Vacation Rental Success

Hosted by Heather Bayer aka @CottageGuru

BusinessInterviews guestsExplicit

Website RSS feed

Episodes

689

Latest episode

Nov 2026

Language

About the show

Heather Bayer, author of Renting Your Recreational Property for Profit, former CEO of a highly successful cottage rental agency, and a popular blogger, hosts the Vacation Rental Success podcast. With many years experience of owning and managing multiple vacation rental properties, Heather brings her knowledge and views on every aspect of the business, together with interviews with vacation homeowners and industry experts. Heather has appeared as a guest on CTV Canada, CBC Radio, Rogers TV, and Chex TV and is frequently interviewed on real estate and travel topics by magazines and daily newspapers.

Listen to episodes

60 recent

November 11, 202645 min

VRS689 - Muse, GrokBot, Dots and Duet, and What Agents Actually Do

The Vacation Rental Success Podcast and The Grounded Briefing are supported by toolWYZE™, flat-priced tools for small short-term rental property managers that solve your everyday operational issues. Find Out More >> Want AI to take on the drafting without handing over the keys? This free playbook, Permission to Build, walks you through 30 short steps to your first AI crew. Get Access >> A few months ago, running your own AI agent meant buying a Mac Mini, leaving it switched on in a cupboard and spending a weekend wiring it to your email. I read the instructions, looked up the price, and quietly closed the browser tab. Then, in the space of about ten weeks this fall, four of the biggest AI companies released their own versions of exactly that, and now it lives on your phone. In this solo episode I explain in plain language what these new personal agents are and how they differ from the chatbots most of us started with. I walk through each of the four: Muse from Meta, GrokBot from xAI, Dots from OpenAI and Claude Duet from Anthropic, including what each one costs, who it is built for, and what I am actually using it for. Then I get practical. You will hear six jobs I would hand to an agent if I were running a portfolio today, why you should compare the cost with a virtual assistant rather than a chatbot subscription, and how to use more than one of these tools without losing track of your own work. I learned that last one the hard way. About the host Heather Bayer has worked in the short-term rental industry since 1998 and ran CottageLink Rental Management in Ontario for almost 20 years, growing it to around 200 properties before selling in 2022. She has hosted the Vacation Rental Success Podcast since 2013 and now runs an AI consultancy helping small and mid-sized vacation rental companies adopt AI responsibly. She tests these tools in her own business first so she can tell you honestly what works. Key takeaways An assistant answers the questions you thought to ask. An agent notices the ones you didn't, works in the background on its own cloud computer, and checks with you before doing anything that matters. Start with one agent, ideally the one that matches the AI tool you already use most, because that is where your history and settings live. Muse has a free tier if you just want to try the idea. Agents use tokens every time they act, including every scheduled check whether or not there is anything to find. Start with a few scheduled tasks, review your usage after a week, and ask whether hourly could be daily. Judge the cost against a virtual assistant, not a $20 chatbot subscription. You are paying for work done on your behalf, which frees your human team for the guests and owners who need a person. Give each tool one job and stick to it, then send all finished work to a single folder. It is the key safe principle: it doesn't matter who used the key, it always goes back to the same place. Keep your instructions, tone of voice and key processes in a document you control, so you can move to a new agent without starting again. Never let an agent message guests on its own, and keep it well away from owner bank details and guest payment information. 📣 Work with Heather This episode is also brought to you in part by Vacation Rental Formula Business School Consultancy with your host Heather Bayer. If you run a short-term rental or property management business and want help with growth, operations or putting AI to work safely and consistently, Heather offers 1:1 consultancy and fractional Chief AI Officer support. She brings 30 years of industry experience, including two decades running her own property management company, and she'll help you find where the overwhelm sits and what to fix first. 🌐 Find out more at VacationRentalFormula.com/Consultancy Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/podcast/vrs689

