by Vanity Fair
March 3, 2011, 12:01 AM
“It was like being punched in the stomach,” Jack Dorsey, who invented Twitter, tells Vanity Fair’s David Kirkpatrick about losing the job of C.E.O. “Twitter held all my desires in the world,” he says, displaying rare candor in his first full-scale profile.
Now Dorsey dreams of one day becoming mayor of New York. According to Kirkpatrick, he has already discussed his ambition with the man who currently holds the job. Bloomberg advised the younger entrepreneur, whose fortune may well exceed $300 million, to make a lot of money first. Dorsey already has the endorsement of Newark’s mayor. “Frankly, I’m in awe of him,” says Cory Booker.
Dorsey has been obsessed with cities, and getting around in them, since he was a child. “I just had a meeting I’ve been wanting to have since I was 14,” he says of an appointment with the head of the Taxi & Limousine Commission to discuss putting Square technology into cabs. “This was my first passion. This is the reason for so many things in my life,” he says. The idea for Twitter grew out of Dorsey’s interest in the way cabdrivers and dispatchers communicate their location through short radio and mobile phone messages. “Dorsey suggested that his company create a service that would allow anyone to write a line or two about himself, using a cell phone’s keypad, and then send that message to anyone who wanted to receive it. The short text alert, for him, was a way to add a missing human element to the digital picture of a pulsing, populated city,” Kirkpatrick writes. “What gets me really energized,” says Dorsey, “is thinking about activity within a city. Like, even this intersection at the end of Fifth Avenue, seeing all the taxicabs turn. There’s such a rush of energy constantly coursing through.”
Dorsey admits that his failure as a manager was a factor in his ouster from Twitter. “I let myself be in a weird position because it always felt like [Evan Williams’s] company. He funded it. He was the chairman. And I was this new guy who was a programmer, who had a good idea. I would not be strong in my convictions, basically, because he was the older, wiser one,” he says. “It just got a lot bigger a lot faster than anyone expected,” says Williams, who became C.E.O. after Dorsey but stepped down in October 2010. “A year and a half later we’d raised $20 million, and the servers were crashing every day…. It wasn’t so much that the ship was sinking, but more ‘Great job, Jack—we’ve got to up our level of experience and lay some foundation for a much bigger organization.’”
Dorsey, who according to Kirkpatrick texts his mother first thing every day, speaks with a schoolboy’s enthusiasm about his latest project, Square, a device that allows users to collect credit-card payments using their smartphones. “Payment is another form of communication,” he tells Kirkpatrick, “but it’s never been treated as such. It’s never been designed. It’s never felt magical. About 90 percent of Americans carry cards, but almost nobody can accept them. We want to balance that out and just make payments feel amazing.” “Even the way he talks about Square is about social justice,” says Booker, who used the system to accept matching donations to the city of Newark.
“What makes Jack magic is his precision,” says Ashton Kutcher, explaining his friend’s facility with the short form. “When he speaks he makes every syllable count.” Another celebrity friend, Alyssa Milano, expounds on Dorsey’s humility. “He never really says what he does for a living,” she tells Kirkpatrick. “I’m usually the one bragging about his achievements.”