Vacation Rental Success
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, and Chex TV and is frequently interviewed on real estate and travel topics by magazines and daily newspapers.
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VRS647 - The Missing Piece in STR Training: Why Soft Skills Matter More Than Ever - with Ali Cammelletti
01/21/2026
VRS647 - The Missing Piece in STR Training: Why Soft Skills Matter More Than Ever - with Ali Cammelletti
In this episode, Heather sits down with returning guest Ali Cammelletti, a hospitality consultant, speaker, and the founder of Spark Your Mindset. With more than 30 years of experience in hospitality, Ali brings powerful insights into how soft skills - like empathy, emotional intelligence, and communication - can make or break a vacation rental business. While software training and hard skills often dominate onboarding and development, Ali makes the case for why soft skills are just as essential across every role in a short-term rental company - from the cleaners to the C-suite. Whether you’re leading a remote team, onboarding new hires, or managing a growing portfolio, you’ll walk away from this episode with a deeper understanding of where emotional intelligence fits in, how to recognize soft skill gaps, and practical ways to start coaching your team - even if you’ve never thought of yourself as a coach. ________________________________________________________________________________________________________ 📣 Midroll Sponsor: STRAIT Chat & the AI Ambassador Program This episode is brought to you in part by the - 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 . 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 Are you listening to this podcast on the move? Get to the show notes here:
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VRS646 - NotebookLM & the New Age of STR Team Training
01/14/2026
VRS646 - NotebookLM & the New Age of STR Team Training
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 design and deliver onboarding, checklists, and micro-trainings using content you already have. If you’re short on time, resources, or tech confidence, this episode will give you the roadmap to train smarter, not harder. ________________________________________________________________________________________________________ 📣 Midroll Sponsor: STRAIT Chat & the AI Ambassador Program This episode is brought to you in part by the - 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 . 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 Are you listening to this podcast on the move? Get to the show notes here:
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VRS645 - Duct Tape Doesn’t Scale: Onboarding, Training, and Thriving in 2026
01/07/2026
VRS645 - Duct Tape Doesn’t Scale: Onboarding, Training, and Thriving in 2026
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 short-term rental businesses. Drawing from Mike’s personal experience onboarding at a new job in the pickleball industry, they reveal how even fast-growing companies can feel “held together by duct tape” without strong onboarding systems. This episode kicks off a multi-part series on training, development, and systems thinking in STR businesses - highlighting why formal training is often overlooked and how it can transform team performance, guest experience, and business efficiency. ________________________________________________________________________________________________________ 📣 Episode Sponsor: STRAIT Chat & the AI Ambassador Program This episode is brought to you in part by the - 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 . 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 Are you listening to this podcast on the move? Get to the show notes here:
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VRS644 - Forecasting 2026: Tech, Trust, and Transformation in Vacation Rentals with David Angotti
12/31/2025
VRS644 - Forecasting 2026: Tech, Trust, and Transformation in Vacation Rentals with David Angotti
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 renewed focus on local hospitality, David brings a candid and insightful perspective from inside some of the industry’s most talked-about brands, including his transition from Guesty to Casago. You'll hear his thoughts on how Casago is rewriting the rulebook for franchise growth, why property managers must prioritize owner relationships, and what not to settle for when choosing your tech stack in 2026. Whether you're feeling excited or overwhelmed by where the industry is heading, this conversation offers clarity, inspiration, and actionable advice to start your year strong. ________________________________________________________________________________________________________ 📣 Midroll Sponsor: STRAIT Chat & the AI Ambassador Program This episode is brought to you in part by the - 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 . 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 Are you listening to this podcast on the move? Get to the show notes here:
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VRS643 – How Voice AI Can Elevate Hospitality Without Losing the Human Touch – with Eliseo Palous
12/24/2025
VRS643 – How Voice AI Can Elevate Hospitality Without Losing the Human Touch – with Eliseo Palous
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 fascinating journey from starting as an intern in a small property management company to co-founding a business at the forefront of AI-powered communication. His insights into the human challenges behind tech adoption and the risks of depersonalized service hit home for any operator trying to scale without losing soul. This conversation is a thoughtful guide for anyone navigating the balance between automation and authentic guest experience, and a must-listen if you’ve ever felt overwhelmed - or skeptical - about bringing AI into your business. ________________________________________________________________________________________________________ 📣 Midroll Sponsor: STRAIT Chat & the AI Ambassador Program This episode is brought to you in part by the - 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 . 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 Are you listening to this podcast on the move? Get to the show notes here:
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VRS642 - How Stacey St. John Built a High-Performing STR Portfolio From Scratch
12/17/2025
VRS642 - How Stacey St. John Built a High-Performing STR Portfolio From Scratch
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 didn’t just enter the industry - she transformed her life through it. Tune in to hear how she went from buying two “ugly” condos during COVID, to building a thriving business, managing properties with purpose, and cultivating one of the largest online communities for women in STR. If you’ve ever wondered how to spot an opportunity in a down market, manage with integrity, or build a brand that resonates, this conversation is for you. ________________________________________________________________________________________________________ 📣 Midroll Sponsor: STRAIT Chat & the AI Ambassador Program This episode is brought to you in part by the - 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 . 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 Are you listening to this podcast on the move? Get to the show notes here:
