{"id":"1775221783211-YTVSwOY19Qs","videoId":"YTVSwOY19Qs","url":"https://www.youtube.com/watch?v=YTVSwOY19Qs","title":"Jack Dorsey: Every Company Can Now Be a Mini-AGI","type":"youtube","topicCount":16,"segmentCount":158,"createdAt":"2026-04-03T13:09:43.211Z","uploadDate":"20260402","chunks":[{"title":"Podcast Introduction","summary":"Brian Halligan introduces Jack Dorsey and Roelof Botha. He outlines the podcast's focus on rethinking corporate hierarchy, AI integration, and CEO advice.","entries":[{"text":"Jack Dorsey: 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 even a company going forward? Like, what are these structures going forward? And this is the only, like, durable structure that I could actually imagine lasting for quite some time. And it was coming from a place of like, wow, is our company just going to be completely irrelevant, you know, in the next coming years?","offset":0,"duration":30},{"text":"Brian Halligan: All right, everybody, we had Jack Dorsey on the pod today, founder of Twitter and founder of Block. He's the only founder to have two of his companies end up on the S&P 500. I just learned that today, that's pretty cool. Also, Roelof Botha, who's a Sequoia partner and is on Jack's board at Block.","offset":30,"duration":30},{"text":"Brian Halligan: The conversation was super interesting to me. He recently put an article out that you may have seen, called \"From Hierarchy to Intelligence,\" and it's a manifesto on how to rethink, basically rethink from the first principles how an organization works. How do you completely eliminate hierarchy and how do you put AI right in the center and transform how your company works? And I let him go on that and he was very thoughtful and he spoke a lot about it. Block is really changing the way it's organized.","offset":60,"duration":30},{"text":"Brian Halligan: Before we started, he said, \"I'd love to get some feedback from you and from other people on this.\" So if you've got comments on it, let it rip. He wants some feedback on it. He's in the early innings of a big transformation over there. That was about half of it. The second half of it I just asked him for, like, CEO advice. I work with lots of CEOs, as you folks know. Like, how do you build an amazing board? He's certainly got some scars around board building.","offset":90,"duration":30},{"text":"Brian Halligan: How do you build your second act, like the Cash App versus the original business of Square? Is it a good idea to be a CEO of two different companies at the same time? Being brave and not giving a flock versus going with the flow, and when do you really dig in and when do you kind of go with the flow? And he had some really interesting thoughts on the job of a modern CEO. So tune in, I'll be back at the end and give you some further thoughts.","offset":120,"duration":30}],"startTime":0},{"title":"Replacing Traditional Hierarchy","summary":"Jack discusses the original purpose of hierarchy as an information flow mechanism. He suggests replacing management structures with an AI world model that makes the company's information legible to everyone.","entries":[{"text":"Brian Halligan: But I thought Jack did a really nice job and Roelof did too. Let's get into it. Jack, I read your piece, I think it's fantastic, \"From Hierarchy to Intelligence.\" Before we get into the meat of what it is, can you describe what you think is wrong with the way normal companies' hierarchies work, companies like HubSpot, companies like Block, like what kind of led you to this?","offset":150,"duration":27},{"text":"Jack Dorsey: I don't know if there's one thing that's ultimately wrong. It's just recognizing that like what do we see in the pattern, what is the function of the hierarchy? And what we wanted to explore is just like 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.","offset":177,"duration":33},{"text":"Jack Dorsey: So being able to communicate over a breadth of people and have that be manageable at a human scale. So we've gotten into structures that, you know, we've borrowed and iterated on a little bit over 2,000 years. And now we're faced with 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 company.","offset":210,"duration":30},{"text":"Jack Dorsey: 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, a 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.","offset":240,"duration":40},{"text":"Jack Dorsey: And traditionally we've been reliant upon humans in a management structure in a hierarchy to go up and down a chain to relay that information. Instead, we can take all of those artifacts and put an intelligence on top of it, build a model around it, and actually have a conversation with the company about how the company is doing. And it's not just me as CEO that can do that, but anyone in the company could have that same sort of access to information and same understanding of like what the company can do.","offset":280,"duration":40},{"text":"Jack Dorsey: So you get to a point where you can build these world models for a company, like treat the company as a mini-AGI, for instance, an artificial general intelligence, because it really is. I mean, if you look at a company, it is an intelligence, but it hasn't been structured in a way that's the most efficient or the least lossy in terms of information flow and what people can actually do within the company.","offset":320,"duration":30},{"text":"Jack Dorsey: So the technology is good enough today that we can actually model the company. We can have everyone in the company put in intent, which would be strategy or these artifacts, and we can also have everyone in the company query it as well. And it just really opens the door for what's possible, like Roelof and I have a board meeting every quarter where we construct a bunch of board docs, slides, presentations. We get only so much time for them to have questions.","offset":350,"duration":30},{"text":"Jack Dorsey: But imagine if every single board member can just query the company and have a conversation with the company's intelligence in real time, and we can make that meeting time that we have every quarter really focused on more of the creative or bigger existential decisions and issues than the day-to-day. The same can be said for like our earnings call and analysts, like giving them like fully Reg-FD possible information that is on their timeline with their questioning.","offset":380,"duration":30},{"text":"Jack Dorsey: But you can scale this to any position or any role in the company, which is pretty phenomenal and like we've just never had that ability before. And now we do. And, you know, I think the architecture and the structure of the company is ultimately going to determine its velocity and how well it's roadmapped for customers, correct?","offset":410,"duration":22}],"startTime":150},{"title":"Block's Three-Role Structure","summary":"Jack explains Block's transition to a flatter organization. He details their goal of reducing management layers and standardizing into three roles: individual contributors, directly responsible individuals, and player-coaches.","entries":[{"text":"Brian Halligan: Mm, just kind of drilling down on it, can you describe sort of what the organization looked like before? And granted you're very early in this, but what's it look like now? Which roles have been eliminated? What are the new roles? Just kind of drill down a little bit into what Block looks like today and kind of where it's going.","offset":432,"duration":23},{"text":"Jack Dorsey: Yeah, we are early in it. I mean, just from a, you know, one measurement of how far along we are would be the depth from me to any other individual in the company, and I would say our max depth right now is probably five folks between me and anyone in the company. I would want to get that down to two to three this year.","offset":455,"duration":25},{"text":"Jack Dorsey: And in the most ideal case, you know, there is no layer, everyone in the company reports to me, and that would be, you know, all 6,000 of the company. And that feels somewhat, you know, ridiculous when you consider the old structure. But when you consider that the majority of our work is going through this intelligence layer, it's a lot more manageable.","offset":480,"duration":24},{"text":"Jack Dorsey: And that goes into the roles going forward. We want to normalize down to just three roles. The first is an IC, which is a builder or an operator. This is a salesperson, it's an engineer, it's a designer, product person, 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 10 people to do in the past.","offset":504,"duration":38},{"text":"Jack Dorsey: 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 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.","offset":542,"duration":38},{"text":"Jack Dorsey: 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.","offset":580,"duration":25},{"text":"Jack Dorsey: 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, 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.","offset":605,"duration":30},{"text":"Jack Dorsey: 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, you know, all the soft skills that we recognize great managers are known for.","offset":635,"duration":30},{"text":"Jack Dorsey: But not making it a requirement that they have to be strategic necessarily. They have to build, because they need to show off the skill and teach in that way, but they don't necessarily need to be a DRI. Now, I think 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 or with their direct team.","offset":665,"duration":36}],"startTime":432},{"title":"The Evolving Role of the CEO","summary":"Jack describes how the CEO's job shifts from traditional management to architectural alignment. He explains how customer interactions will proactively define the company's roadmap based on its core capabilities.","entries":[{"text":"Brian Halligan: Just a little kind of before and after, and you're mid on this, let's pretend like it's working great and it's years from now and it's extremely flat. Like what does the role of the CEO before and after? How's that changed? Most of the listeners, by the way, are CEOs. What does, like, planning look like before and after? What happens to all those people who are directors and managers or the glue people? Like what are sort of the before and afters in your mind?","offset":701,"duration":30},{"text":"Jack Dorsey: I think my job as CEO in the past I've thought about in three ways. Number one is to ensure that we have the right principles and the right team dynamic. And that's like hiring and firing and setting values and setting the culture and setting the tone. The second is to ensure that decisions are being made in context of our customers and industry trends and competition. And the third would be to raise the bar on our execution, like to constantly increase our capability and to push ourselves into doing things that are uncomfortable so that we're growing all the time.","offset":731,"duration":34},{"text":"Jack Dorsey: 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 like the architecture of how the company as an intelligence works. And if we're building the company as an intelligence, our job as humans and my job as CEO is to constantly align it to where we think the right outcome is.","offset":765,"duration":28},{"text":"Jack Dorsey: And I see, like, visually I see 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.","offset":793,"duration":27},{"text":"Jack Dorsey: 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 layers of like, okay, so what do we actually build? We build up capabilities, which are effectively our tools.","offset":820,"duration":22},{"text":"Jack Dorsey: 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 TIDAL, we have Bitkey, we have Proto, these are interfaces, these actually touch the real world, touch humans, and we can deliver our capabilities in these interfaces.","offset":842,"duration":24},{"text":"Jack Dorsey: 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'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 something that really tells the truth about your life or your business's life.","offset":866,"duration":22},{"text":"Jack Dorsey: 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 customer's cash flow? Like we have people using us as a bank account. How do we make sure that they can pay their rent and they can pay their Spotify bill and they can pay their kid's allowance?","offset":888,"duration":27},{"text":"Jack Dorsey: And this is all sequenced in a way that allows them to never go to zero, never go negative, and have some cushion that allows them to even think about getting to saving or building wealth. And that's just, 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 have this feature?