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Chamath Palihapitiya
CEO, Social Capital

Write Like a Billionaire | Chamath Palihapitiya | How I Write Podcast

🎥 Nov 29, 2023 📺 David Perell ⏱ 46m 👁 36728 views
Sign Up for "Writing Examples" and Learn From The Best Writing of All Time: https://www.writingexamples.com Come learn how Chamath Palihapitiya, tech billionaire and Silicon Valley icon, breathes life into his ideas — and how you can, too. This episode is all about the push and pull of online writing. Objectivity vs. subjectivity. Consuming vs. creating. Structure vs. spontaneity. TIMESTAMPS: 00:00:00 Intro 00:00:37 Buffett's annual letters 00:05:30 Energy of your writing 00:07:15 Twitter 00:14:00 AOL versus Facebook 00:16:40 Acquisition, activation, engagement, virality 00:23:40 Moments of...
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About Chamath Palihapitiya

In a May 2026 appearance on the Joe Rogan Experience, Chamath Palihapitiya discussed a range of topics including technology, economics, and governance. He argued that "attention" has been the central driver of technological revolutions over the past 30 years, citing Google, Facebook, and AI as examples. Palihapitiya also stated that the social compact between labor and capital has "totally collapsed," suggesting that corporate taxes should exceed personal taxes as a potential remedy. He compared the philanthropic efforts of past industrialists like Andrew Carnegie and John D. Rockefeller to what he described as fewer "living tributes" built by modern capital. Palihapitiya also commented on government efficiency, estimating that 30 to 40% of the federal budget is lost due to "shitty code" and inefficiencies, and predicted that documenting government systems would reduce waste and fraud. Regarding China, he said the country's system rewards judgment and long-term priorities, which he described as "almost orthogonal" to the American system. On the topic of Elon Musk, Palihapitiya credited Musk's purchase of Twitter with preserving free speech, which he called a "core component of our civilization" that he believes was previously "curated" and "tightly controlled" by the federal government.

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Transcript (58 segments)
✨ AI-enhanced transcript with speaker attribution
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Chamath Palihapitiya0:00
The best way to be an effective writer on the internet, in my opinion, is to actually be factual.
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Interviewer0:03
I bet Buffett was a big inspiration, but what makes a good annual letter?
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Chamath Palihapitiya0:07
Yeah, I mean, I think he's the GOAT. These are master classes in that structure. They are master classes.
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Interviewer0:14
Tell me about that moment of epiphany.
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Chamath Palihapitiya0:15
I would like to be a small part of that documentation of capitalism because that is the voting of good ideas. Money gets to vote on good ideas. More money into good ideas, more good ideas become good things in the world, better for the universe.
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Interviewer0:26
You have the heart, you have the soul, you have the hot blood, and you're roaring. Start it in a punchy way, end it in a useful way, and you'll be really successful.
As you were thinking about writing annual letters, I bet Buffett was a big inspiration, but what makes a good annual letter and who did you look at for your inspiration?
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Chamath Palihapitiya0:48
Yeah, I mean, I think he's the GOAT. I've read all of them. In fact, in my office, the thing that's been the consistent mainstay is that I've had a printed binder of all of his annual letters, indexed by year in which he wrote them. And so it's always something that I've referred back to. I would find myself reading random years' letters on the weekends. Certain letters of his I've reread probably 20 or 30 times.
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Interviewer1:24
Wow.
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Chamath Palihapitiya1:24
What I learned as well was sort of how to write effectively from his letters, I think more so than anybody else's. There are other people that have also done good letters, good public letters, but they're more sporadic. His is consistently good every year. There's something that you can take away both in terms of what you learn, in terms of net new information about how the world works, but also just in terms of stylistically, the structure of what makes good communication and good prose. He's been really probably a North Star.
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Interviewer2:01
So tell me, when you're writing your annual letters, what are you going for? What has you look at it and just say, 'Huh, it's pretty good'?
