The Exchanges

Q And then I just had Torsen Real who's the founder of Helsing who it has, it's not out yet, but he's just like, he said, I think started the conversation. Cause his whole thing is like, Europe needs its own way to defend itself. This is not a fucking business. This is a mission. He goes, we're not selling this for any amount of money. What's your opinion on this?

A Look, you said it. It's what are you solving for? Are you solving for the mission? Are you solving for a paycheck? I think you could probably guess based on where I come from that I'm not solving for a paycheck, right? And the way I talk about the business and the way we act and the way the business is run, we're here to achieve a mission. That mission is kind of never ending, right? Human prosperity, energy, abundance, affordable, reliable power. We're never like, well, we did it. Like we, we did the affordable, reliable power thing. Like what's, what's next, right? Like that will, that is a mission that will live on forever. Probably I'll outlive the company, outlive me. Hopefully the company outlives me. And then, and then the mission will go on forever. And eventually You know, either, either, you know, the, the, um, something will take out the earth that will kill the company. Right.

AI assessment note: “It's what are you solving for? Are you solving for the mission?”

Q You're talking about putting obese women on, like, the front of a magazine?

A Uh, yes, like, um, like, the Victoria's Secret had this phase of, like, obese women and men! Men! Victor's Secret! This isn't Victor's secret, but it was for a while. Like, why, why are we all pretending? It was like the emperor's new clothes, the emperor's new lingerie. Like, we're all pretending that this is still sexy, and we're pretending that this still looks good. Anyway, going off of the back of that, people are allowed now to say, this is more beautiful than this, and a beautiful building is more beautiful than an ugly building, and a beautiful website is worth creating. This is what Joe Jebbia and the National Design Studio team are doing is, Saying, we believe that more beautiful experiences on the internet reflect the dignity of being an American citizen, and that is what we want, so we're going to put in effort from the best talent in the private sector to go make that for you because it's worth something. We're not going to pretend that a website has to be ugly. And anything big or small or glamorous or very pedestrian, like a simple government website, can be made more beautiful. And when it is, people appreciate it so much more because we do have this inherent Yearning for beauty. And going back to real versus fake things, the fake things don't have beauty. They're orphans in a way. Nobody loves them.

AI assessment note: “Uh, yes, like, um, like, the Victoria's Secret had this phase”

Q How does it help you know yourself better?

A Well, that's not why I did it. Ok. I don't think I know myself better, but I, I feel more expansive now that, that there's more than I thought I knew. Like, um, here's how I kind of thought about it afterwards. Um, You have to picture an old car radio from maybe like the fifties or something, you know, like an old pickup truck had a car radio with a needle, and you could move, you know, move the dial and the needle moves, right? Get the little glass window with all the channels. And you're, you're in one of the channels. That's where you are all the time. You're in this channel. 95.7 is, is, is you. And psychedelics, like, let me turn the knob a little bit and tune into something else that's always been there. But I couldn't, I couldn't hear that frequency. Like, it's amazing. And then you're like, I, if you look at a radio and you turn the knob, you're picking up things that are there that you can't hear until you turn the knob. That's what it was like for me. And how does it make me a better whatever or know myself better? I think all experiences help you know yourself better. So it's just a mirror and a reflection and a, and a detail and a, and a, and a, and a crumb that creates the pile of you. I don't really know. It's not like that was a huge breakthrough for me, but it was fascinating. Enough to do it a few more times and learn a few more things that were just fascinatin…

AI assessment note: “I don't think I know myself better, but I, I feel more expansive”

Q Right, so you buy the yellow Lambo. But more interesting than the yellow Lambo to me is what you said, where you said that The, what Bezos did, what Jeff Bezos did for you and Jason was gave you the confidence to go for it. Can you explain that?

A So in the early days of Thursday, we had launched Basecamp, it was taking off quite well, and we got a lot of interest and outreach from VCs. We counted 40 some at the time, and this was 2005 ish. I still had very vivid memory of the dotcom boom and bust. I had seen what happened to some of these VC funded companies and the internal mechanics of that, and I didn't like any of it. And I also had all these ideas about efficient businesses and what it takes to run. So we didn't actually want VCs, but Going back to this point about trusting yourself. I didn't fully trust myself not to get tempted by a twenty million dollar check, a fifty million dollar check, whatever the number was at a time where my bank account said, I don't know, 8000 dollars. Funny thing. My bank account did say highly, uh, slightly higher than that. When I came to the US, I think I had like, 50 grand that we had worked up as we started Basecamp. And the first thing I did as soon as I landed was Jason took me to an Audi dealership and I bought an Audi S for my first car cash. And then there was basically all the money I had in my bank account. So I just blew it all on the car and I thought like, we're going to make it back. But, um, This, this notion that we had something that was taking off, but this is all fleeting. I had great humility that like, I'd seen many other businesses, oh, it's popping off, and the…

