SmartStay Show - Short Term Rental Counsel + Coaching | Airbnb Hosting Tips
Welcome to the SmartStay Show, your go-to podcast for mastering Short-Term Rentals on Airbnb, Vrbo, and beyond. For more Airbnb tips, visit smartstayshow.com and smartstaycoaching.com. Hosted by 30-time Airbnb Superhost Jason Muth and Real Estate Attorney Rory Gill, we equip you with the tools to launch, manage, and optimize your vacation rental like a pro. Unlike other shows, we specifically cater to owners of small-but-mighty portfolios who self-manage their properties. Each episode delivers expert insights, legal tips, and proven strategies from successful hosts across the U.S. Whether you’re buying your first property, improving your listing, or looking to stay ahead of the competition, we offer actionable advice and real-life stories to help you thrive. From pricing strategies to guest communication, we provide the playbook to turn your property into a top-performing rental. Subscribe now and unlock your rental’s full potential with the SmartStay Show!
Episodes
May 13, 2025 • 39 mins
What Happens When Your Airbnb Becomes a Disaster?
Join us as we sit down with Andy Gurczak, a seasoned public adjuster and new short-term rental owner, to explore the often-overlooked world of insurance claims for vacation rentals.
In this eye-opening episode, Andy reveals insider tips on protecting your property and why your standard homeowner's insurance policy might not have your back when you're hosting on platforms like Airbn...
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May 6, 2025 • 41 mins
Did you know your short-term rental could be a powerful tax-saving machine?
In this episode, We sit down with Sean Graham—CPA, real estate investor, and cost segregation expert—to uncover how vacation rental owners can legally slash their tax bills using smart depreciation strategies.
From bonus depreciation and the short-term rental loophole to material participation rules, Sean breaks down complex tax concepts in a way tha...
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April 29, 2025 • 48 mins
Are you ready to find your next cash-flowing short-term rental property — and actually know it’s a winner before you buy?
In this episode, We sit down with John Bianchi, the self-proclaimed "Airbnb Data Guy," who's helped uncover over 200 profitable STR properties. John pulls back the curtain on how to spot the best markets, why understanding local regulations is critical, and how effective marketing can make or break your renta...
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April 22, 2025 • 43 mins
Are you putting all your hosting eggs in the Airbnb basket? What if there's a smarter way to grow your short-term rental business?
In this eye-opening episode, we sit down with Mark Simpson, founder of Boostly and one of the world’s top experts in direct booking strategies. From running a family farm stay to becoming a global authority on short-term rental marketing, Mark’s journey is as inspiring as it is informative.
Discover why...
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April 15, 2025 • 39 mins
Are you leaving money on the table with your short-term rental?
In this episode, We sit down with CPA and tax strategist Anne Gannon to uncover the often-overlooked financial advantages of real estate investing. Anne simplifies complex tax topics and reveals how savvy investors use short-term rentals not just for income—but to build long-term wealth.
From depreciation strategies to smart tax planning, you'll learn how to make the m...
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April 8, 2025 • 30 mins
"What if your vacation rental came with VIP treatment?"
Dive into the world of luxury short-term rentals with Kevin Duran, founder of JKW Vacation Club. In this episode, we explore a game-changing approach to vacation stays—one that goes beyond traditional Airbnb bookings.
Kevin shares how his innovative membership model offers travelers a full concierge experience, including airport shuttles, grocery delivery, and exclusive local...
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April 1, 2025 • 40 mins
Is Your Short-Term Rental Truly Welcoming to All Guests?
In this must-listen episode, we sit down with Mrs. Schneider, an expert who understands the real challenges travelers with disabilities face. They uncover practical, budget-friendly ways to make your rental more accessible—like installing lever door handles, modifying bathrooms, and making small yet impactful changes.
With nearly 70 million Americans living with disabilities...
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March 25, 2025 • 34 mins
Would You Quit Your 9-to-5 to Build a Short-Term Rental Empire?
Payton Cummings did exactly that—leaving behind a steady paycheck to scale a thriving 17-property short-term rental business! In this episode, she shares her journey from corporate consulting to full-time entrepreneurship, the mindset shifts that made it possible, and how community and strategy helped her think bigger.
If you're dreaming of turning your side hustle i...
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March 18, 2025 • 34 mins
Ever wondered if one spontaneous decision could completely change your career? That’s exactly what happened to Jayla Siciliano. While on vacation, she crunched the numbers on a short-term rental, saw its potential, and the next day, put in an offer on her first property.
In this episode of SmartStay Show, Jayla takes us through her journey from that impulsive purchase to building a thriving short-term rental business across multi...
