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

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 for it? 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 was coming from a place of like, wow, is there our company just going to be completely irrelevant, you know, in the next coming years. 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 like that today. And that's pretty cool. Also, Rula Bohta, who's a squad 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 call from hierarchy two intelligence. And it's a manifesto on how to rethink. Basically, we think from the first principles, how an organization works. How do you completely eliminate hierarchy? And how do you put a eye rate 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 love to get some feedback from you and from other people on this. So if you get comments on it, let a rep. 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 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 you really dig in and when 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 I found Jack that a really nice job and in real life to two. Let's get into a 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 Hubsbot, companies like Block? Like what kind of led you to this? I don't know if there's one thing that's ultimately wrong. It's just it's recognizing that like what do we see in the pattern? What is the function of the hierarchy? And what we want to do explore is just like what 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 breath 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 2000 years. And now we're facing this I think a completely foundational moment in being able to question every element of how we work. And the one that I think is question the least is probably the hierarchy and probably about how we manage communication flow around the companies. So if we're in a world where we are today where block for instance is completely remote first, 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 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 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 the 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 it really opens the door for what's possible. Like roll-off and I have a board meeting every quarter where we we contract 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 giving them like fully rag FD possible information that is on their timeline with 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 art context in the structure of the company is ultimately going to terminate its velocity and how well it's road mapped for customers correct. You're just kind of drilling down on it. Can you just 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? Yeah, 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. And I would say our max depth right now is probably five. Okay. 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 where everyone in the company reports to me. And that would be, you know, all six thousand of other company. And that feels somewhat 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 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, like, you know, 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, you know, one person can, you know, potentially do the work or explore the breath 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 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 than the operators, the ICs. The second role is the DRI. And that's someone who can own the customer outcomes. We're putting a strategy together. They're understanding what roadmap 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. You know, 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 coaching skills, at 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 these where I see 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 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 teach in our way, but they don't necessarily need to be a DRI. And I in very rare cases, one person can take on all three of those roles. I 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 expected a build as an IC or operate the company. They're expected to be strategic and actually think about roadmaps and customer outcomes. And they're expected to coach and help raise the skill level around them with the people that they work with their with their directing. Just a little kind of before and after and you're you're mid on this unless pretend like it's working great and it's due here for now. And it's extremely flat. Like what is what is the role of the CEO before and after? I was at most of the listeners by the way, or CEOs. What does like 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 kind of before and after is in your mouth? I think 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. 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 and 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 have those elements. Certainly, but I think it's more about like the architecture of how the company as an intelligence works. And like if we're building the company as an intelligence, our job is as humans and my job is CEO is to constantly align it to where we think the right outcome is. And I see like, you know, visually I see the the company, the intelligence, the world model for the company in the center. And then on the edge of the humans who are just constantly aligning this towards customer outcomes. 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 going to 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, we 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 in a dashboard. We have cash out, we have title, we have the key, 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 roadmap 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 for your business 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 rents and they can pay the spot if I bill and they can pay their kids allowance and and this is all sequenced in a way that allows them to never go to zero, never go negative and have some question that allows them to even think about getting to saving or building wealth and that just, you know, peace of mind, I think is 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 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 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. And then the final layer is the world model. It's the customer world model. It's a company world model our deep understanding of our of ourselves and and also our customers. But I think like if I had to, if I had to say one, one thing that, you know, myself or anyone in the company has to do. It's, 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 a unique or is it not. And 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 work day, somebody who doesn't have the quality signal, the frequency of signal. Does it apply or doesn't work as well? I think it probably does it. I think 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. 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 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 think it's going to be a 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 just, you know, since January of 2024, which is one of these tools really came to bear like goose, which is an agent coding harness was one month before code code in January of 2024. And cloud code came out that following month and then like was really put into out of beta in May of that year. 