AI assessment note: “we didn't actually want VCs, but Going back to this point about trusting yourself”

Q rebuilding from scratch. It's the same platform that more than 300 startups who have grown to over a billion dollars in valuation grew their businesses on. And now HubSpot for Startups offers this service at up to a 90% discount exclusively for eligible startups. Visit HubSpot.com forward slash startups to learn more. That is HubSpot.com forward slash startups. Have you had a chance to nerd snipe him back since then?

A Yes, on Linux. So I switched to Linux about two and a half years ago, and first I had this, uh, soft on-ramp as most people switch to Linux. I used Ubuntu. That's the most popular Linux distribution. That's fine. I mean, actually it's great in many ways because Linux has all these different distributions. They have Ubuntu and Fedora and Red Hat and whatever, but it's all the Linux kernel, like the magic of Linux Linux is the Linux kernel and then the ecosystem of all these tools that are around it. And whether you package them in this one way or package them in this other way is not the make or break of it. So just getting into Linux for me was a huge thing. I'd been on the Mac for well over 20 years. I was completely a Mac head as in thinking this is a Mac is computer. Like I don't want to use another computer. Windows certainly is not for me. I don't know. Linux is for people who like pocket protectors and just The kind of nerd that I can relate to, I can respect, but it was not a me thing. Then finally, Apple pissed me off enough that I thought I cannot in good conscience continue to spend money on their products if I have such deep disagreements with how they run the company. So fine, I'm going to try something else. And as I said, I gave Windows two weeks and I realized, man, shit, I can't do it. I'm going to come crawling back to the Mac if there's not something else. But…

AI assessment note: “Yes, on Linux. So I switched to Linux about two and a half years ago”

Q I've heard you talk about developing this like last mile logistics network. Did you think about that back then? Or you're just like, hey, I'm just going to try to expand the market for food delivery?

A No, we did. So the, when we started, um, I guess to take a step back before we shipped Palo AltoDelivery.com or even how we got there, You know, my co-founders and I really got connected because of an interest in small businesses. You know, I think my story I've told publicly, which is really, I mean, I grew up, ah, coming as, to the States as an immigrant from China, and my mom, um, you know, put food on the table by working three jobs a day for 12 years. One of those jobs happened to be at a Chinese restaurant where she was a waitress. I got to hang out with her, wash a few dishes when she allowed me to. That's kind of how I grew up while my dad was getting his PhD at the University of Illinois. That was, you know, the first 10 years or so of childhood growing up in the States, and that moment and experience always just gave me a deep appreciation for what small business owners represent. I mean, to them, there's no such thing as work. Work, life, it's all the same thing. There's no concept of a weekend or a Saturday. It's Saturdays and Tuesdays are exactly the same days, and you just kind of get into this process where That becomes your identity, and it's actually one of the most fascinating things I find about the great experiment that's America where, you know, because it becomes this all-consuming thing, one of the nice positive derivatives is actually they don't just cre…

AI assessment note: “No, we did. So the, when we started”

Q Wait, what did you mean by the five words you say at the beginning of a sentence?

A I used to go, again, engineer. Um, that's always, like, an interesting experience with, um, uh, four other engineers working for me and, um, like, I, I stay pretty current. Um, uh, with engineering, I still do not a ton of production, uh, um, production engineering, but like I do, um, I, I sometimes start new projects with people like, uh, and, and the first 20, 30 pull requests or commits in many repositories for things that we use, uh, come from me. So like, I, I like doing this. It's, it's part fun, part, I, I sometimes need to tap into my craft. Um, anyway, um, so that's a surprising thing for people, um, uh, of course. So my intuition was always like, okay, well, this is not the right architecture for this kind of thing. And I know this for a fact because I've built this thing before. So let me go to a right, um, uh, whiteboard and just like re-architect this. And like, and so at some point, um, and that like now, you know, Daniel, my co-founder, like, explained to me, well, look, you get, you're pretty defensive then, because they just came to show you basically, you know, what was objectively their best work, because they presented it to you, and that matters to them, so, and then you just, like, it doesn't matter if you go and make a much better system here, on top of the head, um, they are like, um, if I truly ever did this, um, They're gonna be defensive and try to sa…

AI assessment note: “just put, for example, in front of every sentence”

Q I did, well, one, the next day I log into my email, and it's just whoosh all the way down. Just like, no, no, no, no, no, no. But that is such an unusual instinct. If I'm being honest, like, I don't think I would have done that. What the hell is going on there? You didn't see it as a competition. You didn't, what, what was, what was happening?

