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Vacation Rental Success

Heather Bayer aka @CottageGuru

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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, a ...
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The short-term rental industry is evolving fast, and Simon Lehmann isn’t afraid to say what others won’t. STR Global Unlocked is where property managers, STR tech founders, vacation rental investors, and hospitality leaders get real about the business. Each episode breaks down what’s working, what’s broken, and what’s coming next: property management operations, direct bookings, vacation rental software, pricing strategies, mergers and acquisitions in real estate, professional host challenge ...
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A slow learner, one who just got by in high school and university, it took a long time to discover the most important rule……”The Numbers Never Lie”. After 5 years of advertising, I crossed over to Marketing, where accountability and experience resulted in amassing significant successes (including the introduction of a $100 million business in North America). It was the thrill of the chase and being hands-on, I enjoyed doing the doing and encouraging the people I worked with to tell me what t ...
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It's the first episode of 2026 - and that means it's time for our annual deep dive into what's happened across the vacation rental industry over the past year, and what's coming next. Back by popular demand, David Angotti joins Heather to break down the big shifts of 2025 and share what smart property managers should focus on heading into the New Y…
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“2025 wasn’t about growth at all costs. It was about margins, execution, and whether your operation actually works.” — Simon Lehmann 2025 marked a turning point for the short-term rental industry. Not a year of hype or breakout growth, but a year of recalibration. In this Holiday Special of STR Global Unlocked, Simon Lehmann reflects on the convers…
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What if artificial intelligence could actually enhance the human touch instead of replacing it? In this episode, Heather speaks with Eliseo Palous, co-founder of Short Stay Media, to explore how AI - especially voice AI - is revolutionizing guest communications in the short-term rental industry without sacrificing what matters most: hospitality, re…
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Europe is often discussed as a single market. This panel makes clear why it is not. In this panel, Simon Lehmann brings together three leaders navigating growth across Europe’s most fragmented markets: Alexander Limpert (GuestReady and RentalReady), Antoine Serrurier (COCOONR), and Harold Lubberdink (Happy.Rentals). Together they break down what su…
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What happens when a corporate professional takes a chance on short-term rentals in the middle of a global pandemic? In this inspiring episode, Heather sits down with Stacey St. John - real estate investor, property manager, and community builder - to unpack her incredible journey from cautious investor to powerhouse property manager with a portfoli…
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Woody Marshall is a General Partner at TCV, one of the most influential investment firms in global technology and a long-standing backer of travel companies including Expedia, Airbnb, HomeAway and TripAdvisor. With more than two decades of experience investing in category-defining platforms, Woody brings a unique view of how technology evolves and …
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In this episode of The Business Method Podcast, host Chris Reynolds sits down with Uri Levine, the co-founder of Waze, a GPS navigation app acquired by Google for $1.1 billion, and Move It, a public transit app acquired by Intel for just shy of $1 billion. Uri shares invaluable insights on the rollercoaster journey of entrepreneurship, emphasizing …
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When disaster strikes - whether it's a fire, flood, or even a bat infestation - families are often left scrambling for safe, comfortable housing. That's where Jake Mast steps in. In this episode, Heather Bayer sits down with Jake, founder of Rapid Response AI Housing, to explore how his company is disrupting the traditional insurance housing model …
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Cami Narino, Chief Operating Officer, and Jeff Hurst, Chief Executive Officer at Furnished Finder, join Simon Lehmann to analyze one of the most important shifts happening in housing and hospitality today: the rise of midterm rentals. Over the past decade, Furnished Finder has grown from zero to more than 300,000 listings, powered by independent la…
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📌In this power-packed episode, Heather Bayer is joined once again by vacation rental marketing guru Mark Simpson of Boostly. Mark returns for his fifth appearance on the podcast - and this time, he's bringing an urgent message for vacation rental professionals across North America: The FIFA World Cup 2026 doesn't start in June... it starts on Decem…
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Glenn Fogel is the President and CEO of Booking Holdings, the parent company of Booking.com, Priceline, Kayak and other global brands that shape how the world travels. With more than two decades at the forefront of online travel, he has guided Booking through major industry shifts, emerging technologies and changing traveler behavior. In this episo…
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This week I'm welcoming back one of my favourite guests, Neely Khan, founder of the storytelling agency Artwork Creative. This is her second time joining me in less than six months - and there's a good reason for that. Neely is at the forefront of one of the most important shifts we're seeing in vacation rental marketing: the rise of AI-powered sea…
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Sean Breuner is the Founder and CEO of AvantStay, one of the most ambitious hospitality brands in the short-term rental industry. Since launching in 2017, AvantStay has raised significant capital, expanded across the United States, and set out to define what a national hospitality brand could look like in STR. In this episode, Simon Lehmann sits do…
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In this episode, Heather sits down with Dr. Rachel Gainsbrugh from Short Term Gems to explore how artificial intelligence is changing the way short-term rental businesses operate. Rachel shares how she moved from being a pharmacist to building a real estate education company focused on medical professionals, and how AI is now a core part of that mi…
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Cliff Johnson is the former Co-Founder of Vacasa, one of the largest short-term rental management companies in the United States, and now serves as President of PadSplit, a fast-growing affordable housing marketplace. His journey from startup founder to industry veteran gives him a rare perspective on how far the STR sector has come (and what still…
