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.