23: Tamara Winter - Tacit Trust & Caring Curiosity

Speaker A: Welcome to Dialectic, episode 23 with Tamara Winter. Tamara, or Tammy as almost everyone calls her, is commissioning editor of Stripe Press, Stripe's publishing arm, where she and the team seek to identify the ideas that matter most for Stripe's audience and publish them by way of a small amount of books every year. Before she joined Stripe, Tammy worked at the Charter Cities Institute and at George Mason University's Mercatus Center, which is chaired by Tyler Cowen. While we certainly talk about Stripe Press and the incredible books and ideas that come out of it, this conversation is ultimately a holistic look at what makes Tammy so special.

Anyone who's ever met Tammy has experienced the radical warmth that her presence brings to every single room, and that's something that I think is rooted in her orientation towards living a relational life. She simply loves and is deeply interested in other people. We start the conversation as I force Tammy to reluctantly discuss what shapes her taste. We go deep on what Tammy calls load-bearing infrastructure, or many of the hidden forces that maintain a healthy and trustful society, from small social things like small talk to much more serious and significant things that maintain safe societies.

We also talk about Tammy's unique career path, what she's learned from writing and journaling, and the advice she has for reading, particularly her case for biographies. Tammy is somebody who simply fills you with energy, but she is also wise. If you enjoy this episode, please share it with a friend. It means a lot. And with that, here's Tamara Winter. Tammy Winter. Hi. It's good to be with you. Speaker B: It's good to be here. Speaker A: I think the theme that will bound most of the conversation is something that feels really, um, representative of you, which is this notion that there is one part of the world that is legible and codified and very explicit and well understood and articulated.

And then there's another part of the world that is a more human part of the world that is hidden or illegible, or at least not as explicit, much more implicit. And I think you're more interested in that part of the world than almost anyone I know. I want to start, though, with a topic that I know you have complicated feelings about. And yet I think you also have a lot of insightfulness about, which is inspired by a conversation we had at dinner with somebody who you work with. And I asked this person what makes Tammy so good at what she does, specifically at running Stripe Press.

Their answer was twofold. The first part was kind of obvious, which is there's a bunch of things that go into the actual day-to-day of being able to publish great books on the tactical side, on the structural side, the mechanistic side. But the second part of their answer about what makes you great is taste. And specifically what they had to say about it was that unlike almost anything else, most domains, there's a ceiling on how great you can be. And their answer was that taste is something that scales infinitely, which is what makes you so special.

Taste is obviously a complicated idea. I think it's been, um, particularly in tech and Twitter land talked about a bunch recently. I think you also talk about this notion, maybe at a more foundational level, that people actually don't really know what they like and why they like it. And I think you have a really clear view, whether it's expressed or not, on what you like and why you like it and what you believe in. And so my first question is, to the extent you can, I'd love for you to try to identify the threads or the patterns that run across your taste.

Speaker B: I'm not sure I can do that because of what we talked about, which is that taste is so nebulous. And I think— I feel as though every time this conversation comes back into the zeitgeist, I understand less of what we mean when we say taste. I don't know if that's your experience, but it's certainly mine. And I think the problem is that we tend to talk about taste as though it were some combination of explicit knowledge, but I think it's way more like tacit knowledge. And I think we'll talk about tacit knowledge later.

But, you know, when I think about how I developed my taste, a big part of it, I think, starts in childhood. And when you're young, right, the first part of taste is just absorbing a lot. I think everybody has to be honest with themselves and, and just acknowledge that a lot of what we like, what we don't like, and our ability to articulate that has to do with our closest influences. For example, my music taste. I will tell you, I'll be the first person to tell you on any given day, my music taste is my father's music taste.

You can almost break it down to, oh yeah, my dad likes it, I like it, right? And this is for a lot of reasons, but you know, I remember growing up as a kid, my very first concert— I don't know if I've ever told you this— was Earth, Wind Fire. Speaker A: I think you maybe told me this, but that's amazing. Speaker B: Yeah, it was Earth, Wind Fire and Chris Botti. He's a— Speaker A: do you have any idea what year? Speaker B: Ugh, this has gotta be— Speaker A: Or what age maybe is a better— Speaker B: I was like 8 or 9 or something.

Yeah. So I remember it, but you know, I had grown up listening to Boogie Wonderland, Fantasy, and so on and so forth. And so I guess the first part of taste is absorption. Speaker A: do you have any idea what year? Speaker B: Ugh, this has gotta be— Speaker A: Or what age maybe is a better— Speaker B: I was like 8 or 9 or something. Yeah. So I remember it, but you know, I had grown up listening to Boogie Wonderland, Fantasy, and so on and so forth. And so I guess the first part of taste is absorption.

Speaker A: Yeah. Speaker B: And I think the other part of this, I guess, as it relates to my work, is that I read a lot as a kid. And it's hard to have a sort of finger feel for what good writing is if you don't read a lot. Yes. It's just really hard to do that. Yes. And I think, you know, maybe one theme of what we'll talk about today culturally is that I think everybody wants the version of whatever it is that ends in mastery with, like, the least friction and, like, the least amount of work possible, which I totally understand.

But yeah, the first part is absorption, right? Just getting a lot of references. And so I grew up with a lot of references, right? So yeah, there was a lot of Motown, but there's some country in there, there's some pop. You know, my dad is a pop girl too. I don't know that he would describe himself as such, you know, a lot of like weird British '70s experimental stuff. And yeah, you just have to have, I think, first a really broad base to sample from. But maybe the second piece of this becomes pattern recognition, you know, knowing what you like and why you like it.

And I think for me, working at Stripe has been maybe the best thing possible for developing this kind of pattern recognition to do what it is I do. When I started at Stripe, it was kind of a— I guess it was a weird time for all of us because I— my first day at Stripe was February 24th, 2020. Speaker A: Amazing. Speaker B: I moved from C. to San Francisco to work at Stripe. I had 3 weeks between getting the job and moving. Speaker A: Right. Speaker B: And then 1 week later, we went remote for COVID.

So I'm in this job. I've never done anything related to book publishing, comms, any of that. The Charter Cities Institute was about 4 people when I left. Stripe was about 2,800 at the time. Speaker A: Right. Speaker B: So just, you know, completely out of my depth and out of home as well. So I didn't start off at Stripe in this role commissioning books, but a lot of the work that my team did, which was this extremely nebulous team that worked on everything from Atlas to IndieHackers to Patio11 and everything Patio11 entails to Stripe Climate, which is now Frontier, to weird side hustles for Patrick and John.

Um, that team's sort of secret sauce was its taste. And so it became very clear very quickly that everybody around me had a very clear idea of what excellent looks like. What it is we're trying to do here, even though again, we had no clear mandate. The ability to absorb the best parts or the most interesting parts of other people that you trust is a huge part of how you form your own taste, right? Speaker A: Yes, yes, yes, yes. Speaker B: And so you end up as an apprentice. I always joked that my role when I started was as an apprentice to the most interesting people that I knew.

And so that was people like Sasha DiMarini. She's now the head of comms at Anthropic, but She was kind of the ringleader of this team, right? Or Everett Katigbak, who is a filmmaker by trade. He was one of the first— he was the 7th designer at Facebook, and he was one of the first when they had that really experimental lab. Uh, and then he went on to Pinterest and then to Stripe. People like Patio11. And that— those were the people that I was just learning from. And then of course, you know, Patrick as well.

But that was extremely fun because these people are curious as a as, as a, like their job is to be professionally curious. Speaker A: Yes, yes, yes, yes. Speaker B: And so you end up as an apprentice. I always joked that my role when I started was as an apprentice to the most interesting people that I knew. And so that was people like Sasha DiMarini. She's now the head of comms at Anthropic, but She was kind of the ringleader of this team, right? Or Everett Katigbak, who is a filmmaker by trade.

He was one of the first— he was the 7th designer at Facebook, and he was one of the first when they had that really experimental lab. Uh, and then he went on to Pinterest and then to Stripe. People like Patio11. And that— those were the people that I was just learning from. And then of course, you know, Patrick as well. But that was extremely fun because these people are curious as a as, as a, like their job is to be professionally curious. Speaker A: It's a way of being almost. Speaker B: Yes, it's a way of being.

Like a really active curiosity. And that means that you can turn yourself, Sasha calls it, into a truffle pig for substance. You know, you're kind of always burrowing for the most interesting things you can find in any domain. Speaker A: You've pointed out something really special, which is an apprenticing to curiosity in a way. Like an osmosis, like curiosity by osmosis. I think it's interesting too, like maybe the world has less apprenticeship broadly, but like so many things are like that. Like we all have the experience of like the older kid or the older sibling or whatever, and you want to like what they like for a little while.

And then, and then by the, or, or the musician who's trying to sound like somebody and ends up sounding like themself. I don't know if there's enough conversation about that part of the taste thing though, which is so much of it is relational. Absolutely. In part because you're kind of like, boy, there's people you admire or respect or whatever, and you're like, you want to— part of it is even just getting closer to them. And then by doing so, you also get to like see through their eyes. And that's a really cool thing.

Speaker B: It's a very human experience, right? Because I think, and I guess our culture moves in waves and, you know, we're in America and America has a very particular relationship to individuality. Yeah. This is just the natural state of aging as a human or like becoming a human, right? Everybody has influences. You know, you start with your parents, your peers and such. Um, but what's so interesting is everybody I know who's amazing at whatever it is they do is pretty explicit about their influences, whether that was, as you said, an artist wanting to sound like somebody else, um, or just being incredibly inspired by their style of singing, their way of performing.

Um, and then eventually finding their own. I think it's really interesting, as you said, um, that there is some sort of disdain for people just admitting that in fact, yes, I'm heavily influenced by these 7 people. Speaker A: Of course, I'm not perfectly original. Speaker B: And this is just like, this is the experience of being human, right? I've been, I've been completely influenced by you since we've been friends, and I would imagine the other way. But yeah, I feel very shameless about this. But to your point, I think the ability to— I think it's what's really hard is choosing your influences and choosing what to ignore and choosing what gets right access.

To what I think about any given thing. And maybe that's the hard thing. Speaker A: That's a really refreshing answer. Speaker B: But maybe more interesting than any of that is, can you deploy your taste? Speaker A: Mm. Speaker B: And that is the thing that I think is the hardest, right? So you can spend years just watching all of these people that I just mentioned do things. But at some point, I became the commissioning editor of Stripe Press. And when you get there, ideally what you can do is use this knowledge, use this judgment that you've accumulated accumulated over the years to make decisions about what to create or in my case, what to commission.

Right. And so I can pretty instantly, if I read a proposal, tell you and I don't need to like read it 5 times to figure out that's a Stripe Press book or that's not a Stripe Press book. Right. Yeah. Speaker A: That's a really refreshing answer. Speaker B: But maybe more interesting than any of that is, can you deploy your taste? Speaker A: Mm. Speaker B: And that is the thing that I think is the hardest, right? So you can spend years just watching all of these people that I just mentioned do things.

But at some point, I became the commissioning editor of Stripe Press. And when you get there, ideally what you can do is use this knowledge, use this judgment that you've accumulated accumulated over the years to make decisions about what to create or in my case, what to commission. Right. And so I can pretty instantly, if I read a proposal, tell you and I don't need to like read it 5 times to figure out that's a Stripe Press book or that's not a Stripe Press book. Right. Yeah. Speaker A: There's some kind of like high-dimensional algorithm that you have developed over a long period of time that might not even be like super easy to put into words, but it's clear.

Speaker B: Yeah. Speaker A: Like when the input comes in, it's not easy to put into words. Speaker B: And I think that's why it's like tacit knowledge, for example. I would tell you that if you look in our catalog, people we've either published or are about to publish. So Nadia Aghbol, who wrote Working in Public, Brian Potter, who wrote The Origins of Efficiency— it's not out yet— and Stuart Brand, who wrote The Maintenance of Everything. They're all authors in our catalog. They are all doing a very similar thing. They approach their work in the same way.

But it would take me some time to explain that to you. Speaker A: I totally connect to this because I have had the same experience with the podcast. Speaker B: Yeah. Okay. Speaker A: So it's like something I have sort of groupings like you just described. Obviously all the Stripe Press authors aren't maybe in the same group, but I've noticed these almost like retroactive patterns that maybe I saw some element and sometimes there's overlap. Nadia, who you mentioned, I recently interviewed. Yancey published her book. There's, there's direct connection. There's also just these sort of like threads that are connecting in hindsight as they come together.

The, the, um, one of the things I've told people about, like how I choose people to come on the show is just if I, if I threw a dinner party with all the previous guests, could, could this person, would this person be a good add? Speaker A: I totally connect to this because I have had the same experience with the podcast. Speaker B: Yeah. Okay. Speaker A: So it's like something I have sort of groupings like you just described. Obviously all the Stripe Press authors aren't maybe in the same group, but I've noticed these almost like retroactive patterns that maybe I saw some element and sometimes there's overlap.

Nadia, who you mentioned, I recently interviewed. Yancey published her book. There's, there's direct connection. There's also just these sort of like threads that are connecting in hindsight as they come together. The, the, um, one of the things I've told people about, like how I choose people to come on the show is just if I, if I threw a dinner party with all the previous guests, could, could this person, would this person be a good add? Speaker B: Can they hang? Speaker A: Like, that's basically the only codified version of it.

But it's a, it's very similar to what you say, which is I actually do have a clear, I kind of know yes or no, but I can't really tell you why. Speaker B: Exactly. Speaker A: It's the same type of thing. Speaker B: It's this kind of automatic judgment. And, you know, you could, you could really spend, we could spend half an hour just talking about why developing taste fails for one reason or another. And I have some theories about that in certain instances, but Yeah, at this point it's kind of this automatic judgment and it's great because it saves me time.

I don't have to think for long periods of time about whether or not this person belongs in the catalog. It's always pretty clear. Speaker A: One last thing on this that I really admired in your, your answer is the part of the taste conversation that most comes up is sort of like, does somebody have good taste? It's this sort of about hindsight evaluative is their evaluation ability good? And you didn't really talk about that. You talked about the thing on both sides of that, which is inputs and influences all the way back to your dad's influence on your music, which is actually how all taste is developed, whether it's by osmosis or just what we read, where our attention goes.

And then you talked about deploying taste, actually doing things with it. Speaker A: One last thing on this that I really admired in your, your answer is the part of the taste conversation that most comes up is sort of like, does somebody have good taste? It's this sort of about hindsight evaluative is their evaluation ability good? And you didn't really talk about that. You talked about the thing on both sides of that, which is inputs and influences all the way back to your dad's influence on your music, which is actually how all taste is developed, whether it's by osmosis or just what we read, where our attention goes.

