Jack Dorsey: Every Company Can Now Be a Mini-AGI

Intro

Jack Dorsey: Since last year, I’ve just had this existential dread and also hope and optimism, in the same hour, in the same thought process of like, what is even a company going forward? What are these structures going forward? And this is the only durable structure that I could actually imagine lasting for quite some time. And it was coming from a place of, like, wow, is our company just going to be completely irrelevant in the next coming years?

Brian Halligan: All right, everybody. We had Jack Dorsey on the pod today, founder of Twitter and founder of Block. He’s the only founder to have two of his companies end up on the S&P 500. Just learned that today. I thought it’s pretty cool. Also, Roelof Botha, who’s a Sequoia partner and is on Jack’s board at Block. The conversation was super interesting to me. He recently put an article out that you may have seen called “From Hierarchy to Intelligence,” and it’s a manifesto on how to rethink, basically rethink from first principles how an organization works. How do you completely eliminate hierarchy, and how do you put AI right in the center and transform how your company works? And I let him go on that, and he was very thoughtful and he spoke a lot about it. Block is really changing the way it’s organized. Before we started he said, “I’d love to get some feedback from you and from other people on this.” So if you’ve got comments on it, let ʻer rip. He wants some feedback on it. He’s in the early innings of a big transformation over there.

That was about half of it. The second half of it, I just asked him for CEO advice. I work with lots of CEOs, as you folks know, like how do you build an amazing board? He’s certainly got some scars around board building. How do you build your second act? Like the Cash App versus the original business of Square. Is it a good idea to be a CEO of two different companies at the same time? Being brave and not giving a flock versus going with the flow, and when do you really dig in and when do you kind of go with the flow? And he had some really interesting thoughts on the job of a modern CEO. So tune in, I’ll be back at the end and give you some further thoughts. But I thought Jack did a really nice job. And Roelof, too. Let’s get into it.

Main Converstion

Brian Halligan: Jack, I read your piece, I think it’s fantastic—“From Hierarchy to Intelligence.” Before we get into the meat of what it is, can you describe what you think is wrong with the way normal companies’ hierarchies work, companies like HubSpot, companies like Block? Like, what kind of led you to this?

Jack Dorsey: I don’t know if there’s one thing that’s ultimately wrong. It’s just recognizing what do we see in the pattern? What is the function of the hierarchy? And what we wanted to explore is just where does it actually come from and why does it exist in the first place? And if you look at it from first principles, it’s all about information flow to a broad base of people. So being able to communicate over a breadth of people and have that be manageable at a human scale. So we’ve gotten into structures that we’ve borrowed and iterated on a little bit over 2,000 years.

Brian Halligan: Yeah.

Jack Dorsey: And now we’re facing, I think, a completely foundational moment in being able to question every element of how we work. And the one that I think is questioned the least is probably the hierarchy, and probably about how we manage communication flow around the company. So if we’re in a world where we are today, where Block, for instance, is completely remote, we’re remote first, every single thing that we do creates some sort of artifact, whether it be a Slack message, an email, pull request, code, Google document, a meeting that we record—all these things have these artifacts of information about how the company is working, is building, is failing, is making mistakes, all these things. And traditionally, we’ve been relying upon humans in a management structure, in a hierarchy, to go up and down a chain to relay that information. Instead, we can take all of those artifacts and put an intelligence on top of it, build a model around it, and actually have a conversation with the company about how the company is doing. And it’s not just me as CEO that can do that, but anyone in the company could have that same sort of access to information and same understanding of what the company can do.

So you get to a point where you can build these world models for companies, like, treat the company as a mini AGI, for instance, an artificial general intelligence, because it really is. I mean, if you look at a company, it is an intelligence. But it hasn’t been structured in the way that’s the most efficient or the least lossy in terms of information flow and what people can actually do within the company.

So the technology is good enough today that we can actually model the company. We can have everyone in the company put in intent, which would be strategy or these artifacts, and we can also have everyone in the company query it as well. And it just really opens the door for what’s possible.

Like, Roelof and I have a board meeting every quarter where we construct a bunch of board docs, slides, presentations. We get only so much time for them to have questions, but imagine if every single board member can just query the company and have a conversation with the company’s intelligence in real time. And we can make that meeting time that we have every quarter really focused on more of the creative or bigger existential decisions and issues than the day-to-day. The same can be said for our earnings call and analysts, like, giving them fully Reg FD-possible information that is on their timeline with their questioning. But you can scale this to any position or any role in the company, which is pretty phenomenal. And we’ve just never had that ability before, and now we do. And I think the architecture and the structure of the company is ultimately going to determine its velocity and how well its road map for customers is correct.

Brian Halligan: And just kind of drilling down on it, can you describe sort of what the organization looked like before? And granted, you’re very early in this, but what’s it look like now? Which roles have been eliminated, what are the new roles? Just kind of drill down a little bit into what Block looks like today and kind of where it’s going.

Jack Dorsey: Yeah, we are early in it. I mean, just from one measurement of how far along we are would be the depth from me to any other individual in the company. And I would say our max depth right now is probably five.

Brian Halligan: Okay.

Jack Dorsey: Folks between me and anyone in the company. I would want to get that down to two to three this year. And in the most ideal case, you know, there is no layer. Everyone in the company reports to me, and that would be all 6,000 of the company. And that feels somewhat ridiculous when you consider the old structure, but when you consider that the majority of our work is going through this intelligence layer, it’s a lot more manageable. And that goes into the roles going forward. We want to normalize down to just three roles.

