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.
He took the Virgin America redeye. (Square PR manager Katie Baynes previously worked at Virgin America. Plus it seems like Dorsey's style.)
He couldn't resist touting Square's payments service, which lets merchants in open-air markets take credit cards.
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.
Business Insider Emails & Alerts
Site highlights each day to your inbox.