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Chamath Palihapitiya2:07
Well, for me, it's a catharsis because my business is not a team sport. My business is an individual pursuit, and it's an individual pursuit against the best version of yourself, and even to be even more reductive, yesterday's version of yourself. Sure. With this idea that you're constantly supposed to be adding something to your toolkit. And so what I'm trying to do, I typically start writing that I take notes throughout the year. So I'll have like a note in my iPhone, and if it's like something interesting, I write a kind of a bullet point to myself: XYZ just happened, or this thing happened, or here's a mistake I made, or here's something that went well, or whatever. It's like one giant Apple note or something, one giant note that's just a running list of the key few things that may have happened in the year. And then typically around February or March of the next year, I try to put structure to it. And what I'll do is the parts that are research-oriented, I'll ask my team, 'Hey, can you double-click into this thing in energy, or can you double-click into this thematic analysis of rates?' And none of those things are particularly that subjective. So I get help from a lot of folks to help me put the objective data together as well as the prose around the data. But then what I'm doing is I'm writing the intro and the end and all the connective tissue that basically is cathartically telling my story of the past year. What did I go through? And most of the time, I'm looking at it through the lens of what am I going to think about myself when I read this in a year from now or two years from now. Because the reality is the letter gets read about a million times, which is pretty good. But the only person I can guarantee you, well, most people I would say of the million reads, and that's like a page view count or whatever, or downloads and all that stuff, are best reading the table of results, maybe the intro, and probably the conclusion, and that's it. Then they'll scan the rest. So most people are reading 10, 15, 20% of it, would be my best guess. There is only one person I can guarantee you is reading that letter multiple times, and that's me. And there's literally only one person that will ever read those letters years later in my mind, which is me. And so the value is for me to understand why did I think that when I thought that, what mistake did I make, what did I learn. And so it has to be a reasonably good accounting, but it also has to ignore other people's version of what that accounting should be. And so it's hard to write prose for yourself because it also has to balance people's perceptions of what they want documented in that letter and how they want all of that information to be accounted for. And so what gets lost in these things is like, what is the point? And you know, it's very selfish. That point is for me. It's for me to be able to say what did I learn, what did I try, and what is this going to mean in future years when I look back on this as I try to get better.
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Interviewer5:32
How does your fire manifest itself in your writing? Right, there's been multiple interviews where you go on one, you get passionate about something, you have the heart, you have the soul, you have the hot blood, whatever it is that you're saying, and you're roaring. Does that show up in your writing process, or is writing a more cold, logical, analytical process for you?
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Chamath Palihapitiya5:51
There's two kinds of writing that I do. When I write with pen and paper, it's very calculating, and it typically tends to be a mixture of diagrams where I'm explaining things to myself and then dissecting ideas. And I purposely use pen and paper for that because it helps my precision and recall. It helps me learn things very precisely, and it allows me to learn in a way where I can recall that information much better in the future. But the more fiery form of writing is what I do online. And right, typically that tends to be my more reactive, and you know, I do that on Twitter. And sometimes, you know, I really like that, you know, it takes on a life of its own. You could say that. And other times, I'll write in like a Google Doc, and I'll write the thing that I really want to say because then I can then delete it. So I'll say the thing that is the unsayable thing, that is the highly politically incorrect thing, or the really insecure thing, or you know, the hurt version of Chamath kind of lashing out at some external person that may be saying something. And I write it, and then I can delete it, and then it's cathartic, and I can get past it to then say, 'Okay, what am I really trying to communicate?' And I can get back to the cold analytical self.
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Interviewer7:18
What is it like being the center of attention on Twitter for a 24-hour period?
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Chamath Palihapitiya7:25
It's very destabilizing.
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Interviewer7:28
In what way?
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Chamath Palihapitiya7:30
Well, I think that like, what are communications meant to do? What does one do when one communicates? I think there's a small percentage of communication which is, let me explain an idea and a concept. Let me put something into the world that I hope can grow and virally take hold in people's brains. It's Inception. But I think that that's less than 1% of all communication. I think that 99% of communication tends to be people processing their own psychological moment in time. And online is a very effective mechanism to give you feedback in a real-time way. And so when people are reacting and communicating real-time online, I think they're giving you a snapshot into their psychology. And so it took me a long time to really believe that. And instead, what happens is I'm hurt, or I feel like I'm better than other folks, all because of what I'm reading. None of those things are accurate. So I think that writing online particularly takes people away from this middle band of just being a highly tolerant person, where most people should be just very tolerant of their faults, but also their strengths, understand the context of it, and be okay with it. You know, tolerate the anxiety. Instead, I think what communication online does is it pushes you into this band where you become arrogant, or pushes you into this band where you feel extremely insecure and attacked. And the reason why that happens is that 99% of communication are people processing those feelings for themselves. Yes, they are feeling bad, they will make you feel bad. They are feeling pretty good, so then they'll pump you up, and then you feel probably better than you should feel. So it's all about regulating and re-regulating your emotions, and that's what real-time communications has both the power to do, but also is the downside of it. And I've lived both sides. And even though I can tell you this, in the moment, it's very hard to hit the pause button and say, 'Oh, hold on, this is not real, so let me just reenter myself.' And I think that's the biggest challenge. And I think that for people like me, I'm 47, I didn't grow up in this medium, it's probably much harder than for what it'll be for my children, who I think, as far as I can tell, understand that dynamic much more innately. Now, I may be inventing that, but it's almost like Darwinian. It's like, you know, humans are highly resilient beings. We evolve based on our environment to be able to take advantage of our environment through the maximum potential. And I think this environmental stimulus that we've never had to genetically adapt for may be a thing that our children are better genetically adapted for, which is that dynamic, the pace of communication and its impact on your psychological well-being, much better tolerated it seems in younger people than older people.
