There is a whopper of a myth that exists about so-called serial entrepreneurs. It is widely accepted that those who have built and sold a company once have a better chance of succeeding with their next venture.
No doubt these second-time entrepreneurs have some smarts and some capital that they did not have the first time, but those smarts can actually get in the way of going for it and that capital can obscure the gnawing, clawing feeling of desperation that is the real driver of innovation.