And then you talked about deploying taste, actually doing things with it. Speaker B: And I— Speaker A: my sense is that's one of the reasons that I think the taste thing has become so sort of like overblown and almost like empty. Is that it's actually just like, does Tammy have good taste? What does that mean? Good taste in what? And that's way less interesting than like, what are the things, what are the inputs that are feeding me? And to extend the taste word to like what it literally means, which is like, what do I like?

Am I good at understanding what I like? And then what am I going to do with that information? What am I going to eat next? Speaker B: Exactly. Because I don't think we need another cultural critic. I think we have enough. And like, I am, I think, increasingly uninterested in cultural analysis and way more interested in can you deploy— it's like when people joke, you know, If you're so smart, why aren't you happy? And it's like, if your taste is so good, why aren't you deploying it anywhere? Speaker A: That's heavy.

Speaker B: And that's a big challenge, right? Learning how to, how to move from I know what I like and why I like it to in fact, I can, I can take what I like, all these patterns that I've learned, all this judgment that I've developed for however long period of time, and I can use it to make decisions about what to create or in my case— Exactly what to commission. Speaker A: That's heavy. Speaker B: And that's a big challenge, right? Learning how to, how to move from I know what I like and why I like it to in fact, I can, I can take what I like, all these patterns that I've learned, all this judgment that I've developed for however long period of time, and I can use it to make decisions about what to create or in my case— Exactly what to commission.

Speaker A: It's really cool. Speaker B: And that's, I think, what's so— what makes that tacit knowledge and not explicit knowledge. We'll come back to this, but Cedric Chin, I think, I think he is probably the best person writing today about tacit knowledge. He is a— well, he's a lot of things. He's a writer, a business analyst, a consultant based in Singapore. And he describes tacit knowledge as the process of moving from conscious incompetence to conscious competence to unconscious competence. And, you know, that's what we're talking about. This, like, can you make these snap decisions?

Can you figure out what— how to deploy something without needing to go through this laborious mental process? And so, yeah, can you deploy it is basically all I care about these days. Speaker A: That last bit is the sort of master who can't even necessarily explain why they do what they do. Yeah. Speaker B: Yeah. Speaker A: You've said that books we publish are a vote for ideas we care about and what people see, their frames of reference really affects what they do or don't create. So in that theme of deployment, Stripe Press, you've talked about this plenty, has sort of two tracks.

One is what you call Turbentine, this very like pragmatic, here's how to do things, and then you have a kind of a more broad theme of ideas that are important for the world. How do you think about that kind of deployment, that taste in ideas that matter, and why is that such an important thing for a, for a tech company to be doing? Speaker B: I think a lot of this goes back to who we're talking to, and again, just to kind of continue on the last conversation, and who we're not trying to talk to.

So like, I'm pretty uninterested in the median anything, but I am hyper-obsessed with the the kinds of people who are like you, right? So people who are obsessed with and working in some way or another to extend the frontier of human knowledge or human capability, who have, you know, a deep love for people, who think that people are incredibly— have sort of an incredible capacity to create and are themselves kind of, again, doing that. They tend to be extremely curious. They can tell when you're kind of feeding them nonsense. They have some level of discernment, which means you can't just feed them anything.

They are— they tend to be pretty global and whatever. Anyway, I'm hyper-obsessed with them because those kinds of people's feedback loop between idea and execution tends to be quite short, right? Yes. They think about something and they go do it. And it doesn't mean it's perfect every time. But Nadia talks about this. Speaker A: Yes. Speaker B: And it was my favorite part of the blog post that she wrote when she announced to the world that she'd written Working in Public. She just talked about how she's obsessed with writing that makes things happen.

Speaker A: Yes. Speaker B: And us too, right? Speaker A: And so ideas are high leverage for this demographic. Speaker B: Totally. Right. And you can just incept these memes. Again, they may or may not be good memes, but they're so sticky and they're particularly sticky in this environment. Just to take one that is just kind of been beaten to death. You can just do things. But like, if you really internalize the idea that you can just do things, that means that, you know, suddenly you don't make excuses for things.

Suddenly, you know, things that don't seem possible become possible, whatever. Um, We'll have to come back to why that phrase seems to be mostly deployed in service of antisocial actions later. And like, that's what I really care about, right? I want anything that makes individuals think of themselves as actors who can kind of mold the world. Yes. That doesn't necessarily always mean on a grand scale, but, you know, people who— people— anything that offers people an internal locus of control. Yes. And then anything that— Speaker B: Totally. Right. And you can just incept these memes.

Again, they may or may not be good memes, but they're so sticky and they're particularly sticky in this environment. Just to take one that is just kind of been beaten to death. You can just do things. But like, if you really internalize the idea that you can just do things, that means that, you know, suddenly you don't make excuses for things. Suddenly, you know, things that don't seem possible become possible, whatever. Um, We'll have to come back to why that phrase seems to be mostly deployed in service of antisocial actions later.

And like, that's what I really care about, right? I want anything that makes individuals think of themselves as actors who can kind of mold the world. Yes. That doesn't necessarily always mean on a grand scale, but, you know, people who— people— anything that offers people an internal locus of control. Yes. And then anything that— Speaker A: the crux of it is The world isn't happening to me exclusively, but I can actually assert myself upon the world. Speaker B: That's right. And I think one of my favorite books in our collection, and we won't spend this whole conversation talking about books, is The Art of Doing Science and Engineering by Richard Hamming.

And I think sometimes people will look at that book, one, it's a bit of a cult classic, which is so funny. I'd never heard of Richard Hamming before I came to Stripe. And when we published it, I was genuinely shocked by the reaction that so many people had. So many people who are responsible for some of the most load-bearing pieces of either digital infrastructure or companies, what have you, see him as just an incredibly important frame of reference. So, the last chapter of that book is a chapter called "You and Your Research," and it's at this point a talk that I return to, I would say, at least once a quarter.

And what stuck with me is that that message felt like the exact opposite of a lot of the, I want to say, cultural programming that I was exposed to growing up. You know, there is a lot of messaging that will come to you as a young person, or, you know, in my case, as a young woman of color, Black woman, whatever, that I don't think is malicious, but that wants you to kind of think of yourself as a person on whom things happen or to whom things happen. And there is so much media and so much, again, like, programming from all corners that is just— that asks people to demand less of themselves, or, you know, to just think of think of themselves and think of the world in terms of systems, in terms of these impersonal, cold systems which determine everything.

Speaker A: Yeah. Speaker B: Yeah. Yeah. Speaker A: It's the man. Yeah. Speaker B: It's the man. It's those politicians. It's those people. It's them. It's always them. You and your research and sort of by extension, The Art of Doing Science and Engineering is actually a set of lectures that he gives during his time as a professor at the Naval Postgraduate Academy. So he's telling them, I want you to be incredibly serious about your own life. I want you to take your dreams, your aspirations extremely seriously. And, and that all starts with asking the right questions about the world.

You're not likely to get anywhere if you don't even ask the right questions. I want you to see nothing as more important than whatever your personal mission is in life. And there's just a sense of seriousness, of expectation that emanates throughout all the pages. And you read it even, you know, this is, we're now 30+ years past him writing the book. You read it and you immediately feel convicted. Speaker A: Ah, that's the best kind of writing. Speaker B: You know? And it just, it holds up. And tons of people that, again, I think I just like really respect and I've learned a ton from, have that as a kind of formative essay for them.

And I do too. And so it's my favorite essay to give to young people. We have a zine version of it. I love giving it, especially to teenagers, you know, you should take yourself seriously. And again, I don't want to make it seem like there's just all— I was totally, totally defenseless in the face of all this messaging that I got as a kid. But, you know, I grew up in a suburb of Dallas. The— my biggest frame of what success looked like to me was just like being a doctor, being a lawyer, being an engineer.

Now, some of that is also being Nigerian, but yeah. Speaker A: I was rereading, uh, On Self-Respect by Joan Didion, and there's a line in there where she's talking about character, and it's exactly what you're saying. She says, character is taking responsibility for your own life. Speaker B: People with self-respect know the price of things, she said. You know, heavy. They don't, they don't engage in an affair and then, uh, and then like, you know, feel like, oh, it was you that made me do it. You know, they don't throw rocks and hide their hands.

They know the price of things. Speaker A: So good. One other part of, of the taste kind of Stripe Press thing that might seem trivial, but I, my sense is you take very seriously, uh, is aesthetics. Um, I suppose my question is what kind of heavier lifting or deeper impact do you think aesthetics have? Speaker B: I really do think at the end of the day, people judge books by their covers. I have to say that. And I think, okay, so the reason to make the books beautiful, the argument that we're making, right, with Stripe Press existing is that we think that these books are, and the ideas contained within them are important enough that if you internalize them, they will change your life.

Whether that's you and your research, whether that's a journal about the making of a video game, whether that's if you're starting a business. You know, Claire Hughes Johnson's book about management. We think that these ideas are worth the $30, $40 that you're going to spend to buy the book. Speaker A: And much more than that, a bunch of your time. Speaker B: Right, exactly. I mean, the median page count is what, 300, 400 pages? And so if we think that, then it is, I think, only fitting and only right that the container for those ideas is also something that somebody, a specific person, a specific group of people when it comes to the Stripe Press design team put a lot of time and care into.

Speaker A: And much more than that, a bunch of your time. Speaker B: Right, exactly. I mean, the median page count is what, 300, 400 pages? And so if we think that, then it is, I think, only fitting and only right that the container for those ideas is also something that somebody, a specific person, a specific group of people when it comes to the Stripe Press design team put a lot of time and care into. Speaker A: Yes. Speaker B: They're working just as hard to make sure that the, the outside matches the insides.

And I also think that there's just a lot of ugly stuff in the world. I forget who said this, but I think it is your responsibility as a person to just not add to the amount of ugly stuff in the world. Speaker A: Yes. Yeah. Jon has that amazing line about the world being a museum of passion projects, which is kind of the other end of that. Speaker B: That's right. Everything around you is— Speaker A: It doesn't happen by like, it doesn't happen arbitrarily. It happens because a few people really care.

There's, on this note again of tacit knowledge, there's a lot of knowledge, even very practical knowledge in the world that isn't written down. Speaker B: Yeah. Speaker A: But there's also a lot of things that aren't written down. For good reason. How do you actually parse it? Maybe especially on the sort of like, here's how you do things, pragmatic advice, Turbentine idea. How do you parse what types of things are worth codifying and sort of in some cases, some of the books are like, here's the sort of de facto, here's how you should think about scaling an organization or here's how you should think about building a startup.

How do you think about— there's like, um, there's high stakes there to say like, this is, this is the go-to advice for how to do something. Speaker B: Yeah, that's right. And so maybe the most important thing there is picking the right person to author that book. You know, there are a lot of books, for example, out there already about scaling companies, thinking about, you know, people development. But maybe one of the reasons why Claire— Claire Hughes Johnson, for anyone who hasn't read Scaling People— was such a great person to write that book is that she is who a lot of people wish they had when they start a company.

Because if you're a founder, right, you're focused on a couple of things. You're focused on refining the product, right? You need something to sell people. You want to make something people want, as they say. And then you have to go acquire customers. But in the best case scenario, if you're starting a company, things will go so well that you've got to hire. Speaker A: Yeah, yeah, yeah. Speaker B: And by the time you start having to hire people, it's probably too late. Speaker A: The plane's in the air. Speaker B: Exactly.

Exactly right. And so Claire is one of those people who just thinks about these things fundamentally. You know, she just really loves people. She's kind of the heart of Stripe. And, and she's happened to see these dynamics, right, building and scaling an organization at two really important companies over the last, you know, 20 years. One was Google. You know, she was at Google before Google was even public. And then, of course, at Stripe, when Stripe was, I think, fewer than 150 people. Speaker A: One question I would have here would be, that makes perfect sense.

And yet there's also a lot of people who are effective who are bad at communicating their ideas. Speaker B: This is true. And actually it's something we struggle with when it comes to picking Turpentine people. So again, this is the tacit knowledge where if A, but B, but if C, then D. And so this is C. And yeah, some people, it's, it's not always the same people who are great at doing and teaching, right? Because often people who are really good at a particular thing have no idea how to talk about it.

Now, of course— Speaker A: One question I would have here would be, that makes perfect sense. And yet there's also a lot of people who are effective who are bad at communicating their ideas. Speaker B: This is true. And actually it's something we struggle with when it comes to picking Turpentine people. So again, this is the tacit knowledge where if A, but B, but if C, then D. And so this is C. And yeah, some people, it's, it's not always the same people who are great at doing and teaching, right?

Because often people who are really good at a particular thing have no idea how to talk about it. Now, of course— Speaker A: And by the way, as we've talked about in the past, that generalizes from company stuff to like, I don't know, the master craftsman. Speaker B: Exactly. But one of the constraints, and this is a nice thing about working at Stripe Press, we just have a lot of constraints. And one of them is that we are not going to get anybody to write a turpentine book that isn't a deep practitioner.

And so, yes, it is the case that there are plenty of people who have never been a COO at a company who could write in really convincing terms and write really rigorous, excellent books about what it is to kind of scale. But it's just not an option for us, right? And so, you know, you need an Elad Gil. You need somebody who has both been a founder, been an executive, and then invested in and advised a ton of really successful companies. You know, if you think about Elad, he has been on the cap tables of so many of the most important companies the last, you know, 15, 10, 15 years.

And you don't acquire that kind of portfolio by accident. And a lot of people want to work with him because he has seen companies at all different stages. He knows what it is to constitute a board. And, you know, as is really important right now and it's kind of floating around how to exit, whether that's going to be a merger or an acquisition, an acquihire, or going public. And so, yeah, for us it just isn't an option, even though there are plenty of people who are excellent at describing a discipline and teaching it who haven't necessarily done it themselves.

Speaker A: Another kind of more legible part of the world that anyone who's ever met you would assuredly agree you embody is an idea that I'm going to collapse into charisma. I think it's a lot more than that. And there's A lot of complexity here, but you are a very charismatic person. You've said that you get lucky a lot. Can you explain why? Speaker B: I don't know. How do you answer this without sounding like the most annoying person on the planet? Speaker A: I'll tolerate it. Give us some theories.

Speaker B: Okay. I have some theories. Yeah. The first is that I'm a middle child. Speaker A: Mm. Speaker B: And the plight of the middle child is such that there's always somebody a little cuter than you and somebody who's been doing this longer than you. Speaker A: It's brilliant. Yeah. Speaker B: So you gotta stand out somehow. Speaker A: Fuck off, bitch. Speaker B: See? And so the blight of the middle child, uh, is that you have to— Speaker A: Constraints are great. Constraints. Necessity is the mother of all inventions.