November 4, 202649 min

VRS688 - Trading Cards, AI Agents and the End of Tool Overload

The Vacation Rental Success Podcast and The Grounded Briefing are supported by toolWYZE™, flat-priced tools for small short-term rental property managers that solve your everyday operational issues. Find Out More >> If you were at VRMA in Nashville this year, you may well have come home with a pack of trading cards featuring a hundred familiar faces from the vacation rental industry. Jan Sahagun is the person behind them, and in this episode he explains where the idea came from, how the cards were chosen and produced, and why a $7,000 marketing experiment ended up booking far more demos than he ever expected. Jan has spoken with thousands of property managers over the past three years, and he hears the same complaint everywhere: too many tools, none of which talk to each other. Heather and Jan talk about how AI agents are starting to change that, moving beyond guest messaging into day-to-day operations, and what this means for traditional property management software. Jan also makes a case some listeners may find surprising: don't switch your PMS right now. The conversation closes with a reminder that applies to all of us using these tools. Use AI to sharpen your thinking, not to replace it. About Jan Sahagun Jan Sahagun is co-founder of Trellis, a Y Combinator company building AI agents that run operations for property management companies, and founder of STR Tech Report, a free directory of the tools available to vacation rental operators. Originally from Barcelona, Jan studied at McGill University in Montreal, played hockey along the way, and worked in investment banking and procurement before moving into sales. He joined the industry selling AI guest communication software, and co-founded Trellis with Lodovico Benvenuti, who runs a 150-listing property management company in Milan. Key takeaways The most common complaint Jan hears from property managers is tool fragmentation: separate systems for guest messaging, operations, pricing and the PMS, with no single place to manage it all. Jan doesn't recommend switching PMS right now. If you must, compare the API documentation of each system (the technical detail of what other tools can connect to) and choose the one that allows the most. Then hand those documents to Claude to do the comparison for you. AI guest messaging often falls short because it lacks operational context. An agent that knows who is working, where they are and what they can fix can resolve an issue end to end, rather than sending an apology and escalating. Direct booking websites remain essential, because AI booking assistants can only offer your direct rate if they can find your site. They now need to be built so these assistants can read them. The cards worked because they were about people, not the brand. Personal, thoughtful marketing gets kept; generic giveaways get thrown away. Use AI to build on your own ideas, not to have them for you. Keeping your own thinking active is what protects your expertise. 📣 Work with Heather This episode is also brought to you in part by Vacation Rental Formula Business School Consultancy with your host Heather Bayer. If you run a short-term rental or property management business and want help with growth, operations or putting AI to work safely and consistently, Heather offers 1:1 consultancy and fractional Chief AI Officer support. She brings 30 years of industry experience, including two decades running her own property management company, and she'll help you find where the overwhelm sits and what to fix first. 🌐 Find out more at VacationRentalFormula.com/Consultancy Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/podcast/vrs688

