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cata comments on Why We Can't Take Expected Value Estimates Literally (Even When They're Unbiased) - Less Wrong
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I think that for the purposes of establishing a prior distribution of expectation, "playing poker with Warren Buffett" should be in a really different reference class than e.g. "playing poker with my buddies on Thursday." So in your example, I don't think that playing for a billion would actually be so many standard deviations out as to make it less positive than playing for a hundred.