He did make it look easy. It's like he said "Well, you just ask for 100k, get it, build some stuff, get more money and then..."
I think one thing that got him inside was the execution. Mint is just cool to use. If I was an investor, I'd try the site and just say "Hey, this is really cool to use. And useful. And in a lucrative niche." Then I'd write a check.
How is he an insider? Because he went to Princeton? Is he related somehow to Larry, Serge, Bill, or one of the Steves?