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.

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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

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.

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

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

>> Register today to attend SSTIR Crazy Month 2025

According to the 2024 Booking.com Sustainability Survey, 75% of global travelers want to make more eco-friendly travel choices in the next 12 months. However, 43% admit to feeling guilty when their choices fall short. This reveals a growing trend: while there’s a demand for sustainability, travelers still struggle to act on it—unless the choice is made easy for them.

That’s exactly the challenge StayWise Rentals is facing this week. As competitors successfully market their eco-friendly rentals and attract sustainability-conscious travelers, StayWise is falling behind. Their properties are energy inefficient, their waste management is outdated, and they haven’t figured out how to make sustainability work without breaking the bank.

Enter Bob Garner—a sustainability expert and founder of EnviroRental—who joins Heather Bayer to help StayWise Rentals navigate their sustainability crisis. Bob brings decades of experience in vacation rental sustainability and shares practical, no-nonsense advice for property managers who want to future-proof their businesses while keeping costs in check. 

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/VRS600

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

>> Register today to attend SSTIR Crazy Month 2025

This week, we tackle one of the biggest challenges short-term rental operators face: regulations. With StayWise Rentals in crisis, our expert Dana Lubner from Rent Responsibly joins us to break down the strategies for compliance, advocacy, and overcoming regulatory hurdles.

After weeks of dealing with trust issues, safety failures, and an insurance disaster, Sarah and Mike Chen at StayWise Rentals were blindsided by a notice from their local municipality. New short-term rental regulations had just been passed, and StayWise had only 60 days to comply with a long list of requirements:

• Mandatory fire safety upgrades across all properties.

• New occupancy limits based on square footage.

• A requirement to have a local representative available 24/7.

• A $1,500 licensing fee per property.

• Surprise city inspections—two properties even received cease and desist orders.

With property owners panicked, guests caught in the crossfire, and mounting compliance costs, StayWise is at a crossroads. Can they navigate this storm without losing their 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/VRS599

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 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