Doug Leone, the 69-year-old billionaire venture capitalist who chairs Sequoia Capital, told his dentist to skip the Novocaine before a root canal and just start drilling. He wanted to see, in his own words, whether he was a badass. By the time the procedure ended, he had jumped once when the drill hit a nerve, promised himself not to move again, and sweated through his shirt so thoroughly that he changed it once he got home.
Leone described the ordeal during an interview with podcaster David Senra, released online over the weekend, as reported by the New York Post. According to Leone, his dentist reacted to the request by telling him, “You're out of your mind.” Leone told Senra he did it anyway, later saying the pain came “with no consequences” and that he endured it by imagining soldiers wounded in combat. He also said fear has been a driving force throughout his career, adding that he loves fear because it gives him “a challenge to overcome and a sense of security.”
Root canals are normally performed under local anesthesia, which temporarily blocks nerves from transmitting pain signals to the brain while a dentist drills into the tooth to remove inflamed or infected pulp — tissue that contains nerves, blood vessels and connective tissue — before cleaning, filling and sealing the canals. Clinical guidance cited by endodontists and dental associations, including material published by Urban Family Dental, holds that modern root canals with anesthesia are designed to be virtually painless, with 95% of patients calling the experience painless or far less painful than expected. That makes an un-anesthetized root canal highly abnormal by contemporary dental standards; the American Association of Endodontists has said modern root canals are generally no more painful than getting a filling, per the Post's reporting.
A Practical Motive Behind the Machismo
The story initially read as pure bravado, but Leone offered a more pragmatic explanation in a follow-up email to Business Insider after his podcast appearance. He said he ordered his dentist to skip the anesthetic because he had an important meeting immediately after the appointment, and his dentist had warned that local anesthesia could temporarily make his face look or sound off — a complication he wanted to avoid walking into a room full of colleagues or founders, according to Business Insider.
That same interview surfaced another episode from Leone's past that helps explain his relationship with fear and hardship. When he made partner at Sequoia Capital in 1993, a divorce left him with virtually no money, and he told Senra he ended up sleeping in his car for a week, showering at Sequoia's office at 3000 Sand Hill Road in Menlo Park. He made managing partner three years later, in 1996, when founder Don Valentine — who started the firm in 1972 — handed leadership to Leone and Michael Moritz.
From Genoa to Sand Hill Road
Leone immigrated to the United States from Genoa, Italy, at age 11 and eventually settled with his family in Mount Vernon, New York. He went on to earn degrees from Cornell University, Columbia University and MIT, then began his technology career in sales before joining Sun Microsystems, the company co-founded by fellow billionaire venture capitalist Vinod Khosla. Leone joined Sequoia Capital in 1988 and worked in technology sales before making the jump into venture investing.
Leone became sole managing partner when Moritz stepped back in 2012 and is credited with helping lead Sequoia's expansion into China and India, transforming the firm from a Silicon Valley-focused venture shop into a global investing powerhouse. He passed global leadership to Roelof Botha in 2022 and stepped aside from Sequoia's senior leadership that year, only to return in March 2026 to a newly created chairman role under co-stewards Alfred Lin and Pat Grady, following Botha's resignation in late 2025, according to Forbes.
A Portfolio Built on Big Exits
Leone's return to active dealmaking followed one of the largest paydays in Sequoia's history. Google parent Alphabet completed its acquisition of cybersecurity startup Wiz — one of Leone's marquee investments — in March 2026 for a headline value of $32 billion in cash, later reported in financial filings at approximately $29.5 billion, Forbes reported. Leone also holds investment ties to Nubank, Rackspace, ServiceNow, RingCentral and Medallia, rounding out a career built on identifying enterprise and fintech winners early.
Forbes ranked Leone No. 8 on its 2026 Midas List of top tech investors, his 21st appearance on the list, estimating his personal net worth at $10.8 billion to $12.2 billion; the Post separately cited a Forbes figure putting his fortune around $11.8 billion. His return comes as Sequoia, under Lin and Grady alongside Leone as chairman, raised $7 billion in April 2026 for a new expansion fund aimed at major artificial intelligence companies including OpenAI, Anthropic and xAI, according to Entrepreneur. Sequoia has also backed a string of high-profile local deals, including a co-led cybersecurity round that pushed Palo Alto's Glow to unicorn status and an investment in the defense tech startup Cathedral, both covered previously by Hoodline.
Beyond the venture world, Leone has also built a political profile. He and his wife donated $100,000 to Donald Trump's 2020 re-election campaign, and in 2024 Leone emerged as a primary financial backer of America PAC, which supported Trump's 2024 presidential campaign, according to information compiled on his Wikipedia profile. For Leone, though, the dental chair story seems to circle back to the same theme that has defined his four-decade career: a willingness to sit with discomfort, whether financial, physical or professional, rather than flinch from it.