Speaker B: So true. And my parents constrained me. Why? This kid who's cuter than me and this guy who's been doing it longer than me. Um, and I think, yeah, I think this probably started from a young age. Speaker A: Maybe that's the, that's the root of it, to have to figure out how to get people's attention or people to like you. Speaker B: Yeah, but maybe I've always been really curious, and maybe the thing that I've always been most curious about is other people. I just, I really love people.

And, you know, there could be a lot of reasons for this. Maybe one reason for it is just like we share a religious background, you know, there's just like a commandment to love people as yourself, and I mean, that's just the commandment. But maybe part of being— getting lucky is making it easy for people to bless you or something. My— one of our good friends, Alicia, calls it flirting with the world. Speaker A: Amazing. It's so good. There's a notion around charisma that I really like, which is that it's much more about how you make other people feel.

Yeah, I love the flirt with the world frame. Other people might have a connotation around that word that they struggle with at times. You've also framed this as delightfulness privilege, which is an amazing version of it too, that I think maybe has less baggage. And the reason you're lucky, you've, you've talked about like the people who seem to meet good fortune wherever they go. As someone who knows you fairly well, anyone who ever interacts with you gets this like warmth, this like dial of sun that's turned on. And so it's like, I can, you can meet you once and be like, oh, I get it.

Like, at least I get a seed of it. Can you talk a little bit more about delightfulness privilege? Speaker B: Uh, I think that, um— Speaker A: You're playing on pretty privilege for people who are underground. Yeah, yeah. Speaker B: And this is not the same thing. Not the same. I think maybe probably what it is is there's, like, a ton of social infrastructure which seems totally unimportant but is in fact everything. And that means that actually The way that you show up when it's time to go through the TSA line at the airport, or the way that you tend to react when your food was kind of cold, um, or the way that you tend to react when you are at a party, you're hosting a party and somebody comes in that doesn't know anybody and how you decide to integrate them or not.

Yeah. Right. These kinds of things, um, are like a social lubricant that basically determine how everything runs. The most recent guy that I was dating, we would go to restaurants, and something that started happening to us pretty early on was just being given free things constantly, like free glasses of champagne. It happened like 4 or 5 different times at different restaurants in different conditions. It's like, the question is, why does that happen? Yeah, maybe the answer— Speaker A: maybe you're just lucky. Speaker B: Maybe we're just lucky. Speaker A: I don't think so.

Speaker B: Maybe it's like niceness. Okay, so And again, I find it hard to talk about this because maybe somebody's takeaway would be, this is how you interact with people to get stuff out of them. But instead, it's just— it just happens to be the case that, for example, at a restaurant— I used to work in a restaurant. Have you ever worked in a restaurant? Speaker A: I worked at Chick-fil-A. Yeah. Okay. Speaker B: So it's not quite the same thing, but I was a hostess and then I was a server for a little while.

And you know what it's like to have had a really long shift, a really long day. You're fighting with your partner. You're— you've got a headache and you have to keep waiting on people. And it's like 9 o'clock at night. And, you know, somebody comes in and they're just like, I really don't want to deal with you. I just want you to bring my food, take it away, and like hopefully don't interact with me otherwise. That's just not my approach to eating at a restaurant. So I will always ask somebody, for example, what's your name?

And it's— and sometimes it will throw a server off because they'll think that you're asking for their name in case anything goes wrong, like as an insurance policy. Speaker A: That says a lot about society. Speaker B: I guess it like happens infrequently, you know, and, and Tammy is only one step away from Karen. So you don't know, you don't know what's gonna happen. But instead it's just like, actually, I'd like to be able to say the name of the person that I'm gonna be interacting with for 2 hours. Yeah.

And, um, and so I think that maybe what we're describing is it could be called niceness, but it becomes automatic. And I think a lot of people who exhibit this, we have a lot of friends for whom something like this is true. These like micro interactions compound like anything else over time. And I guess it produces a kind of effect that is what I would say is luck. Speaker A: I wonder if part of this is this notion that like we've all just gotten kind of cynical, like, oh, you want my name?

What are you going to do with it? Like you're going to complain to my manager or whatever? Speaker B: Well, like every micro interaction you have with people kind of feeds one perception of people or another. I also think something that's really important, and I'm not sure I have this, but I think there are a lot of people that we know who have this. There's one version of charisma that's like the cliché. They just light up a room. There's, like, some subset of people who are able to capture and sustain attention wherever they go.

And then there's another kind of person, and sometimes they're the same, who just makes you feel— another cliché— makes you feel like you are the only person in the room and, like, it would be illegal for them to take their attention off of you. Right? And that's so powerful. And every time you have an experience like that, it's just the most meaningful thing in the world. Speaker A: Yeah, no wonder those people, by the way, end up being successful. Speaker B: Absolutely. Speaker A: Turns out everyone who interacts with them feels important and special and liked.

Speaker B: Like, and it's like particularly impressive when you see this happen at a scale where they're like the kind of person who, because they're so successful or whatever, they just are used to people deferring to them, being way more interested in them than, you know, they would expect to receive reciprocally. And I think you and I both know people for whom they're quite successful. There used to be people deferring to them, but in fact, they are way more interested in you and way more curious about you. They'd rather ask you questions than spend any amount of time, you know, talking about their business.

Speaker A: It's a way of being versus this, like, path to success. Speaker A: It's a way of being versus this, like, path to success. Speaker B: Yeah, absolutely. There's some months ago I read Virginia Woolf's essay on Montaigne, and in part of the essay, you know, she talks about the way that he lived his life. But in some portions, she starts talking about his orientation towards people and by extension hers. And, you know, she kind of considers it a sort of social deformity. If you're the kind of person who can't laugh easily with your neighbor, who can't make conversation as easily with the banker as you can with the plumber.

And she sees this as like a critical part of being a human being, which I, I tend to agree with. Speaker A: I have that quote right here, and I wrote it down because I think it's like the most distinctly Tammy thing I've ever read. I'll read that. Just the— this excerpt in particular, I felt like, is the thesis statement for your life. To communicate is our chief business. Society and friendship are our chief delights, and reading not to acquire knowledge, not to earn a living, but to extend our intercourse beyond our own time and province.

Why? Yeah, why is it so important to live a relational life? Speaker B: Well, I don't think that you can live any other way and live healthily, right? I don't want to get emotional, but I think that part of— we were joking about this the other day We have— we are friends, but we also have this, like, web of friendships and people in common such that at any given time, two of these people are talking to each other or three people are plotting some trip or whatever. And it's really lovely, right?

Because there's this interlocking web of people, but also— and that's really— that's really cool when you— you guys, you, Devin, and Anne and some other folks were just in Europe together. But it's also really cool when you have something go wrong in your life and you just need your village around you. Or even better, I think, when you're needed, right? It's one thing to kind of need people and have them there. It's another thing to get the call from somebody that loves you and says, "Hey, I really need you right now."

And I think, you know, I'm not going to say anything that other people who've studied this longer, who are more articulate, haven't already said. But there is, I think, this just breakdown of community as understood this way, you know, these, like, thick connections. And I feel really lucky that that's just not the life that we live, that we have, you know. And that doesn't mean having, like, 40 best friends, but just having a core of people that, you know, you can rely on, that rely on you, that expect things of you even.

And maybe my favorite person who writes about this, and maybe yours too, is Ava. You know, she has this very ambitious model of friendship. You can, for example, she's constantly telling me, you know, me not living in San Francisco, and you too, by the way, is like ruining her life. You can actually demand that your friends live near you, you know? And I love that. There are a lot of people who just uh, who think— who I think think they prefer to live a life that doesn't require them to have obligations to anyone.

But I think when it really comes down to it, every— everybody kind of wants to get the call. Speaker A: I think, I think, I think there's a quote from Ava's blog or Substack where she's talking about you. She says, T and I said we'd be friends at Saint-Urdine in 2023. It was springtime and she told me she decided to be vulnerable with me starting now and that we are going to be close— that we were going to be close. I was a little bemused because she had not so— she had not so far been particularly vulnerable at all, and I was wondering if the change really could just happen like that or how it would feel.

But it really did just happen like she predicted. I moved to California. We hung out when we visited each other's respective cities. We became friends. In the Waymo on my way to see her yesterday, I was so excited I had heart palpitations. There's something in which— Speaker B: just, oh, I love her so much. Speaker A: There's something inside of this, though, that you might not like this, for at least the verb, uh, the words I'm going to use here, but there's, there's like a social agency, maybe, or at the very least a willingness to impose your will on the world socially that is inside of like, hey, sorry, whether you like it or not, we're gonna be friends now.

And then I think that also obviously ties to something else you were saying that you're keen to say, which is like the obligation is the gift. But yeah, can you talk about like What's inside of telling somebody, hey, we're going to be friends now? Speaker B: Well, honestly, I think that was a little obnoxious of me, but I basically— look, what had happened was we'd had enough interactions to that point. We had people in common that kept telling us individually, you two would really like each other. And I was just like, all right, look, I'm ready to go all in here.

You know, I think that— I think that we're going to be friends for 50, 60, 70 years. So we should just start now. Right? Might as well start now. I mean, we could start tomorrow, but we could start now. And now, of course, that doesn't work unless you have these, like, repeated interactions, right? Speaker B: Well, honestly, I think that was a little obnoxious of me, but I basically— look, what had happened was we'd had enough interactions to that point. We had people in common that kept telling us individually, you two would really like each other.

And I was just like, all right, look, I'm ready to go all in here. You know, I think that— I think that we're going to be friends for 50, 60, 70 years. So we should just start now. Right? Might as well start now. I mean, we could start tomorrow, but we could start now. And now, of course, that doesn't work unless you have these, like, repeated interactions, right? Speaker A: Where— Speaker B: so it means, for example, things like you're not every time you go to dinner going back and forth about how to split the bill.

It's just like, you get it this time, I'll get it next time. And there's this, like, reciprocity there. But also, you know, something that I think was really beautiful and maybe is the best way to articulate it comes from Warren Buffett at the 2024 Berkshire Hathaway annual meeting. This really sweet— this kid couldn't have been more than 10— comes up to him and he asks, you know, what would you do with one more day with Charlie? And, you know, he says, I would probably spend it the way I spent every other day with Charlie.

You know, they were kind of constantly in contact, even if they weren't in the same place. And he said to the young person, he said, "Look, if you find somebody like this, my suggestion to you is that you, you know, kind of lock it down and you try to meet with them as often as possible." And I guess that's my model of friendship, right? I happen to live abnormally close to my village here in New York. And then, you know, it's funny that when I go to San Francisco, there really is like one square mile that most of my people live in.

And Yeah, I don't know. I don't know what's behind that. I also think maybe part of it is cultural in the sense that I have a really big family, a really big extended family, but I didn't grow up around a lot of them. But there is this expectation that, for example, if I were traveling through London and I needed to, you know, you got— you have a cousin in every city, or something that's like a cousin functionally in every city. And that's really beautiful. And, uh, I think I think really lucky.

Speaker A: What do you think? How would you describe your taste in your friends? Or what types of qualities? What, um, what gets somebody in? Speaker B: Oh my gosh, dang, what does get somebody in? I think this is the most important thing. This, like, we're not opting out of this friendship, you know. You'll, you'll hear, and I think increasingly these days, about like friendships just going wrong or friendship breakups. And I think nothing is harder than a friendship breakup. Speaker A: They're almost harder than Angie Jovian and Sharon, if you've never seen it, crazy friendship.

Right. Speaker B: And he just decides one day, I just don't like him anymore. Right? Like, I just, you know, it's like a motif that's repeated, especially through the first part of the movie. I just, I just don't like him anymore. And I think this idea is maybe most important to me. We're not opting out, which means that if we are close friends, we can go through as many ruptures and repairs as we need to. And kind of paradoxically, it makes it less likely that you run into these arguments But like, this is, I think, the kind of consistent orientation, I think, to all of our friends, because again, we share a lot of these people in common.

Yeah, you don't get to opt out of this friendship. We're doing this for 60 years. And what does that actually mean practically? Well, that means I'm really invested in your life. I'm really invested in your parents, how your siblings are. I want to know your partner. You know, eventually when we're all married, let's say we, we have this kind of, on some level, group orientation towards each other such that it even extends to how we date, right? Because we all want to date partners who don't necessarily, like, need themselves to be all of our best friends.

But the idea is that if there's ever a day that, like, I'm sick, let's say, and you and your wife needed something, well, I need him to go in my place, and vice versa, and you would do the same thing. And I think that this changes every interaction because, one, it means we don't need to be next to each other all the time, although we are in often pretty regular contact, but that will change as, you know, people have kids. And a lot of my best friends in other cities, whether it's in

C. or Dallas, already have families with 2, 3, 4 kids. And you kind of see this— it's not, it's not a perfect one-to-one, but, you know, you see the same orientation where if I'm in, there's like 3 or 4 people that I have to see every time. And that even if I go a year without talking to them, if I really needed something, they would be there and vice versa. Speaker A: You brought up Charlie and Warren, and you also talked about sort of this, this web of people. There's an idea that I think applies to friendship, but I think it also applies to relationships professionally, all these things.

And you've described it as the real thing people should take away from Warren and Charlie, not 50 years of compounding, which is a seamless web of deserved trust. Can you describe that phrase? Speaker B: Well, it's not a, it's not a phrase that originates with me. It's a phrase that originates with Charlie. There are all of these invisible structures that we don't appreciate that are totally load-bearing. And one of those is trust, right? The idea that I can interact with you without having to negotiate every single interaction. Speaker A: Yeah.

Repeat iteration game. Speaker B: Exactly. I can live my life. I can do business with this person or in this firm and I don't have to constantly be thinking about, is this person going to cheat me? Do they mean what they say when they say it? And so on. And this scales all the way up and down, right, to personal relationships, but then also again to, um, like entire societies. How easy is it to get things done? Do you think that most people can be trusted? And of course, the seamless web of deserved trust means being the kind of person who, you know, all of these good things can also be applied to.

You know, you say what you mean, you do what you say you're going to do, all of those things, right? You're the kind of person that makes it really easy for people to interact with you and not to kind of backtrack. But part of like this delightfulness thing is that, right? Are you the kind of person that's easy to interact with? Are you predictable? Speaker A: You know, a great— a different version of these, like the other end of the spectrum maybe. But you use the frame load-bearing. Another thing you've talked about that I really admire in you is your appreciation of small talk, which is— Speaker B: I love small talk.

