The Dot Com and Web 2.0 were classic bubbles, because they raised unreasonable expectations based on a financial fallacy. The unreasonable expectation was that anyone could get rich, and the fallacy in both cases was the belief that the money for these riches would come from a “greater fool.” At least in the Dot Com the greater fool was the stock market, which is reasonable. The greater fool in Web 2.0 was Google, which was going to buy all these start-ups for tens of millions. Google has some problems, but they aren’t fools.
The Dot Com people who ended up with worthless options looked to Web 2.0 as their chance to finally cash in on a bubble. They were wrong. Maybe they’ve learned their lesson and the next technology wave will have a different goal.