The first is an IC, which is a builder or an operator. This is a salesperson, it’s an engineer, it’s a designer, product person, whatever it is. They’re actually working with the tools to build or to operate the company. They’re augmented because they have access to agents, so one person can potentially do the work or explore the breadth that it would take a team or 10 people to do in the past. So that’s number one. And I think there’s a durable human skill that lasts there, which is judgment and taste and creativity. So that’s probably the largest part of the population is the builders and the operators, the ICs.

The second role is the DRI, and that’s someone who can own the customer outcomes. They’re putting a strategy together. They’re understanding what road map allows us to solve customer needs and problems. And they’re assembling a team of these ICs to get something done. But the durable human skill there is ownership and accountability. They’re really owning the outcomes and whether something is failing or not.

And then the last role would be what we consider managers today, which we’re calling a player-coach. This is someone who is building the capability and the capacity of other humans and their craft. But instead of telling them how to do it, they’re showing them how to do it by doing the work.

So these are people who might be ICs or they might be DRIs, but they’re also really good at giving a coaching skill to help the people around them get better and better and master their craft. And today that’s a management structure where ICs and even DRIs report to a player-coach. But I think in the future it’s an assignment. It’s not a reporting structure, but I’m assigned to ICs or I’m assigned to DRIs to help them master their craft. And obviously the durable human skill there is building human capacity and coaching.

And there’s a lot of empathy there and all the soft skills that we recognize great managers are known for, but not making it a requirement that they have to be strategic, necessarily. They have to build because they need to show off the skill and teach in that way, but they don’t necessarily need to be a DRI.

Now in very rare cases, one person can take on all three of those roles. I think I can take on all three of those roles. My leadership team is expected to take on all three of those roles. They’re expected to build as an IC or operate the company. They’re expected to be strategic and actually think about road maps and customer outcomes. And they’re expected to coach and help raise the skill level around them with the people that they work with or with their direct team.

Brian Halligan: Just a little kind of before and after—and you’re mid on this—let’s pretend like it’s working great, and it’s two years from now and it’s extremely flat. Like, what is the role of the CEO before and after? Most of the listeners, by the way, are CEOs. What does planning look like before and after? What happens to all those people who are directors and managers or the kind of glue people? Like, what are the before and afters in your mind?

Jack Dorsey: I think my job as CEO in the past I’ve thought about in three ways. Number one is to ensure that we have the right principles and the right team dynamic, and that’s like hiring and firing, and setting values and setting the culture and setting the tone. The second is to ensure that decisions are being made in context of our customers and industry trends and competition. And the third would be to raise the bar on our execution, like, to constantly increase our capability and to push ourselves to doing things that are uncomfortable so that we’re growing all the time. So that’s how I thought about my job up until this point.

I think in the future, you have those elements certainly, but I think it’s more about the architecture of how the company as an intelligence works. And if we’re building the company as an intelligence, our job as humans and my job as CEO is to constantly align it to where we think the right outcome is. And I see visually the company—the intelligence, the world model for the company—in the center, and then on the edge are the humans who are just constantly aligning this towards customer outcomes.

But even that changes, I believe, because I think a company’s ultimate limiting factor is its own road map. And I think what these technologies point to are that our customers are going to have the expectation that they can ask for a feature that doesn’t exist on our road map and that it just is served to them. And that’s where you really get into the layers of, like, okay, so what do we actually build? We build up capabilities which are effectively our tools. Like, we can issue cards, card acceptance, peer-to-peer lending—all these things we do as a financial technology company. We have these interfaces like Square, which has a register and a dashboard. We have Cash App, we have Tidal, we have Bitkey, we have Proto. These are interfaces. These actually touch the real world, touch humans, and we can deliver our capabilities in these interfaces. Today they’re built with these very specific navigations that are our road map and our understanding of what our customers want.

When you move to the third layer, you have proactive intelligence. We have all this understanding of our customers. We’re moving money—money is the most honest signal in the world. You can lie about literally everything, but when a transaction occurs, that’s something that really tells the truth about your life or your business’s life. And based on that, we can actually prompt our customers instead of waiting for them to prompt us or having the right question to ask. So we can do the very simple but very valuable thing of, like, how do we protect our customers’ cash flow? We have people using us as a bank account. How do we make sure that they can pay the rent and they can pay their Spotify bill and they can pay their kids’ allowance? And this is all sequenced in a way that allows them to never go to zero, never go negative, and have some cushion that allows them to even think about getting to saving or building wealth. And that’s just peace of mind. I think that’s the most critical aspect here.

So if we’re enabling a customer, if we’re able to prompt a customer and also they can ask as a business, “Hey, I have this inventory thing that I’ve been using, but it’s missing this feature—can I have this feature?” We should just be able to build that and compose it in real time based on our capabilities. If we can’t, and it points to a deficiency in capabilities or a gap, that’s our road map.

Brian Halligan: Yeah.

Jack Dorsey: So our customers, just by using and talking with our systems, are telling us what our road map should be and then it’s up to us to give the judgment. And then the final layer is the world model. It’s the customer world model. It’s the company world model, our deep understanding of ourselves and also our customers. But I think if I had to say one thing that myself or anyone in the company has to do, I guess it’s this overused phrase of “judgment,” but it is judgment against what we intend to build in the world. And is it aligned with that judgment? Is it aligned with the values? Is it aligned with the taste that we have? And is it unique or is it not? And I guess for my part, I’m the extra checkpoint on is the alignment circle of humans, the edge of humans, actually working correctly?

