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...
Jul 09, 2025•51 min
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...
Jul 02, 2025•44 min
In this episode of the Vacation Rental Success Podcast, host Heather Bayer shares her top takeaways from the AI for Business Summit in Orlando, diving into the transformative power of artificial intelligence and how vacation rental professionals can leverage it to drive growth, efficiency, and guest experience Revolutionize Your Employee Onboarding with THRIVE Essentials: Faster Training, Stronger Teams, Better Results! Discover how THRIVE Essentials accelerates onboarding for new property manag...
Jun 25, 2025•42 min
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 industry experience and recent immersion in AI tools, Heather shares insights into how vacation rental operators can use AI not only to save time and money, ...
Jun 18, 2025•45 min
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 protect your business. Then, we switch gears and dive headfirst into the world of AI in vacation rentals. Mark shares how he’s been helping hosts build cust...
Jun 11, 2025•52 min
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 professionally. Conrad shares what’s changed (including growing his family and his business) and what’s stayed consistent in the ever-evolving digital landscape. ...
Jun 04, 2025•54 min
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 transformative potential of artificial intelligence. In this conversation Heather and Mike talk about why companies must move from passive awareness ...
May 28, 2025•51 min
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 Group through their Open World Accelerator Program. Together, Heather and Lorraine dive into what accessibility really means today (spoiler alert: it...
May 21, 2025•55 min
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 few properties to a high-performing, values-driven team of nearly 60 people across three markets. What started as a “mom-and-pop” business became a ...
May 14, 2025•51 min
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 here and the deeply held leadership values that have shaped the company’s evolution. From climbing rooftops in Rocky Point, Mexico, to becoming the ...
May 07, 2025•43 min
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 vacation rental industry. From traditional leadership styles to emotionally intelligent approaches, she guides us through a wide spectrum of frameworks...
Apr 30, 2025•34 min
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 Cammelletti, who has spent over 20 years helping hospitality professionals grow into confident, emotionally intelligent leaders - often without any form...
Apr 23, 2025•46 min
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 rental industry. From managing boutique vacation rentals in Panama City’s historic Casco Viejo to founding The Vacation Rental Marketing Blog and The Inn...
Apr 16, 2025•52 min
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 Goldboim, the dynamic founder of Boom, to explore how artificial intelligence is reshaping the vacation rental industry - without sacrificing the personal, ...
Apr 09, 2025•51 min
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 the personal touch that makes direct bookings successful. Mark Simpson is the founder of Boostly, a platform dedicated to helping short-term rental hos...
Apr 02, 2025•53 min
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 rental marketer, Nihal Salah - and trust me, if you thought the first conversation was packed, this one goes even deeper. In this episode, we tack...
Mar 26, 2025•56 min
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 Wondering how AI can make your vacation rental marketing more efficient and impactful? From crafting compelling property descriptions to optimizi...
Mar 19, 2025•54 min
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 and has been a trailblazer in the vacation rental industry for over 17 years. He’s also fully immersed in AI to not only streamline operations b...
Mar 12, 2025•46 min
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 Showing….and it’s stripping the authenticity out of your brand. ”Whether it’s an over-use of hyphens, emojis or particular sentence structures, ...
Mar 05, 2025•1 hr
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 of your operations. ***Use code SSTIRCRAZY for 50% off your first annual plan*** >> Discover more about Guesty in the Virtual Vendor Showcase >...
Feb 26, 2025•44 min
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 your operations. ***Use code SSTIRCRAZY for 50% off your first annual plan*** >> Discover more about Guesty in the Virtual Vendor Showcase >>...
Feb 19, 2025•47 min
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 SSTIRCRAZY for 50% off your first annual plan*** >> Discover more about Guesty in the Virtual Vendor Showcase Proper has developed a specialty ...
Feb 12, 2025•56 min
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 27-28, 2025. This episode of the podcast and SSTIR Crazy Month is sponsored by Guesty your all-in-one platform for hospitality businesses to a...
Feb 05, 2025•41 min
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, April 27-28, 2025. This episode of the podcast and SSTIR Crazy Month is sponsored by Guesty your all-in-one platform for hospitality businesses...
Jan 29, 2025•50 min
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 SSTIR Crazy Month is sponsored by Guesty your all-in-one platform for hospitality businesses to automate and optimize every aspect of your operations. &g...
Jan 22, 2025•47 min
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 anyone in the short-term rental business. This is your opportunity to take advantage of a month of incredible content that will help protect, you, your...
Jan 15, 2025•42 min
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 where it gets exciting - Steve and his team are harnessing AI to transform everything from how job ads are crafted to how talent is optimized. In this ...
Jan 08, 2025•51 min
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 serving as Chief Evangelist at Guesty. He’s also an incredible storyteller and someone who just gets the ins and outs of this business like few other...
Jan 01, 2025•54 min
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 Nihal Salah, a marketing strategist with a knack for demystifying marketing strategies for businesses. With extensive experience in leveraging AI to stre...
Dec 25, 2024•49 min
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 Masson is a seasoned entrepreneur and thought leader in the short-term rental industry. With experience managing properties in Bali, Saint Barts, and now V...
Dec 18, 2024•48 min