A The first thing that flashes to my head is, you know, in my show, I've always asked people the same question at the end of what's the kindest thing anyone's ever done for you. Some person on Twitter or something went and compiled every answer, there's 500 answers or whatever, and categorized them and like made a pie chart of like what people say, and something like two-thirds of the answer to this question were the same, which was the kindest thing was some person made a bet on me, the person answering the question, before I deserved it, or like they saw something in me that maybe I didn't even see in myself. They, they bet on me before others would. And that was the answer to the, the kindest thing. And when I was 26, I, I became very interested in, ah, all of the, I studied philosophy early in life, and I've always been interested, interested in that stuff. But I became really interested in the religious texts, like all the world's religious texts. And I was, I was kind of, ah, I was in a weird spot in life. I kind of hadn't found anything to do yet. I wasn't that good at anything. And I was searching. I was always searching for like, what the hell should I do? What the hell's the point of all this? And I found this passage in the Upanishads, which as a book is probably the most important book to me. And the Upanishads is this collection of stories from many thousands of year…

AI assessment note: “The first thing that flashes to my head is”

Q the first time there was gonna be all these, like, crazy colors and everything else, like, and Johnny tells the story, he's like, you know how we chose the colors? He's like, me and Steve went to the design, like, where, the Apple Design Center, and we talked about it, and 30 minutes later, the colors you saw, we shipped. That was it. Where are you on, like, that spectrum?

A Yeah, I think the most important thing that, uh, you described is it's a spectrum. It's not a hundred percent, um, you know, one way or the other way, because again, sort of like, I remember early on, um, you know, people talking about that sort of dichotomy of how Google does things and how Apple does things, and many founders then tended to gravitate when Apple was at sort of peak Steve Jobs to, no, I run the product review, it's only my opinion that matters, um, and it's my taste, and I've got this articulation, all these things. And lo and behold, like, uh, some terrible decisions, uh, ended up, uh, coming out of this, et cetera. And, and I think where people, um, sort of break down on almost all issues is they take it literally. I don't believe for a second that Apple was a hundred percent in the camp where Steve Jobs just had universally the answer to everything. He didn't listen to anyone else's opinions. He didn't try things out. Sometimes maybe trying it out by testing his ideas on multiple people inside and outside, um, you know, et cetera. But of course he did that. Right. And I know one of the ways he did it, which was brilliant and that don't get talked about. He actually called up journalists. Sometimes, and tested ideas on them, and, and like, we might do this, um, kind of thing, and then hear the journalists react to it, and it's like, okay, that was a bad idea,…

AI assessment note: “it's a spectrum. It's not a hundred percent, um, you know, one way”

Q Can you like talk us through that time of your life?

A I just had a lot of confidence. I think, I think a lot of entrepreneurs Not that we weren't making mistakes. I just, I think entrepreneurs believe, okay, I, I got this from listening to the Michael Dell one on the drive out here, in fact, is that Michael said, well, you, you gotta make mistakes. That's how you learn. That's how you, you iterate. Entrepreneurs have confidence that they will solve the problems. Michael likes to figure out puzzles, right? Well, business in some ways is a puzzle. It's like, And I'm doing it again with Love Life. It's like, okay, what does the market really want here? And, okay, this isn't working. We've got to do less of that. This is working. Let's do more of that. And then, and then you, you're constantly trying to think about how to create more value for your customers in ways that they don't necessarily even know they need it. So the entrepreneur has confidence that he or she will figure it out, crack the code, solve the puzzle, and So they're willing to go ahead, even though they don't know for certain, because they're, what they do believe is they're figuring it out. They're going to figure it out. And, um, people that my, I think my co-founders, they weren't sure we would be able to figure it out. So they, and they didn't want to blow it. They didn't, they want to play it safe. They didn't want to lose what they had, I think. And I was like,…

AI assessment note: “I just had a lot of confidence. I think, I think a lot of entrepreneurs”

Q people like Elon who just wants to like, he says, I want fresh blood. I want to like turn through people. What's your opinion on this? Like, do you want consistency on like your, your, your, the top people in your company, or do you like Do you want to encourage turnover? Do you want to keep the core product kernel team together? Like, how do you think about that?