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VRS641 - The Insurance Housing Opportunity: What Every STR Operator Should Know with Jake Mast
12/10/2025
VRS641 - The Insurance Housing Opportunity: What Every STR Operator Should Know with Jake Mast
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 AI solutions. Jake shares his unconventional journey - from CPA to Hollywood actor to vacation rental host - and how that ultimately led him to carve out a niche in insurance relocation housing. With a growing network of 6,000+ landlords and boots-on-the-ground resources across North America, Jake’s mission is clear: place displaced families quickly and responsibly into homes that reflect the life they’ve had to leave behind. ________________________________________________________________________________________________________ 📣 Midroll Sponsor: STRAIT Chat & the AI Ambassador Program This episode is brought to you in part by the - 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 . 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 Are you listening to this podcast on the move? Get to the show notes here:
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VRS640 - Why the FIFA World Cup 2026 Starts NOW for Your Vacation Rental with Mark Simpson
12/03/2025
VRS640 - Why the FIFA World Cup 2026 Starts NOW for Your Vacation Rental with Mark Simpson
📌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 announced, and it’s also when the first wave of global bookings will begin. If you're located in or near any of the 16 host cities across the U.S., Canada, and Mexico, this episode is your 48-hour warning to update your pricing, minimum stays, and booking policies before fans (and corporates!) snatch up your nights at undervalued rates. 🌎 Cities Hosting FIFA 2026: Vancouver, Seattle, San Francisco, Los Angeles, Guadalajara, Mexico City, Monterrey, Houston, Dallas, Kansas City, Atlanta, Miami, Toronto, Boston, Philadelphia, New York/New Jersey. If you're within a 1-3 hour drive of any of these cities, this episode is especially important for you. ________________________________________________________________________________________________________ 📣 Midroll Sponsor: STRAIT Chat & the AI Ambassador Program This episode is brought to you in part by the - 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 . 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 Are you listening to this podcast on the move? Get to the show notes here:
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VRS639 - Optimizing for AI: What Short-Term Rental Brands Need to Know About GEO and the Future of Search with Neely Khan
11/26/2025
VRS639 - Optimizing for AI: What Short-Term Rental Brands Need to Know About GEO and the Future of Search with Neely Khan
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 around terms like SEO, GEO, and AEO, you’re not alone. But understanding these isn’t optional anymore - it’s essential if you want your business to remain visible and relevant in today’s evolving digital landscape. Neely breaks things down beautifully. We talk about the difference between Search Engine Optimization (SEO) and Generative Engine Optimization (GEO), and how Answer Engine Optimization (AEO) fits into the mix. More importantly, she shares how vacation rental professionals can start optimizing their content for AI-driven platforms like ChatGPT, Perplexity, and Microsoft Copilot - without losing the soul of their brand. ________________________________________________________________________________________________________ 📣 Midroll Sponsor: STRAIT Chat & the AI Ambassador Program This episode is brought to you in part by the - 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 . 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 Are you listening to this podcast on the move? Get to the show notes here:
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VRS638 - Democratizing Genius: How Dr. Rachel Gainsbrugh Uses AI to Supercharge Short-Term Rental Success
11/19/2025
VRS638 - Democratizing Genius: How Dr. Rachel Gainsbrugh Uses AI to Supercharge Short-Term 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 custom tools, and teaching property managers how to automate without losing the personal touch. Whether you're just curious or already using AI, you'll walk away with practical ideas to try in your business. ________________________________________________________________________________________________________ 📣 Midroll Sponsor: STRAIT Chat & the AI Ambassador Program This episode is brought to you in part by the - 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 . 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 Are you listening to this podcast on the move? Get to the show notes here:
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VRS637 - AI in Action: What STR Hosts Can Learn from the AI for Business Summit
11/12/2025
VRS637 - AI in Action: What STR Hosts Can Learn from the AI for Business Summit
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 must-listen. 📣 Midroll Sponsor: STRAIT Chat & the AI Ambassador Program This episode is brought to you in part by the - 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 . 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 Are you listening to this podcast on the move? Get to the show notes here:
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VRS636 - Scaling Smart: How to Spot the Owners Who’ll Sabotage Your Growth
11/05/2025
VRS636 - Scaling Smart: How to Spot the Owners Who’ll Sabotage Your Growth
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: STRAIT Chat & the AI Ambassador Program This episode is brought to you in part by the - 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 . 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 Are you listening to this podcast on the move? Get to the show notes here:
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VRS635 - From Tinkering to Transformation: Building an AI Adoption Strategy for Your Vacation Rental Business
10/29/2025
VRS635 - From Tinkering to Transformation: Building an AI Adoption Strategy for Your Vacation Rental Business
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 way. 📣 Midroll Sponsor: STRAIT Chat & the AI Ambassador Program This episode is brought to you in part by the - 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 . 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 Are you listening to this podcast on the move? Get to the show notes here:
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VRS634 - The Direct Booking Mindset Shift: What Every Host Needs to Hear Right Now
10/22/2025