Speaker A: It's like the exact opposite end is it's like it has none of the weight of all the friendship stuff we were just talking about. And yet you've made the case that it's doing a lot of work in the background too. Speaker B: Yeah, I think I'm small talk's strongest soldier. I will go to war for small talk. Speaker A: Give us the case. Speaker B: There are, I think, a lot of reasons to— I totally buy a lot of the reasons that people dislike small talk, right? It's a waste of time.

It's not going to get you anywhere. It's like, I don't really care what your favorite color is. Okay, fine. Speaker A: Well, sorry to interrupt you one more time. I would I would also add that there are a lot of people who would hear much of what you just said about relational, living a relational life, even being charismatic or flirting with the world and agree. And I suspect also a large percentage of those people who otherwise put a lot of weight into relationships think small talk sucks or doesn't matter. Speaker B: Yeah.

Speaker A: So there's an interesting sort of dichotomy there. Speaker B: Yeah. And I hear that and I understand that too. But again, I would argue that it's this like invisible substrate that matters a ton. Like, in a really stupid— you can't build a skyscraper without a foundation, right? Let's take it. Let's just like take it in a couple of domains. In business, for example, you know, you think about like, I'm trying to do a deal here. Again, I really don't care what, you know, how your commute was on the way over.

But part of what people are doing when they're trying to— when they're employing small talk in business, right, is I'm trying to see if you know how to read social cues. I'm trying to see if you know what appropriate disclosure looks like when you're just meeting people. And beyond that, I'm trying to see if you're the kind of person I want to be around for extended periods of time, right? Like, that's what I'm doing when I'm doing small talk in business. Speaker A: And as much as you're— that, that framing is almost like testing for something, you're also doing— it's like a compatibility check.

Yeah, you're actually trying to create ease. You're trying to— Speaker B: it's an invitation as much as it is a question because I'm trying to find, you know, points of compatibility. You're trying to find these like leverage points by which you can go deeper, you know. Um, this— oh, I don't want to— I don't want to be too critical here, but one of the things I struggled with early on in my time in SF before I was living there— um, I only really lived there for 6 months, but the way I make it sound, it's like, oh, I'm a veteran.

I imagine you don't have any questions about SF versus New York on this list. I hope not. Speaker A: But, um, no, no, you— Speaker B: like, there's there was for a time this like real habit that people had of like, I just want to know. I don't want to— I don't want small talk. I want big talk. I want to know, you know, I need to know what happened to you at [redacted address] that you are. And it's like, hold on, wait, we don't know each other. Speaker A: We're at a house party.

Speaker B: Right, right. Or like you're on a first date, right? Speaker A: Like, I'm guilty of this. Speaker B: Maybe I don't care what, again, your favorite color is, but you can't like build a relationship that lasts decades without like establishing this basic social trust. Speaker A: Like there's something inside of this too that is, it's, it's like proximity. Proximity is another form of this sort of like lifting that actually like a sign of a really great friend is not a great friendship, I should say, is not that you can sit and have a super deep 2-hour conversation.

It's that you can be perfectly comfortable in silence for 5 hours doing like driving or shopping for groceries or something. Yeah, it's both of those things. Speaker B: Tyler Cowen, when a friend of mine, Caleb Watney, and his wife, Katerina Watney, got married, for some portion of their relationship, it was long distance. And one of the things they referred to was Tyler Cowen's guide to long-distance dating. And one of the things he says is that you should, instead of trying to make every time you're together this like unique, distinct experience, you should do a lot of mundane stuff, right?

Like, because what is marriage if not eating dinner together every night? Like, do I think I could eat dinner with this person for a long time? Speaker A: Yeah, it's like, give me the most boring environment setup possible? And am I still engaged? Speaker B: Does it still work? Yeah, I will say there's also probably, and this might seem kind of abstract, a sort of societal layer to small talk or societal piece to small talk that matters a lot. So like America has a lot of like heterogeneity in the population, right?

Which means that things like small talk are actually like this important social ritual that, for example, maybe Europe doesn't need because there's like a lot more homogeneity in an individual population, right? Because small talk is how you kind of establish between people who have very different, you know, cultural contexts, who are coming from a different place, that like, it's— Speaker A: we're on the same social kindling or something. Speaker B: Yeah, we're on the same team, you know. And it makes it— it makes— because it offers you a lot of these like low-stakes repeatable interactions.

And so, you know, where I'm from, the South is kind of famous for this level of hospitality, right? Speaker A: Because yeah, inside of this too is manners and politeness and etiquette. They're all kind of in this bucket. And all of those things, it seems people are like, do we really need— it's like a chest and fencing of these sort of social— Speaker A: Because yeah, inside of this too is manners and politeness and etiquette. They're all kind of in this bucket. And all of those things, it seems people are like, do we really need— it's like a chest and fencing of these sort of social— Speaker B: it's only when it's gone that you realize, in fact, again, that that thing which seems pointless, silly, is load-bearing.

Now, some people may listen to this and say you're overthinking it, which I'm fine, I'm fine if I'm overthinking it, but it does seem actually pretty important. Speaker A: There's a, um, one of my— one of the things I love your frame on is this, this notion that like we're also desperate for community And yet, like, we don't want any of the obligations that go with community. Applies to the friendship thing too. And yeah, I think that's— it feels heavily heavy in today's era. It's like, I want, I want, I want relationships and I want community, I want all these things.

And I also want to do it on exactly my terms with exactly what I want. Speaker B: Yeah. And the least restrictive in the way that asks as little of me as possible. I will say there's a flip side to these— what we're talking about when you have these shared social scripts. As they start to break down, as these start to not be universal values, you do see people really wanting to curate their own environments, right? One of the things I am really interested in is in the rise of private security.

And, you know, I used to work on charter cities. And what you'll see when you go to places like South Africa or Zambia or my home country, Nigeria, is Fundamentally, you live in the country, but you actually live in your enclave. Speaker A: Mm-hmm. Speaker B: So this part that you've been able to curate, right? You have your own security that the people who live there pay for. It's not the responsibility of the government because you can't trust it. And then you certainly don't want to kind of interact with everybody in the population because it's not a super high-trust population.

So in really low-trust areas, you basically have people who stay kind of in their clans. Mm-hmm. And then as it— as it sort of becomes higher trust, you can kind of trust more and more different kinds of people. You don't— you can interact with more strangers. You don't see this in places where you have a lot of low trust. And one of the things I'm— yeah, like I said, particularly interested in is just in the US in particular, just the rise of private security, because you can't necessarily trust that we're all following the same social scripts.

Or not just the rise of private security, but the reintroduction of things like members clubs or members clubs that already exist becoming a tier more exclusive because you have people who would actually rather not interact with sort of the median person. I think that this is unfortunate, but this is what happens when you lose these social scripts, right? A couple of months ago, or maybe a month ago, whatever, you saw the Uber Bus, the sort of Uber Bus, the fuss over Uber Bus, right? Like, well, so it's, it's like Uber carpooling or something.

Speaker A: It's the airport shuttle. Speaker B: It's not the airport shuttle. I think it's like, I think they're actually testing just like a bus, like a regular bus. Speaker A: Yeah. Uber invented the bus. Great. Speaker B: Right. It's like, congrats, you invented a bus. But you know what a lot of people were quick to point out was this isn't really a bus. This is the way that I can pay a little bit more to not have to deal with the dysfunction that comes with riding the subway, riding the metro.

If riding the subway was like a perfectly pleasant experience where I don't ever have to come into contact with people acting, you know, crazy or whatever, then you don't need things like a bus or, and then Yeah. Speaker A: It's the airport shuttle. Speaker B: It's not the airport shuttle. I think it's like, I think they're actually testing just like a bus, like a regular bus. Speaker A: Yeah. Uber invented the bus. Great. Speaker B: Right. It's like, congrats, you invented a bus. But you know what a lot of people were quick to point out was this isn't really a bus.

This is the way that I can pay a little bit more to not have to deal with the dysfunction that comes with riding the subway, riding the metro. If riding the subway was like a perfectly pleasant experience where I don't ever have to come into contact with people acting, you know, crazy or whatever, then you don't need things like a bus or, and then Yeah. Speaker A: The extreme version of this, by the way, is the culture of LA, which is you never drive, you never walk, you never take any— and in the implicit, as someone who lived there for so long and now lives in New York, and I love LA for a lot of reasons, but the implicit thing there is that I never ever have to interact with another person that I don't choose to.

And that is— when that is the fabric of society, I think it's not great. You— this is a great lead-in to the next thing I want to talk about, which is You use the phrase load-bearing a couple of times. You've thought about this a lot in the context of societies. Maybe the right place to start would just be, you've talked about, um, in healthy societies, I suspect, there's a scaffolding that allows us to move freely and safely, both in the social sense and in the sort of harder, more, more real, safe security sense, a hidden infrastructure there.

Can you talk about like what is being embodied in that sort of ability to move freely, what you mean by that? And we'll talk all about the implications in the social side and the security side. Speaker B: Again, I guess it's, does the— do the social conditions of wherever you live make it easier or harder for you to just go about your day as normal, to like live your generic life, right? You and I have talked about this before, but I feel like what we were discovering, at least if you let Twitter tell it, is kind of this like mass rediscovery of why these shared social scripts matter so much.

Speaker A: Yeah, another Cheston Fetz. Speaker B: Yeah, like it's not just politeness, but it's like, you know, it turns out that we don't all agree on— why shouldn't you take loud phone calls in public? Should you? Why should you, interpersonally, when you're going out to eat, why should you not negotiate back and forth about who's going to pay and maybe just take turns paying? Part of what's happening there is like, okay, in the, in the first example, you know, shared spaces require shared consideration. And same thing with the second— we've already talked about this, you know, reciprocity is kind of the foundation of having relationships that scale over time.

And you don't want to live in a place where you have to negotiate every single thing about your day. I don't want to have to map out— Speaker A: that is the lack of ability to move safely, freely through the scaffolding. Right. Speaker B: I don't want to have to negotiate every part of my existence. I don't want to think a ton about how I get to work. I don't want to think a ton about if I can interact interact with, um, you know, like there's— when you, when you don't have social trust, there are entire parts of your environment that just become off-limits to you.

And, and it really, it's really unfortunate for the people in your population that are already pretty vulnerable. So for example, kids, right? We talk a lot about why kids can't move freely anymore, right? The loss of mobility that a lot of children in a lot of countries have enjoyed. Speaker B: I don't want to have to negotiate every part of my existence. I don't want to think a ton about how I get to work. I don't want to think a ton about if I can interact interact with, um, you know, like there's— when you, when you don't have social trust, there are entire parts of your environment that just become off-limits to you.

And, and it really, it's really unfortunate for the people in your population that are already pretty vulnerable. So for example, kids, right? We talk a lot about why kids can't move freely anymore, right? The loss of mobility that a lot of children in a lot of countries have enjoyed. Speaker A: But there are still countries in which children can see the kids wandering around Japan. Speaker B: It's crazy. Exactly. You know, there's that whole show Old Enough, And the whole point of the show is that a 2-year-old can operate functionally in your, in your city without having to kind of— and like that a parent would let a— the youngest kid, I think, on that show was 2 years old.

I mean, he's probably almost 3, but a 2-year-old running an errand, right? And the, the thing that you worry about the most is, is he going to remember the grocery list? That's like unheard of here, right? And that first— Speaker A: it's like the first episode of First Lady. Not that I sent my 2-year-old, but like, will he remember the grocery list? There's one specific part, maybe, to— we had so many ways we could take this. But one, one thing I like a lot about how you think about it is, is sort of COVID being this really good— or not good— COVID being this forcing function for some of these things, like this notion that as we reassimilate into the world from this very online COVID life, we're rediscovering some of these social dynamics from first principles or having to sort of face the Chesterton fencing of them.

Classic example, like, why does etiquette actually matter? Why do you— one example that sticks in my head that you brought up is like, why do you not, if no one opens your wine bottle at the dinner party, not take it home with you? These types of little things. Can you elaborate on that? Speaker B: Well, I don't know if there's much to elaborate on, but, you know, or even just give— Speaker A: like you brought up the speakers Another one, like greeting someone in retail, like, yeah, just talk about why some of those things are load-bearing.

Speaker B: It's again, it's these like shared scripts that, that make it easy for a stranger to interact with you because without that you don't have anything else, right? There is, I think, often an overemphasis on like the things that you can see that are obvious about any social situation or about like governing right? And the things that we miss— like, you can basically only operate to the level of effectiveness as, like, the least effective part of your society, right? Speaker A: It's like a minimum viable threshold or something. Speaker B: Exactly, right?

And so if you are able to say— they're like— we were just in Montecito with, uh, a mentor and friend of ours, and we decided as our gift that we were going to get him, uh, books, and we were said, you know, sign, sign, tell him why we got him the book. Okay. So I, I guess I had probably shipped the book that I wanted to get him too late. So instead we went to a couple of bookstores in town. And now, of course, Montecito is not your median town in America in any meaningful sense.

It is a total enclave. Speaker A: Idyllic. Yeah. Speaker B: But, but there are places that, you know, aren't nearly as wealthy, let's say, that still enjoy this level of social trust. Like the churches, the church that I went to growing up, it's near, you know, you wouldn't call it projects, but it's near just like lots of apartments and lots of, you know, there's, it's like not in the best part of Dallas. But often the doors to the church are open. Like they're unlocked. Speaker A: Idyllic. Yeah. Speaker B: But, but there are places that, you know, aren't nearly as wealthy, let's say, that still enjoy this level of social trust.

Like the churches, the church that I went to growing up, it's near, you know, you wouldn't call it projects, but it's near just like lots of apartments and lots of, you know, there's, it's like not in the best part of Dallas. But often the doors to the church are open. Like they're unlocked. Speaker A: Yes, yes. This is captured. Yeah, yeah. Speaker B: Right? And so anyway, back to Montecito. So I went to this bookstore. I didn't bring my wallet with me. I don't know why I didn't bring my wallet with me, but I forgot to.

Speaker A: You're in Montecito. These things are taken care of. Speaker B: Well, you just You can use Apple Pay, you know, you think you could use Apple Pay anywhere. Speaker A: Sure. Speaker B: Um, but in this particular store, I couldn't use Apple Pay. So I pick out my books and like, there's a couple books that I just, I really want to get these. And I'm thinking, all right, you know, they don't take Apple Pay. They, they don't have, um, tap to pay. So it's just, it's over for me.

And the store owner said, no, no, no, that's fine. Take the books. And then when you get back to New York, just write me a check. Just send me a check. And I was like, what? You know? And he's like, "Yeah, just send me a check. It's fine." And he really wasn't trying to argue with me. He said it as though it were the most natural thing in the world. Speaker A: There's an abundance inside of that rather than scarcity. Speaker B: Yeah. Yeah. Because in his world, right, in the sort of— his sort of daily context, basically everybody can be trusted.