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Interviewer10:49
Tell me about 'Adult Children of Alcoholics'. I think that this book speaks deeply to how writing can move people, how it can just be a light bulb in the reader's eyes. And it seems like that book was really eye-opening for you in a profoundly positive way.
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Chamath Palihapitiya11:08
I have this kind of funny joke that I say is that most books don't need to be read because you can get it from the title. And sadly, it tends to be true for most books. But this is a book for which that is not true. But this shows the opposite of what an extremely well-written book can do, which is it gives you the question in such a profound way that it unlocks all the things you didn't know to ask. And so what that book does is it kind of just breaks down all of these ways in which you manifest the neglect that happens when you're raised by an alcoholic parent. And I didn't even know those words or that language. I just knew the manifestations. And it asked a question or it made a statement, and it made the statement in such a benign way. I was like, 'Yeah, I am an adult child of an alcoholic. What does it mean?' And then the way that she, John W. W., who wrote the book, the way that she writes is so phenomenal because it's like, here is all of these holes that it created, and then effectively here are some coping mechanisms, really, because it's not a solution. So she doesn't give you an answer key. But the way that that book is written and structured is just so powerful because it opened this Pandora's box of, 'Oh my God, that's me.' And then you could just look at the table of contents, and it was just so well organized. And she would give you the answer to each one, meaning like, you know, one of the chapters would be like some dysfunction that I had. She would just call that the name of the thing. Like, 'Oh my God, I'm that person. Oh wait, I'm also chapter 7. Oh hold on, I'm chapter 13 as well.' And I thought, what is going on in this book? There are very few books like that. Now, let me contrast and compare that. For example, I'm a parent. I have five kids. And one of the things that I was always afraid of, and I was very repressed actually by this idea, was do I continue to compound all of the problems that my parents compounded into me? Do I just compound them into my children? And some are easy. Okay, I was beaten a lot as a kid. Okay, don't beat your kid. Okay, got it. Easy to say, and for most people, actually pretty easy to do. Like, I mean, you got to really lose it to want to try to physically harm your child. It turns up because I've seen it. And so, you know, it is what it is. So okay, I was able to do that. You know, don't be an alcoholic. Okay, I was afraid, like, am I genetically predisposed to this? And it turns out not really. It's for me, at least, it was more of a choice. And so, you know, other than wine, I've been abstinent of not just alcohol, but you know, drugs. I've never had any of those experiences per se.
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Interviewer14:07
Right. How were the writing cultures different at AOL versus Facebook?
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Chamath Palihapitiya14:13
Well, AOL was a highly political organization that was in decline.
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Interviewer14:18
Political in what sense?
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Chamath Palihapitiya14:20
Not the common political. Political in terms of organizational politics. Organizational politics, because it had executed a failed hundred-billion-dollar merger. Everybody was, you know, in a mode of CYA. You know, people were getting fired left and right. And so it was a very complicated moment for the company. But as a result, your communications really mattered because you were judged on the quality and the succinctness and the viability of what you were saying, because that was the system of record for the business. That was the artifact that allowed you to judge apolitically in an otherwise political environment. So email became a very, an email index became a critical resource for some amount of functional decision-making in an otherwise highly dysfunctional environment. Facebook was kind of the opposite, or not the opposite. If I had to contrast and compare, we had a handful of dashboards because, you know, especially in my part of the business, it was an extremely unapologetic, unemotional, scientific approach to we're just going to go and dominate the world. And we reduced that to growth and acquisition of people and building up network density and all of the stuff. And so we had an extremely scientific way of baselining the business. And so as a result, there was just a lot of very poor and sloppy communication because the numbers were just so obvious that all the other stuff was a little bit of window dressing. And I think like in that window dressing, people didn't take it as seriously. So I found myself, I remember thinking, 'Wow, my communication style is too much for this place.' Meaning I had to like dial it back from like an eight to like a four in its simplicity, in its prose, in its colloquialisms. You know, it could be a little bit more crass, all the things that I had never done and had permission to do. I had to adapt because then, you know, otherwise these 22-year-olds think this 29-year-old is a lame ass. You know, and so you just had to adapt. And so my writing became slightly worse because it didn't matter. Right, you know, the numbers were like up and to the right, and those dashboards were essentially single source of truth.
