Billionaire venture capitalist Doug Leone once underwent a root canal without Novocaine — deliberately putting himself through the excruciating procedure to find out whether he was really a “badass.”
The 69-year-old Sequoia Capital chairman said he had to get the dental work done before heading to a meeting — and ordered his incredulous dentist to skip the anesthetic.
“My whole life I wanted to see if I was a badass or not,” the exec said during a lengthy interview with podcaster David Senra that was released online over the weekend.
“In other words, I’m a fake badass that has this envelope nobody could tell, or am I really a badass on the inside?”
The bizarre test was an extreme example of how Leone — whose fortune Forbes puts at around $11.8 billion — says he has harnessed fear throughout a career spanning nearly four decades at one of Silicon Valley’s most powerful venture-capital firms.
“Drill without any Novocaine,” Leone recalled telling the dentist, without specifying when the painful session took place.
“You’re out of your mind,” the tooth doctor replied, according to Leone.
The drill initially caused Leone to jump.
He then told the dentist he would not move again — and said he kept his word.
To endure the pain, Leone said he tried to put his ordeal in perspective by imagining the suffering of soldiers grievously wounded in combat.
“I used the trick of thinking what it must be like to go to war and lose an arm or two legs,” Leone said. “That’s pain with consequences. Mine was pain with no consequences.”
He then focused on the physical mechanics of what he was experiencing.
“It’s just nerve endings from there to my spine to my brain,” Leone recalled telling himself. “F–k it, I’m not moving.”
The ordeal nevertheless took a physical toll.
“Now I had to go home and change my shirt because I was a puddle of sweat, but I didn’t move,” Leone said.
Root canals are normally performed under local anesthesia because the pulp at the center of a tooth contains nerves, blood vessels and connective tissue.
During the procedure, a dentist drills into the tooth and removes inflamed or infected pulp before cleaning, filling and sealing the canals.
The anesthetic temporarily blocks nerves from transmitting pain signals to the brain, allowing patients to remain awake without feeling the drilling and removal of sensitive tissue.
With modern anesthetics, root canals are generally no more painful than getting a filling, according to the American Association of Endodontists.
The story surfaced as Leone described a lifelong relationship with fear that he said has also included confronting heights and public speaking.
“I love fear,” Leone said.
“It does wonders for me. It gives me the challenge to overcome that gives me then a sense of security.”
That mentality helped fuel his rise at Sequoia, which Leone joined in 1988.
He made partner in 1993 before taking over as managing partner three years later.
The Genoa-born investor immigrated to the US at age 11 and settled with his family in Mount Vernon, NY, before earning degrees from Cornell University, Columbia University and MIT and working in technology sales.
Leone went on to help transform Sequoia from a Silicon Valley-focused venture firm into a global investing powerhouse, including leading its expansion into China and India.
He remained at the top of the firm until stepping aside from its senior leadership role in 2022.
His investment record includes ties to ServiceNow, RingCentral, Nubank, Rackspace, Medallia and cybersecurity giant Wiz, which Google acquired for $32 billion in cash in March.