You know, if you're in Switzerland, their public transit system handles, I think, I might be misremembering, but at least like a million rides a day. But they don't have fare gates anywhere. You just step right onto the train. Think about how many times you've been late to something because you're like behind the queue of people trying to, you know, pay. Speaker A: Some person who's new, it's a tourist who doesn't know how to eat, right? Speaker B: But in Switzerland, you just walk straight on because the assumption is that the population is going to, is going to pay, right?

And so instead what happens is you get these random ticket checks. And if you're found— Speaker A: oh, you just pay on your phone? Like, there's no— Speaker B: yeah, you pay. Yeah, exactly. You just walk straight on. Wow. Yeah, right, right. Um, and, and so if you're found to have not paid, to be fare evading, you get a fine of about 100 Swiss francs, right? Um, and there's a lot baked into that assumption, or baked into that scheme, right? The assumption that most people will pay. It actually is interesting they've seen fare evasion rates increase about 50% in the last couple of years since like 2018.

And what they think is happening is, of course, one of the countries that borders Switzerland is Germany, another is France. And they think on the French side of the border, you're getting a lot more people coming from France where there's just a less strong norm about paying. And they think that's what's happening. And so there's, there's some debate about what you do about this, right? Speaker A: Implied in all of this is, is norms. And a sort of, um, staying above the tragedy of the commons in some sense. You brought up agency earlier, pointing at this.

This is an aggressive framing of it, but I think it captures how you feel. What is cultural arson? Speaker B: Um, I think I call many more things cultural arson than my friends would. Okay, let's just take an example. A couple of months ago, there was a sort of scissor statement that happened again in— Speaker B: Um, I think I call many more things cultural arson than my friends would. Okay, let's just take an example. A couple of months ago, there was a sort of scissor statement that happened again in— Speaker A: I think a statement is a reference to a Scott Alexander blog post that everyone should read, but the essence of it is sort of like, it's like the dress, it's the blue and white or the black and gold, or I mixed that up, uh, it's, it's the dress where like it's obvious to everyone that it's one, it's yes or no, and no one can understand how anyone could believe is the opposite.

Speaker B: Exactly right. Speaker A: Thank you for Mansplain a little bit. This is a podcast. Speaker B: And I guess this originated like so many annoying things do in tech Twitter, or maybe it was rationalist Twitter. There's some overlap. And so a guy is recounting a story of being out with his girlfriend on a very cold day. And so he, he tells his girlfriend like, I'm cold. And she does what he thinks is like the highest agency, agency thing. Speaker A: You can just do things. Speaker B: Exactly. You can just do things.

So what does she do? She, like anybody would, goes to the first hotel that they pass, and she tells them that she's just stayed at the hotel and she has forgotten her scarf. So they— this is some European country— so they end up pulling out the scarves, and she takes the nicest one, and she gives it to her boyfriend, and he's no longer cold. Now, he tweets this, and I think— and I think this is an innocent story. I don't think that this guy is a bad guy or anything like that.

But I think he probably expected the overall reaction to be positive, right? Like, your girlfriend is so high agency. I wish I had a girlfriend like that. Speaker A: Like anyone would do, right? Speaker B: Right. And it's like, no, I actually wouldn't do something like that. The only reason why your girlfriend was able to pick out a scarf is because most people who need a scarf because they're cold don't act like that. And there is just, I think, a, a real lack of appreciation for— Speaker A: And by the way, the person who lost the scarf actually now won't get it.

Like, a very simple— Speaker B: like, you don't know how long it's been there. You don't know. Maybe it's been there for months, in which case, okay, fine. But you don't know that when you're choosing to sort of tell a lie about needing a scarf. And, you know, it's, it's fine. It's fine if one person did that. But if everybody did that, if everybody said, you know, there's like a very tortured logic that a lot of young people employ towards shoplifting these days, right? And the idea is like, yeah, I wouldn't shoplift from a mom-and-pop shop, but Amazon— but, but, well, I guess you can't shoplift, whatever.

Speaker A: Well, Walmart or Walmart, Target. Yeah. Speaker B: And, you know, today, and it's not necessarily because of young people, it takes me forever to just get some freaking toothpaste, right? Like, nobody thinks when they decide to fare evade or decide to take a scarf that doesn't really belong to them or decide to steal something, that that could cause a ripple effect. Speaker A: Yeah, it's like a paper cut. Speaker B: That's right. It's like death by a thousand cuts. Because again, no one person acting this way is going to ruin the experience.

But again, if everybody acted that way— and I think this is sort of the genius of broken windows theory, which I think has been sort of empirically kind of borne out. Speaker A: Yeah, it's like a paper cut. Speaker B: That's right. It's like death by a thousand cuts. Because again, no one person acting this way is going to ruin the experience. But again, if everybody acted that way— and I think this is sort of the genius of broken windows theory, which I think has been sort of empirically kind of borne out.

Speaker A: I don't know this. Speaker B: The idea behind broken windows is if you were in a neighborhood and a window breaks, for whatever reason this window breaks, and you don't fix it, you can expect that in, in enough time, in due time, every window in the neighborhood is going to be broken. Wow. And he also has this phrase called defining deviancy downwards, where you sort of slowly lower the standards of behavior. And so the lowest common denominator slowly gets worse over time. And you see this borne out in so many places, right?

You see the— if you're at a concert and one person thinks it's okay to throw something at the performer, right? Like, you're starting to see this way more often. People are, like, throwing— not just, like, you know, throwing a bra or whatever, but, like, throwing things that are hitting performers, throwing people's cell phones at performers, and it's hitting people in the face, right? You just end up— if you let even a little bit of these things slide, you just end up eventually with an environment that's just worse. So it is just— it raises the opportunity cost of being in public, right?

Speaker A: How would you describe to people— you, I, for the most part, most American listeners are probably taking the way we, for the most part, are able to move socially through our scaffolding freely. Like, how would you challenge people or how would you kind of like illustrate, maybe to lead you a little bit, like you, you've talked, you brought it up briefly, South Africa, like you once told me, like South Africa looks a lot like A. and yet— Speaker A: How would you describe to people— you, I, for the most part, most American listeners are probably taking the way we, for the most part, are able to move socially through our scaffolding freely.

Like, how would you challenge people or how would you kind of like illustrate, maybe to lead you a little bit, like you, you've talked, you brought it up briefly, South Africa, like you once told me, like South Africa looks a lot like A. and yet— Speaker B: Well, in certain places anyway, right? So the first time I visited South Africa, I was in Johannesburg and specifically Sandton, which is like one of the wealthiest parts, if not the wealthiest part of Johannesburg. And it's the business district as well. So from your hotel, you're looking out and you see like Deloitte over there and you see the Radisson Blu over there and, you know, the Hilton South Africa over there.

And the first time I went, I think I tweeted a picture of Sandton and I said, where do you think I am? And the responses I got were like, oh, you're in A. or, oh, you're in Tyson's Corner, Virginia, which was not a horrible guess if you've ever been to Tyson's Corner, Virginia. And if anyone was paying attention to the lights, they would have seen, okay, I'm, I'm not in America. But the first thing I was told by the people that we were with, the very first thing, and it's like broad daylight, is never have your phone out in broad daylight.

And actually just last week in London, I was going for a walk with, um, with Sam, my manager, Sam Bowman, and he said the same thing to me. We're talking about London, not South Africa, because he knows people who've had their phone stolen from them. Like one of the ways that people will do this is by just being on some sort of like a motorbike. Speaker A: I watched a guy do this and I was in London. I watched the guy just rip it out of somebody's hand. Speaker B: That's insane, right?

Speaker A: Yeah. Speaker B: And so, so, okay, what are we talking about? For people who can't imagine this, it's like every decision that you make becomes more frictionful. So you can never just turn your brain off and exist, right? My sister, she did a study abroad for some— for a couple of— for like a summer in Spain. She was both in Sevilla and then also in Barcelona. And she would call me from like 3— at 3 m. her time, just walking alone through the streets to get back home. Because, you know, Spanish people, they're up all night.

And I would be like, what the hell are you doing? Right? Because there's no chance that I'm going to be walking around, you know, at 3, generally speaking. Right? And— but she is in an environment that has all of this, you know, social infrastructure that supports the ability of a single young woman to walk around and not have to be particularly vigilant. Now, this, of course, you know, there is some level of vigilance, but, you know, the idea that you could just be on your phone really not paying attention because you know the way home and whatever and, like, get home safely— this is what I want for everybody.

And I think until you are in an environment where you do have to think about every single piece of your environment, it doesn't really click. And it's unfortunate because I think maybe in the West and, um, you know, specifically in America, because it's the context we know, people won't really appreciate it until We get there, they go to CVS, and all of a sudden every single thing I need is locked up. And so going to— Speaker A: or better yet, like, the Walgreens has the, like, the glass broken in. Speaker B: Yeah, exactly.

Speaker A: For parts of San Francisco for a little while. Speaker B: Yeah, you know, San Francisco I think is, is getting better, but, you know, they finally got a Whole Foods, and the Whole Foods in San Francisco shut down like a year later because they couldn't stop people from, um, kind of loitering and using it as like a public bathroom. And also there was just way too much theft. And a lot of times people will laugh at this, right? Right? They won't care. But this is getting back to the question.

This is what I mean by cultural arson. I have way more anger reserved for the— for the people who would excuse this kind of behavior than I do for sometimes for the, like, antisocial person who just, like, lacks impulse control for whatever reason, right? Speaker A: Like, or just, like, had an emergency, or whatever. Like, every— every incremental action of this type can be justified. Sorry. Speaker B: Yeah, exactly. You can go to the end of the earth. And so you'll, you know, you'll hear people who say it's actually— it's just— they're— it's like the tyranny of root causes.

Well, poverty is the reason why I need to steal, you know, dozens of whatevers from CVS. And it's like, again, you can make any excuse in the world. People say this about fare evasion, but in fact, most cities— in most cities, the people who are evading fares are not the poorest people. And most cities have programs that allow people who— like, low-income people— Speaker A: Right, right. Speaker B: —to kind of ride for free or very reduced rates. Yeah. And so again, it's this— sometimes what you have just in society— we live in a society— is I think an overemphasis on the extremely visible parts of disorder, and maybe a lack of appreciation for, like, the kind of little cultural cracks Yes.

That eventually, you know, end up concluding in— again, I know the CVS example is, like, insane, but 5 years ago you could go to CVS anywhere and get anything that you needed. Yeah, yeah, yeah. Right? Speaker A: Right, right. Speaker B: —to kind of ride for free or very reduced rates. Yeah. And so again, it's this— sometimes what you have just in society— we live in a society— is I think an overemphasis on the extremely visible parts of disorder, and maybe a lack of appreciation for, like, the kind of little cultural cracks Yes.

That eventually, you know, end up concluding in— again, I know the CVS example is, like, insane, but 5 years ago you could go to CVS anywhere and get anything that you needed. Yeah, yeah, yeah. Right? Speaker A: Well, what's inside of all of this? And you've described, like, a case against Mercy, which sounds very extreme. Speaker B: Okay, that's the name of a piece that I'm currently writing for Works in Progress. Wow. So we can't linger here for too much longer because you have to read the piece. Speaker A: What I think I'm hearing though, and I want to make sure I have the right frame around, is that it's almost a, um, we've talked about examples here that are sort of like soft scaffolding and hard scaffolding.

And soft scaffolding is more of these social things and like taking a scarf or norms. And then hard scaffolding is like, actually, can I walk around this city safely without being mugged? What I think you're just You're pointing at, though, is this notion that actually, like, it's a continuous gradient and the soft things actually eventually give way, break the dam by a thousand cuts to the hard things being possible. Speaker B: Exactly. Like, again, the thing that I tend to focus on is the substrate, right? The stuff that isn't obvious, because again, that's the stuff that is load-bearing that you don't expect is.

Yes. And then we're talking about, you know, I think very much a live conversation in tech right now is about norms. You know, there are things relating to acquihires, acquisitions. You know, what do employees owe their employers? There are entire companies that I think, as they currently exist, are contributing to an environment that is— that makes, you know, tech more low trust, that makes people more suspicious of each other. You know, there's lots of technology that And again, even if that's not what the technology actually does, what does it mean when you brand something as cheating technology, right?

There's this argument that in fact there's already rot. And so all I'm doing is exposing the rot. Speaker B: Exactly. Like, again, the thing that I tend to focus on is the substrate, right? The stuff that isn't obvious, because again, that's the stuff that is load-bearing that you don't expect is. Yes. And then we're talking about, you know, I think very much a live conversation in tech right now is about norms. You know, there are things relating to acquihires, acquisitions. You know, what do employees owe their employers? There are entire companies that I think, as they currently exist, are contributing to an environment that is— that makes, you know, tech more low trust, that makes people more suspicious of each other.

You know, there's lots of technology that And again, even if that's not what the technology actually does, what does it mean when you brand something as cheating technology, right? There's this argument that in fact there's already rot. And so all I'm doing is exposing the rot. Speaker A: Or better yet, that is a— that's a high agency. Speaker B: You can just do things. It's high agency, right? But actually making things worse doesn't make them better. It just makes things worse. The way to make things better is to just make them better.

And that sounds like a tautology or whatever, but it's like, this is basic stuff, right? And so I find it kind of both heartening and disheartening to see, you know, a lot of people that I really appreciate saying, "Yeah, I really don't like that. I don't want us to become the kind of place that sort of rewards what I think is, again, cultural arson." We have lost the ability to distinguish between— and And like, some people use their agency in ways that I think are just bad, right? Or that probably even though, you know, there are a lot of cultural consensuses that no longer hold, cheating is bad is, is one of the ones that I think still holds, right?

Speaker A: But will it in 10 years or 5 years? Right. Right. Speaker B: And, and it certainly won't if we all kind of like reward that understanding. Speaker A: Or not even reward it. I, I think rewarding it is another step. It's almost just like, ah. Speaker B: It's fine. Yeah. Yeah. You know, I— what you've seen is a lot of people who even we admire, who you can see are doing bits. Yes. Like, you interact with them in real life. Yes. And they are not saying the insane stuff that they say online.

And it's so clear that they've been either audience captured or like something has broken in their model of the world, in their brain, whatever. Speaker A: I think it's actually just like, it doesn't matter. Speaker B: Yeah, there's like this, like, fundamental nihilism, right? Like, I'm just saying things. I'm in the arena saying things. Speaker A: I love your commentary on agency, though, which is that, like, it is so captured by the "you can just do things" thing, which is— there's two ways to internalize that. There is actually the world is plastic and you can experience the world as happening to you, or you can experience the world as asserting yourself on the world.

