Vacation Rental Success

Heather Bayer aka @CottageGuru
  • 4.7 (211)
  • Investing
  • Updated Weekly

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.

  1. 21h ago

    VRS667 - Two Ways to Make More Money This Year: Private Chef Upsells and Smarter AI Use

    This Episode is Sponsored by Lodgify If you have been thinking about building your own direct booking channel and reducing your reliance on the OTAs, Lodgify is worth a serious look. It brings your booking website, channel management, guest messaging, and unified inbox into one place. VRS listeners can get 20% off yearly and bi-yearly plans with code VRS-20, valid through to the end of June. Visit Lodgify and use code VRS-20 to get started.  > Click here to visit Lodgify.com _________________________________________________________________________________________ Siddhi Mittal has one of those backgrounds that makes you wonder how a single person contains all of it. She grew up in Agra, studied computer science and AI at Columbia, landed on an asset-backed mortgage securities trading floor in New York, moved to London, spent six years in finance, had a full-blown existential crisis, quit to build a startup, stumbled into the vacation rental industry almost by accident, had a baby, got lost down an AI rabbit hole, nearly derailed her marriage, and is now running two businesses while teaching women worldwide how to use AI to earn more and work less. And it seems like all that happened without her taking a breath! Yhangry is a private chef booking platform she co-founded in the UK. It started as a consumer product for anyone who wanted a chef to cook at home. Then Siddhi discovered that 50% of her users were vacation rental guests and property managers, and everything changed. Yhangry is now one of the most interesting upsell opportunities in the STR space: property managers can generate a simple affiliate link, share it with guests, and earn commission whenever a chef is booked. No operational overhead. No coordination. The platform handles everything from booking to payment to quality assurance. The conversation covers all of that, and then it goes somewhere else entirely. Because Siddhi is also the founder of SheCompoundsAI, a live AI education event series focused on helping women build practical AI skills. She brings the same direct, jargon-free energy she uses on stage to this conversation, and what comes out is one of the most accessible explanations of prompting, agents, and reverse prompting I have heard anywhere. If you have been hovering at the edge of AI adoption and not quite sure how to get started, this episode gives you the simplest possible on-ramp. And if you are a property manager looking for a genuinely low-effort upsell revenue stream, the Yhangry conversation is worth your attention. ________________________________________________________________________________________________________________________________________ 📣 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/VRS667

    57 min

  2. Jun 3

    VRS666 - The Seven Deadly Sins of AI in Your STR Business

    This Episode is Sponsored by Lodgify If you have been thinking about building your own direct booking channel and reducing your reliance on the OTAs, Lodgify is worth a serious look. It brings your booking website, channel management, guest messaging, and unified inbox into one place. VRS listeners can get 60% off yearly and bi-yearly plans with code VRS-60, valid through June 9th and 20% off yearly and bi-yearly plans with code VRS-20, valid through June 10 to end of June. Visit Lodgify and use code VRS-60 to get started.  > Click here to visit Lodgify.com _________________________________________________________________________________________ Episode VRS666 arrives with purpose. Rather than sidestepping the number, Heather uses it as a frame for something worth naming: the very human patterns that undermine AI adoption in short-term rental businesses. Drawing on her own experience, conversations with property managers, and the collected wisdom of fifty experienced operators featured in Brooke Pfautz's book Vacation Rental Secrets, she maps seven recognisable failure modes onto the classical seven deadly sins. These are not abstract warnings. They are patterns that show up with remarkable consistency across different markets, business sizes, and experience levels. Heather has lived several of them herself. And because they are patterns, they can be recognised, named, and redirected. That is the point of the episode: awareness is the first step toward a different choice. If you have been accumulating AI tools without connecting them, automating your guest communications without thinking about what that does to the relationship, or chasing the latest model release without going deep into the one you already have, this episode is for you. And if you recognise yourself in any of the seven sins, Heather's message is not judgment. It is: now you can make a different choice. ________________________________________________________________________________________________________________________________________ 📣 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/VRS666

    44 min

  3. May 27

    VRS665 - Bionic Not Robotic: Steve Schwab on AI, Integration, and Community

    This Episode is Sponsored by Lodgify If you have been thinking about building your own direct booking channel and reducing your reliance on the OTAs, Lodgify is worth a serious look. It brings your booking website, channel management, guest messaging, and unified inbox into one place. VRS listeners can get 60% off yearly and bi-yearly plans with code VRS-60, valid through June 9th and 20% off yearly and bi-yearly plans with code VRS-20, valid through June 10 to end of June. Visit Lodgify and use code VRS-60 to get started.  > Click here to visit Lodgify.com _________________________________________________________________________________________ A year ago, Steve Schwab closed one of the most talked-about deals in the short-term rental industry - the acquisition of Vacasa by Casago. At the time, he described it as surreal and exciting. A year on, the headline has given way to the hard work: integrating systems, transitioning markets, reshaping a culture, and doing all of it while holding onto the belief that this is, at its core, a relationship business. In this conversation, Heather catches up with Steve to take stock of that year - what has worked, what has been harder than anticipated, and what the ongoing Casago-Vacasa integration has taught him about leadership at scale. They also get into AI: how Steve is approaching it inside a franchise organisation that spans everything from small, locally owned operations to private equity-backed enterprises, why he talks about making Casago bionic rather than robotic, and the very real challenge of bringing people along when the pace of change is so fast that even the most enthusiastic adopters are missing fundamentals. The episode closes with something genuinely new for the industry: a free, community-based AI learning network on Circle, built for STR professionals at every level of familiarity with AI. Steve and Heather are both actively involved, and this conversation is part of the launch. If you have been curious about AI but not sure where to start, or looking for a place to ask questions without feeling foolish, this community is worth knowing about.  ________________________________________________________________________________________________________________________________________ 📣 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/VRS665