\" We should just be able to build that and compose it in real time based on our capabilities.","offset":915,"duration":37},{"text":"Jack Dorsey: 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.","offset":952,"duration":23},{"text":"Jack Dorsey: But I think like 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. But it is judgment against like what we intend to build in the world and is it on, is it aligned with that judgment, is it aligned with the values, is it aligned with the taste that we have and is it unique or is it not?","offset":975,"duration":29},{"text":"Jack Dorsey: And I guess for my part I'm the extra checkpoint on like is the alignment circle of humans, that edge of humans actually working correctly.","offset":1004,"duration":9}],"startTime":701},{"title":"Rebuilding Around Ground Truth","summary":"Jack and Roelof discuss whether this AI-centric model applies to all businesses. They argue that organizations built around ground truth and transparent signals will outperform command-and-control structures.","entries":[{"text":"Brian Halligan: And I see how this works exceptionally well for Block, you have a lot of signal. How does this work for, I don't know, Sierra, Workday, somebody who doesn't have the quality signal, the frequency of signal? Does it apply or doesn't work as well?","offset":1013,"duration":8},{"text":"Jack Dorsey: I think it probably does. I think it goes down to like 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. 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.","offset":1021,"duration":33},{"text":"Jack Dorsey: 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 very, very challenging to differentiate and survive.","offset":1054,"duration":28},{"text":"Jack Dorsey: 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 Claude Code in January of 2024. And Claude Code came out that following month and then like was really put into out of beta in May of that year.","offset":1082,"duration":29},{"text":"Jack Dorsey: And, you know, that whole year I just spent every single day for 3 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, I'm sorry, it wasn't 2024, it's 2025.","offset":1111,"duration":23},{"text":"Jack Dorsey: It's only been a year of those tools, like one year, it's just the compounding nature of this is pretty incredible. So 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. They're just living in this abstraction of 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.","offset":1134,"duration":36},{"text":"Brian Halligan: I think you're right. I think if people are thinking of it as copilots and individual productivity versus your, I think your idea is complete business transformation and I think it's super interesting and compelling.","offset":1170,"duration":10},{"text":"Roelof Botha: Can I add one thought I've had as I've listened to this 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 lead to optimal outcomes, but you just need to have the right framework and the right system.","offset":1180,"duration":17},{"text":"Roelof Botha: I think the way that many companies work today is a little bit more command and control. Very much so. And you have hierarchies and you have political actions and people, you know, are jockeying for position and it's 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.","offset":1197,"duration":21},{"text":"Roelof Botha: And you do away with all the layers, you get back to the kind of productivity that founders often long for. They long for the days when they were 100 people and not 500 people because they were so much more productive. Why? Because you had, you know, 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.","offset":1218,"duration":31},{"text":"Roelof Botha: And you can do it with 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 it's much more similar to a capitalist system where the signals tell you what to build. It's not somebody who pounds the table harder who gets their product approved, it's just listen, more customers want this than that, that's how we're going to decide what to build next. For me there's something quite magical in that realization.","offset":1249,"duration":25},{"text":"Brian Halligan: 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 here.","offset":1274,"duration":21}],"startTime":1013},{"title":"Dorsey Mode and Decision Making","summary":"Brian pitches the idea of \"Dorsey Mode\" where AI makes decisions. Jack clarifies that AI simply facilitates context-rich choices, while customer behaviors and human judgment actually drive the company's direction.","entries":[{"text":"Brian Halligan: I have a theory I want to run by you Roelof, 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 the 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?","offset":1295,"duration":26},{"text":"Roelof Botha: Oh, I don't think the AI makes most of the decisions. I think and Jack should correct me here, I think the AI helps with communicating the alignment and the management team or the inner core helps set the framework. What is the objective function? Are we optimizing for growth rate, gross profit per employee, net promoter score, probably some combination of those variables?","offset":1321,"duration":23},{"text":"Roelof Botha: 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 the product, introduce something new.","offset":1344,"duration":26},{"text":"Roelof Botha: 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 hero worship or the converse of that where you sort of scapegoat people. I think it's harnessing the best of of your team to really advance the company. So I subscribe to the circle idea.","offset":1370,"duration":11},{"text":"Jack Dorsey: Yeah, I also don't think the AI is making the majority of the decisions. I think it's facilitating a more context-rich decision. I think ultimately, like in the most ideal case, our customers are actually making the majority of the decisions because they're just based on their queries and what they're trying to do with the system delineates like where our roadmap should go.","offset":1381,"duration":24},{"text":"Jack Dorsey: 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, product feedback on Twitter, all these other things.","offset":1405,"duration":29},{"text":"Jack Dorsey: 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 to do that.","offset":1434,"duration":25},{"text":"Jack Dorsey: 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 in the same hour, in the same thought process of like what is even a company going forward? 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.","offset":1459,"duration":29},{"text":"Jack Dorsey: And it was coming from a place of like wow, is our company just going to be completely irrelevant in the next coming years or even 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 and also to grow that? And like what are the and all that follows from customer expectation?","offset":1488,"duration":27},{"text":"Jack Dorsey: Like the most amazing thing about open-Claude 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 in interface with the Square APIs, and we're seeing Cash App customers, and these are not tech people, these are just like people, \"I want I want a bot to help me manage my life.\"","offset":1515,"duration":-1166},{"text":"Jack Dorsey: That agency, independent of your thoughts on like how good of a system open-Claude is right now, it'll get better and better, but the intent behind that is agency. I want to tangibly control this intelligence and for it to better me and what it makes possible for me is incredible. And that expectation floor has just risen dramatically.","offset":349,"duration":1226},{"text":"Jack Dorsey: And that leads me again to like yeah, 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 and that they, you know, are seeing us as a series of capabilities that makes their desires fast and easy and and valuable.","offset":1575,"duration":25},{"text":"Jack Dorsey: So like it really goes back to the capability set that we have and then 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.","offset":1600,"duration":15}],"startTime":1295},{"title":"Applying the Intelligence Model","summary":"Jack advises startups to structure their companies as an intelligence from day one. He emphasizes the importance of making workflows entirely legible and eliminating unnecessary titles to maintain focus.","entries":[{"text":"Brian Halligan: I spent this morning at a company called Rogo here in New York City. They read your article. Let's say you're advising the CEO of 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 org? Like how should people go about, you know, running the Dorsey playbook?","offset":1615,"duration":23},{"text":"Roelof Botha: Uh, 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 we know there's a lot to figure out.","offset":1638,"duration":12},{"text":"Jack Dorsey: Yeah, it's more like if if you were at 100 people or even, you know, just starting today, if you were to build your company as an AGI, as an intelligence, what would it look like? And what would you need to really differentiate? Like if I were starting a company today, I would be so excited about how quickly I could build things and how quickly I could prototype and get things out to customers.","offset":1650,"duration":23},{"text":"Jack Dorsey: 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. It just like I think distribution really becomes a differentiator.","offset":1673,"duration":27},{"text":"Jack Dorsey: And I think there's some event horizon where the way we think about distribution today closes off. You know, it like there's there's 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 going to be very hard to fight for that.","offset":1700,"duration":24},{"text":"Jack Dorsey: 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 do I need a hierarchy?","offset":1724,"duration":21},{"text":"Jack Dorsey: Brian, a year into Square, I also 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. So we ripped up all the business cards, we normalized down to a title of like you're lead of what, and the longer that is behind lead is probably the farther down you are in the organization.","offset":1745,"duration":29},{"text":"Jack Dorsey: And we've kept it, like we we you know we don't have titles. We have like, you know, what do you lead, going back to like the DRI thing, what are you ultimately responsible for? And I think it's helped us a lot. But this is another step. Like if if you're starting today or you're 100 today, like what what is actually fundamental to solving your customer's problems and and where is the hierarchy getting in the way of that?","offset":1774,"duration":26},{"text":"Jack Dorsey: And look at all the tools you're using. Like look at all the information you're generating just by doing your work. Like just putting that into an intelligence and being able to query it will give you an understanding of the company that like is two to three times more than you had before, ever. Because you're relying upon people telling you things.","offset":1800,"duration":20},{"text":"Jack Dorsey: And, you know, that doesn't always happen for various reasons that, you know, Roelof spoke to in terms of agenda or politics or emotions or empathy, all all these things. Imagine if your company was entirely legible. Like entirely legible every aspect of it. And we're not far off from that from a data perspective. It's putting the intelligence on top of it and making it useful and then making it proactive.","offset":1820,"duration":28},{"text":"Jack Dorsey: 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 customers is still right now very much a research bet. But like it's imminently solvable.","offset":1848,"duration":17}],"startTime":1615},{"title":"Logic Behind Block's Restructuring","summary":"Jack and Roelof share the behind-the-scenes process of Block's 40% reduction in force. They explain how rapid advancements in AI coding tools prompted them to proactively redesign the company's scale.","entries":[{"text":"Brian Halligan: Mm. 