Pretty much all of Thiel's investing thesis is to invest in things that are statistically on track to fail, but whose payoff if they succeed is greater than most people imagine. PayPal, Facebook - both of these were terrible ideas when they came out (along with a number of other ones that did, in fact, fail). His idea is that people consistently mis-price risk, and so investing in a portfolio where everyone else thinks it's a terrible idea but you have reason to believe it's a better idea than others suspect will give outsize returns. (Note: it doesn't actually have to be a good idea, it just has to be better than everyone else thinks it is.)
Supporting Trump fits perfectly into this: if he loses, he gets egg on his face (which most people will forget fairly soon) and may lose out on a little startup dealflow, but if he wins, he becomes the sole connection between the Presidential Administration and Silicon Valley. That's worth a lot more than $12.5M.
Supporting Trump fits perfectly into this: if he loses, he gets egg on his face (which most people will forget fairly soon) and may lose out on a little startup dealflow, but if he wins, he becomes the sole connection between the Presidential Administration and Silicon Valley. That's worth a lot more than $12.5M.