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 >>https://www.hostfully.com/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. >> THRIVE Essentials Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/VRS620

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 >>https://www.hostfully.com/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. >> THRIVE Essentials Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/VRS619

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. >> THRIVE Essentials Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/VRS618

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 management staff, boosting performance and reducing turnover. >> THRIVE Essentials Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/VRS617

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, but also to transform their business operations. Through a live example of AI-generated podcast content, she showcases how the future of AI isn't something to fear - but a tool to empower. 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. >> THRIVE Essentials Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/VRS616

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 custom GPTs, boost productivity, and take back control of their marketing strategies. If you're curious about how to harness AI without feeling overwhelmed, this episode delivers a masterclass in cutting through the fluff and getting to what works. 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. >> THRIVE Essentials Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/VRS615

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. We talk about how Google’s AI-powered search is impacting SEO, how paid ads are gaining traction again, and what content strategies still work in 2025. If you’ve ever felt confused about where to put your marketing dollars - or how to write content that still gets found - this episode is packed with clarity. 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. >> THRIVE Essentials Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/VRS614

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 to active implementation. The best way to do this is to empower someone within their business to lead the AI charge and they explain the steps to get this underway. 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. >> THRIVE Essentials Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/VRS613

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’s not just ramps and wide doors), and how simple, low-cost features like under-counter lighting, secondary locks, and hard surface driveways can dramatically open your property to a broader guest base - including families with children, seniors, people recovering from surgery, and neurodivergent travelers. Lorraine also shares her personal journey, building an inclusive rental to meet her family's needs, and the lightbulb moment that sparked the idea for a global platform. Her story is as inspiring as it is actionable. This is a must-listen if you've ever thought, "Accessibility isn't for my market." Think again - Lorraine shows us why accessible design is not only the right thing to do, it's really good business. 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. >> THRIVE Essentials Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/VRS612

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 case study in leadership - rooted in authenticity, driven by values, and centered around a deep commitment to both team and guest experience. Whether you’re managing five properties or five hundred, this episode offers practical insights on how to lead with purpose, build loyalty from the inside out, and create a culture that sustains long-term growth and excellence. 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. >> THRIVE Essentials Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/VRS611