Sequoia's Doug Leone says he got a tooth removed without Novocaine to attend a meeting

Doug Leone says he's motivated by fear.

Steve Jennings/Getty Images for TechCrunch Doug Leone shared a story about a no-Novocaine dental procedure.

The Sequoia Capital partner told Business Insider it was because of his meeting schedule.

"I thought, 'Now I will find out whether I am a badass or not.'" Some people take a coffee before a big meeting.

VC Doug Leone said he once took a Novocaine-less tooth removal.

During an interview on the "David Senra" podcast, released on Sunday, Leone, one of Sequoia Capital's best-known partners, said he skipped the numbing agent during a dental drilling procedure.

"I told the dentist, 'Drill without any Novocaine,' and he says, 'You're out of your mind,'" he said.

"My whole life, I wanted to see if I was a badass or not." In an email with Business Insider, Leone clarified that his decision had a practical motive: He had a meeting after, and the dentist told him Novocaine might make him sound or look funny.

"That's when I thought, 'Now I will find out whether I am a badass or not,'" he wrote.

It's the kind of story Leone tells often, he said on the podcast, because it's an example of how some of his most consequential moves have been motivated by fear rather than ambition.

Each career shift, he said, wasn't inspired by a "vision of greatness," but a "deep and secure need to remain relevant." "I love fear," he said.

"It does wonders for me.

It gives me the challenge to overcome that gives me then a sense of security." Now, clips of his description of the pain-embracing dental trip have made the rounds on the internet.

People are giving him the Chuck Norris treatment: imagine telling Doug Leone you’re going to be ooo for a long weekend https://t.co/LpLp0xa4TG — Tyler Matheson (@tymatheso) August 30, 2026 When Doug Leone slices onions, the onions cry. https://t.co/6KdO9LFaIT — Peter Sellis (@petersellis) August 30, 2026 During the interview, Leone also said that when he became a partner at the firm in 1993, he was homeless after a divorce left him with only an allowance for a monthly car note.