    54 min

  4. May 20

    VRS664 - Building Two Businesses With a Small Team and a Smart AI Habit

    This Episode is Sponsored by Lodgify If you have been thinking about building your own direct booking channel and reducing your reliance on the OTAs, Lodgify is worth a serious look. It brings your booking website, channel management, guest messaging, and unified inbox into one place. VRS listeners can get 60% off yearly and bi-yearly plans with code VRS-60, valid through June 30th. Visit Lodify and use code VRS-60 to get started.  > Click here to visit Lodgify.com ________________________________________________________________________________________ It has been over two years since Kerri Gibson was last on the show, and a great deal has changed. The Chalets Hygge brand has expanded into Experience Hygge, an umbrella that now also covers a roadside motel four hours away from the original property. It is a seventeen-room hospitality business with daily turnover, walk-in guests, and an operational rhythm that has almost nothing in common with the chalets that built the brand. Kerri and her partner Philippe Pichette took on the motel in 2024 and have spent the past seventeen months renovating it while keeping it operational. In this conversation, Kerri talks honestly about what running two very different businesses with a small team actually looks like, how she has stepped back to let her chalet team grow into their roles, and where AI has earned a permanent place in her week. She also speaks plainly about her seven-year history with Lodgify, her direct booking strategy across both businesses, and the move she has been quietly making from ChatGPT to Claude. There is something here for anyone running a lean hospitality business who is curious about AI but does not want hype.  ________________________________________________________________________________________________________________________________________ 📣 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/VRS664

    53 min

  5. May 13

    VRS663 - Building the Foundations Before the AI Storm Hits

    This episode is sponsored by Lodgify, the all-in-one vaction rental platform that will help you start, manage and grow your short-term rental business. You get your own professional booking website. A channel manager that keeps Airbnb, Vrbo and Booking.com, all in sync. Automated guest messaging and a unified inbox so you're not bouncing between six different apps, whether you've got one property or more. It makes running your business a great deal cleaner, and right now through June 30th, you can get 20% off with code VRS20 on all their yearly and bi-yearly Ultimate and Professional plans.  > Click here to visit Lodgify.com _______________________________________________________________________________________________________________________________________ In August 1992, Hurricane Andrew tore through South Florida and damaged or destroyed more than 125,000 buildings. When investigators went through the wreckage, they found that the worst destruction wasn't always explained by the strength of the storm. It was traced to something far more mundane: the connectors, the joints, the foundations. The hardware that held the structure together when the pressure arrived. Out of that came the Miami-Dade construction standards, some of the most rigorous building codes in the United States. Heather opens this solo episode with that story for a reason. After spending months speaking at industry events, running the AI Ambassador Programme, and watching property managers at every scale wrestle with AI adoption, she sees the same pattern: businesses are buying tools without building the foundations that determine whether those tools will hold up. The AI storm is already here. The question is what your connectors look like. This episode is a candid, honest look at why the AI gap in short-term rentals is getting wider, where people are actually learning about AI and what each source is good for, why team learning matters more than individual effort, and a simple three-question filter for evaluating any new AI tool. It also includes a practical foundation idea borrowed from Will Guidara's Eleven Madison Park, and a story about an operator who finally got moving when she stopped trying to learn more and started building one small thing.  ________________________________________________________________________________________________________________________________________ 📣 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/VRS663

    44 min

  6. May 6

    VRS662 - The Guests You Don't See Coming

    This episode is sponsored by Lodgify, the all-in-one vaction rental platform that will help you start, manage and grow your short-term rental business. You get your own professional booking website. A channel manager that keeps Airbnb, Vrbo and Booking.com, all in sync. Automated guest messaging and a unified inbox so you're not bouncing between six different apps, whether you've got one property or more. It makes running your business a great deal cleaner, and right now through June 30th, you can get 20% off with code VRS20 on all their yearly and bi-yearly Ultimate and Professional plans.  > Click here to visit Lodgify.com _______________________________________________________________________________________________________________________________________ This episode started with an observation Heather made on LinkedIn - a post from Ela Mezhiborsky about her company's annual self-care day - and grew into a conversation that cuts to the heart of something most operators get wrong when they bring AI into their businesses. Ela is co-founder and president of AutoHost, an AI-powered guest screening and identity verification platform used by property managers around the world. But she came to it the same way most VRS listeners came to their businesses: through hands-on operation. Before AutoHost existed, she was running Quick Stay, a Toronto-based property management company that grew to over 100 properties. The tool was built because she was the operator who needed it. The conversation opens with a real incident - a Christmas 2016 call from Toronto police about a known gang member, which revealed months of undetected criminal activity running through Quick Stay's properties. That story explains why AutoHost exists, and it also explains Ela's unusually clear-eyed view of where human judgment fails and where systematic screening has to take over. But the episode is as much about people as it is about technology. Ela runs an AI-first company and is visibly thoughtful about what that means for the humans inside it. She talks about what happens to a team when AI arrives - the anxiety before the relief - and what operators can do to manage that transition honestly. The annual self-care day, which honours Ela's late husband and co-founder, Anton Silberberg, is part of that story too. By the end, the episode covers AI-powered fraud: synthetic identities, voice cloning, and why gut instinct is no longer a reliable defence. If you've been thinking about guest screening as a nice-to-have, Ela makes a case that identity verification is now table stakes - not because fraud is new, but because AI has made it dramatically cheaper, faster, and harder to detect. ________________________________________________________________________________________________________________________________________ 📣 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/VRS662

