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

Since last year, I've just had this existential dread and also, like, hope and optimism at in the same hour, in the same thought process of, like, what is even a company going forward? Like, what, like, what are these structures going forward? And this is the only like durable one structure that I could actually imagine lasting for quite some time. And it it was coming from a place of like, wow, is our company just gonna be completely irrelevant, you know, in in the next coming years. Alright, 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 and P 500. Just learned that today. That's pretty cool. Also, Rulav 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, a call from hierarchy to intelligence. And it's a manifesto on how to rethink, basically rethink from the 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 get comments on it, let it 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, like, CEO advice. I work with lots of CEOs, as you folks know. Like, how do you build an amazing board? He certainly got some scars around board building. How do you build your second act, like the Cash App versus the the original business of 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 kinda 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 and really left it too. Let's get into it. 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 kinda led you to this?

I don't know if there's one thing that's ultimately wrong. Mhmm. It's just it's it's recognizing that, like, what what do we what do we see in the in the pattern? What what is the function of the hierarchy? Mhmm. And what we wanted to explore is just like, what where does it actually come from and and why did 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, you know, we've borrowed and iterated on a little bit over two thousand years. Yeah. And now we're we're facing this, I think, a 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 companies. Mhmm. So if if we're in a world where we are today, where Block for instance is completely remote or we're remote first Mhmm. Every single thing that we do creates some sort of artifact, whether it be a Slack message, an email, pull request, code, you know, all these Google document, a meeting that we record, all these things have these artifacts of information about how the company is 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 it. 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 and same understanding of, like, 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 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 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 and we can also have everyone in the company query it as well. And and it just it really opens the door for what's possible. Like, you know, Roloff and I have a board meeting every quarter Mhmm. Where we 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 that meeting time that we 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, like, our earnings call and analysts. Like, you giving them, like, fully Reg FD possible information that is on their timeline with with their questioning. Mhmm. But you can scale this to any position or any role in the company, which is pretty phenomenal. And, like, we've just never had that ability before and and now we do. And, you know, I think the the architecture and the structure of the company is ultimately going to determine its velocity and how well its roadmap for customers correct.

Mhmm. Drew, just kinda drilling down on it, can you describe sort of what the organization looked like before? 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 kinda drill down a little bit into what Block looks like today and kind of where it's going. Yeah. We we we are early in it. I mean, just from a, you know, one one measurement of of how far along we are would be the depth from me to any other individual in the company. Mhmm. And I would say our our max depth right now is probably five k. Folks between me and and anyone in the company. I would wanna get that down to two to three this year. And in the most ideal case, you know, there there is no layer. Everyone in the company reports to me, and that would be, you know, all all 6,000 of of the company. And that feels somewhat, you know, ridiculous when you consider, like, 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 it it that goes into the roles going forward. We we wanna normalize down to just three roles. Mhmm. The first is an IC, which is a a builder or an operator. This is a salesperson. It's an engineer. It's a designer, product person, like, you know, whatever it is. They're actually working with the tools to build or to operate the company.

Mhmm. They're augmented because they have access to agents. So, you know, one person can, you know, potentially do the work or explore the breadth that, you know, it would take a team or, you know, 10 people to do in the past. So that's number one. And I 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 builder and the operators, the ICs. The second role is the DRI, and that's someone who can own the customer outcomes. Mhmm. They're putting a strategy together. They're understanding what road map allows us to solve customer customer needs and and problems. And they're assembling a team of these ICs to get something done. But the the durable human human skill there is ownership and accountability. You know, they're really owning the 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 these are people who might be ICs or they might be DRIs, but they're also really good at giving coaching skills at at a coaching skill to help the the people around them get better and better and master their craft. And today, that's a management structure where where these where ICs and even DRIs report to a player coach. Mhmm. 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 and coaching. And there's a lot of empathy there and, you know, all the all the soft skills that we recognize great managers are are known for, but but not making a requirement that they have to be strategic necessarily. They have to build because they need to show off the skill and and 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. Think I can take on all 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 with the people that they work with with their direct team. Just a little kind of before and after, and you're you're mid on this, and let's pretend like it's working great and it's two years from now, and it's extremely flat.

