Randaly comments on Why I'm Skeptical About Unproven Causes (And You Should Be Too) - Less Wrong
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The reason not to play a lottery is because it is a zero-sum game in which the rules are set by the other agent; since you know that the other player's goal is to make a profit, you should expect the rules to be set up to ensure that you lose money. Obviously, reality is not playing a zero-sum game with humanity; if one chooses a different expected payout structure- say, you have no idea what the specific odds are, but you know that your crazy uncle Bill Gates is giving away potentially all his money to family members in a lottery with 2$ tickets- then obviously it makes sense to play.
These were my thoughts when I read this.
A better analogy might be buying stock in a technology startup which is making a product completely unlike anything on the market now. It is certainly more risky than the sure thing, with lots of potential for losing your investment, but also has a much much higher potential payoff. This is generally the case in any sort of investing, whether it be investing in a charity or in a business -- the higher the risk, the higher the potential gain. The sure stuff generally has plenty of funding already -- the low hanging fruit has already been taken.
That being said, one should be on the lookout for good investing opportunities of both kinds -- charging more (in terms of expected payoff) for the riskier ones but not shunning either completely.
I think this is also a dangerous example because most of the salient and readily-available examples of doing this are the highly-publicized successes (this might be less true for people who are actually actively involved in technology investment - I say this from the perspective of an outsider).