The Unsurprising Departure of Jason Calacanis

17 Nov ’06

It’s perhaps unfortunate for Jason Calacanis that his departure from Time Warner-AOL coincided with his old competitor Nick Denton taking over the reins at Valleywag – one of Denton’s first tasks there was to rub salt in the wound over the departure. The story is that Calacanis left AOL after Miller’s ouster – either as protest, I suppose, or because the departure of a man he describes as a mentor took the fun out of the job for him – more on that below. But in any event, Denton then promptly posted a story on the deletion from Calacanis’ blog of a comment criticizing Miller in pretty ugly terms.

To my mind, though, another Valleywag post is a more interesting indication of what this story is about. Denton posts on the general ugliness inside Time Warner & AOL, and what seems like a sad tale of un-leadership. Gist:

As recently as Monday, Jeff Bewkes appeared on a stage at an AOL offsite and told the assembled that Jon was his guy and that he was happy with the way things were going. On tuesday afternoon the rumors start to fly, Miller is getting calls from reporters saying that he is out, he calls Bewkes (note: most decent people who have to fire someone actually reach out and make the contact) and Bewkes tells him the rumors are true. So Bewkes lied to the top management at AOL and didn’t have the guts to even call the guy he was firing.

We’ve seen this movie before, of course – just about everywhere. It reads to me like just another day at ABC BigCorp. I won’t stray too far into a discussion of the generally pathological behaviour of otherwise ordinarily competitive individuals when they’re immersed in large corporate cultures, but for now suffice it to say that it must come as no surprise that a guy as entrepreneurial as Calacanis has no interest in playing in that particular sandbox. (Mathew suggests that Netscape might not have been going that well, and I suppose, that this could have hastened Calacanis’ exit, but I’m not so sure – doesn’t it still take more than just a few months to establish global domination, or has YouTube rewritten that rule, too?)

Staci Kramer picks up the thread here with what struck me as outrageously sane comments:

But we’d already heard that Jason was planning an exit—one source who is not directly involved said he already has backing for a new venture. And, as someone familiar with the situation told me, “he’s an entrepreneur and everyone knew going into that this would be the outcome.” Indeed, his stay at AOL was longer than many would have predicted, largely because he was given the chance to do new things like revamp Netscape.

This I can understand. If you have a burning desire to build, why build someone else’s dream? The only surprise, I suppose, is that he lasted that long at AOL (I’d always suspected that he had to, but Denton says no). In a comment here last year, he said he was enjoying the Netscape project:

I could have left AOL and done this on my own with a new domain name. However, I’m part of the senior management team at AOL and enjoying it. They’ve been treating me really well, and for now I’m gonna stay here and enjoy the ride.

A breather, perhaps, after a wild ride, and an opportunity to get busy and let the creativity percolate.

Denton’s (really, rather graceful) epitaph of Calacanis’ time at AOL has a nice finish:

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.

Mathew wonders what’s next, too, and has a suggestion:

I for one will be interested to see what Jason comes up with next. I think he should get some VC money together and convince Mike Arrington and Om Malik to set up shop together as a blog/advertising network, and maybe roll some other sites in there too — like Techdirt for example. Slam dunk, Jason. Call me.

Hmmm. Well, I have an idea too – not any of those, but something that I think would be a lot of fun. Well, as much fun as you could have grabbing Old Media upside-down by the ankles, and shaking out all of its money in a pile in front of you. Jason – call me.

One last observation – with Denton at Valleywag, is the market for ValleyScoops heating up? Arrington appears to have had this story first (and in an ironic turn, the old gray lady reports that he had the scoop), but it looks like Om, PaidContent and Denton all had the rumours as well, and everyone seems to have tumbled down the courthouse steps in a rush to report. Game on.

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