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Interviewer16:41
Tell me about this cycle that you had: acquisition, activation, engagement, virality. Let's talk about that as it relates to how would a writer think about those four things.
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Chamath Palihapitiya16:50
So the context of that is that there's a guy that worked for me who's still at Facebook. He's now the CMO. He's an incredible, incredible guy. At the time, was a young man that we recruited from eBay. His name is Alex Schultz, and Alex had learned that framework from his boss, and he taught it to me. And I was like, 'This works for us,' so we went with it. But if you had to break it down, what the whole concept of it was is like you have to have a problem statement about what it is that you're trying to solve. And in that case, the equivalent of that was just, okay, getting people in the door. That was the problem. So acquisition. Activation was more of a process of like, how do you get them engaged? This is like, how fast can you make your first friend on Facebook? Exactly. Then there was engagement, which is like show them actual product value. And then virality, which was get them to tell it to others. If you're asking me how that translates into writing, yeah, it's actually the exact same process in many ways. Which is, you know, acquisition when you're writing is, and I do this a lot actually on Twitter now because Twitter is a way for me to write long threads and stay sharp. You know, one of the things I realize is that if you only write a letter once every, call it, year, you're going to get rusty. And on the other end of the spectrum, I was only writing, you know, these dumb small little things. So then when Elon extended the product so that you could really write long-form, I really like that. So acquisition is what's your hook, get them in. And so, you know, you have to say something that cuts through all of the noise of what people are reading on a daily basis. Then activation is really the TL;DR. You have to give them the, okay, this is why it matters and why you need to pay attention. Then the engagement part tends to be about the explanation. Right, now a lot of people confuse subjectivity and objectivity. So when you explain something, I think it's very important to be able to separate what is fact and what is interpretation. And I think where a lot of content gets misguided is they don't make it clear enough. And so your writing becomes this, you feel it, it's very hard to describe as a reader, but you're like, 'This doesn't sound credible.' And part of that can just be adding statements like, 'And so, you know, as a result, it leads me to the conclusion that...' You start to create these demarcations where, clear, here's where objectivity has ended, and now here's where subjectivity begins. And as a reader, oftentimes I appreciate that better because I'll throw most of that away. You know, Michael Milken, I think, went through papers and he used to have one highlighter for what was the objective and one highlighter for what was the subjective, just so that he could see the structure. Because the wrong interpretation of what we're saying is everything should be objective. What you're saying here is that the demarcation between objective, this is factual reality, and subjective, this is now my interpretation of such reality, those just need to be different. And when that's well done, it inspires trust. Writers are not taught how to demarcate this properly, and so instead it becomes this convoluted soup where the reader has to figure out where did the fact end and where did the interpretation begin. And I think that makes for terrible prose.
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Interviewer20:21
Absolutely useless, unreliable prose. And typically that's when I'll stop reading. You know, a lot of people ask me like, what books do you read? And mostly I read no books. I read articles, infinite numbers of articles, scientific papers, etc. I read all kinds of stuff. I'll read chapters of books, but I'll never read a book end to end. And so, you know, what you're getting with bad writing is when you don't know what you're getting, and the writer themselves is confused. And so then the reader themselves has to disambiguate: are you lying to me, are you trying to shape what I'm thinking, or are you telling me what's happening? And I think that that makes for very poor writing.
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Chamath Palihapitiya20:57
Yeah. And then so the last part is how you end. And the way that I think something has to end is conclusive, but that has to be overwhelmingly objective. And the reason is that you want to leave that reader with the sensation that they are net, like, you have to think about it as an equation. If you invest three minutes, that's a long time actually. If you time out, if you just start a clock and write three minutes to read a long-form tweet, man, that is like a, that's a lot of time. It's uncomfortable to sit in silence for three minutes. That's an equation where they are investing or they are paying you in time. And I believe, again, I'm talking about nonfiction obviously, but I believe that a good nonfiction writer has to be able to pay that equation back at the end of that time commitment where you have walked away with a conclusion that's net additive. You may not agree with it, but you feel like, again, it's a sensation that was worthwhile because it's not as if you are measuring on a clock and saying, let me divide this by my annual salary and did I invest, you know, $945 or whatever. You're not saying that. You just feel like was it worth it or not. And if you guinea pig this on yourself, the things that are the best reads tend to finish conclusively. So if you think about acquisition, activation, engagement, virality, and go back and read some of Buffett's best letters or go back and read 'Good to Great', these are master classes in that structure. They are master classes.
