VRS598 - Lessons Learned from a Disaster Scenario with Nick Massey - Proper Insurance
Release Date: 02/12/2025
VRS614: Marketing Shifts, AI in Search, and the Future of Vacation Rental Websites with Conrad O’Connell
Vacation Rental Success
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...
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VRS613 - Why Every Vacation Rental Business Needs an AI Champion - Now
Vacation Rental Success
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...
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VRS612 - Access for All: How One Woman’s Mission and Expedia’s Support Are Transforming the Way We Host
Vacation Rental Success
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...
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VRS611 - Leadership by Culture: How Rachel Alday Built Loyalty and Hospitality Through Intentional Team Values
Vacation Rental Success
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...
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VRS610 - The Quiet Power of Leadership: Steve Schwab on Earning Loyalty and Driving Change
Vacation Rental Success
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 driving force behind a national franchise brand, Steve’s story is anything but typical. In this...
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VRS609 - What Type of Leader Are You? Reflections from the Short-Term Rental Industry
Vacation Rental Success
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, weaving in personal stories and rich insights from some of the most inspiring voices in the...
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VRS608 - Are You Born to Lead? Lessons in STR Leadership with Ali Cammelletti
Vacation Rental Success
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 formal training. Together, they explore the very real challenges of leadership in the short-term...
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VRS607 - Leading with Intention: Matt Landau on Breakthroughs, Burnout, and the Power of Pause
Vacation Rental Success
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 Inner Circle, Matt has always led by example. But over the last few years, he’s taken a big...
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VRS606 - AI Meets Hospitality: Shahar Goldboim on Building the World’s First AI-Powered PMS
Vacation Rental Success
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, human-centered heart of hospitality. From automating time-consuming tasks to interpreting...
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VRS605 - Using AI to Work Smarter, Not Harder with Mark Simpson
Vacation Rental Success
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 hosts and property managers increase their direct bookings. With years of experience in digital...
info_outlineIn 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 short-term rental insurance policy that covers both commercial and personal use of your vacation rental.
>> Discover more about Proper Insurance
>> Register today to attend SSTIR Crazy Month 2025
“It just makes sense to buy the best cover available," said a lone voice in a Facebook group in answer to the question “Where can I get the cheapest insurance?”.
Sadly many of the responses pointed to cut price options which is clearly the route Staywise Rentals went when they started out. And now to their horror, an incident at one of their prime beachfront homes has brought home the folly of this choice.
In this episode and third week of the SSTIR Crazy event where we follow the issues Stay Wise Rentals are facing, Nick Massey, a seasoned expert in vacation rental insurance and the director of sales at Proper Insurance, shares his thoughts on the direction they need to take.
Nick has extensive experience in identifying coverage gaps and optimizing insurance strategies for property managers, and he brings a wealth of knowledge to one of the most daunting aspects of vacation rental management. He gets right into the complexities of insurance policies, highlighting common pitfalls and actionable strategies to protect rental properties effectively.
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/VRS598