VRS634 - The Direct Booking Mindset Shift: What Every Host Needs to Hear Right Now
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 - 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 Are you listening to this podcast on the move? Get to the show notes here:
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VRS633 - The Trustology: The Secret to a Successful Direct Booking Strategy with Chris Maughan
10/15/2025
VRS633 - The Trustology: The Secret to a Successful Direct Booking Strategy with Chris Maughan
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 - 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 Are you listening to this podcast on the move? Get to the show notes here:
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VRS632 - How to Transform Your Short Term Rental Business with Google’s NotebookLM
10/08/2025
VRS632 - How to Transform Your Short Term Rental Business with Google’s NotebookLM
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 - 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 Are you listening to this podcast on the move? Get to the show notes here:
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VRS631 - Are You a Digital Sharecropper? Taking Back Control with Humphrey Bowles
10/01/2025
VRS631 - Are You a Digital Sharecropper? Taking Back Control with Humphrey Bowles
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 - 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 Are you listening to this podcast on the move? Get to the show notes here:
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VRS630 - Build Trust, Book Direct: Lessons from Louis Andrews of OVO Network
09/24/2025
VRS630 - Build Trust, Book Direct: Lessons from Louis Andrews of OVO Network
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 - 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 Are you listening to this podcast on the move? Get to the show notes here:
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VRS629 - From Digital Guides to Donut Walls: Inside a Next-Gen Guest Experience
09/17/2025
VRS629 - From Digital Guides to Donut Walls: Inside a Next-Gen Guest Experience
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 - 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 Are you listening to this podcast on the move? Get to the show notes here:
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VRS628 - Why Local Wins: The Five Pillars for Success You Must Follow - with Ashley Ching
09/10/2025
VRS628 - Why Local Wins: The Five Pillars for Success You Must Follow - with Ashley Ching
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 , 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 - 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 Are you listening to this podcast on the move? Get to the show notes here:
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VRS627 - Thriving in the Age of AI and Short-Term Rentals with Bart Sobies
09/03/2025
VRS627 - Thriving in the Age of AI and Short-Term Rentals with Bart Sobies
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 - 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 Are you listening to this podcast on the move? Get to the show notes here:
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VRS626 - Tech-Enabled Hospitality with Jessica Gillingham of Abode Worldwide
08/27/2025
VRS626 - Tech-Enabled Hospitality with Jessica Gillingham of Abode Worldwide
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 - 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 Are you listening to this podcast on the move? Get to the show notes here:
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VRS625 - Five Quick Wins to Start Using AI in Your STR Business Today
08/20/2025
VRS625 - Five Quick Wins to Start Using AI in Your STR Business Today
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. >> Are you listening to this podcast on the move? Get to the show notes here:
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VRS624 - Trust, Tech & Storytelling: The Keys to a High-Converting STR Website
08/13/2025
VRS624 - Trust, Tech & Storytelling: The Keys to a High-Converting STR Website
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 >> 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. >> Are you listening to this podcast on the move? Get to the show notes here:
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VRS623 - Safety Sells: Why STR Leaders Are Putting Protection First
08/06/2025
VRS623 - Safety Sells: Why STR Leaders Are Putting Protection First
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 >> 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. >> Are you listening to this podcast on the move? Get to the show notes here:
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VRS622 - Navigating Growth, Change, and True Hospitality with Jackie Norde from Casago
07/30/2025
VRS622 - Navigating Growth, Change, and True Hospitality with Jackie Norde from Casago
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 >> 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. >> Are you listening to this podcast on the move? Get to the show notes here:
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VRS621 – The Power of Storytelling: How Hospitality Brands Can Stand Out in a Sea of Sameness
07/23/2025
VRS621 – The Power of Storytelling: How Hospitality Brands Can Stand Out in a Sea of Sameness
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 >> 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. >> Are you listening to this podcast on the move? Get to the show notes here:
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VRS620 - Staying Human: The Power of Vulnerability in Vacation Rental Leadership
07/16/2025
VRS620 - Staying Human: The Power of Vulnerability in Vacation Rental Leadership
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 >> 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. >> Are you listening to this podcast on the move? Get to the show notes here:
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VRS619 - Making AI Work for You: Insights, Use Cases, and a New Industry Survey with Fred Bassili of Hostfully
07/09/2025
VRS619 - Making AI Work for You: Insights, Use Cases, and a New Industry Survey with Fred Bassili of Hostfully
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. Make sure you complete The Strategic Ai Adoption Survey >> You will get the chance to win an iPad and get access to '24 Use Case 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. >> Are you listening to this podcast on the move? Get to the show notes here:
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VRS618 - Legacy, Leadership & AI: Inside the Evolution of Cottage Connection of Maine with Alexis Miller
07/02/2025
VRS618 - Legacy, Leadership & AI: Inside the Evolution of Cottage Connection of Maine with Alexis Miller
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. >> Are you listening to this podcast on the move? Get to the show notes here:
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