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 should it be, how bold should it be? You know, Ruth Porat's got this good line, if you're going to eat a shit sandwich, don't nibble. And you seem like you took a big bite. What was that debate behind the scenes and then Roelof, like how did he pitch it to you guys and what was the board's reaction? Just like behind the scenes on that.","offset":1865,"duration":35},{"text":"Jack Dorsey: Yeah. So December of last year is when the model is really got a noticeable upgrade from being able to be really good at building prototypes and greenfield efforts to like understanding like large codebases and legacy codebases 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 became suddenly very mature. Like just in that month.","offset":1900,"duration":35},{"text":"Jack Dorsey: And it just like 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 this way if you had these tools today? Like what would the company look like?\"","offset":1935,"duration":23},{"text":"Jack Dorsey: 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 a cap on our layers to four, me plus four, and all these like small things.","offset":1958,"duration":26},{"text":"Jack Dorsey: 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. And then we just did this exercise of like okay, so what is the minimum number of people that we would need to keep the service up 100%? And then next, what is the minimum 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.","offset":1984,"duration":34},{"text":"Jack Dorsey: And then third, what is the minimum set of folks that we need in order to grow, to fulfill our commitments we've made to the street, but also rebuild the company as an intelligence. And that's roughly the number that we got to and we built in some buffer in case we made mistakes, which we did. And you know, hard hard not to, especially operating the way we have.","offset":2018,"duration":25},{"text":"Jack Dorsey: 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 that and and there was a span of exploration to execution and, you know, under under three weeks.","offset":2043,"duration":22},{"text":"Jack Dorsey: And I think generally I wanted to make sure that we if we knew that this was what our company was going to be in the future, I didn't want to have to do it with our backs against the wall. We're a public company and there's various challenges there, and other companies will will probably get to this realization at some point.","offset":2065,"duration":24},{"text":"Jack Dorsey: I don't want to react to that. 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 part, to leave, and even for the people that we're asking to stay and we're not just reacting into something mediocre, we're acting towards excellence. And like that's just the tone that we wanted to set.","offset":2089,"duration":28},{"text":"Jack Dorsey: So, you know, every day was just like constantly checking like are we doing the right thing, is this the right set of folks, like what are we not thinking about, what are we not talking about? And we you know we kept the the group very, very tight and had a conversation with with a board, which was a my perspective very open to it and actually more than open, more like, \"Yes, we agree, like we should we should do this.\" But I'll let Roelof speak to that.","offset":2117,"duration":37},{"text":"Roelof Botha: It was a very quick process. I think part of what helps is that Jack had written us a very detailed note laying out the logic. It's principled. It's not reactive as Jack was saying, it's not reactionary, it's very well laid out, very logical.","offset":2154,"duration":17},{"text":"Roelof Botha: 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 they 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 is different from where we ultimately landed by the time the announcement took place.","offset":2171,"duration":27},{"text":"Roelof Botha: And I also think it's just 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.","offset":2198,"duration":20}],"startTime":1865},{"title":"How to Build an Effective Board","summary":"Jack and Roelof share advice on selecting board members. They recommend treating early investors as hires you can't fire and adding independent directors who will elevate execution and handle crises.","entries":[{"text":"Brian Halligan: You two, Roelof you've been on a lot of boards, Jack you've had your ups and downs with different boards. Any advice for these CEOs listening that should they start at 100 employees, should they start bringing in independents, should they 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?","offset":2218,"duration":21},{"text":"Jack Dorsey: I mean early on I always told myself and my team that like your your first board is your investors, right? And I would treat that relationship as a hire you can never fire, and in fact they can fire you, and I've been on the other side of that. So it really puts pressure on finding the right person that you'd actually want to work with at the company knowing that you could never fire them.","offset":2239,"duration":31},{"text":"Jack Dorsey: 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 Roelof, you know, we we we were optimizing for him to be on our board and be an investor.","offset":2270,"duration":23},{"text":"Jack Dorsey: But like 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 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?","offset":2293,"duration":33},{"text":"Jack Dorsey: And I think you have to build a board that has different perspective on that and that is open to wild ideas, 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 like really document it and paint a picture of like where this could go and like what the opportunity cost is if we don't do something.","offset":2326,"duration":27},{"text":"Jack Dorsey: Because if we didn't do something like this, I just imagine like every year it's a 10% RIF or 20% RIF 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.","offset":2353,"duration":18},{"text":"Jack Dorsey: And I, you know, had a conversation with a board about 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 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.","offset":2371,"duration":17},{"text":"Roelof Botha: Well 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 it'll have a much bigger bearing on the ultimate outcome of your company.","offset":2388,"duration":23},{"text":"Roelof Botha: 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, you know, described that sometimes, you know, that person may come to the conclusion that the founder's no longer the right person to run the company, maybe rightly, maybe wrongly.","offset":2411,"duration":24},{"text":"Roelof Botha: 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.","offset":2435,"duration":18},{"text":"Roelof Botha: I think boards are often built too late in a rush, especially in the run up up to an IPO where people suddenly realize, \"Ooh, I've got a four-person board and I need nine,\" whatever the case is, and then you suddenly assemble people who have no context, they have no history, and they have no chemistry, because you will be tested.","offset":2453,"duration":19},{"text":"Roelof Botha: You're going to have a situation where there's a short-seller report or you're dealing with a hostile, you know, situation with activist investor or a tricky financing, you know, 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.","offset":2472,"duration":21}],"startTime":2218},{"title":"CEO Mistakes and Over-Delegation","summary":"Jack reflects on his biggest career mistakes, noting that leading two public companies is an anti-goal. He regrets over-delegating within Block and creating misaligned cultures instead of a unified ecosystem.","entries":[{"text":"Brian Halligan: Jack, you've started a couple great companies here, you're a startup founder, scale-up CEO. Roelof, he was the only person to have founded two companies that made it into the S&P 500. That's amazing. And the only person to have been simultaneously CEO of two public companies, for the record.","offset":2493,"duration":23},{"text":"Jack Dorsey: Which should not be should not be a goal for anyone, by the way.","offset":2516,"duration":2},{"text":"Brian Halligan: Let me ask him, he's CEO of two companies. Is it ever a good idea?","offset":2518,"duration":3},{"text":"Jack Dorsey: Not public companies. Private maybe. Private 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 definitely like an anti-goal, it's an anti-pattern.","offset":2521,"duration":15},{"text":"Brian Halligan: 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 growing really fast? Like yeah, what do you got?","offset":2536,"duration":15},{"text":"Jack Dorsey: My only regrets in life and and also in our in our businesses, um, are where I decided not to learn something. Because I 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, like that's that's what I regret.","offset":2551,"duration":29},{"text":"Jack Dorsey: And, you know, in in probably the worst case in any of these companies, just delegating way too much. 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.\"","offset":2580,"duration":24},{"text":"Jack Dorsey: And like we got like you know the CEO over here for Square and CEO over here for Cash App and like the value of our company is not like these, you know, unrelated things that are growing at different clips, it's how do we bring them together and like really, you know, um, challenge the whole financial network entirely, because we have we have both sides of the counter.","offset":2604,"duration":22},{"text":"Jack Dorsey: 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 one thing that I probably consistently would have corrected would be just delegating too much. You know, too too much of that and I didn't learn that fast enough. Like that's that's the regret, is I didn't choose to to learn from that fast enough.","offset":2626,"duration":31},{"text":"Jack Dorsey: But when you have your whole your entire company is 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?","offset":2657,"duration":29},{"text":"Jack Dorsey: And and that's hence the shift. Like I I can't imagine doing anything bigger than rebuilding our company as an intelligence um, or more correct um given where where everything is trending. So it just feels like I have to constantly build um and constantly learn from whatever we're putting out there in order for us to stay relevant going forward.","offset":2686,"duration":21}],"startTime":2493},{"title":"How AI Transformed Internal Meetings","summary":"Roelof and Jack discuss how internal meetings have drastically changed. Instead of presenting slide decks, teams now bring interactive, real-time prototypes to test ideas with near-zero cost of failure.","entries":[{"text":"Roelof Botha: 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?","offset":2707,"duration":14},{"text":"Jack Dorsey: Well I mean just two months ago, every meeting that we would have would come you mean you you you have this Brian, 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 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.","offset":2721,"duration":37},{"text":"Jack Dorsey: 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 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 what is the right path?","offset":2758,"duration":33},{"text":"Jack Dorsey: 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.","offset":2791,"duration":13},{"text":"Brian Halligan: I I completely agree with you, like a lot of times in HubSpot's history what worked was when we were doing a lot of different stuff and we were distracted, 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. Do you have a reaction to that?","offset":2804,"duration":20},{"text":"Jack Dorsey: Yeah it's uh I think it's I think it's having a wider perspective to start and then because in the past 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.","offset":2824,"duration":22},{"text":"Jack Dorsey: But