A Life Well-Lived: CAPT Jim DiMatteo

A decorated U.S. Navy veteran and global aviation leader, CAPT Jim DiMatteo shares how legacy, leadership, and a love of flight have shaped a life well-lived.

A Life Well-Lived, the podcast from Exclusive Resorts, shines a light on the extraordinary lives of its Members and friends of The Club — visionaries, leaders, creators, and adventurers who embody what it means to live with intention. Each episode invites listeners into conversations that uncover the values, passions, and stories that shape a life well-lived. Whether from the cockpit, the studio, the boardroom, or beyond, these are the people redefining luxury, not by what they have, but by how they live.

Stories from a man who’s led with clarity at 40,000 feet

What Captain Jim learned in the skies — and at the dinner table — from a fellow Top Gun

A Life Well-Lived: CAPT Jim DiMatteo

In this episode, we meet CAPT Jim “Guido” DiMatteo — a Club Member for 20+ years, decorated U.S. Navy veteran, and globally recognized figure in aviation. With a career spanning nearly three decades as a Naval Aviator, Jim has flown elite fighter jets, led top squadrons, and served as Director of the Navy’s High-Performance Aircraft Division. But what sets him apart isn’t just his service record — it’s his unshakable commitment to excellence, legacy, and purpose.

The conversation takes us from Jim’s early influences — particularly the inspiration of his late father, a fellow Naval Aviator — to the values that have guided his career and personal life. He reflects on what it means to lead with integrity, perform under pressure, and push limits with humility and grit. Whether commanding a squadron or spending time with family, Jim approaches each chapter of life with the same bold energy and deep sense of gratitude. From his role in organizing global aviation events like the Red Bull Air Races to the quiet pride he takes in mentoring the next generation, Jim’s story is a reminder that living well isn’t about status — it’s about showing up with purpose.

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