Lost in Silicon Alley

Aug 15, 2001

by Anton Zuiker

Digital Hustlers (ReganBooks/HarperCollins, 344 pages, $26), a new book of oral history that purports to chronicle the heady times of Silicon Alley’s heyday in the Internet sun, begs the question: Who got hustled?

Though she chuckles at the question, author Casey Kait steers her answer to the other meaning of the book’s title.

“It’s less about people reaching into your pockets and stealing,” she says, and more about the hard work of an army of young entrepreneurs. “The word hustle came up a lot in our interviews, as those people told their stories of trying any which way to make their businesses successful.”

Kait’s co-author Stephen Weiss addresses the con. “In general, this book is about the rise and fall of the Internet economy, of the shift from wealthy venture capitalists to mom and pop putting their pension money into tech stocks. Those are the people who got hurt the most in speculative start-ups.”

Digital Hustlers comes out in a murky time, with the Internet luster not so bright. The book looks back on the years 1995-2001, when New York’s Silicon Alley was a beacon to entrepreneurs energetic enough for the cyber land grab. The 60 individuals quoted in this book recall their parts in the flurry of creativity, collaboration and convergence that made them perps – unwitting or not – in the hustle. “It’s one big confidence game,” says Seth Goldstein, founder of SiteSpecific and a partner in the important venture capital firm Flatiron Partners. But again there’s a double entendre.

That con game that was the Internet stock bubble was built on real self-confidence. Most of the players interviewed for the book are part of the Gen-X cohort that in the early Nineties was supposedly typified by the West Coast grunge movement, college-educated drifters with no plans for their lives. Digital Hustlers captures nicely the transcontinental shift to Silicon Alley that ended the Nineties with that same generation falling over themselves in the rush to actualize their ideas and change the world with their inventions. “These people had Gen-X ideals,” says Weiss, “and those ideals empowered them to take meetings with executives at IBM and Duracell and other large corporations.”

Silicon Alley, of course, is New York. “There’s something about the city that rewards hungry people,” says Kyle Shannon, a former actor who founded the Internet consulting group Agency.com. (Agency.com is just one of the dozen or so stocks that rises precipitously and then skims the bottom of the well – or is flat broke and dead – by the book’s end.) A capital of fashion, finance and media, New York was a crucible for Internet start-ups, from content sites to streaming media to consulting agencies. At the height of the creative craze in 1999, there were 8,000 companies, which had raised more than six billion dollars in private and public funds, write Kait and Weiss.

When the authors caught up with their subjects, they say, most were sitting in huge loft spaces surrounded by rows and rows of empty cubicles after rounds of layoffs. “It was a strange time for them,” says Weiss, “but they enjoyed talking about the early days.” The halcyon days promised success, fame and riches, and included late-night parties, strippers at going-live celebrations, free vodka and cigarettes, sex in the closet and drugs whenever.

“It was mass-delusionary self-gratification. Everybody feeding on everybody,” says investor and Internet celebrity Esther Dyson toward the end of the book, in the “Fucked Companies” chapter. That one follows chapters about the now-defunct Pseudo.com and TheGlobe.com. Josh Harris, founder of Psuedo.com, is a heavy presence in the book, and his cutting-edge brilliance – his site was one of the first Internet broadcasting companies – is foiled by his Bright Lights, Big City flamboyance.

“Yes, it was a time of mass delusion, but also a time when people charted a new industry,” says Weiss. In the book, Alan Meckler, founder of Internet.com and the publication Internet World, relates the story of the Internet to the legacies of the telephone, television and birth of the automobile. “I still think the Internet is the most exciting industry in the history of the world,” he says to close the book. “It’s so grandiose,” says Weiss, “but that’s the flip side of Dyson’s quote.”

It may take 20, 30 or 50 years to have enough perspective on the legacy of the Internet to understand how revolutionary it is. As oral history, Digital Hustlers does a nice job of weaving together the eyewitness accounts of those at Silicon Alley ground zero. But the smoke is still clearing, and it can be difficult to find a focus on who’s to credit for the revolution and who’s to blame.

“The people in this book are such characters that readers have strong reactions to them,” says Kait. “They come under a lot of criticism for being the parties that poisoned the well.”

“But maybe they’ll age better with time,” replies Weiss.

And time is what this book needs. Read it now if you’re deep into the Internet and want to learn from your contemporaries. If you’re just now dabbling with e-mail or still beholden to AOL, come back to the book in 20 years, when it will either be a chronicle of the Big Bang birth of a new electronic world or just another early century reality show producing unnecessary blather.
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The authors of Digital Hustlers invite other dotcommers to add their perspectives to their website, www.digitalhustlers.com. So I’ll offer my Rust Belt version here:

Just two years ago, I was sweltering in the South Pacific sun as a Peace Corps Volunteer, wondering why I’d picked that moment in time to withdraw to a technology-free tropical island while my contemporaries were blazing onto the pages of Newsweek with tales of their stock-option millions.

One day in the capital, I met a young couple, who told me they’d cashed out and were taking a year to sail around the world. I went back to my hammock and hoped I could still catch the Internet wave when I returned to the States in 2001. I did, barely, but no riches for me.

I’ve just extracted myself from my second job in a year with a struggling Northeast-Ohio startup. The first company folded, run into the ground. Like Jon Effron in Digital Hustlers, I heard the refrain “You do the math,” but when I did, my paycheck wasn’t what was promised and the CEO was diverting funds.

“People in this industry are surprisingly articulate,” says Casey Kait. “They’re good storytellers – pitching the business is pitching the story.” The second company has a great story, told by a passionate founder. But when I started work, the pitch had changed to reflect a changing business, and I never got to do my job as promised.

Maybe I didn’t hustle enough. Or maybe I got hustled. Is it too late for me to start HammockDreaming.com?

Cleveland Free Times, August 2001

Anton Zuiker ☄