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 and every single day it worked like every single day I was surprised. And it's, you know, it's it I'm sorry it wasn't 24 is 2025. It's only been a year of those tools. Like one year, it's just that 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 don't think people are feeling it enough. If they're just living in this abstraction, like, oh yeah, like 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. I think you're right. I think the people are thinking of as co-pilot 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. So what I've had is I've listened to that so far. In one of the 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 need to optimal outcomes. But you need to have the right framework in the right system. I think the way that many companies work today. is a little bit more commoner control. - Very much. - And you have hierarchies and you have political actions and people, you know, 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're long for the days when there were 100 people or not 500 people because there was 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 far smaller number of people that are former productive years, but is 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 gives their product to prove, 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. - 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 know, Rulaf. I sort of think of, 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 optimizing for growth rate, growth profit per employee, and it promoter school, 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. - Yeah. - There's so many small people in your company that have clever ideas that every day inflict the product, introduce something new. And so this idea that there's just, you know, one person who is the brilliant person who comes up with everything, I just don't think, you know, I don't believe in cure a worship or the conduit of 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, 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, 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. Delaney, it's 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 just, you know, we weren't able to get to that level of the data for the L.D. 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 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 like, 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 do that. And I think all these things are gonna blur. That, I mean, that's the craziest thing is like, you know, again, since last year, I've just had this existential dread and also like hope and optimism in the same hour in the same thought process of like, what is it, what is even a company going for it? Like what, like what are these structures going forward? Yeah. And it was coming from a place of like, wow, is our company just gonna be completely irrelevant? The, you know, in the next coming years, or even sooner, like what do we, 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 like, what are the, 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. You'll 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 on interface with the square APIs. And we're seeing cash app customers. And these are like, not tech people. These are just like people, I want to, I want to bot to help me band my life. That agency, independent of your thoughts on like how could a system open clause right now would look it better and better. But the intent behind that is agency. I want to tangibly control this intelligence and for it to better. 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 factors of company is our roadmap. Like we need to remove that from the equation. We need to ensure that our customers are truly building alongside us. - Really? - And that they, you know, are seeing us as a series of capabilities that makes their desires fast and easy and invaluable. So like it really goes back to 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 be 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 door for my book? - I don't know about this door. See, playbook, thank you. - But we don't have it all figured out. I think there's an important purpose of humility that we have to bring in the path. We believe it's right. We know there's a lot to figure out. - Yeah, it's more like if you were to, at 100 people or even, you know, just starting today, if you were to build your company as an HCI, 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 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 just like, 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, you know, like there's, there's, there's, you know, apps, for instance, and websites and, like the traditional retail, there's a number of things that 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 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 like really question, like do I need a hierarchy? Like Brian, a year in the square, I also, we removed titles, we normalized everyone to lead. 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. Yeah, so we ripped up all the business cards, we normalized down to a title of like your 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, you know, we don't have titles, we have like, you know, what do you lead going back to like the DRI thing or do you ultimately respond to call 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, like what is actually fundamental to solving your customers problems and where is a hierarchy getting in the way of that? And look at all the tools you're using. Like look at all the information 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 because you're relying on people telling you things. And you know, that doesn't always happen for various reasons that you know, ROLF spoke to in terms of agenda or politics or emotions or empathy, all these things. If 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. Like that's the hardest bet is like we can determine causal, getting to predictability for these world models around the company and customer is just still right now very much a research but like it's one that you know, it's immunally 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 be, how bold should it be, you know, RuPaul, it's got this good line. If you're gonna, we can either shit sandwich, don't nibble and you seem like you took a big bite. What was that debate behind the scenes and then ROLF like how did he pitch it to you guys and what was the mortgage reaction just like behind the scenes on that. Yeah. So it was something you know, December of last year 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 gridfield 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 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 you build the company though 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 edge like, you know, 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 like small things. But if we were to really reboot and rebuild the company like would we end up where we where we looked today and the answer was uniform right now. And 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% 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, not work 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 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, hard not to, especially operating the way we have like I think going forward it will be much easier because more the company will be logical 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 that was