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

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:

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.

“I slept in my car for a week. I showered at 3000 Sand Hill Road. I was down to no money,” he said, before adding that he wasn’t particularly scared: “My future earnings were going to be terrific. So, I wasn’t panicked — I just knew it was only an inconvenience.”

That mindset has defined a career that’s now in what could be a final act. Leone worked at Sequoia Capital from 1988 to 2022, rising through the ranks to eventually become managing partner. Toward the end of that tenure, he partnered with the first Trump administration on a task force to reopen the US economy following the COVID-19 lockdowns. He stepped down in 2022 at age 65 — but rejoined this past March, amid renewed excitement over AI investing.

Back at the firm, Leone says the fast-paced AI frontier still motivates him through fear — and he’s leaning into that, too. He calls himself a “low-level analyst” who must “prove myself” to stay relevant.

“If nine months from now, which is one year since I returned, I feel just as irrelevant, I’m going to take myself,” he said. “I don’t know if I can do it again. And so, therein lies the fun.”