Knowing when to sell and at what price is one of those questions that doesn't get talked about very much. In the game of business, success is measured by dollars. It makes sense that people are motivated by selfishness and "greed" and the general desire to improve one's financial standing. This isn't a bad thing -- it's what capitalism is based upon. The danger for an entrepreneur comes when it comes time to sell part or all of their company. The danger comes when an entrepreneur tries to over-optimize the value of its asset and thereby doesn't take a critical offer of money when it's offered. In my mind, Friendster is the poster child of pigs getting slaughtered. This company had the opportunity to sell for 30MM in pre-IPO stock to Google but turned down the offer. I bet the entrepreneur regrets that decision!
Recently, I've seen a case of an entrepreneur doing a great job tkaing the money to grow his business (I can't talk about the fiancing publicly because it's not announced yet). The entrepreneur realized in the rpocess of fund raising that they had probably under-priced the round by 20% but rather than go back and redraw the deal and screw it all up, he opted to plow ahead an dnow has the necessary (critical) cash to grow the business. And I have another friend who is selling his business for a price he knows isn't the best, but it will give him a really valuable win at a critical time in the market. Remember when the deal comes, the bird in hand is really valuable ....and pigs get slaughtered.