That's just it - why is he more tolerant for risk than everyone else? Risk is not a personal thing - it just is. It's not like he gets his money cheaper than anyone else.

Either he's wrong and everyone else is right, in which case he's burning money, or he's right and everyone else is wrong, and he's burning less money.

Either way, I don't get it. These guys are very well connected. Is it so hard to participate in Y Combinator Series A round that they need to spend this much money just for the opportunity?