A I think that people's level of experience can change, and you can learn unique things, but I think general aptitude is reasonably consistent, and what I mean by that is, let's say you want to take the snob route and just go look at MIT and find the smartest people there. You can reasonably figure that out within one semester of, like, who are the top 50 smartest people at MIT if you ask around and spend some time on that. And generally, people are not recruiting people for their internship program until their junior year or their junior summer, but you can go and say, actually, I'm going to try to find, like, the smartest freshman and offer them a winter internship or a summer internship and go bring them in and find the smartest and, like, incredible aptitude of people, and by the way, Other freshmen, when they see the smartest person went, they want to go to your company too, and you can start to create these virtuous cycles of finding great people. So I agree with, with Elon's philosophy of trying to find really smart people, in part because it allows you to find maybe something like a mispricing in the market by their junior summer, or after they've been working for five years, it's priced in. You're competing straight up with, ah, quant firms, AI labs, whoever you name it. Um, people are paying top dollar for folks, but, um, that early in career is when people don't have a…

AI assessment note: “So I agree with, with Elon's philosophy of trying to find really smart people”

Q So can you give an example of like a problem you're creating when you start in China, how long it takes to come ashore and what happens when it does?

A Okay, so what you learn when you go and do what we did in China is you learn that when you go and take your business and go to China, you have to start over. So many people think that you can take your business and take it somewhere, which by the way, Uber kind of like trademarked that if there's such a thing, like We made that a thing where like cities, countries didn't matter. We created a system that was inevitable, but China was different because of how that country works. Everything's different. And that means you have to start from scratch, right? It's like a, something as simple as like, uh, the phones, uh, or let's say maps, GPS. There's a different GPS system in China than there is here. What does that mean? Well, it's like different. So if I want to understand how cars are moving through space, I have to change my GPS system so I can do that. So I understand. And that's like one of like a hundred things that are different in China, which means you have to start over. And so, yeah, you're starting a new business when you take it to China and you have to, you have to be in a very receptive, like, I am going to learn how to do things differently in this very different place and be excited and interested in how different it is. Whereas most entrepreneurs, let's say Western entrepreneurs that go to China, that is almost none succeed.

AI assessment note: “There's a different GPS system in China than there is here.”

Q So what is the role that you're playing in the projects that you're pursuing right now?

A I will basically do whatever is needed to help form these businesses, and the reality of business, which very few people really grasp, is that the basics of business, no matter what the field is, are exactly the same. The blocking and tackling parts are the same. So as pointed out to me, A film or a television show or a book or a song is packaged around talent. Talent, creator, engineer, same thing. Talent needs someone to help execute. Engineer needs people around them to help get the business in line and organize, coded, whatever they need done. The creative person making the entertainment then has to get financing. The engineer or founder of a company needs venture capital. With the entertainment maker, he then has to get distribution. Founder has his product. He's got to find a DSP or someone else to distribute his work, or just take it on his own on the internet. Either way, both also need marketing. How do you put the name into the ether? And then how do you sell the product? How do you make a profit? How do you build a culture? How do you build something that lasts beyond you? We started CA in 1974. In 2026, it's as strong today as it was when I was there, because we set a business model in place that has stood the test of time, and the guys that took it over followed the trajectory of where they needed to take the business and kept the same values and principles. And at…

AI assessment note: “I will basically do whatever is needed to help form these businesses”

Q a venture capitalist. So like, when you're building Ribbit, How did you apply, like, your rebel, like, your inherent rebel nature to your, essentially, almost like, you're almost like an artist in the sense of, like, this is the canvas that I'm building, this is how you think I should do it, but this is how I'm going to do it. How did you think about it when you started?

A If I end up being labeled, first, I hate labels, and second, I will be very depressed. Because that's not the label, I want no labels. All I want in my tombstone is to say, he was a rebel. That's all I want to be said there. And that will say everything about me. The way I raise my kids, the way my relationship with my wife, the way I treat my friends, the way I make business decisions, the way I change my mind, I'm willing to change my mind if I learn something that is different. That's a rebel mindset. Everything that is the opposite is a mindset that I know too well. My kids are perfect. I'm the best at what I do. And I run away from any of those things. Actually, I, I find that the rebel mindset is one that you are always asking questions. You're a rebel. You are nonstop asking questions. You want to learn. You want to keep, but you and I know a lot of people that get to a point in life when they stop to ask questions and they start to preach. That's past the rebel time. And everybody has that breaking point somewhere in their lives. I want that to be the last day of my life. So I need to live by that principle on everything that I do, on every behavior, on, on, like, I'm really now against the traditional art world. I'm trying, you know, to allow artists to show art in a different way. Uh, we revel at Rivet, the way we design it. We were, people were asking, well, what are…

AI assessment note: “we revel at Rivet, the way we design it. We were, people were asking”

Q And why don't you have a driver's license?

