In 2000? Maybe not. It was very different back then.
In any case, even if you don't think Broadcast.com or some of his other business ideas are the smartest ever, you can't fault the guy for being smart enough to take the money and run.
Well, the difference between $200/share and $230 would be about $300 million, since he says he sold for $2B. $300 million isn't small potatoes, even if you have $2B.