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Vacation Rental Success

Heather Bayer aka @CottageGuru

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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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2024 showed us that direct booking isn’t dead. On the contrary, the appetite for building a strategy for independence from the OTAs is as strong as ever, if a little more challenging. For it to be successful, there’s work involved, but for those with enthusiasm and commitment, it will be fulfilling in the long run. Joining us in this episode is Nih…
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Is Airbnb’s new co-hosting network a game-changer for property management, or a challenge for traditional operators? In this episode Heather is joined by the founder of Rental Scale-up and Global Head of Product Marketing at PriceLabs, Thibault Masson, to discuss the opportunities, threats and potential of Airbnb’s latest endeavours. Thibault Masso…
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1 in 36 children in the U.S. have been identified with autism spectrum disorder (ASD), which represents a significant increase from previous years with the prevalence of autism in the U.S. increasing by 312% since 2001. While these are staggering statistics, they also represent an opportunity for vacation rental owners and managers to create the in…
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Is SEO dead in the short-term rental space? According to experts, it remains a vital and evolving component of digital marketing strategies for vacation rental businesses in 2024 and beyond. In this episode, host Heather Bayer sits down with Jill McGee from InterCoastal Net Designs (ICND) to discuss SEO strategies for vacation rental websites. Toge…
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In this episode of the Vacation Rental Success Podcast, host Heather Bayer sits down with her business partner and son, Mike Bayer, to explore The Five Languages of Appreciation in the Workplace. Together, they discuss how these principles can be applied in vacation rental management to motivate, retain, and inspire team members. Mike Bayer is the …
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Following an AHA moment at the VTSTRA Conference in Vermont in early November, where AI was mentioned in just about every presentation, this episode introduces Kate Stoermer from The CEO Host to discuss the practical uses of AI in vacation rental management, from simplifying workflows to optimizing guest experience. Kate Stoermer, founder of The CE…
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When we talk about marketing it’s often about tactical aspects like posting on Instagram, making reels or how to manage influencers. But without a sound marketing strategy behind the tactics, the chance of them succeeding is low. In this episode of the Vacation Rental Success Podcast, host Heather Bayer sits down with marketing strategist Nihal Sal…
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In this episode of the Vacation Rental Success Podcast, host Heather Bayer sits down with Valerie Gangas from Juniper Holiday + Home to discuss how diverse life experiences can shape success in the vacation rental business. Valerie shares how her background in hospitality, real estate, and spirituality drives her unique approach to creating memorab…
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