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!
Show episodes
What does it really take to break free from the 9-to-5 and build a thriving short-term rental business? In this episode, We sit down with Jake Martin, a former corporate professional who left the security of his W2 job to chase a different kind of success—one built on freedom, flexibility, and financial independence. J
Traveling the World With Kids While Running Rentals? It's Possible! (Here's How) | Adrienne Green
What if you could run a thriving real estate business from anywhere in the world—without ever setting foot in most of your properties? In this episode, we sit down with Adrienne Green, a savvy real estate investor who turned house hacking into a passport for full-time travel with her family. She shares how she built ro
What does it take to turn a remote West Texas ghost town into an Instagram-worthy short-term rental experience? In this episode, discover how a former NYC creative director brought his branding expertise to the desert to create the cinematic Ghost Town Casitas. Learn how storytelling, design, and photography come toget
How a Tech Sales Guy Built an Airbnb Business on Cape Cod (Unfiltered) | Matt Cutler
Ever wondered what it really takes to leave your 9–5 and build a successful short-term rental business on Cape Cod? 🌊🏡 In this episode, we sit down with Matt Cutler, who made the bold leap from a traditional W2 career to creating a thriving STR operation in one of New England’s most iconic vacation destinations. Matt
From Fired to 31 Short-Term Rentals - MyBrokerMatt’s FULL Playbook | Matt McCall-Stillman
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
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
