By 2008, Dorsey was out and Williams was CEO. Two years later, Williams himself would leave (though remain on the board) and Costolo—then the company’s chief operating officer, hired from Google—would become CEO. Dorsey also rejoined the board. Now nearly five years later, the company remains incestuous: Of its eight board members, three are former CEOs.
This is all to say: Twitter isn’t in the clear yet, and if investors were looking for a caretaker executive as interim, they didn’t seem to have gotten one.
So what did Costolo accomplish during his five years? The headline is: He took Twitter public, a messy process that created a lot of wealth for bankers and some of its early investors. To his credit, he also continued its advocacy for freedom of speech. Twitter, alone among social networks, does not take down content when ordered to by a national government but merely blocks it from being seen in that country. It also publishes some of the best, most exhaustive data about the government requests—censorship, copyright, or user data-related—it receives.
But to recount the last five years of Twitter’s history is to create an annal of missed opportunities. Twitter seemed, almost systematically, to frustrate those who saw themselves as the company’s allies—or, at least, its most loyal users. After encouraging developers to build applications around the service for many years, it altered who could access its data, creating an atmosphere of instability for any third-parties who thought about investing time improving its service. For years, too, it barely addressed the rampant abuse that people—and women in particular—face on the service. This sowed fear and frustration for many of its power users, who could face threats or cat-calls sometimes just for tweeting about movies or video games. (It does not help that seven of Twitter’s eight board members are men.)
The company also failed to capitalize on the boom in messaging services. Despite serving as the web-facing identity for many Internet power users, it never appeared to prioritize its buggy messaging service, which would sometimes tweet text that was supposed to be a private correspondence. It shipped small improvements—like letting users send photos to each other—but never broke out its DM service into a separate app, as Facebook has done. Meanwhile, WhatsApp and Snapchat’s user bases swelled.
The more irredeemable loss might be in how the service is perceived. In 2010, Twitter was ascendant, an insurgent peer to Facebook—if anything, it was the kinder, friendlier, more open public square to Zuckerberg’s castle. Its format was hailed as revolutionary, and it was credited with fomenting revolutions. Now Twitter usernames and hashtags are ubiquitous, appearing on the sides of billboards, before every major sports broadcast, in street art, on church pamphlets—even on Facebook. The @-symbol before a username, first seen on Twitter, is the global standard for setting off a username in text.