“Real fraud that’s aware of your loopholes will not come in looking sketchy.” That’s the moment this episode shifts from guest screening 101 into something a lot more unsettling — and a lot more useful. On this episode of the Booked Solid Show, Gil sits down with Ela Mezhiborsky, Co-Founder and President of Autohost, to talk about guest fraud prevention in an age where AI can fabricate a convincing, sympathetic, entirely fake guest from scratch. Ela walks through how fraud has evolved from fake IDs to synthetic identities, why “gut feeling” is a liability instead of a filter, and why screening guests properly is what actually lets you say yes to direct bookings with confidence instead of fear. Whether you’re just getting your first direct booking site off the ground or you’re managing a growing portfolio, this conversation reframes guest screening as the thing that protects your hospitality — not the thing that gets in its way. Summary and Highlights 👤 Meet Ela Mezhiborsky Ela Mezhiborsky is an industry advocate and public speaker focused on trust and safety as AI reshapes hospitality. A former short term rental operator and Cofounder & President of Autohost, she speaks on “bad AI,” guest verification, fraud risk, bias, and why yesterday’s solutions can’t solve today’s problems. Ela started as an operator running Quickstay, a property management company in Toronto with just over a hundred units, before cofounding Autohost with her childhood friend Roy Firestein, who brought a cybersecurity background to the hospitality problem she was living every day. 🚨 Why an Operator Became a Fraud Fighter Ela didn’t set out to build a guest fraud prevention company. She set out to run a property management business. Somewhere along the way, scale exposed a harder truth: guests could also be the problem.What started as an internal decision tree for her support team, flagging one night local bookings, flagging last minute reservations, flagging certain platforms, eventually collided with something much darker. Escort services. Money laundering. Weapons posted on Instagram from inside a rented unit. That escalation is what pushed Quickstay’s internal spreadsheet into becoming Autohost, a platform now integrated across many major PMS providers, including the ones covered in our Hospitable PMS guide. 🎭 The Guest Who Looks Perfect Might Be the Problem For years, fraud had a look. Fake IDs. Stolen credit card numbers. Sketchy behavior an experienced host could spot.That era is ending. Ela explained how AI now allows bad actors to build synthetic identities from scratch: a convincing photo, a plausible online footprint, a warm story about visiting a daughter at university. These personas don’t look sketchy. They’re built specifically not to.“We’re starting to doubt what we’re seeing,” Ela said, describing a strange new instinct where a guest profile that looks too polished can be more concerning than one that looks rough around the edges. Voice cloning has made it worse. A fraudulent “guest” can now pass a phone call, stay in character under pressure, and even lean on emotional appeals faster than a host can catch them. 📊 Objective Data Beats Gut Feeling Every Time Here’s the part every host needs to hear: intuition is not a screening system. It feels like one, but it isn’t.Ela was blunt about why. “Sketchy” is subjective, and subjective judgment opens the door to real bias, while giving sophisticated fraud an easy way to slip through by simply not looking sketchy at all. Autohost instead builds its guest fraud prevention approach around objective signals: device fingerprinting, whether a credit card was recently flagged, whether an email address was created hours before the booking, whether a listed location matches the device’s actual location.None of this replaces hospitality. It removes the guesswork so a host’s team can stay focused on the guest experience rather than quietly playing detective, a theme that echoes what Abby Grous from Hospitable shared about payment side fraud screening on an earlier episode. 💳 The Chargeback Problem Nobody Budgets For Chargebacks came up as one of the quieter costs of direct bookings, and one of the reasons some hosts hesitate to leave OTAs at all.Ela drew a clear line between two very different problems: real fraud, where a card was genuinely stolen, and “friendly fraud,” where a guest disputes a legitimate charge after the fact. Both hit the same merchant account. The difference is that proper guest verification gives an operator something to fight back with: a timestamp, an electronic signature, a verified ID on file, instead of a guessing game with the payment processor. 🔓 Screening Is an Enabler, Not a Barrier This might be the most important reframe in the episode. Ela argued that treating direct bookings as inherently risky, and responding with blanket rules like “no one night stays” or “no local bookings,” isn’t caution. It’s a financial mistake dressed up as prudence.“Better safe than sorry” sounds responsible. It isn’t strategic. Restrictive policies quietly choke off the direct booking revenue an operator worked hard to build, without actually solving the underlying risk. The fix isn’t more rules, it’s proper screening, paired with a brand guests already trust, the same trust building work covered in building trust on your direct booking site. 