A Cause I don't feel the need to drive and I'd rather think. I don't need to control driving. I want to control thinking. I want to focus. I want to be on my phone. I want to be doing something useful. And that's been the case since I was, you know, 19 years old. And so I'm happy to delegate things in a way that others are not. So one of the things that's different about my leadership is when I hire people, I hire very autonomous people who often go off and execute on their own, and they would be terrible in most corporate environments. But also I can't hire the same kinds of people. And that was true to me. Had I, you know, gone the other way, I wouldn't have been very successful. If other people go this way, they're not gonna be successful. Then again, there are a lot of things that are very similar, which is most of the best Silicon Valley leaders, they lead from a place of inspiring their people as opposed to, um, trying to, to get people to be afraid. But that is a form of leadership. There are plenty of leaders out there who are successful because they cause people to become afraid. And so you just have to pick the form of leadership that works for you, but also when you're picking where you're going to work early in your career, you should probably work somewhere where you're going to learn the lessons that are good for you. If you're more of a kind of person who can show …

AI assessment note: “Cause I don't feel the need to drive and I'd rather think.”

Q Wait, wait, wait, what do you mean? I don't want to be involved in anything big house. You say it's like a small deal.

A Yeah, like money. If we're not talking about a lot of motherfucking money, what are we talking about? So my, my analogy to that was just big houses. I'm like, are we talking about big houses? Because it doesn't even matter unless we're talking about big houses. They love that shit. Started laughing, and then Jay and I became friends and started playing Madden all the time, and then realized that our, not realized, but my, my cousin was his cousin. My, uh, my father's brothers My father and brother married a woman that happened to be, ah, connected to his side of the family. They were cousins. So my, my, my cousin was his cousin. So he was, we were second cousins. And like, that all came out because we started to hang out with each other. It was like, oh shit, right, that's true. Oh fuck, I didn't even realize that. And we, you know, ensued us.

AI assessment note: “Yeah, like money. If we're not talking about a lot of motherfucking money”

Q You didn't know who you were at 22, correct? So can you talk about the process that you went through to now say truthfully that you know who you are?

A Well, I think if you don't know who you are, the world will tell you, and it may not be an answer you want, right? So the world is noisy, especially when you have a certain level of visibility. It projects onto you as a, as much as it receives you. So I think you have to do the work, um, of, of really getting to know yourself and what feels right. Some of the hardest decisions I've taken, and sometimes it's really about Saying no and setting boundaries or, um, changing course. When those decisions, regardless of how hard they are, align with your values, it always feels good. Like, it's hard. It can be difficult, but you never question it. You never second guess and you don't look back and wonder what if. It's the decisions you take that don't fully feel right, that don't align with, with your true self, with that, those core values that, You hold. Those are the things that I think you always regret. Oftentimes people get there because they sort of forum shop decisions. They'll ask people about their life. What should I do? What should I do? And they, they almost make it like a process to make tough choices. And there's something very important about, you know, speaking to people who are knowledgeable and getting perspective and feedback. But ultimately, like, you can't outsource decision making as it pertains to Major decisions in your personal or professional life. You really…

AI assessment note: “Some of the hardest decisions I've taken, and sometimes it's really about Saying no”

Q How impactful are those words of encouragement? Cause you're, you're young.

A Like somebody you respect that was just a good man and a really good, good real estate broker. Uh, I really respected that cause he saw that it was affirmation that why I was being so fanatical and trying to talk everybody into it. You know what I mean? Except for the bullet makers, he believed in me. I'm like, okay, okay. That's it. That's his little wind in my sails. To do this and basically told her, Hey, it's going to take them a year to put all this together, but I believe you'll do it. And then I believe you have a long-term tenant. Look, sure enough, we've been here for almost 30 years and we got like a hundred, a hundred year lease going forward. And, and, and the family, she passed away, but the family's like, no, you know, I'm trying to, I'm trying to buy it. They're like, we just have pride in this, you know, so we'll just keep doing, uh, to keep doing a lease. I said, but we'll give you a hundred years, you know, and options to, to stay in this original location.