Like, what is what is the role of the CEO before and after? How's that most of the listeners, by the way, are CEOs. What does, like, planning look like before and after? What happens to all those people who are directors and managers or the kinda glue people? Like, what are it's kind of the before and afters in your mind? I think my my 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. Mhmm. And that's like hiring and firing and setting values and setting the culture and setting the tone. Mhmm. The second is to ensure that decisions are being made in 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 and to push ourselves in 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 in the future, you you have those elements, certainly, but I think it's more about, like, the architecture of how the the company as an intelligence works. And, like, if we're building the company as an intelligence, our job is as humans and and my job as CEO is to constantly align it to where we think the right outcome is. Mhmm. And I I see, like, you know, visually, I see the the comp 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. Mhmm. But even even that changes, I believe, because I think a company's ultimate limiting factor is its own roadmap. And I think what what these technologies point to are that our customers are going to they're gonna have the expectation that they can ask for a feature that doesn't exist on our roadmap and that it just is served to them. And that's where, like, you really get into the 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. Mhmm. 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, like, 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 have we're moving money. Money is the most honest signal in the world. You can lie about literally everything, but when a transaction occurs, like, that's that's something that, like, 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 asked. So we can do the very simple but very valuable thing of like, how do we protect our customers' cash flow? Like, 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 and 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 and that just, you know, peace of mind, I think, is the most critical aspect here. So if if we're enabling a customer if we're able to prompt a customer and also they can ask, like, as a business, hey. I have this inventory thing that I've been using, but it's missing this feature. Can I 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 roadmap. Yeah. So our our customers, just by using and talking with our systems, are telling us what our roadmap should be and then it's up to us to give the judgment. Mhmm. And then the final layer is is the world model. It's the customer world model. It's the company world model, our our deep understanding of our of ourselves and also our customers. But I think like, if I had to say one thing that, you know, myself or anyone in the company has to do, I guess it's this overused phrase of judgment. But it is judgment against like what we intend to build in the world. And is it on 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? Mhmm. I I guess in for my part, I'm the extra checkpoint on, like, is the alignment circle of humans, the edge of humans actually working correctly.

In this 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 it doesn't work as well? I think it probably does. I I think it it goes down to, like, are you building a are you building a business that, like, 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 or and if you are, then I think you can build your company as an intelligence. If you're not, then it's probably a an add on to something else. Mhmm. And I 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 this our whole company with this as the core? Like 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 I think it's gonna be very, very challenging to differentiate and and and survive. And and that's kind of what's been leading me to all this is, like, I I just you know, since January 2024, which is when these tools really came to bear, like, Goose, which is a agent coding harness, was one month before Claude Code in January 2024. And Claude Code came out that following month and then like was really put into out of beta in May.

Mhmm. And, you know, 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? Mhmm. And every single day it it worked. Like, single day I was surprised. And it's it's, you know, it's it I'm sorry. It wasn't 2024. It's 2025. It's only been a year of those tools. Like, one year. It's just the the compounding nature of this is pretty incredible. So, you know, being able to, like, see that, understand it, and then shift your company to be ahead of it, I think, is absolutely critical right now. And I I don't think people are feeling it enough. It it they're just living in this abstraction. I'm like, oh, yeah. Like, these tools will make everyone in our company 10 x more productive. I I don't think this is a productivity thing. I think it's a structural thing that needs to shift. I think you're right. I think people are thinking of it as copilots and individual productivity versus your I think your idea is complete business transformation, and I think it's super interesting and compelling. Can I add one Yes? Yes, please. Thought I've had as I've listened to this so far. One of my favorite pieces of writing ever is Adam Smith, 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. Very much. And you have hierarchies and you have political actions and people jockeying for position, 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 they 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. It's just, Listen, more customers want this than that. That's how we're going to decide what to build next. So really, some something quite magical in that realization.

