Some people have a cup of coffee before a big meeting. VC Doug Leone said he once had a root canal without novocaine.
During an interview on the “David Senra” podcast released Sunday, Leone, one of Sequoia Capital’s best-known partners, said he skipped the narcotic during a dental drilling procedure.
“I said to the dentist, ‘Drill without novocaine,’ and he says, ‘You’re crazy,’” he said. “All my 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 afterwards and the dentist told him that Novocaine might make him sound or look funny. “Then I thought, ‘Now I’ll find out if I’m a badass or not,’” he wrote.
It’s the kind of story Leone often tells, 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 change, he said, was inspired not by a “vision of greatness” but by a “deep and secure need to stay relevant.”
“I like fear,” he said. “It works wonders for me. It gives me the challenge to overcome and that gives me a sense of security.”
Now clips of his description of the pain-encompassing dental journey are circulating 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 a monthly car note.
“I slept in my car for a week. I took a shower at 3000 Sand Hill Road. I ran out of money,” he said, before adding that he wasn’t particularly scared: “My future earnings were going to be great. So I wasn’t panicking — I just knew it was just an inconvenience.”
That mentality has defined a career that is now in what could be a final act. Leone Worked at Sequoia Capital from 1988 to 2022, where he grew to eventually become managing partner. By the end of that term, he has worked with the first Trump administration on a task force to reopen the U.S. economy after COVID-19 lockdowns. He stepped down in 2022 at the age of 65, but rejoined last March amid renewed excitement over AI investments.
Back at the company, Leone says the fast AI frontier still motivates him through fear – and that’s what he leans on. He calls himself a “low-level analyst” who has to “prove myself” to stay relevant.
“If in nine months, which is a year since I came back, I feel just as irrelevant, then I’m going to take myself,” he said. “I don’t know if I can do it again. And that’s where the fun lies.”
