Sam Schillace came to a Bootstrapper Breakfast last year, he has started more than a dozen firms (some of them more short-lived than others). He felt that they got a huge boost from Tim O'Reilly putting them on stage before a Microsoft keynote to set up a number of questions about "Word on the Web" and that they were in the right place at the right time to trigger a bidding war. They definitely had a lot of experience but there was a considerable amount of fortunate timing involved. There is a short interview with Sam here http://www.bootstrappersbreakfast.com/blog/2008/10/01/sam-sc...