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, a ...
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Heather Bayer Aka @CottageGuru Podcasts
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VRS616 - A Podcast Within a Podcast: A Look into NotebookLM
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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 industr…
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VRS615 - Direct Bookings, AI, and Airbnb Disruption: A Real Talk with Mark Simpson
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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 protec…
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VRS614: Marketing Shifts, AI in Search, and the Future of Vacation Rental Websites with Conrad O’Connell
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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 professional…
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VRS613 - Why Every Vacation Rental Business Needs an AI Champion - Now
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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…
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VRS612 - Access for All: How One Woman’s Mission and Expedia’s Support Are Transforming the Way We Host
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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…
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VRS611 - Leadership by Culture: How Rachel Alday Built Loyalty and Hospitality Through Intentional Team Values
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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…
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VRS610 - The Quiet Power of Leadership: Steve Schwab on Earning Loyalty and Driving Change
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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 h…
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VRS609 - What Type of Leader Are You? Reflections from the Short-Term Rental Industry
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In this powerful solo episode, Heather Bayer reflects on one of the most fundamental - and often overlooked - questions in the short-term rental space: What kind of leader are you? Through years of podcast interviews and her own journey managing STR properties, Heather unpacks the evolving nature of leadership and how it uniquely manifests in the v…
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VRS608 - Are You Born to Lead? Lessons in STR Leadership with Ali Cammelletti
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Most short-term rental operators didn’t plan on becoming leaders. They started as solopreneurs - cleaning toilets one day, managing a team the next. If you’ve ever found yourself in a leadership role and thought, “How did I get here?”, this episode is for you. In this powerful and relatable conversation, Heather is joined by leadership coach Ali Ca…
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VRS607 - Leading with Intention: Matt Landau on Breakthroughs, Burnout, and the Power of Pause
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In this special episode, we kick off our brand-new Leadership Series with someone who’s been part of this journey from the very beginning - Matt Landau. Matt’s been on the show more than 20 times over the years, but this conversation feels different. It’s deeper, more reflective, and marks a shift in how we talk about leadership in the vacation ren…
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VRS606 - AI Meets Hospitality: Shahar Goldboim on Building the World’s First AI-Powered PMS
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What happens when a vacation rental entrepreneur, his tech-savvy brothers, and a close-knit team of hospitality veterans come together with a mission to solve the biggest operational headaches in property management? You get Boom - the world’s first AI-powered property management system (AIPMS). In this episode, Heather sits down with Shahar Goldbo…
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VRS605 - Using AI to Work Smarter, Not Harder with Mark Simpson
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In this episode of the Vacation Rental Success Podcast, host Heather Bayer sits down with Mark Simpson, the founder of Boostly, to discuss the practical applications of artificial intelligence (AI) for vacation rental hosts. Mark shares how AI can help streamline operations, enhance guest experiences, and optimize marketing efforts—without losing t…
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VRS604 - Cutting Through the AI Noise: How to Choose the Right Tools for Your STR Business
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This episode of the podcast is sponsored by Guesty, your all-in-one platform for hospitality businesses to automate and optimize every aspect of your operations. ***Use code SSTIRCRAZY for 50% off your first annual plan*** >> Discover more about Guesty in the Virtual Vendor Showcase We’re back with Part 2 of my chat with AI educator and vacation re…
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VRS603 - AI-Powered Marketing for Vacation Rentals: What You Need to Know
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This episode of the podcast is sponsored by Guesty, your all-in-one platform for hospitality businesses to automate and optimize every aspect of your operations. ***Use code SSTIRCRAZY for 50% off your first annual plan*** >> Discover more about Guesty in the Virtual Vendor Showcase AI-Powered Marketing for Vacation Rentals: What You Need to Know W…
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VRS602 - Unlocking Efficiency: Exploring AI Solutions in Vacation Rentals with Brooke Pfautz
