In this episode of Founder2Founder, Aaron Spivak sits down with Kyle Matthews, the Founder and CEO of Matthews™, one of the fastest-growing and now largest privately held commercial real estate brokerages in the U.S. Since launching the firm in 2015, Kyle has scaled the company to nearly 30 offices and over 1,000 employees, closing more than $66 billion in transaction volume. Before his rise in business, Kyle played college football at USC under Pete Carroll, learning firsthand what it meant to be part of a high-performance team, lessons that deeply shaped his leadership style and company culture.

Kyle opens up about the long, uncertain road of early entrepreneurship, including the 17 months he went without earning a single dollar in commission. He shares how the pain of regret from his football days shaped a new personal standard of work ethic and intensity in business. Kyle gets honest about what it really takes to succeed as a founder, the role of a supportive partner, why he front-loaded his life for freedom later, and how he's intentionally designed both business and family life to thrive. This conversation is packed with insights on scaling, sacrifice, and staying grounded.

Chapters:
03:51 – From Football Benchwarmer to Business Beast
05:24 – Lessons From Team Sports That Shaped Leadership
06:45 – The Regret That Still Fuels Kyle Today
08:32 – Building a Career With No Plan B
10:02 – How Waking Up at 4:45 Became a Competitive Advantage
12:41 – 14-Hour Workdays for 10 Years Straight
14:21 – 17 Months Without a Paycheck and Why He Didn't Quit
18:33 – When Hard Work Didn’t Translate to Results, Yet
20:15 – How Early Struggles Made His Boss's Job Harder
21:10 – The Real Impact of Marrying Young
24:48 – The Secret to Aligned Relationships While Scaling
27:01 – Would He Be as Successful Without His Wife?
31:41 – Designing His Life to Be Fully Present for His Kids
33:17 – How NFL Players Actually Spend Their Time
34:45 – His Dad's Role Model Blueprint for Fatherhood
36:59 – Coaching His Son’s Football Team While Running a Company
38:30 – Why Your 20s Shouldn’t Be Spent “Enjoying Life”
40:00 – The Myth of Work-Life Balance
42:02 – How Matthews™ Scaled From 15 People to 1,000+
45:23 – Why Kyle Left a Public Company to Start His Own
46:45 – The Business Model That Made Matthews™ Explode
52:47 – Scaling as a CEO: From Founder to Strategic Leader
54:36 – The Intuition Trap: When Founders Need to Let Go
59:08 – What Kyle Would Tell His 33-Year-Old Self
1:03:29 – Buying Matthews.com From a Basement-Dwelling Domain Squatter
1:06:13 – Why You Must Choose Your Hard in Life

Links:
https://www.matthews.com
IG: @kylematthewsceo
LinkedIn: Kyle Matthews
YouTube: Kyle Matthews
Podcast: The Matthews Me

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