October 28, 202649 min

VRS687 - Fewer Sessions, More Action at the Direct Booking Success Summit

This Episode is Sponsored by The Simon Lehmann Academy Simon Lehmann STR Academy is a self-paced course for property managers growing from around 20 to 200 homes and beyond. Built around the journey "From Operator to CEO," it includes nine modules and 52 episodes covering the operating model, contracts, KPIs, unit economics, tech stack and exit readiness. It's designed to help professional short-term rental operators build the structure needed to scale beyond a founder-dependent business. Visit - Simon Lehmann's STR Academy ________________________________________________________________________________________________________________________________________ Every fall, a few weeks before the Direct Booking Success Summit , I sit down with Jenn Boyles, the host who created it. This is Jenn's fourth visit to the show, and this year we start somewhere unexpected: with Jenn explaining why she cut her own event almost in half. Last year's summit ran 47 sessions for around 1,000 hosts from more than 40 countries. People left with pages of notes, and Jenn started to wonder how many of them would act on any of it. We also talk about Airbnb's new "direct booking link" for hosts and why Jenn says it is nothing of the kind, how she runs her one-person business with a team of named AI agents, and how AI has found its way into this year's program through sessions on AI search, channel profitability and building an AI business brain. The 2026 summit runs online from November 17 to 19. If you manage short-term rentals and want three days that end with something done rather than a notebook full of good intentions, this conversation will help you plan for it. About Jenn Boyles Jenn Boyles is the founder of Direct Booking Success and the creator of the Direct Booking Success Summit , the free online event she has run every November since 2021. She started hosting in Europe in 2012, learned from a chalet in the Austrian Alps that wouldn't book, that a listing on a crowded platform isn't a business, and opened the Liverpool Boat in 2019 at 80% direct bookings. When the mass cancellations hit in 2020, her calendar held. Now based in Vancouver, she helps hosts and property managers build their own marketing through the STR Content Lab and the DBS Control Room, where clients build teams of AI agents to take on the work that doesn't need them personally. Key takeaways If every booking comes through one platform, you are an accommodation provider to that platform. A business you can rely on needs more than one source of guests. Airbnb's new host "direct booking link" carries a lower commission, but the guest, the booking and all the communication stay on Airbnb. A true direct booking comes through your own website. More information doesn't change a business, action does. Jenn's advice for the summit is to pick a day, pick a theme and do one action. Before you build AI agents, give them a foundation. Jenn starts every client with their brand, voice, goals and business detail, then a task audit of everything they do that doesn't actually need them. Agents only know what they can see. One Control Room member's "no bookings today" report turned out to be her deleting the booking emails before the agent could read them. The fundamentals of direct booking marketing haven't changed: local content, blog posts and a strong website. AI search rewards the same work, done well. ______________________________________________________________________________________________________________________________________ 📣 The AI Ambassador Program This episode is also brought to you in part by our AI Ambassador Program . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our AI Ambassador Program . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at VacationRentalFormula.com/AI Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/podcast/vrs687

October 21, 202656 min

VRS686 - Don't Let AI Be the Box on Your Shelf

This Episode is Sponsored by The Simon Lehmann Academy Simon Lehmann STR Academy is a self-paced course for property managers growing from around 20 to 200 homes and beyond. Built around the journey "From Operator to CEO," it includes nine modules and 52 episodes covering the operating model, contracts, KPIs, unit economics, tech stack and exit readiness. It's designed to help professional short-term rental operators build the structure needed to scale beyond a founder-dependent business. Visit - Simon Lehmann's STR Academy ________________________________________________________________________________________________________________________________________ A year after the AI skills lab at VRMA in Las Vegas, with VRMA Nashville just behind us, I wanted to check where the industry really is with AI. Two conversations in the same week prompted it. One was a senior manager who told me she opened Claude six months ago, wasn't sure what to do with it, and closed it again. The other was Jodi's beginner training camp, where the most answered question showed that most people had either never started, or had tried once, got intimidated, and stopped. Jodi Bourne is back for her eleventh appearance on the show, and together we work through the four groups we see in our client work: the builders, the buyers, the one-person shows and the non-starters. We talk about why the foundations matter more than the tools, what to pay attention to and what to ignore after a conference full of AI vendors, and the safety guardrails most businesses still haven't put in place. We close with ten practical first steps for anyone who hasn't started yet, and a look ahead to the six-week Get Started series Jodi and I are running together in November and December. ‍ About Jodi Bourne Jodi Bourne works with short-term rental operators on marketing, brand messaging and AI adoption, and has become one of the most practical AI teachers in the industry. Her Hospitality Business Brain gives operators a structured foundation of guest avatars, brand voice, owner story, reviews and a property matrix, so that every AI tool they use works from accurate information. She runs the Savvy Hosts Lab foundations course and beginner training camps, sets up team-wide AI systems for property management companies, and is relaunching her podcast, The Savvy Host Advantage, with a series on AI. She is a teacher at heart, and it shows in how she works with clients. ‍ Key takeaways Most operators haven't failed at AI, they've stalled. They opened a tool, didn't know what to do with it, and put it back on the shelf, and confidence comes from seeing one skill change one real output. When each team member uses a different AI tool with no shared brand voice or business information, the business ends up with inconsistent output and real data risk. Pick one tool, share the foundations, and have one person lead. Your business brain is only as good as what's in it. One forgotten FAQ in an old upload sent guests hunting for a property that no longer existed, so keep one source of truth and update it when anything changes. Before buying a new AI product, check what's already built into the tools you pay for, and ask your AI how you could do the same job yourself. Several of Jodi's clients have replaced guidebook and messaging subscriptions this way. Smaller operators have a real opening right now with AI search. Better blogs and better content are already helping small companies show up ahead of larger ones in some destinations. Write a one-page AI policy covering what never goes into AI (guest personal data, owner financials, card details), which tool the team uses, and the rule that a person checks everything before it goes out. ______________________________________________________________________________________________________________________________________ 📣 The AI Ambassador Program This episode is also brought to you in part by our AI Ambassador Program . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our AI Ambassador Program . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at VacationRentalFormula.com/AI Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/podcast/vrs686

