Over-Employed Jack Dorsey Spending His Days On The Streets Of San Francisco

Two CEO gigs and zero desks is how Jack Dorsey do.

With 2015 winding to an inexorable close, we wanted to check in on one of our favorite bros from this year.

So how is Jack Dorsey doing with all those jobs?

Twitter Inc. ’s executive chairman, Omid Kordestani, struggled to find time in Jack Dorsey’s jam-packed schedule for their weekly chat. So he offered to be the CEO’s driver for the day.
On a recent morning, Mr. Kordestani weaved through Silicon Valley traffic in his Tesla Model S as the pair talked business.
“We just maximize every hour we can, however we can do it,” Mr. Kordestani said.

Just two tech millionaires in a Tesla, driving around Frisco and talking management...Damn, Jack, can't you stop being so relatable all the time?

Well, we knew that he'd be crunched for time. How is Jack managing to keep his fingers in all those pies when he isn't being chauffeured around by important executives whose time would likely be better spent back in the office running things in his absence?

He typically starts his days with coffee at Blue Bottle, located between the two headquarters. According to Twitter and Square, on Monday morning, Mr. Dorsey arrives at Twitter for five-hour meetings with his eight senior executives and Mr. Kordestani to review the business operations and projects. At 1:30 p.m., he rushes over to Square to repeat the same exercise. Mr. Dorsey tells executives to put their phones and laptops away—he has no office or desk at either company.

So, basically Jack's life has become a steroidal version of "Groundhog Day" meets "The Social Network" played on loop in his head. Cool.

At least he doesn't have the encumbrance of, like, a workspace to make him feel existentially and physically trapped.

But let's big picture this. Forget "Jack," how is Jack doing in his heart?

Mr. Dorsey, 39 years old, isn’t married and doesn’t have any children unlike Messrs. Jobs and Musk. He will likely have little free time as both Twitter and Square are at critical junctures. Twitter is working to show frustrated investors the social media service has mass-market appeal. Square is trying to prove it can expand beyond the intensely competitive payments space. Neither is profitable.

Merry Christmas, Jack Dorsey, you miserable sonuvabitch.

How Jack Dorsey Runs Both Twitter, Square [WSJ]