What does it take to build a culture of relentless effort and high performance in commercial real estate? In this episode of Legends of Culture, Jared Oakes sits down with Kyle Matthews, founder, CEO and chairman of Matthews Real Estate Investment Services, to explore how a commitment to effort, discipline and leading from the front has shaped one of the fastest-growing brokerage firms in the country.
Kyle shares how his upbringing in a family of athletes, including his father, NFL linebacker Clay Matthews, instilled in him the value of effort above all else—a lesson that became the foundation of his leadership style and company culture. Jared and Kyle discuss the challenges of starting a business from scratch, the importance of never quitting, and why effort is the ultimate differentiator in both real estate and law.
The conversation dives into how Matthews built a culture of “manic intensity” and excellence—and how understanding each individual’s deeper motivation helps drive performance. Kyle also reflects on the realities of scaling culture as an organization grows and the importance of reinvesting in people and the business. Jared and Kyle also break down why attracting the right talent—and repelling the wrong fit—is key to sustaining success.
Tune in for practical insights on building a high-performing organization where effort, shared purpose and a commitment to excellence are at the heart of the culture.
Kyle Matthews is the Founder, Chairman, and Chief Executive Officer of Matthews™, where he has built a high-performance culture centered on effort, discipline and execution. Since founding the firm in 2015, he has scaled it into one of the fastest-growing commercial real estate platforms in the country, emphasizing a “legends only” mentality and leading from the front. Under his leadership, Matthews™ has grown to more than 30 offices and 1,000+ professionals nationwide while building a culture where success is earned through relentless effort. In addition to his industry achievements, Kyle hosts the Matthews Mentality Podcast, launched in 2023, where he shares insights on business and the evolving commercial real estate landscape.