Suit 2.0

Photo: Illustration by Christopher Sleboda

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?’ ”

Calacanis swivels on his chair, fires up his laptop, and gives me a lengthy demo of the answer to his bosses’ question. The new Netscape will look familiar to anyone who’s spent time on, the ultra-trendy social-news site that focuses mainly on tech. Like Digg, Calacanis’s new baby lets users submit news stories or blog posts, then sorts and ranks them according to their popularity (as determined by users’ votes). But unlike Digg, Netscape will focus on all categories, from sports to entertainment, and it will also employ a clutch of commentators who will follow up on the most popular stories with fact-checking or analysis. Calacanis dubs these people “anchors,” not editors, “because they’re not editing people’s work,” he says. “They’re going to do metajournalism.”

Few will dispute Calacanis’s argument in favor of a layer of editorial involvement on top of pure social news: “The wisdom of the crowd often gives way to the madness of the mob,” with false stories rising ever higher in the popularity queue. (Whether bloggers on top of bloggers is the answer is another matter.) And the site that he and his team have hacked together is impressive, incorporating countless other au courant Web 2.0 features (user “tagging” à la; video à la YouTube). But to take a brand as venerable as Netscape—which to most minds that still even recognize it will always be synonymous with Web browsers—and transform it into something new will not be easy.

Rather than scheming to topple the powers, they scheme to get bought and then dig in for the long slog to the top.

Yet Calacanis argues that these shortcomings are offset by Netscape’s reach. Even after years of atrophy, the site still has more than 11 million unique visitors each month. “It’s a monster,” Calacanis says. And he insists that he sees its revivification as a kind of holy quest. “The brand means a lot to me,” he says. “I sort of take it as a noble mission to bring it back.”

Even among Calacanis’s friends, noble missions are not routinely described as his stock-in-trade. I ask him whether doing something like this is why he decided to stay on at AOL. “When they bought Weblogs, they said to me, ‘There’s a real future for you here,’ ” he says. “I’m a senior vice-president, which is a pretty high title in this company; there’s only one title, EVP, that’s higher, and then after that you’re the president of a division. I have absolute access. I went to dinner with Jon Miller the other night in L.A., and I hang out with Leonsis, I go to Wizards games with him. [Leonsis owns the Washington Wizards.] So I’m pretty high up.”

Being high up has always appeared to matter a great deal to Calacanis. From the earliest days of Silicon Alley Reporter, his avid gadflyism has always seemed driven by a naked (and even refreshing) eagerness to shimmy up the greasy pole. What’s different about the current Internet boom, however, is that the old pole no longer exists. In the nineties, the dream for any self-respecting entrepreneur (a label that Calacanis is, with justification, quick to affix to himself) was to create an empire from scratch: start a company, take it public, build it into a behemoth. But since the crash, the IPO window has remained slammed shut (with the case of Google being the exception that proves the rule).

All of which is no problem if your goal is simply to get fat. Then you just sell out. But what is someone like Calacanis supposed to do? Someone who dreams of being the next Eisner or Diller but who’s smart enough to see that hurling himself into the old-media fray is obviously a losing proposition? In truth, the options are limited—which in itself is interesting. What’s been clear for a while now is that Web media is consolidating around a new Big Three or Four or (being generous) Five: Google, Yahoo, Microsoft, AOL, and Diller’s Ask. Sure, the blogosphere is teeming with energy and proliferating wildly. But if you want to be a bona fide mogul, with all it entails, the number of available avenues is severely constrained.

And so Calacanis’s decision to stay at AOL isn’t actually all that hard to grasp. Indeed, you might say it’s a sign of the times—times in which, in this respect, new and old media are looking ever more alike. As Google, Yahoo, and the other Web powers take their place as the big kahunas of advertising and marketing, they’re increasingly the repository of the strivers and climbers who used to flock to broadcast and print. Rather than scheming to topple the powers with some disruptive technology, they scheme to get bought and then dig in for the long slog to the top. Consider Calacanis’s stated rationale—calculating and needy in equal measure—for preferring AOL to Yahoo: “If I’d landed at Yahoo, I’d be hanging out with [ founder] Josh Schachter and [Flickr founder] Caterina Fake, debating the finer points of this stuff. But at AOL, I’m probably the most knowledgeable person on this area, so they really needed my help.”I ask Calacanis if he ever feared that AOL would buy Weblogs and then screw it up. “No,” he says. “And in the worst-case scenario, whatever, no reason to cry for me. I could start a company tomorrow.

I get ten calls from VCs every week asking me what’s my next company. I say, ‘I already have a new company—it’s called AOL, LLC, and it’s going to be really big!’ ”

Calacanis laughs, and so do I. But then I wonder if the joke will be on him, as it was on Marc Andreessen.


Suit 2.0