[ { "speaker": "Speaker 1", "text": "since last year I've just had this existential dread and also like hope and optimism at in the same hour in the same thought process of like what is even a company going for it like what" }, { "speaker": "Speaker 1", "text": "like what are these structures going forward?" }, { "speaker": "Speaker 1", "text": "And this is the only like durable one structure that I could actually imagine lasting for quite some time. And it it was coming from a place of like wow is our company just going to be completely" }, { "speaker": "Speaker 1", "text": "irrelevant you know in the next coming years." }, { "speaker": "Speaker 2", "text": "All right everybody we had Jack Dorsey on the pod today founder of Twitter and founder of Block." }, { "speaker": "Speaker 2", "text": "He's the only founder to have two of his companies end up on the S&P 500." }, { "speaker": "Speaker 2", "text": "listening that today that's pretty cool." }, { "speaker": "Speaker 2", "text": "Also Roelof Botha who's a Square partner and is on Jack's board at Block. The conversation was super interesting to me. He recently put an article out that you may have seen called from hierarchy" }, { "speaker": "Speaker 2", "text": "to intelligence. And it's a manifesto on how to rethink basically rethink from the first principles how an organization works." }, { "speaker": "Speaker 2", "text": "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." }, { "speaker": "Speaker 2", "text": "Block is really changing the way it's organized. Before we started he said I'd love to get some feedback from you and from other people on this. So if you get comments on it let her rip. He wants" }, { "speaker": "Speaker 2", "text": "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" }, { "speaker": "Speaker 2", "text": "CEOs as you folks know. Like how do you build an amazing board? He's certainly got some scars around board building." }, { "speaker": "Speaker 2", "text": "How do you build your second act like the cash app versus the the original business of of Square. Is it a good idea to be a CEO of two different companies at the same time?" }, { "speaker": "Speaker 2", "text": "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" }, { "speaker": "Speaker 2", "text": "of a modern CEO. So tune in. I'll be back at the end and give you some further thoughts but I I thought Jack did a really nice job and and Roelof did too. Let's get into it. Jack I read your" }, { "speaker": "Speaker 2", "text": "piece. I think it's fantastic from hierarchy to intelligence." }, { "speaker": "Speaker 2", "text": "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" }, { "speaker": "Speaker 1", "text": "led you to this?" }, { "speaker": "Speaker 1", "text": "I don't know if um there's one thing that's ultimately wrong. Um it's just it's it's recognizing that like what what do we what do we see in the in the pattern? What what is the function of the hierarchy?" }, { "speaker": "Speaker 1", "text": "And um what we wanted to explore is just like what where does it actually come from and and why did why does it exist in the first place?" }, { "speaker": "Speaker 1", "text": "And if you look at it from first principles it's all about information flow to a broad base of people. Um so being able to communicate over a breath of of people and um have that be manageable at a human" }, { "speaker": "Speaker 1", "text": "scale." }, { "speaker": "Speaker 1", "text": "So we've gotten into structures that you know we've borrowed and iterated on a little bit over 2,000 years. Yeah. Um and now we're we're facing this um I think a a completely foundational" }, { "speaker": "Speaker 1", "text": "moment in being able to question every element of how we work." }, { "speaker": "Speaker 1", "text": "And the one that I think is questioned the least is probably the hierarchy. And probably about how we manage communication flow around the companies." }, { "speaker": "Speaker 1", "text": "So if if we're in a world where we are today where Block for instance is completely remote or we're remote first every single thing that we do creates some sort of artifacts whether it be a" }, { "speaker": "Speaker 1", "text": "Slack message an email um pull request code um you know all these Google document a meeting that we record all these things have these artifacts of information about how the company" }, { "speaker": "Speaker 1", "text": "is is working is building is failing is making mistakes all these things." }, { "speaker": "Speaker 1", "text": "And traditionally we've been relying upon humans in a management structure in a hierarchy to go up and down a chain to relay that information." }, { "speaker": "Speaker 1", "text": "Instead we can take all of those artifacts and put an intelligence on top of it." }, { "speaker": "Speaker 1", "text": "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" }, { "speaker": "Speaker 1", "text": "access to information and and same understanding of like what the company can do. So you get to a point where you can build these world models for companies like treat the company as a as" }, { "speaker": "Speaker 1", "text": "a mini AGI for instance an artificial general intelligence because it really is. I mean if you look at a company it is an intelligence but it hasn't been structured in the way that's the most" }, { "speaker": "Speaker 1", "text": "efficient or um the least lossy in terms of uh information flow and and what people can actually do within the company. So um the technology is good enough today that we can actually model the company." }, { "speaker": "Speaker 1", "text": "We can have everyone in the company um put in intent which would be strategy or these artifacts and and we can also have everyone in the company query it as well and and it just it really opens the door for" }, { "speaker": "Speaker 1", "text": "what's possible like you know Roelof and I have a board meeting every quarter where we we construct a bunch of board docs slides presentations um we get only so much time for them to" }, { "speaker": "Speaker 1", "text": "have questions but imagine if every single board member can just query the company and have a conversation with the company's intelligence in real time and we can make that that meeting time that" }, { "speaker": "Speaker 1", "text": "we that we have every quarter really focused on more of the creative or bigger existential decisions and issues than the day-to-day. The same can be said for like our earnings call and analysts like you" }, { "speaker": "Speaker 1", "text": "giving them like fully reg FD possible information that is on their timeline with with their questioning." }, { "speaker": "Speaker 1", "text": "Um but you can scale this to any position or any role in the company which is pretty phenomenal and like we've just never had that ability before and and now we do and you know I think the" }, { "speaker": "Speaker 1", "text": "the architecture and the structure of the company is ultimately going to determine its velocity and how well it's road map for customers correct." }, { "speaker": "Speaker 2", "text": "And do 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? Um what are" }, { "speaker": "Speaker 2", "text": "the new roles? Um just kind of drill down a little bit into what Block looks like today and kind of where it's going." }, { "speaker": "Speaker 1", "text": "Yeah we we we are early in it. Um I mean just from a you know one one measurement of of how far along we are would be the depth from me to any other individual in the company. And I would say our our max" }, { "speaker": "Speaker 1", "text": "depth right now is probably five. Okay." }, { "speaker": "Speaker 1", "text": "Uh folks between me and and anyone in the company. Um I would want to get that down to two to three uh this year and in the most ideal case you know there there is no layer everyone in the company reports to me." }, { "speaker": "Speaker 1", "text": "And that would be you know all all 6,000 of of the company and that feels somewhat you know ridiculous when you consider like the old structure but when you consider that um the majority of our work is" }, { "speaker": "Speaker 1", "text": "going through this intelligence layer um it's a lot more manageable and it that goes into the roles uh going forward. We we want to normalize down to just three roles. Mhm." }, { "speaker": "Speaker 1", "text": "The first is an IC which is a a builder or an operator. This is a sales person this is an engineer it's a designer. Um a product person like you know whatever it is they're actually working" }, { "speaker": "Speaker 1", "text": "with the tools to build or to operate