Yeah. About four years into building HubSpot, I eliminated no 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 year. I have a theory I want to run by you, Roloff. Like, I sort of think of, of 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? Oh, I don't think the AI makes most of the decisions. I think that, 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 optimising 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 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. There's so many smart people in your company that have clever ideas that every day inflect a 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 to that where you sort of scapegoat people. I think it's harnessing the base of your team to really advance the company. So I subscribe to the circle idea.

Yeah, also don't think that AI is making the majority of the decisions. I think it's facilitating Okay. A more context rich decision. I I think ultimately, like, 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, delineates like where our roadmap should go and then it's up to our judgment as to whether that's consistent with what we wanna be and what we think is most strategic or not. But we we just you know, we we 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 do look at our customer support, you know, product feedback on on on Twitter, all these other things. But when your interface is a conversation with your customer instead of, like, this visual navigation, you suddenly get, like, 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 wanna be as a company or if they should be going elsewhere to to to do that. And then I think all these things are gonna blur. That I mean, that's the craziest thing is, like, you know, again, since since last year, I've just had this existential dread and also, like, hope and optimism at in the same hour, in the same thought process of, like, what is it what is even accompanying going forward? Like, what, like, what are these structures going forward? And this is the only, like, durable one structure that I could actually imagine lasting for quite some time. Yeah. And it it was coming from a place of like, wow, is our company just gonna be completely irrelevant. You know, in in the next coming years or or even even sooner. Like, what do we what do we actually differentiate on? What what do we have a a moat around? And what what do we need to be to defend and and also to to grow that? And, like, what are the and all all that falls from customer expectation. Like, it the most amazing thing about OpenCloud to me was that people wanted to take this thing and contain it into a Mac Mini Yep. 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. Mhmm. Interface with the the Square APIs. And we're seeing Cash App customers. And and these are, like, not tech people. These are just, like, people I I wanna I wanna bot to help me manage my life. That agency independent of what your thoughts on, like, how good of a system OpenAI is right now, it'll get better and better. But the intent behind that is is agency. I want to tangibly control this intelligence and and for it to to better and what it makes possible for me is incredible. And and that expectation floor has just risen dramatically. And and and that leads me again to, like, yeah, our 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. Mhmm. And and that they, you know, are seeing us as a as a series of capabilities that makes their desires fast and easy and Mhmm. And valuable. So, like, it it really goes back to the the capability set that we have. And then, like, the intuition of the interface that we have and then, like, how intelligent our world models can can be to to be helpful and to compose UI in real time.

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, you know, running the Dorsey playbook? I don't know about this Dorsey playbook thing, but But we don't have it all figured out. I think it's an important dose of humility that we have that we're delivering on the path. We believe it's right, but we we know there's a lot to figure out. Yeah. It it's more like if if you were to at at a 100 people or even, you know, 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, like, valley of dread about distribution Yep. And attention because there is so much noise out there. And it's so hard to get to the actual signal of, like, who's building something interesting that will actually fundamentally change something and will be around for more than a year. Yeah. It it just like I think distribution really becomes a differentiator and I think there's some of that horizon where the way we think about distribution today closes off. You know, like, there's, you know, apps for instance, and websites, and like, the the traditional retail. There there's a number of things that will will change, and if you don't have the distribution today, it's gonna 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 I would assume that a company of a 100 probably is no more than two to three layers deep, hopefully. And now would be the time to just, like, really question, like, do I do I need a hierarchy? Like, Brian, a year into Square, I also we removed titles. We normalized everyone to lead. Yep. We did it for like, 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. Like, we we, you know, we don't have titles. We we have, like, you know, what do you lead? Going back to, like, the DRI thing, what what are you ultimately responsible for? And I I think it's helped us a lot, but this is an another step. Like, if if you're starting today or you're a 100 today, like, what what is actually fundamental to solving your your customers' problems and and 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. Like, just putting that into an intelligence and being able to query it will give you an understanding of the company that, like, is two to three times more than you had before ever. Mhmm. Because you're relying upon people telling you things. Mhmm. And, you know, that doesn't always happen for various reasons that, you know, Roloff spoke to in terms of agenda or politics or emotions or empathy. All all these things if imagine if your company was entirely legible, like, 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. Like, that's that's the hardest bet is, like, we can determine causal getting to predictability for these world models around the company and and customer is is still, right now, very much a research, but, like, it's it's one that, you know, it it's imminently solvable.