a span of you know, exploration, the execution and you know, under 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 a 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 want to react to that. I want to I want to 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 to leave and even for the people that we're asking to stay. And we're not just reacting into something mediocre, we're you know, acting towards excellence and like that's just the tone that we wanted to set. So you know, every every day it was just like constantly checking like are we doing the right thing? Is this the right set of folks? Like like what are we not thinking about? What are we not talking about? And we you know, we kept it 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 more than open more like yes, we agree like we should we should do this, but I'll I'll roll off speak to that. Was a very quick process. Okay. I think part of what helps is that Jack had written us a very detailed note. Lying out the logic, it's principled. It's not really 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 the 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. You know, some of some of where we started in the first of those three weeks, a different form where we ultimately landed by the time the announcement took place. And also I think it's an example of where we built enormous trust between the board and the management team. And 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 and quick succession to make sure we drilled in on the key issues and the board was fully supportive. You too, Rulof, you've been on a lot of boards, Jackie, you've had your ups and downs with different boards. Any advice for these CEOs listening that should they start bringing it 100 employees should they start bringing it independent? Like how do you build an amazing board that really serves the company well, the employees well, the investors well, the customers well. Like what's your advice on that? I mean early on, I always told myself and my team that like your first board is your investors, right? And I would treat that relationship as a higher 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. And again, they can fire you. And for me, it was around, you know, 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 for the person. And you know, that's why Rulof, you know, we were optimizing for him to be on our board and being an investor, but like it was it was the fact that like he would up level our conversation, up level 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 is a 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 to board? 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 going to 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'd 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% rip or 20% rip 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 a wall and like it just feels like losing constantly. And I, you know, I had a conversation with a board of what I don't want that like that's not, I don't want to be at a company like that. Like it's just, it doesn't make sense. It's soul crushing, you know, 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 what's what's going on? Let's challenge it. Little off. You're on a lot of boards. You're on some really good ones. Advice for CEOs out of the board. Well, I think the first financing when you get an investor, if you're getting an investor board, [BLANK_AUDIO] 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 Euro 2. 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 it sometimes. You know, 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 mental 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 4% board and I need line," 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 mental of the team. And you want to understand the dynamic between the board members and just stay willingness to go along in 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. Jack, you've started a couple great companies here. You're kind of start up founder, scale up CEO. Brian, he was the only person to have founded two companies that made it into the S&P 500. Oh, that's amazing. And the only person to have been simultaneously CEO of two public companies. Okay, Jack. Then this should not be a should not be a goal for anyone. I mean, he's a good. Is it ever good? Yeah. Not public companies. Yeah, 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 I should be like an anti-cool to 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 that's growing really fast? What do you got? My only regrets in life and also in our businesses are where I decided not to learn something. Okay. Because like 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, that's what I regret. And in 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 like the see over here for square and see over here for cash up and the value of our company is not like these unrelated things that are growing at different clips. It's how do we bring them together and like, you know, really challenge 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 must. So I think the one thing that I probably consistently would have corrected would be just delegating too much, you know, too much of that and I didn't learn that fast enough. That's a regret is I didn't choose to learn from that fast enough. But when you have your whole 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 like 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 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. Maybe you can talk about how frequent meetings are taking place now. And what's the color? What are the nature of the meetings today versus what they were you're about? Well, I mean, just two months ago, every meeting that we would have would come, you have this brain like you see a presentation or a Google doc and we 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's far more as far more depth and realism than we could ever get from a slide deck. And because they can actually modify it real time, we can have a conversation around like what they're actually building in real time. So like the breath 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 want to go like deep and like what is the right path 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 completely agree with you like a lot of times in Husqvar's history what work was when we were doing a lot of different stuff and we were distractions 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 ever reaction that? Yeah, I think it's having a wider perspective to start and then like because in the past if we were to explore different paths like it would be a three, it'd be a very costly exercise especially within hardware for instance. For a long time to build that prototype. But today we can do it in an hour. And then so I do encourage more exploration but I think focus on getting the details right when we do choose that path and like it's the 80, 20% thing which is like you know these tools will build about 80% of what where we need to go. 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. And just constantly pushing these models to doing something they weren't we didn't think they were capable of. And 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 you have to right now you have to pick something to put out there because we do have a roadmap. 