the company. Mhm. Um they're augmented because they have access to agents. So you know one person can you know potentially do the work or explore the" }, { "speaker": "Speaker 1", "text": "breath that you know it would take a team or you know 10 people to do in the past." }, { "speaker": "Speaker 1", "text": "So that's number one and then I think there's a durable human skill that lasts there which is judgment and taste and creativity. Mhm. Um so that's probably the largest part of the population is" }, { "speaker": "Speaker 1", "text": "the builder and the operators ICs. The second role is the DRI." }, { "speaker": "Speaker 1", "text": "And that's someone who can own the customer outcomes. Mhm. They're putting uh strategy together. They're understanding what road map um uh allows us to solve customer customer needs and and problems." }, { "speaker": "Speaker 1", "text": "And they're assembling a team of these ICs uh to get something done. Um but the the durable human human skill there is ownership and accountability. Um you know they're really owning the the outcomes and" }, { "speaker": "Speaker 1", "text": "whether something is failing or not." }, { "speaker": "Speaker 1", "text": "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" }, { "speaker": "Speaker 1", "text": "but instead of telling them how to do it they're showing them how to do it by doing the work. So, these are these are people who might be ICs or they might be DRIs, but they're also really good at giving" }, { "speaker": "Speaker 1", "text": "um coaching skills at at a coaching skill to help the the people around them get better and better and master their craft." }, { "speaker": "Speaker 1", "text": "And today, that's a management structure where where these where ICs and even DRIs report to a player coach. Mhm. But I think in the future, it's an assignment. It's not a um reporting structure, but I'm" }, { "speaker": "Speaker 1", "text": "assigned to ICs or I'm assigned to DRIs to help them master their craft. And obviously, the durable human uh skill there is building human capacity and and coaching. Um and there's a lot of empathy there and you" }, { "speaker": "Speaker 1", "text": "know, all the all the soft skills that we recognized um great managers are are known for." }, { "speaker": "Speaker 1", "text": "Um but but not making it a requirement that they have to be strategic necessarily. They have to build um because they need to show off the skill and and and teach in that way, but they don't necessarily need to be a" }, { "speaker": "Speaker 1", "text": "DRI. Now, I I in very rare cases, one person can take on all three of those roles. I think I can take on all all three of those roles. My leadership team is expected to take on all three of" }, { "speaker": "Speaker 1", "text": "those roles. They expected to build as an IC or operate the company." }, { "speaker": "Speaker 1", "text": "They're expected to be strategic and actually think about road maps and customer outcomes. And they're expected to coach and um help raise the skill level um around them uh with with the" }, { "speaker": "Speaker 1", "text": "people that they work with their with their direct team." }, { "speaker": "Speaker 2", "text": "Just a little kind of before and after and your your mid on this and let's pretend like it's working great and it's 2 years from now." }, { "speaker": "Speaker 2", "text": "And it's extremely flat." }, { "speaker": "Speaker 2", "text": "Like what is what is the role of the CEO before and after? How's that Most of the listeners, by the way, are CEOs." }, { "speaker": "Speaker 2", "text": "Um what does like planning look like before and after?" }, { "speaker": "Speaker 2", "text": "Um what happens to all those people who are directors and managers or the kind of glue people? What are some kind of the before and afters in your role?" }, { "speaker": "Speaker 1", "text": "I think um my my my job as CEO in the past I thought about in three ways. Number one is to ensure that we have [snorts] the right principles and the right team dynamic. Mhm." }, { "speaker": "Speaker 1", "text": ">> And that's like hiring and firing and setting values and setting the culture and setting the tone. Mhm. The second is to ensure that decisions are being made in in context of our customers and industry" }, { "speaker": "Speaker 1", "text": "trends and competition." }, { "speaker": "Speaker 1", "text": "And the third would be to raise the bar on our execution. Like to constantly increase our capability and and to push ourselves in to doing things that are uncomfortable so that we're growing all the time. So," }, { "speaker": "Speaker 1", "text": "that's how I thought about my job up until this point." }, { "speaker": "Speaker 1", "text": "I think in the in the future, you you have those elements certainly, but I think it's more about like the architecture of how the the company as an intelligence works." }, { "speaker": "Speaker 1", "text": "And like if we're building a company as an intelligence, our job is as humans and and my job as CEO is to constantly align it to where we think the right outcome is. Mhm. And I I see like, you know, visually I see" }, { "speaker": "Speaker 1", "text": "the the comp the intelligence, the world model for the company in the center." }, { "speaker": "Speaker 1", "text": "And then on the edge are the humans who are just constantly aligning this towards customer outcomes. Mhm. But even even that changes, I believe, because I think a company's ultimate" }, { "speaker": "Speaker 1", "text": "limiting factor is its own road map." }, { "speaker": "Speaker 1", "text": "And I think what what these technologies point to are that our customers are going to they're going to have the expectation that they can ask for a future that doesn't exist on a road map and that it just is served" }, { "speaker": "Speaker 1", "text": "to them. Mhm. And that's where like you really get into the the layers of like, okay, so what do we actually build? We build up capabilities, which are effectively our tools. Like we can issue" }, { "speaker": "Speaker 1", "text": "cards, we card acceptance, peer-to-peer lending, all these things we do as a financial technology company. Mhm. We have these interfaces like Square, which has a register and a dashboard. We have" }, { "speaker": "Speaker 1", "text": "Cash App, we have Title, we have Bitkey, we have Proto. These are interfaces." }, { "speaker": "Speaker 1", "text": "These actually touch the real world, touch humans, and we can deliver our capabilities in these interfaces. Today, they're built with like these very specific navigations that are our road" }, { "speaker": "Speaker 1", "text": "map and our understanding of what our customers want." }, { "speaker": "Speaker 1", "text": "When you move to the third layer, you have proactive intelligence. We have all this understanding of our customers. We have We're moving money. Money is the most honest signal in the world. Um you can lie about" }, { "speaker": "Speaker 1", "text": "literally everything, but when a transaction occurs, like that's that's something that like really tells the truth about your life or your business's life." }, { "speaker": "Speaker 1", "text": "And um 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" }, { "speaker": "Speaker 1", "text": "protect our customers' cash flow?" }, { "speaker": "Speaker 1", "text": "Like we have people using us as a bank account." }, { "speaker": "Speaker 1", "text": "How do we make sure that they can pay the rent and they can pay their Spotify bill and they can pay um their kids' allowance and and and this is all sequenced in a way that allows them to never go to zero," }, { "speaker": "Speaker 1", "text": "never go negative, and have some cushion that allows them to even think about um getting to saving or building wealth." }, { "speaker": "Speaker 1", "text": "And and that's just, you know, peace of mind, I think is the most critical aspect here." }, { "speaker": "Speaker 1", "text": "Um so if if we're enabling a customer, if we're able to prompt a customer and also they can ask like as a business, hey, I have this inventory thing that I've been using, but it's missing this feature. Can I Can I" }, { "speaker": "Speaker 1", "text": "have this feature? We should just be able to build that and compose it in real time based on our capabilities." }, { "speaker": "Speaker 1", "text": "If we can't, and it points to a deficiency in capabilities or a gap, that's our road map. Yeah." }, { "speaker": "Speaker 1", "text": ">> So, our our customers just by using and talking with our systems are telling us what our road map should be and then it's up to