I am almost afraid to ask you this, but here it goes.
On the last few weeks/months before starting Viaweb, did you consider yourself a failure for being almost 30, well-educated but out of the formal career track, "poor" and unmarried? If so, was that the fuel behind your many amazing achievements later on?
No, not really. I'd written the two Lisp books, and people liked those. Not a lot of people, but they were people whose opinions I cared about. Actually Viaweb felt like more of a compromise than the way I'd been living before, because it was something I was doing mostly for money.
So, you finally had your first taste of startup success at age 34. And you started Y Combinator at 41.
Think your story, along with many others in the Valley (e.g. Jim Clark), goes to show that this is a long-term game, and it only gets better with age and experience.
On the last few weeks/months before starting Viaweb, did you consider yourself a failure for being almost 30, well-educated but out of the formal career track, "poor" and unmarried? If so, was that the fuel behind your many amazing achievements later on?