Top VC Doug Leone Proves Badassery by Getting Drilled Without Novocaine
KEY POINTS
- â˘Doug Leone, Sequoia Capital partner since 1988, revealed he once underwent a dental procedure without Novocaine due to a tight meeting schedule.
- â˘In 1993, after a divorce left him homeless, Leone slept in his car at 3000 Sand Hill Road and counted on future earnings for hope.
- â˘Leone stepped down as managing partner in 2022 but returned in 2023 to dive into AI, driven by fear and a desire to stay relevant.
In a tale only venture capitalists and masochists could truly appreciate, Doug Leone, Sequoia Capital legend since 1988, skipped Novocaine for a tooth drill because 1993 wasnât rough enoughâhe was homeless, showering at 3000 Sand Hill Road and living on car payments. In 2026, at age 65, fearing Botox-like speech slurs over coffee charm, he boldly told his dentist to 'drill without any Novocaine.' His logic? 'I want to see if I am a badass.' Fear fuels his career moves and AI obsession even now that heâs back from retirement. The internet has since anointed him Chuck Norris of VC pain tolerance.
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(1 of 3)Doug Leone's dental courage levels: skips Novocaine before a meeting because 'being funny' is scarier than a root canal. Fear of awkward speech trumps city-sanctioned painkillers. We're all just amateurs at self-inflicted suffering.
Imagine being so terrified of sounding weird on a call that you opt for the most painful dental torture possible. Yes, Doug Leone, we see you.
Doug Leone sleeping in his car, showering at tech titan HQ, and drilling teeth numb-less is basically the startup grind but with more blood.
Source: Businessinsider | Published: 8/31/2026 | Author: Ben Shimkus
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