Real Estate Success: The Whissel Way

From the Court to Closings: Jason Matthews’ Real Estate Journey


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In this powerful episode, Kyle Whissel sits down with Jason Matthews, a former NCAA basketball star turned real estate investor, to share his journey from humble beginnings in South Central LA to launching a multimillion-dollar luxury short-term rental business in Florida. Jason’s story spans personal transformation, lessons from NBA legends, Wall Street internships, and how showing up led to life-changing opportunities. The episode wraps with practical advice on building wealth through real estate, including his niche strategy of developing FEMA-compliant beach homes. A must-listen for agents looking to scale, pivot, or break into investment real estate.


Chapters:

  1. 00:00 – Intro: From Boardroom to Podcast
  2. 00:55 – Jason’s Humble Beginnings in LA
  3. 02:08 – Late Start, Big Results: Making the League
  4. 04:24 – Thoughts on NIL and Player Empowerment
  5. 07:46 – The Power of Alumni & Brand Exposure
  6. 11:55 – From College Hoops to NBA Tryouts
  7. 17:50 – Jerry West, Magic Johnson, and Life Lessons
  8. 24:12 – Leaving the League for Wall Street
  9. 31:25 – Luxury Short-Term Rentals in Florida
  10. 38:20 – Investing Passively: How Agents Can Get Involved
  11. ...more
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    Real Estate Success: The Whissel WayBy Whissel Realty Group

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