AI assessment note: “it was affirmation that why I was being so fanatical... little wind in my sails”

Q because 80% of your customer intelligence is invisible, hidden in emails, transcripts, and conversations. Unless you have HubSpot. HubSpot is where all of your data comes together so you can see the patterns that matter. Because when you know more, you grow more. And that is a pattern that never fails. Visit HubSpot.com today. That is HubSpot.com. Are there any product updates that get pushed live that you didn't like?

A Oh, plenty. Um, plenty. And, and, and this may be a little bit unique, but you know, coming back to it. So, you know, I, I ended up, um, Having, you know, so, so the typical thing is that the founder needs to be the product person, right? Um, by the way, it's a hundred percent true. I, I totally believe that. I think it's the most important thing in the zero to one stage. But what a lot of people don't talk about is the fact that there isn't one stage of this journey. It's like you're oscillating between zero to one, one to a hundred, and then, you know, the last stage was more like optimization stage. And you have to like constantly do that. And you're going to need different skills at different places. And this, this is why, by the way, I believe it's so important for entrepreneurs to realize when to apply what tools, um, in this journey. So what happened with Spotify is sort of against all the common wisdom and wealth, which is I don't really run product, um, anymore. Um, because what happened was I got this guy called Gustav that you now met and he runs product. And he's actually way better than me at doing it. And so, uh, speaking about sort of being truthful, what ended up happening, uh, many years ago was, um, I was running these product meetings. Um, he was sort of running it, but I, I wanted to run it, so I kind of interjected myself over him. Um, but I didn't have the…

AI assessment note: “Oh, plenty. Um, plenty. And, and, and this may be a little bit unique”

Q Yeah, they start with one, but you have 10 different products you could sell them. So how do you go from one to two, and then two to five, and so on and so forth?

A Yeah, I think the main thing is, one, And you, of course, deploy the first one. You'll make sure that there is value behind that. So across any customer engagement, we try to make sure that we don't only prove concepts. We prove the impact, prove the value. And only after that, we try to get the companies working with us at the broader scale. So we prove the impact on the marketing side to get the support going. What you actually need to do is not only the audio, you need to build integrations. So you need to connect it with All the CRM systems that, that Deutsche Telekom works with, you need to work on integrations with the output. So how do you connect it to the phone system, or the SIP tracking or Twilio, how you make sure that that connection exists. So you would spend a lot of time on integrations, making sure that their logic is respected on how, when you do pick up the phone call, the agent behaves the way you want it to behave. So here are four deployed engineers, would partner with the team, spend the time, and in Bonn in this case, in Germany, Working through side by side together on the integration, on just being able, making sure that the agent follows the flow that you want, has the knowledge that it should have, and then In that step, the, the, the hardest thing in any voice agent, uh, work is actual deployment of how you actually test that it works. Um, so then y…

AI assessment note: “We prove the impact, prove the value. And only after that, we try to get”

Q Right, so you buy the yellow Lambo. But more interesting than the yellow Lambo to me is what you said, where you said that The, what Bezos did, what Jeff Bezos did for you and Jason was gave you the confidence to go for it. Can you explain that?

A So in the early days of Thursday, we had launched Basecamp, it was taking off quite well, and we got a lot of interest and outreach from VCs. We counted 40 some at the time, and this was 2005 ish. I still had very vivid memory of the dotcom boom and bust. I had seen what happened to some of these VC funded companies and the internal mechanics of that, and I didn't like any of it. And I also had all these ideas about efficient businesses and what it takes to run. So we didn't actually want VCs, but Going back to this point about trusting yourself. I didn't fully trust myself not to get tempted by a twenty million dollar check, a fifty million dollar check, whatever the number was at a time where my bank account said, I don't know, 8000 dollars. Funny thing. My bank account did say highly, uh, slightly higher than that. When I came to the US, I think I had like, 50 grand that we had worked up as we started Basecamp. And the first thing I did as soon as I landed was Jason took me to an Audi dealership and I bought an Audi S for my first car cash. And then there was basically all the money I had in my bank account. So I just blew it all on the car and I thought like, we're going to make it back. But, um, This, this notion that we had something that was taking off, but this is all fleeting. I had great humility that like, I'd seen many other businesses, oh, it's popping off, and the…

AI assessment note: “So we didn't actually want VCs, but Going back to this point”

Q Dude, how many people are wearing Jordans without playing basketball on them?

