Flippant Calacanis strikes a typical pose.
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Related StoriesCalacanis's archrival, Gawker Media tycoon Nick Denton, once described him as "brash," "ballsy," "publicity-hungry," and "the Web's answer to Donald Trump," all in the same paragraph. Calacanis prefers to think of himself as honest, authentic--and there's truth to that. He may dish it out, but he's admirably thick-skinned, a necessity in the Hobbesian world of blogs, with its nasty, brutish, and short commentary. Calacanis is indeed transparent, but not only in the sense that his motives are clear (they are: He wants to get rich enough to buy the New York Knicks), but because he doesn't hide what he thinks. As perennial pal Douglas Rushkoff, author of Get Back in the Box: Innovation From the Inside Out, puts it: "Jason would never stab you in the back. He might stab you in the face, though."
The Calacanis saga has been rehashed so often it's like a Web junkie's version of E! True Hollywood Story. Calacanis is the working-class kid who started a grimy, 16-page, black-and-white newsletter, The Silicon Alley Reporter, that he'd stuff into newsstand racks when no one was looking. Early on, he realized there might be a healthy business in providing publicity for New York's burgeoning tech community. And in a dazzling display of catch-22 logic, he knew if these Alley dotcomers became important, he would too--because he would be deciding who was important. His cynicism paid off nicely: Within five years, he was pulling in nearly $12 million in revenue.
With the money pouring in, Calacanis became a schmoozer nonpareil. He rented a loft, threw parties, organized conferences, and published a West Coast version of the magazine. Both Rushkoff and Calacanis held season tickets to Knicks games, Rushkoff sitting a dozen rows in front of his friend. But the ever-restless Calacanis never stayed in his seat long. "He'd start out the first quarter sitting behind me," Rushkoff recalls, "but he'd invariably see someone he knew--a dotcomer, venture capitalist--and by the second quarter would end up sitting in front of me."
By January 1999, as the market was about to peak, Calacanis and Rushkoff sat next to each other on a plane. Calacanis had just been offered $20 million for the Reporter and its associated conference business. But he was torn. Not yet 30, he was still a true believer.
"Take the money," Rushkoff advised. "This is going to end."
Calacanis didn't listen, and when the market tanked so did his business. "Imagine being 30 years old, thinking you were a media titan," he says, "and now you are labeled a scam artist. It made me want to prove they were wrong."
Calacanis began laying the foundation for his second coming. Realizing that some of his best writers from the Silicon Alley days had taken up blogging, he decided to take the plunge himself. But he wasn't just going to start his own blog. He would create an empire made up of dozens--if not hundreds--of one- or two-man publications. If Calacanis had 100 blogs each making $100,000 a year, he'd have a $10 million business. As part of his due diligence, he sought out Denton, who had shown what was possible with the success of Gawker (gossip) and Gizmodo (gadgets). The two met over lunch in SoHo, exchanged pleasantries, and Calacanis told him of his plans.
Soon afterward, the bickering began. Denton took to his own blog, calling Calacanis a "boom-time hype merchant" who "has reemerged as a blog booster. God help us ... the last thing the world needs now is his brand of late-1990s enthusiasm." Calacanis retaliated by trying to steal Elizabeth Spiers, who'd built Gawker into a media phenomenon, but she was making the jump to print at New York magazine. Calacanis is still shaking his head over that one: "If she had listened to me, she would be a millionaire today." (Click here for Spiers's riff on Alan Greenspan.)
Calacanis turned his predatory attention to Peter Rojas, who had conceived the gadget blog Gizmodo and was making serious money for Denton. Rojas was unhappy, saying Denton insisted he write about sex toys and had reneged on a promise to give him equity in the business. When Calacanis offered him the chance to build his own blog--without editorial interference and with a partial stake--Rojas jumped at the chance, and Engadget was born.
"Nick has a reputation for not being trustworthy," Rojas says. "I don't know anyone who would say Jason isn't trustworthy. He feels he is honorable in ways Nick is perhaps not."
Denton, claiming he didn't "really have anything to add beyond what's on his blog," declined to comment.
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