The venture capital-backed startup world is a bubble. People outside of it think we're risk lovers, which is reasonable since the our failure rate is so high. I think that the best entrepreneurs are risk managers.
Most people are enveloped by the emotion of risk, and it freezes them. They think about how terrible it will be if they fail, how awful every conversation with be explaining what happened.
It's better to separate the emotion from the risk. Separate the fear of consequences from the consequences themselves. I do that by asking myself "What's the worst thing that can happen?" I explore that outcome, imagine the conversations I dread, think about what would come after the worst thing. Having fully considered the downside, I almost always conclude that the worst thing isn't really that bad.
This same thinking works when I'm at the top of a steep ski slope, or at a cocktail party and have to make small talk, or when I need to have a hard conversation. All of those things feel riskier than they are.
An emotionless view of risk allows entrepreneurs to make better decisions and take bolder action.
I've started and/or run too many venture capital-backed software companies, plus one ill-fated food startup.