VRS486 - What to Ask, and How to Ask - A Chat GPT Masterclass for Short-Term Rentals with Bart Sobies

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 conversation, he opens up about the early moments that launched his career, the foundation of the ORANGE Credo that anchors Casago’s culture, and what it means to scale a values-based business without losing its soul - especially in the wake of one of the industry’s biggest mergers to date. If you’re thinking about growth, culture, or the future of professional property management, this episode delivers both heart and strategy in equal measure. 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/VRS610

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 business. This episode highlights the remarkable leadership archetypes shaping our space - from the spiritual and creative to the cultural and transformational. Whether you’re managing a team, growing a portfolio, or simply aiming to lead with more purpose, this episode is a must-listen. 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/VRS609

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 rental world and how to navigate them with grace, strategy, and self-awareness. 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/VRS608

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 step back - literally and figuratively - to re-evaluate what leadership really means. His latest project, Here Goes Nothin’, is all about helping short-term rental professionals find clarity, reconnect with purpose, and lead from a place of authenticity. 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/VRS607

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 emotional cues in guest communication, Boom is more than a tool - it's a vision for the future of property management. Shahar shares how Boom was born out of real-world frustration, why AI isn’t replacing hospitality, but making room for more of it, and how his family-run team is scaling technology with soul. 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/VRS606

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 marketing and hospitality, Mark has become a leading advocate for independent hosts looking to take back control from OTAs.  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/VRS605

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 tackle the challenge so many of us are facing right now: how do you choose the right AI tools without getting overwhelmed by the endless options? With over 32,000+ tools out there (yes, really), it’s easy to fall into analysis paralysis or end up subscribing to a dozen platforms you barely use. Nihal and I share our favorite go-to tools, what we’re using in our own businesses, and how to evaluate which platforms are truly worth your time and money. We also explore the difference between individual LLMs (like ChatGPT, Claude, and Gemini) versus aggregator platforms (like Abacus and Poe), and how each one fits into a short-term rental operator’s toolkit. We even take a side trip into dog diet planning using Claude (yes, AI really can do that), and why being intentional is the most important skill you can develop when integrating AI into your 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/VRS604      

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 optimizing SEO and automating guest communication, AI is changing the game. But how do you use it effectively - without getting overwhelmed? In this episode, marketing expert Nihal Salah joins Heather Bayer to break down practical AI use cases for short-term rental marketing. You’ll discover how AI can help streamline content creation, enhance guest experiences, and drive more direct bookings - all while saving you time. Why AI Matters for Your Vacation Rental Marketing AI isn't just a trend - it’s a powerful tool that can help hosts and property managers work smarter, not harder. Nihal shares how AI can: Improve your property listings with optimized descriptions and compelling titles Boost your SEO strategy to increase visibility and direct bookings Analyze guest reviews to uncover hidden trends and key selling points Repurpose content efficiently across multiple platforms Enhance guest communication through AI-powered assistants and chatbots If you’ve been curious about AI but unsure where to start, this episode will give you clear, actionable steps to integrate AI into your marketing strategy. 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/VRS603      

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 but also supercharge growth and efficiency, particularly in owner acquisition. In this episode Brooke shares the platforms he uses the most and offers advice and recommendations on their use. 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/VRS602  

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, most of us have used enough of them to be ‘seen’ as ChatGPT users, and the grammar police aren’t taking prisoners.   It’s time to take back our humanness and our attention to sharing personal brand in a way that makes us unique.If you have ever been in a room where Amber Hurdle is speaking, you’ll appreciate her passion for branding and marketing, and will have come away with a renewed enthusiasm for making your mark.   In this episode, Amber brings the zest she shares in her opening keynotes to the topic of strategic use of AI in the ways we communicate and build our brands.‍ 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/VRS601