October 14, 202645 min

VRS685 - From Reservation Data to Dashboard in 15 Minutes

This Episode is Sponsored by The Simon Lehmann Academy Simon Lehmann STR Academy is a self-paced course for property managers growing from around 20 to 200 homes and beyond. Built around the journey "From Operator to CEO," it includes nine modules and 52 episodes covering the operating model, contracts, KPIs, unit economics, tech stack and exit readiness. It's designed to help professional short-term rental operators build the structure needed to scale beyond a founder-dependent business. Visit - Simon Lehmann's STR Academy ________________________________________________________________________________________________________________________________________ Maria Lancaster spent much of her career in high tech, with companies like Oracle, until her home was effectively an airplane. She traded that for a beach house on Tybee Island and a job at Tybee Vacation Rentals, where she found that everything she knew about technology had a real home in short-term rentals. In this episode, Maria and Heather talk about what has changed for anyone who wants to build. Dashboard pages that once took Maria weeks of SQL and programming now come together in about 15 minutes of plain English requests to Claude. She walks through Helm, the dashboard she built in three days for the Wheelhouse Hackathon, including a what-if revenue planner and a way to make sense of parent-child properties, and she is candid about where she got stuck. If you manage a portfolio and have wondered whether you could build your own tools, Maria gives you a starting point you could act on this week. She is also very clear about when you should build and when you should simply buy the software that already exists. About Maria Lancaster Maria Lancaster is the founder of MJ Creative Business Solutions, a deliberately broad name for a boutique consultancy that helps short-term rental companies with revenue management, business intelligence and marketing. Before joining the industry she spent years in technology marketing at companies including Lotus and Oracle. She moved to Tybee Island, Georgia, joined Tybee Vacation Rentals, and stayed on after VTrips acquired the company before going out on her own. Maria is part of ShortCuts for Short Term Rentals and describes herself as a knowledge sharer who is always happy to answer a question. Key Takeaways You can start without any connections at all: export around three years of reservation detail (the individual reservations, not the summary) from your PMS, bring the spreadsheet into Claude or ChatGPT, and start asking questions. If you are not sure what to ask, ask the AI what your first question should be, or ask whether it understood your question and how it would have phrased it. Once you have seen what an export can tell you, ask your PMS, revenue and review vendors about their MCP, the connection that lets your AI read their data, so you can do the same thing on live numbers. Unless you want to become a technology company, do not build your core software. Your business is hospitality, so build the extras that make your owners, your team and your guests happier. AI can help you spot owners at risk before they give notice. The quiet ones you have not heard from in six months are often the ones who leave, and AI can also help you plan what to say when you call them. Maria expects guests and owners to find, book and evaluate managers through AI tools rather than websites within the next year or two, so it is worth thinking now about how your business will show up there. ______________________________________________________________________________________________________________________________________ 📣 The AI Ambassador Program This episode is also brought to you in part by our AI Ambassador Program . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our AI Ambassador Program . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at VacationRentalFormula.com/AI Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/podcast/vrs685