Can you guys just take me behind the scenes? Like, Jack, this was a really bold move. You laid off 40% of your employees. Just like for CEOs listening, what was that debate inside? Like, how big it should it be? How bold should it be? You know? Ruth Porat's got this good line. If you're gonna 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 Rulof, like, how did he pitch it to you guys, and what was the board's reaction just, like, behind the scenes on that? Yeah. So it was something you know, December is when the is the when the models really got a, like, noticeable upgrade from being able to be really good at building prototypes and greenfield efforts to, like, understanding, like, large code bases and legacy code bases like our own. There was you know, hallucination wasn't much of a topic in terms of, like, the the coding ability and the tool harnesses, we became suddenly very mature, like, just in that month. And it just like, every 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, you know, we came back and the conversation was, like, just going around the table, would would you build the company the this way if you had these tools today? Like, what would the company look like? And everyone around the table in my team just said, like, it would not look like this. It would not be this size. It would not be structured this way. And we've been making, like, changes on the on the edge, like, you know, going from a GM structure to a functional structure to reduce like, putting a a cap on our layers to four, me plus four, and all these, like, small things. But if we were to really reboot and rebuild the company, like, would we end up where we where we look today? And the answer was uniformly no. No. And and then we just did this exercise of, okay. So what is the minimal number of people that we would need to keep the service up a 100%? And then next, what is the minimal number of people that we would need to be to to fully be 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. And, you know, it hard hard not to, especially operating the way we have. Like, I think going forward, it'll 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 it was that, and and and there was a span of, you know, exploration to execution in in, you know, under under three weeks. And I 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 wanna 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 will probably get to this realization at some point. I don't wanna react to that. I want to I want to I wanna 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 to to leave and even for the people that we're asking to stay. And we're we're not just reacting into something mediocre. We're we're, you know, acting towards excellence and and, like, that's just the tone that we wanted to set. So, you know, 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 with the board, which was, my perspective, very open to it and and actually more than open, more like, yes, we agree, we should do this, but I'll let Roloff speak to that.

It was a very quick process. I think part of what helps is that Jack had written us a very detailed note laying out the logic. It's principled. 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, 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 are different from where we ultimately landed by the time the announcement took place. I also think it's 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 shorthands 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.

You too, Rulaf, 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 that shouldn't they start bringing at a 100 employees, should they start bringing independence? Should they like, how do you build an amazing board that really serves the the company well, the employees well, the investors well, the customers well? Like, what's your advice on that? I mean, early on, I I always told myself and my team that, like, your your first board is your investors. Right? Yep. And I would treat that relationship as a hire you can never fire. And in fact, they can fire you and have 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. Mhmm. And then and again, they can fire you. And for me, it was around, you know I I think a lot of young founders kinda go for the brand names, especially around VCs, but I always wanted to go for the for the person. And, you know, that's why Roloff you know, we we were we were optimizing for for him to be on our board and be an investor, but, like, it was it was the fact that, like, 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 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 and 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 perspective on that and that is open to wild ideas. The things that are gonna just seem like crazy in the moment, which, like, this one might might be. But it can be rationalized if we talk through it and we, like, really document it and paint a picture of, like, where the where this could go and, like, what the opportunity cost is if we don't do something. Because, like, if we didn't do something like this, I just imagine, like, every year, it's a 10% rift or 20% rift or whatever it is. And, like, that is just the most demoralizing, like, crappy, like, non creative building of a company ever. And it's all, you know, with your backs against the wall and, like, it just feels like losing constantly. And I, you know, I had a conversation with the board and, I don't want that. Like, that's not I don't wanna be at a company like that. Like, it it's just it doesn't make sense. It's soul crushing, you know, and it's just not not inspiring, and I don't feel good about it. So here's here's what I do feel good about and, like, let's let's go. Let's let's challenge it.