That is so powerful. Arguably, there's nothing more important to teach. Like, that is so important. And yet there's also a a version of this you can just do things agency thing that I think you're pointing out, which is like you can just take what you want, which is not the same thing and not necessarily just good. Speaker B: It's certainly not the way I would advise, you know, young people— and we're still young— but young people to go about sort of entering this industry. Right. And I think tech in particular, you know, whatever a lot of people want to say about it, however people want to criticize it, it.

One of the things that I do think is quite unique to this culture is that in a lot of places there is just positive sum. Speaker B: It's certainly not the way I would advise, you know, young people— and we're still young— but young people to go about sort of entering this industry. Right. And I think tech in particular, you know, whatever a lot of people want to say about it, however people want to criticize it, it. One of the things that I do think is quite unique to this culture is that in a lot of places there is just positive sum.

Speaker A: Yes, this goes back to scarcity and abundance. One of those things, one of those definitions of agency is abundant and the other is scarce. And that is so important. I think. Yeah. Speaker B: No, no, no. It's, it's just in a lot of different places there's just like positive sums are baked in, right? One of the biggest places that exists is in employee equity, right? You're getting literally a share in this company, but also it's, it's just common that people just are constantly doing favors for each other. And, you know, you're not constantly waiting by the phone to see when that person is going to do a favor back for you.

These dynamics can exist for a long time. And so you have, you end up having this dynamic that's rather like Scorsese and De Niro, where you have like investors and founders that just tend to work with each other again and again and again. Um, and, and of course you like build networks and whatever. Um, And, like, that's a really great thing. That's really valuable. And to your point, my favorite way of looking at agency is anything that forces people to not think of themselves as entities to which things happen, but instead, you know, as this, like, internal— really kind of developing an internal locus of control, developing some appreciation for cause and effect.

And not to belabor the point, but I do think there is maybe, at least maybe I grew up with one, or maybe as I was growing up, I was too impressionable or something. There is, I think, a cultural script that really wants young people. And I think some young people in particular, I'm a Black woman, I can be no other. I've been a Black woman for 20-whatever, 29 years. And, you know, some of the advice that I got, even sometimes from the people closest to me, was that everything is just going to be so much harder for you.

Everything is going to be harder. You know, there's the classic you have to work twice as much to get— twice as hard to get half as much. And I'm not saying that those dynamics don't exist, and I've seen it in my own life. But the kind of practical effect of internalizing messages like that is that you shouldn't even maybe try. You should probably not even bother because it's just going to be harder for you. It's going to go worse for you. But you should be an actor. You should be an active participant in your own life.

That doesn't mean, you know, think of yourself as a main character, but maybe, yeah, think of yourself as a main character. You know, there are all sorts of ways in which the world is malleable, all sorts of ways in which there are these, like, invisible rules that exist on paper but don't really exist. You can, you can cold email anyone. You know, a couple of weeks ago, a couple of months ago, Dora Cash interviewed Satya at Microsoft. And the way that he did that, you know, I'm thinking, you know, he had a strategy.

He literally just emailed him. It was like, hey. And, you know, he had done some work beforehand to say, these are the kinds of questions that I would ask you. But so many people— I'm not saying, you know, I could get Sacha tomorrow, but maybe I could, you know, maybe I could. And I think it's so healthy, especially from a young age. Someone that we both love is Simon Sarris. He's written about this a lot, about about kind of developing agency, especially in your children and instilling it in your children.

And I agree with him on this. There is this, I think, innate desire in humans to want to be useful. And you see this in very young children. And so I've stayed with him and Sammy for a weekend at the time. Uh, they just had Luca. They now have 3 kids. And even then, Luca is like 2 or 3 at the time, and he's like doing chores. And he sort of has internalized this idea that like if he wants something, he can go make it. He can go get it. He can get an egg from the chickens or whatever, you know, he can, he can act.

He's not at the mercy of mom and dad because they want him to develop this really confident sense of self and this ability to be totally sufficient. Not that he needs to because he has an incredibly loving family and this whole tapestry of care, but so that he can be in the world. Absolutely. Out of abundance, which is one of those words right now. Speaker A: It is. Yeah, that's true. That is a great lead-in to the next thing I want to talk about, which is your unique path. I asked a friend of yours what I should talk to you about, and one of her— one of the things she brought up was that you have a very N of 1 path.

You do things in a very distinctly Tammy way, which I think applies to so much of the agency stuff we were talking about. One bit of this that I like actually comes from your friend Nick Whitaker. In your advice to young people, little excerpt, you, you have some threads from other friends. He says, "Interesting paths are not repeatable, but they rhyme." Who are you aspiring to rhyme with? Speaker B: Oh, that's interesting. That's not the question I thought you were going to ask. Who am I aspiring to rhyme with? Okay, it's some combination of Anna Wintour and also maybe Pamela Harriman and also maybe Esther Cooper Smith.

Okay. Speaker A: I don't know the last two. Okay. Speaker B: So who are Pamela Harriman and who are Esther— who was Esther Cooper Smith? Speaker A: Who's Anna Wintour while we're at it? Speaker B: You know, outgoing, no longer, soon to be no longer EIC of Vogue and a total force of nature. Because one of the things that's really interesting about Anna is that she basically was like the image maker for so many people. So if you're like a female politician and you're struggling with likability, you go to Anna.

If you're an athlete who is leaving, you know, playing sports to pivot into doing a beauty brand, you go to Anna. If you're, you know, a new celebrity who is hoping— it's the middle of awards season and you're hoping to get your name and your face really in front of the most important people, you want to be in Vogue, right? And there's this, like, cultural capital that I think Vogue has, and people want to say that it's declining. And I do think it's declining, right? I do think the Vogue formula currently is not as interesting as it used to be, but there are still signs that it's ahead of the zeitgeist.

One example I'll give you: Vogue's first 2020 issue, they called the Motherhood Issue. And they had 4 different covers, one with Cardi B, one with Ashley Graham, one with Stella McCartney, and one with— I, I can't remember if it was— maybe it was Greta Gerwig. I can't remember. And the whole idea is that, you know, for so long you wanted women to kind of compartmentalize the things that they do. You know, you are a mom here and here you are Superwoman. But in fact, for many women, being mothers has unlocked, you know, if they're creative— Stella McCartney says this— has unlocked a lot of her own creativity, has made her think, you know, in really careful ways about the clothes that she's making or whatever.

Cardi B says she always wanted to be a young mom, you know, she didn't want to, you know, a lot of people said when you have— when she had a baby that she would be ruining her career. Well, here we are. Her daughter just turned 7. Cardi B hasn't gone anywhere, although We are waiting for the sophomore album. And of course, like, where are we today? Oh, now we're all talking about fertility and now we're all talking about, you know, what are the kind of cultural reasons why people are having fewer kids?

I will say some of us have been thinking about this for a decade. The Twitter history is there. But anyway, fine. Okay. Speaker A: Twitter history is always there. Speaker B: You know, but, but moving on, moving on. Anna, basically what she— she was the curator. She was the cultural curator. And like, nowhere is that more clear than at the Met Gala. And again, there's a ton of people who will say, I don't care about that. I've never heard about that. And, you know, to that I say, you know, there's a lot of people who don't watch the Super Bowl.

And those of us with taste, we like both. But the other two are actually— Speaker A: Like that taste isn't real. Speaker B: But the other thing that is— Esther Cooper Smith is really interesting. And she is an archetype of woman that I think— I hate this term and I need to just, like, level up my vocabulary. I think that she's underrated because she was— so she was a socialite. She was a socialite in C. She was a huge donor, mostly to Democratic causes. But the real value of her was as a hostess.

So on any given day, just like with Anna, you know, everything we just said about when you go to Anna, Esther is who you went to sometimes to, like, loosen, loosen the— or, or remove the friction in some literal geopolitical conflict. She was the kind of— I joke that she's maybe the only person who could have gotten Joe Biden to drop out of the race earlier than he did. Wow. Because she was such a trusted— she was just a great host. And the art of hosting is something that I think is lost on a lot of people, right?

It's one part curation, right? But it's one part knowing how to invite people to a space and invite people to open up in ways that they wouldn't necessarily, maybe even one-on-one. Right? And maybe beyond that, just, yeah, the sort of power of that kind of social grace, social intelligence, right? And, you know, it's interesting to me that I'm seizing on both fashion, Vogue, and also on hosting, because for a long time, these are these, like, uniquely female sources of power, right? Or ways to kind of accrue influence that don't require you to, like, you know, have beat sexism.

Speaker A: So, or have like, um, totally embodied this much more masculine— like, there's plenty of— most of the best historical examples of women really succeeding in like other areas of business are because they like down-leveled their femininity, at least in some ways. Speaker B: Yeah, yeah. And, and I think these are areas in which, yeah, your femininity is a total asset. Not to kind of reduce it down to hosting, But I think a lot of people devalue things like this. Another example— Well, part— Speaker A: not to sidetrack the beginning of the conversation— is partly because they're more illegible.

Exactly. Speaker B: You know, I'm not a royal family watcher, but something that people often say about Queen Camilla is that she is the person that you want to sit next to at any dinner party. She is so interesting. She has that form of charisma we were talking about where sitting next to her means that you are the only person in the world for the entirety of that dinner. And again, there's these just like forms of social leverage that are really enchanting to me because they don't require you to brute force anything.

So if I want my path to rhyme with anything, I think it's far more of that than, you know, of anything else. Speaker A: I've thought about the third person you said, uh, Pamela Harriman, and she's interesting, right? Speaker B: There used to be this kind of person who was was just like a transatlantic person, right, who had— who, you know, had what we— who had cultivated a social scene both here and in the UK. And of course, this is like very class-based. There are some really dramatic examples of this with the dollar princesses, right, the American women with fortunes who married into UK titles because, you know, they each have what the other wants.

And of course, you have like maybe the most famous example with Consuelo Vanderbilt. But there are all sorts of people who used to just exist on both sides of the Atlantic. And again, who, who were, like, really fierce individuals who had quite a lot of— in this, in Pamela's case, not just, like, social influence but political influence, right? She was a close confidante of Winston Churchill. And that's just, you know, not that I want to be a close confidante of, you know, any specific president, but yeah, again, there are quiet ways to be able to influence things may be more enchanting than just having to kind of take tons of power.

Mm. Speaker B: There used to be this kind of person who was was just like a transatlantic person, right, who had— who, you know, had what we— who had cultivated a social scene both here and in the UK. And of course, this is like very class-based. There are some really dramatic examples of this with the dollar princesses, right, the American women with fortunes who married into UK titles because, you know, they each have what the other wants. And of course, you have like maybe the most famous example with Consuelo Vanderbilt.

But there are all sorts of people who used to just exist on both sides of the Atlantic. And again, who, who were, like, really fierce individuals who had quite a lot of— in this, in Pamela's case, not just, like, social influence but political influence, right? She was a close confidante of Winston Churchill. And that's just, you know, not that I want to be a close confidante of, you know, any specific president, but yeah, again, there are quiet ways to be able to influence things may be more enchanting than just having to kind of take tons of power.

Mm. Speaker A: Also, in that advice essay, you say avoid chasing the red herrings of success. That was about a year ago. I'm curious how you reflect on that a year later, maybe especially because you are someone who ultimately professionally is because you work in media and to some degree, like, the land of ideas and narratives. And so it seems— it's just been something I've been reflecting on a lot, maybe as I make more media too. But like, to what extent— there could be a notion that like media and ideas and narratives, are those red herrings?

Are they actually a thing? Like, and maybe more broadly, just how you think about that idea of like inputs and outputs or whatever, or red herrings. Speaker B: How do you know that the stuff that you do matters? That's where a lot of my— Speaker A: of course you're never going to know. But there's a meta thing which is like, how do you— Speaker B: what are the metrics by which you judge yourself? So for me, for example, I care a ton about book sales, but I care way more that if we are publishing books like Scaling People, High Growth Handbook,

, that I'm hearing from founders, executives, engineers. We know we have one of our bestselling books is An Elegant Puzzle, which is all about engineering management, which which seems like such a niche, you know, field, but that is one of our best-selling books. I care way more about whether or not the people who are working in these particular industries, disciplines, whatever, find it useful, right? Because the whole point of Turpentine is that it's actually supposed to be useful and fundamental in some important way. You know, nobody is born knowing how to be an engineering manager.

And so sometimes, and it's always the best when I hear from people directly, You know, we do these pop-ups now where we'll just show up in a city and have a one-day coffee shop. And inevitably I just get— I'm just— I get stuck in dozens of conversations about, at this point, about how a particular book helped them set up their company or help them run. You know, Claire, a lot of her time right now is spent speaking to companies that are huge already, right? Because you know, her particular philosophy when it comes to running an organization is actually kind of novel, right?

It's not like this one weird trick for management or like inundating you with a million examples that are just impossible to generalize, but instead this kind of principles-based framework for all sorts of things like hiring and whatnot. And that is to me the metric when it comes to the turpentine. On the other side, right, it's hard to know if you're kind of moving the culture in a particular direction. But like, that is hopefully the metric, right? Another one is— I say this in the piece, the advice to young people— you unwittingly end up creating an announcement economy.

So you're constantly announcing the intention to do things, and you can get just as much praise, it turns out, and money, and, you know, all sorts of good things things by announcing an intention to build something as you can by actually building it. So we're in this time of incredibly glossy pre-launch videos. And then, you know, I was talking to, um, Lulu Masurbi the other day, and she actually kind of took the other side of this argument, which is that part of what you're trying to do when you launch a really glossy video, right, you do it first even if the product hasn't quite caught up to the capabilities, is you kind of want to like demoralize the competition.

You want to make it harder for people to think it's worth working on whatever the competitor, right? Speaker A: And you're also trying to sort of like aim for the moon and hit the stars or whatever, right? Speaker B: But I tend to think that, no, you— it actually just amounts to overpromising. And maybe sometimes you never actually get there. Speaker A: There's another part of your path that you have described as a sort of everything, or maybe it applies beyond just your path, but you've used framings like, I'll end up there, or the right people will get there, I think another thread of this that I feel is important is this notion that sort of actually friction in certain contexts is good.

Can you talk about what that all means? Yeah. Speaker B: Um, there are— now, I don't— I certainly don't mean to imply that friction everywhere is good. Yeah. Um, there is plenty of friction that keeps out, you know, part of the reasons right press exists is because it's way too difficult if you're— even if you're in San Francisco to get a meeting with the likes of Allade, Claire, Will Larson, and so on. It's that much more difficult if you're anywhere else in the world, right? So like I have an appreciation for friction, but in some places, right, uh, having some friction actually ends up meaning that whoever ends up in that thing is high signal.