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Interviewer22:56
I haven't done it for my email, but I wonder if I went back and I did it, I would think about how it was structured that way, even though it was more, you know, meant to be more praxis and not meant to be, you know, objective really. It was all about my subjective truth. But I suspect that there's a version of that structure in there.
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Chamath Palihapitiya23:17
It is a really effective structure. And so I get to write these long tweets, and I try to write three to five a week. It just keeps me sharp. How do I stay objective? How do I demarcate subjectivity? How can I just be really punchy? How do I give the TL;DR? How do I conclude objectively so that this person felt like that reading that was like a good use of their time?
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Interviewer23:43
Tell me about that moment of epiphany. So do you feel like the moment of epiphany happens once you have that clear takeaway? Do you feel like it is like, hey, no, this is more of a routine, I sit down, takes me an hour and a half, and generally after about an hour and a half I get in the flow? Where on that spectrum are you?
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Chamath Palihapitiya23:55
I read a lot of content. Bloomberg is a very good example because they also have great graphics, and using graphics allows me to stay objective because it forces me down a path where I have to be more scientific. If you look at the magazines Cell, Science, and Nature, collectively these are the three most preeminent scientific journals, papers in the world. This is the smartest, most well-funded labs all around the world essentially trying to get published for their breakthroughs. There was a study that went back retrospectively and said, what percentage of the papers that are published in Cell, Science, and Nature are reproducible? Now, why am I asking this question? Because this is a perfect example of objectivity and subjectivity and confusing the two. Okay, now you know the answer because I just set this up. The answer turns out to be 30% is even reproducible. Forget whether it's a value and forget whether it's meaningful. Okay, forget statistical significance and then value because those are other orders of magnitude lower than that. Barely 30%. Now, those are magazines, let's call them, that I read semi-religiously to understand what's going on in the world, confusing objectivity and subjectivity, right, all the goddamn time. But it's written in a magazine that you think is 100% objective. It's Cell, Science, and Nature. It doesn't say David's Cell, Science, and Nature. You know, it's not Chamath's opinion on Cell. It's called Cell, Science, and Nature. These are objective things that exist in the world, yet 30% are reproducible, which is a way of saying there's a lot of made-up stuff in the world that hides as fact. And so, you know, as a writer, you have a responsibility to say what is fact and what is your opinion. Right, you know, it's unemotional, it's conclusive, it's useful, it's additive, and boom, you cut through the clutter. So to me, like, citizen journalism just manifests this equation: be factual, just a fact, sir, or just a facts, man. Start it in a punchy way, end it in a useful way, and you'll be really successful.
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Interviewer26:07
That surprised me. But it surprised me not because those people exist. I think those people have always existed, they just now have a distribution format. What surprised me is how successful they can be. It seems like you were saying this to me earlier, you're really doubling down on your talents, your gifts as a communicator, and seeing that as the path that you want to walk increasingly. Is that right?
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Chamath Palihapitiya26:31
I struggle with this question, but I think that I'm good at directing energy into ideas, and how one does that in part, but the large part is through communicating. You know, if you can start a business that's trying to build a, you know, form of cancer diagnostic, that's an incredible feat of engineering and science. But if you can't convince somebody to work with you or for you, that company dies on the vine. So that's a communication problem. It's not a technical problem per se. And there's lots of great technical products that have died, and there's lots of inferior products that have succeeded. And as far as I can tell, the gap is in how one communicates. And so I do think that, you know, it's a skill that if you have one productive way, and I think that I have some of it, is to try to breathe energy into good companies and, you know, good ideas that are trying to do important things in the world.
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Interviewer27:27
How do you hone and refine this craft? I think that the way that you framed it itself is almost worth investigating: breathing energy into ideas.