October 7, 202650 min

VRS684 - The Best Surprise Is No Surprise: Why Vacation Rentals Need Standards

This Episode is Sponsored by The Simon Lehmann Academy Simon Lehmann STR Academy is a self-paced course for property managers growing from around 20 to 200 homes and beyond. Built around the journey "From Operator to CEO," it includes nine modules and 52 episodes covering the operating model, contracts, KPIs, unit economics, tech stack and exit readiness. It's designed to help professional short-term rental operators build the structure needed to scale beyond a founder-dependent business. Explore the Simon Lehmann STR Academy: simonlehmann.net/academy Ashley Ching is back on the show for a third time, and this conversation goes somewhere the earlier two did not. Her new white paper, Reasonable Hospitality, argues that vacation rentals are sitting exactly where American motels sat in the 1950s: an explosion of supply, wildly uneven quality, and guests forced to inspect before they trust. Hotels solved that with standards and tiers. We never did. Instead we handed the job to review scores, and Ashley makes a persuasive case that we are asking reviews to do something they were never designed to do. Heather invited Ashley back because the paper puts numbers on an idea Heather has circled for years. The thing that separates a $135 stay from a $2,500 stay is not the sheets or the view or the price. It is the Care Coverage Ratio, how many local people are there to help when something goes wrong. And something always goes wrong. Along the way they get into the difference between personalization and care, why airlines are a cautionary tale for anyone racing to automate, what a hotel in Jacksonville taught Heather about a carton of milk, and which parts of a property management business should have been automated years ago. About Ashley Ching Ashley Ching spent thirteen years at Tiffany & Co., finishing as Head of Global Merchandising Operations, then ran merchandising for The Company Store, the Home Depot owned bedding brand. A run of disappointing family rental stays, including a ski house that slept sixteen and owned eight plates, led her to found Inhaven in 2022. What began as a wholesale supply platform for property managers has become a standards business. Her August 2026 white paper, Reasonable Hospitality, proposes the first shared language of trust for vacation rentals: Signature, Premium and Lifestyle tiers, each defined by measurable service and comfort standards. Key takeaways Discoverability and predictability are two different problems. The OTAs solved the first one. Nobody has solved the second, which is why guests still zoom into forty photos and read a hundred reviews before booking. The strongest predictor of a hospitality tier is the Care Coverage Ratio: one local staff member per five homes at Signature, one per ten at Premium, one per fifteen at Lifestyle. Companies that ran at one to twenty marketed themselves as technology businesses, and both went bankrupt. A five star review tells you a promise was kept. It does not tell you what the promise was. A perfect score on a $135 container home and a perfect score on a $2,500 estate mean two entirely different things. Standards belong at the property manager level, not the property level. Every home can stay unique. What the manager controls is the service level and the high velocity items: the sheet that replaces a torn sheet, the pillow, the coffee maker. Personalization is knowing a guest likes 2% milk. Care is noticing they look unwell and asking what they need. AI can do the first. Only a person can do the second. Automate the back office, the inventory, the replenishment and the maintenance tickets. Be very careful about automating the moment a guest needs a human. Even McDonald's has started rehiring after deciding it went too far. Most managers end up excellent at one tier. They shed the Lifestyle homes that do not return the service invested, and the Signature homes where they keep missing expectations. Choosing your tier is choosing your operating model. 📣 The AI Ambassador Program This episode is also brought to you in part by our AI Ambassador Program . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our AI Ambassador Program . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at VacationRentalFormula.com/AI Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/podcast/vrs684