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March 11, 2025 • 31 mins
What makes a short-term rental truly unforgettable? In this episode of SmartStayShow, we uncover the secrets behind top-performing vacation rentals with Mark Lumpkin, sales director at STRCRIBS. From bachelorette-themed escapes in Nashville to hidden speakeasies and glow-in-the-dark mini-golf, Mark shares expert tips on designing spaces that attract guests—and boost revenue.
We dive into bold colors, eye-catching murals, and Inst...
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March 4, 2025 • 60 mins
Ever wondered what it’s like to live as a digital nomad, staying in over 30 short-term rentals around the world?
In this exciting episode of the Smart Stay Show, we sit down with Eric and Marissa Dingler, a family that sold most of their possessions and turned their home into a life of adventure. From Costa Rica to Liverpool, the Dinglers share their incredible journey and insights into the world of short-term rentals.
As experi...
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February 25, 2025 • 56 mins
Can You Build a Thriving Short-Term Rental Business While Working Full-Time?
In this episode, we sit down with Jim McGowan, a seasoned sales professional who has successfully built a profitable short-term rental portfolio—all while maintaining his full-time job!
Jim takes us through his journey, from an early misstep in fractional ownership to fully owning and managing two stunning vacation rentals in Bartlett, New Hampshire: Sum...
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February 18, 2025 • 33 mins
Can AI Handle Guest Communication Better Than You?
In this episode of The Smart Stay Show, we sit down with Jay Ulrich, CEO and co-founder of HostBuddy.ai, to explore how AI is revolutionizing short-term rental management.
Jay, a former civil engineer turned short-term rental host, shares his journey from scaling Select Stays to 40 units to developing an AI-powered platform that learns your style, responds like you (yes, even with...
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February 11, 2025 • 35 mins
Can hard money lending and short-term rentals be the ultimate power duo?
In this episode of The Smart Stay Show, We sit down with David Little, co-founder of Crown Capital Resources, to explore how savvy investors are using short-term rentals as a game-changing exit strategy.
We dig into DSCR loans, the Burr method for vacation rentals, and how tools like AirDNA are influencing lending decisions. David shares insider tips on lev...
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February 4, 2025 • 42 mins
How did one property cover an entire mortgage—and spark a 30-property empire?
In this episode of the Smart Stay Show, We sit down with Islam Elgarhi, a short-term rental investor and entrepreneur, to uncover how he turned a chance discovery into a thriving business.
From scaling his portfolio with smart systems to creating an AI tool that helps hosts tackle unfair reviews, Islam shares his secrets for success. Plus, we explore ho...
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January 28, 2025 • 36 mins
Ever wonder why some hosts seem to always get glowing reviews while others struggle?
In this episode of the Smart Stay Show, I’m joined by my business partners Alex Steeg and Kory Himmer to dive into the game-changing power of proactive communication in short-term rental hosting.
We break down how setting clear expectations upfront can prevent negative reviews and enhance guest satisfaction. From booking confirmations to review r...
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January 23, 2025 • 42 mins
Ever Dealt With a Water Damaged Rental Property? This Could Save You Thousands.
As short-term rental owners, Rory and I have seen it all - from the good, the bad, to the downright disastrous. One fateful night, we got that dreaded 2am call about a water damaged property, and let me tell you, it was a nightmare.
But what happened next is the real story. In this episode, we sit down with Darren Pettyjohn, the co-founder of Proper In...
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January 21, 2025 • 41 mins
Ever wondered how hostels are redefining the travel experience?
In this episode, I sit down with Nate St Cyr, the visionary co-founder of Malama Capital and Howzit Hostels, to uncover how he’s revolutionizing the traditional hostel concept. From daily pancake breakfasts and Margarita nights to crafting a vibrant, community-driven atmosphere, Nate shares his journey of turning a simple idea into a thriving hospitality brand.
We div...
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January 7, 2025 • 36 mins
What happens when a passion for design meets the wild beauty of Joshua Tree? In this episode, Rory Gill and I sit down with Dre Shapiro, a designer whose journey into short-term rentals is as inspiring as it is unexpected. Dre fell in love with a vacation rental in Joshua Tree, turned it into her own, and transformed it into a guest favorite through her incredible design sensibilities.
We discuss her unique approach to creating u...
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January 2, 2025 • 47 mins
Ready to learn from one of the top short-term rental experts in the game?
In this episode of the Smart Stay Show, we’re joined by Garrett Brown, the resident expert at Bigger Pockets, who shares his journey from hospitality to real estate success.
Garrett reveals how his background in hotels and restaurants shaped his approach to managing multiple short-term rentals. He also talks about the importance of staying positive, adapting...
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