Jason Calacanis, AOL executive, 2005-2006

Jason Calacanis, the energetic and annoying publishing entrepreneur who once thought he could rise to the top at AOL, is leaving the internet media company. He's not commenting on the record, but his blog describes Jonathan Miller, ousted CEO of AOL, as his mentor, and Miller's departure as a sad day. He's out.

Calacanis first came to notoriety as an internet promoter in the late 1990s as the founder of Silicon Alley Reporter, a print magazine which fulfilled in New York the same role as Silicon Valley's Red Herring. At the height of the boom, Calacanis brushed off a rumored $30m offer for the title by Time Inc., though accounts of that approach vary.

Despite the brutal downturn — personal debt incurred in financing the magazine, the print title's eventual closure, and the sale of the remnant company that was face-saving rather than financially rewarding — Calacanis quickly bounced. That is, in face, his most defining characteristic. He's suffered reverses that would send most people back to their mothers, and he always recovers. It's really rather impressive.

After a false start publishing internet trade blogs under the Weblogs Inc. banner, Calacanis finally found business success with consumer-oriented web titles such as Engadget, Autoblog and Joystiq. Disclosure: Calacanis hired away the founding editor of Gizmodo, a Gawker Media title, in establishing Engadget. Gawker and WIN compete, head-to-head, in gadget, auto and videogame coverage.

Calacanis wasn't about to, second boom around, wait too long to sell. WIN, Calacanis' typically bullish abbreviation for the company, was acquired last year by TIme Warner's AOL for about $25m. The proceeds were contingent on traffic and revenue growth, and shared, not least with Brian Alvey, his oft-forgotten co-founder. But WIN's sale was Jason's first big payday, and it gives him the personal resources, a burnished reputation and a track record with which he can now raise venture funding.

The surprise, after the sale of WIN, was that Jason Calacanis stayed around so long. His payoff was not contingent on continued involvement with WIN. He's a gadfly, unsuited to major corporations but, for a brief moment, the chippy Brooklyn underdog seemed to enjoy his status as a corporate executive at a glamorous media company.

Calacanis took over Netscape.com, an atrophying brand that AOL had picked up in the late 1990s, and was trying to turn it into a clone of Digg, the popular linkdump. Calacanis even wrote, unwisely, of his ambitions to become CEO of AOL one day. Just yesterday, he wrote in a news tip, on IM: Calacanis is getting a huge raise and bonus at the end of the year.

But I suspect that Miller's departure will prove a convenient exit for Calacanis. He faced an uphill struggle to turn around Netscape.com, and seemed to enjoy the gathering frenzy around Web 2.0. For him, especially, it can't have been easy to sit out the bubble, rewarded only by salary and big-company stock. Miller's exit provides news cover.

So, what next? My guess: a rapid re-entry, with a well-funded venture in internet media, probably podcasting or wiki directories, judging by the topics Calacanis covers in his personal writing. He'll be loud, infuriating — and probably, irritatingly, successful.

Contact information for this author is not available.