today we can do it in an hour. And then um 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 um and just constantly pushing these these models to to doing something that they weren't they weren't we didn't think they were capable of.","offset":2846,"duration":35},{"text":"Jack Dorsey: And that's where I think the magic still happens and where where I think the focus still comes to bear um because at the end of the day 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 and the world model, then you know it just changes everything. So I don't even know if the question matters anymore.","offset":2881,"duration":20}],"startTime":2707},{"title":"Second Acts and Risking Credibility","summary":"Jack shares the story of creating Cash App against the board's initial resistance. He emphasizes that leaders must be willing to lose credibility in the short term to build a successful new venture.","entries":[{"text":"Brian Halligan: 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 BlueSky, interesting stuff with Spiral. Advice to CEOs trying to figure that second act out?","offset":2901,"duration":14},{"text":"Jack Dorsey: Uh, I don't know if I ever considered to be like a second act, it's just something that like we had I wanted to do and I had to do and it was interesting.","offset":2915,"duration":7},{"text":"Brian Halligan: How's building something new distracting to the org and like how do you resource it?","offset":2922,"duration":4},{"text":"Roelof Botha: Well Cash App was like that in early days.","offset":2926,"duration":1},{"text":"Jack Dorsey: 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 we we had multiple moments and these are the founding moments that um I think are critical for a company.","offset":2927,"duration":23},{"text":"Jack Dorsey: But like we were we started with a card reader, eventually we determined that \"Hey we should probably lend money to sellers\" because like no seller wants to accept credit cards, what they want is to get more sales. And what helps them get more sales? More capital to deploy into their business.","offset":2950,"duration":18},{"text":"Jack Dorsey: When we first brought it to our board, um our board said absolutely no. Like you're not getting into the lending business, like it's ridiculous. And we lost I lost some credibility with with the board and our population because we wanted to do this and we kept pushing it and pushing it and eventually they said yes.","offset":2968,"duration":19},{"text":"Jack Dorsey: Cash App was the same thing where we were about merchants, our mission was make commerce easy, and we built this thing that allowed effortless peer-to-peer, as effortless as just you know sending an email to start. And uh our our COO at the time was on the founding team of PayPal or uh Keith Rabois. And even he said no, and he said like you know this is a solved problem.","offset":2987,"duration":24},{"text":"Jack Dorsey: Everyone in the company hated Cash App, it was a team of eight people. And uh hated it for two to three years, we mentioned it less than eight times in our S-1 to go public. Um our investors didn't understand it at all. And every day that I allowed it to persist and defended it, I lost credibility.","offset":3011,"duration":22},{"text":"Jack Dorsey: 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 comfortable 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 and you're okay with yeah people aren't going to trust me for a bit and it's okay. Um I'm I'm staking part of my reputation on this and this I believe it. I think it makes all those answers stronger, by the way.","offset":3033,"duration":38}],"startTime":2901},{"title":"Treating Every Encounter as a Mentor","summary":"Jack discusses his approach to personal growth and feedback. Rather than relying on a single mentor, he chooses to treat every encounter and problem as an opportunity to actively learn something new.","entries":[{"text":"Brian Halligan: I have a weird story for you, when Sequoia was hiring me they write a memo when they're investing in a company or when they're hiring someone and the memo on me was one of my strengths was I was DGAF, don't give a flock, and one of my weaknesses was I was DGAF, I don't give a flock. You strike me as someone who's has high DGAF and you stick with your convictions for a very long periods of time. Founders struggle with that. I struggle with that. Advice?","offset":3071,"duration":30},{"text":"Jack Dorsey: Yeah I would say it wavers for me. Like it 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 made a I made a decision some time ago when I first became CEO of Twitter, everyone was telling me I needed a uh CEO coach.","offset":3101,"duration":19},{"text":"Brian Halligan: Hmm.","offset":3120,"duration":1},{"text":"Jack Dorsey: And I got the CEO coach and he was a great guy but like I was learning absolutely nothing. And it it just reminded me of all these times when you put so much emphasis on like who's my mentor, who am I learning from, who's my mentor, who am I learning from? And around that time I just decided I'm 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.","offset":3121,"duration":30},{"text":"Jack Dorsey: And to for it to be a mentor I have to decide that I'm going to learn something from it. Like 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?","offset":3151,"duration":20},{"text":"Jack Dorsey: 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 what not. 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?","offset":3171,"duration":20},{"text":"Jack Dorsey: 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? Um and uh you know sometimes I I get to the right answer, sometimes I don't, and I just like continue in my ways and it's a failure. But I just having that mindset instead of having this one mentor in your life now you have infinite mentors. Like you know it's it's just an amazing way to approach life and challenges that that I found.","offset":3191,"duration":29}],"startTime":3071},{"title":"The Purpose of Meditation","summary":"Jack explains his physical practice of Vipassana meditation. He details how sitting with pain and focusing on the breath trains the mind to observe without reacting emotionally to impermanent situations.","entries":[{"text":"Brian Halligan: You're definitely a learner, talked a lot about it on other, I've seen you talk about it a lot. You're a meditator. Should all CEOs meditate? What are the benefits you get as the CEO? And what do you take from Marc Andreessen talking about how he's very he's not introspective? I thought that was an interesting comment. Like talk about in meditation, CEOs, what do you get from it? Yeah.","offset":3220,"duration":26},{"text":"Jack Dorsey: Him saying that he's not introspective is very introspective of him, just to be clear. Um I didn't get a lot from that. But 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 have 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.","offset":3246,"duration":27},{"text":"Jack Dorsey: But if you actually get into like true meditation, it's a very physical thing. Like it's a very physical um practice and what you're doing is you're training your mind to focus on one point. One point. Like the the meditation retreats I did were 10 days and you spend the first 3 days sitting from 4:30 in the morning till 9:00 p.m. focusing on the feeling of your breath on your upper lip. Yep.","offset":3273,"duration":24},{"text":"Jack Dorsey: Just that and just the sensation of it. And what you're training your mind to do is to sharpen your focus and then just to observe. Observe the sensation without reacting to it from an emotional or intellectual standpoint. 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.","offset":3297,"duration":33},{"text":"Jack Dorsey: If I were to stand up, it goes away. Hmm. 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 in 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.","offset":3330,"duration":24},{"text":"Jack Dorsey: 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.","offset":3354,"duration":28}],"startTime":3220},{"title":"Essential CEO Qualities","summary":"Roelof shares his ALE framework (Authenticity, Logic, Empathy) for leadership. Jack adds that the modern era requires leaders who can constantly reprogram their assumptions and use AI as input to create unique output.","entries":[{"text":"Brian Halligan: Maybe just close on, start with you Roelof. There's some timeless qualities of CEOs um that last the test the time. And Roelof you you you're involved with YouTube, Instagram, Block, Mongo, Unity. What are timeless CEO qualities and what is new? Like what are the new qualities CEOs need today?","offset":3382,"duration":30},{"text":"Roelof Botha: I like acronyms, so I came up with one which is 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? Are you predictable? Are you rational? Or do you fly off the handle?","offset":3412,"duration":29},{"text":"Roelof Botha: And are you empathetic? Do you really care about the team that you manage? Do you really care about the business? Um you know, sort of 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 just hard to keep it in your mind.","offset":3441,"duration":12},{"text":"Roelof Botha: 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.","offset":3453,"duration":23},{"text":"Roelof Botha: And I think the same is true here. Yes companies are being built differently, yes AI's 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 you know basics of dealing with people and leading remain true.","offset":3476,"duration":18},{"text":"Roelof Botha: The one I would say is probably different is the pace of of change is so fast. And I think, you know, kudos again to Jack for the the speed with which we're moving on this decision because it would have been easy to dither for 6 or 12 months on this decision. So you've got to move fast.","offset":3494,"duration":19},{"text":"Brian Halligan: Mm. 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 things. What do you think? And what's what's what's timeless, what's changed?","offset":3513,"duration":10},{"text":"Jack Dorsey: 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, um or how rigid you are uh towards your past, the company's past and its sacred cows or what the competition is doing.","offset":3523,"duration":29},{"text":"Jack Dorsey: Um it's just 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.","offset":3552,"duration":14},{"text":"Brian Halligan: Has it always been valuable or is it more valuable because things are moving so fast right now?","offset":3566,"duration":4},{"text":"Jack Dorsey: I think it's more valuable. Like being able to, 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 what the tools do and like this is the way we do things and I think people will um because we're offloading some of our intelligence to intelligences, and people will go along with um more likely to to default to what these things are suggesting rather than seeing them as an input.","offset":3570,"duration":33},{"text":"Jack Dorsey: Like I I think we're still in the mode where most people are seeing all what the intelligences do, these tools do as output rather than better input to create better output ourselves. Um and I like I think that's important to me like when I was doing that like everyday 3 hours, like this is input to me and it's now up to me to like really um 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.","offset":3603,"duration":31},{"text":"Jack Dorsey: So having someone who's able to discern signal from noise and cool from not, relevant, you know, like there is, you know, this is highly overused right now, um the the taste thing is real and 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?","offset":3634,"duration":29},{"text":"Jack Dorsey: 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 that are just copies of copies of copies of copies because it's easy instead of like what's your what's your point of view? Like what what is opinionated in this and like where where is it pushing the the boundaries and where is it uncomfortable?","offset":3663,"duration":34}],"startTime":3382},{"title":"Podcast Outro","summary":"Brian thanks his guests and concludes the episode. He reflects on the evolution from Manager Mode to Founder Mode, and