🧰 What Guest Screening Actually Costs to Run One thing likely to surprise newer hosts: guest fraud prevention isn’t reserved for large operators anymore. Ela was once restricted to onboarding only larger portfolios at Autohost and got pushback from small hosts who wanted access and couldn’t get it. That gap has closed.Cost typically runs from cents to a few dollars per reservation, scaling with how much verification a jurisdiction or contract requires. Compared against the cost of one bad chargeback, or worse, a property used for something it was never intended for, the math isn’t close. Whatever platform a host uses, a PMS, a direct booking site, or a standalone tool, the point is simply to build a verification step into the guest journey, the same way brand trust and OTA to direct conversion get built into the rest

“Resourcefulness is the ultimate resource.” — Tim Bratz What happens when a commercial real estate operator with 2,800+ apartment units starts converting a slice of that portfolio into short-term rentals — and generating two to three times the revenue on those units? In this episode of the Booked Solid Show, Gil sits down with Tim Bratz, founder of Legacy Wealth Holdings and Smart Management. Tim walks through how he went from a 23-year-old with a maxed-out credit card buying his first $14,000 house, to building and shrinking a portfolio that’s peaked at nearly 5,000 doors and is valued at over $350 million today. But the real story here is what’s happening right now: multifamily operators like Tim are quietly carving off a small percentage of their apartment units, furnishing them, and putting them on Airbnb and VRBO — and it’s opening up a massive opportunity for short-term rental operators to partner directly with commercial real estate owners who are sitting on stressed portfolios and need help generating revenue without taking on debt. If you’ve ever wondered how the STR world looks from the other side of the real estate spectrum — or you’re looking for your next growth opportunity beyond just buying more doors — this conversation will change how you think about where direct booking expertise can go next. Summary and Highlights 👤 About Tim Bratz Tim Bratz is the Founder and CEO of Legacy Wealth Holdings, a commercial real estate investment firm headquartered in Charleston, South Carolina, with a portfolio of roughly 2,800 rental units valued at over $350 million. He’s transacted on more than 6,000 doors across his career, scaling from single-family flips to a multifamily portfolio that once peaked near 5,000 units before Tim intentionally trimmed it down for quality over size. Tim is also the founder of Smart Management, an all-in-one AI-enabled property management platform built to unify leasing, accounting, communication, maintenance, and reporting — for residential, commercial, and short-term rental portfolios — into a single system. He also runs the Legacy Family Mastermind, coaching entrepreneurs on scaling into multifamily real estate, and hosts his own show, The Legacy Podcast. Originally from Cleveland, Ohio, Tim got his start as a real estate broker in New York City before relocating to Charleston in 2008 — right as the housing market collapsed. With no lender willing to bet on an unproven 23-year-old, he financed his first property with a credit card balance transfer check. That resourcefulness became the throughline of everything he’s built since. 🏢 From Broker to 6,000 Doors: The Long Game Tim’s path into real estate started as a commercial broker in New York, closing leases for landlords who were pocketing millions off deals he’d spend hours negotiating on their behalf. That imbalance is what pushed him to the ownership side. After moving to Charleston in the middle of the 2008 crash, he found his first deal — a $25,000 listing he negotiated down to $14,000, funded with a $15,000 credit limit increase on a Mastercard. He renovated it himself, sold it 100 days later, and netted $13,000. He just kept repeating that formula. By 2012, Tim moved into multifamily, drawn to the efficiency of managing one roof and one utility bill instead of eight. Partnerships, flips, and a turnkey rental business followed, before he made a deliberate pivot in 2017: stop flipping single-family houses entirely and go all-in on acquiring apartments. That decision compounded into thousands of units acquired across 2018–2021, before rates, insurance costs, and labor expenses forced a multi-year period of defense — trimming the portfolio down to today’s roughly 2,800 units, still worth over $350 million. For a related look at what disciplined, intentional scaling looks like on the STR side, check out how Fouad Bazzi and Jacinda Neustel built an 82-property portfolio across six markets using the same “growth isn’t just more doors” philosophy Tim describes. 