September 30, 202652 min

VRS683 - Why AI Cannot Fix a Broken Business Model

This Episode is Sponsored by StayFi Your ultimate tool for Vacation Rental WiFi marketing allowing you to collect guest emails automatically via custom captive WiFi login splash pages. Drive repeat direct bookings and convert your OTA bookings to book direct for their next visit. Visit https://stayfi.com/vrsuccess/ and use code VRSUCCESS for 50% off 3 months of StayFi service. ________________________________________________________________________________________________________________________________________ Everybody in short-term rentals is talking about AI. So when Heather sat down with European consultant Cristiana Carpini, the question she really wanted answered was whether property managers on the other side of the Atlantic are talking about it too, or whether something else entirely is keeping them awake. The answer was blunt. Margins are shrinking, OTA dependence is rising, owner acquisition is harder, and teams are overloaded. Operators call Cristiana believing AI is the fix, and she tells them what they do not want to hear: AI cannot repair a broken business model, it can only automate a broken business faster. From there the conversation opens out into the real differences between running this business in Europe and in North America, from GDPR and owner expectations to employment law and competitive culture. It also covers what makes a property management company sellable, why that takes three years rather than three months, and why Cristiana founded the Women Vacation Rental European Conference. About Cristiana Carpini Cristiana Carpini is the founder and CEO of Tara Home Consulting, working with property managers across Europe on audits, business plans, restructuring and exits. She came into the industry by accident after five years as a guest relations manager on cruise ships, then spent years inside the big European brands including Novasol, Interhome and Belvilla, running markets in Italy, France and Croatia. She launched Tara Home Consulting during the pandemic, giving free advice to panicking operators, and never stopped. She is also the founder of the Women Vacation Rental European Conference. Key Takeaways AI cannot repair a broken business model. If the margin structure underneath the business does not work, automation makes the problem arrive faster rather than fixing it. What European operators actually bring to a consultant is shrinking margins, OTA dependence, harder owner acquisition and overloaded teams. AI is further down the list than the conference circuit suggests. Owner relationships are the one thing not to automate. Cristiana describes an owner who complained about pricing when the real problem was his mother's illness and his need for more money. No AI would have surfaced that. Europe is not one market. Drive two hours and you are in a different country with different tax, language, rules and owner expectations. Southern European owners are emotionally attached to their homes; northern European owners often are not. Employment rules vary just as sharply. An Italian employee may accept a 24 hour emergency call-out where a French employee is protected by far stricter rules, so expansion planning has to account for labor law, not just demand. Preparing a company for sale usually takes three years. Sell faster than that and you leave money on the table, because valuation looks at reviews, brand, website and direct bookings, not just EBITDA. The business has to become independent of its founder. Heather hired her own replacement three years before selling Cottage Link, precisely so the buyer was not buying a company that only worked with her in it. ______________________________________________________________________________________________________________________________________ 📣 The AI Ambassador Program This episode is also brought to you in part by our AI Ambassador Program . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our AI Ambassador Program . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at VacationRentalFormula.com/AI Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/podcast/vrs683

September 23, 202648 min

VRS682 - What It Takes to Rebuild a Company on AI

This Episode is Sponsored by StayFi Your ultimate tool for Vacation Rental WiFi marketing allowing you to collect guest emails automatically via custom captive WiFi login splash pages. Drive repeat direct bookings and convert your OTA bookings to book direct for their next visit. Visit https://stayfi.com/vrsuccess/ and use code VRSUCCESS for 50% off 3 months of StayFi service. ________________________________________________________________________________________________________________________________________ Brooke Pfautz has been a guest on this show more often than almost anyone, and he has never come back with the same story twice. This time he arrives having taken his own company apart. Vintory, the business he founded seven and a half years ago to help professional managers grow their inventory, has been rebuilt from scratch as an AI native platform, launched this month as Vintory AI. The work was done by a small team reporting directly to Brooke, outside the main company, and most of his staff did not know it was happening. Heather brings him back because of a single line in a video he posted: "Most companies spend too much energy protecting the business they already have instead of building the one that is coming next." The conversation works through what it took to act on that line, and what it cost. For anyone walking the halls at VRMA this October, or weighing up a tool with AI on the banner, this episode gives you a way to tell the genuine article from the retrofit. It also gives you Brooke and his team's four-part formula for any AI system, whether you buy one or build it yourself, and an honest look at what has changed in owner acquisition and what has not changed at all. About the guest Brooke Pfautz founded Vantage Resort Realty in Ocean City, Maryland, grew it to 500 properties under management, and sold it in 2013. He spent five years as chief business development officer for a large management company in Orlando, then moved into software with LiveRez, which is where he fell in love with the technology side of the business. Seven and a half years ago he founded Vintory with a single mission that has not changed since: help professional vacation rental managers grow their inventory. Vintory has now worked with more than 1,000 companies on the supply side, and Brooke is a familiar voice on owner acquisition across the industry. Key takeaways AI native and AI wrapped are not the same thing, and the difference shows up in how fast a company can ship. Brooke reckons 90 percent of the booths at VRMA will have AI on them, and 90 percent of those are dabbling on the fringes. Every AI system needs four parts: context, rules, skills and connectors. Miss any one of them and you get slop. Brooke's team remembers it as "Can Robots Sign Condos?" Context is the ingredient most people skip. Feeding a system your history, your positioning, your brand voice and your avatars is what separates usable content from generic filler, and both Brooke and Heather write iteratively rather than accepting a first draft. Owners have not changed. They still want to know they can trust you, that they will earn more, that their home will be looked after, that you will communicate, and that guests will be well hosted. What AI changes is the ability to reach the right owner with the right message at the right time, at far greater scale. Rebuilding proved easier than retrofitting. Launching new features at Vintory used to take months and now takes weeks, which is the practical argument for starting over rather than bolting AI onto an existing platform. Nobody hires Vintory because they want AI. They hire because they want more management contracts. The technology is the means, and the result is the only thing that counts. _______________________________________________________________________________________________________________________________________ 📣 The AI Ambassador Program This episode is also brought to you in part by our AI Ambassador Program . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our AI Ambassador Program . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at VacationRentalFormula.com/AI Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/podcast/vrs682