Loloff, you're on a lot of boards. You're on some really good ones. Advice for CEOs how to build a board. 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, 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 realise, Oh, I've got a four person board and I need nine, or whatever the case is. Then 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. Yeah.

Jack, you've started a couple of great companies here. You're kind of startup founder, scale up CEO. Brian, he was the only person to have founded two companies that made it into the S and P 500. Oh, that's amazing. And the only person to have been simultaneously CEO of two public companies. Jack. Which should not be a goal for anyone, by the way. Can I ask you to recommend CEO of two companies? It ever Not a good public companies. Private, maybe. Private private, I would I would I I think there's probably going to be more of a trend where people are leading multiple companies that are private, but public companies, like, it should be, like, an anti goal to any any pattern. What can founder CEOs learn from, like, what did you do right? What did you just get wrong? What advice do you have for that 100 person company CEO? It's growing really fast. Like, yeah, what do you got? My only regrets in life and and also in our in our businesses are where I decided not to learn something. K. Because I, like, I I embrace all of our mistakes and all the bad decisions we made, but, like, if I'm not learning from that, actively learning from it, like, that's that's what I regret. And, you know, in in in in probably the worst case in any of these companies, like, just delegating way too much. Yep. Especially especially within Block because, like, I wanted to set a structure where we had multiple CEOs in this company, but I realized, oh, man, we're we're just building, a holding company now. Yeah. And, like, we we got, like, you know, the c over here for Square and c over here for Cash App and, like, the value of our company is not like these, you know, unrelated things that are growing at different clips. It's how do we bring them together and, like, you know, really, you know, challenge the the whole financial network entirely because we have both sides of the counter. So, like, 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 I think the the one thing that I I probably consistently would have corrected would be just delegating too much, you know, too too too much of that. And I didn't learn that fast enough. I think that's that's the regret is I didn't choose to to learn from that fast enough. But when you have your whole your whole your entire company's legible, it's a very different equation. Mhmm. 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, like enough of the intent into the system to actually keep us relevant going forward? And and that's hence the shift. Like, I I I can't imagine doing anything bigger than rebuilding our company as an intelligence or more correct given where where everything is trending. So it it just it 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.

So there's one anecdote that came up, Jack, last week, which is how different meetings are today. They're obviously maybe you can talk about how frequent meetings are taking place now. And what's the color? What what are the nature of the meetings today versus what they were a year ago? Well, I mean, just two months ago, every meeting that we would have would I mean, you you have this, Brian. Like, you see a presentation or a Google Doc and we go through it. Yep. Now everyone is bringing a prototype that they built Yep. Which is pretty amazing. And, like, it's either simulated data or real data, but it's a cut on their work in a way that's far more has far more depth and and realism than we could ever get from a slide deck. And because they can actually modify it in real time, like, we can have a conversation around, like, what they're actually building in real time. Mhmm. So, like, the the breadth that we get to explore is suddenly incredible, and that allows us to, like, really again, it goes back to judgment, like, which thread are we pulling on this now? Because we can see, like, everything in the horizontal. Where do we wanna go, like, deep? And, like, what what is the right path? And and the cost of, like, 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 also we can go down them much, much faster.

