Twitter CEO Dick Costolo is a funny guy. Seriously. Prior to entering the technology world, Costolo was a stand-up improv comedian in Chicago. He later worked at Google after the search giant bought his company FeedBurner. Costolo still had his sense of humor by the time he reached Twitter in September of 2009 as chief operating officer. His first tweet: “First full day as Twitter COO tomorrow. Task #1: undermine CEO, consolidate power.” One year later Costolo replaced co-founder Evan Williams as CEO. Ha-ha.
Today, Costolo runs an Internet company worth an estimated $10 billion that has transformed media, entertainment and politics. Every day, millions of people send out 140-character messages about everything from what they had for lunch to the gravest matters of international affairs. The service allows companies, celebrities, and politicians to forge a direct connection with followers, eliminating traditional middlemen and intermediaries. Still, despite Twitter’s success, Costolo has one of the toughest jobs in tech: Turning this wildly disruptive communications platform into a money-making business that justifies its sky-high valuation.