September 16, 202650 min

VRS681 - When 120 Property Managers Became Software Builders

This Episode is Sponsored by StayFi Your ultimate tool for Vacation Rental WiFi marketing allowing you to collect guest emails automatically via custom captive WiFi login splash pages. Drive repeat direct bookings and convert your OTA bookings to book direct for their next visit. Visit https://stayfi.com/vrsuccess/ and use code VRSUCCESS for 50% off 3 months of StayFi service. ________________________________________________________________________________________________________________________________________ This summer Andrew Kitchell opened up Wheelhouse and invited his customers to build on top of it. Not engineers. Customers. Property managers, revenue managers, and a fair number of people who had never built anything in their lives. Over four days, 120 people from six continents worked together, and 40 of them finished with a working prototype. The top prize of $5,000 went to a full-time property manager who had never told anyone he was interested in building software. Heather has spent her own summer building, so she came to this conversation with the question she keeps turning over: if someone with no coding background can build a working app, does that mean every property manager should? Andrew has a clear answer, and it has nothing to do with the tools. His view is that the barrier is no longer technology or design or user experience. It is permission. Giving yourself permission to stop doing what you normally do and decide that today is a build day. Along the way they get into what a hackathon actually is, why Wheelhouse now describes itself as a growth company rather than a pricing company, how MCPs let you ask questions of your portfolio in plain language, and where building your own tools earns its keep against where it becomes an expensive hobby. About Andrew Kitchell Andrew Kitchell has been in and around the short-term rental space for around fifteen years, starting as an Airbnb host in San Francisco while the platform itself was being built a few blocks away. He joined an eight-person urban rental company that was updating its prices by hand twice a week, spent a weekend hacking the Airbnb API to automate it, and four weeks later the business had pivoted into Beyond Pricing. He went on to found Wheelhouse and the operating company Lyric, and has run both technology businesses and operating businesses through some hard cycles, including losing Lyric entirely when COVID hit. Wheelhouse today connects to around 800,000 listings and has opened its full platform to anyone who wants to build on it. Key Takeaways The barrier to building your own tools is no longer technical skill. Andrew argues it is permission, the decision to stop doing today what you normally do and treat a few hours as build time. If you can describe a problem clearly, you are much closer to solving it than you think. Property managers describe their operational problems better than almost anyone, and that description is now most of the work. The old software model asked the person who understood the customer to hand that understanding to an engineer and hope it survived the journey. That gap has closed, and the people closest to the problem can now solve it themselves. You do not have to build anything yourself to benefit. Direct booking sites, owner reports, and small internal tools are all cheaper and faster to produce now, whoever builds them. Building is worth the time when it lands in your quieter season and when what you learn carries into the next build. Treat the first few attempts as research and development, not as finished product. MCPs remove the need to understand APIs at all. Connect Wheelhouse to Claude and you can ask questions of your portfolio and execute pricing strategy in ordinary language, which Andrew sums up as a click is a command, is a chat. An open platform produces better outcomes than a single one. After the hackathon there is no longer one Wheelhouse experience, there are forty-one, each built by someone who knew exactly what they needed. _______________________________________________________________________________________________________________________________________ 📣 The AI Ambassador Program This episode is also brought to you in part by our AI Ambassador Program . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our AI Ambassador Program . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at VacationRentalFormula.com/AI Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/podcast/vrs681

