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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?

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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.

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