📉 Why Commercial Real Estate Is Taking Arrows Right Now Tim doesn’t sugarcoat the last few years. Multifamily is valued on the income approach — income minus expenses equals net operating income — and while rents stayed largely flat from 2022 through 2026, expenses climbed dramatically: property taxes up over 25%, insurance premiums doubling or tripling in coastal markets, materials up over 40%, energy up 50%. Add in variable-rate loans hitting the steepest Fed rate hikes in history, and a lot of operators found themselves squeezed with no exit strategy — unable to sell, unable to refinance, forced to just hold on and cash flow. Tim’s advice for anyone navigating instability, whether in commercial real estate or short-term rentals: control the controllables. He restructured investor returns, negotiated seller financing, and avoided cementing losses on properties that were still cash-flow neutral, even when they weren’t performing like they used to. The parallel to STR revenue management is direct — operators focused on amenity and property-level upgrades that move revenue are applying the same discipline: control what you can influence, hold steady through what you can’t. 🏠 The Multifamily-to-STR Conversion Play This is the heart of the episode, and it’s a strategy most short-term rental operators have never considered from this angle. At Legacy Wealth’s apartment complexes, Tim typically converts about 5% of units at any given property into furnished, short-term-licensed rentals — the ceiling most lenders will allow before it creates financing complications from over-concentrating revenue in a single stream. The tiered approach looks like this: For multifamily owners feeling squeezed by flat rents and rising expenses, this is a direct lever to boost net operating income without adding debt or units. And here’s where it gets interesting for STR operators specifically: Tim sees this as a wide-open door for short-term rental experts to partner directly with apartment owners who don’t have the team, bandwidth, or hospitality background to run this themselves. That can look like a rental arbitrage lease on 5–10% of a building’s units, a revenue-share or equity-stake arrangement, or simply offering furnishing and management services in exchange for a cut of

🎙️ Why Your Marketing Is Working — But Guests Are Still Booking on Airbnb “You have to build trust on that website. Just being cheaper is not enough.” — Amber Knight You’re driving traffic. You’re running ads. Guests are clicking. And then… they book on Airbnb anyway. If that sounds familiar, this episode is exactly what you need to hear. In this conversation, Gil sits down with Amber Knight, General Manager at BookingsCloud, to pull apart the real reason so many direct booking strategies stall — not at the awareness stage, but at the moment of truth: the booking itself. Amber brings a background most people in short-term rentals haven’t encountered — data-driven advertising built inside a 100-year-old media company, refined through the automotive industry, and now applied specifically to vacation rental portfolios. What she shares in this episode reframes the entire conversation around ads, conversion, and what it actually takes to turn a qualified visitor into a confirmed direct booking. Whether you’re just getting started with direct bookings or you’ve been at it for a while and the numbers aren’t moving the way you’d like, this one is worth your full attention. Summary and Highlights 👤 About Amber Knight Amber Knight is the General Manager at BookingsCloud, a performance marketing company that helps vacation rental managers turn traveler demand into direct bookings. Drawing on her roots in a century-old media company called Advance and years of experience applying data-driven ad technology in the automotive sector, Amber has spent the past two years adapting that infrastructure specifically for the short-term rental space. At BookingsCloud, her team connects directly to a manager’s PMS, builds fully automated, inventory-specific ad campaigns through Meta, and uses an opportunity scoring system to prioritize which properties get ad spend based on revenue potential — not gut instinct. The result is a system that has delivered return on ad spend as high as 100X for established operators. 🔑 What You’ll Take Away From This Episode Before getting into the highlights, here’s the core thread running through everything Amber shares: direct booking conversion doesn’t fail because of bad marketing — it fails because the traffic and the website aren’t working together. Ads bring people in. The website either closes them or loses them to an OTA. Once you understand that, everything changes. 📊 Why Data-Driven Ads Work Differently in This Space Most property managers who run ads are either boosting social posts or running brand-level campaigns that send traffic to their homepage. Amber explains why that approach leaves a lot on the table. BookingsCloud operates differently. Rather than building audience segments manually or targeting by demographics, they feed Meta a rich stream of property-level data — amenities, pricing, photos, descriptions — and let Meta’s machine learning figure out exactly who to put each ad in front of. Every ad is inventory-specific. Every click lands directly on the relevant property detail page, not the homepage. The analogy Amber uses is the automotive industry: if you want a white Toyota 4Runner with a specific trim package and you see an ad for exactly that vehicle at a dealership five miles away, you’re going to click. That same logic applies to vacation rentals. When a guest sees an ad for a property that has the hot tub, the pet policy, the neighborhood, and the nightly rate they’ve been searching for, they’re not settling — and they’re far less likely to get distracted by price. This is a meaningful shift from how most operators think about social advertising. And the data backs it up. 