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Go Big, Even if You Might Wind Up With Zero
You should really go really big, even if you probably will fail and wind up with zero. That's absolutely right. And I think one of the intuitions for why that's the case is this: The best possible thing is probably really good. It's probably orders of magnitude bigger than whatever you're sort of expecting. So any time that there is some non-zero and non-negligible chance of a really, really good outcome, are times when you're going to be incentivized more than seems natural, probably, to choose extreme outcomes.