us to give the judgment. Mhm." }, { "speaker": "Speaker 1", "text": "And then the final layer is is the world model. It's the customer world model." }, { "speaker": "Speaker 1", "text": "It's the company world model. Our our deep understanding of our of um ourselves and and also our customers. But I I think like if I had to if I had to say one one thing that, you know, myself or anyone" }, { "speaker": "Speaker 1", "text": "in the company has to do, it's I guess it's this overused phrase of of judgment. Um but it is judgment against like what we intend to build in the world. Mhm. And is it on Is it aligned with that judgment? Is it" }, { "speaker": "Speaker 1", "text": "aligned with the values? Is it aligned with the taste that we have and is it unique or is it not? Mhm. And I I guess in for my part I'm the um extra checkpoint on like, is the alignment" }, { "speaker": "Speaker 1", "text": "circle of humans, the edge of humans actually working correctly?" }, { "speaker": "Speaker 2", "text": "In this I see how this works exceptionally well for Block. You have a lot of signal." }, { "speaker": "Speaker 2", "text": "How does this work for I don't know, Sierra, Workday, somebody who doesn't have the quality signal, the frequency of signals. Does it apply or it doesn't work as well? I think it probably does. It I think it it goes" }, { "speaker": "Speaker 1", "text": "down to like, are you building a Are you building a business that like understands something of human nature deeply and it gets deeper every single time." }, { "speaker": "Speaker 1", "text": "And and that's a real tangible signal that just doesn't go away or and if you are, then I think you can build your company as an intelligence. If you're not, then it's probably a an add-on to something else. Um" }, { "speaker": "Speaker 1", "text": "And I I think most of the industry is thinking about AI as like a co-pilot, as something that is augmented onto rather than like, how do you just rebuild this our whole company with this as the core?" }, { "speaker": "Speaker 1", "text": "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 um the frontier labs, then I I think it's going to be a" }, { "speaker": "Speaker 1", "text": "very very challenging to differentiate and and um and and survive. And and that's kind of what's been leading me to all this is like I I just, you know, since uh January of 2024, which is when these" }, { "speaker": "Speaker 1", "text": "tools really uh came to bear. Like we Goose, um which is a agent coding harness, was 1 month before Claude Code in January of 2024. Mhm. And Claude Code came out um the following month and then" }, { "speaker": "Speaker 1", "text": "like was really put into out of beta in May of that year. Mhm. 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" }, { "speaker": "Speaker 1", "text": "to do something that I didn't think it was capable of or I didn't think I was capable of. Mhm. And every single day it it worked. Like every single day I was surprised." }, { "speaker": "Speaker 1", "text": "And it's it's, you know, it's it I'm sorry, it wasn't 2024, it's 2025. It's only been a year of those tools." }, { "speaker": "Speaker 1", "text": "Like 1 year. It just the the compounding nature of this um is pretty incredible. So, you know, being able to like uh see that, understand it, and then shift your company to be ahead of it, I" }, { "speaker": "Speaker 1", "text": "think is absolutely critical right now." }, { "speaker": "Speaker 1", "text": "And I don't think people are feeling it enough. Mhm. It it they're just living in this abstraction of like, oh yeah, like uh these tools will make everyone in our company 10x more productive. I I don't" }, { "speaker": "Speaker 1", "text": "think this is a productivity thing. I think it's a structural thing that needs to shift. I think you're right. I think people are thinking of it as co-pilots and individual productivity versus your" }, { "speaker": "Speaker 2", "text": "I think your idea is complete business transformation and I think it's super interesting and compelling. Can I add one Yes." }, { "speaker": "Speaker 3", "text": "Thought I've had as I've listened to this so far." }, { "speaker": "Speaker 3", "text": "You know, one of the one of my favorite pieces uh of writing ever is Adam Smith, Wealth of Nations." }, { "speaker": "Speaker 3", "text": "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" }, { "speaker": "Speaker 3", "text": "need to have the right framework and the right system. I think the way that many companies work today is a little bit more command and control." }, { "speaker": "Speaker 3", "text": "Very much." }, { "speaker": "Speaker 3", "text": ">> And you have hierarchies and you have political actions and people, you know, jockeying for position and it's it's not always clear what is actually true." }, { "speaker": "Speaker 3", "text": "And I think part of what we're envisioning here is you have a system that's just ground truth." }, { "speaker": "Speaker 3", "text": "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 cuz they were so much" }, { "speaker": "Speaker 3", "text": "more productive. Why? Because you had, you know, lots of transparency, limited hierarchy." }, { "speaker": "Speaker 3", "text": "And so I think the possibility here is Jack was saying is instead of just focusing on individual productivity, you reimagine how we work together as humans." }, { "speaker": "Speaker 3", "text": "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 a it's much" }, { "speaker": "Speaker 3", "text": "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" }, { "speaker": "Speaker 3", "text": "customers want this than that. That's how that's how we're going to decide what to build next. So for me, there's something quite magical in that realization. Yeah. About 4 years into" }, { "speaker": "Speaker 2", "text": "building HubSpot, I eliminated no org charts, no titles, and everyone lost their mind. They didn't like the idea." }, { "speaker": "Speaker 2", "text": "And we ran that for about 9 months and I got worn down and I brought it back. The thing we didn't have was an intelligence system that had all those signals that could help us make decisions. So it's" }, { "speaker": "Speaker 2", "text": "exciting to see this year." }, { "speaker": "Speaker 2", "text": "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." }, { "speaker": "Speaker 2", "text": "The VPs make most of the decisions." }, { "speaker": "Speaker 2", "text": "And there's founder mode, kind of flat." }, { "speaker": "Speaker 2", "text": "The founder makes a lot of decisions." }, { "speaker": "Speaker 2", "text": "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?" }, { "speaker": "Speaker 3", "text": "Well, I don't think the AI makes most of the decisions. I think that and Jack should correct me here. I think the AI helps with um communicating the alignment." }, { "speaker": "Speaker 3", "text": "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" }, { "speaker": "Speaker 3", "text": "combination of those variables. And the humans at the edges perform an incredibly valuable function of correcting and informing and sort of steering that. And I think one of the phrases that Jack has, which" }, { "speaker": "Speaker 3", "text": "I absolutely love and I've stolen so many times, is companies have multiple founding moments. Yeah." }, { "speaker": "Speaker 3", "text": "There's so many smart people in your company that have clever ideas that every day inflect the product, introduce something new. And so this idea that there's just, you know, one person who" }, { "speaker": "Speaker 3", "text": "is the brilliant person who comes up with everything. I just don't think, you know, I don't believe in hero worship or uh the converse of that where you you sort of scapegoat people. I think it's" }, { "speaker": "Speaker 3", "text": "harnessing the best of of your team to really advance the company. So I subscribe to the circle idea." }, { "speaker": "Speaker 1", "text": "Yeah, I I I also don't think the AI is making the majority of the decisions. I think it's facilitating Right. a more context-rich decision." }, { "speaker": "Speaker 1", "text": "I I think ultimately like in the most ideal case, our customers are actually making the majority of the decision decisions because they're just based on their queries and what they're trying to do with the system." }, { "speaker": "Speaker 1", "text": "Um delineates like where our road map should go. And then it's up 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." }, { "speaker": "Speaker 1", "text": "Um but we we just, you know, we weren't able to get to that level of data fidelity before. Um because we had to infer it. We had to do customer research. We had to do interviews. We" }, { "speaker": "Speaker 1", "text": "had to do um look at our customer support. Um You know, product feedback on on on Twitter, all these other things." }, { "speaker": "Speaker 1", "text": "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" }, { "speaker": "Speaker 1", "text": "actually want? Mhm. 