I still need the software if I can build it myself?” There are some places where there is defensibility, but SaaS in general is in a very chaotic place. Anthropic is disrupting companies that felt like they had a strong corner of the market.
One of the things you ended with is something I see consistently in how you treat your customers — that mentality of: how do you continue to add value? And I think that’s why you do the town hall every other Wednesday. You’re constantly close to your customers, and that feedback loop is extremely tight. The ones that are closest to customers can react and evolve. The ones building in silos have a really hard time.
Pierre: That’s true. And it helps that about 25% of the company at Hospitable are hosts and property managers themselves. They’ve mostly been concentrated in sales, success, and support roles — where they influence product but don’t build it. Now you put Claude and Cursor into every single one of their hands, and they become coders. And there is a very big difference between coding for someone else and coding for your own problem. You pay a ton more attention to detail. You’re obsessive. That’s where differentiation actually happens.
And in terms of the feedback loop — I want to be clear about accountability at Hospitable. I am not the highest authority. If I want to spend an afternoon at the park with my daughter, don’t bother me with anything. My opinion doesn’t matter. Go meet the market. Go meet the customers. I can assure you they’re pretty clear at articulating their emotions.
Every time we’ve failed at product, it’s because we waited for internal validation before getting something out. Every time we pushed and asked “is this good for us, is this solving a real problem — let’s ship it and get more feedback,” that’s worked far better. This seems obvious, but in a tech company there’s always someone who doesn’t want the risk. There’s always an engineer working on the 35th level of complexity of a scenario that’s never going to happen. And then you release it and the button doesn’t work. It’s a law of the universe.
Gil: I’ve led product teams many times. Product managers get to a point where they prefer to work with design teams on new features rather than spending time on customer calls. If a product manager isn’t spending at least a third of their time with customers, there’s a cultural problem. That leads to building in silos and building for ideation rather than feedback.
Pierre: Who is running product at CraftedStays? That’s still you?
Gil: That’s me right now. Yes.
Pierre: Of course you are. I still lead standups too. And think about it when you grow and delegate that to another product person. That’s something we navigated at Hospitable — and what we still do is keep the product team accessible. If you’re on Hospitable, go to Help, then Give Feedback — you can schedule an office hour call with Andrew, our Director of Product, Sam, our Director of Engineering, and every product manager on the team. That’s truly how to book time with our top product team.
Gil: At one point it became unsustainable for me — I was taking every single onboarding call, and if you wanted to book, you couldn’t get me for three weeks. That’s not a good experience. So I had to eventually delegate and figure out which customers I personally needed to be on and which ones could go to someone on my team. As we grow, that will continue to evolve.
Pierre: The culture is really the immune system to protect from those things.
Gil: What’s the goal for customers on the Essentials plan? Do you want them to eventually graduate to a paid plan, or are you perfectly fine if they stay on Essentials?
Pierre: Both. The message right now needs to be clear — there is no excuse on price, on scale, on what you’re looking for, to not use property management software. You can have it all at zero dollars, unlimited properties, same features as every paying customer.
I’m totally fine with them staying on Essentials for a long time. Because if our strategy is platform, payments, people — the platform is only as valuable as it supports the payments and people use cases. For direct bookings on the Essentials plan, we still offer full payment processing, tax compliance, and chargeback protection — but the take rate is ten percent instead of seven. If you’re successful at direct bookings, over time you’ll naturally want to save money by moving to a recurring plan. Same logic for paying cleaners.
There are some messaging restrictions on Essentials — for example, you can’t send messages before a reservation is confirmed without including a link to the guest portal. But that guest portal is where your upsells live. So that’s actually a compelling reason to use Essentials: you’re not paying money out of pocket, but without a PMS you’re leaving money on the table — no way to collect for early check-in, late checkout, or other upsells. No way to do guest verification or rental agreements.
We also sell trip insurance on those guest portals, and we pay the host back whenever a trip insurance policy is purchased. So this is genuinely a less-than-free service, not just a free one.
