“Venture as an asset class is mediocre unless you can consistently hit 20 to 30% IRR, and the only way to do that is a real comparative advantage, not consensus bets. I want half my smartest friends laughing at any deal I do; if it feels safe, the alpha is already gone.”
“I don't think of our seed checks as option bets. Every company we lead at Footwork matters to us, and we size each one to return a multiple of the fund if it works. The high-risk part comes with the territory, but we're not spraying and praying; we're making a small number of concentrated, high-conviction bets where we can be genuinely helpful.”
“I used to think venture was a risk-free return; the math convinced me it is often return-free risk. Half our investments at Sequoia do not make a profit, so the only reason to take that risk is the chance to partner with founders who can build something truly enduring.”
“I bet on Robinhood at seed when everyone else passed, and that one $250K check became about $400M. That is the whole game: most seed investments die, so the ones that live have to pay for everything else, which means you need concentrated ownership in a small portfolio, not a spray-and-pray index.”
“I look at high-risk venture bets through the lens of asymmetric upside and the courage to be wrong. The best venture bet I can point to is Mike Moritz backing Instacart after Sequoia lost $370 million on Webvan: same space, fresh first-principles read, no pattern-matching.”
“I bet my life savings on Flexport once, so I take high-risk seriously: it's not about courage, it's about whether the upside can repay the fund. At Saga we call it high convexity, 6x or 1x, because a 3x winner barely moves the needle when you're charging 2 and 20.”
“I don't think venture is about avoiding losses. I assume every investment is gone the day we make it, which leaves only upside. The game is to make the consequence of success consequential enough that one or two bets pay for the whole fund.”
“Venture capital is not about avoiding risk; it is about taking intelligent, calculated risks before the world agrees. I look for asymmetric opportunities where the upside meaningfully outweighs the downside, and back founders who see possibility where others see uncertainty. The hard part is not betting, but having the conviction to pick and own the right non-consensus bets.”
“My philosophy is simple: take on as much risk as possible. At Founders Fund, the first filter we used was why won't other VCs like this? because the best returns come from contrarian bets, not consensus. I bet my career on aerospace when nobody cared, and now the same investors who passed are marking up my deals at 10x.”