Why Jason Calacanis matters: He could be the new Ted Leonsis — and more
Steve Case was not the soul of AOL. The founding chairman was squeezed out because, frankly, he didn't fit the culture. The real man running AOL was vice chairman Ted Leonsis. Dot-com scribe Michael Wolff writes in his book Burn Rate that when AOL brought in Leonsis,
Case became...the suit, and Leonsis became the visionary...He could talk the talk, he could sell the vision thing. He was creative, motivational, combative. He was everywhere...furiously insisting that AOL was what he wanted it to be, rather than what it was.
People believed him...You couldn't help thinking that what he was saying had to be true, that otherwise he'd never have the guts to stand up there and say it and huff and puff like that.
Sound familiar? That's the same reaction executive Jason Calacanis gets from many who read his personal blog.
He "has guts," he's a "very brave man." Every move he makes — calling for AOL to stop recording searches, having the nerve to hire his competitor's top users — wins more converts to the Jason Calacanis Fan Club. When journalist Paul Boutin went with Jason to a small press conference (a dozen reporters talking to Google co-founder Larry Page and CEO Eric Schmidt), he was impressed with Jason insisting to Eric that Google must be working on an operating system. As far as we know, Jason was dead wrong — but that didn't matter.
Like Ted Leonsis, Jason entered AOL through an acquisition. The company bought his blog network, Weblogs, Inc., in 2005. They expanded his power by putting him in charge of relaunching Netscape.com — a lousy gift, given the crochety user base that resisted his changes. But he stuck through it, proving to AOL that he's brave and tenacious. And what seems more important at AOL — getting it right the first time or risking the brand time and time again to chase new profits? Netscape was already dying, and even the most painful changeover could at least change the user base to a younger, more marketable crowd.
Jason is unafraid to point out his company's failures. We don't know how well this attitude fares within AOL, but publicly it's winning him much respect.
For example, a tired Leonsis blogged about AOL's recent massive leak of millions of user search records. "I personally feel just awful about it," he wrote in a one-paragraph entry.
Meanwhile, Calacanis wrote a full-page entry on how angry the "hard times at AOL" made him, and how hard it is to heal the damage done by the privacy violation or "the call" (a reference to the famous customer service call in which a rep refused to cancel a user's AOL account). His emotion could be real or rhetorical, but either way, he seems like a man on a mission to fix "his" company.
And he may get the chance. "Somebody's got to be the next CEO of AOL," Jason told himself while talking to Wired Magazine. "Why not you?" He even pointed out a video of AOL CEO Jonathan Miller calling Calacanis's hire part of AOL's "succession plan." That was a joke, said Calacanis, who regularly makes the same joke on his blog. But a big joke, told often enough, becomes true.
