Dick Costolo: CEO goes from Chicago comedy to Twitter's IPO big stage

It’s a pretty typical story:

A computer science major who dabbled in standup and improvisational comedy at the University of Michigan moves to Chicago, takes classes at Second City, performs a bit of stand-up and many improv shows around town (at Annoyance Theatre and elsewhere) and is instrumental in establishing three tech start-ups during the first Internet boom.

He sells one of those start-ups – FeedBurner – to Google in 2007 for a reported $100 million, gets a healthy chunk of change from that deal, spends two years thereafter as a Chicago-based Google employee, decides he loathes Chicago’s extreme weather, splits for the west coast and accepts a pal’s invitation to become chief operating officer at the San Francisco-based micro-blogging site Twitter.

Soon he ascends to the position of CEO, institutes changes that improve internal operations and increase ad revenue and helms an initial public offering that will make him much richer than he already is.

OK, so it’s not a typical story. But it is Dick Costolo’s story.

Come Tuesday, the 50-year-old Twitter honcho of three years, married father of two and CrossFit enthusiast stands to profit handsomely when Twitter launches an estimated $1 billion IPO. In addition to earning roughly 400 times his initial $25,000 Twitter investment made in 2007, Costolo’s 1.6 percent stake in the company could be worth nearly $190 million on a top-end $20 billion valuation.

In this 2006 image, the FeedBurner co-founders gather at the company headquarters on Randolph Street. From left, are Steve Olechowski, Dick Costolo, Eric Lunt and Matt Shobe. | Sun-Times file

A Twitter spokesman, citing IPO “quite period restrictions,” said Costolo (whose handle is @DickC) was unable to talk for this story.

According to his longtime friend and colleague Eric Lunt, a former partner (one of three) in the Google-acquired FeedBurner and now chief technology officer at the Chicago-based firm BrightTag, Costolo is low-key when it comes to money.

“He’s never been one for outward shows of wealth or status,” said Lunt, who describes Costolo as “completely straightforward, genuine, authentic.”

The two met in the mid-1990s when both worked at Anderson Consulting (now Accenture) and Costolo was still staging shows such as “Modern Problems in Science,” which one complimentary reviewer described as an amalgam of “sarcasm, outrageous puns, digressive story telling” and “exceptionally complicated diagrams.”

Erstwhile Costolo collaborator Rich Fulcher also recalls an Annoyance production titled “Abraham Lincoln, Sex Alien” in which they played “two intergalactic travelers who became upset with Abraham Lincoln’s sexploits.”

Their roles called for them to wear “buttocks as heads.”

**

Before relocating to Chicago in the mid-1980s, Costolo studied computer science in Ann Arbor merely because he wanted to earn a degree that he could “actually do something with.” But improv and comedy were his first loves, so he turned down three job offers to follow his dream — and, as he joked to graduates during a U. of M. commencement speech in May, achieve “ultimate fame and glory” on “Saturday Night Live.”

The “real world” story of what happened, he told them, was far less glamorous than the romantic Hollywood version. Rather than suffering mightily for “about three minutes” before showbiz stardom commenced, he spent years “grinding away,” performing for free and doing odd jobs — including “wrapping flatware and selling place settings” at Crate & Barrel — to make ends meet.

Two of the most important insights Costolo received during that period were gleaned from legendary and now-late Second City improv instructors Don Depollo and Martin de Maat. The former encouraged his students to “make bigger choices, take courageous risks.” The latter pushed them to exist in the moment onstage and warned against hewing too closely to a script.

“If you try and plan what the next line is supposed to be,” de Maat said in Costolo’s remembering, “you’re just going to be disappointed when the other people onstage with you don’t do or say what you want them to, and you’ll stand there frozen.”

Costolo took those lessons to heart, employing them in business and life.

**

In 2009, five years after Lunt introduced him to Twitter co-founder Evan Williams, Costolo left Chicago with his family to join the increasingly popular but financially struggling outfit in California’s Silicon Valley. “First full day as Twitter COO tomorrow,” his first on-the job tweet read. “Task #1: Undermine CEO, consolidate power.”

By October of 2010, he’d done just that — minus, presumably, the undermining.

In his leadership role, Lunt said, Costolo’s well-honed sense of humor is a definite advantage. Aside from being “a hedge against his own intensity,” it helps him to communicate points and priorities “in such a way that doesn’t make people defensive.”

Had he instead chosen to focus his energies on comedy performing, Fulcher thinks, “We would have seen him on SNL or [in] film.”

Perhaps sporting a rump on his head.

MORE: See who else is about to be really rich off Twitter’s IPO.