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

EPISODE · Apr 8, 2025 · 28 MIN

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

from Founder's Story · host IBH Media

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 beganFrom solo agent to building a $66B empireMental vs. financial freedom as a founderWhy “ignorance is bliss” was his best advantageHiring, scaling, and leading 1,000+ peopleHis obsession with mental toughness (and Kobe Bryant)Balancing CEO life with being a father of fourThe real cost of freedom no one talks aboutWhy 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: @kylematthewsceoWebsite: Matthews.comOur Sponsors:* Check out Indeed: https://indeed.com/FOUNDERSSTORY* Check out Northwest Registered Agent and use my code FOUNDERS for a great deal: https://northwestregisteredagent.com* Check out Plus500: https://plus500.com* Check out Rosetta Stone and use my code TODAY for a great deal: https://www.rosettastone.com Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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 beganFrom solo agent to building a $66B empireMental vs. financial freedom as a founderWhy “ignorance is bliss” was his best advantageHiring, scaling, and leading 1,000+ peopleHis obsession with mental toughness (and Kobe Bryant)Balancing CEO life with being a father of fourThe real cost of freedom no one talks aboutWhy 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: @kylematthewsceoWebsite: Matthews.comOur Sponsors:* Check out Indeed: https://indeed.com/FOUNDERSSTORY* Check out Northwest Registered Agent and use my code FOUNDERS for a great deal: https://northwestregisteredagent.com* Check out Plus500: https://plus500.com* Check out Rosetta Stone and use my code TODAY for a great deal: https://www.rosettastone.com

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

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This episode is 28 minutes long.

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This episode was published on April 8, 2025.

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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...

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