Before embarking on a career as a technology entrepreneur, Dick Costolo took part in an improvisational comedy troupe in Chicago that relied on quick wits to spontaneously prove any wild theory that the audience could dream up — say Jim Morrison wrote all of Beethoven’s symphonies or pop-up umbrellas caused the downfall of the Mayan culture.
Costolo is still the king of quip even as he settles into his new role as a start-up straight man for Twitter Inc. in San Francisco.
His first update on Twitter after joining the popular Internet service as chief operating officer in September 2009: “First full day as Twitter COO tomorrow. Task #1: undermine CEO, consolidate power.”
A year later Costolo, 47, replaced co-founder Evan Williams as chief executive.
Now it has fallen on Costolo to help Twitter make the transition from popular service to profitable moneymaker. Costolo has heard all the jokes about how Twitter can’t make money. And he’s determined to get the last laugh by rolling out advertising campaigns that are drawing serious interest on Madison Avenue.
As a teenager, Costolo learned to program games on a Radio Shack computer that he got from his dad, an engineer for Pontiac. He majored in computer science at the University of Michigan but needed arts credits to graduate. So he started taking theater classes during his sophomore year. By his senior year, he was rocking the open mike in the student union. After graduation, instead of leaping at offers from big computer companies, Costolo decided to improvise — literally. He moved to the home of improv: Chicago.
One of his most popular gigs was “Modern Problems in Science,” in which three comedians would ask the audience for absurd scientific hypotheses and academic disciplines such as professor of Russian literature, meteorology or ichthyology (the study of fish). They would then have to use those disciplines, and plenty of mumbo jumbo, to prove that Earth is shaped like a giant burrito or that Keanu Reeves’ success is the source of all global conflict.
In 1994 when the Netscape browser debuted, Costolo realized that big things were about to happen on the Internet. He got serious about technology again and pulled off a string of successes, starting and selling three companies — the last one, FeedBurner, to Google Inc. in 2007 for $100 million.
After a few years with Google in Chicago, Costolo decided to strike out on his own again and move west to be in the middle of the tech action. He was dreaming of launching another company.
Twitter co-founder Williams, a longtime pal, sent a private message to Costolo on Twitter asking if he wanted to fill in as CEO while Williams was on paternity leave. The offer of an interim gig soon turned into an invitation to join Twitter as a top executive.
“There are a handful of Internet companies with this kind of potential. I would have been foolish not to do it,” Costolo said.
Now Costolo is running the show, ramping up Twitter’s advertising strategy, while Williams is focused on improving the experience for Twitter users. Costolo likes to use phrases like “operational efficiency.” Williams, not so much.
“I bounce ideas about operations off of Ev. He bounces ideas about product off of me. But we both have our preferred focus,” Costolo said.
Costolo says he’s officially retired from the comedy circuit, even if he’s still trying to get laughs.
TechCrunch founder Michael Arrington at the Crunchies technology awards this month asked Costolo what he thought of the news that Google Inc. CEO Eric Schmidt planned to step down in April.
“Eric is on a bit of a different plane than me. I mean in the Gulfstream sense, not the other sense,” Costolo joked.
And Costolo is turning in virtuoso short-form performances on Twitter, which limits messages (and jokes) to 140 characters. “Twitter board meeting: proposal to limit use of the letter ‘K’ in tweets is rejected. Next topic: is it legal to tweet from below sea level?”