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Alsadius comments on Gauging of interest: LW stock picking? - Less Wrong
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The problem is that you're setting up the goal of being #1 in a (presumably) large group, which creates wildly different incentives than actual investing. The proper strategy is to pick a single investment with volatility such that it has a (1/number of participants) chance of being utterly dominant at the end of the period, because a moderate return is no better than bankruptcy.
This is a good point. I think that part of the plan was a bad idea.