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 happens when an ICU nurse brings his heart for care into the world of short-term rentals? In this episode, we sit down with Jeremy Rosen, who’s turned his passion for helping people into a thriving business managing over 20 properties—all while still working hospital shifts. He shares how compassion, clear systems
Inside the Midterm Rental Movement (It’s Not Just Traveling Medical Pros) | Katie Lyon
Is the future of hosting all about midterm rentals? In this episode, we chat with Katie Lyon from Furnished Finder to uncover why midterm stays are gaining major traction—and why they’re no longer just for travel nurses. From contractors and relocating families to corporate nomads, a whole new wave of guests is looking
I Bought This 400 sq ft Condo for $1M… Now It Pays for 2 Homes (STR Reality) | Kareem Sanjaghi
Ever wonder how a beachfront condo in Provincetown could become a gold mine? In this episode, we sit down with Kareem Sanjaghi—Prideaway Stays’ very first client—to hear how he went from mortgage officer to full-time musician and savvy real estate investor. Kareem shares the story behind his short-term rental success,
What if one tool could organize your entire short-term rental business—and actually give you your time back? In this episode, we sit down with hospitality veteran turned systems expert Michael Dinwiddie to talk about the real-world challenges of managing short-term rentals and how the right systems can transform your o
Why I Stopped Trusting Airbnb Alone for Last-Minute Bookings (and did THIS) | Alex Alioto
Can Last-Minute Bookings Actually Boost Your STR Revenue? Last-minute bookings aren’t just a backup plan anymore—they’re becoming a key revenue strategy for short-term rental hosts. In this episode, we sit down with Alex Alioto, co-founder of Whimstay, about how shifting traveler behavior—especially among Gen Z and mil
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
