From Fired to 31 Short-Term Rentals - MyBrokerMatt’s FULL Playbook | Matt McCall-Stillman

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00:00 – From Corporate Burnout to Real Estate
03:25 – Scaling Up: Lessons from 50+ Properties
05:28 – The Power of Mindset and Personality Tests
09:02 – Making the Leap: Skills That Transfer
12:00 – Fired, Whistleblowing, and Finding Purpose
15:42 – Fulfillment, Family, and Coaching
18:47 – What Makes a Great Coach?
24:21 – Today’s Short-Term Rental Market
27:29 – Seasonality and Revenue Management
32:39 – Local vs. Remote Investing
37:01 – Advice for First-Time Investors
41:21 – Legal Advice for Investors

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 - ⁠⁠⁠  / mybrokermatt⁠  
Instagram - ⁠⁠  / ⁠  
Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://go.thestrlegend.com/mastermind⁠


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#PropertyInvesting #STRStrategy #OffMarketDeals #AirbnbTips #RealEstateCoaching #PassiveIncome #PropertyManagement



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