Like there's a lot that we can take from the fact that, okay, let's just take YC, right? There's a lot that we can take from the fact that Paystack and Stripe ended up in YC coming from very different places, right? You actually do want some friction. And or to take a different example, a friend of mine, Maren, she founded a technology fellowship called Interact, and it's a fellowship for young people and not just aspiring technologists, because increasingly we have a lot of people who are interested in like who take a much more academic lens to technology.

So increasingly it's, it's a really interesting multidisciplinary community. But either way, it's a fellowship for people who are 18 to 24. And one of the most important features about Interact is that Maren does not advertise it anywhere. And it's a very— Speaker A: I don't— I've never been a part of it, but I met a lot of people in it. And there's something— there's something about you guys that isn't super legible and also probably wouldn't be the case if it were like as well-known as YC. That's right. Speaker B: And it's so interesting because if I hear that the person who's in front of me is an Interactor, it just tells me off the bat a bunch of things about them, right?

And so in Interact, what's I think particularly interesting is that it's an extremely global community and it's also about 50/50 men to women, but there is no concerted effort to make it either of those things, right? Like at some point, We let in the first international student and/or young person or whatever. And then, you know, it kind of just goes from there. And it's not so much— it's not like when I was 18 to 24, it's not like I would have recommended every single friend of mine do Interact. But again, there is some sort of useful friction.

And so, you know, I'm not sure that you would get a better crop of Interactors if instead of being really primarily word-of-mouth based, you were to plaster signs about Interact in every blue box. Speaker A: Do like performance marketing to make sure you're like the most targeted, whatever. Yeah, exactly. Speaker B: And, and for some period of time, I think Stripe Press was like that as well. You know, there have been requests for us to do media about it, you know, to talk— why are you doing this? That's the question everyone always asks.

Why does a technology company have a press? But maybe you don't need to explain it. And also at least with my path to Stripe Press, right? There was no— there was no particular reason I should have stumbled into it being, again, somebody who's focused on charter cities in DC. But it just so happened that a year before that, a year before discovering Stubborn Attachments, I'd worked at Mercatus with Tyler Cowen. And so it is interesting to me that oftentimes communities end up forming in the right way and you don't need to necessarily— Yes.

Like go super emergent or the dots connect or universal. Yeah, the dots connect, right? I guess the only last thing I'll say about that is that, you know, you can kind of brute force your way into assortativeness, right? One way to do this is by turning yourself into a door-to-door salesman. And that's what we mean when we say you can actually send 1,000 cold emails. Yes. But I think a far more interesting place to find yourself can be found if you decide you want to instead be a billboard. You kind of want to put out, whether it's by tweeting or by your blog, right?

Writing online is still incredibly underrated. You just put out these signals to the world. Yeah, yeah, yeah. Like, these are the things I'm interested in. These are the questions I'm asking myself. Yeah. And, you know, if you want to inquire together, make it really easy for people to reach out to you. Speaker A: It's like working smarter rather than harder on the— on the— sending 1,000 cold emails is very respectable, but there is a version of it that is a little more like more specific or more nuanced. Speaker B: It's also driven by the things you actually care about, right?

So you might find that after sending, you know, your 567th email that you find yourself in front of, you know, Fortune 500 CEO number 6 or whatever. But that doesn't mean they have anything in particular to teach you, and it doesn't mean they have any— to you, yes. That's right, you know. Yes. And it doesn't mean they're not brilliant and whatever, but that's often far less useful than, again, you know, doing some work to figure out what is it that I'm interested in. And following your own curiosity is, I think, pretty underrated.

Speaker A: We've talked about dignity and self-respect and doing a great job in regardless of how crummy the job you're in or whatever it might be. I think another way to frame all of that would just be standards. There's an amazing quote, I think from an interview that you gave where you're talking about the time you got to spend with Charlie Munger. You say, or this idea that how you do business and the standards that you hold yourself to are so much more important than what's easily measured which is what I got from sitting around and talking to Charlie Munger.

He wasn't super happy to sit around and talk about money, but he did have very strong opinions about how to conduct yourself in business. What standards do you hold for yourself professionally? Speaker B: I think that ultimately what you want to create is what Charlie described so perfectly that we've already talked about this. Seamless web of deserved trust. You want to act in ways that set yourself up to work around people that you really like and learn a lot from, to have them trust you and rely on you for sort of increasing amounts of work.

And so how do you kind of set yourself up for that? Well, one of the big things is— I think there's probably a couple. Number one would be never compromising the quality of the book. That has to be paramount. So, um, for example, if I get to the second half of the year and I haven't commissioned a ton, it's not then the time to just go pick something out that we already said we're not going to publish. Speaker A: But in jobs like this, investing is kind of similar actually. It's hard to not just feel like, oh, I got to be busy.

Yeah, yeah. Speaker B: You know, you get desperate. Yeah. Or something else that happens, and I'm sure you've had this where people have like pitched themselves for your podcast or pitched somebody in particular. We've gotten inbound from really big names, which if we had chosen to publish them, would have led to instant bestsellers, right? Books that like big names that, you know, or people coming from companies that you absolutely know that are like like very important, right? It's worth it to us not to compromise again the quality of the book, which means something that either adds to this bank of turpentine or is a provocation that we think is important enough that the kinds of people that we are talking to should internalize.

Speaker A: That's the bar. Yeah, the stakes are high. Speaker B: Yeah, the stakes are pretty high because again, we don't do 50 books a year. We're not looking for a hit out of 50. We do a couple of books a year and we think that every single book is additive or is in some way Yeah, building on the past catalog or sort of taking us into a new direction we're excited about. So it's never compromising the quality of the book. I think number 2 is being delightful to work with.

Yeah, being easy to work with. You know, I think there was probably a time where I was like a bit of an enfant terrible. That's definitely not the way that you pronounce that, but whatever. I've only ever read that term. Um, yeah, many such cases. You know, like there, there there is— I once was given feedback, or maybe not even once, maybe multiple times, given feedback about like, hey Tammy, you get like really emotionally invested in things. And so for example, everybody on my team used to know if I was having a good day or a bad day.

And it would get to the point— and I got this feedback from two different managers, and I really struggled to hear it because it felt like way too much pressure on me. But the feedback was a lot of this team feels how you feel. You sort of have a disproportionate impact on the mood. So if you're excited about something, we're all excited with you. But if you're doubting something, if you're down on it, if you're bearish, if you're just in a bad mood that day, that affects how other people feel.

That's like a point of maturity that you have to get to if you want to lead a team or even be a meaningful contributor to a team, right? Learning to— so what I've tried to do is make myself a really predictable person to interact with, right? So I might be having a good day, I might be having a bad day, but you shouldn't be able to tell. Um, you know, being delightful to work with. And then maybe finally, yeah, there is this piece of not just in selecting the books, but in general, in not cutting corners.

You know, there have been and even in this year, several opportunities where we could have kind of just gone with a cover, and that would have made our lives easier, right? We have two books this year that are coming out later than we planned them because we weren't happy with the covers that we had picked. But again, I think how you do one thing is basically how you do everything. And the hard thing, especially for somebody like me who often just wants to get it done fast and move on to the next thing is to just internalize the idea that, you know, we're not going to let this go.

And that means that there is a trade-off between— sometimes, hopefully increasingly in the future there won't be— speed and execution. Yeah. Speaker A: The first book you worked on at Stripe Press, I believe, was The Making of The Prince of Persia, or the republishing of The Making of The Prince of Persia, which is— I, I read a good chunk of it recently. And in one sense, it's just this amazing look into what it actually looks like to make something without narrativization or editorialization. It's basically just his journals. You are also a prolific journaler, as I understand.

I think you've journaled for at least 8 years. Aside from being the— hopefully the, the content or the fodder for the Tammy Winter book someday, what keeps you journaling? Speaker B: One of the things I tend to do that at some point I realized was not super productive is is just purely verbal processing. Yeah. For me, there is nothing better than having the same conversation. Yeah, just riffing about the same thing 8 different times. I really will call Alicia, then Sab, then you, then Abe, and just have the same conversation again and again.

There's— Speaker A: I get joy from that. And you find new things too. Speaker B: You do find new things, but of course, like, it ends up being on some level unproductive. But again, that's maybe some of that, like, social substrate that really matters. Yeah, but on the other hand, it's nice to have a contemporary record of just— it's like a temperature check, just how things are going. And for me, it does a couple of things. One, it is a way to actually process things and make progress on whatever it is that doesn't rely on me having to have somebody else there, right?

We haven't talked about this at all in this conversation, but you and I are both Enneagram 7s, and I know there are a lot of people who think it's like one step up from astrology. Yeah, but to the extent that you think it's real, one of the characteristics of a 7— Speaker A: they're inputs to realness at the very least. Speaker B: Yeah, they're, they're inputs to realness. One of the characteristics of a 7 is that the hardest thing for them to do is to sit in silence and to self-reflect.

Yes. There are things about themselves or their own experience or whatever that they are kind of scared of. And I think there is absolutely a balance to be drawn between completely lacking self-reflection and therefore self-awareness and navel-gazing. But I found it useful to actually process things by writing about them. Yeah. And what's really interesting is that I'll go back and look at things after the fact. And what I found really helped— it's a way for me when they're really negative memories, you know, something bad happened, it's a way actually to get through it more quickly because you're able to kind of name it, identify it.

And what you will find often, I don't go back to my journals often, but sometimes I get surprised and really saddened by these periods that were extremely difficult where you really can't see past yourself. You know, as you're right, it's like day after day of just, I'm just in this incredibly low mood or state and it's really hard to read. But, you know, human memory is an incredible thing because eventually you forget that stuff. Yeah. Yeah, it's so frustrating. You know, thank God we forget. And you know, we could go on a whole tangent about why ChatGPT's memory function is so frustrating to me, but we'll save it.

Mm, next time. But on the other hand, um, it's also really lovely to have a record for me of these wonderful people who float in and sometimes out of your life. Yeah. Right? And so for everyone, there's always a really fun thing where the first time somebody appears in my journal, I find that really interesting. Um, I find it interesting when people, you know, make multiple journals journals now. Like, you are definitely in my journal somewhere, right? And so it's like a record of people that I love, which I also think is great, you know.

Like, there are multiple days of just talking about— we were just in Montecito, right? And, you know, there's a week's worth of reflections about why that week was both such a catalyst and also a retreat and a sanctuary. Speaker A: Yes. And, and by the way, we are unreliable narrators. Both— of course you're an unreliable narrator when you're journaling, but that's a different cut on it than the, like, memory of the memory you have. Totally. I found, like, it's a— it's a really great way to stay in touch with my past self and maybe my future self and acknowledging that we're all just, like, subjectively experiencing this version of it.

Speaker B: Yeah, it's just so funny, you know, like, what goes into what we choose to remember and what we choose not to remember. I don't know, maybe to your point about, you know, keeping yourself in touch with your past self and your future self, Um, maybe it makes me more attuned to the present moment because I'm totally prone to daydreaming. Yeah. Um, and to thinking like very far into the future or, you know, just ruminating on something in the past. And so, um, just in the same way that a gratitude journal, I think, makes you much more likely to look for things to be thankful for throughout your day, this journal is also maybe just keeping me more attuned to the present moment.

Speaker A: Hmm. We've talked a lot about like the content of writing, uh, and the books that you publish and so on. What, maybe from a more like stylistic standpoint or whatever else, what actually makes for good writing? Speaker B: There are a lot, I guess, of ways that I could answer this, but maybe I should focus on the domain that I know best. Although increasingly I'm wondering if we should start reprinting classics that are like in the public domain. But we'll stick with nonfiction. The best writing is first and foremost clear, right?

If you're going to effectively communicate something to me, I have to know what you're saying. And I think the way that this often goes wrong is that people will read just enough to be able to grok a particular writer's style and try to copy that. Mm. And that means that the writing just becomes often just, like, way less interesting, or you're using more complicated terms than you need to to explain something very simple. Um, you know, the prose is, like, overloaded with all of this stuff because you think that that makes good writing.

But the best writing is fundamentally clear, especially if it's nonfiction. Speaker A: Yeah, it's in service of something. Yeah. And as a result, like, too much of the writing can get in the way of actually explaining or teaching. Yeah, or storytelling. Speaker B: Yeah. I think maybe second, a lot of the best writers have somebody in particular in mind, so they're not necessarily writing to the void. And sometimes that person is themselves. Yeah, right. Like, Brian Potter, I think, is a really great example of somebody who is pretty much when he's writing, he's writing to answer a question that he has.

And you get to come along for the ride because he's the kind of person who will spend, you know, days or whatever reading 500 sources just to answer the question. And so he doesn't, like, sit down every Monday at a blank sheet of paper and say, all right, you know, what are we going to write about this week? He has just these natural questions about the world. I think, by the way, this is one of the things that he, Nadia, and Stuart have in common. There's just this sort of natural curiosity and you can tell it spills out of the writing.

You can tell, you know, this person has deeply considered something. Maybe that's just something that makes it more enjoyable for me. Speaker A: That's part of, that's part of great writing. Speaker B: But at the same time, it doesn't overexplain, right? There's a principle that Stripe has, which is just speak up to the reader, right? You can trust that the person that you were writing for does not need you to spell out the implications of every single argument. One, that would make the piece way too long, but two, you know, there is some sort of competence that you want to assume on the part of your reader.

And the way that we think about things is if there is something that they are unfamiliar with, they'll just look it up. He'll figure it out. Yeah, Scissor Statements. Yeah, exactly. You know, had you not said that, you deprived people, the sort of keen reader for— or listener, I guess, in this case— from discovering that blog post on their own. Phone. And then that might have taken them down a rabbit hole. And then maybe they're reading I Can Tolerate Anything Except the Outgroup. And maybe they're reading Scott's reflections on bupropion, and so on and so forth, right?

So fine, whatever. But it was a good explanation. And yeah, you don't have to overexplain everything. But I also think, and you know, you don't always need this, but good writing, good nonfiction writing can be just as fun and can take you on just as much of a journey as good fiction writing. Yes. They're doing different things, right? But, you know, I finally earlier this year, and I sent it to our group chat, read Frank Sinatra Has a Cold. And it's amazing. It's like a, you know, I get why it is the sort of canonical profile.

You know, this profile is written without Gay Talese ever speaking with Frank Sinatra. How do you construct this piece of writing that is a journey that is really, truly fun to read, right? You have this sort of digression into his mother. And in fact, you realize, "I want a whole profile just of her." You know, you get his weird relationships with his ex-wives, his super sweet relationships with his family, his perfectionism, his, you know, sort of more unsavory connections. And you get all of this, He's— because he's able to write in such a way that it's more like music than it is like sort of straight essay.

