Vacation Rental Success

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. Whether you're a property manager overwhelmed by AI options, or a team leader unsure how to get your staff onboard, this episode is packed with practical advice to help you start small, think big, and bring AI into your business in a human-centered, hospitality-first way. 📣 Midroll Sponsor: STRAIT Chat & the AI Ambassador Program This episode is brought to you in part by the STRAIT Chat Community - an exclusive space for short-term rental pros who want deeper conversations, smarter systems, and more collaborative learning. And 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/VRS635

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 direct booking is no longer an annual one-day event but a year-round strategy every host needs to embrace. From her humble beginnings managing a rental in the French Alps to launching one of the industry's most impactful virtual summits, Jenn shares her journey and the practical tactics that helped her (and now others) succeed. 📣 Midroll Sponsor: STRAIT Chat & the AI Ambassador Program This episode is brought to you in part by the STRAIT Chat Community - an exclusive space for short-term rental pros who want deeper conversations, smarter systems, and more collaborative learning. And 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/VRS634

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 drives guests to book directly - and it's not price or promotions. It's trust. Chris unpacks the real psychological barriers guests face when booking direct, and why removing uncertainty is the single most important thing you can do to boost conversions. Whether you're a solo host or managing hundreds of properties, building trust into every aspect of your brand is no longer optional - it's essential. 📣 Midroll Sponsor: STRAIT Chat & the AI Ambassador Program This episode is brought to you in part by the STRAIT Chat Community - an exclusive space for short-term rental pros who want deeper conversations, smarter systems, and more collaborative learning. And 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/VRS633

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 different from ChatGPT and other popular AI tools, and how vacation rental hosts and managers can use it to streamline operations, improve guest experience, and uncover hidden business insights. This isn't theory - it's a practical, passionate review of a platform Heather uses every day. Whether you're AI-curious or deep in the rabbit hole, you'll find useful takeaways to apply to your short-term rental business today. 📣 Midroll Sponsor: STRAIT Chat & the AI Ambassador Program This episode is brought to you in part by the STRAIT Chat Community - an exclusive space for short-term rental pros who want deeper conversations, smarter systems, and more collaborative learning. And 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/VRS632

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 like Airbnb, Vrbo, and Booking.com. Humphrey shares the powerful analogy behind digital sharecropping and breaks down what it really means to build a business you don't own. If you've ever questioned who really controls your guest relationships, your reviews, or even your ability to operate, this episode will hit home. From psychological burnout to platform dependency, from trust to true entrepreneurship, this is a conversation that every host and manager needs to hear. 📣 Midroll Sponsor: STRAIT Chat & the AI Ambassador Program This episode is brought to you in part by the STRAIT Chat Community - an exclusive space for short-term rental pros who want deeper conversations, smarter systems, and more collaborative learning. And 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/VRS631

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 importance of niche branding, trust-building, and the role of tech and website UX in conversion success. Heather also reflects on her own company's success - CottageLINK Rental Management, which achieved 85% direct bookings by the time it was sold in 2022. This episode is packed with practical tips, real-world insights, and a passionate discussion about the future of the vacation rental industry. 📣 Midroll Sponsor: STRAIT Chat & the AI Ambassador Program This episode is brought to you in part by the STRAIT Chat Community - an exclusive space for short-term rental pros who want deeper conversations, smarter systems, and more collaborative learning. And 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/VRS630

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 later co-founded Lake George Vacay, two short-term rental management companies that already stand out for their professionalism, creativity, and community connection. In our conversation, James shares how he went from working in marketing and real estate to building a growing business rooted in service, innovation, and unforgettable guest experiences (wait until you hear about the S'mores with Sasquatch and The Donut Wall! 📣 Midroll Sponsor: STRAIT Chat & the AI Ambassador Program This episode is brought to you in part by the STRAIT Chat Community - an exclusive space for short-term rental pros who want deeper conversations, smarter systems, and more collaborative learning. And 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/VRS629

