Yes, it matters. An entrepreneur friend of mine sold his first company during the dot com years and made a mountain of cash in the deal. He then went on a spen

Yes, it matters. An entrepreneur friend of mine sold his first company during the dot com years and made a mountain of cash in the deal. He then went on a spending spree (trying to build new, ultimately unsuccessful companies) that very nearly bankrupted him. With his savings dwindling and the looming prospect of having to go back to work for someone else, he locked himself in the basement (so to speak) and, in a last-ditch effort, built a profitable company in a few months time. AND, here's the part that gets me, he made this product successful, nearly single-handedly in a market that was already crowded with competitors. He tells me now that its harder for him to have success in business (5 failed in the last 2 years), primarily because there is no real sense of urgency to drive him to succeed anymore, what with the checks still rolling in. This is despite the fact that he is amazingly talented, both in software development and in business development. Since meeting him and learning his story, I have been looking for ways to make myself as determined/desperate as he was when he built his company.