🎯 The Opportunity Score: Spending Where It Actually Matters One of the most practical frameworks Amber introduces is what BookingsCloud calls the opportunity score — a data model that determines which properties in a portfolio should receive ad spend in any given month based on their booking window, revenue potential, and current occupancy. Think about what that solves. A $1,000/night property with one open week and a $300/night property with three open weeks have very different revenue profiles. Experienced managers make these calls intuitively. BookingsCloud makes them systematically, across an entire portfolio, using a data science team. The result is that operators stop spreading ad dollars thin across everything and start concentrating spend where it generates the most return. It’s not about filling last-minute gaps — it’s about applying pressure at exactly the right moment in the booking window for the right property. If you want to understand how scalable direct booking strategies connect to smart ad spend, this section of the conversation is essential listening. 🏠 Why Guests Who Click on Your Ad Still Book on Airbnb This is the part of the episode that will make a lot of operators uncomfortable — and it’s the most important thing Amber says. When BookingsCloud sends guests directly to a property detail page, 20 to 40% of them still end up booking on Airbnb or VRBO. Not because the property isn’t right for them. Because they don’t trust the website. They found the property. They want to book it. But they trust Airbnb to handle things if something goes wrong. That trust advantage — built over years of OTA use — doesn’t go away just because you have a beautiful website. Amber breaks down what actually builds trust on a property page: authentic reviews (including the occasional less-than-perfect one with a thoughtful response), clear evidence that a real person is reachable, and a booking flow that feels familiar. Guests aren’t looking for novelty in how they book — they want the process to feel like something they’ve done before. The moment it feels unfamiliar, conversion drops. Gil adds something equally important from the CraftedStays side: when the booking flow redirects to a PMS engine on a different subdomain, the URL change alone signals to guests that something is off. Consistent domain, consistent session, consistent trust. Building trust on your direct booking site isn’t optional — it’s the difference between capturing a booking and handing it to an OTA.

“The only differentiator between my property doing $254K and my neighbor doing $185K? Design — and the strategy behind it.” What if the gap between a good STR and a great one wasn’t the location, the square footage, or even the amenities — but the intention behind every design decision? In this episode of Booked Solid, Gil sits down with Courtney Petrovich, founder and principal designer of Denori Designs, to unpack why strategy always comes before the furniture. Courtney is both a data-driven investor and a hospitality designer who works across short-term rentals and boutique hotels — and she brings the best of both worlds to this conversation. You’ll hear how she took an eight-bedroom beach duplex from $120K to $254K in annual revenue, why boutique hotels consistently outperform on direct bookings, and the one free thing every host can do today to make guests feel genuinely connected to where they’re staying. Summary and Highlights 👤 About Courtney Petrovich Courtney Petrovich is a real estate investor and the Founder and Principal Designer of Denori Designs, a hospitality design firm specializing in short-term rentals, boutique hotels, and high-performing hospitality spaces. What makes Courtney different is that she’s not just a designer — she’s an active host and investor who underwrites properties, studies market data, and personally operates the spaces she designs. Her process blends narrative-driven environments with real-world operational insight, resulting in properties that look beautiful and actually perform. She holds a Hotel Planning and Design Certificate from Cornell University and is a contributing author in the #1 bestselling book Hospitable Hosts: Sisterhood Edition. She’s also a frequent industry voice on podcasts and stages, including an upcoming speaking appearance at the STR Hospitality Summit. Her current flagship project, The Wesley in Page, Arizona, is a boutique hotel inspired by explorer John Wesley Powell — a property whose design narrative was so compelling it helped the owners raise hundreds of thousands of dollars in investment before the doors even opened. ✨ Key Takeaways from This Episode Before you read the highlights, here’s a quick snapshot of what this conversation covers: 🔬 Strategy First, Design Second One of the most refreshing things about Courtney’s approach is that she doesn’t open a design project with colors or furniture — she opens it with a spreadsheet. “We always start with market research and let that guide us first,” she shares. “What’s performing well? What are competitors doing and not doing? How do we capitalize on the gaps?” This isn’t just theory. At her first North Myrtle Beach property, that research led to a design that targeted two very specific guest types: golfers during shoulder season and multi-generational families during peak. The result was a property that did more than double the revenue of her next-door duplex — same layout, same ocean views, same shared pool and hot tub. The differentiator wasn’t luck. It was a strategy that flowed from data into design. If you want to go deeper on building your guest avatar before you ever pick up a paintbrush, check out this piece on identifying your ideal guest avatar as an STR acquisition strategy. 