Digital Hustlers: Living Large and Falling Hard in Silicon Alley

"In a forty-year business career we won't go through a period like we went through in the last five years."

-Kevin Ryan, CEO, DoubleClick

The commercial and cultural explosion of the digital age may have been born in California's Silicon Valley, but it reached its high point of riotous, chaotic exuberance in New York City from 1995 to 2000 -- in the golden age of Silicon Alley. In that short stretch of time a generation of talented, untested twentysomethings deluged the city, launching thousands of new Internet ventures and attracting billions of dollars in investment capital. Many of these young entrepreneurs were entranced by the infinite promise of the new media; others seemed more captivated by the promise of infinite profits. The innovations they launched -- from online advertising to 24-hour Webcasting -- propelled both the Internet and the tech-stock boom of the late '90s. And in doing so they sent the city around them into a maelstrom of brainstorming, code-writing, fundraising, drugs, sex, and frenzied hype…

until April 2000, when the NASDAQ zeppelin finally burst and fell at their feet.

In the pages of Digital Hustlers, Alley insiders Casey Kait and Stephen Weiss have captured the excitement and excesses of this remarkable moment in time. Weaving together the voices of more than fifty of the industry's leading characters, this extraordinary oral history offers a ground-zero look at the birth of a new medium. Here are entrepreneurs like Kevin O'Connor of DoubleClick, Fernando Espuelas of StarMedia, and Craig Kanarick of Razorfish; commentators like Omar Wasow of MSNBC and Jason McCabe Calacanis of the Silicon Alley Reporter; and inimitable Alley characters like party diva Courtney Pulitzer and Josh Harris, the clown prince of Pseudo.com. Together they describe a world of sweatshop programmers and paper millionaires, of cocktail-napkin business plans and billion-dollar IPOs, of spectacular successes and flame-outs alike.

Candid and open-eyed, bristling with energy and argument, Digital Hustlers is an unforgettable group portrait of a wildly creative culture caught in the headlights of achievement.

Casey Kait, at twenty-five, was vice president of MP3Lit.com and most recently a senior producer at Salon.com. She lives in New York City.

Stephen Weiss, at twenty-five, was executive vice president of RedFilter.com and a former magazine editor. He lives in New York City.