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

like what kind of led you to this? I don't know if um there's one thing that's ultimately wrong um 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 and um what we wanted to explore is just like where does it actually come from 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 um so being able to communicate over a breadth of of people and um 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 questioned 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, we're remote first, every single thing that we do creates some sort of artifact, whether it be a Slack message, an email, pull request, code, 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 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 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, you know, Roloff and I have a board meeting every quarter where we construct a bunch of board docs, slides, presentations. We get only so much time for them to have questions. But imagine if every single board member can just query the company and have a conversation with the company's intelligence in real time. and we can make that 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 reg 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 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 it's roadmapped for customers correct and just kind of drilling down on it can you describe sort of what the organization looked like before and granted you're very early in this but what's it look like

now? Which roles have been eliminated? Uh, what are the new roles? Um, just kind of 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. Um, I mean, just from a, you know, one, one measurement of, of Thank you. how far along we are would be the depth from me to any other individual in the company. And I would say our, our max depth right now is probably five. Okay. Uh, folks between me and anyone in the company. Um, I would want to get that down to two to three, uh, 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 other company. And that feels somewhat, you know, ridiculous when you consider like the old structure, but when you consider that, um, the majority of our work is going through this intelligence layer, um, it's a lot more manageable and it, that goes into the

Jack Dorseyroles, uh, going forward. We, 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 a 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 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 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 and the operators, the ICs.

The second role is the DRI. And that's someone who can own the customer outcomes. They're putting a strategy together. They're understanding what 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. 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 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 ICs and even DRIs report to a player coach. But I think in the future, it's an assignment. It's not a reporting structure, but I'm assigned to ICs or I'm assigned to DRIs to help them master their craft. And obviously the durable human skill there is building human capacity and coaching. And there's a lot of empathy there and all the soft skills that we recognize, great managers are known for. But not making a requirement that they have to be strategic necessarily. They have to build because they need to show off the skill and teach in that way, but they don't necessarily need to be a DRI.

In very rare cases, one person can take on all three of those roles. I think I can take on all three of those roles. My leadership team is expected to take on all three of those roles. They're expected to build as an IC or operate the company. They're expected to be strategic and actually think about 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, with their direct team. Just a little kind of before and after, and you're mid on this, and let's pretend like it's working great and it's two years now and it's extremely flat.

What is the role of the CEO before and after? Most of the listeners, by the way, are CEOs. What does planning look like before and after? What happens to all those people who are directors and managers or the kind of glue people? Like what are kind of the before and afters in your mind? I think my job as CEO in the past I've thought about in three ways. Number one is to ensure that we have the right principles and the right team dynamic. And that's like hiring and firing and setting values and setting the culture and setting the tone. The second is to ensure that decisions are being made in context of our customers and industry trends and competition.

And the third would be to raise the bar on our execution, like to constantly. Increase our capability and to push ourselves into doing things that are uncomfortable so that we're growing all the time. So that's how I thought about my job up until this point. I think in the future, you have those elements, certainly, but I think it's more about the architecture of how the company as an intelligence works. and like if we're building the company as an intelligence our job is as humans and my job is to constantly align it to where we think the right outcome is and i 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 are the humans who are just constantly aligning this towards customer outcomes. But even that changes, I believe, because I think a company's ultimate limiting factor is its own roadmap. And I think 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 and a dashboard we have cash app we have title we have bitkey we have proto these are interfaces these actually touch the real world touch humans and 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

Jack Dorseyyou 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's life. And based on that, we can actually prompt our customers instead of waiting for them to prompt us or having the right question to ask. So we can do the very simple but very valuable thing of like, how do we protect our customers' cash flow? Like we have people using us as a bank account. How do we make sure that they can pay the right and they can pay their Spotify bill and they can pay their kids allowance. And this is all sequenced in a way that allows them to never go to zero, never go negative and have some cushion that allows them to even think about getting to saving or building wealth.

And that just, you know, peace of mind, I think is the most critical aspect here. um 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. 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 the company world model. Our deep understanding of ourselves and also our customers. But I think if I had to say one thing that myself or anyone in the company has to do it's i guess it's this overused phrase of judgment um 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 aligned with the taste that we have and is it unique or is it not and i i guess in for my part i'm the um 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 it i think it it goes down to like are you building a are you building a business that like understand 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 cook.

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, and survive. 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 when these tools really came to bear, like Goose, which is an agent coding harness, was one month before CloudCode in January of 2024.

