Jason Calacanis matters

I’ll point to the New York Times story on Jason leaving AOL. Jason pointed to it also, but promises more later today. A few months ago, at Wikimania, in serendipitous fashion, Jason and I found ourselves in a conversation with a young online media entrepreneur being provided some sage advice by a legendary (and occasionally controversial) tech pioneer who was helping the young media person sort throw a highly-visible controversy he was going through. Until that point, my perceptions of Jason had been via his blog, which, at times can be biting and opinionated and off-putting, but always lively and insightful. In that instant, I witnessed the qualities of Jason that aren’t always apparent in his public persona, but which greatly impressed me in that moment: a genuine concern for the well-being of this young person and the willingness to freely and sympathetically share advice garnered from great failures and successes.

“You’ve got to be willing to walk away. Don’t be afraid to move on.” was one of the wisest things Jason said in the 30 or so minutes we spent chatting with this young entrepreneur and the sage technology pioneer.

When the most recent publicity regarding some changes in the management of AOL began to swirl in the last few days, I thought back on that conversation and wondered when, not if, but when, Jason would move on to the next great thing he’ll do.

Best wishes, Jason.

Photo taken at Wikimania, August 6, 2006, Harvard Law School.

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