From Rejected Athlete to $66B CEO – Kyle Matthews | Ep. 197

Founder's Story

Kyle Matthews shares how getting “cut” from a dream career in professional sports ultimately led him to founding the largest privately held commercial real estate brokerage firm in the U.S. With over 1,000 employees, 25 offices, and $66B in sales volume since 2015, his journey is a masterclass in grit, sacrifice, and long-game leadership.

💡 Topics Covered:

• The moment football ended—and real estate began
• From solo agent to building a $66B empire
• Mental vs. financial freedom as a founder
• Why “ignorance is bliss” was his best advantage
• Hiring, scaling, and leading 1,000+ people
• His obsession with mental toughness (and Kobe Bryant)
• Balancing CEO life with being a father of four
• The real cost of freedom no one talks about
• Why his last name on the company raised the stakes

🔥 Notable Quotes:

"When I started, I thought I was just building a small boutique. It became a monster."

"If I can do it, you can do it. It’s not brilliance—it’s mental toughness."

"Freedom comes at a price. You might get financial freedom, but you’ll lose mental freedom first."

📲 Follow Kyle Matthews:

Instagram & X: @kylematthewsceo

Website: Matthews.com

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