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David Senra: Doug Leone on Sequoia, Fear, Great Founders & Starting Over at 69

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Doug Leone spent 26 years helping lead Sequoia Capital through successive eras of technological change. Born in Italy, he came to the United States without speaking English and carried the insecurity of an outsider into his career. That fear became fuel: whenever he felt himself falling behind, he forced himself to start over. After stepping down from Sequoia at 65 to make room for the next generation, he returned four years later. Now he considers himself a low-level analyst again, racing to understand an AI revolution that he believes is rewriting business more radically than anything he has seen before. Leone explains the three questions he asks before making an investment: Would he put his children's money into it? If he could make only 20 investments in his life, would this be one of them? Could it return the entire fund? He is interested only in extreme outliers—companies capable of returning 100 times the original investment—and says the biggest mistake venture investors make is selling their winners too early. Sequoia once owned enormous stakes in Apple, Cisco, Google and NVIDIA, but even the greatest investors failed to anticipate how long exceptional companies could cont

[David Senra] All right, we were just talking before recording, and you just said something that was very interesting. We were talking about people that dominate for decades. You're one of them that's done so, and you said an interesting question is to ask how and why somebody would dominate for decades. What's your answer to that? [Doug Leone] My partner in India [Doug Leone] said there are many roads to heaven, [Doug Leone] and so there are many ways to dominate. [Doug Leone] Take Steve Jobs. He had really one job, and he dominated in that domain for a lot of years, or Jensen Huang. Those…

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