potentially to \"Dorsey Mode,\" asking the audience for their thoughts.","entries":[{"text":"Brian Halligan: Mm. I think that's brilliant. It's a great place to end. Thank you both for coming on Long Strange Trip. I love the article you wrote, I think it's going to be game-changer for lots of companies. Appreciate you both.","offset":3697,"duration":9},{"text":"Jack Dorsey/Roelof Botha: Thank you. Thank you. Thank you, Brian. Thank you, Jack. Thank you.","offset":3706,"duration":4},{"text":"Brian Halligan: Hope you liked 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.","offset":3710,"duration":28},{"text":"Brian Halligan: And I sort of think of it as like when I grew up in my career, I worked at this company PTC in the 90s. It was very, very Manager Mode, uh very hierarchical, uh the power rested in the VPs essentially. Uh when I ran HubSpot, they didn't call it Founder Mode then but it was kind of Founder Mode. Instead of being a pyramid, it was flat and a lot of power was rested in the in the founder's hands.","offset":3738,"duration":25},{"text":"Brian Halligan: Um he sort of proposing the Dorsey Mode in my mind. He laughed about it when I said it, but I think of it as like what's next? And it's more like a circle than a really flat organization and the power rests in the kind of in the system and the system makes a lot of decisions and can react real time to the employees and the customers.","offset":3763,"duration":24},{"text":"Brian Halligan: But I think of Dorsey Mode as getting rid of the hierarchy all together, building basically the brain, getting the inputs right, and having it make a lot of the decisions that a hierarchy used to. I think he's onto something, I'm curious to see what you think. Um comment on Twitter, comment on on YouTube. I'm I'm curious about your thoughts on it. I think Jack would be curious too. He's in the very early innings of rolling this out and he's looking for feedback on it. Anyway, appreciate you all. Thanks for tuning in.","offset":3787,"duration":15}],"startTime":3697}],"entries":[{"text":"Jack Dorsey: 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 even a company going forward? Like, what are these structures going forward? And this is the only, like, durable structure that I could actually imagine lasting for quite some time. And it was coming from a place of like, wow, is our company just going to be completely irrelevant, you know, in the next coming years?","offset":0,"duration":30},{"text":"Brian Halligan: All right, everybody, we had Jack Dorsey on the pod today, founder of Twitter and founder of Block. He's the only founder to have two of his companies end up on the S&P 500. I just learned that today, that's pretty cool. Also, Roelof Botha, who's a Sequoia partner and is on Jack's board at Block.","offset":30,"duration":30},{"text":"Brian Halligan: The conversation was super interesting to me. He recently put an article out that you may have seen, called \"From Hierarchy to Intelligence,\" and it's a manifesto on how to rethink, basically rethink from the first principles how an organization works. How do you completely eliminate hierarchy and how do you put AI right in the center and transform how your company works? And I let him go on that and he was very thoughtful and he spoke a lot about it. Block is really changing the way it's organized.","offset":60,"duration":30},{"text":"Brian Halligan: Before we started, he said, \"I'd love to get some feedback from you and from other people on this.\" So if you've got comments on it, let it rip. He wants some feedback on it. He's in the early innings of a big transformation over there. That was about half of it. The second half of it I just asked him for, like, CEO advice. I work with lots of CEOs, as you folks know. Like, how do you build an amazing board? He's certainly got some scars around board building.","offset":90,"duration":30},{"text":"Brian Halligan: How do you build your second act, like the Cash App versus the original business of Square? Is it a good idea to be a CEO of two different companies at the same time? Being brave and not giving a flock versus going with the flow, and when do you really dig in and when do you kind of go with the flow? And he had some really interesting thoughts on the job of a modern CEO. So tune in, I'll be back at the end and give you some further thoughts.","offset":120,"duration":30},{"text":"Brian Halligan: But I thought Jack did a really nice job and Roelof did too. Let's get into it. Jack, I read your piece, I think it's fantastic, \"From Hierarchy to Intelligence.\" Before we get into the meat of what it is, can you describe what you think is wrong with the way normal companies' hierarchies work, companies like HubSpot, companies like Block, like what kind of led you to this?","offset":150,"duration":27},{"text":"Jack Dorsey: I don't know if there's one thing that's ultimately wrong. It's just recognizing that like what do we see in the pattern, what is the function of the hierarchy? And what we wanted to explore is just like 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.","offset":177,"duration":33},{"text":"Jack Dorsey: So being able to communicate over a breadth of people and have that be manageable at a human scale. So we've gotten into structures that, you know, we've borrowed and iterated on a little bit over 2,000 years. And now we're faced with 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 company.","offset":210,"duration":30},{"text":"Jack Dorsey: 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, a 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.","offset":240,"duration":40},{"text":"Jack Dorsey: And traditionally we've been reliant upon humans in a management structure in a hierarchy to go up and down a chain to relay that information. Instead, we can take all of those artifacts and put an intelligence on top of it, build a model around it, and actually have a conversation with the company about how the company is doing. And it's not just me as CEO that can do that, but anyone in the company could have that same sort of access to information and same understanding of like what the company can do.","offset":280,"duration":40},{"text":"Jack Dorsey: So you get to a point where you can build these world models for a company, like treat the company as a mini-AGI, for instance, an artificial general intelligence, because it really is. I mean, if you look at a company, it is an intelligence, but it hasn't been structured in a way that's the most efficient or the least lossy in terms of information flow and what people can actually do within the company.","offset":320,"duration":30},{"text":"Jack Dorsey: So the technology is good enough today that we can actually model the company. We can have everyone in the company put in intent, which would be strategy or these artifacts, and we can also have everyone in the company query it as well. And it just really opens the door for what's possible, like Roelof and I have a board meeting every quarter where we construct a bunch of board docs, slides, presentations. We get only so much time for them to have questions.","offset":350,"duration":30},{"text":"Jack Dorsey: But imagine if every single board member can just query the company and have a conversation with the company's intelligence in real time, and we can make that meeting time that we have every quarter really focused on more of the creative or bigger existential decisions and issues than the day-to-day. The same can be said for like our earnings call and analysts, like giving them like fully Reg-FD possible information that is on their timeline with their questioning.","offset":380,"duration":30},{"text":"Jack Dorsey: But you can scale this to any position or any role in the company, which is pretty phenomenal and like we've just never had that ability before. And now we do. And, you know, I think the architecture and the structure of the company is ultimately going to determine its velocity and how well it's roadmapped for customers, correct?","offset":410,"duration":22},{"text":"Brian Halligan: Mm, just kind of drilling down on it, can you describe sort of what the organization looked like before? And granted you're very early in this, but what's it look like now? Which roles have been eliminated? What are the new roles? Just kind of drill down a little bit into what Block looks like today and kind of where it's going.","offset":432,"duration":23},{"text":"Jack Dorsey: Yeah, we are early in it. I mean, just from a, you know, one measurement of how far along we are would be the depth from me to any other individual in the company, and I would say our max depth right now is probably five folks between me and anyone in the company. I would want to get that down to two to three this year.","offset":455,"duration":25},{"text":"Jack Dorsey: And in the most ideal case, you know, there is no layer, everyone in the company reports to me, and that would be, you know, all 6,000 of the company. And that feels somewhat, you know, ridiculous when you consider the old structure. But when you consider that the majority of our work is going through this intelligence layer, it's a lot more manageable.","offset":480,"duration":24},{"text":"Jack Dorsey: And that goes into the roles going forward. We want to normalize down to just three roles. The first is an IC, which is a builder or an operator. This is a salesperson, it's an engineer, it's a designer, product person, 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 10 people to do in the past.","offset":504,"duration":38},{"text":"Jack Dorsey: 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 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.","offset":542,"duration":38},{"text":"Jack Dorsey: 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.","offset":580,"duration":25},{"text":"Jack Dorsey: 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, 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.","offset":605,"duration":30},{"text":"Jack Dorsey: 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, you know, all the soft skills that we recognize great managers are known for.","offset":635,"duration":30},{"text":"Jack Dorsey: But not making it a requirement that they have to be strategic necessarily. They have to build, because they need to show off the skill and teach in that way, but they don't necessarily need to be a DRI. Now, I think 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 or with their direct team.","offset":665,"duration":36},{"text":"Brian Halligan: Just a little kind of before and after, and you're mid on this, let's pretend like it's working great and it's years from now and it's extremely flat. Like what does the role of the CEO before and after? How's that changed? Most of the listeners, by the way, are CEOs. What does, like, planning look like before and after? What happens to all those people who are directors and managers or the glue people? Like what are sort of the before and afters in your mind?","offset":701,"duration":30},{"text":"Jack Dorsey: I think my job as CEO in the past I've thought about in three ways. Number one is to ensure that we have the right principles and the right team dynamic. And that's like hiring and firing and setting values and setting the culture and setting the tone. The second is to ensure that decisions are being made in context of our customers and industry trends and competition. And the third would be to raise the bar on our execution, like to constantly increase our capability and to push ourselves into doing things that are uncomfortable so that we're growing all the time.","offset":731,"duration":34},{"text":"Jack Dorsey: 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 like the architecture of how the company as an intelligence works. And if we're building the company as an intelligence, our job as humans and my job as CEO is to constantly align it to where we think the right outcome is.","offset":765,"duration":28},{"text":"Jack Dorsey: And I see, like, visually I see 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.","offset":793,"duration":27},{"text":"Jack Dorsey: 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 layers of like, okay, so what do we actually build? We build up capabilities, which are effectively our tools.","offset":820,"duration":22},{"text":"Jack Dorsey: 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 TIDAL, we have Bitkey, we have Proto, these are interfaces, these actually touch the real world, touch humans, and we can deliver our capabilities in these interfaces.","offset":842,"duration":24},{"text":"Jack Dorsey: 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'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 something that really tells the truth about your life or your business's life.","offset":866,"duration":22},{"text":"Jack Dorsey: 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 customer's cash flow? Like we have people using us as a bank account. How do we make sure that they can pay their rent and they can pay their Spotify bill and they can pay their kid's allowance?","offset":888,"duration":27},{"text":"Jack Dorsey: And this is all sequenced in a way that allows them to never go to zero, never go negative, and have some cushion that allows them to even think about getting to saving or building wealth. And that's just, 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 have this feature?