Billionaire VC Doug Leone Skips Novocaine for Root Canal

Sequoia Capital chairman Doug Leone recently revealed he underwent a root canal without any anesthetic, simply because he didn’t want to risk being late for a business meeting. The 69-year-old billionaire investor shared the story during a conversation with podcaster David Senra, explaining that he asked his dentist to skip the novocaine entirely so the numbing effects wouldn’t slow him down afterward.

Testing His Own Limits

Leone told Senra he’s spent much of his life wanting to know whether he could handle real discomfort. When he instructed his dentist to proceed without pain medication, the dentist reportedly told him he was crazy. During the procedure, Leone said he flinched once before forcing himself to stay still, mentally comparing his situation to a soldier wounded in battle — reasoning that his own pain carried no real stakes by comparison. He made it through the drilling, attended his meeting on schedule, and only afterward changed out of a shirt soaked with sweat.

From Immigrant Roots to Sequoia’s Top Ranks

Leone’s tolerance for discomfort mirrors the trajectory of his career. Born in Genoa, Italy, he moved to Mount Vernon, New York, at age 11 and went on to earn degrees from Cornell, Columbia, and MIT. He joined Sequoia Capital in 1988, became a partner in 1993, and later rose to managing partner, a role in which he helped grow the firm’s presence in China and India. He stepped back from senior leadership in 2022. Forbes currently estimates his net worth at $11.7 billion.

Reflecting on his mindset, Leone said fear has always driven him rather than held him back, describing an almost lifelong pursuit of pressure-testing his own nerve.