The marketing equation also matters: most of the cost of a customer has been incurred before they sign up. It’s three orders of magnitude cheaper to retain a customer — even for free — rather than forcing a paywall and potentially losing them while we can still generate ancillary revenue together.
Gil: Yeah. And I think it’s important for our listeners to understand the reasoning. A lot of times when you see “free,” you don’t know where the catches are. Is it sustainable? Are they going to switch it on me in two years? Understanding the business logic behind it — and the paths that exist for hosts to grow within your ecosystem — that’s what builds real trust.
One other thing I want to unpack: the investments Hospitable has made on the direct booking side. A few PMSs also have a payments play, but yours is very different. Others take a cut off payments. You’ve added tax remittance, damage protection, identity verification — you’re thinking about protecting your customers’ assets almost as much as your own. What made you go down this path?
Pierre: I’m slightly offended by the comparison. Here’s the test I’d give anyone: you have a guest who pays $1,000. Two days later, they cancel. You have a fully refundable policy to boost conversions. You refund them $1,000. How much have you lost?
Gil: Three percent.
Pierre: With Stripe, you lost three percent — the transaction cost on a booking that generated zero revenue. With a PMS-provided payment solution, you lost four percent. On Hospitable, you lost nothing. It was a cancellation. You were never meant to lose money on a cancellation.
Now do that again — but this time you have a non-refundable policy and the guest files a chargeback. With Stripe, you lose the $1,000, the processing fee, and a chargeback penalty. With a PMS payment processing solution, similar result. On Hospitable — that’s our problem. We cancel the reservation and handle it. That’s why we charge seven percent. We’re not just doing payment processing. We are the merchant of record. Your guest is transacting with us, and that allows us to take the maximum responsibility for securing those transactions.
We’re also liable for taxes across every jurisdiction. We calculate the right amount, remit them on time, handle any discrepancies. If there’s an audit, that’s us on the hook. We offer an experience where you get all the benefits of the asset with none of the liability. You’re the king in your own castle — but with none of the exposure if anything goes wrong.
We learned this the hard way when we launched our direct booking website in 2020. Customers weren’t adopting it because they kept running into chargebacks and tax compliance on their own. That’s when we realized there was a massive gap between “I’m a host on one booking platform” and “I’m an entrepreneur taking direct payments and navigating everything that comes with it.” That realization shaped our entire product philosophy.
At scale, our buyer power also matters. Identity verification and damage protection insurance — those are negotiated across tens of thousands of properties. The pricing we can offer is meaningfully different from what any individual host could access on their own, often by orders of magnitude. And we never get credit for the crimes we prevented — the fraudulent guests we flagged, the criminal networks we blocked. But those protections are real, and they’re working every day.
Gil: I’ve been genuinely impressed with the suite of tools Hospitable has built. I work with many PMSs, and I see some that serve hundreds of property managers without close to the same capabilities. You’re left with hosts stitching things together through marketplaces and losing the economies of scale that come from having it under one roof.
Pierre: Just counting the identity verification and damage protection — the advantage we have based on volume is very meaningful. When you negotiate for 30,000 to 50,000 properties, those are not the same terms as any individual host would get. Which means if you source those things independently, you often end up going for the cheapest option — which is almost always the one with the lowest friction and the worst protection.
Gil: You mentioned the third pillar — people. Cleaners are one use case. What other people services are you looking to connect in the future?
Pierre: I want to address the obvious concern first: every property manager listening is probably thinking, “Hospitable is going after my cleaners.” No. This is what we call the Chinese wall. You can pay your own cleaners. You’re responsible for sourcing them. Cleanster is a supplier partner we’ve connected with to give you an option if your cleaners aren’t available — useful when life happens.
The property manager marketplace is a really meaningful use case. Owners don’t know what a property manager’s services are, what their rates look like, what their performance metrics say. On the property manager side, they have no scalable way to identify owners who are ready to hand off management. This is closer to matchmaking than a directory. It’s facilitated by the number of Hospitable users on both sides.
