“I relate to all of them, in the sense that they’re in the struggle, and the struggle is a real struggle when you’re an entrepreneur and you’re grinding away and you’re [part of] a small team and you’re trying to get to point B and there are all these giant companies around you.” So says Dick Costolo, Twitter’s COO from 2009 to 2010 and CEO from 2010 to 2015, of the characters on the TV show on which he now serves as a special consultant, HBO’s Silicon Valley (the first episode of the third season of which airs on Sunday night), as we sit down at his office in Silicon Valley to discuss his unusual life and career. “It does a great job of capturing that and how hard it is, while making it all very funny.”
(Click above to listen to this episode now or click here to access all of our episodes via iTunes. Past guests include Steven Spielberg, Amy Schumer, Harvey Weinstein, Lady Gaga, Will Smith, Kristen Stewart, Samuel L. Jackson, Brie Larson, J.J. Abrams, Kate Winslet, Ridley Scott, Jane Fonda, Michael Moore, Sarah Silverman and James Corden.)
It turns out the 52-year-old, who was born outside of Detroit, and whose father was a computer scientist long before most people had personal computers, has had his foot in the world of comedy before, back when he was an undergrad at the University of Michigan. “I was studying computer science,” he says, “but at the time the computer science school was in the school of literature, science and the arts — it wasn’t split out into engineering yet — so I had to have all these arts credits to graduate. My senior year I took a couple of acting classes, and I loved those and I started doing stand-up at the student union.” After a few months of warming up the big comedians who performed at Ann Arbor on Thursday nights en route to weekend performances in Detroit, Costolo recalls, “I got the bug and decided, ‘When I graduate, I’m just gonna go to Chicago and try to get into Second City instead of taking any of these programming jobs.”
That’s precisely what he did: “Steve Carell and I were in the same group, sort of coming up through there. Rachel Dratch is a friend from way back. And Matt Walsh, who’s on Veep now — the other show premiering on HBO Sunday night — Matt and I performed a bunch at The Annoyance Theatre in Chicago before he went and did UCB [Upright Citizens Brigade]. So I know a lot of those folks.” While he, too, “totally wanted” comedy to be at the center of his long-term career, and while he “could hold my own improvising at any length” (but “wasn’t really great at developing a particular character”), he decided, after seven years, that he ought to focus his energies elsewhere. “I decided at some point,” he remembers, “‘Hey, don’t eat Ramen noodles anymore. [You’ve] got a computer science degree, go put that to work!'”
Thus began, for Costolo, a string of tech jobs in Detroit. He went to Andersen Consulting and worked in systems integration practice and technology services organization. Then, as the Internet took off in the early 1990s, he started a web design and development shop, which he ultimately sold. From there, he started several tech companies, including Feedburner, which he sold to Google in 2007. Around that time, he reconnected with an old friend, Evan Williams, who asked him to move out to Silicon Valley to help at a new social media company — built around 140-character messages — that was just getting off the ground.
Twitter had launched in 2006, taken off in 2007 at SxSW and exploded in 2009 when Ashton Kutcher and CNN competed to see who would get to one million followers first. But the company had yet to figure out how make money, and Costolo was brought aboard in Sept. 2009 — first as COO for a year, then as CEO for five years — to guide its growth. He recounts, “There were about 50 of us … The architecture of the service wasn’t great and was crashing all the time … We didn’t really have any idea how we were gonna make money. We were just trying to build the team as fast as we could and keep up with the crazy user-growth that we were having at the time, while figuring out how we were gonna [make] money from this thing.”
During Costolo’s tenure as CEO, the company’s name became a household word. Iranians went up in arms when Twitter was blocked during the run-up to their 2009 presidential election. Tweets played an instrumental role in the organization of the Arab Spring that swept through the Middle East from late 2010 through mid 2012. And Charlie Sheen publicly broadcast his meltdown on the platform in 2011. Meanwhile, the company’s staff grew from 50 to 4,000, revenue increased from $0 to $436 million per quarter (thanks mostly to the implementation of an ad platform he commissioned) and valuation shot up from less than $3 billion to more than $23 billion. “It was crazy,” he says.
Last July, Costolo left the company to spend more time with his daughter, who would soon be heading off to college. At the time, he could never have imagined that his next job — albeit a part-time one — would be working on Silicon Valley, an HBO comedy that he “binge-watched” when on flights and came to greatly admire. He says, “They did such a great job — Mike [Judge, the show’s co-creator, EP, writer and director] and Alec Berg [the show’s EP, writer and director] and the writers on the show — capturing some of the absurdities and the tone of voice of the way things are dealt with and the kind of nonsense that entrepreneurs have to go through in doing things like raising money. So I loved that about it.”
After departing from Twitter, Costolo had lunch with Silicon Valley reporter Kara Swisher, who knew of his background in comedy and and suggested he meet with Judge and Berg about Silicon Valley, who were looking for a consultant to help them with season three of the show. They hit it off, he was offered the job and soon he was a regular presence in the show’s writers room on the Sony lot in Culver City. “I would fly down to LAX, Uber over to the Sony lot and get started around 10 a.m.,” he says, “and go all day until 7:30 or 8, Monday and Tuesday of every week until we were done.”
He admired their “rigorous” emphasis on getting right facts and situations related to life in Silicon Valley: “They do a ton of research on the kinds of language these companies use, and the way they talk about their visions, and the way they talk about their culture, and how VCs decide whether to invest in something or not, and the kind of language they use when they do or don’t agree to invest in your company. And when they have an argument with a CEO, where does that take place? Does it take place at the CEO’s office? Would they ask the CEO to go out for dinner?” As a result, he says, “You end up with this show that works for people who don’t know anything about the industry, because you’ve got these universal characters, but the situations they’re in are so acutely tuned to, ‘Oh, yeah, that’s exactly how that would happen,’ that it also works extremely well for the people in Silicon Valley.” (Many tech power-players, such as former Google CEO Eric Schmidt, have even made cameos.)
Will Costolo remain involved with the show into the future? “I don’t have any idea,” he says — but, he volunteers, “I would love to be more involved in the creative side of the media world, just because it was something I used to do, and it’s something I love to do and I had a ball doing Silicon Valley.” In the meantime, though, he has acquired two new day jobs, working at Index Ventures and having started a new company. “So,” he says, “we’ll see what happens.” (Later that night, during a Q&A that I moderated following the show’s season three premiere in Silicon Valley, one of the panelists let slip a fun fact: Costolo will make an onscreen appearance in season three, as well.)