It turns out that the VC business might be a bit more intense than it looks from the outside.
Doug Leone, the legendary venture capitalist and longtime Sequoia Capital partner, has revealed that he once underwent a root canal without Novocaine — apparently as part of a lifelong personal mission to confront his fears head-on.
Leone says fear has been a recurring challenge throughout his life, but instead of avoiding it, he has made a habit of deliberately putting himself in situations that force him to overcome it.
“Throughout my life, I felt an awful lots of fear, and it’s always been the challenge in front of me,” he said on a podcast. “I was afraid of public speaking. I made sure I became the very best. I was afraid of heights. I worked on sailboats. I made sure I was up ninety-six foot masts. That whenever I feel it, I face it head on.”
For Leone, confronting fear appears to have become something of a personal challenge. And perhaps nowhere was that philosophy tested more literally than during a visit to the dentist.
“It’s almost a challenge. Look, there’s a story that my partners know. I had to get a tooth removed. I actually drilled a tooth drilled for a root canal. And I had to go to a meeting right after that, and I told the dentist, ‘Drill without any Novocaine.’ And he says, ‘You’re out of your mind.’ And my whole life, I wanted to see if I was a badass or not.”
Leone says the experience was partly an attempt to test whether his outward image of toughness was real.
“In other words, am I a fake badass that’s has this envelope nobody could tell or I’m, or am I really a badass on the inside? And I told the dentist, ‘Take it out with no Novocaine.’ And he drilled, and I jumped. And I told the dentist, ‘I won’t move again.’ And I didn’t move again.”
To get through the pain, Leone says he put the experience into perspective, imagining the far greater suffering endured by people in war.
“And I used the trick of thinking what it must be like to go to war and lose an arm or two legs. That’s pain with consequences. Mine was pain with no consequences. And so I just said, ‘It’s just nerve endings from there to my spine to my brain. Fuck it, I’m not moving.’”
The strategy worked — at least technically. Leone says he managed to remain still for the rest of the procedure, though the physical toll was evident afterwards.
“Now, I had to go home and change my shirt ’cause I was a puddle of sweat—but I didn’t move.”
For Leone, however, the point wasn’t dental endurance. It was another opportunity to turn fear into something useful.
“And so I love fear. It does wonders for me. It gives me the challenge to overcome that gives me then a sense of security.”
It’s an unusually visceral philosophy for a venture capitalist, but perhaps one that has served Leone well in an industry built around uncertainty, enormous financial risks, and decisions where conviction often has to overcome fear. For Leone, it seems, whether the challenge is standing before an audience, climbing a 96-foot mast, or sitting in a dentist’s chair without anesthesia, the response remains the same: face it head-on.