🏡 From $120K to $254K: A Real Case Study Courtney’s first property had been furnished since the house was built in 2003 — beige walls, gold accents, and seafoam-printed couches. It was doing $120K a year for an eight-bedroom second-row-to-the-ocean home. After doing her market research and identifying her guest avatars, she invested $60K into a full redesign. In the first year post-redesign, the property brought in $254K. Her neighbor in the identical duplex unit, with a more DIY approach to design, is still at $185K. “The ROI numbers when we sit down and analyze them are just mind-blowing,” Courtney says. “You cannot get these returns in the stock market.” And that $60K paid for itself in five months. Everything since has been pure upside. What made the difference? Not just aesthetics. Courtney installed a mini putt-putt inside, added golf club storage at ground level (no more hauling bags up multiple flights of stairs), stocked family essentials like pack-and-plays and high chairs, and designed a color palette and texture story that made guests feel like they were undeniably at the beach — even with the curtains closed. 🎯 Finding Your Ideal Guest Avatar Courtney’s guest avatar process starts broader than most hosts expect. She doesn’t begin in AirDNA or PriceLabs — she starts with travel trends at a regional or national level, understanding why people are coming to a market before she thinks about who they are. From there, she layers in the platform data. And one of her most tactical suggestions? Use AI to summarize competitor reviews. “AI is a great place to be able to look at all the reviews of nearby listings and summarize what people are saying. This person came for a golf trip. This person stayed for their child’s graduation and loved that the dining table could fit everyone.” That kind of insight shapes everything from the amenities you stock to how you describe your property on your direct booking website. For a practical look at how guest avatar research connects to your entire acquisition and marketing strategy, this article is worth a read: Ideal Guest Avatar: The STR Acquisition Strategy That Drives Every Decision Downstream. 🏨 What Boutique Hotels Know That STR Operators Don’t (Yet) Courtney splits her time between short-term rental design and boutique hotel projects, and the cross-pollination of ideas is where this episode really takes off. Sense of Place Boutique hotels start every project by immersing themselves in the story of a location. For The Wesley in Page, Arizona, Courtney and the owners spent three days on-site — hiking local trails, visiting history centers, and learning about the geology of the Colorado River plateau. That immersion led to the hotel’s name, its narrative, and its entire design thread: explorer John Wesley Powell. “Elements from his life are now tied into the design,” Courtney explains. “He kept his exploration notes in

“You can have a perfect property, listed perfectly, with perfect reviews — but if it’s not priced right, people just won’t book it.” — Tim Hubbard What does it actually look like to run a short-term rental business from thousands of miles away, across 40+ cities, in multiple countries — and still deliver a five-star guest experience consistently? That’s not a hypothetical. That’s what Tim Hubbard has built. In this episode of the Booked Solid Show, Gil sits down with Tim, founder and CEO of Corzly, a remote-first hospitality company managing 220+ properties across dozens of markets. Tim is also the host of the Short Term Rental Riches podcast, and he brings more than 11 years of STR experience to this conversation — from his first light-bulb moment comparing Airbnb rental returns to traditional long-term properties, to building a white-label operations model that gives owners back their brand without sacrificing operational control. You’ll hear Tim’s perspective on why the property management model is changing, how AI is reshaping guest communications, what every host needs to have in place before chasing direct bookings, and the one tactic he recommends for anyone looking to grow their direct booking rate starting today. If you’re a host trying to scale without losing the personal connection to your property — or a property manager rethinking how your operations are structured — this one is for you. Summary and Highlights 👤 About Tim Hubbard Tim Hubbard is a real estate investor, entrepreneur, and educator who has been operating in the short-term rental space for over 11 years. Originally from California, Tim now lives in Southern Brazil and runs Corzly — a remote-first hospitality company that serves as the core operating center for STR partners across 40+ cities and multiple countries. To date, Corzly has managed 220+ properties and hosted more than 50,000 guests. Tim is also the host of the Short Term Rental Riches podcast, where he shares quick, actionable solo episodes drawn from his portfolio and the property owners he works with daily. His focus is helping STR operators optimize operations, protect their listing performance, and increase revenue — all without giving up control of their brand. 