Ina Fried

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The Multitasking Jack Dorsey on How He Does It

Jack Dorsey has one of the most important jobs in technology. Well, actually, he has two of them.

Dorsey is the CEO of mobile payments company Square and the chairman chief product guy of Twitter, the microblogging service he co-founded.

“They are both changing the world in different but very dramatic ways,” Dorsey said.

As for how he can work two full-time jobs, Dorsey noted he spends eight to ten hours a day at each job, which he admits doesn’t leave a whole lot of time for anything else.

“I don’t sleep much, but it’s enough,” he said.

Dorsey also told the story behind the founding and development of Square–a process that took a month and began with a huge black box that connected to the iPhone’s audio jack.

“It worked and it was amazing,” he said, even of that first prototype. From there, he put the service to the test, trying it out on noted investor Ron Conway. Dorsey showed the idea for Square by swiping Conway’s black American Express card and deducting $500.

Dorsey noted that he later took more money from Conway, though not via Square.

Later, Dorsey took the Square demo–initially called Squirrel–to show Apple the technology. However, as he was at Apple’s cafeteria, he noticed their point-of-sale system was called Squirrel. So much for that name, Dorsey decided, scrapping both the name and the acorn-shaped reader.

Dorsey noted that the goal of the company is to making spending money less of a hassle.

“Payments has never been beautiful,” he said. The typical transaction has too many mechanics, from handing over a card and then signing a piece of paper and then getting a receipt and then throwing that receipt away.

By contrast, he noted that payments are much simpler at places like Starbucks and Virgin America, which focus on the payment experience.

“People hate flying but they love flying Virgin America,” he said.

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The beauty of Twitter is that more and more people are flocking to it because it’s shrinking their world.

— Twitter CEO Dick Costolo