VRS628 - Why Local Wins: The Five Pillars for Success You Must Follow - with Ashley Ching
Release Date: 09/10/2025
VRS638 - Democratizing Genius: How Dr. Rachel Gainsbrugh Uses AI to Supercharge Short-Term Rental Success
Vacation Rental Success
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 more done with less effort, speed up onboarding, reduce mistakes, and support team members in delivering better guest experiences. Rachel gives examples from her work building hundreds of GPTs, creating...
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VRS637 - AI in Action: What STR Hosts Can Learn from the AI for Business Summit
Vacation Rental Success
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, direct-response video, personal branding, and more. If you're ready to get ahead of the curve and use AI to save time, elevate guest experiences, and stand out in a competitive market, this is a...
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VRS636 - Scaling Smart: How to Spot the Owners Who’ll Sabotage Your Growth
Vacation Rental Success
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 just starting out or managing hundreds of properties, this conversation is packed with real-world insights from someone who’s learned the hard lessons - and is still smiling! 📣 Midroll Sponsor:...
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VRS635 - From Tinkering to Transformation: Building an AI Adoption Strategy for Your Vacation Rental Business
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 . 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...
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VRS634 - The Direct Booking Mindset Shift: What Every Host Needs to Hear Right Now
Vacation Rental Success
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...
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VRS633 - The Trustology: The Secret to a Successful Direct Booking Strategy with Chris Maughan
Vacation Rental Success
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...
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VRS632 - How to Transform Your Short Term Rental Business with Google’s NotebookLM
Vacation Rental Success
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...
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VRS631 - Are You a Digital Sharecropper? Taking Back Control with Humphrey Bowles
Vacation Rental Success
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,...
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VRS630 - Build Trust, Book Direct: Lessons from Louis Andrews of OVO Network
Vacation Rental Success
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...
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VRS629 - From Digital Guides to Donut Walls: Inside a Next-Gen Guest Experience
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...
info_outlineHave 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