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Chamath Palihapitiya27:37
I wrote about this company on Twitter. Catchy title, good TL;DR, facts, and a conclusion. And one of the people that reached out to me was a person that I followed who wrote a lot of stuff about investing. And this person turns out said, 'Hey, can I get connected to your CEO? This sounds interesting.' And I just got a call from my CEO today. 'Dude, you'll never believe this. This person is like one of the most senior, skilled chemists we've interviewed. You know, it's going to be a big lift trying to get this person to join, but we're going to do our best. I may need you to talk to them, etc., etc.' Okay, we don't even know if this person is going to come join us. But it was the ability to breathe energy into that idea and describe it in a way where that person didn't have that feeling that, you know, is it subjective or objective? No, that's subjective. I agree with that. Good conclusion. I'm on board. And he reached out to me because we follow each other. 'Hey, introduce me. I'll take a shot.' That feels very validating. And if I had to give credit, it's going to be the CEO and the team that closes this person. But 1% of that is the writing. It was the writing that allowed that person to say, 'I'm going to explore this further.' And I have had innumerable examples. This stage zero cancer testing company was because of the same situation. This person who read my annual letters reached out randomly through our inbox at socialcapital.com. And it's now three years later, we have a stage zero test for bladder cancer, and we're starting to work on a test for prostate cancer. What is my letter? My letter was a catharsis, but my letter is meant to be large parts objective, but very clearly delineated sections of subjective catharsis. And it allowed that person to say, 'Huh, this person's okay, working on interesting ideas.'
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Interviewer29:47
One of the things that you've written that I think is just a little paragraph that I've taken and I've said, 'I really like that paragraph, I want to go evangelize that message,' is, and I quote: 'Start writing your perspectives and publish them. The ability for smart, useful observations to get into the hands of people with fewer ideas but lots of capital have never been better. You can build both a reputation and a balance sheet this way.' I love that paragraph. And I feel like so much of the work that I'm doing at Re: A Passage, so much of my own raison d'être for my career is in that little paragraph.
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Chamath Palihapitiya30:22
I think it's stating a lot of things there. A lot of what we've just been spending time talking about. But yeah, there is a dearth, it's crazy, there is a dearth of facts, and then there's a dearth of objective writing, totally, and really good writing and really compelling writing. I'm sort of always amazed at how many words there are on the internet, and yet how much it seems like people are starving for good words. And I find the juxtaposition between both of those things, it doesn't quite make sense. Think about like, I think part of why is that, you know, we've trained people on the opposite. So is sugar bad? Not inherently. You know, if you look at glucose inside of a cell, it's critical, but too much sugar causes diabetes. Sure. Online, there's too much of the opposite of good writing, which creates the vacuum and the need, whether you know it or not, for good writing. And part of why Substack, I think, has been successful because it gave people the chance to say, 'Well, you can vote in a very obvious manner on whether my writing is good or not.' I think what a lot of that writing is, unfortunately, is it's too long. I think that you have to appreciate that again, there's an evolutionary aspect to humans. I used to have both the patience and the mental training to read in long duration. I cannot read for three or four hours straight. I could probably read for 40 minutes.
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Interviewer32:00
You know what kind of writing I wish that you would go back to? I think your Quora answers from like a decade ago are quite good. They're personable, they're open, they're honest, they're really real. And I wish you did more of that.
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Chamath Palihapitiya32:12
I think my biggest problem is I've gotten a little bit gun-shy. I, you know, if I use the baseball analogy, I feel that I choke up on the bat too much these days. I used to be very raw and instinctual, and my writing on Quora was that. It'd be, I saw something and it's bam, published. And then what you find is that at a certain level, you get what I call like politician syndrome, which is you're always veering between 51 out of 100 people hate you or 51 out of 100 people like you. And if you don't have enough psychological resilience, that affects you. And I believe that my biggest challenge, going back to the book that you started this with, has been that journey. And my writing, again, as I look at the arc of my writing, I think if you measure it in one way, you would say it's at a global maximum. It's millions of people read this stuff and blah, blah, blah. But I would say to you more honestly, it's a little bit of a local minimum. I don't think it's a global minimum because I've written much poorer in the past, but it's a local minimum. And if I compare the style, what I'm not getting across is that authenticity and humanness and humor and relatability. And it's because I'm stuck in this 51-49 seesaw that is in my mind. And so, you know, I can see it in my writing that I agree with you. So I'm not as instinctual. I'm a little bit more guarded.
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Interviewer34:01
So I'm going to make a comment, two comments. So the first comment on a question. So the first comment that I think is interesting is I've read that when you play poker, you have lower stakes poker, you're a lot more analytical. Higher stakes, you're a lot more raw and sort of natural flowing. Is that true?
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Chamath Palihapitiya34:17
Yeah.
