Billionaire venture capitalist Doug Leone once put himself through an extraordinary test of pain tolerance: he underwent a root canal without Novocaine.
The 69-year-old Sequoia Capital chairman recalled the experience during a lengthy interview with podcaster David Senra. Leone said he needed the dental procedure before an important meeting but specifically instructed his dentist to skip the anesthetic.
“My whole life I wanted to see if I was a badass or not,” Leone said.
He wanted to find out whether his reputation for toughness was merely an outward image or whether he could genuinely withstand extreme discomfort.
“In other words, I’m a fake badass that has this envelope nobody could tell, or am I really a badass on the inside?” he explained.
His Dentist Was Shocked
Leone’s dentist reportedly could hardly believe the request.
“You’re out of your mind,” the dentist replied, according to Leone.
The drill initially caused Leone to jump. But he immediately told the dentist that he would not move again — and said he kept his promise.
Despite the intense pain, Leone remained still throughout the procedure.
How He Managed the Pain
Leone said he tried to put the experience into perspective by imagining the suffering endured by soldiers who had been severely wounded in combat.
The comparison helped him mentally push through the pain.
The experience was so intense that Leone said he was drenched in sweat by the time it was over.
“Now I had to go home and change my shirt because I was a puddle of sweat, but I didn’t move,” Leone recalled.
Why Root Canals Usually Require Anesthesia
Root canals are typically performed using local anesthesia because the pulp inside a tooth contains nerves, blood vessels and connective tissue.
During the procedure, a dentist creates an opening in the tooth and removes inflamed or infected pulp. The area is then cleaned before the canals are filled and sealed.
Local anesthetic temporarily blocks pain signals from traveling through the nerves, allowing the procedure to be performed with significantly less discomfort.
A Personal Test of Fear
For Leone, however, the root canal was never simply about dental treatment.
He described it as an extreme personal experiment designed to answer a question he had apparently carried for much of his life: was he actually as tough as he believed?
With a fortune estimated at around $11.8 billion and a career spanning nearly four decades in Silicon Valley venture capital, Leone has spent much of his professional life dealing with uncertainty, risk and high-pressure decisions.
The painful dental episode offers an unusual glimpse into the mindset he says has helped him confront fear throughout his career.
Rather than avoiding discomfort, Leone deliberately stepped into it — just to see how much he could take.