September 9, 202651 min

VRS680 - What Autism Families Actually Look For In Your Listing

This Episode is Sponsored by StayFi Your ultimate tool for Vacation Rental WiFi marketing allowing you to collect guest emails automatically via custom captive WiFi login splash pages. Drive repeat direct bookings and convert your OTA bookings to book direct for their next visit. Visit https://stayfi.com/vrsuccess/ and use code VRSUCCESS for 50% off 3 months of StayFi service. ________________________________________________________________________________________________________________________________________ A while back I talked with Suzanne Young (ex-Hacker) about how to prepare a property for guests with autism. That conversation covered the host's side of it. This one covers the other side, which is what the families themselves are looking for, and what they wish they could find out before they book. Eloisa Jones is a travel designer who plans sensory-friendly trips for neurodivergent families. She is also an autism parent, a short-term rental owner, and the writer of a weekly newsletter that has now run for seventy-one weeks without a break. What she brings to this conversation is a level of detail most of us have never had to think about. The light bulb that gives off a high pitch. The ceiling fan that throws a flicker across the room. The blanket that clumps if it is dried on the wrong cycle. The bleach smell that turns an arrival into a migraine. The second half turns to search. Families are now asking ChatGPT for a sensory-friendly rental with low lighting and no open floor plan, and Eloisa is blunt about what that means for your listing. If your website does not say those things, you will not be found. About Eloisa Eloisa Jones is the founder of Gathering Memories Travel and the writer of The Autism Passport newsletter. Born in Mexico City, she spent eighteen months living in Japan, and she has traveled for more than twenty years with family members on the autism spectrum. She holds four certifications in autism and accessible travel, including IBCCES and Autism Double-Checked, and has owned and run her own short-term rental since 2019. The travel business funds a longer-term goal, which is a nonprofit supporting autistic young adults at the point where school-age support ends. Key Takeaways Family-friendly tells an autism family nothing. Specifics do. Which bedroom is quietest, how far the property sits from a main road, whether the yard is fenced, how many steps there are to the door, whether the washing machine backs onto a living space. Most of what makes a property autism-ready costs very little. Warm dimmable bulbs that do not flicker or give off a high pitch, cleaning products without harsh chemicals, an air purifier run before arrival, a smooth blanket for the couch, microfiber sheets that do not pill. Scent is a bigger problem than most owners realize. Plug-ins, scented candles, heavy diffusers and the bleach some cleaners leave behind can trigger a migraine the moment a family walks through the door. Eloping matters and most listings never mention it. Families with a child who runs need to know about door safety, road proximity and fencing before they book, and inexpensive door stops address more of this than owners expect. Search has changed. Families are typing whole sentences into ChatGPT, so listings need the actual phrases: sensory-friendly, low stimulation, neurodivergent welcome, predictable environment, single story, blackout curtains. Treat this as a loyalty market rather than a niche accommodation problem. One family recommends another, and they come back. _______________________________________________________________________________________________________________________________________ 📣 The AI Ambassador Program This episode is also brought to you in part by our AI Ambassador Program . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our AI Ambassador Program . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at VacationRentalFormula.com/AI Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/podcast/vrs680