I 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. It'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 as I do, but do you ever either of you have a reaction to that? Yeah. It's a I think it's I think it's having a wider perspective to start and then like, because in in the past, if we were to explore different paths, like, would be a, you know, three it'd be a very costly exercise, especially within hardware, for instance. Take you a long time to build that prototype. But today, can do it in an hour. Yeah. And then so I I do encourage more exploration, but I think focus on getting the the details right when we do choose that path and, like, it's the 8020% thing, is, like, you know, these tools will build about 80% of what where we need to go. Yep. And then that last 20% is going to be a function of, like, how good our creativity, how good our taste is, how good our judgment is. Yeah. And and just constantly pushing these these models to to doing something they weren't they weren't we didn't think they were capable of. And that's where I think the magic still happens and where where I think the the focus still comes to bear. Because at the end of the day, have to 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, like, you know, the capabilities, interface, proactive intelligence, the world model, then, you know, it just changes everything. So I don't even know if the question matters anymore. Yeah. Lot of CEOs are struggling with the second acts, and you've done amazing second act work at Block. You did interesting stuff with Blue Sky, interesting stuff with Spiral.

Advice to CEOs trying to figure that second act out. I don't know if I ever considered it to be like a second act. It's just something that, like, we had what I wanted to do and I had to do, and it was interesting. Now you're building something new. It's distracting to the org and, like, how do you Yeah. Resource it? Well, Cash App was like that in the early days. Yeah. Well, that's that's a good point. Like, 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, when when we we had multiple moments, and these are the founding moments that I think are are critical for a company. But, like, we were we started with a card reader. Eventually, we determined that, hey, we should probably lend money to sellers because, like, 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. Like, you're not getting into the lending business. Like, it's ridiculous. And we lost I lost some credibility with with, you know, the board and our population because we wanted to do this and we kept pushing it and pushing it. Eventually, they said yes. Cash App was the same thing where we were about merchants. Our mission was make commerce easy. Mhmm. And we built this thing that allowed effortless peer to peer. Mhmm. Effortless is just, you know, sending an email to start. And our our our COO at the time was on the founding team of PayPal, Keith. Yep. And even he said no. And he said, like, you know, 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 we mentioned it less than eight times in our s one to 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 it if we saw success there, and we did. Like, we we monetized it and it became profitable and, you know, 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, like, how to earn that back, it's okay. You don't have to care about, like, what what people think if you have the principle of why it's important and why this needs to exist and and you're okay with, yep, people aren't going to trust me for a bit and it's okay. I'm I'm 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. I have a 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 I was DGAF, I don't give a flock.

You strike me as someone who's has high DGAF, and you stick with your convictions for very long periods of time. Founders struggle with that. I struggle with that advice. Yeah. I would say it waivers for me. Like, it it it's definitely I get a lot of hate, a lot of pushback, a lot of challenges, like, externally. But, again, it's I I made a I made a decision some time ago when I first became CEO of Twitter. Everyone was telling me I needed a CEO coach. Mhmm. And I got the CEO coach, and he was a great guy, but, like, I was learning absolutely nothing. True. And it 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 gonna 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 Yeah. To to for it to be a mentor, I have to decide that I'm going to learn something from it. Like, every every 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, like, write it down, like, every day and every encounter and just, like, 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 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. Like, it just, like it gives you agency over all the stuff. Like, what is this thing trying to tell me right now? Like, what am I ignoring? What am I being stubborn about? And, you know, sometimes I I get to the right answer, sometimes I don't, and I just, like, continue in my ways, and it's a failure. But I just having that mindset instead of having this one mentor in your life, now you have infinite mentors. It's like, you know, it's it's it's just an amazing way to approach life and challenges that that I found.