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 to do that. And then I think all these things are going to" }, { "speaker": "Speaker 1", "text": "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 uh and optimism at in the same hour in" }, { "speaker": "Speaker 1", "text": "the same thought process of like what is a what is even a company going forward?" }, { "speaker": "Speaker 1", "text": "Like what like what are these structures going forward?" }, { "speaker": "Speaker 1", "text": "And this is the only like durable one structure that I could actually imagine lasting for quite some time. Yeah. Um and it was coming from a place of like, \"Wow, is our company just going to be" }, { "speaker": "Speaker 1", "text": "completely irrelevant Yeah. you know, in in the next coming years or or even even sooner? Like what do we what do we actually differentiate on?" }, { "speaker": "Speaker 1", "text": "What what do we have a a moat around?" }, { "speaker": "Speaker 1", "text": "And what what do we need to be to defend and and also to to grow that? Um And like what are the and all that follows from customer expectation. Like it the most amazing thing about Open" }, { "speaker": "Speaker 1", "text": "Core to me was that um people wanted to take this thing and contain it into a Mac mini and make it very tangibly theirs." }, { "speaker": "Speaker 1", "text": "Um and have all this agency around what they did with it. And we're seeing Square sellers do stuff with it like that." }, { "speaker": "Speaker 1", "text": "Interface with the the Square um APIs." }, { "speaker": "Speaker 1", "text": "And we're seeing Cash App customers. And and these are like not tech people. These are just like people I I want a I want a bot to help me manage my life. That agency independent of what your thoughts on" }, { "speaker": "Speaker 1", "text": "like how good of a system Open Core is right now, it'll get better and better." }, { "speaker": "Speaker 1", "text": "But the intent behind that is is agency." }, { "speaker": "Speaker 1", "text": "I want to tangibly control this intelligence and and for it to to better me and and what it makes possible for me is incredible. And and that expectation floor has just risen dramatically. And" }, { "speaker": "Speaker 1", "text": "and and that leads me again to like yeah, our our limiting factor as a company is our road map. Like we need to remove that from the equation. We need to ensure that our customers are truly" }, { "speaker": "Speaker 1", "text": "building alongside us. Mhm." }, { "speaker": "Speaker 1", "text": "And and that they, you know, are seeing us as a as a series of capabilities that makes their desires fast and easy and Yeah." }, { "speaker": "Speaker 1", "text": "and valuable. So like it it really goes back to the the capability set that we have." }, { "speaker": "Speaker 1", "text": "And then like the intuition of the interface that we have. And then like how intelligent our world models can can be to to be helpful and to compose UI in real time." }, { "speaker": "Speaker 2", "text": "Um I spent this morning at a company we call Rogo here in New York City. They read your article. Let's say you're advising the CEO of a 100-person company." }, { "speaker": "Speaker 2", "text": "They've already got their hierarchy." }, { "speaker": "Speaker 2", "text": "What should they do? Should they start with their system? Should they start with data? Should they start with their org? Like how should people go about, you know, running the Dorsey playbook?" }, { "speaker": "Speaker 3", "text": "Uh I don't know about this Dorsey playbook thing, but >> [laughter] >> um Well, we don't have it all figured out. I think there's an important dose of humility that we have that we really" }, { "speaker": "Speaker 1", "text": "bring on this path. We believe it's right, but we we know there's a lot to figure out. Yeah, it it's more like if if you were to at at 100 people or even, you know, just starting today, if you were to build" }, { "speaker": "Speaker 1", "text": "your company as an AGI, as an intelligence, what would it look like?" }, { "speaker": "Speaker 1", "text": "And what would you need uh 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" }, { "speaker": "Speaker 1", "text": "get things out to customers. I would be um in this like valley of dread about distribution Yeah. and attention because there is so much noise out there and it's so hard to get to the actual signal" }, { "speaker": "Speaker 1", "text": "of like who's building something interesting that will actually fundamentally change something and will be around for more than a year. Yeah. It it's like I think distribution really becomes a" }, { "speaker": "Speaker 1", "text": "differentiator. And I think there's some event horizon where the the way we think about distribution today closes off." }, { "speaker": "Speaker 1", "text": "You know, it like there's there's um the you know, apps for instance and websites and uh like the the traditional retail." }, { "speaker": "Speaker 1", "text": "There there's a number of things that will will change. And if you don't have the distribution today, it's going to be very hard to fight for that." }, { "speaker": "Speaker 1", "text": "But there'll be new areas of distribution that are probably more important. And I don't know what those look like." }, { "speaker": "Speaker 1", "text": "But I would say like I would I would assume that a company of 100 probably is no more than two to three layers deep, hopefully." }, { "speaker": "Speaker 1", "text": "Um And now would be the time to just like really question like do I do I need a hierarchy? Like Brian, a year into Square, I also we removed titles. We normalized everyone to lead." }, { "speaker": "Speaker 1", "text": "Yeah. We did it for like we were talking with all these banks all the time and you would have these EVPs and VPs and they were looking for the same on a business card. And there's this whole" }, { "speaker": "Speaker 1", "text": "business card culture. Yep. So we ripped up all the business cards. We we normalized down to a title of like you're a lead of what. And the longer that is behind lead is probably the farther down you are in the" }, { "speaker": "Speaker 1", "text": "organization. Um And we've kept it. Like we we, you know, we don't have titles. We we have like, you know, what do you lead? Um going back to like the DRI thing, what what are you ultimately responsible for?" }, { "speaker": "Speaker 1", "text": "And I I think it's helped us a lot. Um But this is an another step. Like it if if you're starting today or you're 100 today, like what what is actually fundamental to solving your your customer's problems" }, { "speaker": "Speaker 1", "text": "and and and where is the hierarchy getting in the way of that?" }, { "speaker": "Speaker 1", "text": "And look at all the tools you're using." }, { "speaker": "Speaker 1", "text": "Like look at all the information you're generating just by doing your work." }, { "speaker": "Speaker 1", "text": "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" }, { "speaker": "Speaker 1", "text": "relying upon on people telling you things." }, { "speaker": "Speaker 1", "text": "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." }, { "speaker": "Speaker 1", "text": "If imagine if your company was entirely legible." }, { "speaker": "Speaker 1", "text": "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 um useful and then making it proactive." }, { "speaker": "Speaker 1", "text": "Like that's that's the hardest bet is like we can determine causal getting to predictability for these world models around the company and and customer is is still right now a very much a" }, { "speaker": "Speaker 1", "text": "research but um but like it's it's one that you know it it's eminently solvable." }, { "speaker": "Speaker 2", "text": "Can you guys just take me behind the scenes? Like Jack this was a really bold move. You laid off 40% of your employees." }, { "speaker": "Speaker 2", "text": "Just like for CEOs listening what was that debate inside like how big it should it be how bold should it be?" }, { "speaker": "Speaker 2", "text": "You know Ruth Porat's got this good line if you're going to we can eat a [ __ ] sandwich