Twitter CEO Costolo on Improv, VCs and Burritos

Dick Costolo. Photo by Albert Gea, Reuters
Dick Costolo. Photo by Albert Gea, Reuters

Long before taking the helm as CEO of Twitter, Dick Costolo was an aspiring comic at Chicago’s famed The Second City improv company. It was a fact no one could forget during an interview he gave Wednesday at the National Venture Capital Association Conference in San Francisco.

Costolo, interviewed by Foundry Group’s  Jason Mendelson, had a quick answer for just about every question thrown at him. And while his replies often exceeded the 160 140-character limit of proper Twitter form, they did drive home a clear impression that the Twitter boss has his own take on how to run an insanely fast-growing Internet company.

One point Costolo, a native of Troy, Mich., touched upon repeatedly were the challenges of running a company in the capital of tech startup territory.  Having experienced tech working culture in Chicago and San Francisco, where Twitter is based, he had some negative things to say about the latter. For one, he says, “competition for engineering talent here is incredibly mercenary and challenging.”

“Out in the Midwest, you don’t have to worry about ‘I have to get them better burritos or they’re going to go somewhere else,” he says. “You have to worry about that stuff here.”

Another downside of San Francisco and Silicon Valley, Costolo says, is the constant, snarky, self-referential chattering about who is going to be the next hot startup. “People focus too much on what everyone else is doing,” he says. “You particularly notice it here.”

That said, Costolo did have some positive things to say about the Bay Area, which is, after all, where Twitter has chosen to put its headquarters. In particular, there are a lot of tremendously talented people locally, even if they are demanding about their company-catered snacks.

As for venture capitalists, another group disproportionately represented in Silicon Valley, Costolo was decidedly tongue-in-cheek. Asked what he likes most about VCs, Costolo replied: “They pick up the check at dinner.” Asked what he likes least about VCs, he had a one-word answer: “Dinner.”

On a slightly more serious note, Costolo devoted some time to criticizing the U.S. patent system, which he calls “literally an arms race.” Too much time and money is also devoted to defending frivolous patent lawsuits, which has prompted Twitter to promote the Innovator’s Patent Agreement, which restricts patent use to defensive purposes.

Costolo also confirmed that Twitter has no plans to up its character limit, despite Mendelson’s request for a bump up to 200 characters. “Real constraint emboldens creativity,” he observed, then moved on to sharing some of his favorite Twitter exchanges.

One was a Canadian rapper’s tweet that the first million is the hardest. It prompted energy tycoon T. Boone Pickens to tweet back that “the first billion is even harder.” As for Costolo’s all-time favorite Twitter reply? That came from Mia Farrow, in a response to a tweet from comedian Sarah Silverman suggesting that people try to deal with difficult family holiday gatherings by pretending to be in a Woody Allen movie. “Tried that. Didn’t work,” Farrow replied.

Costolo says he wasn’t the only one of his Second City colleagues to go on to career success. The difference however was that others – including Steve Carell and Saturday Night Live regular Horatio Sands – actually did so in comedy.  Costolo says he’s still in touch occasionally with improv colleagues. For instance, he says, he recently had the chance to meet up again with Carell and brought a copy of an old review from their time together in Chicago.

Carell’s response, according to Costolo, was “I’m really sorry it didn’t work out for you.”