Here's Why Jason Calacanis Should Move Back To New York

Jason Calacanis

Photo: Wikimedia Commons

An open letter to Mahalo CEO Jason Calacanis.Jason, I’ve been meaning to write this for a while now. And I know i’m not alone. Consider this a Digital Intervention, and one that may be coming a too late – though I hope not.

First of all – let’s set the stage:  We’ve known each other a long time. Back to the days when you were pure Brooklyn – fighting your way up to create a tech scene in New York.  Silicon Alley was your invention – and with things like the Digital 100 list, you built a power base and gave the nascent NY tech scene something to be part of.  

You had a chip on your shoulder, something to prove, and you could be a bit of a dick, but heck – New Yorkers like it that way. You were at home.

I remember talking with you on a sunny Sunday afternoon at some outdoor watering hole in Soho and you had your bulldog by your feet. You seemed, for a moment, king of the world. Which is to say, happy.

From there – you’ve been more and more successful, and more and more pissed off. You sold to AOL and that was a great transaction that put some cash in your pocket.  You moved west, and with Sequoia’s cash, started Mahalo.

In hindsight, the name Mahalo seems more like you rebranding Jason 2.0. You wanted to be west coast, chill, Napa, tech.  The only problem is – you’re a New Yorker.

And now it appears the transplant didn’t take.

You’ve been roaming the earth looking to pick a fight. Whether it’s telling the audience at Affiliate Summit  that they suck, or the crazy mean email you sent to an exiting employee at Mahalo, it’s like you’ve been begging folks to see how angry you are and how much you’re going to hit the wall.

Now, to be fair,  not all east coast transplants fail in the techno-chill that is the valley.  We all know people who’ve put their inner New Yorker under a bushel and made it big in tech.  But, you can always out them with a casual mention of Zabars’ Nova or good pastrami.  

In your case, it’s time to throw in the towel and move back east.

You’re a fighter in your DNA, and a builder, and an editorial person. There’s plenty of opportunity for your restless, pissed off,  driven alpha energy here on the island of Manhattan.  Frankly, you’d fit right back in.

But if you don’t move back east – you’re heading for a pretty precipitous fall. Suing TechCrunch isn’t a strategy, it isn’t smart, and frankly given the string of tweets you’ve posted about Arrington, it’s just kinda of dumb. You sold to AOL and did fine. Now he’s sold to AOL and he’ll do good work there. For you, there’s nothing but pain in this attack, and for the first time your friends who’ve looked the other way are starting to generally think you’re losing it.

So Jason – here’s what you have to do next.

Drop the craziness with TechCrunch.  You’ve never been a me-too person, and you’re going to have a very tough time getting folks to come to a conference that feels like a grudge match.  Life’s too short – and you’ve to go much to offer.   Second, I don’t get Mahalo.  If you do, it’s time to pay attention to that business and really solve a problem. Otherwise, hand the keys back to Sequoia and stop trying to be four different people.  Third, move back home.  You’re a fish out of water in the valley – you’ll be welcomed back to NY and your whole angry New Yorker thing will fit right in.  Plenty of poker and sushi in this town (as you know well).  Finally, you’ll find that back in New York you’re one of the early guys who embraced tech, and there are lots of folks who would value your knowledge, experience, and frankly smart arse attitude. Join a VC firm, mentor start-ups, blog about the emerging tech scene – any or all of the above. You’ve learned a ton – and there’s a city full of fired up tech companies that could use your help.

Yes, the winters suck.  But otherwise, New York is home. 

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