It is clear from Maciej's posts that the $20K in and of itself is fairly marginal ($20K ~= 3 weeks of revenue). Part of why I was excited about the Pinboard app

It is clear from Maciej's posts that the $20K in and of itself is fairly marginal ($20K ~= 3 weeks of revenue). Part of why I was excited about the Pinboard application was to see whether the entire experience would help Maciej improve Pinboard and grow it a bit (not hockey-stick, but an OOM bump), to turn it into a new Delicious. The other part of why I was excited about the Pinboard application was because I think YC would be better off embracing the bowling ball cleanse that Maciej promised; if the VC rule is that the best investments don't look like the best investments, then YC would be smart to embrace Maciej--not that Pinboard will turn into the next hundred bagger, but that getting to know and understand one's smartest critics isn't a bad strategy for escaping one's own biases. The trope isn't called "wise fool" for nothing. Considering the badness that ensued, Maciej's request for a charitable donation seems entirely correct. Pinboard can earn $20K easily enough, and the potential for good to come of the clash between views is no longer a possibility. It also serves as a useful escape hatch from the controversy; we don't have to revisit it in the future, as the question of how Pinboard spent the money is now moot.