The Web at 25: Dot-com bubble bursts and breaks me, too

Part 1 of The Web at 25, my look back at the first quarter-century of all things www, left off with both the Web and myself at the peak of an awkward adolescence in early 1995.

This is where things start to get really interesting.

Data nerds who shunned the Web when Tim Berners-Lee first demonstrated it in the United States in 1991 could no longer ignore it mid-decade. After the pioneering Mosaic Web browser launched, the Web saw an annual growth rate in service traffic of 341,634 percent, according to author and early Internet evangelist Robert H. Zakon.

In the span of about two years, Mosaic transitioned from a university-based project to a publicly traded company named Netscape that saw the price of its shares close at more than twice the opening price on their first day of trading in August of 1995. Companies grow up so fast these days, don't they?

From that point, the dot-com bubble began inhaling all the air (and capital) in the room and didn't stop until it left us all with economic Bubble Yum stuck to our faces.

There are millions of stories told about this epic boom, bubble, and bust period. This is mine.

It starts in 1997 with me at age 17 and a copy of Microsoft Frontpage in my parents' basement and ends with me living in a double-wide trailer on the banks of the Yukon River in the Alaskan Bush five years later. Here's what happened in between.

Respect my authori-tay!
Like many other young nerds of the era, I suddenly found around 1997 that my understanding and knowledge of the Web was commanding a lot more respect from people significantly more powerful, wealthier, and older than myself. By this time, using MS Frontpage, I had already built a few very simplistic Web sites for fun that were not even remotely attractive or very functional, but even my basic Web design skills were in high demand at the time, and it was still presumed that teenage nerds could be hired cheaply.

Suddenly I was taking meetings with one of the most powerful lobbyists in Colorado to talk about building a Web presence for key campaigns. I built a site for a top wedding photographer out of Boulder in exchange for learning her craft. When I went to college in September 1997, part of my financial aid package was a work study that made me one of the college's main Webmasters as a first-semester freshman.

Here's the kicker, though: I was a pretty bad Web designer. At the time, the Web seemed to be making everyone who touched it rich, spurring an outright panic by anyone who saw the emerging medium as either an opportunity or a threat. Businesses had to get online to stay competitive, as did politicians and even nonprofits, it turns out. They might not have understood what a domain name was, they just knew I could get them one.

And I did, at least until the rest of the world caught up with me, better Web designers became more plentiful (and cheaper), and the Web began to create opportunities to use another skill that I actually both enjoy and excel at (or at least I hope some readers think so).

I switched schools and majors from computer engineering to journalism and found that the Web would still provide. I landed a gig with an early iteration of MTV.com that took an earnest interest in America's local music scenes. I spent the next few years traveling the Midwest to interview artists, take in live shows, and write snarky reviews. I was still a student. I wasn't based in Silicon Valley or manning a startup, but I was still pursuing the dot-com dream for better or for worse. Sometimes it got a little out of hand.

After one particular show, my college girlfriend was a bit confused to find pop-punk darlings Good Charlotte in my living room along with a squad of local strippers providing a live demonstration of the latest technological advances in silicone. Those guys were straight edge, so there wasn't any cocaine involved that night, but there were plenty of other nights and other bands.

I, being a good boy, never partook. No, really.

Reckoning
By early 2000, I had no interest in finishing my broadcast journalism degree and struck a deal to design my own degree in online media (again, this involved a work study maintaining part of the university Web site and teaching a Web design course to other undergrads -- can't beat cheap labor, I guess). I began working on a little graduate student's project called Ironminds.com that was actually making a name for itself as a leading online magazine, competing with the likes of Salon and Slate.

I drove down to Austin that March with the Ironminds crew for South by Southwest Interactive, where we had been nominated for Best Current Events Site. Remarkably, we actually won, beating out big media names like "The Daily Show." I was 20 years old and I was part of something that smart people actually approved of, something that actually seemed to matter.

And for the first time, I felt as though I was among my own people. These people understood why I spent so many evenings glued to a monitor, trying to discern how the pieces all fit together, where it was going, where it could go.

At that year's SXSW Frog Design party, I pulled Ironminds founder Andy Wang aside.

"Andy, I don't want to go home. I don't want to go to college. I don't want to go back to Missouri. I want all this," I told him. I'm pretty sure we were both a little drunk, but I was still dead serious.

"Go talk to everyone," he told me. "Ask all of them for a job and then pick the best offer. You're a f*****g award winner now."

How come I've never heard this from any of my guidance counselors, I thought to myself. How absolutely brilliant.

