Pretty much every startup success story has an "and then we got spectacularly lucky" part to it. In Viaweb's case, it's more like "and then, for the nth time, we almost died, then somehow didn't", but the idea is the same. It's one of the great unmentionables in the startup world, and understandably so: succeed and you want the credit; fail and any mention of luck sounds like sour grapes.
I've heard a lot of startup founders talk about a lot of startups, and only Marc Andreessen (of Netscape fame) both realized and admitted to the large role luck nearly always plays.
I should add that great startup success stories almost always involve founders who were awesome as well. (Netscape and Viaweb both qualify on this count.) It's just that being awesome isn't enough. Traf-O-Data had awesome founders, but it failed; those same founders, Bill Gates and Paul Allen, had better luck in their second venture.
Its funny - but for so many startup success stories, bubbles are the pink elephant in the room.
When you try to draw lessons from success during downturns, the lessons are very different, and yet most thought leaders come from bubbles. This deeply effects the quality of the advice out there - most of it comes from people who are to some extent unknowing products of bubbles - but who attribute all of their success to actions they took that have universal applicability. When it often ain't so.
For this reason, for me, 'startup credibility' goes up tremendously when it comes from a serial entrepreneur, or from someone that has actually built a cash-starved company to success during a downturn. "What can I do with very little?" and "What can I do if it is possible to raise $1 million?" are fundamentally different questions - and the same person isn't necessarily going to be skilled in both situations unless they've demonstrated that ability.
Whereas this comment - it has the legitimacy of coming from a complete failure :D
Finally... if your community leaders are state employees that can't say anything negative in public... you really need to be aware of that before you take their optimism at face value. Take to time to query them in private, to find out what they actually think. It might save you some mistakes and some grief.
Oddly, self-help gurus seem to enjoy the opposite phenomenon (i.e. those who can't, teach self-help seminars).
I remember at one point this guy Richard(?) Kiyosaki had a book "Rich Dad, Poor Dad." In it, you basically found out that Kiyosaki was (a) lying his tits off or (b) a terrible investor. You found out that he'd been bankrupt, and had run several companies into the ground. That he invested in mining companies in Russia whose value would swing 50% up and down from day-to-day - but that this didn't bother him... Wacko.
Yet, somehow, the book was a total phenomenon and made the guy huge amounts of money.
I agree there's too much advice from people who haven't been there themselves.
My own article shows that advice from people who HAVE been there (like me) is still suspect, but at least it's MORE interesting than people who have ONLY failed.
Failing, learning, and then succeeding just feels like a better place than just failing, SAYING you learned, and then teaching.
At least he failed the first time (websites for galleries), and learnt from it. There was also a control in the form of other similar businesses at the time.