🔗 Website: www.corzly.com 🎙️ Podcast: www.strriches.com 📘 Facebook: facebook.com/corzly 💼 LinkedIn: linkedin.com/in/tim-hubbard-str 🔑 Key Takeaways From This Episode Managing 220+ properties remotely isn’t luck — it’s infrastructure. Here are the ideas that stood out most from Tim’s conversation with Gil. 🏗️ The White-Label Model: Operations Without Ownership Most property management companies take over your listing and your brand along with it. If things go sideways — poor reviews, inconsistent service — those marks stay with your property permanently. And if you ever want out, you’re often starting from scratch. Corzly works differently. Every listing stays under the partner’s name. Payments flow to the owner. The brand remains theirs. Corzly simply steps in and pulls all the operational levers — guest communications, revenue management, housekeeping coordination, review management — while the owner retains full control of their marketing and their asset. For hosts who still feel deeply connected to their property but genuinely don’t have the bandwidth to manage it themselves, this model addresses a real tension in the market. As Gil noted, many homeowners who built their sites through CraftedStays are exactly this kind of operator — invested in their brand, proud of their property, but needing the right operational partner to make it sustainable. This matters especially because listing performance is tied directly to reviews, and reviews are tied directly to who’s managing the guest experience. A traditional PMC can quietly damage your listing’s ranking with no real accountability. A white-label model keeps that risk on the right side of the table. 🤖 How AI Is Actually Being Used at Scale Tim and his team use AI for guest communications — and the results aren’t just about speed. It’s about consistency. When multiple team members handle guest messages across different shifts, tone and phrasing naturally drift. That drift is a human thing — not a failure. But for guests expecting a seamless experience, even small inconsistencies can erode trust. AI solves this by maintaining one unified voice throughout every touchpoint of the guest journey. Corzly currently uses Conduit as their AI infrastructure and has built custom layers on top of it. One example: if a guest mentions a loose door handle in a message, that feedback is automatically pushed into Breezeway as a maintenance task. No manual handoff. No missed follow-up. This connects to something Gil regularly talks about when it comes to building a direct booking strategy that scales — the systems that remove human error from high-volume operations are the same systems that protect your reviews, your ranking, and ultimately your revenue. What AI doesn’t do well yet, Tim notes, is handle complex operational workflows with multiple decision layers — like early check-in requests, which require confirming housekeeping availability, owner approval, timing parameters, and payment collection. The promise of “AI handles everything” is still a long way from that level of nuance. 💰 Revenue Management: The Piece Most Hosts Underestimate Tim is direct about this: even a beautifully staged, perfectly photographed, and consistently well-reviewed property will underperform if it isn’t priced right. Corzly puts significant effort into revenue management — not just setting rates, but knowing when to offer promotions, which channels to mark up, when to apply discounts for direct bookings, and how to compare performance against the broader market. Tools like PriceLabs play a role, but the strategy behind them is just as important as the tool itself. For hosts just getting started with direct bookings, pricing is often the last thing they optimize — and that’s backwards. You can drive traffic to a beautifully designed website, but if your pricing isn’t competitive in context, you’re still leaving bookings on the table. 📸 The Fundamentals That Actually Move the Needle Before any advanced strategy comes into play, Tim always makes sure a few core things are in place for every property Corzly

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

🌅 From Tragedy to 93 Doors: How One Operator Built Ocean City’s #1 STR Brand With Steve Resnick “It’s not happening to you. It’s happening for you.” — Steve Resnick There’s a moment in this episode where Steve casually mentions a poster board hanging on his bedroom door — 120 little squares, each one waiting for a sticker that represents a new property under management. Every morning, he sees the squares. Every morning, he asks himself the same question: what do I need to do today to get closer to the goal? That single image tells you almost everything you need to know about how Steve Resnick operates. In a short-term rental industry full of operators chasing growth in every direction, Steve’s discipline is almost old-school. Pick a number. Make it visible. Make decisions through it. This conversation digs into how that focus translated into 93 properties in Ocean City, New Jersey — and what it actually takes to deliver consistent five-star experiences at that scale. 