By the end of that week I had a handshake agreement to start working at Business 2.0 magazine's San Francisco Bay Area office within eight weeks. If you don't remember Business 2.0, you could be forgiven. It was one of many such new publications at the time that didn't survive in its original form (remember Red Herring or the Industry Standard? No? Well they were real once too.) Eventually it was swallowed by Time, Inc. and got lost somewhere in the fallout of the AOL Time Warner debacle before disappearing altogether around 2007.

History now tells us that the dot-com bubble actually peaked two weeks before that fateful trip to Austin, but it was still easy to believe at that moment that the party could continue forever. So I packed up and went to California for what I thought would be a permanent move. But it turned out to be a front-row seat for a great unraveling.

Rude awakening
From the beginning, working at a "new economy magazine" was not all that I had dreamed that night in Austin. The people were nice, but my chops weren't yet well-honed enough to be a business reporter and I spent lots of my time copying text from the print magazine edition and pasting it on to the Web site. Not exactly the glamour I was hoping for, and how come we couldn't write some code to do all that anyway?

My living situation also proved interesting. Eventually, after time in hostels and finally being grilled rather intensely during an interview with my future roommates, I moved into a three-bedroom house where I was one of five tenants (the garage had been converted into two more bedrooms). The setup was unexpectedly quiet, however, since the room next to mine was never actually used by the chief operating officer of a major networking company who rented it as an emergency crash pad much closer to San Francisco than her large home in San Jose, farther south. I never saw the other person living upstairs, who also worked for a dot-com. I never even found out which one.

There were high points at the office, like writing a story on Craigslist founder Craig Newmark, who seemed to epitomize the spirit of Silicon Valley I was in search of, but ultimately I wasn't happy and things quickly got weird around the office as it became clear that the epic ride of the last half-decade was beginning to run out of fuel. Particularly after we moved into a new office space near arguably one of the worst neighborhoods in America, it all seemed to come unglued very quickly.

At a mid-summer staff retreat in the coastside town of Monterey, the tension was palpable, at least until it was all released in what may have been the largest collective binge I've ever been witness to. My editor ingested multiple mind-altering substances that weekend, broke one of hotel's windows (with his head, was the rumor), and spoke in a Beavis and Butthead voice for several hours straight. And he was one of the more well-behaved of my superiors that weekend.

It's hard to say exactly how many people moved to the Bay Area in search of that same dream during that time, but we do have a sense of how many ultimately joined me in abandoning the dream. An oft-cited figure places the number of people that quickly vacated San Francisco between 2000 and 2002 at 30,000, eventually making it the fastest-shrinking city in the country for a moment.

I went crawling back to college, and to Ironminds, which was ironically in the midst of being purchased by a group of "new-media investors" who moved it from Missouri to New York, rapidly poured millions into it, even after the bubble had clearly burst, and then shut it down just as quickly (although it did eventually lead to the creation of Deadspin via former Ironminds editor Will Leitch).

The dream that had helped me retroactively justify the self-imposed isolation of my adolescence seemed to be dead.

Set adrift
I turned my energies to improv and stand-up comedy, lazily finished my journalism degree, and began to see the value of drinking as a hobby. At the same time numerous ruined dot-com prodigies were retreating to yoga ranches and beyond, I took a gig living on a houseboat in the Florida Keys in exchange for -- what else -- Web design help.

I sometimes woke up on the beach after a long night at the bar on Big Pine Key and wasn't sure if I was having a good time or too depressed to even recognize it.

That fall I moved into a house in Denver with a few friends that I had grown up with to try and find a little grounding and figure what to do next now that Web design was providing me far less (I had to share that houseboat with 11 other guys and no air conditioning).

I delivered food and worked for family while still dabbling in Web design and writing jobs that suddenly paid next to nothing. 9/11 happened, the world seemed to be turned upside down, and that glitzy fantasy I encountered in Austin just 18 months prior felt like it had never even existed.

After months of sending resumes to anyplace that might be vaguely interested, I received exactly one job offer -- from a tiny public radio station in the Alaskan bush that was not even reachable by roads.

I signed a two-year contract sight unseen and flew to Alaska. I did not bring a computer or cell phone. Perhaps it was time to grow up and put away those childish things. Without being too hyperbolic, I think the dot-com bust may have broken my heart more than a little bit. Those digital dreams had been banished to the wilderness, and now, so had I.

Please share your own memories of the dot-com boom and bust in the comments section, and on Twitter at @crave and @ericcmack. In our next installment, I'll celebrate the 25th birthday of the Web by looking at those years that I spent watching from a distance as it continued to develop and eventually began to reassert itself.