Doug Leone, the chairman of venture capital firm Sequoia Capital, recounted undergoing a root canal procedure without Novocaine as a deliberate test of his own resilience. Leone, whose net worth is estimated by Forbes at $11.8 billion, described the experience in a recent interview with podcaster David Senra, explaining he wanted to determine if he was genuinely tough or merely projecting an image of strength.
"My whole life I wanted to see if I was a badass or not," Leone, 69, said in the interview, which 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?"
Leone recalled instructing his dentist to proceed with the drilling without any anesthetic, a request that was met with disbelief. "You’re out of your mind," the dentist reportedly replied. Initially, the drilling caused Leone to flinch, but he then resolved to remain still, a promise he kept.
To cope with the pain, Leone said he mentally compared his situation to that of soldiers experiencing severe combat injuries. "I used the trick of thinking what it must be like to go to war and lose an arm or two legs," he said. "That’s pain with consequences. Mine was pain with no consequences." He also focused on the physiological aspects, telling himself, "It’s just nerve endings from there to my spine to my brain. F–k it, I’m not moving."
The procedure left him drenched in sweat, prompting him to change his shirt afterward, though he maintained his resolve not to move. Root canals typically involve removing inflamed or infected pulp from a tooth's center and are usually performed with local anesthesia to block pain signals. The American Association of Endodontists notes that with modern anesthetics, root canals are generally no more painful than receiving a dental filling.
Leone described this incident as an extreme manifestation of his lifelong engagement with fear, which he stated has been a driving force in his career. He mentioned that he also confronts fears such as heights and public speaking, viewing them as challenges that provide a sense of security upon overcoming them. "I love fear. It does wonders for me. It gives me the challenge to overcome that gives me then a sense of security," he said.
Leone joined Sequoia Capital in 1988 and became a partner in 1993, eventually taking over as managing partner in 1996. He helped expand the firm, originally focused on Silicon Valley, into a global investment entity with operations in China and India. Leone stepped down from his senior leadership role in 2022. His investment portfolio includes significant ties to companies such as ServiceNow, RingCentral, Nubank, Rackspace, Medallia, and the cybersecurity firm Wiz, which was acquired by Google for $32 billion in cash in March.