don't nibble and you seem like you took a big bite." }, { "speaker": "Speaker 2", "text": "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? Yeah." }, { "speaker": "Speaker 1", "text": "So um it was something you know December of last year is when the is the when the models really got a uh like noticeable full upgrade from being able to be really good at building prototypes and greenfield efforts to" }, { "speaker": "Speaker 1", "text": "like understanding like large code bases and legacy code bases like our own." }, { "speaker": "Speaker 1", "text": "Um there was you know hallucination wasn't much of a topic in terms of like the the coding ability and the tool harnesses we became suddenly very mature. Like just in that month." }, { "speaker": "Speaker 1", "text": "And um it just like every everyone went home for the holidays and everyone played with these tools and they were surprised at how capable they were uh and what they could do with them and" }, { "speaker": "Speaker 1", "text": "you know we came back and the conversation was like just going around the table would would you build the company that this way if you had these tools today? Like what would the company look like? And" }, { "speaker": "Speaker 1", "text": "everyone around the table in my team just said like it would not look like this. It would not be this size. It would not be structured this way." }, { "speaker": "Speaker 1", "text": "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" }, { "speaker": "Speaker 1", "text": "all these like small things um but if we were to really reboot and rebuild the company like would we end up where we where we look today and the answer was uniformly no." }, { "speaker": "Speaker 1", "text": "Yeah. And 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%?" }, { "speaker": "Speaker 1", "text": "And then next what is the minimum number of people that we would need to um be to to uh fully um be in compliance with our regulators." }, { "speaker": "Speaker 1", "text": "Uh we're highly regulated business so that one's extremely important to us and legal obviously." }, { "speaker": "Speaker 1", "text": "And then third what is the minimal set of folks that we need in order to grow to fulfill our commitments we've made to the street but also rebuild the company as an intelligence and that's" }, { "speaker": "Speaker 1", "text": "roughly the number that we got to and we built in some buffer in case we made mistakes which we did and you know it hard hard not to um especially operating the way we have." }, { "speaker": "Speaker 1", "text": "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." }, { "speaker": "Speaker 1", "text": "But um it was it was that and and and that was a span of you know exploration to execution and and you know under under three weeks um and I I think generally I wanted to make sure that we" }, { "speaker": "Speaker 1", "text": "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" }, { "speaker": "Speaker 1", "text": "other companies will will probably get to this realization at some point. I don't want to react to that. I want to I want to um I want to be ahead of it because then we can do it with a lot more integrity. We can do it" }, { "speaker": "Speaker 1", "text": "with a lot more generosity for the people that we're asking to to leave um and even for the people that we're asking to stay and we're we're not just reacting into um something mediocre. We're we're you" }, { "speaker": "Speaker 1", "text": "know uh acting towards excellence and and like that's just the tone that we wanted to set. So um you know every every day it was just like constantly checking like are we doing the right thing? Is this" }, { "speaker": "Speaker 1", "text": "the right set of folks? Like um like what are we not thinking about?" }, { "speaker": "Speaker 1", "text": "What are we not talking about? And we you know we kept the the group very very tight." }, { "speaker": "Speaker 1", "text": "Um and had a conversation with with the board um which was uh my perspective very open to it and and actually more more than open more like yes we agree like we we should we should do this but" }, { "speaker": "Speaker 3", "text": "I'll I'll let Roelof speak to that." }, { "speaker": "Speaker 3", "text": "It was a very quick process. Okay. I think part of what helps is that Jack had written us a very detailed note laying out the logic. It's principled." }, { "speaker": "Speaker 3", "text": "It's not re- as Jack was saying it's not reactionary. It's very well laid out very logical." }, { "speaker": "Speaker 3", "text": "It was clear that the company and the management team was interested in the conversation about how to make this work um as opposed to being dogmatic and saying we have it all figured out. So" }, { "speaker": "Speaker 3", "text": "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 in" }, { "speaker": "Speaker 3", "text": "the first of those three weeks is different from where we in ultimately landed by the time the announcement took place." }, { "speaker": "Speaker 3", "text": "And also I think it's is the 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 short hands to" }, { "speaker": "Speaker 3", "text": "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." }, { "speaker": "Speaker 2", "text": "And the board was fully supportive." }, { "speaker": "Speaker 2", "text": "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 bringing in 100 employees? Should they start bringing in" }, { "speaker": "Speaker 2", "text": "independence? Should they like how do you build an amazing board that really serves the the company well the employees well the investors well the customers well. Like what's your advice on that?" }, { "speaker": "Speaker 1", "text": "I mean early on I always told myself and my team that like your your first board is your investors right? Um and uh I would treat that relationship as a hire you can never fire and in fact they can fire you" }, { "speaker": "Speaker 1", "text": "and I've been on the other side of that." }, { "speaker": "Speaker 1", "text": "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." }, { "speaker": "Speaker 1", "text": "Uh and and again they can fire you." }, { "speaker": "Speaker 1", "text": "And for me it was around you know I I think a lot of young founders kind of go for the brand names uh especially around VCs but I always uh wanted to go for the for the person um and you know that's why" }, { "speaker": "Speaker 1", "text": "uh Roelof um you know we we were we were optimizing for for him to be on our board and be an investor but like it was it was the fact that like he would uplevel our conversation uplevel our" }, { "speaker": "Speaker 1", "text": "execution more than anything else and challenge us along the way." }, { "speaker": "Speaker 1", "text": "Um so even as you think about adding independent board members like the the core function of a board is to ensure that the company has the right CEO. Like that's their one job." }, { "speaker": "Speaker 1", "text": "Um they have all these committee responsibilities and but the ultimate fiduciary duty is like do we have the right CEO going forward?" }, { "speaker": "Speaker 1", "text": "And I think you have to build a board that has different perspective on that." }, { "speaker": "Speaker 1", "text": "Um and that is open to wild ideas that things that are going to just seem like crazy uh in the moment which like this one might might be." }, { "speaker": "Speaker 1", "text": "Um but it can be rationalized if we talk through it and we like really document it and paint a picture of like where the where this could go and like what the opportunity cost is if we don't" }, { "speaker": "Speaker 1", "text": "do something um because like if we didn't do something like this I just imagine like every year it's a 10% riff or 20% riff or whatever it is and like that is just the most demoralizing" }, { "speaker": "Speaker 1", "text": "like crappy like non-creative building of a company ever. And it's all you know with your backs against the wall and like it just feels like losing constantly. Um and I you know I had a conversation with the" }, { "speaker": "Speaker 1", "text": "board about I don't want that. Like that's not I don't want to be at a company like that. Like it it's just it doesn't make sense. It's soul-crushing you know and it's just not not inspiring and I I feel" }, { "speaker": "Speaker 1", "text": "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." }, { "speaker": "Speaker 2", "text": "Well, Jack, you're on a lot of boards." }, { "speaker": "Speaker 2", "text": "You're on some really good ones." }, { "speaker": "Speaker 2", "text": "Advice for CEOs how to build a board." }, { "speaker": "Speaker 3", "text": ">> [snorts] >> 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." }, { "speaker": "Speaker 3", "text": "Not a financing decision." }, { "speaker": "Speaker 3", "text": "Cuz they'll have a much bigger bearing on the ultimate outcome of your company." }, { "speaker": "Speaker 3", "text": "And then I'm generally a fan of getting a very good independent board member within a year or two. Okay. Uh certainly by the time you get product market fit." }, { "speaker": "Speaker 3", "text": "And I think there's a 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" }, { "speaker": "Speaker 3", "text": "come to the conclusion that the founder is no longer the right person to run the company, maybe rightly, maybe wrongly." }, { "speaker": "Speaker 3", "text": "Um 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" }, { "speaker": "Speaker 3", "text": "fantastic mental relationship to help the founder on that journey depending obviously on their level of experience." }, { "speaker": "Speaker 3", "text": "Um I think boards are often built too late in a rush, especially in the run-up to an IPO where people suddenly realize, \"Ooh, I've got a four-person board and I need nine.