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.
What this episode covers
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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