Kawoomba comments on Gauging of interest: LW stock picking? - Less Wrong
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If more than a few LW'ers participate, the reliably best strategy to win $50 with play money would be to just invest in some very volatile option or other derivative, which'll either win over any conservative strategy or bomb out. Also the least amount of work, fire and forget.
I remember we held a similar contest in 5th grade - everyone paired up and picked some stocks out of the newspaper, and then at the end of a month investing the winner got some candy. The winners just invested 100% in Intel :)