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In this packed episode, Heather Bayer shares her biggest takeaways from the AI for Business Summit in Las Vegas - and how short-term rental hosts and property managers can take immediate, practical steps to adopt AI tools in their business. Heather reveals how she used a Plaud NotePin to record and summarize every session, giving her powerful insig…
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Two systems drive every property management company: revenue and operations. For years, they’ve worked in silos. But what happens when they finally connect? In this episode, Simon Lehmann brings together Jeremy Gall, Founder and CEO at Breezeway, and Richie Khandelwal, Co-founder at PriceLabs, to explore how smarter data, clearer demand signals, an…
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Dennis Goedheid is back on the show, and we dive deep into one of the most overlooked yet mission-critical aspects of running a property management company - identifying and saying no to the wrong owners. We also chat about his journey with Casiola's international expansion, his team's DEI award win at VRMA, and why scaling means getting crystal cl…
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Amiad Soto is the co-founder and CEO of Guesty, one of the most recognized property management software platforms in the short-term rental industry. His journey started in Tel Aviv, where he and his brother Koby launched the company more than a decade ago, before taking it through Y Combinator in Silicon Valley. Under his leadership, Guesty has gro…
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While everyone's been playing around with AI tools like ChatGPT, few in the short-term rental industry have taken the next step - turning experimentation into strategy. In this episode, Heather shares a clear, step-by-step framework to help you move from random tinkering to thoughtful implementation, drawn straight from her AI Ambassador Program. W…
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Carl Shepherd is the Co-Founder of HomeAway, the marketplace that helped define the modern short-term rental industry. Before Airbnb became a household name, Carl and his co-founder Brian Sharples built HomeAway into a global platform that changed how people rent and manage vacation homes. The company went public in 2011 and was later acquired by E…
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In this episode, I'm joined by the brilliant Jenn Boyles, founder of the Direct Booking Success Summit and host of the Direct Booking Success Podcast. Jenn is a passionate advocate for empowering hosts and property managers to take back control from the OTAs - and she did it herself with an incredible 80% direct booking rate. We go deep into why di…
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Every major player in short-term rentals has chased the idea of building a truly global operator. None have cracked it. In this panel, Simon Lehmann brings together three leaders shaping the next phase of professionalization: Graham Donoghue (Forge Group, UK), Steve Schwab (Casago, US), and Quirin Schwaighofer (MadeComfy, Australia). Together they …
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In this episode of The Business Method Podcast, host Chris Reynolds sits down with legendary venture capitalist Tim Draper — the man behind early investments in Tesla, SpaceX, Hotmail, Skype, and Bitcoin. Tim shares how his bold approach to risk, belief in innovation, and commitment to empowering people have shaped a new generation of entrepreneurs…
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In this penultimate episode in our series on Direct Booking, this is an episode you can't afford to miss. Heather is joined by long-time industry leader Chris Maughan, the founder of i-PRAC and a pioneer in the trust movement for short-term rentals. This conversation isn't about OTAs, algorithms, or the latest booking engine. It's about what really…
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Brian Egan is the Co-Founder and CEO of Evolve, a Denver-based hospitality company with a mission to become the most trusted brand in vacation rental. Since launching Evolve in 2011 alongside Adam Sherry, Brian has grown the company to support over 35,000 properties and more than $5 billion in rental revenue. If you're navigating the complexities o…
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In this solo episode, Heather shares her enthusiasm for Google's NotebookLM. If you've ever wished for a research assistant who knows your business inside and out - an assistant who can analyze guest reviews, SOPs, market data, and spit out insights without hallucinating - this one's for you. Heather walks through how NotebookLM works, why it's dif…
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“Short-term rental is mainstream hospitality. It makes up 14% of global hospitality. And mainstream industries must operate by a different set of rules.” — Simon Lehmann The short-term rental industry is at a turning point. Regulation is tightening, OTAs are shifting power, and owners are demanding more transparency. Technology and AI promise effic…
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STR Global Unlocked is the podcast built to say what others won’t. Hosted by Simon Lehmann, one of the most trusted voices in the global STR space, every episode takes on the hard questions shaping property management, STR tech, investment, and hospitality such as: Is regulation now existential for STR? Are OTAs making operators fragile? Will short…
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In this bold and thought-provoking episode, Heather sits down with Humphrey Bowles, the founder of Truvi and who has adopted the term "digital sharecropping" within the short-term rental industry. Together, they explore the illusion of entrepreneurship in the short-term rental world - especially when you build your business entirely on platforms li…
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In this first episode of a special 5-part series on direct booking, Heather Bayer sits down with Louis Andrews, Director at OVO Network, to explore what it really takes to win the battle against OTAs and build a successful direct booking strategy. With OVO Network reaching 75-80% direct bookings, Louis shares the secrets behind their platform, the …
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I first met James Rubino at a VRMA conference in Orlando two years ago. He was there at the start of his journey in short term rentals, to learn and network and I mentioned to him then I would have him as a guest on the podcast down the road. So two years later here we are and what a story it is . At just 26, James launched Rubino Home Ventures and…
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Have you ever found yourself wondering why so many large-scale property management companies rise quickly… and then fall just as fast? In this episode, I'm joined by Ashley Ching, Founder and CEO of Inhaven, who brings a fresh - and deeply researched - perspective to this question. Ashley recently published an eye-opening report, "A 25-Year History…
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