In 2003 I was just a few years out of college, working for ClickSitez Japan, K.K., a startup trying to convince VCs that people were going to do their photos on

In 2003 I was just a few years out of college, working for ClickSitez Japan, K.K., a startup trying to convince VCs that people were going to do their photos on the interweb tubes. We had angel funding and a prototype/demo with one and only one error-free path through it (the "shining path", one of our advisors called it, and the name stuck). We on the engineering side divided our time between coding the prototype and helping the bizdev guys pitch it to anybody who'd listen: VCs, other dot-coms, even NTT. My business card read VP/UX, which was supposed to mean "Vice President, User Experience". Like a lot of dot-com startups at the time, we had like 7 vice presidents of this or that, with only 2 staffers below VP level. What I actually did know then, and simply wish I had factored into my decision-making processes more, was that the dot-com bubble was a bubble and that trying to play the stock game in a bubble isn't fundamentally different from playing blackjack. Bootstrapping is preferable to chasing investors, in retrospect. Of course, everybody knew it was a bubble; the technology stock analyst I was dating at the time told me, "Yeah. It's a bubble, but it's still paying out. So there will still be money to be made here, until the day comes that it was a bubble." It was March 2000 when that day came, as near as I can recall. We never got that next funding round, and as it started to become clear that the party was over, the three of us who could code went our separate ways, and the company was acquired by some short-lived web consulting company, which was in turn acquired by somebody else, and ultimately was bought by the posterboy of dot-com Internet flameouts, marchFIRST. The most valuable lesson that has stuck with me is that none of these people--investors, analysts, "experts", bosses, underlings, dot-celebrities of the day--knew what the hell they were talking about. I'm not saying that I did, mind you--nobody did. That's why these things are assigned descriptors like "revolutionary, disruptive technological paradigm shift". Because nobody knows what the hell all the effects are going to be. Not many of the things such hyperbolic labels are applied to actually turn out to do all that much disrupting. But the dot-com revolution was different--it was a bona-fide Gutenberg-level event, and for all the billions of dollars that were bandied about and the huge transfers of wealth and the frenzied investment in it, that was really just a pretty minor part of the whole picture. The impact of the Internet becoming a mainstream part of modern human society goes much deeper than that. And that's what made it fun to be living and breathing every day. Despite all the missed opportunities and inevitable what-ifs looking back, I'm glad I was there.