\" We should just be able to build that and compose it in real time based on our capabilities.","offset":915,"duration":37},{"text":"Jack Dorsey: 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.","offset":952,"duration":23},{"text":"Jack Dorsey: But I think like 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. But it is judgment against like what we intend to build in the world and is it on, is it aligned with that judgment, is it aligned with the values, is it aligned with the taste that we have and is it unique or is it not?","offset":975,"duration":29},{"text":"Jack Dorsey: And I guess for my part I'm the extra checkpoint on like is the alignment circle of humans, that edge of humans actually working correctly.","offset":1004,"duration":9},{"text":"Brian Halligan: And I see how this works exceptionally well for Block, you have a lot of signal. How does this work for, I don't know, Sierra, Workday, somebody who doesn't have the quality signal, the frequency of signal? Does it apply or doesn't work as well?","offset":1013,"duration":8},{"text":"Jack Dorsey: I think it probably does. I think it goes down to like 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. 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.","offset":1021,"duration":33},{"text":"Jack Dorsey: 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 very, very challenging to differentiate and survive.","offset":1054,"duration":28},{"text":"Jack Dorsey: 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 Claude Code in January of 2024. And Claude Code came out that following month and then like was really put into out of beta in May of that year.","offset":1082,"duration":29},{"text":"Jack Dorsey: And, you know, that whole year I just spent every single day for 3 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, I'm sorry, it wasn't 2024, it's 2025.","offset":1111,"duration":23},{"text":"Jack Dorsey: It's only been a year of those tools, like one year, it's just the compounding nature of this is pretty incredible. So 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. They're just living in this abstraction of 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.","offset":1134,"duration":36},{"text":"Brian Halligan: I think you're right. I think if people are thinking of it as copilots and individual productivity versus your, I think your idea is complete business transformation and I think it's super interesting and compelling.","offset":1170,"duration":10},{"text":"Roelof Botha: Can I add one thought I've had as I've listened to this 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 lead to optimal outcomes, but you just need to have the right framework and the right system.","offset":1180,"duration":17},{"text":"Roelof Botha: I think the way that many companies work today is a little bit more command and control. Very much so. And you have hierarchies and you have political actions and people, you know, are jockeying for position and it's 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.","offset":1197,"duration":21},{"text":"Roelof Botha: And you do away with all the layers, you get back to the kind of productivity that founders often long for. They long for the days when they were 100 people and not 500 people because they were so much more productive. Why? Because you had, you know, 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.","offset":1218,"duration":31},{"text":"Roelof Botha: And you can do it with 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 it's much more similar to a capitalist system where the signals tell you what to build. It's not somebody who pounds the table harder who gets their product approved, it's just listen, more customers want this than that, that's how we're going to decide what to build next. For me there's something quite magical in that realization.","offset":1249,"duration":25},{"text":"Brian Halligan: 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 here.","offset":1274,"duration":21},{"text":"Brian Halligan: I have a theory I want to run by you Roelof, 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 the 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?","offset":1295,"duration":26},{"text":"Roelof Botha: Oh, I don't think the AI makes most of the decisions. I think and Jack should correct me here, I think the AI helps with communicating the alignment and the management team or the inner core helps set the framework. What is the objective function? Are we optimizing for growth rate, gross profit per employee, net promoter score, probably some combination of those variables?","offset":1321,"duration":23},{"text":"Roelof Botha: 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 the product, introduce something new.","offset":1344,"duration":26},{"text":"Roelof Botha: 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 hero worship or the converse of that where you sort of scapegoat people. I think it's harnessing the best of of your team to really advance the company. So I subscribe to the circle idea.","offset":1370,"duration":11},{"text":"Jack Dorsey: Yeah, I also don't think the AI is making the majority of the decisions. I think it's facilitating a more context-rich decision. I think ultimately, like in the most ideal case, our customers are actually making the majority of the decisions because they're just based on their queries and what they're trying to do with the system delineates like where our roadmap should go.","offset":1381,"duration":24},{"text":"Jack Dorsey: 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, product feedback on Twitter, all these other things.","offset":1405,"duration":29},{"text":"Jack Dorsey: 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 to do that.","offset":1434,"duration":25},{"text":"Jack Dorsey: 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 in the same hour, in the same thought process of like what is even a company going forward? 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.","offset":1459,"duration":29},{"text":"Jack Dorsey: And it was coming from a place of like wow, is our company just going to be completely irrelevant in the next coming years or even 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 and also to grow that? And like what are the and all that follows from customer expectation?","offset":1488,"duration":27},{"text":"Jack Dorsey: Like the most amazing thing about open-Claude 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 in interface with the Square APIs, and we're seeing Cash App customers, and these are not tech people, these are just like people, \"I want I want a bot to help me manage my life.\"","offset":1515,"duration":-1166},{"text":"Jack Dorsey: That agency, independent of your thoughts on like how good of a system open-Claude is right now, it'll get better and better, but the intent behind that is agency. I want to tangibly control this intelligence and for it to better me and what it makes possible for me is incredible. And that expectation floor has just risen dramatically.","offset":349,"duration":1226},{"text":"Jack Dorsey: And that leads me again to like yeah, 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 and that they, you know, are seeing us as a series of capabilities that makes their desires fast and easy and and valuable.","offset":1575,"duration":25},{"text":"Jack Dorsey: So like it really goes back to the capability set that we have and then 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.","offset":1600,"duration":15},{"text":"Brian Halligan: I spent this morning at a company called Rogo here in New York City. They read your article. Let's say you're advising the CEO of 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 org? Like how should people go about, you know, running the Dorsey playbook?","offset":1615,"duration":23},{"text":"Roelof Botha: Uh, 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 we know there's a lot to figure out.","offset":1638,"duration":12},{"text":"Jack Dorsey: Yeah, it's more like if if you were at 100 people or even, you know, just starting today, if you were to build your company as an AGI, as an intelligence, what would it look like? And what would you need to really differentiate? Like if I were starting a company today, I would be so excited about how quickly I could build things and how quickly I could prototype and get things out to customers.","offset":1650,"duration":23},{"text":"Jack Dorsey: 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. It just like I think distribution really becomes a differentiator.","offset":1673,"duration":27},{"text":"Jack Dorsey: And I think there's some event horizon where the way we think about distribution today closes off. You know, it like there's there's 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 going to be very hard to fight for that.","offset":1700,"duration":24},{"text":"Jack Dorsey: 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 do I need a hierarchy?","offset":1724,"duration":21},{"text":"Jack Dorsey: Brian, a year into Square, I also 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. So we ripped up all the business cards, we normalized down to a title of like you're lead of what, and the longer that is behind lead is probably the farther down you are in the organization.","offset":1745,"duration":29},{"text":"Jack Dorsey: And we've kept it, like we we you know we don't have titles. We have like, you know, what do you lead, going back to like the DRI thing, what are you ultimately responsible for? And I think it's helped us a lot. But this is another step. Like if if you're starting today or you're 100 today, like what what is actually fundamental to solving your customer's problems and and where is the hierarchy getting in the way of that?","offset":1774,"duration":26},{"text":"Jack Dorsey: And look at all the tools you're using. Like look at all the information you're generating just by doing your work. Like just putting that into an intelligence and being able to query it will give you an understanding of the company that like is two to three times more than you had before, ever. Because you're relying upon people telling you things.","offset":1800,"duration":20},{"text":"Jack Dorsey: And, you know, that doesn't always happen for various reasons that, you know, Roelof spoke to in terms of agenda or politics or emotions or empathy, all all these things. Imagine if your company was entirely legible. Like entirely legible every aspect of it. And we're not far off from that from a data perspective. It's putting the intelligence on top of it and making it useful and then making it proactive.","offset":1820,"duration":28},{"text":"Jack Dorsey: 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 customers is still right now very much a research bet. But like it's imminently solvable.","offset":1848,"duration":17},{"text":"Brian Halligan: Mm. 