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?
I don’t think it’s an impossible task. I wanted to approach the whole situation with love. We had an all-hands where they could show me all the emotion and give me the feedback. I believe our settlement to be generous compared with the rest of the market. I wanted to do it from a position of strength, so that we’re not offering a less interesting severance package for people when our backs are against the wall. For all the negative messages that we may have gotten on that stream, we’ve gotten a lot of gratitude as well. It’s not just about our company. It points to a larger thing that might happen in the future for many other companies.
What triggered you to take such a drastic action?
Something really shifted in December in the sophistication of [AI] tools. Anthropic’s Opus 4.6 and OpenAI’s Codex 5.3 went from being really good at greenfield products to being really good at larger and larger code bases. It presented an option to dramatically change how any company is structured, and certainly ours. We have to rethink how companies run, how they’re structured, how they’re built. It has to be closer to building the company as an intelligence. Yeah, certainly with any company you could say that there’s bloat—but that’s a function of inheriting a management structure and a hierarchy all the way back from the 1900s.
You built Block from scratch, Jack—it’s your company.
Absolutely. We did what other companies did because that was the right way to do things. But given the new technologies and tools, we have to recalibrate. Every organization has to do something similar.
When Elon took over Twitter, he also did massive layoffs that seemed to encourage a lot of CEOs to be bolder in reducing the workforce. Did that experience influence you?
No, it’s a very different situation. Twitter was a public company becoming a private company, loaded up with a massive amount of debt. Elon could dramatically change the business model, which it needed. I’m grateful for all that. I think Twitter should have been private for quite some time.
When you fire half of your company, you may lose key people that support specific products. Are you trusting your workforce to self-correct and in some kind of emergent fashion figure out who does what?
Absolutely. When you’re faced with a different reality, you think differently. I believe with all my heart that the shift is profound in ways that I don’t think anyone can really understand or realize the ultimate manifestation. If I were to build a company today I would just do it in a completely different way. I would have no management hierarchy whatsoever. The company itself would be focused on all the artifacts of the work that we’re creating, with an intelligence layer on top that everyone in the company could have a conversation with and query and build intent into. That’s just not how companies work today. They’re very structured and very concrete around management hierarchy. That’s getting in the way of everything that we need to do, and I think it’s existential. I don’t want to be a company that dies from irrelevance.
So Block will have a layer of intelligence as its core and organizing principle?
I want the company itself to feel like a mini AGI. We’re moving to a world where our customers will have the ability to create their own products, experiences, and customizations. If you put an intelligence layer on top of the company, you can actually query it, have a conversation with it, and very soon build some of those things for customers, and then scale them much quicker than ever before.
So your customers will essentially vibe-code Block to make personalized products?
Yeah, that’s a path forward for almost every product. I don’t think people want more products or more features. They want peace of mind, and they want to be able to build what they want for their needs specifically.
It seems to me that you’re supporting the claims by Dario Amodei and others that half of white-collar work will be gone.
No one knows what the future holds, and certainly not me. I do believe that people will shift into other types of roles and work, and that gives me optimism. But I can more or less guarantee the role of a company is going to be markedly different.
Let’s talk about where Block goes. You made a big push into crypto and Bitcoin, where progress is stalled. How are you feeling about your Bitcoin products?
We didn’t make a push into crypto. We made a push into Bitcoin because I believe the internet needs an open protocol for money transmission, and Bitcoin represents that protocol the best to me. It’s not controlled by any one company. I don’t like that we’re going to support stablecoins but our customers want to use them. I don’t think it’s wise to go from one gatekeeper to another.
For your whole career you have argued for decentralization. But the digital world keeps getting more centralized. Does that disappoint you?
I think it ebbs and flows, OpenClaw is proof of that. That project shows that people want agency, and agency derives from decentralization.
Are you happy with the job that Elon is doing with Twitter, or as he calls it, X?
I’m happy that it’s a private company. I’m happy that it’s changed its business model. I don’t think it’s always leading to the most positive outcomes. Some of the algorithmic choices can be improved drastically. And I’m most upset that it fragmented the conversation across ideological lines, versus one protocol being able to host everything. Maybe that desire was just way too idealistic.
At one point Elon tweeted that he found a bunch of “Stay Woke” T-shirts in a closet and made fun of them with a crying emoji. I thought of you because I know that those were from a Black employee group at Twitter, and you wore it proudly. You were very passionate about standing up for civil rights at Ferguson, near where you grew up. And the guy in charge of your company was mocking that impulse. How did you feel about that?
