An Interview With Jack Dorsey

There is perhaps no leader in technology more misunderstood than Jack Dorsey, the enigmatic founder and (twice) former CEO of Twitter, now X. Through Covid, and America’s first real era of broad, highly-politicized social media thought policing, he became the face of censorship for large swaths of the country. But from his second appearance before Congress, where he made enemies of both the left and right in one of the more inspiring displays of disrespect for would-be tyrants I’ve ever seen, and in light of his committed, years-long focus on anti-authoritarian technologies, that simple story of free speech villainy never made sense. Jack recently deleted his account on Bluesky, once pitched — by him — as social media’s decentralized solution to censorship, and left the company’s board. I reached out and asked him why, which is where our call began. In a rare, far-reaching interview, what follows is a missing chapter of internet history that sheds light not only on Bluesky, but Twitte

There is perhaps no leader in technology more misunderstood than Jack Dorsey, the enigmatic founder and (twice) former CEO of Twitter, now X. Through Covid, and America’s first real era of broad, highly-politicized social media thought policing, he became the face of censorship for large swaths of the country. But from his second appearance before Congress, where he made enemies of both the left and right in one of the more inspiring displays of disrespect for would-be tyrants I’ve ever seen, and in light of his committed, years-long focus on anti-authoritarian technologies, that simple story