I find this paragraph interesting: "From the outside, it might have looked like I was crazy to feel this way. I had graduated from Stanford, I had a CS degree, and I knew how to play the startup game. In college I had started an ed-tech company, ClassOwl, that raised nearly a million in seed funding." Pardon my ignorance, but if a startup is a game, wouldn't knowing how to play be knowing how to win, i.e. an exit? I…
I was going to make a similar comment. There is an undercurrent of "raising money = success" in this posting. The whole concept of throwing money at 21-year olds and hoping they find an idea still seems bizarre to me, but obviously it has paid off for the YC guys.
This particularly struck me as ironic. Maybe he felt like an imposter because the other people had an actual plan and he didn't.