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 should it be, how bold should it be? You know, Ruth Porat's got this good line, if you're going to eat a shit sandwich, don't nibble. And you seem like you took a big bite. What was that debate behind the scenes and then Roelof, like how did he pitch it to you guys and what was the board's reaction? Just like behind the scenes on that.","offset":1865,"duration":35},{"text":"Jack Dorsey: Yeah. So December of last year is when the model is really got a noticeable upgrade from being able to be really good at building prototypes and greenfield efforts to like understanding like large codebases and legacy codebases 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 became suddenly very mature. Like just in that month.","offset":1900,"duration":35},{"text":"Jack Dorsey: And it just like 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 this way if you had these tools today? Like what would the company look like?\"","offset":1935,"duration":23},{"text":"Jack Dorsey: 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 a cap on our layers to four, me plus four, and all these like small things.","offset":1958,"duration":26},{"text":"Jack Dorsey: 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. And then we just did this exercise of like okay, so what is the minimum number of people that we would need to keep the service up 100%? And then next, what is the minimum 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.","offset":1984,"duration":34},{"text":"Jack Dorsey: And then third, what is the minimum set of folks that we need in order to grow, to fulfill our commitments we've made to the street, but also rebuild the company as an intelligence. And that's roughly the number that we got to and we built in some buffer in case we made mistakes, which we did. And you know, hard hard not to, especially operating the way we have.","offset":2018,"duration":25},{"text":"Jack Dorsey: 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 that and and there was a span of exploration to execution and, you know, under under three weeks.","offset":2043,"duration":22},{"text":"Jack Dorsey: And I think generally I wanted to make sure that we if we knew that this was what our company was going to be in the future, I didn't want to have to do it with our backs against the wall. We're a public company and there's various challenges there, and other companies will will probably get to this realization at some point.","offset":2065,"duration":24},{"text":"Jack Dorsey: I don't want to react to that. 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 part, to leave, and even for the people that we're asking to stay and we're not just reacting into something mediocre, we're acting towards excellence. And like that's just the tone that we wanted to set.","offset":2089,"duration":28},{"text":"Jack Dorsey: So, you know, every day was just like constantly checking like are we doing the right thing, is this the right set of folks, like what are we not thinking about, what are we not talking about? And we you know we kept the the group very, very tight and had a conversation with with a board, which was a my perspective very open to it and actually more than open, more like, \"Yes, we agree, like we should we should do this.\" But I'll let Roelof speak to that.","offset":2117,"duration":37},{"text":"Roelof Botha: It was a very quick process. I think part of what helps is that Jack had written us a very detailed note laying out the logic. It's principled. It's not reactive as Jack was saying, it's not reactionary, it's very well laid out, very logical.","offset":2154,"duration":17},{"text":"Roelof Botha: 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 they 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 is different from where we ultimately landed by the time the announcement took place.","offset":2171,"duration":27},{"text":"Roelof Botha: And I also think it's just 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.","offset":2198,"duration":20},{"text":"Brian Halligan: You two, Roelof you've been on a lot of boards, Jack you've had your ups and downs with different boards. Any advice for these CEOs listening that should they start at 100 employees, should they start bringing in independents, should they 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?","offset":2218,"duration":21},{"text":"Jack Dorsey: I mean early on I always told myself and my team that like your your first board is your investors, right? And I would treat that relationship as a hire you can never fire, and in fact they can fire you, and I've been on the other side of that. So it really puts pressure on finding the right person that you'd actually want to work with at the company knowing that you could never fire them.","offset":2239,"duration":31},{"text":"Jack Dorsey: 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 Roelof, you know, we we we were optimizing for him to be on our board and be an investor.","offset":2270,"duration":23},{"text":"Jack Dorsey: But like 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 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?","offset":2293,"duration":33},{"text":"Jack Dorsey: And I think you have to build a board that has different perspective on that and that is open to wild ideas, 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 like really document it and paint a picture of like where this could go and like what the opportunity cost is if we don't do something.","offset":2326,"duration":27},{"text":"Jack Dorsey: Because if we didn't do something like this, I just imagine like every year it's a 10% RIF or 20% RIF 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.","offset":2353,"duration":18},{"text":"Jack Dorsey: And I, you know, had a conversation with a board about 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 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.","offset":2371,"duration":17},{"text":"Roelof Botha: Well 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 it'll have a much bigger bearing on the ultimate outcome of your company.","offset":2388,"duration":23},{"text":"Roelof Botha: 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, you know, described that sometimes, you know, that person may come to the conclusion that the founder's no longer the right person to run the company, maybe rightly, maybe wrongly.","offset":2411,"duration":24},{"text":"Roelof Botha: 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.","offset":2435,"duration":18},{"text":"Roelof Botha: I think boards are often built too late in a rush, especially in the run up up to an IPO where people suddenly realize, \"Ooh, I've got a four-person board and I need nine,\" whatever the case is, and then you suddenly assemble people who have no context, they have no history, and they have no chemistry, because you will be tested.","offset":2453,"duration":19},{"text":"Roelof Botha: You're going to have a situation where there's a short-seller report or you're dealing with a hostile, you know, situation with activist investor or a tricky financing, you know, 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.","offset":2472,"duration":21},{"text":"Brian Halligan: Jack, you've started a couple great companies here, you're a startup founder, scale-up CEO. Roelof, he was the only person to have founded two companies that made it into the S&P 500. That's amazing. And the only person to have been simultaneously CEO of two public companies, for the record.","offset":2493,"duration":23},{"text":"Jack Dorsey: Which should not be should not be a goal for anyone, by the way.","offset":2516,"duration":2},{"text":"Brian Halligan: Let me ask him, he's CEO of two companies. Is it ever a good idea?","offset":2518,"duration":3},{"text":"Jack Dorsey: Not public companies. Private maybe. Private 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 definitely like an anti-goal, it's an anti-pattern.","offset":2521,"duration":15},{"text":"Brian Halligan: 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 growing really fast? Like yeah, what do you got?","offset":2536,"duration":15},{"text":"Jack Dorsey: My only regrets in life and and also in our in our businesses, um, are where I decided not to learn something. Because I 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, like that's that's what I regret.","offset":2551,"duration":29},{"text":"Jack Dorsey: And, you know, in in probably the worst case in any of these companies, just delegating way too much. 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.\"","offset":2580,"duration":24},{"text":"Jack Dorsey: And like we got like you know the CEO over here for Square and CEO over here for Cash App and like the value of our company is not like these, you know, unrelated things that are growing at different clips, it's how do we bring them together and like really, you know, um, challenge the whole financial network entirely, because we have we have both sides of the counter.","offset":2604,"duration":22},{"text":"Jack Dorsey: 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 one thing that I probably consistently would have corrected would be just delegating too much. You know, too too much of that and I didn't learn that fast enough. Like that's that's the regret, is I didn't choose to to learn from that fast enough.","offset":2626,"duration":31},{"text":"Jack Dorsey: But when you have your whole your entire company is 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?","offset":2657,"duration":29},{"text":"Jack Dorsey: And and that's hence the shift. Like I I can't imagine doing anything bigger than rebuilding our company as an intelligence um, or more correct um given where where everything is trending. So it just feels like I have to constantly build um and constantly learn from whatever we're putting out there in order for us to stay relevant going forward.","offset":2686,"duration":21},{"text":"Roelof Botha: 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?","offset":2707,"duration":14},{"text":"Jack Dorsey: Well I mean just two months ago, every meeting that we would have would come you mean you you you have this Brian, 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 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.","offset":2721,"duration":37},{"text":"Jack Dorsey: 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 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 what is the right path?","offset":2758,"duration":33},{"text":"Jack Dorsey: 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.","offset":2791,"duration":13},{"text":"Brian Halligan: I I completely agree with you, like a lot of times in HubSpot's history what worked was when we were doing a lot of different stuff and we were distracted, 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. Do you have a reaction to that?","offset":2804,"duration":20},{"text":"Jack Dorsey: Yeah it's uh I think it's I think it's having a wider perspective to start and then because in the past 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.","offset":2824,"duration":22},{"text":"Jack Dorsey: But today we can do it in an hour. And then um 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 um and just constantly pushing these these models to to doing something that they weren't they weren't we didn't think they were capable of.","offset":2846,"duration":35},{"text":"Jack Dorsey: And that's where I think the magic still happens and where where I think the focus still comes to bear um because at the end of the day 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 and the world model, then you know it just changes everything. So I don't even know if the question matters anymore.","offset":2881,"duration":20},{"text":"Brian Halligan: 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 BlueSky, interesting stuff with Spiral. Advice to CEOs trying to figure that second act out?","offset":2901,"duration":14},{"text":"Jack Dorsey: Uh, I don't know if I ever considered to be like a second act, it's just something that like we had I wanted to do and I had to do and it was interesting.","offset":2915,"duration":7},{"text":"Brian Halligan: How's building something new distracting to the org and like how do you resource it?","offset":2922,"duration":4},{"text":"Roelof Botha: Well Cash App was like that in early days.","offset":2926,"duration":1},{"text":"Jack Dorsey: 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 we we had multiple moments