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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Hey, everyone. Welcome back to Founders Story. Today, we have Kyle Matthews. And Kyle, you are the founder and CEO of Matthews Real Estate Investment Services, the largest privately held commercial real estate brokerage in the US, 25 offices, 1,000 plus agents and employees, and over 7,000 66 billion in sales volume since 2015.
I know you're going to give us some incredible tips and strategies of the success you've had, the learnings, but we got to go back in time because you have a very interesting past around a family of professional athletes. But yeah, you took a different approach. You took a different path.
So let's go back to the time when you were in college, you were playing, the possibility of you maybe being a professional before you even thought about real estate. How did this transition happen?
Yeah, no, first of all, I appreciate you having me on, Daniel. And I love how you say I took a different path. It almost makes it sound like it was a strategic choice of mine. Unfortunately, that wasn't how it all played out. I was playing football at USC about 20 years ago when We were winning a lot of games. We won national championships when I was there.
We had a great coach in Pete Carroll and some amazing teammates and players that went on to the NFL. Unfortunately, I wasn't one of those players. I didn't have that. There's levels to every game, and there's certainly levels to football, and I didn't have that last level. But it's not something you really realize early on. It was at the very end of my four years at school.
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