You're definitely a learner and talk a lot about it on other I've seen you talk about it a lot. You're a meditator. Should all CEOs meditate? Mhmm. What are the benefits you get as a CEO? And what do you take from Marc Andreessen talking about how he's very he's not introspective. I thought that was an interesting comment. Like, talk about meditation CEOs. What do you get from it? Yeah. Him him saying that he's not introspective is very introspective. Thought that was interesting. Just to be clear. Yeah. I don't I didn't get a lot from that, but I I do think to when people think of meditation, they think of, like, this woo woo, like, you know, 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 of the clouds and, you know, make them dissipate. But if you actually get into, like, true meditation, it's a very physical thing. Like, 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 the meditation retreats I did were ten days, and you spend the first three days sitting from 04:30 in the morning till 9PM Yep. Focusing on the feeling of your breath on your upper lip. Yep. 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 just like you're you're constantly with this mindset of like, this isn't permanent. If I were to stand up, it goes away. Mhmm. And it's just that that training your mind to, like, recognize everything is impermanent. There's no need to suffer or be attached to something that's going to go away. Mhmm. Like, and you're doing it in this very small physical way, but then you apply that whole concept to your 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 wanna act with that information. Mhmm. So if you think about it as like a woo woo, you know, head in the clouds, then that's what you're gonna get from it. If you see it as a physical practice to make your mind stronger Mhmm. You'll get that. And and that's that's what I see and that's what you practice.

Mhmm. Maybe just close on let's start with you, Rulaf. There's some timeless qualities of CEOs that last the test of time. And, Rulaf, you you're involved with YouTube, Instagram, Block, MongoDB. What are timeless CEO qualities, and what is new? Like, what are the new qualities CEOs need today? I like acronyms, so I came up with one which is ALE, A L E, which is sort of not a very pleasant drink for most people, but anyway. Authenticity, logic and empathy. So authenticity, I mean, are you pretentious? Do people see who you really are? Do you behave authentically? Are you logical? Are you predictable? Are you rational? Or do you fly off the handle? And you're empathetic. Do you really care about the team that you manage? Do you really care about the business? Or 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 But some of the basics of dealing with people and leading remain true. The one I would say is pretty different is the pace 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.

Jack, thoughts on that? Like, when you're you've hired some amazing people in your career that have gone on to do some amazing stuff. What do you what do you think? And what's chain what's what's timeless? What's changed? I value someone who's able to reprogram their mind and assumptions constantly. Mhmm. I mean, this is stated a lot, which is being able to question your own requirements, your own assumptions, and your own decisions Mhmm. Or how rigid you are towards your past, the company's past and sacred cows or what the competition is doing. Mhmm. It's just, you know, being able to, like, 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. Has it been valuable or is more valuable if things are moving so fast right now? I think it's more valuable. Like, being able yeah. 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 where 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 Yep. And people will go along with more likely to to default to what these things are suggesting Mhmm. Rather than seeing them as an input. Like, I I think we're we're still in the mode where most people are seeing what the intelligences do these tools do as output rather than better input to create better output ourselves.

And I'd like I think that's important to me. Like, when I was doing that, like, every day, three hours, like, this is input to me. Mhmm. And it's now up to me to, like, really make better output from, like, all this new input that I have and, like, the ability to just take all this and see it at once. It it's just phenomenal. So having someone who's able to discern signal from noise and cool from not relevant. You know? Like, there is there is this is highly overused right now, but the the taste thing is real. Mhmm. And it's it's not just like, 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 is it relevant? Is it more relevant than than, you know, what else is out there? Mhmm. And I think that's 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. Mhmm. And and because it didn't exist is why I'm building it. And I think right now, you're seeing a lot of companies, they're just copies of copies of copies of copies because it's easy. Yeah. Instead of like, what's your what's your point of view? Like, what is what is opinionated in this? And like, what where is it pushing the the boundaries and where is it uncomfortable?

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 gonna be game changing for lots of companies. Appreciate you both. Thank you. Thank you, Brian. Mhmm. Thank you, Jack. Thank you. Hope you like that. I really enjoyed speaking to him. He's an unusual homo sapien, 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, they 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 is 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 nineties. 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 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 like, what's next? And it's more like a circle than a really flat organization. And the power rests in the kind of in the system. And the system makes a lot of decisions and 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 the hierarchy used to. I think he's onto something. I'm curious to see what you think. Comment on Twitter or comment in on YouTube. I'm 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.