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I think sometimes you need a little overconfidence.

After all, used to be taking even financial risks could get you killed very easily. Nowadays, what's the worst that can happen? You end up broke and living at your parents until you're 25.

Take the risk. It's worth it. Not enough people are taking them.

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I don't really have the numbers to back it up, but I think if you compute the expected value of starting a venture, the numbers will show you that you that taking the risk is not worth it (vs. getting a normal salaried job), since most ventures fail.

With that stated, I think that entrepreneur overconfidence is a features and not a bug. The fact that entrepreneurs are overconfident may, in most instances, be to their detriment, but it also will engender great breakthroughs that have huge payoffs and make society much better. Without overconfidence, this wouldn't even be possible.

Expected utility is probably a more appropriate gauge for these decisions, rather than expected value

Agree that you need a little overconfidence sometimes. But perhaps the fact that there are more support systems around (move back in with parents, social benefit), means that we as a generation never grow comfortable with risk in the first place, and thus can never be truly confident with it.

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