Making sense (and art) of the dot-com crash

One block south of my office, a sign perches in the shadow of the wedge-shaped Flatiron Building: "DoubleClick Welcomes You to SILICON ALLEY."

Erected years ago by the first New York tech company to go public, the billboard became a "New Economy" totem, featured in scores of magazine photo shoots and breezy news broadcasts about entrepreneurial wunderkinder. After the crash, it morphed almost instantly into a kitschy relic -- an artifact from a time that New York techies simultaneously scorn and wistfully recall.

For many, the dot-com bubble has become little more than a punch line. But among those who spent 80-hour weeks mainlining coffee and obsessing about their jobs at startups destined for Chapter 11 liquidation, the effects of those years are harder to shake off. Internet startup veterans still meet in bars and Starbucks throughout the city for pink-slip (redundancy) parties and reunions with comrades from ventures that crashed. Lately, there's been a new occasion for gatherings: the documentary premiere.

Last Friday, the latest of these chronicles kicked off its run at an art-house cinema in Greenwich Village. "E-dreams" is the story of, New York's most notorious failed Internet startup. The company launched with a simple idea: Let customers order a variety of goods -- videos, magazines, snacks, beer, even aromatherapy oils -- from their PCs, then use a fleet of bicycle messengers to deliver merchandise within an hour. eventually expanded to more than a dozen cities, employed 4,000 workers across the United States and burned through in excess of US$250 million. It was New York's most expensive dot-com debacle.

There were two tales unfolding at Friday's "e-dreams" premiere -- the one on-screen and the one in the audience. The sold-out crowd was composed almost entirely of those who worked for, funded, shopped at or otherwise experienced the supernova. From the first moments of the film -- when co-founder and Chief Executive Joseph Park, a former investment banker in his mid-twenties, exhorts his staff to brace themselves for the startup's "roller-coaster ride" -- catcalls, applause and raucous laughter greeted nearly every scene. It felt like a living-room screening of a college clique's home movies -- but this slickly polished home movie involved startling bit players and staggering sums of money.

Uneasy laughter bubbled through the audience during footage from's boisterous Oscar party, at which a tipsy Park led the crowd in a cheering salute to's just-filed-for IPO (initial public offering). It was March 2000. Three weeks later, the stock market was in shambles. Four months later,'s IPO -- intended to raise US$150 million -- was withdrawn. During that scene, no one laughed. The dot-com boom-and-bust cycle is too recent for its sting to have faded. When's chief financial officer first appeared on the screen, several in the cinema hissed.

Later, as the audience spilled out of the cramped theater onto the equally crowded sidewalk, much of the chatter focused on how "e-dreams" compared to "" -- another documentary about another Alley dot-com that screened at another art-house cinema in the Village several months ago.

I'm sure there are more coming. One row of my office bookshelf is filled with roman-à-clef novels about the authors' dot-com days; another shelf is stacked with memoirs penned by dot-com founders about their heady days of living as paper millionaires while spending sleep-deprived nights worrying about bouncing their staffers' paychecks.

My theory on the trend: Art is cheaper (and more satisfying) than therapy. Ten years from now, when the dot-com t-shirts have disintegrated into car-waxing rags and the logo-festooned coffee mugs have all been lost or dropped, we'll still have reams of business-school case studies analyzing the strange phenomenon of the late 90s tech boom. And we'll have the plays, novels, memoirs, screenplays, Web sites, performance art and who knows what else.

Considering how long billboards tend to hang around in New York, we'll probably still even have the DoubleClick sign.

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