You Only Have to Be Right Once

You Only Have to Be Right Once by Randall Lane Page B

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Authors: Randall Lane
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million businesses are upending the financial services industry; in 2013, Square exceeded $500 million in revenue.
    Those companies have made Dorsey a billionaire. His stake in Twitter, after the 2013 IPO, was worth more than $1 billion. In that same year, his share of Square, based on funding valuations, also neared a billion.
    Before he cocreated two of hottest tech companies on the planet, Dorsey gave little sign of brilliant focus. He wrote dispatch software for ambulances and cop cars, dropped out of college (twice), took up botanical drawing, became a certified masseur and, later, dabbled in fashion design. More recently he has made noises about becoming mayor of New York City. His mother sometimes despaired he would ever find himself.
    But he knew better. The side trips are part of the road map; his discursiveness is the obverse of intense discipline. Dorsey is a serial wanderer, mentally and physically, because it helps him concentrate: “The best thinking time is just walking.” He has worn a trench between Square, his previous apartment around the corner, and the offices of Twitter, a few blocks away. Before he starts his day, he runs three to five miles. He likes to take new recruits on tours of San Francisco.
    Management by wandering around was made famous thirty years ago by
In Search of Excellence,
the book that celebrated the leadership and innovation of entrepreneurs like Bill Hewlett and David Packard. Dorsey has his own brand of “loose-tight properties”—autonomy on the shop floor but working under centralized values. Pay attention to the smallest things, Dorsey frequently says, while keeping sight of what’s truly important.
    The guy focuses not only on breakthrough ideas but also radically different kinds of corporate structures to contain and develop them. Wittingly or not, Dorsey provides an original model of how to start and run a company.
    â€¢Â â€¢Â â€¢
    DORSEY GREW UP IN St. Louis, the oldest child of Tim and Marcia, who are clearly his biggest fans. In September 2013, they flew out to see their son speak at the Techonomy Detroit conference. And Jack, hardly innocent of the spotlight, confessed to pregame jitters backstage. Why? “My mom and dad are here.”
    Tim, who runs a small company called MA Tech Services, which makes mass spectrometers, reported that he is an avid Tweeter (@Tim535353). Jack’s younger brothers tweet, too: There’s Daniel (@darkside) and Andrew (@andrew), who writes on his home page, in blaring caps-lock-style, “U AINT COOL TILL U ON TWITTER.”
    Even Marcia tweets. @marciadorsey’s page says: “Mother of @jack . . . Does that make me the grandmother of Twitter?”
    As a kid Dorsey was captivated by iMaps and the cities they described. As a teen he became interested in the dispatch services used by taxi services and other transit systems. At sixteen Dorsey tried to start his own bicycle courier service, in part to have an excuse to write code to run the business—until he found little demand for bike messengers in St. Louis.
    A self-taught coder, Dorsey graduated in 1995 from Bishop DuBourg High School, then enrolled at the University of Missouri-Rolla but didn’t stay long. Still fascinated by systems, Dorsey discovered a security flaw in a website operated by a New York City company called Dispatch Management Services, run by Greg Kidd. Dorsey found Kidd’s e-mail address on the company’s computer system and sent him a note alerting him to the flaw. Kidd immediately offered Dorsey a job, and he bolted from Missouri for the Big Apple.
    While in town, Dorsey enrolled at New York University. Though he’s now clean-cut and often dressed in Prada suits, Dorsey in those days wore a nose ring and dreadlocks (he still sports tattoos under the expensive threads), and spent free time in the East Village listening to punk bands like Rancid. Kidd and Dorsey went on to start a new company

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