And CloudCode came out that following month and then like was really put 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 2024 it's 2025 it's only been a year of those tools like one year it just the the compounding nature of this um is pretty incredible so you know being able to like uh 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 uh 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 people are thinking of it as co-pilots 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 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 are jockeying for position. And it's not always clear what is actually true. And I think part of what we're envisioning here is you have a system that's just ground truth and you do away with all the layers. You get back to the kind of productivity that founders often long for. They long for the days when there were 100 people and not 500 people because they were so much more productive.

Why? because you had lots of transparency, limited hierarchy. And so I think the possibility here, as Jack was saying, is instead of just focusing on individual productivity, you reimagine how we work together as humans. And you can do it with a far smaller number of people that are far more productive, yes, but there's a different way of working together where you get the right signals. And it's much more similar to a capitalist system where the signals tell you what to build. It's not somebody who pounds the table harder who gets their product approved, which is, listen, more customers want this than that.

That's how we're going to decide what to build next. So for me, there's something quite magical in that realization. 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 add 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, Rulof. Like, I sort of think 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 optimizing for growth rate, gross profit per employee, net promoter score, probably some combination of those variables.

And the humans at the edges perform an incredibly valuable function of correcting and informing and sort of steering that. And I think one of the phrases that Jack has, which I absolutely love and I've stolen so many times, is companies have multiple founding moments. 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 just don't think, I don't believe in hero worship or the converse of that where you sort of scapegoat people.

I think it's harnessing the best of your team to really advance the company. So I subscribe to the circle idea. 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 want to 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 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 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 want to be as a company, or if they should be going elsewhere to do that.

And I think all these things are going to blur 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 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 yeah um and it was coming from a place of like wow is our company just going to be completely irrelevant the you know 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 moat around and what what do we need to be to Fund and also to grow that. And all that follows from customer expectation. The most amazing thing about OpenClaw to me was that people wanted to take this thing and contain it into a Mac Mini and make it very tangibly theirs and have all this agency around what they did with it.

and we're seeing square sellers do stuff with it like that and interface with the square um apis and we're seeing cash app customers and and these are like not tech people these are just like people i i want to i want a bot to help me manage my life that agency independent of your thoughts on like how good of a system open call 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 um and 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 roadmap like we need to remove that from the equation we need to ensure that our customers are truly building alongside us um and and that they you know are seeing us as a as a series of capabilities that makes their desires fast and easy and um and valuable 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 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 system? Should they start with data? Should they start with the org? Like, how should people go about, you know, running the George Storybook? uh i don't know about this dorsey playbook thing but um but we don't have it all figured out i think there's an important dose of humility that we have that we're endeavoring on this path we believe it's right but we know there's a lot to figure out yeah it's more like if if you were to at 100 people or even you know just starting today if you were to I don't know.

Your company as an AGI, as an intelligence, what would it look like? And what would you need to really differentiate? If I were starting a company today, I would be so excited about how quickly I could build things and how quickly I could prototype and get things out to customers. I would be in this valley of dread about distribution and attention because there is so much noise out there and it's so hard to get to the actual signal of who's building something interesting. that will actually fundamentally change something and will be around for more than a year. It's 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, you know, apps, for instance, and websites and like the traditional retail. there's a number of things that will will change and if you don't have the distribution today it's going to be very hard to fight for that but there'll be new uh 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 um 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 yeah 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 um 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 um going back to like the dri thing when what are you ultimately responsible for and i i think it's helped us a lot um but this is another step like it if if you're starting today or you're 100 today like what what is actually fundamental to solving your your customers' problems and where is the hierarchy getting in the way of that? And look at all the tools you're using. Like, look at all the information you're generating just by doing your work. Just putting that into an intelligence and being able to query it will give you an understanding of the company that is two to three times more than you had before, ever. Because you're relying on people telling you things. And that doesn't always happen for various reasons that Roloff 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 that's the hardest bet is like we can determine causal getting to predictability for these world models around the company and customer is is still right now very much a research bet but like it's it's one that you know 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 ruport's got this good line if you're gonna we'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 um it was something you know december of last year is when the is the when the models really got a uh like noticeable upgrade from being able to be really good at building prototypes and

Reedfield efforts to like understanding like large code bases and legacy code bases like our own. Um, 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, um, it just like every, everyone went home for the holidays and everyone played with these tools and 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 this way? if you had these tools today, like what would the company look like?

