Legends of Culture brings you inside real conversations with the leaders shaping today’s workplaces.
Each episode dives into the stories, decisions, and defining moments behind strong cultures and high-performing teams. From lessons learned to forward-thinking perspectives, we go beyond surface-level insights to uncover what it actually takes to build, lead, and evolve in today’s world of work.
Whether you're growing a team, leading an organization, or rethinking how culture shows up in your business, Legends of Culture is built for those who want to lead with intention and create something that lasts.
For nearly 20 years, Matthew Irwin has helped shape one of America's most iconic brands. In this episode of Legends of Culture, Jared Oakes sits down with Matthew, Vice President and Deputy General Counsel of Gap Inc., to explore the leadership lessons that have guided his career and why authentic relationships remain at the center of great organizational cultures.
14 Jul 2026
How Culture Gets Shook
From intern to CEO, Chris Halapy has spent nearly 30 years growing alongside Shook Construction. In this episode of Legends of Culture, he joins Jared Oakes to discuss how strong values, intentional leadership and a commitment to people have helped build a culture that has endured for generations. Chris also shares why culture requires constant attention—and why leaders must model the behaviors they expect from others.
16 Jun 2026
The Culture-Building Mindset
What does it take to build a culture of relentless effort and high performance in commercial real estate? In this episode, 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. 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.
13 May 2026
The Whole Truth About Workplace Culture
What does it take to build a culture of excellence in healthcare? In this episode of Legends of Culture, Jared sits down with Dr. Ryan Molli, founder and CEO of Whole Health Orthopedic Institute, to explore how vision, authenticity and relentless commitment shape organizational culture from the ground up. Drawing on his journey from rural Pennsylvania to launching his own practice, Dr. Molli shares how his upbringing, sports background and entrepreneurial spirit have influenced his approach to leadership and team-building.
14 Apr 2026
How Culture Heats Up
What’s culture like in the NBA? In this episode of Legends of Culture, host Jared Oakes sits down with Michael McCullough, Executive Vice President and Chief Marketing Officer of the Miami HEAT, widely regarded as the “brand architect” behind the team’s dynamic culture. With more than 35 years of experience in sports marketing and fan engagement, Michael shares how he’s built and sustained a strong organizational culture, from launching new initiatives and fostering buy-in to creating meaningful connections between players, staff and the community. He offers a behind-the-scenes look at leading a high-profile franchise, collaborating with superstar athletes and driving impact through innovative partnerships. Tune in to learn how intentional culture-building and authentic leadership can elevate an organization and inspire everyone involved.
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