\" or whatever the case is. And" }, { "speaker": "Speaker 3", "text": "then you suddenly assemble people who have no context, they have no history, and they have no chemistry. Cuz you will be tested." }, { "speaker": "Speaker 3", "text": "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 uh activist investor or a tricky financing, you know, that really" }, { "speaker": "Speaker 3", "text": "test the metal 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" }, { "speaker": "Speaker 3", "text": "just think it's one of those things that requires a lot more care than I think most people apply to it. Yeah." }, { "speaker": "Speaker 2", "text": "Jack, you you've started couple great companies here. You're kind of startup founder." }, { "speaker": "Speaker 3", "text": "Scale-up CEO. Uh Brian, he he he was uh the only person to have founded two companies that made it into the S&P 500." }, { "speaker": "Speaker 3", "text": ">> amazing. And the only person to have been simultaneously CEO of two public companies. Okay, Jack. Just for the record. Then this >> Which should not be should not be a goal for anyone, by the" }, { "speaker": "Speaker 1", "text": ">> [laughter] >> Recommend he CEO of two companies?" }, { "speaker": "Speaker 1", "text": "Is it ever a good idea?" }, { "speaker": "Speaker 1", "text": "Not public companies. Yeah. Private, maybe. Private private I would I would I I think there's probably going to be more of a trend where people are leading multiple companies that are private, but public companies" }, { "speaker": "Speaker 2", "text": "like I should be like an anti-goal. It's an anti-pattern. What can founder CEOs learn from like what did you do right?" }, { "speaker": "Speaker 2", "text": "What did you just get wrong? What advice do you have for that 100-person company CEO Yeah, what do you got?" }, { "speaker": "Speaker 1", "text": "My only regrets in life and and also in our in our businesses um are where I decided not to learn something." }, { "speaker": "Speaker 1", "text": "Okay." }, { "speaker": "Speaker 1", "text": "Because I like I I embrace all of our mistakes and all of the bad decisions we made, but like if I'm not learning from that uh actively learning from it, like that's that's what I regret." }, { "speaker": "Speaker 1", "text": "And um you know, in in in in probably the worst case in any of these companies um like just delegating way too much. Yeah." }, { "speaker": "Speaker 1", "text": "Um especially especially within Block because like I wanted to set a structure where we had multiple CEOs in this company, but I realized, \"Oh man, we're we're just building like a holding" }, { "speaker": "Speaker 1", "text": "company now.\" Yeah. And like we got 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" }, { "speaker": "Speaker 1", "text": "growing at different clips. It's how do we bring them together and like, you know, really, you know, um challenge the whole financial network in entirely because we have we both sides" }, { "speaker": "Speaker 1", "text": "of the counter. So like why aren't we structured that way? Mhm." }, { "speaker": "Speaker 1", "text": "And that I think led to just very differing cultures and values and execution levels and um that was a mess. So I I think the the one thing that I I probably consistently would have corrected would be just" }, { "speaker": "Speaker 1", "text": "delegating too much, you know, too too uh too much of that and I didn't learn that fast enough. Like that's that's the regret is I didn't choose to to learn from that fast enough." }, { "speaker": "Speaker 1", "text": "Um but when you have your whole your whole your entire company is legible, it's a very different equation. Mhm. Um and I think my regrets going forward if I were to predict them would be like am I" }, { "speaker": "Speaker 1", "text": "actually putting enough entropy into the system like enough of the intent into the system to actually keep us relevant going forward. Um and and that's hence the shift. Like I I I can't imagine doing anything bigger" }, { "speaker": "Speaker 1", "text": "than rebuilding our company as an intelligence um or more correct uh given where where everything is trending." }, { "speaker": "Speaker 1", "text": "So it just it feels like I have to constantly build uh and constantly learn from whatever we're putting out there in order for our us to stay relevant um going forward." }, { "speaker": "Speaker 3", "text": "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." }, { "speaker": "Speaker 1", "text": "And what's the color? What what are the nature of the meetings today versus what they were a year ago? Well, I mean just two months ago uh every meeting that we would have with a company I mean you you" }, { "speaker": "Speaker 1", "text": "have this Brian like you see a presentation or Google Doc and we go through it. Yeah." }, { "speaker": "Speaker 1", "text": "Now um everyone is bringing a prototype that they built. Yeah. Which is pretty amazing. And like it's either simulated data or real data." }, { "speaker": "Speaker 1", "text": "But it's a cut on their work in a way that's far more um has far more depth and and realism than we could ever get from a slide deck." }, { "speaker": "Speaker 1", "text": "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. Mhm. Um so like the the breadth that we get to" }, { "speaker": "Speaker 1", "text": "explore is suddenly in 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" }, { "speaker": "Speaker 1", "text": "horizontal." }, { "speaker": "Speaker 1", "text": "Where do we want to go like deep? And like what what is the right path?" }, { "speaker": "Speaker 1", "text": "And and the cost of like being wrong on that path and going back up the tree and going down another path is getting closer and closer to zero because the tools can explore the path so quickly" }, { "speaker": "Speaker 1", "text": "and then also we can go down them much much faster." }, { "speaker": "Speaker 2", "text": "I I I I completely agree with you. Like a lot of times in the past history what worked was when we were doing a lot of different stuff and we were distracted." }, { "speaker": "Speaker 2", "text": "It's like let's just get focused and then we made progress." }, { "speaker": "Speaker 2", "text": "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. What do you ever have" }, { "speaker": "Speaker 1", "text": "either of you have a reaction to that?" }, { "speaker": "Speaker 1", "text": "Yeah, it's uh I think it's I think it's having a wider perspective to start and then like because in in the past uh if we were to explore different paths like it would be a uh you know, three it'd be a very costly" }, { "speaker": "Speaker 1", "text": "exercise, especially with in hardware for instance. Take you a long time to build that prototype. But today we can do it in an hour. Yeah. And then um so I I do encourage more exploration." }, { "speaker": "Speaker 1", "text": "But I think focus on getting the the details right when we do choose that path and like it's the 80/20 percent thing, which is like you know, these tools will build about 80% of what where we need to go. Yeah." }, { "speaker": "Speaker 1", "text": "And then that last 20% is going to be a function of like how good our creativity, how good our taste is, how good our judgment is. Yeah. And um and just constantly pushing these these" }, { "speaker": "Speaker 