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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