The Comedy Career of Twitter’s Former CEO

Dick Costolo, who’d beenTwitter’s CEO since 2010, last week announced that he’s stepping down from his post. Twitter co-founder Jack Dorsley has been appointed CEO until the board finds a replacement. Twitter’s share reacted positively to the news, surging by 7%.

Costolo had taken over the reins of the social networking site in 2010. He presided over Twitter’s successful IPO, in which shares had jumped almost a 100% after being listed. He is also credited with bringing in large scale product changes at the company, including instant timelines for new users, and doing away with an unfiltered timeline and adding a “While you were away” feature.

dick costolo linkis


However, Twitter has had its share of struggles in the recent past. Its user engagement has failed to keep up with formal rival Facebook, and its advertising platform has found it hard to monetize its 300 million monthly users. Things came to a head earlier this week when Twitter investor Chris Sacca wrote a 8500 word post about what was wrong with the company. Twitter also missed its analysts estimates this quarter, and shares tanked 25%.

Sources say that Costolo stepped down voluntarily. As a result, he will be receiving no severance package.

Costolo, 51,  has had an interesting journey in the tech world. He’s no Mark Zuckerberg or Evan Speigel who found success in his early twenties. In his early twenties, Costolo was a struggling comedian who was barely making ends meet.

 Costolo had enrolled himself as a Computer Science student in the University of Michigan, and was well on the safe career path with a tech bigwig once he graduated. Fate had other plans though. In his senior year, he happened to take an acting class because “there wasn’t too much homework, and it left me with more time to work on my operating systems”. He ended up loving the class so much that he took another acting class in the next semester, and started doing standup comedy in the clubs around Michigan.


twitter ceo Dick Costolo
Source: Business Insider



When he graduated, he had offers from three technology companies to work as a programmer. However, he decided to move to Chicago to get into the improv comedy scene. His ultimate plan was to make it big in the comedy world, and perhaps appear on Saturday Night Live.

He didn’t become an overnight Hollywood sensation though. He’d made a big bet on himself, and it wasn’t paying off. “I had no money, and I was grinding away. We’d rehearse during the day, and perform in little theaters at night for free.” He even did odd jobs to make ends meet, using his CS degree to work as a clerk at a tech store.

After many years of struggle, he eventually gave up on his comedy dreams and worked at Anderson Consulting as a senior manager in the product and technology groups for 8 long years. Then the internet boom hit, and it was finally Costolo’s time to shine. He co-founded Burning Door Networked Media, a web design and development consulting company, which was acquired by Digital Knowledge Assets in October 1996. He then co-founded SpyOnIt, a web page monitoring service, which was sold to 724 Solutions in September 2000.

From there, he went on to co-found the web management feed provider Feedburner, which was bought over by Google in 2007. He joined Twitter in 2009 as COO, and eventually became CEO in 2010.

Cosotlo’s career path is interesting, and unique for a top tier CEO. He took a strange detour from technology to comedy right after college, but eventually ended up where his CS degree would’ve brought him. He has no regrets about his improv stint though. “Make bigger choices, take courageous risks”, he urged graduating students at the University of Michigan while speaking at their commencement about his tryst with comedy.

“You can’t plan a script. The beauty of improv is that you’re experiencing it in the moment. If you try to plan what the next line is supposed to be, you’re just going to be disappointed when the other people who’re on stage with you don’t do what you want them to do. It’s often best to be in the moment.”