and these are the founding moments that um I think are critical for a company.","offset":2927,"duration":23},{"text":"Jack Dorsey: But like we were we started with a card reader, eventually we determined that \"Hey we should probably lend money to sellers\" because like no seller wants to accept credit cards, what they want is to get more sales. And what helps them get more sales? More capital to deploy into their business.","offset":2950,"duration":18},{"text":"Jack Dorsey: When we first brought it to our board, um our board said absolutely no. Like you're not getting into the lending business, like it's ridiculous. And we lost I lost some credibility with with the board and our population because we wanted to do this and we kept pushing it and pushing it and eventually they said yes.","offset":2968,"duration":19},{"text":"Jack Dorsey: Cash App was the same thing where we were about merchants, our mission was make commerce easy, and we built this thing that allowed effortless peer-to-peer, as effortless as just you know sending an email to start. And uh our our COO at the time was on the founding team of PayPal or uh Keith Rabois. And even he said no, and he said like you know this is a solved problem.","offset":2987,"duration":24},{"text":"Jack Dorsey: Everyone in the company hated Cash App, it was a team of eight people. And uh hated it for two to three years, we mentioned it less than eight times in our S-1 to go public. Um our investors didn't understand it at all. And every day that I allowed it to persist and defended it, I lost credibility.","offset":3011,"duration":22},{"text":"Jack Dorsey: 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 comfortable 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 and you're okay with yeah people aren't going to trust me for a bit and it's okay. Um I'm I'm staking part of my reputation on this and this I believe it. I think it makes all those answers stronger, by the way.","offset":3033,"duration":38},{"text":"Brian Halligan: I have a weird story for you, when Sequoia was hiring me they write a memo when they're investing in a company or when they're hiring someone and the memo on me was one of my strengths was I was DGAF, don't give a flock, and one of my weaknesses was I was DGAF, I don't give a flock. You strike me as someone who's has high DGAF and you stick with your convictions for a very long periods of time. Founders struggle with that. I struggle with that. Advice?","offset":3071,"duration":30},{"text":"Jack Dorsey: Yeah I would say it wavers for me. Like it 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 made a I made a decision some time ago when I first became CEO of Twitter, everyone was telling me I needed a uh CEO coach.","offset":3101,"duration":19},{"text":"Brian Halligan: Hmm.","offset":3120,"duration":1},{"text":"Jack Dorsey: And I got the CEO coach and he was a great guy but like I was learning absolutely nothing. And it it just reminded me of all these times when you put so much emphasis on like who's my mentor, who am I learning from, who's my mentor, who am I learning from? And around that time I just decided I'm 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.","offset":3121,"duration":30},{"text":"Jack Dorsey: And to for it to be a mentor I have to decide that I'm going to learn something from it. Like 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?","offset":3151,"duration":20},{"text":"Jack Dorsey: 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 what not. 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?","offset":3171,"duration":20},{"text":"Jack Dorsey: 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? Um and uh you know sometimes I I get to the right answer, sometimes I don't, and I just like continue in my ways and it's a failure. But I just having that mindset instead of having this one mentor in your life now you have infinite mentors. Like you know it's it's just an amazing way to approach life and challenges that that I found.","offset":3191,"duration":29},{"text":"Brian Halligan: You're definitely a learner, talked a lot about it on other, I've seen you talk about it a lot. You're a meditator. Should all CEOs meditate? What are the benefits you get as the CEO? And what do you take from Marc Andreessen talking about how he's very he's not introspective? I thought that was an interesting comment. Like talk about in meditation, CEOs, what do you get from it? Yeah.","offset":3220,"duration":26},{"text":"Jack Dorsey: Him saying that he's not introspective is very introspective of him, just to be clear. Um I didn't get a lot from that. But 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 have 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.","offset":3246,"duration":27},{"text":"Jack Dorsey: But if you actually get into like true meditation, it's a very physical thing. Like it's a very physical um practice and what you're doing is you're training your mind to focus on one point. One point. Like the the meditation retreats I did were 10 days and you spend the first 3 days sitting from 4:30 in the morning till 9:00 p.m. focusing on the feeling of your breath on your upper lip. Yep.","offset":3273,"duration":24},{"text":"Jack Dorsey: Just that and just the sensation of it. And what you're training your mind to do is to sharpen your focus and then just to observe. Observe the sensation without reacting to it from an emotional or intellectual standpoint. 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.","offset":3297,"duration":33},{"text":"Jack Dorsey: If I were to stand up, it goes away. Hmm. 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 in 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.","offset":3330,"duration":24},{"text":"Jack Dorsey: 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.","offset":3354,"duration":28},{"text":"Brian Halligan: Maybe just close on, start with you Roelof. There's some timeless qualities of CEOs um that last the test the time. And Roelof you you you're involved with YouTube, Instagram, Block, Mongo, Unity. What are timeless CEO qualities and what is new? Like what are the new qualities CEOs need today?","offset":3382,"duration":30},{"text":"Roelof Botha: I like acronyms, so I came up with one which is 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? Are you predictable? Are you rational? Or do you fly off the handle?","offset":3412,"duration":29},{"text":"Roelof Botha: And are you empathetic? Do you really care about the team that you manage? Do you really care about the business? Um you know, sort of 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 just hard to keep it in your mind.","offset":3441,"duration":12},{"text":"Roelof Botha: 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.","offset":3453,"duration":23},{"text":"Roelof Botha: And I think the same is true here. Yes companies are being built differently, yes AI's 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 you know basics of dealing with people and leading remain true.","offset":3476,"duration":18},{"text":"Roelof Botha: The one I would say is probably different is the pace of of change is so fast. And I think, you know, kudos again to Jack for the the speed with which we're moving on this decision because it would have been easy to dither for 6 or 12 months on this decision. So you've got to move fast.","offset":3494,"duration":19},{"text":"Brian Halligan: Mm. 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 things. What do you think? And what's what's what's timeless, what's changed?","offset":3513,"duration":10},{"text":"Jack Dorsey: 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, um or how rigid you are uh towards your past, the company's past and its sacred cows or what the competition is doing.","offset":3523,"duration":29},{"text":"Jack Dorsey: Um it's just 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.","offset":3552,"duration":14},{"text":"Brian Halligan: Has it always been valuable or is it more valuable because things are moving so fast right now?","offset":3566,"duration":4},{"text":"Jack Dorsey: I think it's more valuable. Like being able to, 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 what the tools do and like this is the way we do things and I think people will um because we're offloading some of our intelligence to intelligences, and people will go along with um more likely to to default to what these things are suggesting rather than seeing them as an input.","offset":3570,"duration":33},{"text":"Jack Dorsey: Like I I think we're still in the mode where most people are seeing all what the intelligences do, these tools do as output rather than better input to create better output ourselves. Um and I like I think that's important to me like when I was doing that like everyday 3 hours, like this is input to me and it's now up to me to like really um 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.","offset":3603,"duration":31},{"text":"Jack Dorsey: So having someone who's able to discern signal from noise and cool from not, relevant, you know, like there is, you know, this is highly overused right now, um the the taste thing is real and 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?","offset":3634,"duration":29},{"text":"Jack Dorsey: 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 that are just copies of copies of copies of copies because it's easy instead of like what's your what's your point of view? Like what what is opinionated in this and like where where is it pushing the the boundaries and where is it uncomfortable?","offset":3663,"duration":34},{"text":"Brian Halligan: Mm. I think that's brilliant. It's a great place to end. Thank you both for coming on Long Strange Trip. I love the article you wrote, I think it's going to be game-changer for lots of companies. Appreciate you both.","offset":3697,"duration":9},{"text":"Jack Dorsey/Roelof Botha: Thank you. Thank you. Thank you, Brian. Thank you, Jack. Thank you.","offset":3706,"duration":4},{"text":"Brian Halligan: Hope you liked 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.","offset":3710,"duration":28},{"text":"Brian Halligan: And I sort of think of it as like when I grew up in my career, I worked at this company PTC in the 90s. It was very, very Manager Mode, uh very hierarchical, uh the power rested in the VPs essentially. Uh when I ran HubSpot, they didn't call it Founder Mode then but it was kind of Founder Mode. Instead of being a pyramid, it was flat and a lot of power was rested in the in the founder's hands.","offset":3738,"duration":25},{"text":"Brian Halligan: Um he sort of proposing the Dorsey Mode in my mind. He laughed about it when I said it, but I think of it as like what's next? And it's more like a circle than a really flat organization and the power rests in the kind of in the system and the system makes a lot of decisions and can react real time to the employees and the customers.","offset":3763,"duration":24},{"text":"Brian Halligan: But I think of Dorsey Mode as getting rid of the hierarchy all together, building basically the brain, getting the inputs right, and having it make a lot of the decisions that a hierarchy used to. I think he's onto something, I'm curious to see what you think. Um comment on Twitter, comment on on YouTube. I'm I'm curious about your thoughts on it. I think Jack would be curious too. He's in the very early innings of rolling this out and he's looking for feedback on it. Anyway, appreciate you all. Thanks for tuning in.","offset":3787,"duration":15}],"logs":[{"elapsed":"0.0","message":"Downloading audio from YouTube...","detail":null},{"elapsed":"0.0","message":"Trying download with browser cookies (ad-free)...","detail":null},{"elapsed":"30.9","message":"Audio downloaded (31.9 MB) in 30.9s","detail":"File size: 31.9 MB"},{"elapsed":"30.9","message":"Video title: Jack Dorsey: Every Company Can Now Be a Mini-AGI","detail":null},{"elapsed":"30.9","message":"Audio duration: 1:03:41 (63.7 min)","detail":null},{"elapsed":"30.9","message":"Uploading audio to Gemini File API...","detail":null},{"elapsed":"35.4","message":"Audio uploaded in 4.5s","detail":"File ref: files/mx4izzo8q2u1"},{"elapsed":"35.4","message":"Audio processed in 0.0s. 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