Wired has a revealing profile of Jason Calacanis, the first to make millions by selling his blog business.
Here’s some background information from the story:
The story of Calacanis’ rise in New York’s new media world goes like this: A bartender and a nurse in the outer reaches of Brooklyn have three sons. The middle one, Jason, puts himself through college at Fordham University, moves into a Manhattan apartment, and starts dabbling in computers and the early Internet. By 1996, he’s figured out that he loves content – “software is so one-dimensional; it’s not as much fun” – and begins publishing a 16-page social register-cum-technology newsletter called the Silicon Alley Reporter. He photocopies it himself and hand-delivers it to coffee shops and other digerati-haunted locales.
Thanks to good timing and aggressive promotion, the magazine catches on. It becomes a must-read for Manhattan’s new media elite. CEOs and VCs vie for positions on its annual Silicon Alley 100 list. Calacanis throws huge, lavish parties. He publishes a sister magazine for the West Coast called Digital Coast Reporter. He charges people $1,000 a head to attend his conferences. His staff grows to about 70. Calacanis becomes the insiderest of insiders, partying with – and selling ads to – the tech icons he’s writing about.
Here’s some journalistic assessment of the Weblogs, Inc./AOL deal, followed by a look at the man’s glaring ambitions and personal style:
So while Calacanis and a few other blog types insist that AOL’s rumored buying price is completely reasonable, it’s not clear that $25 million is a sane amount for 10 disconnected employees and a network of bloggers who could jump ship at any moment. Acquisition valuations for traditional media companies are usually equal to revenue, while a really hot property might get one and a half or twice that, according to Forrester Research analyst Charlene Li. Calacanis got vastly more than that, making it hard not to think “bubble.” Even he tempers his assurances – just a tad. “I can feel a little bit of froth today,” he says. “Not a bubble, but froth.”
Not that Calacanis is going to spend a lot of time worrying about it. For now, he’s happy to drive waiters nuts with picky double macchiato orders and to rhapsodize nonsensically about how he’ll use “citizens’ media,” as he calls blogging, to turn the publishing world on its head. Calacanis says he wants to “poach The New York Times’ best writers” and insists that his writers, many of whom do not earn a living wage as bloggers, think he’s a sucker. “They say, ‘You’re going to pay me to write about Macs? I love Macs. You’re going to make my hobby 30 percent of my income!'” Calacanis is annoyed by writers he considers old-guard. He mimics them complaining: “‘Where are my benefits? Who’s editing me?'”