🏖️ 👤 Meet Steve Resnick Steve Resnick is the visionary founder and CEO of HeavenlyRez Vacation Rentals, the fastest-growing short-term rental company in Ocean City, New Jersey. He has redefined what modern hospitality looks like — blending technology, heart, and human connection to deliver a five-star experience for both guests and homeowners. Under his leadership, HeavenlyRez was ranked #1 Property Management Company by AirDNA in 2025 for the Ocean City, NJ market and has earned thousands of five-star reviews — the most in the region. The company maintains an industry-leading 6.5-minute average response time and offers 24/7 guest and owner support. Steve is a Certified Short-Term Rental Co-Host, Multi-Year Golden Host Award Winner, and STR Secrets Boardroom Member. He’s been featured on multiple short-term rental podcasts, served as a panel speaker at the STR Wealth Conference, and is a #1 Best Selling Author for his contribution to Hospitable Hosts: Couples Edition. 🧭 The Origin Story Behind HeavenlyRez Steve’s path into hospitality wasn’t planned. After more than 20 years in technology program management at a major financial institution, he and his wife Kim bought a beach property in Ocean City in 2015 — somewhere to make memories with their young daughter. Then came tragedy. Their four-year-old daughter passed away. The property they’d planned to fill with family vacations became something else entirely: a place to rebuild. When they eventually had another daughter, they returned to Ocean City and started thinking about creating that experience for other families. Frustrated with the local management company handling their rental, Steve took it over himself — and the numbers immediately spoke for themselves. One property became three. Then COVID hit. Then a neck injury sidelined him from his corporate role. He used the recovery time to get his realtor’s license, build a vision, and commit fully to the business that had been quietly growing on the side. Three years later, he’s at 93 doors with a clear runway to 120 by the end of 2026. The chapter he co-authored in Hospitable Hosts: Couples Edition is appropriately titled Never Let a Good Crisis Go to Waste. 🌊 🎯 The Vision Board That Drives Every Decision The poster board on Steve’s bedroom door isn’t just motivational decor. It’s a decision-making framework. When he started hiring, he didn’t hire for where the business was — he hired for where it was going. When he evaluated whether to lease a 5,800-square-foot commercial building (the new HeavenlyRez Hospitality Hub), the question wasn’t do I need this today? It was will I need this at 120 doors and beyond? This is the kind of forward-looking discipline that’s easy to nod along with and surprisingly hard to execute. Most operators react. Steve plans the gap between current state and target state, then closes it methodically. For more on this mindset shift, the scaling a short-term rental business with systems breakdown covers why infrastructure has to outrun door count. 🏢 Why HeavenlyRez Built a Centralized Hospitality Hub One of the most fascinating operational decisions Steve shares is the move toward centralizing inventory and amenities in a dedicated facility — instead of relying on owner closets at each individual property. His logic is brutally honest: every property is essentially a separate warehouse. Owners leave closets unlocked. Cleaners can’t always control what guests take. Inventory levels vary by location. At three properties, you can manage that chaos. At 93, you can’t. By consolidating amenities — standardized Keurig and drip coffee makers, beach chairs, beach tags, luxury essential kits with shampoo and conditioner, paper goods, even pizza cutters — into one central hub, HeavenlyRez removes variability from the guest experience. A guest who books a beachfront condo gets the exact same amenity standard as one who books a bayfront unit. “The most important thing for a guest is their first impression. Is it clean? Is it consistent? When you go to a Marriott, you always know what you’re getting. I wanted that for every single one of our properties.” This kind of standardization is also why HeavenlyRez doesn’t take properties outside Ocean City. Geographic focus isn’t a limitation — it’s the unlock. The team, the warehouse, the SOPs, and the cleaning crews are all built around one market. 🛠️ Inside the HeavenlyRez Tech Stack Steve’s background in technology shows up in nearly every layer of the operation. The current stack includes: The smart device layer alone is doing meaningful work. Unique guest codes are auto-generated and activated only during the check-in window. Thermostats automatically shift to eco mode the moment a guest checks out. Door sensors shut off the AC if the patio door is left open for more than 10 minutes. Water sensors have prevented countless leaks before they became real damage. This is the kind of infrastructure that enables HeavenlyRez to deliver a 6.5-minute average response time — because the system flags problems before guests or owners ever have to. 🤖 Where AI Fits Into the Operation The most forward-leaning part of the conversation is about AI.