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Doug Leone: “If you’re desperate, it’s a great asset”

July 07, 2025

The Sequoia partner is asked what he looks for in entrepreneurs. He responds:

“I think entrepreneurs—like investors—come in different flavors. And I will tell you, as I told my kids, that if you’re desperate, it’s a great asset. If you have too many choices in life, it clouds your thinking. When you have only one way to go and that’s forward, it’s very easy. You just go, go, go. Failure is truly not an option.”

Doug and Sequoia look for people who’ve done quirky things and taken risks rather than “followed the same tracks” as everyone else. They also look for domain expertise and people who are solving their own problem.

For example, when Jan Koum had a need for privacy and low cost messaging, he built WhatsApp.

“Or something as simple as Zappos,” Doug continues. “The founders of Zappos couldn’t find a pair of shoes! We look for people who are trying to solve problems that they themselves have.”