Brian Halligan: And I see how this works exceptionally well for Block. You have a lot of signal. How does this work for, I don’t know, Sierra, Workday, somebody who doesn’t have the quality signal, the frequency of signal? Does it apply or does it work as well?

Jack Dorsey: I think it probably does. I think it goes down to, like, are you building a business that understands something of human nature deeply and it gets deeper every single time? And that’s a real tangible signal that just doesn’t go away. And if you are, then I think you can build your company as an intelligence. If you’re not, then it’s probably an add-on to something else. And I think most of the industry is thinking about AI as, like, a copilot, as something that is augmented onto rather than, like, how do you just rebuild your whole company with this as the core? And if it doesn’t make sense for your business to do that, and you end up being or looking very similar or rhyming too closely with the frontier labs, then I think it’s going to be very, very challenging to differentiate and survive.

And that’s kind of what’s been leading me to all this is, like, since January of 2024—which is when these tools really came to bear, like Goose, which is an agent coding harness, was one month before Claude Code in January of 2024. And Claude Code came out that following month and was really put out of beta in May of that year. And that whole year I just spent every single day for three hours every morning just pushing myself, like, can I get it to do something that I didn’t think it was capable of, or I didn’t think I was capable of? And every single day it worked. Like, every single day I was surprised. And I’m sorry, it wasn’t 2024 it was 2025. It’s only been a year of those tools. Like, one year. The compounding nature of this is pretty incredible.

So being able to see that, understand it, and then shift your company to be ahead of it, I think is absolutely critical right now. And I don’t think people are feeling it enough. They’re just living in this abstraction. They’re like, “Oh yeah, these tools will make everyone in our company 10x more productive.” I don’t think this is a productivity thing. I think it’s a structural thing that needs to shift.

Brian Halligan: I think you’re right. I think people are thinking of it as copilots and individual productivity versus—your idea is complete business transformation. And I think it’s super interesting and compelling.

Roelof Botha: Can I add one thought I’ve had as I’ve listened to this so far? One of my favorite pieces of writing ever is Adam Smith’s Wealth of Nations. And this idea that if you have the right signals, you can rely on the self-interested behavior of many small participants in the system to actually lead to optimal outcomes, but you just need to have the right framework and the right system. I think the way that many companies work today is a little bit more command and control.

Brian Halligan: Very much.

Roelof Botha: And you have hierarchies, and you have political actions and people jockeying for position. And it’s not always clear what is actually true. And I think part of what we’re envisioning here is you have a system that’s just ground truth. And you do away with all the layers. You get back to the kind of productivity that founders often long for. They long for the days when there were 100 people and not 500 people because they were so much more productive. Why? Because you had lots of transparency, limited hierarchy.

And so I think the possibility here, as Jack was saying, is instead of just focusing on individual productivity, you reimagine how we work together as humans. And you can do it with a far smaller number of people that are far more productive, yes, but there’s a different way of working together where you get the right signals, and it’s much more similar to a capitalist system where the signals tell you what to build. It’s not somebody who pounds the table harder who gets their product approved, which is listen, more customers want this than that. That’s how we’re going to decide what to build next. So for me, there’s something quite magical in that realization.

Brian Halligan: Yeah. About four years into building HubSpot, I eliminated org charts, no titles. And everyone lost their mind. They didn’t like the idea. And we ran that for about nine months, and I got worn down and I brought it back. The thing we didn’t have was an intelligent system that had all those signals that could help us make decisions. So it’s exciting to see this here. I have a theory I want to run by you, Roelof. Like, I sort of think of it as like there’s manager mode. It’s a pyramid. The VPs make most of the decisions. And there’s founder mode, kind of flat. The founder makes a lot of decisions. And then there’s—I’m just going to call it “Dorsey mode.” It’s a circle and the AI makes most of the decisions. Do you buy that?

Roelof Botha: Oh, I don’t think the AI makes most of the decisions. I think—and Jack should correct me here—I think the AI helps with communicating the alignment, and the management team or the inner core helps set the framework. What is the objective function? Are we optimizing for growth rate, gross profit per employee, net promoter score? Probably some combination of those variables. And the humans at the edges perform an incredibly valuable function of correcting and informing and sort of steering that. And I think one of the phrases that Jack has, which I absolutely love and I’ve stolen so many times, is companies have multiple founding moments.

Brian Halligan: Yeah.

Roelof Botha: There are so many smart people in your company that have clever ideas that every day inflect the product, introduce something new. And so this idea that there’s just one person who is the brilliant person who comes up with everything, I don’t believe in hero worship or the converse of that where you sort of scapegoat people. I think it’s harnessing the best of your team to really advance the company. So I subscribe to the circle idea.

Jack Dorsey: Yeah, I also don’t think the AI is making the majority of the decisions. I think it’s facilitating a more context-rich decision. I think ultimately, in the most ideal case, our customers are actually making the majority of the decisions, because they’re just based on their queries and what they’re trying to do with the system, which delineates where our road map should go. And then it’s up to our judgment as to whether that’s consistent with what we want to be and what we think is most strategic or not.

But we just weren’t able to get to that level of data fidelity before, because we had to infer it. We had to do customer research, we had to do interviews, we had to look at our customer support, product feedback on Twitter, all these other things. But when your interface is a conversation with your customer instead of this visual navigation, you suddenly get this amazing fidelity of what do our customers actually care about? What do they actually want? And it’s up to us then to decide if that’s consistent with what we want to be as a company, or if they should be going elsewhere to do that.