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 of Hospitality Management: Why Local Wins and National Scale Fails." And when I say it's a must-read… I mean it. We talk in-depth about  the rise and fall of companies like Vacasa and Aimbridge, and what their journeys can teach us about sustainable growth and operational excellence in our own businesses. Ashley doesn't just point fingers - she outlines the five key pillars that support successful hospitality operations, no matter your size. If you're managing short-term rentals and thinking about how to grow without losing your sanity (or your staff), this one is absolutely packed with insights. 📣 Midroll Sponsor: STRAIT Chat & the AI Ambassador Program This episode is brought to you in part by the STRAIT Chat Community - an exclusive space for short-term rental pros who want deeper conversations, smarter systems, and more collaborative learning. And 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/VRS628

In this episode, Heather Bayer welcomes back a long-time friend and industry innovator, Bart Sobies, founder of iBooked.Online and the creative mind behind the Strive to Thrive events in Australia and beyond. Bart joins Heather (from tomorrow, no less - Australia time!) to share insights on: The power of in-person connections and how conferences can radically transform your business trajectory What's happening right now in the Australian short-term rental market Why AI isn't a trend - it's a revolution, and how it's already reshaping our industry How to avoid the "tool trap" with AI, and instead solve real problems with the right tech Building human-centered hospitality businesses that are scalable, sustainable, and future-ready Whether you're a seasoned manager or new to the STR space, Bart's global perspective and generous storytelling make this a must-listen. 📣 Midroll Sponsor: STRAIT Chat & the AI Ambassador Program This episode is brought to you in part by the STRAIT Chat Community - an exclusive space for short-term rental pros who want deeper conversations, smarter systems, and more collaborative learning. And 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/VRS627

What does it really mean to run a tech-enabled hospitality business - and how do we do it without losing the human touch? In this episode, Heather sits down with Jessica Gillingham, founder of Abode Worldwide and author of Tech-Enabled Hospitality, to talk about how property managers can embrace technology to improve guest experiences, operations, and brand storytelling. This is a conversation about more than tools - it's about mindset. From scaling sustainably to building trust in a digital world, Jessica brings clarity and compassion to a topic that often feels overwhelming. Whether you're a single host or managing hundreds of properties, there's something here for you. 📣 Midroll Sponsor: STRAIT Chat & the AI Ambassador Program This episode is brought to you in part by the STRAIT Chat Community - an exclusive space for short-term rental pros who want deeper conversations, smarter systems, and more collaborative learning. And 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/VRS626

In this solo episode, Heather Bayer returns to the mic for an approachable explanation of the transformative power of AI in short-term rental operations. With over 600 episodes under her belt, Heather has seen just about every trend in this space - but few as game-changing as this. Whether you're a solo host or run a multi-property management company, you've likely heard about ChatGPT, Claude, and AI tools - but how do you actually put them to work? This episode delivers five actionable ways to get started with AI right now, even if you're not a techie. It's practical, encouraging, and rooted in real use cases with everything from guest messaging to building your internal SOPs, and even creating your own AI team member. If you've been feeling overwhelmed by AI or unsure where to begin, this is your moment to step confidently into the future of STR operations. Revolutionize Your Employee Onboarding with THRIVE Essentials: Faster Training, Stronger Teams, Better Results! Discover how THRIVE Essentials accelerates onboarding for new property management staff, boosting performance and reducing turnover. >> THRIVE Essentials Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/VRS625

