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GuySrinivasan comments on The Last Days of the Singularity Challenge - Less Wrong
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A friend points out one possible way this reasoning doesn't work: charities can gain political power by quoting a larger number of individual donors. This would argue for giving $10 to several charities and the rest of the money to the best one.
Or perhaps giving $10+e to lots of people on the condition that they give $10 to the charity you'd like to target.
This would make the IRS sad if they found out. You wouldn't like them when they're sad.
Good point. Even better, then: charity trades. I give $10 to your charity and you give $10 to my charity.
Probably a wash if everyone does it, but might give a selective advantage to rationalists if practiced by rationalists only and the practice didn't spread beyond that... which seems unlikely in the long run, but not too impossible in the short run.