And I think all these things are going to blur. I mean, that’s the craziest thing is like, again, since last year, I’ve just had this existential dread and also hope and optimism, in the same hour, in the same thought process of, like, what is even a company going forward? What are these structures going forward? And this is the only durable structure that I could actually imagine lasting for quite some time.

Brian Halligan: Yeah.

Jack Dorsey: And it was coming from a place of, like, wow, is our company just going to be completely irrelevant in the next coming years—or even sooner? Like, what do we actually differentiate on? What do we have a moat around? And what do we need to be to defend and also to grow that? And all that follows from customer expectation. Like, the most amazing thing about OpenClaw to me was that people wanted to take this thing and contain it into a Mac Mini, and make it very tangibly theirs and have all this agency around what they did with it. And we’re seeing Square sellers do stuff with it like that, interface with the Square APIs. And we’re seeing Cash App customers.

And these are not tech people. These are just people. “I want a bot to help me manage my life.” That agency, independent of your thoughts on how good of a system OpenClaw is right now—it’ll get better and better—but the intent behind that is agency. “I want to tangibly control this intelligence and for it to better me.” And what it makes possible for me is incredible. And that expectation floor has just risen dramatically.

And that leads me again to, like, yeah, our limiting factor as a company is our road map. Like, we need to remove that from the equation. We need to ensure that our customers are truly building alongside us, and that they are seeing us as a series of capabilities that makes their desires fast and easy and valuable. So it really goes back to the capability set that we have, and then the intuition of the interface that we have, and then how intelligent our world models can be to be helpful and to compose UI in real time.

Brian Halligan: I spent this morning at a company called Rogo here in New York City. They read your article. Let’s say you’re advising the CEO of a 100-person company. They’ve already got their hierarchy. What should they do? Should they start with their systems? Should they start with data? Should they start with the org? Like, how should people go about running the Dorsey playbook?

Jack Dorsey: I don’t know about this “Dorsey playbook” thing.

Roelof Botha: But we don’t have it all figured out. I think there’s an important dose of humility that we have, that we’re endeavoring on this path. We believe it’s right, but we know there’s a lot to figure out.

Jack Dorsey: Yeah, it’s more like, at 100 people, or even just starting today, if you were to build your company as an AGI, as an intelligence, what would it look like? And what would you need to really differentiate? Like, if I were starting a company today, I would be so excited about how quickly I could build things and how quickly I could prototype and get things out to customers. I would be in this valley of dread about distribution and attention, because there is so much noise out there and it’s so hard to get to the actual signal of who’s building something interesting that will actually fundamentally change something and will be around for more than a year.

I think distribution really becomes a differentiator. And I think there’s some event horizon where the way we think about distribution today closes off. There are apps, for instance, and websites and traditional retail—there are a number of things that will change. And if you don’t have the distribution today, it’s going to be very hard to fight for that. But there’ll be new areas of distribution that are probably more important. And I don’t know what those look like.

But I would say, like, I would assume that a company of 100 probably is no more than two to three layers deep, hopefully. And now would be the time to just really question, do I need a hierarchy? Like, Brian, a year into Square, I also removed titles, we normalized everyone to lead. We did it because we were talking with all these banks all the time, and you would have these EVPs and VPs and they were looking for the same on the business card and there’s this whole business card culture. So we ripped up all the business cards, we normalized down to a title of, like, you’re a lead of what, and the longer that is behind lead is probably the farther down you are in the organization. And we’ve kept it. You know, we don’t have titles. We have “What do you lead?” Going back to the DRI thing, what are you ultimately responsible for? And I think it’s helped us a lot.

But this is another step. Like, if you’re starting today or you’re 100 today, what is actually fundamental to solving your customer’s problems? And where is the hierarchy getting in the way of that?

And look at all the tools you’re using. Like, look at all the information you’re generating just by doing your work. Just putting that into an intelligence and being able to query it will give you an understanding of the company that is two to three times more than you had before ever. Because you’re relying upon people telling you things. And that doesn’t always happen for various reasons that Roelof spoke to, in terms of agenda or politics or emotions or empathy, all these things. Imagine if your company was entirely legible, like entirely legible, every aspect of it. And we’re not far off from that from a data perspective. It’s putting the intelligence on top of it, and making it useful and then making it proactive. That’s the hardest bet is, like, we can determine causal, getting to predictability for these world models around the company and customer is still right now very much a research bet. But it’s one that’s imminently solvable.

Brian Halligan: Can you guys just take me behind the scenes? Like, Jack, this was a really bold move. You laid off 40 percent of your employees. Just for CEOs listening, what was that debate inside? Like, how big should it be? How bold should it be? You know, Ruth Porat’s got this good line—if you’re gonna eat a shit sandwich, don’t nibble. And you seem like you took a big bite. What was that debate behind the scenes? And then Roelof, like, how did he pitch it to you guys and what was the board’s reaction? Just behind the scenes on that.

Jack Dorsey: Yeah, so it was something—December of last year is when the models really got a noticeable upgrade from being able to be really good at building prototypes and greenfield efforts to understanding large code bases and legacy code bases like our own. Hallucination wasn’t much of a topic in terms of the coding ability, and the tool harnesses became suddenly very mature, just in that month.

And everyone went home for the holidays, and everyone played with these tools and they were surprised at how capable they were and what they could do with them. And we came back, and the conversation was just going around the table, would you build the company this way if you had these tools today? Like, what would the company look like? And everyone around the table and my team just said, it would not look like this. It would not be this size. It would not be structured this way.