One I’m particularly excited about is revenue managers. Right now, professional revenue management is priced and structured for enterprise operators. There’s almost no model that works for self-managers or small portfolio operators. If there’s a way to innovate on business models and make revenue management accessible at that scale — first just by making it easier to find a good one, then by figuring out the economics — that would be genuinely valuable.
And yes — marketing is on the list. It takes a village to run a short-term rental. The internal codename for the marketplace is The Village.
Gil: I’m starting to see why some of these pillars are such a big part of your strategy now that we’ve unpacked it.
Pierre: Yeah. But Gil — I’m just telling you. It’s in confidence.
Gil: Just the two of us. I’m not too worried. You folks move fast, and there’s a lot more red tape on other PMSs even if they know the strategy. That’s one of Hospitable’s defensible moats.
Pierre: Not worried at all.
Gil: Pierre, we usually end the show with three questions. First — what’s been a book that has inspired you?
Pierre: Ender’s Game. There are many non-fiction books that have been absolutely fantastic, and none of them come to mind because I’m terrible at names. But Ender’s Game is the one I come back to. Science fiction. I’ve been told it probably influenced me a little too much. But in a difficult moment or situation, that’s the one I return to.
Gil: Second question — what’s one piece of mindset advice you’d give to someone starting something completely new?
Pierre: Congrats for trying. Congrats for starting. Put a milestone three months away. Sometimes that’s big enough to see traction and give you optionality. But you will regret it if you don’t try one more time.
What I mean by that — I’ve seen many founders who have been at it for a decade and have never shipped anything. And I’ve seen probably many more who tried, gave up, probably a bit too early. It’s very difficult to be in that spot.
What helped me in the beginning was: I want to build a milestone. I want to do something achievable that’s going to be an inflection point. And if I really don’t reach it, I need to stop. I need to go look for a job.
I never met a single one of those milestones. Not one. I still pushed through. Because something was still moving. So this is the kind of contradictory lesson: put an end date on your initiative — but at the same time, you probably want to push through no matter what.
Gil: What kept you pushing through when you didn’t meet those milestones?
Pierre: A lot of dopamine. I still had my Airbnb operation at the time, so I didn’t have that sense of urgency bearing down on me. That really helped. But there was also a deep conviction that I was on the right track — that it would just take time to materialize.
The very beginning of Hospitable took about nine months of working day in, day out, night in, night out — on my own. That was a different decade. Things move so much faster now. But after those nine months, I got to a point where I was generating revenue. I could pay myself. And I could start looking toward the future from a place of anticipation rather than anxiety. That’s what I remember from the early days.
Gil: Last question — what’s one piece of tactical advice for someone thinking about getting started in direct bookings or trying to amplify what they already have?
Pierre: I’ll start by acknowledging there are people much better than me at giving tactical advice here.
One thing I’ve seen done really well: embroider your logo or property name on a pillow or cushion and include it in your booking platform photos. The OTA can’t hide it. A curious guest sees it, searches your name, and lands on your website. It’s a simple, low-cost redirect from their platform to yours — and it starts in the photo shoot, not the marketing budget.
The broader thing I want to say for anyone going direct: you are now an entrepreneur. A booking platform has spent decades and billions of dollars building a great booking experience. When you go direct, you’re taking that on yourself. Don’t underestimate the payments side — that’s the part that will demotivate you quickly if you’re not set up for it. But you also don’t have to navigate it alone. That’s exactly what the right infrastructure is there for.
Gil: Pierre, thank you for sharing so much — the releases, the strategy, the philosophy. A lot of folks see “free” and wonder what the catch is. What I got from this conversation is that you see a world with a massive disconnect — hosts without the right tools, unable to be truly independent. And bit by bit, Hospitable is providing those tools so that they can be independent as long as they want, and graduate whenever they’re ready.
Pierre: Yeah, absolutely. Thank you, Gil. Had an amazing time.
Gil: All right. Take it easy. Bye.