1", "text": "models to to doing something they weren't they weren't we didn't think they were capable of. And that's where I think the magic still happens and where where I think the the focus still" }, { "speaker": "Speaker 1", "text": "comes to bear. Um because at at the end of the day you have to right now you have to pick something to put out there because we do have a roadmap. But when you remove that limiting factor as I" }, { "speaker": "Speaker 1", "text": "said and you focus on building the four things instead like, you know, the capabilities, the interface, proactive intelligence, and the world model, then, you know, it just changes everything. So" }, { "speaker": "Speaker 2", "text": "I don't even know if the question matters anymore. Yeah. A lot of CEOs are struggling with the second acts. And you've done amazing second act work at Block. You did interesting stuff with" }, { "speaker": "Speaker 2", "text": "Blue Sky, interesting stuff with Spiral." }, { "speaker": "Speaker 1", "text": "Advice to CEOs trying to figure that second act out. Uh I don't know if I ever considered it to be like a second act. It's just something that like we had I wanted to do and I had to do and" }, { "speaker": "Speaker 1", "text": "it was interesting. Are you building something new? It's distracting to the org and like how do you resource it?" }, { "speaker": "Speaker 1", "text": "Well, Cash App was like that in the early days. Yeah. Well, that that's that's a good point. Like so I think every leader has to be comfortable with losing credibility with their stakeholders. That's the point. In" }, { "speaker": "Speaker 1", "text": "order to do something interesting like when when we we had multiple moments and these are the founding moments that um I think are are critical for a company, but like we were we started with our card reader." }, { "speaker": "Speaker 1", "text": "Eventually we determined that, \"Hey, we should probably lend money to sellers because like no seller wants to accept credit cards." }, { "speaker": "Speaker 1", "text": "What they want is to um get more sales." }, { "speaker": "Speaker 1", "text": "And what helps them get more sales? More capital to deploy into their business.\"" }, { "speaker": "Speaker 1", "text": "When we first brought it to our board, um our board said, \"Absolutely no. Like you're not getting in the lending business. Like it's ridiculous.\"" }, { "speaker": "Speaker 1", "text": "And we lost I lost some credibility with with um you know, the board and our population cuz we wanted to do this and we kept pushing it and pushing it and eventually they said yes. Cash App was the same" }, { "speaker": "Speaker 1", "text": "thing where we were about merchants. Our mission was make commerce easy. Mhm. And we built this thing that allowed effortless peer-to-peer as effortless as just, you know, sending an email to" }, { "speaker": "Speaker 1", "text": "start. And our our our our COO at the time was on the founding team of PayPal, Roelof or Keith Rabois. Yeah. And even he said no and he said like, you know, this is a solved problem." }, { "speaker": "Speaker 1", "text": "Everyone in the company hated Cash App." }, { "speaker": "Speaker 1", "text": "It was a team of eight people." }, { "speaker": "Speaker 1", "text": "And hated it for two to three years that we we mentioned it less than eight times in our S-1 to to go public. Um our investors didn't understand it at all." }, { "speaker": "Speaker 1", "text": "And every day that I allowed it to persist and defended it, I lost credibility." }, { "speaker": "Speaker 1", "text": "And I knew that I could earn it back if it if we saw success there and we did." }, { "speaker": "Speaker 1", "text": "Like we we monetized it and it became profitable and, you know, it's now over half our business and um so it I think it's getting comfortable with like you're going to lose credibility and if" }, { "speaker": "Speaker 1", "text": "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" }, { "speaker": "Speaker 1", "text": "you're okay with, yep, 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 is why I believe it. I think it makes all those" }, { "speaker": "Speaker 2", "text": "answers stronger, by the way. I have a a weird story for you. When Sequoia was hiring me, they write a memo when they're investing in a company or when they're hiring someone and the memo on" }, { "speaker": "Speaker 2", "text": "me was one of my strengths was I was DGAF, don't give a flock, and one of my weaknesses was I was DGAF, I don't give a flock. Um you strike me as someone who's has high DGAF and you stick with your convictions for" }, { "speaker": "Speaker 2", "text": "very long periods of time. Founders struggle with that. I struggle with that. Advice." }, { "speaker": "Speaker 1", "text": "Yeah." }, { "speaker": "Speaker 1", "text": "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 I made a I made a decision some time" }, { "speaker": "Speaker 1", "text": "ago when I first became CEO of Twitter." }, { "speaker": "Speaker 1", "text": "Everyone was telling me I needed a uh CEO coach. Mhm. And I got the CEO coach and he was a great guy, but like I was learning absolutely nothing. Mhm." }, { "speaker": "Speaker 1", "text": "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." }, { "speaker": "Speaker 1", "text": "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. Mhm. To to for it to" }, { "speaker": "Speaker 1", "text": "be a mentor, I have to decide that I'm going to learn something from it. Like every every every encounter I have is trying to teach me something and what am I trying to learn from it. And just I" }, { "speaker": "Speaker 1", "text": "would force myself to like write it down like every day and every encounter and just like, what did I learn from this?" }, { "speaker": "Speaker 1", "text": "And again, my biggest regrets are when I decided not to learn something from it." }, { "speaker": "Speaker 1", "text": "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" }, { "speaker": "Speaker 1", "text": "from this or not? And that allows you ownership over it. Like it just like it gives you agency over all this stuff." }, { "speaker": "Speaker 1", "text": "Like, what is this thing trying to tell me right now? Like what am I ignoring?" }, { "speaker": "Speaker 1", "text": "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" }, { "speaker": "Speaker 1", "text": "instead of having this one mentor in your life, now you have infinite mentors. It's like, you know, it's it's uh it's just an amazing way to approach life and challenges that that I" }, { "speaker": "Speaker 2", "text": "found." }, { "speaker": "Speaker 2", "text": "You're definitely a learner and talk a lot about it on other I've seen you talk about it a lot. You're a meditator." }, { "speaker": "Speaker 2", "text": "Should all CEOs meditate? Um what are the benefits you get as a CEO?" }, { "speaker": "Speaker 2", "text": "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" }, { "speaker": "Speaker 2", "text": "you get from it?" }, { "speaker": "Speaker 2", "text": "Yeah." }, { "speaker": "Speaker 1", "text": "Him him saying that he's not introspective is very introspective, I think. I thought that was interesting." }, { "speaker": "Speaker 1", "text": "Just to be clear." }, { "speaker": "Speaker 1", "text": "Um I don't I didn't get a lot from that, but I I do think um the when people think of meditation, they think of like this woo-woo like, you know, person in the desert and uh I've been characterized as that and" }, { "speaker": "Speaker 1", "text": "looking at the clouds and like imagine the clouds going by and your thoughts are the clouds and you know, make them dissipate. But if you actually get into like true meditation, it's a very" }, { "speaker": "Speaker 1", "text": "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" }, { "speaker": "Speaker 1", "text": "days and you spend the first 3 days sitting from 4:30 in the morning till 9:00 p.m. Yep. focusing on the feeling of your breath on your upper lip. Yep." }, { "speaker": "Speaker 1", "text": "Just that and just the sensation of it." }, { "speaker": "Speaker 1", "text": "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 intellectual standpoint. Mhm." }, { "speaker": "Speaker 1", "text": "And then the next 7 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 3 hours at a time. Mhm." }, { "speaker": "Speaker 1", "text": "And it's super painful. And you actually observe this pain and you're just like you're you're constantly with this mindset of like, this isn't permanent." }, { "speaker": "Speaker 1", "text": "If I were to stand up, it goes away." }, { "speaker": "Speaker 1", "text": "Mhm. 