Jack Dorsey: The Tech Mastermind With The Soul Of An Artist

OB-VB836_mag111_OZ_20121024002043Highlighting Excellence from WSJ, by Seth Stevenson

With both Twitter and Square, Dorsey’s flashes of insight are by-products of a lifelong quest for simplicity and order. Dorsey yearns to create streamlined beauty out of giant ungainly systems that at first glance appear to be irredeemably chaotic. He is the Charlie Chaplin of technologists: He makes the impossible happen through efficiency of motion.

Twitter emerged from Dorsey’s teenage obsession with the unruly urban tangle of his hometown, St. Louis. He’d spend hours eavesdropping on the radio chatter from local ambulances. “They would announce where they were and where they were going,” he recalls, “and I realized I could make a computer program that would plot their routes on to a street map.” Before he’d even turned 18, Dorsey managed to transform this effort into software capable of simplifying the whole dispatch process. He set about searching the Internet for the largest dispatch company in the world. When he found it, he quickly hacked into its corporate servers, sent a note to its CEO’s unlisted e-mail address (both announcing the security breach and asking for a job) and then moved to New York to become its lead programmer. This work eventually fed into the creation of Twitter, which lets not just vehicle fleets but regular people broadcast instant status updates—with no need for specialized equipment, and not just across a city grid but across the globe.

Dorsey’s vision is more top down, and of broader scope. He identifies big societal roadblocks and endeavors to unblock them.

Square was invented to cut through the complexities of a different network: the credit card payments industry. Dorsey has an artist friend, a glassblower, whose business was too small to justify the monthly fees and confusing rules and rates of a traditional credit card swipe machine. One day he failed to make a sale on a $2,000 piece because a customer had no cash on her. “That would’ve been enough money for him to live on for a month,” says Dorsey. “The best innovations come out of real problems and real pain. As I was commiserating with him over our cell phones, it occurred to me that we were both holding up to our ears powerful general-purpose computers. I thought there must be some way we could use them to do easy money transfers.”

DORSEY’S OVERARCHING MISSION flows from his urge to unencumber and simplify every corner of his life. For instance, he has no desk at Square. He works standing up at an immaculate, clutter-free table in the center of the wide-open office, typing alone on his iPad, easily accessible to colleagues who can informally sidle up and ask him questions. He leads groups of employees on exploratory excursions to museums or across the Golden Gate Bridge.

It’s important to demystify the term. Innovation is just reinvention and rethinking. I don’t think there’s anything truly, organically new in this world. It’s just mash-ups of all these things that provide different perspectives—that allow you to think in a completely different way, which allows you to work in a different way.

“My personal philosophy,” says Biz Stone, a cofounder of Twitter, “is that creativity is being able to draw upon nonlinear paths to a solution. And the best way to do that is to have some knowledge of a lot of different fields.” Other Silicon Valley entrepreneurs approach their ideas as scientists or mathematicians. But Dorsey is a curious polymath. “Jack is a technologist with the soul of an artist,” says Stone.

When asked which areas of interest he’s eyeing for a potential third act—after communication and payments—Dorsey mentions health. “It’s the most precious thing we have as humans and yet the average person knows so little about it. I don’t know how health insurance works. I don’t know how the health industry works. I don’t know how to diagnose myself. We need new tools.” Perhaps Dorsey, in his head, is already reinventing, beautifying and simplifying another of life’s many thorny thickets.


Read the full article at WSJ, by SETH STEVENSON

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