Sequoia Capital's Doug Leone on Luck & Taking Risks

He describes formative moments like being told to “clean the bathrooms” in an early job and difficult high school years that still trigger insecurities and ego, which he says he has to consciously manage even decades later.

He points to being in the right places (a sales territory near Columbia where he learned about ARPANET) and a chain of events (Sun Microsystems, meeting key people, learning what venture capital was) as pivotal, while also emphasizing that he hustled—writing many letters, cold-calling, and leaning forward to listen.

He credits Sequoia’s founder with prioritizing market understanding and recruiting “non-conventional” people, and says Sequoia still optimizes for candidates who may not “meet spec” but are “special,” including those with both IQ and EQ and something to prove.

He says the firm stays motivated by paranoia about slipping into irrelevance, a belief that “doing nothing is risky,” and a willingness to change even when things are working—like removing posters celebrating wins to avoid complacency.

He says Sequoia meetings are disciplined (start/end on time, no phones) and that tough questioning is meant to understand the business, not be rude; he praises pitches characterized by crystal-clear thinking, self-awareness, and honesty about mistakes.