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!
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!
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 the short-term rental world.
We dive into Matt’s journey—how he went from corporate burnout to STR powerhouse—and unpack the mindset shifts, calculated risks, and coaching that helped him scale. Along the way, we explore market trends, legal must-knows for investors, and why having local knowledge and legal support can make or break your success.
Whether you're managing your first listing or looking to grow your portfolio, this episode is full of raw insight, practical advice, and stories that will inspire and inform your next move.
👉 Don't forget to like, subscribe, and hit the bell for more STR success stories and tips!
Things we discussed in this episode:
From Corporate to Real Estate: Matt's Bold Career Shift
Why Mindset Matters in Entrepreneurship
How Matt Scaled to 50+ Properties
The Real Value of a Great Coach in Real Estate
STR Market Trends: Design, Amenities & Regulations
Seasonality & Revenue Strategy in Short-Term Rentals
Local vs. Remote Investing: What Works Best?
Lessons Learned from Hotel Ownership
Legal Must-Knows for STR Investors
Top Advice for First-Time STR Buyers
Get in touch with Matt:
Facebook - https://www.facebook.com/MyBrokerMatt
Instagram - https://www.linkedin.com/in/mybrokermatt/
Website - https://go.thestrlegend.com/mastermind
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbInvestment #RealEstateSuccess #PropertyInvesting #STRStrategy #OffMarketDeals #AirbnbTips #RealEstateCoaching #PassiveIncome #PropertyManagement
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Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first episode of SmartStay Show!
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SmartStay Show Website and on Instagram and YouTube
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Straightforward Short-Term Rentals Website and on Instagram
Attorney Rory Gill on LinkedIn
Jason Muth on LinkedIn