When the bombs hit in Iran, I thought of Jack Dorsey. In 2009, he and I were both part of a contingent of technology people sent by the US State Department to Baghdad, in the wake of another questionable Middle East war. At that time Dorsey was not involved in Twitter’s day-to-day operations, and he was glumly following from afar as his cofounders embarked on a media tour to celebrate the success of the product that sprang from his vision. Our survey of a city ravaged by war—we wore flak jackets and helmets when venturing outside the protected Green Zone—was a distraction from his obvious pain of exile.
Dorsey more than recovered. Not long after our trip, he founded the fintech company Square (now called Block), and in 2015, he reclaimed leadership of Twitter. He ran both companies for several years, until 2021, when he stepped down as Twitter CEO and then sold the company to Elon Musk. Dorsey still leads Block, which made almost $3 billion in profit last quarter, has a $39 billion market cap, and employed 10,000 people—until last week.
That’s when Dorsey hit the news by discharging almost half of his workforce. His explanation was that recent advances in AI tools are forcing Block to remake itself as a slimmer, more nimble entity—and that other companies will follow suit.
The move was classic Dorsey, who ignores many of the conventions of corporate mogulhood. He lives a nomadic existence, rocks a hipster beard, and advocates meditation. He is a life-long proselytizer of open source protocols and decentralization. And he’s quick to embrace any technology that he perceives as the future, be it Bitcoin or AI.
In our conversation, I pushed him on why he thinks corporate bosses must discard conventional management and restructure around a layer of AI, with many fewer employees. Or whether he was simply using AI as an excuse to trim a bloated workforce. And of course I asked him what he now thinks of X.
Steven Levy: You just laid off almost half of your company. There seems to be some question whether it was a correction to your overhiring. Were you AI-washing the layoffs?
Jack Dorsey: The most important thing for me and the company is that we stay well ahead of the technology trends that are impacting us. This comes down to one simple thing. These tools are presenting a future that entirely changes how a company is structured. I don't know what the ultimate outcome is, but I do know it's going to have a dramatic effect. I want to make sure we can be proactive about those moves, instead of reacting. If I allowed it to be drawn out, we’d be in a worse position.
Did you overhire?
I wonder what metric people are using for that. The metric that matters is gross profit per employee. We were exactly in line with or just ahead of all of our peers. We hired at the same rate that they all did during Covid, and we corrected around the same time as well. This was not looking at our cost and revenue per employee and fixing it, because we were already ahead of all of our peers. This was looking deeply at what the tools can do now and our own application of them.
Your employees didn’t seem to be satisfied with that explanation. In the company meeting after the layoff announcement, one of them seemed offended that you were wearing a hat that said LOVE. Is a compassionate layoff an impossible task?