Those T-shirts grew out of our community. I don’t think it’s wise to mock the people that use your platform and love it. That leads to more fragmentation. But to be honest, I didn’t pay a lot of attention to what was going on in the company at the time. Parts of it were super frustrating, and parts weren’t.
How are you viewing politics these days?
Super confusing. Everything feels like a mess. The only thing we can do is bring more transparency to how things work, and give access and agency to more and more people. I don’t believe one system is going to fix everything, and I don’t believe one party is going to fix everything. I’ve never been on one side or the other.
A lot of your fellow CEOs clearly believe they have to cater to Donald Trump. Are you under pressure to develop a good relationship with him?
No. I’m doing what I think is best for the company. Those leaders are making their own decisions for their companies. I think there needs to be a separation of state and private companies, especially for technologies that are so critical. Obviously, governments are going to use these technologies. We have to build something a lot more neutral, but also recognize that we’re American companies, and we’re in this legal system.
How are you feeling about journalism these days?
Also challenging. It goes back to judgment and taste. We’re overloaded with information, and a lot of information that isn’t credible. I’ve always believed in citizen journalism and in Twitter as a news source in real time, but I still think we need people who can make cohesive sense of it and disclose their bias in doing so. It requires great storytellers to make sense of the world, and that’s being diminished in some ways, but I think there are still greats out there.
About two years ago you made some posts critical of WIRED.
Only because I grew up with WIRED. I would go to Barnes & Noble and, like, it would be the first thing I’d search for and read. And I would sit there and read the whole thing. I’m sorry I didn’t buy it, but at the time I couldn’t afford it. It was just so focused on this optimistic technology future and hacking culture. It was on the bleeding edge in terms of political ramifications of technology and cypherpunks and the internet. It feels like it’s taken such a negative turn, and I don’t see the optimism there.
Maybe the circumstances that we cover have changed. A lot of people feel let down by what now looks like over-optimism on technology’s impact. Take social media—everyone was thrilled with Twitter in its early days, as well as Facebook and other services. It turned out that there was a lot of toxicity. Don’t you feel that the promise of social media hasn’t been met?
I think it can be very toxic. But I also learned a lot from it. The biggest thing I would change is to give more sovereignty to people. I do think that Twitter having to be a company was its ultimate downfall. It should have stayed at the protocol level. We should have an open protocol for social media. No company should own it, and we should all be able to build on top of it. That would address a bunch of the problems that have come up.
You were the original force behind Bluesky. Are you happy with it now?
No, because it’s gone to the other ideology. I left the board. It started taking investment from VCs and building like a normal company. I understand why, but it’s not what I signed up for, and it’s not why we created the project. We created it to be an open protocol for everyone, not to be something that’s against Twitter or against other social media. The largest issue right now is the algorithmic filter bubble.
Do you think that AI is going to render obsolete our current system of funding and building companies?
It challenges the norm completely. Every company that’s not building itself as intelligence is going to face something existential, and it’s going to happen over the next year or two. That’s what weighs on me every single day—this thing could just go away completely. So, yes, like, it certainly changes funding, it changes social media, changes learning. There’s no technology that’s compounded this quickly.
You seem to live a different lifestyle than other CEOs. It’s not really clear where you live or in what country.
We’re a fully remote company, so I just work wherever feels right for the moment, not necessarily overseas. I’m in the US a lot, wherever I feel most creative. And we meet when we need to meet, and at that time, in-person is really great.
I hear meditation is a big part of your day.
It’s one hour of my day, but we have 24 hours in the day. I do think it’s helped me, and it helps everyone that has tried it. Just being able to take on a lot of stress and not be reactive.
How are you viewing the big AI companies these days?
It’s incredible how quickly they’re moving. My concern is that the switching costs between the models is fairly low, if not zero. You’re seeing that play out with [the Pentagon’s switch from] Anthropic. I don’t think you’re going to lose much in terms of capability by going between one or the other, and I think that’s very, very telling.
Are you supporting Anthropic on the red lines it’s drawn over the use of its products?
I appreciate the principle and their standing behind it. I think that’s right.
As we went to war with Iran, I remembered our trip to Baghdad. Did you flash back to that, too?
I’ve thought about that a few times. It’s a little crazy that we had that experience together. It just feels like we keep repeating these things over and over again.
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