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The list has become a bit of an institution in Silicon Alley, as has Calacanis himself, whose twangy New York accent and hucksterish enthusiasm are ubiquitous in features about New York new media. Calacanis was extensively profiled by the New Yorker and Wired in 1999, a rather notable feat for a former gossip columnist still in his 20s, who has built a small empire on the merit of his lists. (This year, Calacanis features not only the Silicon Alley 100, but the Digital Coast 50 in a separate supplement.)

The Alley 100 issue is a chance to both kiss the collective behinds of Alley digerati -- Calacanis' list this year prominently features friends and colleagues such as author Douglas Rushkoff and indiewire.com editor Eugene Hernandez (who shares the same publisher as the Silicon Alley Reporter) -- but also to tweak the notion of CEO self-importance. Alongside such Fortune fare as Jay Walker of Priceline and Geraldine Laybourne of Oxygen are listed more edgy names like Emmanuel Goldstein, editor of the hacker zine 2600; Rufus Griscom and Genevieve Field of erotica site Nerve; and the omnipresent founders of Feed magazine. (Those dropped from last year's list are also mentioned, and admonished for being "boring.")

Calacanis' Silicon Alley 2000 conference, which took place this week in New York, is a similar extension of his puckish who's who. Part exclusive event (the three-day conference featured not one, but four intimate dinner parties) and part schmooze-fest, the conference seems to have little purpose beyond inviting those same self-important digerati to talk onstage. But while the conference agenda is packed with heavy-hitter CEOs like Candice Carpenter of iVillage and Bob Davis of Lycos, it also features more unusual names -- such as members of the Swiss art prankster group etoy, or musicians from They Might Be Giants. (Calacanis' mother, who runs the iHealth newsletter, is also prominently in attendance.)

Of course, the edgier fare didn't go over so well with the predominantly business crowd, which seemed to be more interested in networking than expanding their minds with panels like "News in the Digital Age" or fireside chats with Bill Gross of Idealab.

While Douglas Rushkoff's keynote on Wednesday, admonishing buttoned-up dot-com companies to start "having more fun," was an audience hit, it was a venture capital panel with investment bankers like Bob Leason of Wit Capital and incubator founder Jake Winebaum of Ecompanies that really got the business cards rolling -- the line to glad-hand these panel participants after the discussion was practically out the door.

A quirkier panel featuring the artists of etoy, by contrast, was nearly empty. "This should be really interesting," said Calacanis gleefully, looking around the room to see which CEOs might show up to see the controversial group, which spent much of last year embroiled in a lawsuit with Etoys (a company listed at No. 2, incidentally, on the Digital Coast 50 list). Instead, only a smattering of arty types -- including the renowned DJ Spooky -- listened in while etoy members explained their battle and their recent public offering. (The artists have raised nearly $200,000 by selling stock -- the shares themselves are little works of art -- in their endeavor. As one etoy member wryly observed, "Everything at this conference is about increasing shareholder value.")

When Calacanis realized that etoy wasn't quite the audience draw that he'd expected, he shrugged. "It's worth it to me to have this on tape for the future," he laughed, and egged moderator Rushkoff on to "ask sillier questions." It's unlikely that etoy will end up on next year's Alley 100 list, since the group lives in Europe, but it doesn't seem so far off the map; Calacanis, I'm sure, would love to annoy the eToys executives by lauding their arty enemies. Perhaps a Digital Europe 100 is next?
salon.com | March 3, 2000

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