And we’ve been making changes on the edge, like going from a GM structure to a functional structure to reduce—like, putting a cap on our layers to four—me plus four—and all these small things. But if we were to really reboot and rebuild the company, would we end up where we look today? And the answer was uniformly no.

And then we just did this exercise of, like, okay, so what is the minimal number of people that we would need to keep the service up 100 percent? And then next, what is the minimal number of people that we would need to be fully in compliance with our regulators? We’re a highly regulated business, so that one’s extremely important to us. And legal, obviously. And then third, what is the minimal set of folks that we need in order to grow, to fulfill our commitments we’ve made to the Street, but also rebuild the company as an intelligence? And that’s roughly the number that we got to. And we built in some buffer in case we made mistakes—which we did. Hard not to, especially operating the way we have. I think going forward it will be much easier, because more of the company will be legible and all of our actions will be a lot more legible. So I’d have a lot more confidence going forward than not.

But it was that, and that was a span of expiration to execution in under three weeks. And I think generally I wanted to make sure that we—if we knew that this was what our company was going to be in the future, I didn’t want to have to do it with our backs against the wall. We’re a public company, and there’s various challenges there. And other companies will probably get to this realization at some point. I don’t want to react to that. I want to be ahead of it, because then we can do it with a lot more integrity. We can do it with a lot more generosity for the people that we’re asking to leave, and even for the people that we’re asking to stay. And we’re not just reacting into something mediocre. We’re acting towards excellence. And that’s just the tone that we wanted to set.

So every day it was just like constantly checking, like, are we doing the right thing? Is this the right set of folks? What are we not thinking about? What are we not talking about? And we kept the group very, very tight, and had a conversation with the board, which in my perspective was very open to it. And actually more than open, more like, “Yes, we agree. We should do this.” But I’ll let Roelof speak to that.

Roelof Botha: It was a very quick process.

Brian Halligan: Okay.

Roelof Botha: I think part of what helps is that Jack had written us a very detailed note laying out the logic. It’s principled. It’s not—as Jack was saying, it’s not reactionary. It’s very well laid out, very logical. It was clear that the company and the management team was interested in a conversation about how to make this work, as opposed to being dogmatic and saying “We have it all figured out.” So even in the course of those three weeks, elements of this evolved, and it evolved in light of feedback from management team members and board members. Some of where we started in the first of those three weeks is different from where we ultimately landed by the time the announcement took place.

And also I think it’s just an example of where we’ve built enormous trust between the board and the management team. We’ve been through a lot as a team, and so we have a lot of shorthand to be able to make crucial decisions like this. We gathered several times in quick succession to make sure we drilled in on the key issues, and the board was fully supportive.

Brian Halligan: You two—Roelof, you’ve been on a lot of boards. Jack, you’ve had your ups and downs with different boards. Any advice for these CEOs listening? Should they start bringing in investors? At a hundred employees, should they start bringing in independents? Like, how do you build an amazing board that really serves the company well, the employees well, the investors well, the customers well? What’s your advice on that?

Jack Dorsey: I mean, early on I always told myself and my team that your first board is your investors, right? And I would treat that relationship as a hire you can never fire. And in fact, they can fire you. And I’ve been on the other side of that. So it really puts pressure on finding the right person that you’d actually want to work with at the company, knowing that you could never fire them. And again, they can fire you. And for me, I think a lot of young founders kind of go for the brand names, especially around VCs, but I always wanted to go for the person. And that’s why Roelof, we were optimizing for him to be on our board and be an investor, but it was the fact that he would uplevel our conversation, uplevel our execution more than anything else and challenge us along the way.

So even as you think about adding independent board members, like, the core function of a board is to ensure that the company has the right CEO. Like, that’s their one job. They have all these committee responsibilities, but the ultimate fiduciary duty is, like, do we have the right CEO going forward? And I think you have to build a board that has different perspectives on that and that is open to wild ideas, the things that are going to just seem crazy in the moment—which, like, this one might be. But it can be rationalized if we talk through it and we really document it and paint a picture of where this could go and what the opportunity cost is if we don’t do something. Because if we didn’t do something like this, I just imagine every year it’s a 10 percent RIF or 20 percent RIF or whatever it is, and that is just the most demoralizing, crappy, non-creative building of a company ever. And it’s all with your backs against the wall, and it just feels like losing constantly. And I had a conversation with the board—I don’t want that. I don’t want to be at a company like that. It doesn’t make sense. It’s soul-crushing, and it’s just not inspiring and I don’t feel good about it. So here’s what I do feel good about, and let’s go, let’s challenge it.

Brian Halligan: Roelof, you’re on a lot of boards, you’re on some really good ones. Advice for CEOs, how to build a board?

Roelof Botha: I think the first financing, when you get an investor, if you’re getting an investor board member, you should treat it as a recruiting decision, not a financing decision, because they’ll have a much bigger bearing on the ultimate outcome of your company. And then I’m generally a fan of getting a very good independent board member within a year or two.

Brian Halligan: Okay.

Roelof Botha: Certainly by the time you get product market fit. And I think there’s a different relationship that the founder has with the investor board member by virtue of what Jack described. Sometimes that person may come to the conclusion that the founder is no longer the right person to run the company, maybe rightly, maybe wrongly. If you can get an independent board member, there’s a different relationship that the founder has with that board member. And especially if that person has previous experience, it can be a fantastic mentor relationship to help the founder on that journey, depending obviously on their level of experience.