    49 min

  7. Apr 29

    VRS661 - The Year He Stopped Growing and Built Something Better

    This episode is sponsored by Lodgify, the all-in-one vaction rental platform that will help you start, manage and grow your short-term rental business. You get your own professional booking website. A channel manager that keeps Airbnb, Vrbo and Booking.com, all in sync. Automated guest messaging and a unified inbox so you're not bouncing between six different apps, whether you've got one property or more. It makes running your business a great deal cleaner, and right now through April 30th, you can get 60% off with code VRS60 on all their yearly and bi-yearly Ultimate and Professional plans.  > Click here to visit Lodgify.com _______________________________________________________________________________________________________________________________________ A lot of property managers feel the pressure to do something with AI, but struggle to articulate what an AI agent actually is, or how one would function inside a real business. This conversation with Alex Zemianek goes straight at that gap. Alex is the CEO and founder of JZ Vacation Rentals in St. Louis, a dual-model business running about 70 fully managed properties alongside a curated luxury OTA representing close to 2,000 properties across 14 states and three countries. He is not a technical operator. He came up through sales and leadership, not software. And that is precisely what makes his experience with AI worth paying attention to. Alex spent most of 2024 building what he calls his internal AI, deliberately pulling focus away from adding properties and concentrating instead on organizing his systems, cleaning up his data, and building agents that could work across his business. The result was a 168% improvement in his bottom line without adding a single property. The episode covers what that actually looked like in practice: how he thinks about prompting, how he defines agents for a non-technical audience, what his CEO assistant agent does every morning, and why organizing your data is not a nice-to-have but the foundation everything else depends on. This is one of those conversations that gives listeners both the clarity and the confidence to stop waiting and start doing. Alex offers a rare combination: operational credibility, genuine enthusiasm, and the kind of plain-language explanations that make AI accessible without making it feel trivial. ________________________________________________________________________________________________________________________________________ 📣 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/VRS661

    58 min

  8. Apr 22

    VRS660 - Values First: Why What You Stand For Shapes Everything AI Does Next

    This episode is sponsored by Lodgify, the all-in-one vaction rental platform that will help you start, manage and grow your short-term rental business. You get your own professional booking website. A channel manager that keeps Airbnb, Vrbo and Booking.com, all in sync. Automated guest messaging and a unified inbox so you're not bouncing between six different apps, whether you've got one property or more. It makes running your business a great deal cleaner, and right now through April 30th, you can get 60% off with code VRS60 on all their yearly and bi-yearly Ultimate and Professional plans.  > Click here to visit Lodgify.com _______________________________________________________________________________________________________________________________________ This episode began somewhere else entirely. A few weeks ago, Heather appeared as a guest on The Art of Hospitality Podcast, hosted by Adam Norko and Conrad O'Connell, expecting to talk about AI. They ended up talking about values. That conversation planted a question Heather has been sitting with ever since: if you train an AI on your processes without first being clear on what your business actually stands for, are you just automating the wrong thing, faster? Adam returns to the show for a third time to help answer that question. He is the founder of VR Growth, a consultancy working with vacation rental and PropTech companies, and someone who has seen this industry from multiple angles - as a marketing director for a large management company, a vendor-side executive at Point Central and Breezeway, a Chief Growth Officer, and now an independent consultant. He is also, by his own admission, a small Airbnb host on the Outer Banks, running five properties with his wife. The conversation moves through the gap between values written on a wall and values that actually show up in daily decisions, the leadership behaviours that make the difference, how AI can help operators discover and articulate what they genuinely believe in, and Adam's emerging thinking about self-selected communities of like-minded operators as the industry's next meaningful structural development. The through-line is clear: values have to come before systems, and community has to come before scale. ________________________________________________________________________________________________________________________________________ 📣 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/VRS660

    54 min
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4.7
out of 5
211 Ratings

About

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.

Information

  • Creator
    Heather Bayer aka @CottageGuru
  • Years Active
    2013 - 2026
  • Episodes
    668
  • Rating
    Clean
  • Copyright
    © MOSO Partnership Inc.
  • Show Website
    Vacation Rental Success

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