The first time I "meet" CAPT Jim DiMatteo is from his cockpit. During a video greeting to Exclusive Resorts while cruising over Lake Tahoe in an F-5 Advanced Tiger, DiMatteo’s passion for aviation, and life in general, is readily apparent. “Thank you for all you do to make my family’s life better!” he exclaims in flight with a grin, all the while calmly performing an aileron roll over Tahoe’s North Star area. The second time I spoke with him, from his home in San Diego, his enthusiasm was equally elevated.
Jim DiMatteo, who in 2018 was inducted into the Aviation Hall of Fame for his Lifetime Achievements in Aviation, has an innate ability to foster top-of-class talent—his own and his many TOPGUN mentees. And whether helping out on the Top Gun: Maverick sequel, traveling with family to favorite Club destinations, or motivating staff at one of his California restaurants, CAPT DiMatteo is all-in, all the time.
His CV highlights are about as Type A as it gets: 5,500 hours in five different fighter aircraft (F/A-18, F-16, F-14, F-5, A-4) in over 25 years of service; Commanding Officer of both VFC-13 and VFC-111 (the TOPGUN Adversary squadrons on each coast); Commander, Naval Air Forces (CNAF) staff overseeing the TOPGUN Adversary program; the only US Race Director for the International Red Bull Air Races; Director of the Breitling Jet Team American Tour; owner and operator of award-winning San Diego restaurants and bars. Plus, his passion for travel is impressive, too — he’s visited 50 countries and counting. As such, the question quickly arises: How do you do it all successfully?
“We have a culture at TOPGUN that’s called the debrief culture,” CAPT DiMatteo says. “Which means we’re going to go out and fly, do the best we can, and then come back and, ad nauseam, debrief the flight and say, ‘What area can I improve on?’”
Debrief culture has fueled DiMatteo’s success from an early age. Both his father and brother were Naval Aviators, and though he didn’t feel pressured to follow in their footsteps, he graduated University of California, Berkeley, and did just that, learning from their journeys while building an unprecedented naval aviation career. In tandem, he also built a family with his wife, Kathy, and their two children, applying what he learned during his own career to all aspects of life.
“Getting into TOPGUN is like going to the World Series,” he explains. “A big part of our relentless pursuit of excellence is our debrief culture. It can be applied to any company, business, social challenge, or personal relationship. If you keep things in and don’t talk about them, then how do you improve? How do you not make that same mistake the next day?”
As a Club Member of 18 years, CAPT DiMatteo has noticed a similar ethos at Exclusive Resorts. “When I first met Exclusive Resorts CEO James Henderson at an event, I explained that one of the things I really liked about the Club was that they tend to have the same debrief culture: I come back from a weekend vacation, wherever it may be, and I immediately get an email asking, ‘How was everything? How can we improve?’ And they engage in feedback.”
He’s also quick to claim his own mistakes and use them to teach others. “As a leader, I always felt it very effective to start anything off with identifying my own mistakes.” His astonishing trajectory has not come without cost; his voice lowers when recalling the 50-plus friends lost to training and combat. As a fighter pilot, he explains, “There’s plenty of times, especially after having kids, that you sit in your bed at night and go, ‘Whoa, that was a close call.’”
Navigating close calls, however, is his continued legacy. And whether in simulated combat or helping out Tom Cruise on the set of the Top Gun: Maverick sequel, ultimately, CAPT DiMatteo strives to pay it forward. “From a teacher or parent perspective, to see the happiness and growth of another person is much more rewarding than my own personal achievement. My approach in life is I’d rather try and fail at something than not try at all and regret it later.”