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Billionaire venture capitalist Doug Leone once took an extreme step: he agreed to undergo a root canal without Novocaine, deliberately putting himself through an excruciating procedure to find out whether he was really a “badass.”

The 69-year-old chairman of Sequoia Capital revealed that he needed to have a tooth treated before an important meeting — and insisted that his stunned dentist perform the procedure without any anesthesia whatsoever.

“All my life, I wanted to know whether I was really a badass,” the investor admitted during an interview on David Senra’s podcast. “In other words, am I a fake badass, with nothing underneath the mask, or am I actually strong on the inside?”

The bizarre experiment was a striking reflection of the way Leone, whose fortune Forbes estimates at $11.8 billion, has used fear as a tool throughout nearly four decades at one of Silicon Valley’s most influential venture capital firms.

“Drill it without any Novocaine,” Leone recalled telling his dentist.

“You’re out of your mind,” the dentist replied.

The unfamiliar sensation of the drill made Leone flinch. But he then promised both himself and his dentist that he would not move again — and he kept his word.

To endure the pain, Leone used a psychological trick: he imagined the suffering of soldiers who had been seriously wounded in battle.

“I thought about what it would be like to go to war and lose an arm or both legs,” the billionaire explained. “That’s pain with consequences. My pain had no consequences.”

He then focused on the sheer physiology of what was happening.

“It’s just nerve endings running from the tooth to the spine and the brain. To hell with it — I’m not moving,” he recalled.

The procedure nevertheless took a physical toll.

“I had to drive home and change clothes because I was drenched in sweat, but I didn’t move,” Leone said.

The Psychology of Fear

Such extreme tests are part of Leone’s personal philosophy. The investor says he has what he describes as a “love affair with fear.” In the past, he has deliberately pushed himself to overcome his fear of heights and his anxiety about public speaking.

“I love fear,” Leone said. “It does wonders for me. It challenges me, and overcoming that challenge gives me a sense of security.”

That hard-edged mentality helped Leone build his career at Sequoia Capital, where he joined in 1988, became a partner in 1993 and eventually rose to lead the firm.

Born in Genoa and immigrating to the United States at the age of 11, Leone helped transform Sequoia into a global investment powerhouse, expanding its presence in China and India. He stepped away from active leadership of the firm in 2022.

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