Vacation Rental Success

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

In this episode, Heather Bayer sits down with Heather Fillmore, co-founder of Utah-based StayLuxe Properties, for an honest and inspiring conversation about resilience, growth, and leadership in the short-term rental space. Heather shares her remarkable journey from surviving a catastrophic flood in Baton Rouge to launching a successful luxury vacation rental brand in Park City, Utah - right in the middle of the COVID pandemic. 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/VRS620

In this episode of the Vacation Rental Success Podcast, host Heather Bayer sits down with Fred Bassili from Hostfully to discuss the evolving role of AI in vacation rental businesses and how short-term rental managers can use AI tools and workflows to scale operations, improve guest communication, and boost owner acquisition. Fred Bassili, a seasoned content and marketing strategist at Hostfully, brings a wealth of experience from both sides of the vacation rental industry - as a former host and now a driving force behind tech adoption and education. With a background in content development and a passion for simplifying complex technologies, Fred is on a mission to help property managers use AI in practical, hospitality-centered ways. His insights come not only from his work at Hostfully, but from years of observing the shift in industry sophistication and tech stack growth among property managers worldwide. 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/VRS619

Some of the strongest brands in the vacation rental business have been around for decades and are rooted in tradition, family values and local knowledge. As the next generation stepping into a decades-old family-run vacation rental business, Alexis Miller personifies this legacy as she shares how she's honoring her family’s rich story while ushering in thoughtful innovations to meet today’s fast-paced demands. Cottage Connection of Maine was founded in 1992 by Jeff Miller and Audrey Leeds-Miller, and 33 years later is still going strong. It’s a lean organisation operationally managed by their daughter Alexis, a graduate of an International business program. Heather and Alexis connected at the VRNation Conference in Austin - over Yorkshire tea bags and a moment of true hospitality. That spirit flows through this episode as Lexi opens up about her journey from her childhood in the business and housekeeping to officially joining the business full-time after college. 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/VRS618

In this episode of the Vacation Rental Success Podcast, host Heather Bayer shares her top takeaways from the AI for Business Summit in Orlando, diving into the transformative power of artificial intelligence and how vacation rental professionals can leverage it to drive growth, efficiency, and guest experience 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/VRS617

In this episode of the Vacation Rental Success Podcast, host Heather Bayer sits down with… herself! It’s a podcast within a podcast as Heather explores the power of AI through a hands-on demonstration of Google's NotebookLM, sharing practical examples of how it can be a game-changer for short-term rental businesses. Drawing on her extensive industry experience and recent immersion in AI tools, Heather shares insights into how vacation rental operators can use AI not only to save time and money, but also to transform their business operations. Through a live example of AI-generated podcast content, she showcases how the future of AI isn't something to fear - but a tool to empower. 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/VRS616

In this no-holds-barred conversation, Heather is joined by longtime friend of the show, Mark Simpson, to unpack the buzz - and backlash - surrounding Airbnb’s newly launched "Services" offering. From liability concerns to insurance gaps, Mark breaks down why this move is raising eyebrows in the host community and what you can do right now to protect your business. Then, we switch gears and dive headfirst into the world of AI in vacation rentals. Mark shares how he’s been helping hosts build custom GPTs, boost productivity, and take back control of their marketing strategies. If you're curious about how to harness AI without feeling overwhelmed, this episode delivers a masterclass in cutting through the fluff and getting to what works. 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/VRS615

In this insightful conversation, I welcome back digital marketing expert Conrad O’Connell, founder of BuildUp Bookings, to talk about the dramatic shifts in how people are finding, booking, and experiencing vacation rentals. It’s been nearly a decade since our first conversation, and we’ve both been on quite the journey -personally and professionally. Conrad shares what’s changed (including growing his family and his business) and what’s stayed consistent in the ever-evolving digital landscape. We talk about how Google’s AI-powered search is impacting SEO, how paid ads are gaining traction again, and what content strategies still work in 2025. If you’ve ever felt confused about where to put your marketing dollars - or how to write content that still gets found - this episode is packed with clarity. 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/VRS614

In this episode of the Vacation Rental Success Podcast, host Heather Bayer sits down with her son and business partner, Mike Bayer, to discuss the essential role of an "AI Ambassador" in vacation rental businesses. Together, they explore why nominating a dedicated AI advocate can unlock efficiencies, reduce burnout, and help teams fully embrace the transformative potential of artificial intelligence. In this conversation Heather and Mike talk about why companies must move from passive awareness to active implementation. The best way to do this is to empower someone within their business to lead the AI charge and they explain the steps to get this underway. 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/VRS613

This week on the Vacation Rental Success Podcast, Heather reconnects with long-time friend and returning guest, Lorraine Woodward, the unstoppable force behind Becoming rentABLE. Lorraine has been championing accessibility in the short-term rental industry for years, and this time, she’s back with big news - an exciting new partnership with Expedia Group through their Open World Accelerator Program. Together, Heather and Lorraine dive into what accessibility really means today (spoiler alert: it’s not just ramps and wide doors), and how simple, low-cost features like under-counter lighting, secondary locks, and hard surface driveways can dramatically open your property to a broader guest base - including families with children, seniors, people recovering from surgery, and neurodivergent travelers. Lorraine also shares her personal journey, building an inclusive rental to meet her family's needs, and the lightbulb moment that sparked the idea for a global platform. Her story is as inspiring as it is actionable. This is a must-listen if you've ever thought, "Accessibility isn't for my market." Think again - Lorraine shows us why accessible design is not only the right thing to do, it's really good business. 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/VRS612

In this special replay episode in our Leadership Series, Heather reconnects with Rachel Alday, founder of Abode Luxury Rentals, for a powerful conversation on building a thriving business through intentional leadership and company culture. Rachel shares the real story behind how she and her husband grew their boutique vacation rental company from a few properties to a high-performing, values-driven team of nearly 60 people across three markets. What started as a “mom-and-pop” business became a case study in leadership - rooted in authenticity, driven by values, and centered around a deep commitment to both team and guest experience. Whether you’re managing five properties or five hundred, this episode offers practical insights on how to lead with purpose, build loyalty from the inside out, and create a culture that sustains long-term growth and excellence. 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/VRS611

In this landmark episode of the Vacation Rental Success Podcast, Heather Bayer is joined by Steve Schwab, the Founder and CEO of Casago, at a truly pivotal moment - not just in his personal journey, but in the history of the vacation rental industry. As Casago steps into a groundbreaking merger with Vacasa, Steve reflects on the path that led him here and the deeply held leadership values that have shaped the company’s evolution. From climbing rooftops in Rocky Point, Mexico, to becoming the driving force behind a national franchise brand, Steve’s story is anything but typical. In this conversation, he opens up about the early moments that launched his career, the foundation of the ORANGE Credo that anchors Casago’s culture, and what it means to scale a values-based business without losing its soul - especially in the wake of one of the industry’s biggest mergers to date. If you’re thinking about growth, culture, or the future of professional property management, this episode delivers both heart and strategy in equal measure. 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/VRS610