I think boards are often built too late in a rush, especially in the run-up to an IPO where people suddenly realize, “Oh, I’ve got a four-person board and I need nine.” Or whatever the case is. And you suddenly assemble people who have no context, they have no history, and they have no chemistry. Because you will be tested. You’re going to have a situation where there’s a short seller report, or you’re dealing with a hostile situation with an activist investor, or a tricky financing that really tests the mettle of the team. And you want to understand the dynamic between the board members, and just their willingness to go along and their alignment with the core values of the business. And so I just think it’s one of those things that requires a lot more care than I think most people apply to it.

Brian Halligan: Yeah. Jack, you’ve started a couple of great companies here. You’re kind of startup founder, scale-up CEO.

Roelof Botha: Brian, he was the only person to have founded two companies that made it into the S&P 500.

Brian Halligan: Oh, that’s amazing.

Roelof Botha: And the only person to have been simultaneously CEO of two public companies.

Jack Dorsey: For the record, which should not be a goal for anyone, by the way.

Brian Halligan: Can I ask you what you recommend? He’s CEO of two companies. Is it ever a good idea?

Jack Dorsey: Not public companies. Private, maybe. I think there’s probably going to be more of a trend where people are leading multiple companies that are private, but public companies, that should be like an anti-goal for any pattern.

Brian Halligan: What can founder CEOs learn from, like,—what did you do right? What did you get wrong? What advice do you have for that 100-person company CEO that’s growing really fast? Yeah, what do you have?

Jack Dorsey: My only regrets in life and also in our businesses are where I decided not to learn something.

Brian Halligan: Okay.

Jack Dorsey: Because I embrace all of our mistakes and all the bad decisions we made, but if I’m not learning from that, actively learning from it, that’s what I regret. And probably the worst case in any of these companies, just delegating way too much, especially within Block, because I wanted to set a structure where we had multiple CEOs in this company, but I realized, oh man, we’re just building like a holding company now. And, like, we got the CEO over here for Square and CEO over here for Cash App, and the value of our company is not these unrelated things that are growing at different clips. It’s how do we bring them together and really challenge the whole financial network entirely. Because we have both sides of the counter, so why aren’t we structured that way? And that, I think, led to just very differing cultures and values and execution levels. And that was a mess.

So I think the one thing that I probably consistently would have corrected would be just delegating too much. Too much of that. And I didn’t learn that fast enough. That’s a regret that I didn’t choose to learn from that fast enough. But when you have your entire company’s legible, it’s a very different equation. And I think my regrets going forward, if I were to predict them, would be like, am I actually putting enough entropy into the system, enough of the intent into the system to actually keep us relevant going forward? And that’s hence the shift. Like, I can’t imagine doing anything bigger than rebuilding our company as an intelligence, or more correct given where everything is trending. So it just feels like I have to constantly build and constantly learn from whatever we’re putting out there in order for us to stay relevant going forward.

Roelof Botha: So there’s one anecdote that came up, Jack, last week, which was how different meetings are today. Maybe you can talk about how frequent meetings are taking place now, and what’s the color? What’s the nature of the meetings today versus what they were a year ago?

Jack Dorsey: Well, just two months ago, every meeting that we would have—you’d have this, Brian—you would see a presentation or a Google Doc and we’d go through it. Now everyone is bringing a prototype that they built. Which is pretty amazing. And it’s either simulated data or real data, but it’s a cut on their work in a way that has far more depth and realism than we could ever get from a slide deck. And because they can actually modify it in real time, we can have a conversation around what they’re actually building in real time.

So the breadth that we get to explore is suddenly incredible, and that allows us to really—again, it goes back to judgment, like, which thread are we pulling on now? Because we can see everything in the horizontal. Where do we want to go deep? And what is the right path? And the cost of being wrong on that path and going back up the tree and going down another path is getting closer and closer to zero, because the tools can explore the path so quickly and then we can go down them much, much faster.

Brian Halligan: I completely agree with you. Like, a lot of times in HubSpot’s history, what worked was when we were doing a lot of different stuff and we were distracted.iI’s like, “Let’s just get focused.” And then we made progress. I see the startups these days doing more things in parallel and just being more productive and getting more done. And I used to preach focus. I don’t preach it as much anymore. Do either of you have a reaction to that?

Jack Dorsey: Yeah, I think it’s having a wider perspective to start. And then in the past, if we were to explore different paths, it would be a very costly exercise, especially within hardware, for instance.

Brian Halligan: Take you a long time to build that prototype.

Jack Dorsey: But today we can do it in an hour.

Brian Halligan: Yeah.

Jack Dorsey: And so I do encourage more exploration, but I think focus on getting the details right when we do choose that path. And it’s the 80-20 thing, which is like, these tools will build about 80 percent of where we need to go. And then that last 20 percent is going to be a function of how good our creativity is, how good our taste is, how good our judgment is. And just constantly pushing these models to doing something we didn’t think they were capable of—that’s where I think the magic still happens and where I think the focus still comes to bear. Because at the end of the day, right now you have to pick something to put out there because we do have a road map. But when you remove that limiting factor, as I said, and you focus on building the four things instead—the capabilities interface, proactive intelligence, and the world model—then it just changes everything. So I don’t even know if the question matters anymore.

Brian Halligan: Yeah. A lot of CEOs are struggling with the second act, and you’ve done amazing second act work at Block. You did interesting stuff with Bluesky, interesting stuff with Spiral. Advice to CEOs trying to figure that second act out?

Jack Dorsey: I don’t know if I ever considered it to be like a second act. It’s just something that I wanted to do and I had to do, and it was interesting.

Brian Halligan: Now you’re building something new. It’s distracting to the org and like, how do you resource it?