And everyone around the table and my team just said 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 cap on our layers to four, me plus four, and all these like small things. um 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 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 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 a 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 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 there was a span of you know expiration to execution and you know under under three weeks um 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

Jack Dorseythe future i didn't want to have to do it with our backs against the wall we're a public company

and there's various challenges there and other companies will will probably get to this realization at some point i don't want to react to that i want to i want to um 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 um and even for the people that we're asking to stay and we're not just reacting into, um, something mediocre, we're, we're, you know, uh, acting towards excellence. And, and like, that's just the tone that we wanted to set. So, um, 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, um, like, what are we not thinking about? What are we not talking about and we you know we kept the group very very tight um and had a conversation with with the board um which was uh my perspective very open to it and and actually more more than open more like yes we agree like we we should we should do this but i'll i'll let roloff speak to that it was a very quick process okay i think part of what helps is that jack had written us a very detailed note laying out the logic it's principled it's not as Jack was saying it's not reactionary it's very well laid out very logical it was clear that the company and the management team was interested in a conversation about how to make this work as opposed to being dogmatic and saying 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 where we started in the first of those three weeks is different from where we ultimately landed by the time the announcement took place.

And I also think it's an example of where we've built enormous trust between the board and the management team. You know, we've been through a lot as a team. And so we have a lot of shorthand to be able to make crucial decisions like this. We gathered several times in quick succession to make sure we drilled in on the key issues. And the board was fully supportive. You too, Rulof, 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 should they start bringing, at 100 employees, should they start bringing in independents?

How do you build an amazing board that really serves the company well, the employees well, the investors well, the customers well? What's your advice on that?

Jack DorseyEarly on, I always told myself and my team that your first board is your investors right um and uh 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. 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 person. um and you know that's why uh roloff um you know we were we were optimizing for for him to be on our board and be an investor but like it was it was a fact that like he would up level our conversation up level our execution more than anything else and challenge us along the way um 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 going to just seem like crazy in the moment which like this one might might be um 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 um because like if we didn't do something like this i just imagine like every year it's a 10 riff or 20 riff 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 um and i you know i had a conversation with the board like 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 and it's just not not inspiring and uh 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 a little off 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. That sometimes that person may come to the conclusion that the founder is no longer the right person to run the company, maybe rightly, maybe wrongly. If you can get an independent board member, there's a different relationship that the founder has with that board member.

And especially if that person has previous experience, it can be a fantastic mentor relationship to help the founder on that journey, depending obviously on their level of experience. I think boards are often built too late in a rush, especially in the run-up to an IPO where people suddenly realize, oh, I've got a four-person board and I need nine, or whatever the case is. and you suddenly assemble people who have no context, they have no history, and they have no chemistry because you will be tested. You're going to have a situation where there's a short seller report or you're dealing with a hostile situation with an activist investor or a tricky financing that really tests the mettle of the team.

And you want to understand the dynamic between the board members and just their willingness to go along and their alignment with the core values of the business. And so I just think it's one of those things that requires a lot more care than I think most people apply to it. Jack, you've started a couple of great companies here. You're kind of a startup 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. Just for the record. Which should not be a goal for anyone, by the way.

That's what I recommend. companies is it ever a good idea not public companies yeah maybe private private i would i would 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-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 also In our businesses are where I decided not to learn something because I embrace all of our mistakes and all the bad decisions we made.

But if I'm not learning from that, actively learning from it, that's what I regret. and um you know in in in probably the worst case in any of these companies um like just delegating way too much yeah 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 just building like a holding company now yeah and like we we got like you know the c over here for square and c over We're 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 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 um that was a mess so i think the the one thing that i i probably consistently

Jack Dorseywould have corrected would be just delegating too much you know too too uh too much of that

and i didn't learn that fast enough like that's that's a regret is i didn't choose to to learn from that fast enough um but when you have your whole your whole your entire company's legible it's a very different equation um 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 um and and that's hence the shift like i can't imagine doing anything bigger than rebuilding our company as an intelligence um or more correct uh given where 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 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 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, I mean, you have this, Brian, like you see a presentation or a Google Doc and we go through it. now um everyone is bringing a prototype that they built 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 um has far more depth and realism than we could ever get from a slide deck and because they can actually modify it in real time like we can have a conversation around like what they're actually building in real time um 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 threat 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 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 past 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 husk bus history what work 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 uh i think it's i think it's having a wider perspective to start and then like because in the past uh if we were to explore different paths like it would be a uh 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 we can do it in an hour

