Jack Dorsey defended Twitter while investors wanted to milk it for money. What’s the platform’s future?

Jack Dorsey, the founder and CEO of Twitter, announced in a Tweet early Monday that he is resigning after working at the tech giant for 16 years.

He leaves behind a platform he truly believes in, says WIRED Editor-at-Large Steven Levy.

“It was his invention, a way [to facilitate] intimate communication [and] instant communication with your friends,” he tells KCRW. “Of course, it expanded to a larger cohort than the world itself. But he never lost touch with that sense of intimacy that he hoped Twitter would provide to people. And he [that] practices day in and day out as he uses Twitter.”

Initially, the platform embraced free speech, despite evidence of widespread harassment and misinformation.

“Twitter actually embraced the whole concept that people could say anything. One of its first general counsels said that Twitter was the free speech wing of the free speech world,” he explains. “I called [Dorsey] the Hamlet of Silicon Valley, where he would acknowledge these problems, but not take the severe measures that are required to really contain them.”

Despite criticism from the company’s shareholders, Levy says Dorsey stayed true to his commitment to free speech on the platform.

“He had this lack of artifice. He behaved in a way where he was unafraid. … He was very much himself. And he's an interesting person, an introspective person, and someone who was passionate about his product. So I felt sympathy for someone who defends his product over a bunch of activist investors who basically are interested in just milking the place for profit.”

But Levy points out that Twitter’s management team struggled to produce growth.

“Twitter did fail to reach its original goals of having at least 1 billion users in 2009. I remember doing a story and they were saying to each other in internal papers that came out that they wanted to be the first social network with a billion people. They never even came close. And of course, Facebook got that crown.”

Why the missed target? The platform is popular among people who are interested in news and tech, and resonates less with casual users.

“For a lot of people who aren't technology freaks or news freaks, or people who don't have their group of friends they communicate with on Twitter, they get on the thing and they don't know what to do. They don't know who to follow. They don't know what to say. They're a little nervous about it as well. … They'll leave. This is something that Facebook cracked very early, sometimes by really dicey practices. But Facebook was rigorous on growth and retention in a way that Twitter never was.”

But as Twitter continues under new leadership, Levy says he expects the platform to embrace a different approach to growth. He predicts it will be an uphill battle.

“We have already started to see some of the changes. They have a subscription product now, a premium product, and they're moving away from only collecting revenues from advertising. And I think they’ll be trying to expand growth,” Levy says. “That's a tough problem that I'm not sure that even [the new CEO Parag Agraway] has worked on. I'm not sure that he's going to be able to crack that problem. It's a really tough problem when getting Twitter to a billion people.”