A It was the only white space left, because there was no way I could market Reebok as the age, as the agency of record at the time. I told Paul, I'm like, Mr. Fireman, There is no way I can convince a sixteen-year-old they can jump higher or run faster than Nike and Reeboks. Like, like, that's not happening, ok? So, like, let's go into the other thing, which is the non-performance stuff. And it got so hot. That we got a chance to go into the performance business again, and we were trying to sign Kobe, and I have great stories of, you know, pitching Kobe. First of all, I signed Kobe to a record deal, recording contract when he was a, a rookie, and then we pitched LeBron. That's how LeBron and I became good friends to this day, when we pitched LeBron, and he, um, he has a famous story of LeBron. Uh, we're pitching him for Reebok. We, you know, they send a plane. Everybody wants to sign him. I, I tell Paul, while he's coming in from Akron, we're flying from New York to, uh, to Boston to meet him there. And I'm like, Paul, we do this in the record business and it works. You give an artist in advance. And you give it, you bring the advance right there.

AI assessment note: “So, like, let's go into the other thing, which is the non-performance stuff.”

Q So explain when you knew it was working the way it is now, and what was happening before Like, what was the, the model before that?

A Yeah, I mean, so where we are today is, and, and this is where we wanted to get to, which is the product has to be good enough to sell itself. Otherwise, if we're begging for business, we don't have a good advertising solution that's scalable. We don't have the salespeople to go beg for business. And so what does that mean? Well, if you're a game developer today and you plug into our platform, you're gonna spend a thousand dollars. You're gonna know with certainty you made more than a thousand dollars on that spent. You may have a business model that says, I want to break even on that thousand dollars in a year, and by year five, I know I'm gonna make 5000 dollars, and so you put the thousand in, you get a thousand back in a year, and year five, you're at 5000 bucks. You may have a shorter cycle. You might break even on the thousand in 30 days, and then by six months out, you made two, 3000 dollars. Whatever your business model allows, you're gonna be able to price into our system and generate more money from the dollar spent than, than what you put into the system. Now, what's important about that approach, Is that they become an arbitrage. The only constraint on them scaling in our system is the money that they have in their bank account. Cause if you tell someone you're certain to make more money than what you put in, you're going to know it. Our reporting is going to tell y…

AI assessment note: “where we are today is, and, and this is where we wanted to get to”

Q And almost no one knows who he is. Can you just talk about how you met him? What was it like working with him?

A I knew exactly who he was. And the reason was because his company, Silicon Graphics, his first company, they were the company in the valley between like, call it, call it, yeah, eight-seven to 94 or something. They were like, whatever, Google or OpenAI or whatever, you know, comp you want to make. Like, they were like the company. And by that, I mean, like, they were the company where the smartest people in the industry all wanted to work there. They built the products that were, like, the coolest products you could possibly imagine. They had this incredibly young and vibrant and dynamic culture. And then they hit this, like, cultural moment that was just incredible in, I think, 92, which was, uh, yeah, which was the turning point in the movie business when computer graphics really kicked in. And the two movies back to back were Jurassic Park and Terminator two.

AI assessment note: “I knew exactly who he was. And the reason was because his company, Silicon Graphics”

Q Do you still put an emphasis, I've heard you speak about this in the past, an emphasis of hiring and empowering young people? Is this business different than like when you were launching new cities in Uber, for example, where you gave a lot of responsibility to, you know, aggressive young people?

A Well, okay, again, so it, there's really interesting ways to do it. I, I, I sort of have this, this concept I call the line in sort of the, maybe the framework is finding the line. So there's a line. On one side is order, lots of structure, sorry, sorry, structure. Like as you, as you pull away further, further back into order, you have lots of rules, lots of structure, lots of process, and eventually lots of bureaucracy. And if you go too far back from that line, you're going slow and people are bummed. And if you go to the other side of the line, which is chaos, Lack of rules, lack of process, lack of structure. And as you go deeper and deeper and deeper into chaos, you also get to a place where you're going slow and people are bummed. So that line between order and chaos is innovation at speed and at scale. And the job of every leader is to find that line. And it's not in two dimensions. It's like an AD dimensions. Okay. And the best leaders are able to find that. And, you know, the, probably the most approachable way to describe this is the fewest number of rules while staying out of chaos is the, is the approachable way to describe this. But you go to back to like launch at Uber. You could think of it as like, okay, there's a bunch of 23 year olds launching cities. What happened was at the beginning, the first 20, 30 cities, I was deeply involved in whether that city was g…

AI assessment note: “I sort of have this, this concept I call the line”

Q How do I allocate my time across the existing problem?

