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Suit 2.0

Back in the nineties, Jason Calacanis was a Silicon Alley cowboy. Now, at AOL, he’s in full corporate harness. Is that the only way for an entrepreneur to get to the top?


Back in the fall of 1998, on the night after AOL announced that it was undertaking the first great merger of the Internet era—its $4.2 billion takeover of Netscape, the seminal Silicon Valley start-up—I was having a drink with Marc Andreessen, Netscape’s co-founder, and asking how he felt about the prospect of spending time in (gulp) Dulles, Virginia. Out in the Valley, AOL, for all its success to that point, was seen as terminally gauche: the company run by (double gulp) marketers (as opposed to technologists), the service aimed at consumers who didn’t know a modem from a microchip. In the past, in fact, Andreessen himself had voiced these very sentiments to me. Yet now he’d signed on to serve as Steve Case’s chief technology officer. “I was wrong,” he said, a little too emphatically. “The opportunities at AOL are breathtaking—dude, it’s gonna be great.”

Less than one year later, Andreessen had essentially quit. Having paid a bundle for Netscape, AOL really hadn’t the faintest clue what to do with it. And so Andreessen—bored, frustrated, hungry for another payday—returned to the start-up game. Meanwhile, Case, undaunted by one foundering megamerger (as these people always are), promptly turned around and bought Time Warner (you know the rest of that story), and Netscape was left to languish as a second-tier Web portal.

I mention all this because, unexpectedly, Netscape is back in the news, and with a twist that makes the Andreessen precedent worth exhuming. On July 1, AOL, as part of its ongoing efforts to transition its business away from Internet access toward ad-supported media, will relaunch as a “social news” site. And the man the company has put in charge is Jason Calacanis.

Calacanis, of course, first rose to prominence in the nineties as the proprietor of Silicon Alley Reporter, a role that made him, in a way, as much of an emblematic figure of the boom as Andreessen. Though at the time they seemed like thoroughly different animals, the differences were coastal, stylistic—superficial. Where Andreessen posed barefoot on the cover of Time, Calacanis paraded through a profile in The New Yorker wearing only black. Where Andreessen imagined himself to be the next Bill Gates, Calacanis mused, “I don’t see why I can’t be the next Michael Eisner or Barry Diller . . . someone has to be.”

Though Calacanis, 35, has yet to reach the commanding heights of moguldom, he has at least made himself rich. After the collapse of Silicon Alley Reporter (though collapse is a descriptor that annoys Calacanis, about which more shortly), he founded Weblogs, Inc.—a collection of 85 blogs including the popular Engadget—in 2003. Two years later, last October, he sold the company to AOL for a cool (or ludicrous, depending on your point of view) $25 million and agreed to stay on at AOL as a senior vice-president.

When I heard that Calacanis was sticking around at AOL, and that no golden handcuffs were involved, I couldn’t help but wonder why. For someone now possessing fuck-you money—and a temperament entirely unsuited to the requirements (politesse, org-chart formality, a certain sublimation of ego) of standard-issue corporate culture—what precisely was the point? If it were Yahoo, Google, or even News Corp., well, okay. But AOL? Huh?

And so I am certainly intrigued when an AOL PR woman e-mails, out of the blue, to offer up a meeting with Calacanis for an “advance briefing” on the Netscape project. Intrigued and a bit confused. The last time I heard from Calacanis, he was royally pissed off with me for a column I wrote last year, in which I referred, en passant, to his “Web 1.0 flameout.” “Silicon Alley Reporter did not crash,” he e-mailed, demanding a correction. “We renamed the publication VentureReporter and we sold it to Dow Jones.” This was true, but beside the point—as he realized at the time. In October 2001, the Times reported, “Before the Sept. 11 attacks, Mr. Calacanis had planned a funeral party for his magazine, complete with black-edged invitations and a coffin.” But when I pointed this out to Calacanis, it only made him madder; the stream of irate e-mails continued for two days.

Happily, Calacanis now seems uninterested in rehashing the dispute. Instead, he’s in selling mode. Apart from his outfit—a highly AOL-friendly ensemble of blue blazer, white dress shirt, and jeans—he looks little different (if perhaps marginally better-fed) than he did in the old days. After AOL acquired Weblogs, he says, “I had a lot of free time. So I was talking to Jon Miller, our CEO, and [AOL vice-chairman] Ted Leonsis, and they said, ‘What would you do with Netscape?’ And I said, ‘Oh, we still have that? It’s still around?’ ”


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