Also drove to Foxwoods to play poker once with my co-founder when we were particularly desperate. We only had enough money for one buy-in ($300). Figured that if I was asking my parents for money again, asking for an extra $300 was worth the risk, if I had a chance to win and not ask for anything.
Bill also took random jobs on Craigslist (helping people set up pod-casts, writing papers for wealthy foreign students, etc.)
I taught the LSAT and did "law school admission consulting" which basically translated to helping people write personal statements.
(I'm "aberman", one of the co-founders of WePay)