The only thing I'm really interested in is why sama decided the other bettor had to be a VC. That's a pretty silly requirement.

Anyway this isn't a ballsy bet at all, really. Guys on 2p2 (poker forums) routinely make huge proposition bets that are more fun, interesting, and risky than this--occasionally for charity, as well (though not that often).

Losing this bet will likely do no more to either bettor than losing a $5 bar wager would do to me. Pony up the cash, shake victor's hand, move on with my day and forget about it.