hen Dick Costolo
attended the University of Michigan, in the nineteen-eighties, his major
was computer science, but he was surprised to find that he also had a
knack for improv comedy. After graduation, he moved to Chicago and took
classes at the Second City Theatre. Unlike some of his peers there—Steve
Carell, Tina Fey, Adam McKay—Costolo was not asked to join the
theatre’s house company, and his comedy career dried up. He fell back on
his skills as a coder and founded a series of tech startups, one of
which was eventually acquired by Google, for a hundred million dollars.
In 2010, he became the C.E.O. of Twitter, earning about ten million
dollars in his first year. At a charity event, he ran into Steve Carell,
and they reminisced about their days as bohemian improvisers. “I’m
sorry it didn’t work out for you,” Carell joked.
In
June of 2015, with Twitter’s stock price languishing, Costolo announced
that he would leave the company. (According to the tech press, the
board of directors had forced him out; Costolo maintains that leaving
was his idea.) Three days later, HBO aired the second-season finale of
its half-hour satire “Silicon Valley.” The season ended on a
cliffhanger: the central character, the founder and C.E.O. of a tech
company, was fired by his board. Costolo, a fan of the show, found the
situation uncannily familiar. “I could relate to every person in that
situation—the founder who’s leaving, the C.E.O. who’s coming in, the
employees who are watching it happen,” he said.
Around
that time, Costolo had breakfast in San Francisco with Kara Swisher, a
tech reporter and power broker who has been calgjlldss”
Conversation turned to “Silicon Valley,” the show. “People in the
Valley—at least, the people I know—talk about the show all the time,”
Costolo told me. “Most of them love it, oddly. I think there are a lot
of people telling themselves, with varying levels of accuracy, ‘They’re
satirizing those annoying tech people—not me.’” Swisher, who knows
everyone, was in frequent contact with the showrunners, Mike Judge and
Alec Berg. “I’ll introduce you,” she told Costolo.
The
next month, Costolo had lunch with Judge and Berg in Los Angeles. They
told him that they had written themselves into a corner. Their show was
about an entrepreneur striving to build a company; having separated the
entrepreneur from the company, they weren’t sure how to proceed. For a
show that devotes a good amount of time to slapstick and gross-out sight
gags, “Silicon Valley” is deceptively well-researched, and Judge and
Berg had decided that the best way out of their bind was to hire a
consultant who could give them more information. To their surprise,
Costolo expressed interest. “We just need someone who knows how these
companies work, not someone who actually ran one of them,” Berg said.
Despite being overqualified, Costolo got the job.
Dick Costolo, the former C.E.O. of Twitter, was one of more than two hundred consultants on the show.Photograph by Scott Olson / Getty “Silicon
Valley” is mostly filmed on multiple sets, inside a concrete Sony lot
in Los Angeles—not in Silicon Valley, but in the same time zone. Every
Monday morning for three and a half months, Costolo flew from San
Francisco to L.A., took an Uber to Culver City, dropped his overnight
bag at a nearby hotel, and spent Monday and Tuesday in the writer’s
room. Berg, Judge, and ten writers peppered him with questions, both
narrow and existential. Where would the most powerful person in a
boardroom sit? Wh
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