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Wheels Up: Why So Many CEOs Become Pilots

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06.08.2026

Wheels Up: Why So Many CEOs Become Pilots

Founders’ newest status symbol? Getting a pilot’s license to fly their own plane

After graduating from high school in 2000, David Spector spent the summer working construction for his uncle in Maryland. He spent his earnings on a secret vice: flying lessons in a two-seat Cessna 152. But the dream didn’t last. “My parents caught me lying about where I’d go after work,” he recalls.

Spector went on to earn degrees from Tulane and then Sloan, after which he made partner at Sequoia Capital. He quit Sequoia, and he and his wife launched the intimate apparel brand Thirdlove, which has generated an estimated $1 billion in revenue since its inception. He then pivoted to launch Nanotrace, an oncology........

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