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This episode of the podcast is sponsored by Guesty, your all-in-one platform for hospitality businesses to automate and optimize every aspect of your operations. ***Use code SSTIRCRAZY for 50% off your first annual plan*** >> Discover more about Guesty in the Virtual Vendor Showcase Brooke Pfautz is the innovative mind behind Vintory and Comparent …
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VRS601 - Is Your ChatGPT Showing? - with Amber Hurdle
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This episode of the podcast is sponsored by Guesty, your all-in-one platform for hospitality businesses to automate and optimize every aspect of your operations. ***Use code SSTIRCRAZY for 50% off your first annual plan*** >> Discover more about Guesty in the Virtual Vendor Showcase In a recent post on Linkedin, Amber Hurdle said: “Your ChatGPT Is …
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VRS600 - From Energy Hog to Eco-Hero with Bob Garner
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We’ve arrived at Week 5 of SSTIR Crazy 2025, and this might be the most critical challenge yet! Sustainability Week is here, and the stakes have never been higher for StayWise Rentals. This episode of the podcast and SSTIR Crazy Month is sponsored by Guesty, your all-in-one platform for hospitality businesses to automate and optimize every aspect o…
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VRS599 - The Compliance Challenge: Strategies for Navigating New Regulations
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We’ve arrived at Week 4 of SSTIR Crazy 2025, and this might be the most critical challenge yet! Regulations Week is here, and the stakes have never been higher for StayWise Rentals. This episode of the podcast and SSTIR Crazy Month is sponsored by Guesty your all-in-one platform for hospitality businesses to automate and optimize every aspect of yo…
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VRS598 - Lessons Learned from a Disaster Scenario with Nick Massey - Proper Insurance
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In this third week of SSTIR Crazy 2025, StayWise Rentals grapples with an insurance nightmare when a malicious pool party threatens to ruin their business. This episode of the podcast and SSTIR Crazy Month is sponsored by Guesty your all-in-one platform for hospitality businesses to automate and optimize every aspect of your operations. ***Use code…
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VRS597 - When Vacation Rental Safety Systems Fail: Lessons from the Field with Justin Ford
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In this second week of SSTIR Crazy 2025, StayWise Rentals grapples with a critical turning point: a safety crisis threatening their direct bookings. Easter Egg #7 [Justin] - >> SSTIR Crazy Registrants can enter this phrase in the gamification section on the app to earn big points towards the 2 VIP Tickets to VR Nation Conference, Austin, TX, April …
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VRS596 - From Questionable to Trustworthy: A Trust Transformation - with Chris Maughan
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In this first week of SSTIR Crazy 2025, StayWise Rentals grapples with a critical turning point: a trust crisis threatening their direct bookings. Easter Egg #3 [Guest-Centric] - >> SSTIR Crazy Registrants can enter this phrase in the gamification section on the app to earn big points towards the 2 VIP Tickets to VR Nation Conference, Austin, TX, A…
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VRS595 - Navigating Change: Why, When and How to Switch Your PMS with David Angotti
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There comes a point in every property manager’s journey where they have to consider whether their chosen property management system is still the right fit. For those who made a strong and well-researched choice early on, this may not be an issue, but for many, that tipping point arrives and needs to be addressed. This episode of the podcast and SST…
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VRS594 - SSTIR Crazy 2025: Tackle the Tough Topics, Win the Grand Prize
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Around this time last year, we had an idea that grew out of a LinkedIn post by Justin Ford. He had expressed his disappointment at the limited attention given to some topics at the 2023 VRMA conference and questioned how we could get more interest in the foundational elements of our business. SSTIR Crazy Month is the perfect FREE online event for a…
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VRS593 - AI at Work: Real-World Applications in the Vacation Rental Industry With Steve Trover
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If you’ve ever wondered how Artificial Intelligence (AI) is shaking things up in the vacation rental industry, you’re in for a treat. Steve Trover has been a driving force in our industry for over 28 years, and through his company, Better Talent, he’s helped over 300 property managers refine their recruitment strategies and operations. But here’s w…
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VRS592 - From Trends to Tactics with David Angotti
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Happy New Year! This special episode - our annual reflection on the last 12 months and a look at where we are going in 2025 - features none other than David Angotti. David’s been in the short-term rental world for years and has done it all - co-founding tech startups, building a successful property management company in the Smoky Mountains, and now…
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