I’m with Catrina. The good time to start a company was when she and Stewart started Game Neverending, which became Flickr — otherwise known as the depths of the crash. That’s when I started Supernova, and when most of the other Web 2.0 darlings (Technorati, Six Apart, Weblogs Inc., etc.) got off the ground. It’s also, by the way, when Google went from good to **INSANELY HUGE**.
Sure, you can start a great company today. And you could fail with a company started in 2002. And, you can be optimistic — as I am — while questioning the excess of hype and hyperbole we’re seeing today. Entrepreneurs are going to be entrepreneurs, whatever the climate, because that’s what they do. It’s important, though, for the rest of us to keep some perspective.
Some people get lucky; if they didn’t, Las Vegas wouldn’t exist. But I’m putting my retirement money in a diversified investment portfolio, rather than the lottery or San Francisco real estate, because I like the odds better. Same dynamics here.