Jack Dorseyyeah and then um so i 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. Yeah. And, and just constantly pushing these, these models to, to doing something that 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 I think the, 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 uh 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're 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 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 um 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 um 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 um our board said absolutely no like you're not getting in the lending business like that's ridiculous and we lost i lost some credibility with with um 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

and we built this thing that allowed effortless peer-to-peer as effortless is just you know sending an email to start and uh our our our coo at the time was on the founding Team of PayPal, Keith Raboy, and even he said no. And he said, like, you know, this is a solved problem. Everyone in the company hated CashUp. It was a team of eight people and hated it for two to three years. 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 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 um so i think it's getting

Jack Dorseycomfortable with like you're going to lose credibility and if you have an understanding of like how to earn that back uh it's okay and 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 you're okay with, yeah, people aren't going to trust me for a bit and it's okay. I'm staking part of my reputation on this and that's 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 a company or when they're hiring someone. And the memo on me was one of my strengths was i was dgaf don't give a flock and one of my weaknesses was i was dgaf i don't give a flock um 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 wavers for me like it it's definitely um i get a lot of hate a lot of pushback a lot of challenges like internally externally um but again it's uh 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 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, 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, um, 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 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 uh it's just an amazing way to approach life and challenges that i find you're a definitely a 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 um what are the benefits you get as a ceo and what do you take from mark and grease in 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 saying that he's not introspective is very introspective i thought that was interesting just to be clear um i don't i didn't get a lot from that but i i do think um the when people think of meditation they think of like this woo woo like you know person in the

desert and uh 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 till 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 sharp Keep in 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 constantly with this mindset of like, this isn't permanent. If I were to stand up, it goes away.

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 like and you're doing 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 want to act with that information so if you think about it as like a woo woo you know 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 and that's that's what i see and that's what you practice.

Maybe I just close on, start with you, Rulaf. There's some timeless qualities of CEOs that last the test of time. And Rulaf, you're involved with YouTube, Instagram, Block, Mongo, Unity. What are timeless CEO qualities and what is new? What are the new qualities CEOs need today? i like acronyms so i came up with one which is um ale ale which is sort of not a very pleasant drink for most people but anyway um authenticity logic and empathy so authenticity i mean are you you know are you pretentious are you who you do people see who you really are do you behave authentically are you logical you're predictable you're rational would you fly off the handle And you're empathetic.

You really care about the team that you manage. You really care about the business. You know, 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, you know. I think it's just hard to keep it in your mind. So for me, those are the three most important, authenticity, logic, and empathy. I think when it comes to dealing with humans, most of those things stay the same. And I remember how many of us thought the world was going to be so different in the midst of COVID. And I listened to a talk that Steven Pinker gave, and he talked about how probably things are going to go back largely the way they were before.

And I think the same is true here. Yes, companies are being built differently. yes AI is absolutely transformational it's going to upend so many industries I think it's the biggest drainer of moats companies have ever seen but some of the basics of dealing with people and leading remain true the one I would say is probably different is the pace of change is so fast and I think kudos again to Jack for the speed with which we're moving on this decision because it would have been easy to dither for six or 12 months in 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 changed what's what's timeless what's changed i value someone who's able to reprogram their mind and assumptions constantly um i mean this is stated a lot but just being able to question your own requirements your own assumptions and your own decisions or how rigid you are uh towards your past the company's past and sacred cows or what the competition is doing um 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 it more valuable because things are moving so fast right now? I think it's more valuable. 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 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 default to.

what these things are suggesting rather than seeing them as an input.

Jack DorseyLike 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.

And 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. 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'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 um the taste thing is real 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 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 and and because it didn't exist is why i'm building it and i think um right now you're seeing a lot of companies they're just copies of copies of copies of copies because it's easy you know 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 great place and thank you both for coming on long strange trip i love the article you wrote i think it's going to be game-changing for lots of companies appreciate you both thank you thank you 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 um 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 this company ptc in the 90s it was very very manager mode uh very hierarchical the power rested in the vps essentially um when i ran hubspot They didn't call it founder mode then, but it was kind of founder mode.

Instead of being a pyramid, it was flat. And a lot of power was rested in the founder's hands. He's sort of proposing the Dorsey mode in my mind. He laughed about it when I said it. But I think of it as like, what's next? And it's more like a circle than a really flat organization. And the power rests kind of in the system. and the system makes a lot of decisions and 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 on to something I'm curious to see what you think comment on Twitter or comment on YouTube I'm curious about your thoughts on it I think Jack would be curious too He's in the very early innings of rolling this out and he's looking for feedback on it. Anyway, appreciate you all. Thanks for tuning in