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Interviewer34:18
So what I think is interesting then, the question I would ask is, do you feel like when you're hanging out with your buddies, you're texting the best days for the All-In, do you feel like you have that authenticity, that relatability, and then it gets squashed for public consumption? Or what's going on there?
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Chamath Palihapitiya34:33
I think that writing is so, it's just one of these very tough things that it just exposes a lot of you. I think that when I verbally communicate, I can get into a flow state. When I write, like I said, I think that I have gotten into a phase where it's such a permanent documentation, and that, you know, these things come back at you a lot, that it makes me second-guess my better instincts. And so I have to find a way of recapturing that energy because I agree with you, the prose and the quality of my writing, it was raw, it was more unpolished, but it was so good. I felt like I was hanging out with you. I honestly felt like we were in a group chat. And then, but like, you know, going back to my annual letters, you know, I struggle sometimes, which is I think, man, it's just so much here, but so much of it is, should I just strip out the factual and just write a more just like raw two-page letter? But then I realize I can't necessarily do all of that because, you know, there are winners and losers on both sides of everything that I'm involved in. And then so I get back to the 51-49 thing in my mind, whereas back then I didn't feel a 51-49 because I had no stakeholders, and now I do. Like, you know, if I wrote something which is like, 'This thing sucks,' that could be a very great way relating to a friend about something, but that thing may only suck in that moment and then may start unsucking. But then if somebody's about to join that thing and then says, 'I'm not going to join, Chamath says it sucks,' the implications of all of that now, I've lived after 11 years, have caused me to be a little bit more... well, one of the things that I find works really well with students who struggle with this, now you have it differently because you have such a persona, public persona, and I've never faced that, but where I would experiment here is going on walks and doing voice transcriptions and getting fired up there. And at least this is my plea for you, at least having your first draft not be coming from a place of fear and what is everybody going to think about me, and having your first draft come from a place of passion and enthusiasm.
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Interviewer37:08
Okay, I love that. So say more. So how would I do this? Like if I'm...
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Chamath Palihapitiya37:10
So what you do is like the GPT-4 transcription is getting really good. So what you do is you open up your phone and go walk around the neighborhood and get into it. Go and have it all there, and by the end you'll have a transcript, and you can then write from that. And I think that if you can start there, oh, I love this, then you won't be starting from fear, because that's what I'm reading in your writing. There is the repression, and I had a sense that it was there, and then I read your Quora answers, and I was like, it is there.
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Interviewer37:45
Yeah. So, you know, to your point, like, I mean, if I had to then just reframing that, maybe why I'm now so married to fact is so that I can hide a little bit, because those facts are easier for me to talk about because I'm afraid of being subjective. And there's probably areas where I could probably be a little bit more subjective and emotional. So I think it's great feedback.
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Chamath Palihapitiya38:10
Well, I think, look at Gerard. Gerard influenced you. Gerard is an extremely, uncareful thinker. Uncareful. He is extremely subjective. He has no data behind what he's, he's just reading his stuff and he's saying, 'These are my conclusions.' And yet it influenced you like that. And I don't think anyone is reading Gerard for the empirical, factual, whatever. But you just said immensely, so immensely. What's going on there?
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Interviewer38:38
Well, he does something that I think is very rare, which is high-quality subjective prose. And I guess maybe what I'm saying implicitly is like, so, you know, maybe it's not 99% of prose is trashy, but 98% is. And there's 1% of good fact and there's 1% of good prose, subjective prose. And, you know, if you're a good writer, you're trying to be in those last 2%, as opposed to, you know, you get reductively bucketed into hashtag XYZ, hashtag this, hashtag that. You know, so it looks like empirically the brain changes once text gets introduced into society. People get a lot more logical. And these writers basically said that in the grand arc of human history, you had years of an oral culture of people speaking, and it's very emotional, it's much more tribal, it isn't empirical at all. And then you get into this world of text and logic. And now we're moving back into what he called secondary orality, which is of the internet. Because even though Twitter is textual, there is something in the vibe is a lot of how a group would engage with the pylons and the drama and the momentum. And it speaks to some big shifts in the human condition.
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Chamath Palihapitiya39:59
Yeah, I think that's very well said. I buy that. I mean, I think that it, I mean, look, it reinforces my biases, so I want to be careful. But I think that that sounds like how I have thought about the world. And, you know, that's where I think like there is value to breathing energy into things.
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Interviewer40:21
How are you teaching your kids to read and write now?