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 in the world model, then you know it just changes everything. So I don't even know if the question matters anymore. Yeah, a 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. Are you building something new? It's distracting to the org and like how do you resource it? Well, cash up was like that in the early days. Wow. Well, 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. When we had multiple moments and these are the founding moments that I think are critical for our company. But like we started with a card reader. Eventually we determined that 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 the lending business like it's ridiculous. And we lost, 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 up 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. This effortless is just sending an email to start and our COO at the time was on the the founding team of PayPal, Keith, Roboi. And even he said no, and he said, like, you know, this is a solved problem. Everyone in the company hated cash up. There was a team of eight people and hated it for two to three years. So we mentioned it less than eight times in our S1 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 like, how to earn that back, it's okay. And you don't have to care about like 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 sticking 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 weird story for you. When Sequoia was hiring me, they write a memo when they're investing in the 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 that a 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, found your struggle with that, I struggle with that. Advice. - Yeah, I would say it wavers for me. Like 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 like 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 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 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 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 this 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 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 a, it's just an amazing way to approach life and challenges that I found. You're a definitely learner and talk a lot about it on other, I've seen you talk about a lot. You're a meditator. Should all CEOs meditate? What are the benefits you get as a CEO? And what do you take from Mark Andreessen talking about? How he's very, he's not introspective. I thought that was an interesting comment. Like, talk about int meditation, CEOs. What do you get from it? Yeah. Him saying that he's not introspective is very introspective. I thought that was interesting. Just to be clear. No, I don't, I didn't get a lot from that. But 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 are 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 meditation retreats I did were 10 days. And you spend the first three days sitting from 4.30 in the morning to 9 p.m. focusing on the feeling of your breath on your upper lip. 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 and 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-leg 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 concy 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 like recognize everything is impermanent. There's no need to suffer or be attached to something that's going to go away. Like, 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, 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 like a 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. - You may just close on, start with you, RELOF. There's some timeless qualities of CEOs that last the test of time. And RELOF, you're involved with YouTube, Instagram, block, MongoUnity. 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 AL, ALE, 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? Any empathetic? Do you really care about the team that you manage? Do you really care about the business? 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 gonna be so different in the midst of COVID. And I listened to a talk that Stephen Pinker gave. And he talked about how probably things are gonna go back largely the way they were before. But I think the same is true here. Yes, companies are being built differently. Yes, AI is absolutely transformational. It's gonna up in so many industries. I think it's the biggest trainer of most companies that they've 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. Right here. And I think, you know, could us again to Jack for the speed with which we're moving on this decision 'cause it would have been easy to dither for six or 12 months on this decision. So you've got him and fast. Jack, thoughts on that? Like when you've hired some amazing people in your career that have gone on to do some amazing stuff. What do you think? And what's changed? What's time was? What's changed? 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 requirements, your assumptions and your own decisions or how rigid you are towards your past, the company's past and sacred cows, or what the competition is doing. 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 then 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 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. And people will go along with more likely to do. default to what these things are suggesting rather than seeing them as an input. I think 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. I think that's important to me. When I was doing that every day, three hours, this is input to me. It's now up to me to make better output from all this new input that I have in the ability to just take all this and see it at once. It's just phenomenal. 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. 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 in an opinionated drive to get it there? Is it more relevant than what else is out there? I think that's critical. That's what any founder is doing. I'm building something that didn't exist in the world because I wanted to see it there. Because it didn't exist is why I'm building it. I think right now you're seeing a lot of companies, there are copies of copies of copies of copies because it's easy. What's your point of view? What is opinionated in this? Where is it pushing the boundaries and where is it uncomfortable? I think that's brilliant. It's great place. Thank you both for coming on LongStrange Shrip. I love the article you wrote. I think it's going to be game-changing for lots of companies. Appreciate you both. Thank you. Thank you, John. Thank you. I hope you like that. I really enjoyed speaking to him. He's an unusual, homo sapien. He's got some interesting thoughts. I think his idea is on how to transform the way you build a company and rethink the hierarchy. They make sense to me. I feel like at some point in the future, it's somewhat inevitable that this kind of thing is going to happen. I think of it as when I grew up in my career, I worked this company, PTC in the 90s. 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. 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 like, what's next? It's more like a circle than a really flat organization. The power rests in the system. The system makes a lot of decisions and can react real time to the employees and the customers. 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 on YouTube. I'm curious about your thoughts on it. I think Jack would be curious too. He's in the very early endings of rolling this out and he's looking for feedback on it. Anyway, appreciate it Wall. Thanks for tuning in.