Twitter's Jack Dorsey Just Took A Lightning-Quick Trip To New York

Jack Dorsey Busy

We always watch the comings and goings of Twitter chairman and Square CEO Jack Dorsey with great interest.

Just last month, he tipped us off to Square’s plans to raise a huge new round of funding from a couple of big East Coast mutual-fund companies with an unusual trip to Boston and Baltimore.

So what does it mean that he just took a weekend trip to New York to speak at a private school, watch a Yankees game, and dine with fashion doyenne Diane Von Furstenberg?

Yes, Dorsey is bicoastal, with places in New York and San Francisco, but his trips to New York have seemed rarer since he returned to Twitter in an active executive role in 2010. Maybe he’s got more time to travel—we recently heard he’s backed off a bit on Twitter to focus on running Square.

Here’s our theory, courtesy Dorsey himself: “Life is too short not to be direct.” So when Dorsey tweets, he’s sending a message. We just haven’t decoded this one yet. Any theories? Share them, please.

Jack Dorsey always drops hints when he tweets.

He took the Virgin America redeye. (Square PR manager Katie Baynes previously worked at Virgin America. Plus it seems like Dorsey's style.)

Dorsey spoke at the Pingry School's 150th anniversary.

CAA talent agent David Bugliari arranged the chat.

Back when he was a bike messenger, Dorsey totally fit the Williamsburg mould.

He couldn't resist touting Square's payments service, which lets merchants in open-air markets take credit cards.

He made time for the Yankees. (He's a Cardinals fan, though.)

Then dinner with Diane Von Furstenberg, the fashion designer who's married to IAC chief Barry Diller. We bet they're buddies from Sun Valley, Allen & Co.'s retreat for media and tech moguls.

And that was it. Just a Saturday and a Sunday in New York.

Wheels down. It's like he never left.

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