Jack Dorsey’s Complicated Twitter Legacy

As influential as Twitter has been in our society, it could have been an even bigger business if Chief Executive Officer Jack Dorsey had figured out how to capitalize on short video — a format that went on to make TikTok a social media sensation. Bloomberg Opinion senior columnist Tim O’Brien was joined by Kurt Wagner, who covers Twitter Inc. for Bloomberg News, for a wide-ranging discussion on Twitter Spaces about Dorsey’s legacy after he abruptly resigned this week as CEO of the platform. In the transcript below, lightly edited for length and clarity, Opinion technology columnist Tae Kim leads a conversation that includes how Dorsey’s dual role as CEO of both Twitter and Square Inc., and his obsession with cryptocurrency, might have influenced his decision.

Tae Kim: What did you first think when you heard Dorsey was stepping down?"

Tim O’Brien: I felt this was long overdue. If you're the CEO of two companies, you're not really the CEO of any company. I've always wondered about the sense of yourself as a manager and how serious you are about the vision and the employees at both companies if you're claiming to be able to manage two high-profile companies effectively. Jack famously basically invented Twitter when he discovered he could use text messaging as the spine for a robust digital media and communications platform. But I don't think Jack ever had his vision for where he wanted to take it and what he could do to improve the quality of the service and in the lives of users on Twitter. I say this as a passionate Twitter user. [Twitter] breaks down walls among people, but for the most part, it's been the province of journalists, celebrities, politicians and athletes with some interesting subgroups as well. But it hasn't been proven yet that it can grow up and continue to thrive in a competitive world.