I came across an article in The New Yorker from 2010 that argued that the best entrepreneurs weren’t those who simply took bigger risks, but rather those who designed the risk equation to have more upside than downside. They carefully searched for asymmetric opportunities between risk and reward, and then seized them.
We’re often told this story that the greater the risk, the greater the reward, but that misguides us to think that the levers holding risk and reward are always equally balanced. The world is full of imbalanced levers, but finding those asymmetrical opportunities is hard work and might favor those who are non-conformist in how they perceive risk. You might not find them on a Forbes 30 under 30 list, and they probably won’t be in Silicon Valley folklore; instead, they will be relentlessly focused on finding the sure bet over the flashy bet.