Roelof Botha: Well, Cash App was like that in the early days.

Brian Halligan: Yeah.

Jack Dorsey: That’s a good point. So I think every leader has to be comfortable with losing credibility with their stakeholders at some point in order to do something interesting. Like, we had multiple moments—and these are the founding moments that I think are critical for a company—but we started with a card reader. Eventually we determined that hey, we should probably lend money to sellers because no seller wants to accept credit cards. What they want is to get more sales. And what helps them get more sales? More capital to deploy into their business. When we first brought it to our board, our board said absolutely no. You’re not getting in the lending business. That’s ridiculous. And I lost some credibility with the board and our population because we wanted to do this. And we kept pushing it and pushing it. And eventually they said yes.

Cash App was the same thing where we were about merchants. Our mission was make commerce easy. And we built this thing that allowed effortless peer-to-peer, as effortless as just sending an email to start. And our COO at the time was on the founding team of PayPal, Keith Rabois. And even he said no. He said, this is a solved problem. Everyone in the company hated Cash App—it was a team of eight people—and hated it for two to three years. We mentioned it less than eight times in our S-1 to go public. Our investors didn’t understand it at all. And every day that I allowed it to persist and defended it, I lost credibility. And I knew that I could earn it back if we saw success there. And we did. Like, we monetized it and it became profitable. And it’s now over half our business.

And so I think it’s getting comfortable with, like, you’re going to lose credibility. And if you have an understanding of how to earn that back, it’s okay. And you don’t have to care about what people think if you have the principle of why it’s important and why this needs to exist. And you’re okay with, yeah, people aren’t going to trust me for a bit and it’s okay. I’m staking part of my reputation on this and this is why I believe it. I think it makes all those answers stronger, by the way.

Brian Halligan: I have a weird story for you. When Sequoia was hiring me—they write a memo when they’re investing in a company or when they’re hiring someone. And the memo on me was one of my strengths was I was DGAF, don’t give a flock. And one of my weaknesses was I was DGAF, I don’t give a flock. You strike me as someone who has high DGAF, and you stick with your convictions for very long periods of time. Founders struggle with that. I struggle with that. Advice?

Jack Dorsey: Yeah, I would say it wavers for me. It’s definitely—I get a lot of hate, a lot of pushback, a lot of challenges, like, internally, externally. But again, I made a decision some time ago. When I first became CEO of Twitter, everyone was telling me I needed a CEO coach. And I got the CEO coach and he was a great guy, but I was learning absolutely nothing. And it just reminded me of all these times when you put so much emphasis on, like, who’s my mentor? Who am I learning from? Who’s my mentor? Who am I learning from? And around that time, I just decided I’m going to shift my mindset, and every single person I talk with, every single encounter I have, every single problem I face, that’s my mentor. And for it to be a mentor, I have to decide that I’m going to learn something from it. Like, every encounter I have is trying to teach me something, and what am I trying to learn from it? And just I would force myself to write it down every day, and every encounter, just what did I learn from this?

And again, my biggest regrets are when I decided not to learn something from it, because it’s likely that I would have repeated it or whatnot. So even the negative feedback or the credibility loss is a teaching moment. And it’s just a decision of, like, am I learning from this or not? And that allows you ownership over it. It just gives you agency over all this stuff. Like, what is this thing trying to tell me right now? What am I ignoring? What am I being stubborn about? And sometimes I get to the right answer, sometimes I don’t, and I just continue in my ways and it’s a failure. But just having that mindset, instead of having this one mentor in your life, now you have infinite mentors. It’s just an amazing way to approach life and challenges that I’ve found.

Brian Halligan: You’re definitely a learner, and talk a lot about it. You’re a meditator. Should all CEOs meditate? What are the benefits you get as a CEO? And what do you take from Marc Andreessen talking about how he’s not introspective? I thought that was an interesting comment. Talk about meditation, CEOs, what do you get from it? Yeah.

Jack Dorsey: Him saying that he’s not introspective is very introspective of him.

Brian Halligan: I thought that was interesting.

Jack Dorsey: Just to be clear. I do get a lot from that. I do think when people think of meditation, they think of this woo-woo person in the desert. And I’ve been characterized as that. And looking at the clouds and, like, imagine the clouds going by and your thoughts with the clouds and, you know, make them dissipate. But if you actually get into true meditation, it’s a very physical thing. It’s a very physical practice, and what you’re doing is you’re training your mind to focus on one point. One point. Like, the meditation retreats I did were 10 days, and you spend the first three days sitting from 4:30 in the morning until 9:00 pm, focusing on the feeling of your breath on your upper lip.

Brian Halligan: Yep.

Jack Dorsey: Just that, and just the sensation of it. And what you’re training your mind to do is to sharpen your focus, and then just to observe. Observe the sensation without reacting to it from an emotional or intellectual standpoint. And then the next seven days, you go up and down your body and you’re scanning for sensations like pain. And you’re sitting cross-legged, and you can’t move for three hours at a time. And it’s super painful. And you actually observe this pain, and you’re constantly with this mindset of, like, this isn’t permanent. If I were to stand up, it goes away. And it’s just that training your mind to recognize everything is impermanent. There’s no need to suffer or be attached to something that’s going to go away. And you’re doing it in this very small physical way, but then you apply that whole concept to your whole life, every emotion or reaction or encounter you have.

So I would recommend it only because it sharpens your focus. It sharpens your power of observation, and it diminishes your instinct to immediately react to things and to actually see them for what they are and then choose how you want to act with that information. So if you think about it as woo-woo, head in the clouds, then that’s what you’re going to get from it. If you see it as a physical practice to make your mind stronger, you’ll get that. And that’s what I see, and that’s what you practice.