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. Mhm." }, { "speaker": "Speaker 1", "text": ">> Like you and you're doing it in this very small physical way, but then you apply that whole concept to your to your whole life, every emotion or reaction or en- encounter you have. So I" }, { "speaker": "Speaker 1", "text": "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" }, { "speaker": "Speaker 1", "text": "then choose how you want to act with that information. Mhm. 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." }, { "speaker": "Speaker 1", "text": "If you see it as a physical practice to make your mind stronger, Mhm. you'll get that and and that's that's what I see and that's what you practice. Mhm." }, { "speaker": "Speaker 2", "text": "Let me just close on I start with you, Roelof. There's some timeless qualities of CEOs um that last the test of time and Roelof, you're involved with YouTube, Instagram, Block, [ __ ] Unity. What are timeless" }, { "speaker": "Speaker 2", "text": "CEO qualities?" }, { "speaker": "Speaker 2", "text": "And what is new? Like what are the new qualities CEOs need today?" }, { "speaker": "Speaker 3", "text": "I like acronyms, so I came up with one which is um ALE." }, { "speaker": "Speaker 3", "text": "Mhm. A L E. Which is sort of not a very pleasant drink for most people, but anyway, um authenticity, logic and empathy." }, { "speaker": "Speaker 3", "text": "So authenticity, I mean, are you, you know, are are you pretentious? Are you who you Do people see who you really are? Do you behave authentically?" }, { "speaker": "Speaker 3", "text": "Are you logical? Are you predictable?" }, { "speaker": "Speaker 3", "text": "Are you rational? Or do you fly off the handle?" }, { "speaker": "Speaker 3", "text": "Uh and are you empathetic? Do you really care about the team that you manage? Do you really care about the business?" }, { "speaker": "Speaker 3", "text": ">> Weird. Uh or 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," }, { "speaker": "Speaker 3", "text": "I think it's just hard to keep it in your mind. So for me, those are the three most important, authenticity, logic and empathy." }, { "speaker": "Speaker 3", "text": "I think when it comes to dealing with humans, most of those things stay the same." }, { "speaker": "Speaker 3", "text": "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" }, { "speaker": "Speaker 3", "text": "largely the way they were before. Mhm." }, { "speaker": "Speaker 3", "text": "But I think the same is true here. Yes, companies are being built differently." }, { "speaker": "Speaker 3", "text": "Yes, AI is absolutely transformational." }, { "speaker": "Speaker 3", "text": "It's going to upend so many industries." }, { "speaker": "Speaker 3", "text": "I think it's the biggest drainer of moats companies have ever seen." }, { "speaker": "Speaker 3", "text": "But some of the, you know, basics of dealing with people uh and leading remain true." }, { "speaker": "Speaker 3", "text": ">> Mhm. The one I would say is probably different is the pace of of change is so fast." }, { "speaker": "Speaker 3", "text": ">> Mhm." }, { "speaker": "Speaker 3", "text": "And I think, you know, kudos again to Jack for the the the speed with which we're moving on this decision cuz it would have been easy to dither for 6 or 12 months on this decision. Mhm. So" }, { "speaker": "Speaker 2", "text": "you've got to move fast. Mhm. Jack, thoughts on that?" }, { "speaker": "Speaker 2", "text": "Like you're you've hired some amazing people in your career that have gone on to do some amazing stuff." }, { "speaker": "Speaker 2", "text": "What do you What do you think? And what's changed What's What's timeless?" }, { "speaker": "Speaker 1", "text": "What's changed?" }, { "speaker": "Speaker 1", "text": "I value someone who's able to reprogram their mind and assumptions constantly." }, { "speaker": "Speaker 1", "text": ">> Mhm. Um I mean, this is stated a lot, but just being able to question your own requirements, your own assumptions and your own decisions Mhm. or how rigid you are towards your past, the company's" }, { "speaker": "Speaker 1", "text": "past and sacred cows or what the competition is doing. Mhm. Um it's just, you know, being able to like go wild for a bit and then also being able to get that entire corpus down to something" }, { "speaker": "Speaker 1", "text": "that's actually manageable and that can be articulated in a way that other people understand." }, { "speaker": "Speaker 2", "text": "I think that's extremely valuable. Has it been valuable or is more valuable cuz things are moving so fast right now? I think it's more valuable. Like it being able Yeah, I mean, I think it's going to be so easy to go" }, { "speaker": "Speaker 1", "text": "along with the momentum of what's happening around us today." }, { "speaker": "Speaker 1", "text": "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" }, { "speaker": "Speaker 1", "text": "intelligence to intelligences Yeah. and people will go along with uh more likely to to default to what these things are suggesting Mhm. rather than seeing them as an input. Like I I think we're we're" }, { "speaker": "Speaker 1", "text": "still in a 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. Mhm. And I like I think" }, { "speaker": "Speaker 1", "text": "that's important to me like when I was doing that like every day 3 hours like this is input to me. Mhm. And it's now up to me to like really um make better output from like all this" }, { "speaker": "Speaker 1", "text": "new input that I have and like the ability to just take all this and see it at once it is just phenomenal. Mhm. So having someone who's able to discern signal from noise and cool from not relevant, you know, like" }, { "speaker": "Speaker 1", "text": "there's there's this is highly overused right now but um the the taste thing is real Mhm. and it's it's not just like I know what things look good together." }, { "speaker": "Speaker 1", "text": "It's more like do I have a point of view?" }, { "speaker": "Speaker 1", "text": "Mhm. 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?" }, { "speaker": "Speaker 1", "text": "Mhm. And I think that's that's critical." }, { "speaker": "Speaker 1", "text": "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. Mhm. And and because it didn't exist is why I'm building it. And I" }, { "speaker": "Speaker 1", "text": "think um right now you're seeing a lot of companies they're just copies of copies of copies of copies because it's easy. Yeah. Instead of like what's your what's your point of view?" }, { "speaker": "Speaker 1", "text": "Like what is what is opinionated in this and like where where is it pushing the the boundaries and where is it uncomfortable? Mhm." }, { "speaker": "Speaker 2", "text": "I think that's brilliant. It's a great place to end. Thank you both for coming on Long Strange Trip. I love the article you wrote. I think it's going to be game-changing for lots of companies." }, { "speaker": "Speaker 2", "text": "Appreciate you both." }, { "speaker": "Speaker 3", "text": "Thank you." }, { "speaker": "Speaker 2", "text": ">> Thank you, Ryan. Thank Jack. Thank you." }, { "speaker": "Speaker 2", "text": "Hope you liked that. I really enjoyed speaking to him. He's an unusual Homo Sapien and he's got some interesting thoughts." }, { "speaker": "Speaker 2", "text": "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" }, { "speaker": "Speaker 2", "text": "thing is going to happen. And I 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." }, { "speaker": "Speaker 2", "text": "Um the power rested in the VPs essentially." }, { "speaker": "Speaker 2", "text": "Um when I ran HubSpot they didn't call it founder mode then but it was kind of founder mode. Instead of being a pyramid it was flat and a lot of power was rested in the in the founder's hands." }, { "speaker": "Speaker 2", "text": "Um He's sort of proposing the Dorsey mode in my mind. He laughed about it when I said it but I think of his like what's next." }, { "speaker": "Speaker 2", "text": "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" }, { "speaker": "Speaker 2", "text": "customers 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 making a lot of the decisions that a hierarchy used to." }, { "speaker": "Speaker 2", "text": "I think he's onto something. I'm curious to see what you think. Um comment on Twitter or comment in on YouTube. I'm I'm curious about your thoughts on it. I think Jack would be curious too. He's" }, { "speaker": "Speaker 2", "text": "[music] 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." } ]