Speaker A: Yes, such a clear voice and yeah, yeah, yeah. Yeah. Speaker B: And then, yeah, you know, ideally you'd end up in this point where I'm reading it, I always know when I'm reading this person's writing. Right. Now, again, not having that doesn't mean your writing is bad, but I do love, I do love seeing a signature. Speaker A: You are known— I haven't read much of it myself, but you are known, as I understand, to write very deep essays on various topics and send it to a small group of people or one person.

How do you think about— and obviously this applies to journaling too, um, and you talked about this with, with some of the authors you mentioned, but yeah, how do you think about audience in terms of your writing and the public-private-ness of it? Speaker B: Yeah, I think it is just like layers of irony that I have my particular job and like I refuse to write publicly. I don't even really tweet that much anymore. I think there's like a scale that you hit at some point. Well, okay, there are a couple of reasons for this.

One, Twitter in particular used to be a place where you could, you know, A/B test thoughts. You didn't have— it wasn't the sort of norm of Twitter that everything that you tweeted was this kind of complete thought. I guess part of what I'm trying to do when I write is to just figure out what I think about something. I guess maybe same as anybody else, but I don't really write unless I'm moved to anyway. And I used to do a lot of this kind of thinking on Twitter when Twitter did used to be this place where, you know, you can A/B test thoughts.

You're just testing out a belief that you have somebody will certainly come along to correct you. Um, but it was a little unfinished, and that was allowed. Speaker A: Yeah, and it's okay. Speaker B: And you can in fact go on this like shared inquiry together. It's kind of interesting and beautiful. But that's just not really— Twitter is totally professionalized, so it's like our LinkedIn or something. Yeah, you know, every tweet is a chance to, uh, you know, every tweet is a chance to get hired by somebody or whatever. And there's just like all these implications to what you tweet, and I just don't think I enjoy So I like to— I like the intimacy of a personal correspondence.

You know, I like knowing that I can still have that dynamic that was so great on Twitter with people I care about, you know, people I want to hear from. So you're not dealing with people who are, you know, some— there's some— if you get an audience large enough, there's some core part of your audience, or if your tweet escapes containment, that is determined to misunderstand you. It is a classic. You know, you tweeted about pancakes, so you hate waffles. It's like, that's a whole new sentence. Yes. Yes. And I just don't have enough self-control to simply ignore those people anymore.

You know, I will, if I'm not careful, end up 2, 3 replies deep to, you know, egglover624389. That's not a way to spend your day. I am, however, a prolific Redditor. Oh wow. Speaker A: I would not have guessed that. Okay. Speaker B: Um, Um, but you know, besides that, yeah, I love the intimacy of a personal correspondence. During COVID Ryan Ohrbach and I had this long-running thread where we just emailed each other every day, just something that was on our minds. And they were very different in terms of what we were thinking about day to day.

You know, there was one day when I wrote about what it's like when people put you on a pedestal and like how sort of dehumanizing that can be, or what happens when you do that to other people. So, there was one day where I just wrote about management, one day where we wrote about interior design and what happens when you have a place that is signaling to whoever— like, the interior design of condemned places, right? So, places that say to you, at least in America, that we just really dislike you, you have done something wrong to end up here.

And so in a lot of places that might be mental institutions, Sometimes public housing, right? We, I think, often take this very punitive view of public housing. Like, it shouldn't be that nice, you know, it shouldn't be beautiful. A lot of times this is the approach people will take to schools and, you know, prisons and whatever. Okay, so we're just day to day, we're thinking about something, we're just kind of exploring it together. And that was really fun. And then every so often, I'll put together these curriculums for myself. You know, I'm just, I'm, I have my woman curriculum, and I'm just reading all sorts of of things, you know, I'm reading, I'd never read Nora Ephron.

I did the Woman curriculum. I just really value this group of people, which again, you know, a lot of what we all have in common is that we're really curious, really responsive, and we love the written word. And so, you know, you can, you can just inquire. Tyler, Tyler says this in a piece recently, you know, inquiring together. And I just want to inquire together where it feels most fruitful. And right now it doesn't feel I don't know if I feel like Twitter is that, but maybe I have this Substack that's just sitting there and I haven't done anything with it.

But, you know, maybe, maybe I'll do something. I mean, here I am on this podcast. Speaker A: Here you are. It's a good reminder though that writing is— in anything creative, but maybe especially writing— is it doesn't have to be one to theoretically everyone. Yeah. Do you have any advice for reading? Do it. Wow. Tammy Winter of Stripe Press on reading. Do it. Do it. Speaker B: You know, like, uh, just read widely, read a lot, read all the time. But actually, the best advice that I could give on reading is— has been given by somebody else, and it's a guy called Henry Oliver.

He's based in the UK, and he has a Substack called The Common Reader. And what I love about him is he is such a passionate advocate for reading, but specifically for reading the classics, you know. I mean, there's a reason why certain books have just endured over time. And so he's a huge advocate of reading the classics, of letting yourself be challenged. And today there is way more infrastructure than there has ever been in human history to do that, right? So to not get caught up in the, you know, if you're reading Madame Bovary, right, like there's just the difficulty of reading something that was in a different language and is now in English, or just the difficulty of reading prose that you're not used to if reading, let's say, Bleak House or Middlemarch.

But maybe, like, a fun thing that I can offer here is that I think just like people can get writer's block, you can get reader's block. Mm. And I was going through that. You know, I have to read as, like, a sort of function of my job. But there was just, like, a point where I just stopped reading for pleasure. And the thing I did there was pick up the least nutrient-dense, most ridiculous novel that I— I mean, it's just like, it's one of those novels where you know where it's going, like, 30 pages in, but you have to keep reading.

It was called In Five Years, okay, by Rebecca Searle. And, you know, if you were to Google it, you'd see that in fact it is like very well received by lots of people. Like, a lot of people love that novel, and there's something wrong with it. But, you know, I'm not deluding myself, this is not, you know, hard literature, right? But it was like the thing that I needed to sort of break the ice back and start reading again. And, you know, you can, you can just start by reading a little bit at a time.

A lot of people's, a lot of people's challenge is that all of our attention spans are just totally shot. And so, you know, the way that you pick up that habit again is the same way that you eat an elephant, like one bite at a time. Speaker A: Why do you love biographies? You love— I love biography. Speaker B: I love a biography. I think it's related to what we were saying earlier. Interesting life paths don't— they often don't repeat, but they rhyme. And if you're really, really interested in people, one place that you can go and just immerse yourself in stories about people is biographies.

Now, there are all sorts of features of biographies that make the medium limited and also make the medium interesting. I am particularly interested in people's early lives. I find— okay, the thing that's interesting about the fact that a lot of, uh, interesting life stories rhyme is that you can draw a lot of even, like, let's say, courage from people's life stories, right? You can read about people— often the biographies that I'm most interested in, um, are not like the ones from 20 years ago, but in fact from like 100 years ago.

Because if we care about things like agency, you can learn way more from the fact that Walt Disney, because his mother wouldn't let him go off and fight in World War I, you know, if you were younger than 18, you had to literally have a permission slip from your parent. Because she wouldn't write that for him, he forged her signature. Or Booker T. Washington, right? His autobiography is called Up from Slavery. And he walks across state lines for the mere possibility of an education, right? Like, he walks for days. And somewhere in the middle of the walk, His mom actually dies, so his brother— He's, like, squatting in some cabin in the woods or something.

His brother has to come and tell him that their mother has died, and he just keeps going. And he finally gets to the school, and when he gets there, there is, again, no guarantee that he's going to be allowed to be educated. But what ends up happening is that he— he ends up being, like, something akin to the janitor, right? So when he's not taking lessons and he's not studying, he's also kind of cleaning the school. But sort of this education is totally formative for him. Or to take a totally different example, you know, Anna Wintour was a nepo baby, you know?

But that's not what's important about her. What's really interesting about her is that she, from a very early age, just called her shot constantly. Right? You know, she's sitting across from Grace Mirabella, and, you know, Grace, "What job do you want?" "Yours." So you can borrow a lot from, you know, interesting people's life paths and I certainly have. And, you know, those are the kind of lives that I'd like to rhyme with. Sometimes in other people's stories, you can pick out these really important traits that you just wish you had in your own life.

And so maybe in the past, what I've done is, like, borrowed, borrowed things I wish I saw in myself. Oh, wow. So, like, borrowing courage, right? Let's take Teddy Roosevelt. About. Teddy Roosevelt experienced a lot of tragedy in his life. His mom and his wife die on the same day— Valentine's Day, mind you— and it's also the day that his daughter gives birth, or his, his wife gives birth to his daughter Alice, who he names after her mom. And he writes in his journal that day, "The light has gone out of my life."

And you see that he has basically, like, stops living for a while. He kind of just, like, leaves his child with his sister, Bayme, and he just goes. He just leaves. He has to go. But I first found that documentary when I was reeling from two deaths. My grandmother and my grandfather died about a year apart. And I'd never before that had anybody really close to me die. And I felt— there was just so much grief that I had experienced about that because I'd never had to do that before. And so maybe something you're doing sometimes, like, if we're honest with ourselves, is sort of borrowing the qualities that we wish we had in ourselves.

And, like, good fiction can often do this too. Totally. You know, this is I think part of the reasons why good children's literature is so good and so important, right? It's able to teach— it takes young children seriously. And it sort of tries to give them the tools that they will need to confront the things that are inevitable in life, right? They will face grief, they will fail. And people like— let's just take an example— S. Lewis, or, or Brian— I don't know if it was Jacques Wez or Jacques. He was American, so probably Jacques, you know, just whatever the grossest understanding of that, that pronunciation is.

He wrote the Redwall books that I used to love. I obsessed with those books. They have a fundamental respect for their reader. And so yeah, I think a lot about— I think a lot of people who read a ton also think this way, right? Borrowing these qualities from, from the people they're reading about. But also, it's just fun to read about people's lives. Like, you know, what was going on? You know, because you get the highlights, but it's nice to dig into the— I love the minutiae. Yeah. Now, there are some real limitations to biographies, right?

Which are that that, you know, sometimes they're only as good as whoever is capturing it, right? And there's a lot that you just leave out because you have to make it a clean story, right? Often in a biography, you want there to be sort of a through line of the story, right? You almost begin with the conclusion in mind. And, you know, that's not the worst thing in the world, but it does color how you have to read biographies. But a cool thing about biographies is that sometimes the best ones suggest Who should have a biography that doesn't, right?

Cool. So you read Walt's biography and you realize, where's the biography of Roy? Or you read, um, Frank Sinatra Has a Cold and you realize, I need a biography of his mom. What an interesting woman, you know, kind of force of nature. And, and that, that's kind of fun. I love that. Speaker A: My final question, it's, uh, higher on the difficulty, so I'm sorry, uh, but no, no. 3 prospective future biographies I want you to give me a title for. Okay. Um, the first is Patrick Collison, the second is your father.

Okay. And the third is you. This is insane. Speaker B: Um, okay, if we start with Pat— hopefully he never listens to this. Yeah. Speaker A: Um, that should probably be the easiest. No, at least you have the most distance. Speaker B: Well, he's, um, I think what's interesting is that, like, a lot of people will just, like, assume what he would be interested in. And in fact, like, he has a lot of wide-ranging interests that aren't what you'd expect. For example, he is obsessed with great architecture. Oh, I think— okay, I think I have an idea.

So his prospective biographies would either be two things. One would be a really obscure term that comes from like biology or something that then has an extremely long subtitle that gets unpacked. Speaker A: But it's also a metaphor. Speaker B: Exactly. That gets unpacked in the foreword. Okay. Or just like a very elegant, simple term. I think maybe it's the latter because one of the people that he really loves and admires is Christopher Alexander, and he takes a lot of inspiration from— and there's a lot of relationship between things like a pattern language and building great software.

And so I think maybe he would take something from architecture or some— something from a totally unrelated field that is like an elegant and beautiful term. So something like a pattern language, something like that. That's not exactly it, but something like that. Or— Speaker A: We also have to make sure Christopher Alexander gets mentioned on every interview I do. So I'm glad you said that word. Yeah, exactly. Speaker B: It's like literally illegal if it doesn't happen. For my dad, one of the things, you know, one of the great things about having a great dad is that while you have the period that is just kind of a canon event, right?

This period where nobody knows more in the world than you do. I've never known more than I did when I was 18. Of course. Yes. Um, is that, you know, if you were so fortunate to kind of keep having your dad around, you eventually get to this place where you're like, you could just call him every day and be like, you know what, remember when you told me, you were right about that, Dad. The biography is not, you were right about that, Dad. It's something he used to tell me, which I used to get so angry about because I took it totally personally, which is, you know, I know that you will always be able to find happiness.

But what I really want for you is contentment. Contentment. And so maybe the title is contentment or something along those lines. And that means something very specific, right? You know, I travel a lot. I, you know, I love being professionally curious and trying a lot of things and whatever. But, you know, a really happy life and a really meaningful one anyway, is one where, like, every little thing that you do is imbued with meaning. And so you don't need to constantly be chasing these novel experiences. And that was something his mom told him.

And so I think that's probably my dad's. Hmm. Beautiful. Mine, on the other hand, it's like some tortured metaphor. No, um, uh, I don't know. I don't know. I, this is a total cop-out, but I think this is a little bit like talking about tacit knowledge where you need a little bit of perspective to be able to name something. Like, you actually would— it would actually be better for you to have somebody that, like, really loves you or really hates you, I don't know, suggest a title. Because it's hard, I think, to— it feels really self-aggrandizing.

I don't want to answer this. I don't want to. I don't want to. Speaker A: That's a fair cop-out. Hmm. Yeah, I think some distance and some— you have, you have a lot of things left to but yeah, my, my— Speaker B: oh my God, that is a trend though, people writing memoirs at younger and younger ages. Speaker A: That's true. Yeah, maybe it's time. I was just gonna say, um, the, the most Tammy thing to me is that is inescapable is just you, you really— we talked about it a lot— you really truly deeply love other people, and it's something I admire a lot.

Speaker B: Yeah, maybe something— that's really kind— maybe something along those lines. Yeah, we'll keep workshopping it. Speaker A: I have to come up with a title for this episode. Uh, Tammy, thank you very much. Really genuinely mean it. This was wise and fun and funny and full of life. Speaker B: Um, someday we'll tell the story of everything we had to do to get this episode. Speaker A: It was all worth it. All worth it. Genuinely, despite, uh, yeah, some technical difficulties. Speaker B: Thanks, Jackson.