In this fun and super insightful episode, I'm joined once again by vacation rental marketing expert Jodi Bourne, and we're diving headfirst into something that's never been more important - your website. With all the recent changes to the big OTAs, more and more hosts are waking up to the power of direct bookings. And at the heart of that? Your website. It's not just a digital business card anymore - it's where your brand builds trust, tells your story, and convinces guests to book directly with you. Jodi and I chat about what makes a website truly work, from smart design choices and storytelling, to using AI, social proof, trust signals, and so much more. If you're ready to turn your website into a booking machine, this one's for you. Make sure you complete The Strategic AI Adoption Survey >>https://www.hostfully.com/survey You will get the chance to win an iPad and get access to '24 Use Cases For AI In Short-Term Rental Properties'. Revolutionize Your Employee Onboarding with THRIVE Essentials: Faster Training, Stronger Teams, Better Results! Discover how THRIVE Essentials accelerates onboarding for new property management staff, boosting performance and reducing turnover. >> THRIVE Essentials Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/VRS624

In this episode of the Vacation Rental Success Podcast, host Heather Bayer sits down for a summer Sunday chat with Justin Ford from Breezeway, to discuss how prioritizing safety can transform your short-term rental business.  Not just in protecting reputations, even boosting bookings, but in saving lives. Justin has been on the show just a few times over the years and his inspiring take on safety is a reflection of his two decades of experience in the industry.  For anyone not familiar with his booming voice and 6'5" stature, he  is a globally recognized vacation rental safety expert and Director of Safety & Certification Programs at Breezeway.  He delivers conference keynotes that will stay with you long after you leave the room, so if you ever get the opportunity to listen, don't miss it.   Recipient of the prestigious Shortyz Pioneer Award earlier this year (2025), he has become a pioneering voice in promoting practical, actionable safety standards for STR operators. From advising major companies like Casago/Vacasa, Moving Mountains, and the Naimon Group, to training hosts across the globe, Justin's passion for safety is saving lives and reshaping the way property managers think about hospitality. Make sure you complete The Strategic AI Adoption Survey >>https://www.hostfully.com/survey You will get the chance to win an iPad and get access to '24 Use Cases For AI In Short-Term Rental Properties'. Revolutionize Your Employee Onboarding with THRIVE Essentials: Faster Training, Stronger Teams, Better Results! Discover how THRIVE Essentials accelerates onboarding for new property management staff, boosting performance and reducing turnover. >> THRIVE Essentials Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/VRS623

When change hits fast and hard, what keeps a company grounded? In this episode, Heather welcomes Jackie Norde, who shares her remarkable journey from vacation rental software onboarding to her current role helping Casago franchisees succeed - especially in the wake of Casago's rapid expansion via Vacasa acquisitions. Jackie offers rich insights into hospitality, franchise onboarding, operational standards, and how a tiny orange booklet - the Casago ORANGE Standard - is transforming how vacation rental businesses deliver unforgettable guest experiences. Whether you're a property manager facing change, an owner scaling up, or just someone who believes hospitality should come from the heart, this episode delivers both inspiration and practical takeaways. Make sure you complete The Strategic AI Adoption Survey >>https://www.hostfully.com/survey You will get the chance to win an iPad and get access to '24 Use Cases For AI In Short-Term Rental Properties'. Revolutionize Your Employee Onboarding with THRIVE Essentials: Faster Training, Stronger Teams, Better Results! Discover how THRIVE Essentials accelerates onboarding for new property management staff, boosting performance and reducing turnover. >> THRIVE Essentials Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/VRS622

In this inspiring episode, Heather Bayer sits down with storyteller and copywriter Neely Khan to explore how hospitality businesses can set themselves apart through powerful, purpose-driven storytelling. Neely shares her journey from aspiring writer to founding AWC, a story-branding agency that helps short-term rental businesses create meaningful connections through every guest touchpoint. This episode is a must-listen for property managers and owners who want to stand out in a saturated market filled with AI-generated sameness. Make sure you complete The Strategic AI Adoption Survey >>https://www.hostfully.com/survey You will get the chance to win an iPad and get access to '24 Use Cases For AI In Short-Term Rental Properties'. Revolutionize Your Employee Onboarding with THRIVE Essentials: Faster Training, Stronger Teams, Better Results! Discover how THRIVE Essentials accelerates onboarding for new property management staff, boosting performance and reducing turnover. >> THRIVE Essentials Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/VRS621