Billionaire venture capitalist Doug Leone has shared an unusual story from his past: he once went through a routine root canal without anesthesia simply “to see” whether he could endure it.
Leone, 69, the chair and partner at Sequoia Capital, made the admission Sunday during an appearance with David Senra, who also hosts the popular Founders podcast.
He joined Senra on the set of his new long-form interview show, which features conversations with entrepreneurs regarded as “extreme winners” in their fields.
Leone has built a fortune of more than $12 billion across roughly four decades of investing in Silicon Valley.
The striking anecdote came after Senra asked Leone about his relationship with fear and how he has learned to confront it.
“Throughout my life, I’ve felt an awful lot of fear, and it’s always been the challenge in front of me,” Leone said.
He explained that he deliberately pushed himself to overcome more common fears early in life, including heights and speaking in public.
Then came a painful dental problem that required drilling before an important meeting — and, as Leone recalled, presented an entirely different test of willpower.
Sequoia Capital chairman and partner Doug Leone, 69, described undergoing a routine root canal without anesthesia during a podcast appearance on
He recalled telling the dentist: ‘Drill without any Novocaine,’ as well as the doctor’s curt reply, ‘You’re out of your mind.’
But Leone, an Italian immigrant who grew up in a working class family, wasn’t listening.
‘My whole life, I wanted to see if I was a badass or not,’ he said with a smile.
It took another back-and-forth for the doctor to finally listen and begin drilling as commanded, Leone told Senra.
‘And I jumped,’ the veteran venture capitalist remembered, but promised the dentist he wouldn’t do so again.
‘And I didn’t,’ Leone said proudly.
He said he dealt with the pain by thinking of the pain people wounded in war go through.
‘That’s pain, with consequences. Mine was pain with no consequences,’ Leone said.
He made the admission to David Senra on Sunday. Senra owns and operates the popular Founders podcast
He remembered telling himself: ‘It’s just nerve-endings, from my spine to my brain. F*** it, I’m not moving.’
‘Now, I had to go home and change my shirt, because I was a puddle of sweat, but I didn’t move,’ he went on to admit.
Leone concluded that he ‘love[d] fear’ and that dealing with the emotion has helped him become the success he is today.
‘It does wonders for me – it gives me the challenge to overcome, and it gives me then a sense of security,’ he concluded.
He was named the chair of Sequoia Capital – one of the country’s most storied venture capital firms – this year, after more than three decades with the company.
Senra, meanwhile, was left speechless. He shared the exchange on X, where reception was mixed.
One user remarked: ‘[Not going to lie] if i make it to partner, this is exactly the kinda stuff I’d be throwing around.’
Someone else joked: ‘Next week a sh**load of dentists in the Bay Area are going to be wondering “Why the f**k are all these dorks asking to skip the novocaine?”‘
Several others mocked the mindset for bearing purported stereotypes associated with money-minded magnates.
Senra launched Founders with the mission of offering viewers a glimpse at some of the US’s most enterprising minds in 2016.
He billed his new show as this generation’s ‘Charlie Rose’ in an interview with Fortune last month. He touted powerful CEOs like Jeff Bezos, Beats By Dre’s Jimmy Iovine, and Spotify’s Daniel Ek at the time.
‘Where do elite people in the world go – especially in business – to have intelligent conversations multiple times a week? That’s what I’m trying to build,’ Senra said. He has nearly half a million subscribers on YouTube, as of writing.
