SmartStay Show - Short Term Rental Counsel + Coaching | Airbnb Hosting Tips

Updated: 29 Jul 2025 • 263 episodes
www.smartstayshow.com

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!

Show episodes

What does it take to walk away from a high-paying corporate job and build a 50+ property short-term rental empire? In this episode, I sit down with real estate investor and coach Matt McCall Stillman, along with attorney and legal expert Rory Gill, for a powerful conversation about what it really takes to succeed in th

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Ever wonder what it really takes to pack up your life, move to a new city, and build a short-term rental business from scratch? In this episode, We sat down with my friend Chachi Horgan — a former real estate agent from Maine who took a leap, moved to Florida, and built Roam Ready Vacation Rentals, scaling to 11 proper

56 min
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Can a side hustle built on friendship and a love of travel become something bigger? Join Jason Muth, Rory Gill, and Ethan Sobel as they share the real story behind Prideaway Stays, their co-hosting venture in Provincetown. From a family dream of owning a Cape home to building a guest-first rental brand, this episode di

51 min
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What if your best-performing Airbnb was sitting just a mile away—and you almost missed it? In this episode, we talk with Jeremy Beland, a real estate investor who made the leap from wholesaling to building a killer short-term rental portfolio in Port St. Lucie, Florida. He shares how one overlooked pocket became home t

37 min
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What if your real estate business was designed to serve your life — not run it? In this episode, we chat with Fouad Bazzi, a former banker who left the corporate world to build a thriving short-term rental business centered around freedom, family, and purpose. He shares how he scaled his operations, mentors the next ge

44 min
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What if your next real estate deal could help you eliminate capital gains taxes—while building a thriving short-term rental business? In this episode, tax strategist Ashley Tison dives into the powerful world of Opportunity Zones and how investors can use them to unlock huge tax advantages. These zones aren't just dist

33 min
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