With dot-com valuations rising by the minute, the question of “when to sell” is becoming more and more important. A lot of people tell me I was smart to sell MySpace to Newscorp in July 2005 (it went for $580 million), because it recently RE-sold for $35 million (Go Specific/JT!). It’d be nice for me to take credit for that decision, but it was not my decision to sell MySpace (our parent company had control and made that decision themselves). Personally I can’t complain — I made far more money than anyone would ever need, had the time of my life, and was lucky in so many ways. But the truth is that if MySpace had waited a year or two, it clearly would have gone for single figure billions. What’s more, If it hadn’t sold at all, we wouldn’t have been forced to monetize in a way that was against our longterm interests. Think of all the value Zuck has built by staying in control for so long and for refusing to go public. Also I get the impression that he doesn’t care in the slightest how the market values his work. He’s on a personal mission to improve the world, and I’m glad he is. In any case, very difficult decisions ahead for VCs, entrepreneurs and stock market investors. I’m just hoping this doesn’t end like 2000 again. The desire to make a buck does help fuel innovation, but it can also wipe out people’s nesteggs if they get too greedy.