Vacation Rental Success

In this solo episode Heather Bayer continues the series on training and development in the short-term rental space.  Drawing on her past as a training consultant and her years of managing hundreds of properties, Heather shares a clear, practical path to building team training that works - even if you're not a "trainer." She also introduces an incredible AI tool - NotebookLM - that can help you des...

In this episode, Heather Bayer welcomes back her son and business partner, Mike Bayer, for a timely New Year's discussion on a topic that affects nearly every property manager: onboarding and training. After a holiday season filled with family chaos (a trip to the emergency room, and a broken hot tub!), Heather and Mike shift gears to reflect on the challenges of integrating new team members into...

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 Year. From PMS shakeups and AI integration to a ren...

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, responsibility, and trust. Eliseo shares the fascina...

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 portfolio of beachfront properties in Myrtle Beach. Stacey...

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 by combining speed, accuracy, and human-centered A...

📌 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 December 5, 2025. That's the date the match draws are...

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 search. If you're still trying to wrap your head arou...

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 mission. They discuss how AI is helping hosts get mo...

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 insights on AI avatars, automated guest journeys, direc...

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 clear on your homeowner criteria. Whether you're jus...

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 A...

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...

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 pri...

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, an...

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...

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...

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-t...

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 Na...

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 Wh...

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 abo...

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...

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 anymor...

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...

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 s...