Brian Halligan: Maybe just close on—start with you, Roelof. There are some timeless qualities of CEOs that last the test of time. And Roelof, you’re involved with YouTube, Instagram, Block, Mongo, Unity. What are timeless CEO qualities? And what is new? Like, what are the new qualities CEOs need today?

Roelof Botha: I like acronyms, so I came up with one which is ALE, A-L-E, which is not a very pleasant drink for most people, but anyway—authenticity, logic, and empathy. So authenticity, are you pretentious? Are you who you—do people see who you really are? Do you behave authentically? Are you logical? Are you predictable? Are you rational? Would you fly off the handle? And are you empathetic? Do you really care about the team that you manage? Do you really care about the business? Sort of the opposite of being a sociopath, perhaps, but deep empathy. So I think of those three qualities. I mean, there are many more that one could list, but I think it’s just hard to keep it in your mind. So for me, those are the three most important: authenticity, logic and empathy.

I think when it comes to dealing with humans, most of those things stay the same. And I remember how many of us thought the world was going to be so different in the midst of COVID. And I listened to a talk that Steven Pinker gave, and he talked about how probably things are going to go back largely the way they were before. And I think the same is true here. Yes, companies are being built differently. Yes, AI is absolutely transformational. It’s going to upend so many industries. I think it’s the biggest drainer of moats companies have ever seen. But some of the basics of dealing with people and leading remain true. The one I would say is probably different is the pace of change is so fast. And I think kudos again to Jack for the speed with which we’re moving on this decision, because it would have been easy to dither for six or twelve months on this decision. So you’ve got to move fast.

Brian Halligan: Jack, thoughts on that? Like, you’ve hired some amazing people in your career that have gone on to do some amazing stuff. What do you think? What’s timeless? What’s changed?

Jack Dorsey: I value someone who’s able to reprogram their mind and assumptions constantly. I mean, this is stated a lot, but just being able to question your own requirements, your own assumptions and your own decisions, or how rigid you are towards your past, the company’s past and its sacred cows, or what the competition is doing. And just being able to go wild for a bit, and then also being able to get that entire corpus down to something that’s actually manageable and that can be articulated in a way that other people understand. I think that’s extremely valuable.

Brian Halligan: Has it always been valuable, or is it more valuable because things are moving so fast right now?

Jack Dorsey: I think it’s more valuable. I mean, I think it’s going to be so easy to go along with the momentum of what’s happening around us today, and it’s going to be increasingly hard to break free of that momentum given what the tools do. And, like, this is the way we do things. And I think people will, because we’re offloading some of our intelligence to intelligences, be more likely to default to what these things are suggesting rather than seeing them as an input. Like, I think we’re still in a mode where most people are seeing what the intelligences do, what these tools do as output rather than better input to create better output ourselves. And I think that’s important to me. Like, when I was doing that every day, three hours, like, this is input to me, and it’s now up to me to make better output from all this new input that I have. And the ability to just take all this and see it at once, it’s just phenomenal.

So having someone who’s able to discern signal from noise and cool from not relevant—this is highly overused right now, but the taste thing is real. And it’s not just, I know what things look good together. It’s more like, do I have a point of view? Do I have a perspective and an opinionated drive to get it there? And is it relevant? Is it more relevant than what else is out there? And I think that’s critical. That’s what any founder is doing is like, I’m building something that didn’t exist in the world because I wanted to see it there. And because it didn’t exist is why I’m building it. And I think right now you’re seeing a lot of companies that are just copies of copies of copies of copies because it’s easy. Instead of, like, what’s your point of view? What is opinionated in this? And where is it pushing the boundaries and where is it uncomfortable?

Brian Halligan: I think that’s brilliant. It’s a great place to end. Thank you both for coming on Long Strange Trip. I love the article you wrote. I think it’s going to be game-changing for lots of companies. Appreciate you both.

Jack Dorsey: Thank you.

Roelof Botha: Thank you, Brian. Thank you, Jack.

Jack Dorsey: Thank you.

Takeaways

Brian Halligan: Hope you liked that. I really enjoyed speaking to him. He’s an unusual Homo sapiens, and he’s got some interesting thoughts. I think his ideas on how to transform the way you build a company and rethink the hierarchy kind of make sense to me. And I feel like at some point in the future, it’s somewhat inevitable that this kind of thing’s going to happen. And I sort of think of it as like, when I grew up in my career, I worked at this company PTC in the ʻ90s. It was very, very manager mode, very hierarchical. The power rested in the Vps, essentially. When I ran HubSpot, they didn’t call it founder mode then, but it was kind of founder mode. Instead of being a pyramid, it was flat. And a lot of power was rested in the founder’s hands.

He’s sort of proposing the Dorsey mode in my mind. He laughed about it when I said it, but I think of it as what’s next. And it’s more like a circle than a really flat organization. And the power rests kind of in the system. And the system makes a lot of decisions and it can react real time to the employees and the customers. But I think of Dorsey mode as getting rid of the hierarchy altogether, building basically the brain, getting the inputs right, and having it make a lot of the decisions that hierarchy used to.

I think he’s on to something. I’m curious to see what you think. Comment on Twitter or comment on YouTube. I’m curious about your thoughts on it. I think Jack would be curious too. He’s in the very early innings of rolling this out, and he’s looking for feedback on it. Anyway, appreciate you all. Thanks for tuning in.