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Chamath Palihapitiya40:23
To be very honest with you, I don't think I'm doing a particularly good job. There is no well-written book on parenting. And so, you know, if you go across 30 different books on parenting and you look at reading, it's all the stupidest ideas. Like, 'Oh, you're going on a trip to Pompeii, well, give him this book about the volcano in Pompeii.' And then I give it to my kids, they're like, 'This book sucks.' Well, okay, there goes that idea out the window. 'Oh, ask them what they like and get...' And it's like, that's not how I read. You know, and I wasn't a particularly curious reader. But it was when I started to solve problems that I became curious about problems, and then I started to read because it was a necessary tool to ignite my curiosity about the problem. And I loved learning and I loved acquiring knowledge, and reading was just a pathway for that. And so I'm trying to calm my own psychological insecurity and tell myself that my kids, you know, are going to ebb and flow between phases where they read a lot and they don't. And I haven't yet, the bigger answer, I think, is I haven't yet figured out what is it that they're curious about learning more about. And I think that I hope that of the five, enough of them, you know, if three of five become curious about it, that'd be great. You know, learning, and then you can direct them to read as a tool to expand their learning.
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Interviewer42:08
You use data a lot in your investing process. Have you thought about using it to improve your writing? And if so, how would you think about that?
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Chamath Palihapitiya42:13
Yeah, I mean, I think that the one thing that I think I don't have a very good sense of, which should be empirically known, I think that there's a matrix of when you, so if you're going to publish short-form information content of any kind, I suspect that the length should be correlated to the time where it's most likely to be read. And so, and I suspect that there is at least one standard deviation, if not two, probably one, between the length. And what that means is that the type of information that's best consumed in the morning could be very, very short, and the stuff that's consumed at night could be very, very long.
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Interviewer43:00
Last question. How does your background as an electrical engineer change your writing? I mean, I hear you talk a lot about structure. Things in your life seem to be well-structured, well-thought-out. Structure is a word that you've used a lot. How else does it show up in your writing and your communication?
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Chamath Palihapitiya43:16
It's really important if you're going to take the time to write something down to have a point in doing so. You know, it's easy to jump in the comments of something and just throw shade. Okay, I'm not sure you're learning anything. I'm not sure it's net additive to the body of knowledge of the world. And then there are other things that, you know, if you were to write it well, could be. And there are just so many examples of just random people, anonymous people oftentimes now, writing things that just infinitesimally move the body of world knowledge forward a little bit. And so for me, the best way that I improve my odds of writing things that I can look back on and say that was slightly, infinitesimally additive is if it's structured in a way that I can understand. And again, I use Twitter just to stay sharp. I have drafts saved, right? And I'm constantly going back to them and I'm reading them and editing them in real time. I probably edit something 20 or 30 times before I put it out there. Oh wow. And I'm always just, because like I'll say it, I'll wait an hour, I'll come back to it, I'll wait 20 minutes, I'll come back to it, I'll wait five minutes. So there'll be, and you can see that it asymptotes in terms of the delta T that I take between edits. That's when I'm like, all right, trip it. And I'm always just trying to figure out like, is this good? Did I learn something even by writing this? Yeah. And so it has to have that structure. Is that interesting? Did that get me? Is that factual? Am I just, you know, is this my insecurity or is this true? Oh, it's my insecurity. Delete. Oh wait, why am I saying that? That sounds so dumb. That's just me being, again, insecure. Oh wait, I'm being intolerant of my anxiety here. Hold on, take it. I mean, so it's like very therapeutic writing for me. And I think over time, if I can look back and say there's a documentation of capitalism, I would like to be a small part of that documentation of capitalism because that is the voting of good ideas. Right, that's what money is. Money gets to vote on good ideas. More money into good ideas, more good ideas become good things in the world, better for the universe. But if you communicate bad ideas and bad ideas get too much money, then you slow that progress down, and there's a gap between what the counterfactual is and what the actual is. And so I want to be a part of that documentation so that as I introduce my version of good ideas, they can be voted upon, and then potentially they could be acted upon. And then separately, that's more on the daily basis, and then over the years, I want to be able to measure my evolution. And so I force myself to document basically where I am. And I lead with things that are shields for me, to your point. You know, why do I put my returns up top? Now I'm answering you, you've gotten in my head. Why do I do it? It's a shield. It's a psychological shield. It says, no matter what's, you know, it's my way of saying, no matter what's here, just remember this. Right, can't hide from that. Yeah. And that's a little bit of a cop-out. I wouldn't have said that until I talked to you.
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Interviewer46:38
Cool. Well, thanks for coming on. This was fun.
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Chamath Palihapitiya46:40
Thank you, dude. Good to finally meet you too.