In this episode of the WPAOG Podcast, host Jamie Enos sits down with Matthew Caldwell, CEO of the NBA’s Minnesota Timberwolves and WNBA’s Minnesota Lynx. Matt brings a unique leadership background shaped by his service as a U.S. Army Captain, his time at Goldman Sachs, and nearly a decade as CEO of the Florida Panthers, where he helped lead the team to back-to-back Stanley Cup championships.

Caldwell, a 2002 graduate of the United States Military Academy at West Point, also earned an MBA from Northwestern Kellogg School of Management and a J.D. from Northwestern University School of Law. He served five years in the U.S. Army, conducting combat operations in Iraq and peacekeeping in Kosovo. His business leadership has been widely recognized, including being named a South Florida Business Journal Ultimate CEO and receiving multiple “Forty under 40” awards. At just 36, he became the youngest CEO in U.S. pro sports when he took the helm of the Florida Panthers in 2016.

This conversation explores the intersection of military discipline, entrepreneurial thinking, and executive leadership. Tune in to hear how Caldwell navigates organizational alignment, builds resilient cultures, and prepares to lead two professional basketball teams into a new era of growth and performance.

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Episode Timestamps:

(01:31) Leadership Lessons from Military to Sports

(03:38) Building from West Point Foundations

(08:24) Mentorship and Support from the Long Gray Line

(09:53) Entrepreneurial Ventures in Sports

(13:05) Advice on Career Pivots and Transitions

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Links:

Connect with Matthew

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