A So, you know, so like, like Elon's famous for like, what is the, the bottleneck here? And like, I'll find out in my entire empire where the bottleneck is. I'm going physically there, and I'm going to sit there and like dedicate all our resources. In that essay I told you, I read about the history of SpaceX. They, they just, there's a NASA guy, a guy from NASA visiting SpaceX, and they're like, like when there's a problem, there's like a flash mob appears. So Elon has a very specific way. And I heard you on another podcast saying, like, you're attracted to problems. I'm just curious, like, I'm not talking about problems you could solve, like, in future product development. I'm saying literally, like, there's, you're running a giant company. There's all tons of stuff that's not going well.

AI assessment note: “Elon's famous for like, what is the, the bottleneck here?”

Q think to talk to you about this. We're going to look back on 2026 is a year that every business was up for grabs. He said somebody was going to build the AI native version of Shopify. And he said, and it's going to be me. And so at night, he is literally trying to rebuild. If, if you started from scratch, what would you do with deter current technology?

A That was the other thing I was going to say about him is he does it himself. Like he is using these tools himself. He's writing software himself. He's trying the models himself. He is trying to like re-imagine his workflow flows himself. Most CEOs, when you get to that level have like teams of people that Are managing teams of people that are trying to implement the thing, and they're trying to, like, make you happy, and they're trying to, like, you know, smooth the rough edges. I think it's very hard to get the feel if you're not actually doing the thing, and he, he does it so hands-on all night long as far as I can tell. I'm not sure if twenty-twenty-six will be the year that every business feels up for grabs. I might disagree with him a little bit there, uh, but, but I, I, I get the spirit of that, and I do understand that it feels like that's happening.

AI assessment note: “That was the other thing I was going to say about him is he does”

Q Was there a specific reason you, you started with food, though?

A It just caught me. I mean, like, that is, like, I don't have a list. Well, first of all, of course I did Uber Eats, so, like, very familiar with this part of things, but nowhere close to the atoms that are necessary to do what I just described. You know, I like to say, like, I have lots of ideas all the time. I mean, I, I'm an idea factory, but other people have great ideas too, but like an idea comes to you or comes to you, if that makes sense. And I'd like to say, you know, you go out on a date with the idea, right? Was it a good date? Did it go well? Like how did you and the idea get along? And it's very much related to like, who are you is going to be a big part of which idea works for you.

AI assessment note: “It just caught me... of course I did Uber Eats, so, like, very familiar”

Q Why do you think it should be one of the, the first things they're playing the game?

A Because it, it's, it's one of the things that flows the most in the world. Everything flows through money. Like my, my whole life, the thing about what keeps my learning going is I follow flows. I believe that nothing static, right? Money is never static. Money is like gravity. It always falls. It always moves. It always, always going somewhere. It's like water. It's, it's never stuck. Energy. Is flowing everywhere. From the lights that we're in here, but also our own energies. Right now we're creating both energies and we're, we're sharing that energy. And, and so I find that, um, For something that is as, as dynamic as money, it is not attached to AI yet on anything.

AI assessment note: “Because it, it's, it's one of the things that flows the most in the world.”

Q Do you want to say what bicycle face is?

A Bicycle face. Bicycle face. Bicycle face. Bicycle face. Yes. So it basically turns out every new technology is greeted with what they call a moral panic, right? So and a moral panic basically is whatever this new technology is or this new form of media is, it's going to ruin everything. It's going to ruin everything. It's going to ruin society. It's going to ruin morality. And then especially it's going to ruin the children. Um, and then, and then back, the bicycle was pre-feminism. So it also was, it's also going to ruin the women very specifically. It's going to ruin the women. Which clearly cannot be, because women clearly in, you know, cannot be trusted to use a bicycle without getting into real trouble. I'll explain, I'll explain why. So this is this persistent theme, and basically you, you go all the way back, and this is like, you know, this is like this famous thing where Plato and Socrates thought that like, you know, basically they thought that written language was a big mistake, that all information transmission should be oral, and they had this, you know, whole thing back in 500 B.C., and then it was just like every, you just have to like imagine, it's, I always like to hypothesize like, you know, the first guy who brought fire, you know, it's like, Down from the mouth. They probably killed him. Yeah, they were like, what the fuck is, you know, Right. Exactly. Like,…

AI assessment note: “every new technology is greeted with what they call a moral panic”