![[23-Tammy_Winter.jpg]] *Dialectic Episode 23: Tamara Winter - Tacit Trust & Caring Curiosity - is available on [Spotify](https://open.spotify.com/episode/2HCjobZd3o4X7fEdfuYXFs?si=c3fde680d7cc4f7d), [Apple Podcasts](https://podcasts.apple.com/us/podcast/23-tamara-winter-tacit-trust-caring-curiosity/id1780282402?i=1000719449124), and [YouTube](https://youtu.be/rptQNq2ux90?si=2GpixWLq4aSt1HyY), and all podcast platforms.* <iframe data-testid="embed-iframe" style="border-radius:12px" src="https://open.spotify.com/embed/episode/2HCjobZd3o4X7fEdfuYXFs?utm_source=generator" width="100%" height="152" frameBorder="0" allowfullscreen="" allow="autoplay; clipboard-write; encrypted-media; fullscreen; picture-in-picture" loading="lazy"></iframe> <iframe allow="autoplay *; encrypted-media *; fullscreen *; clipboard-write" frameborder="0" height="175" style="width:100%;max-width:660px;overflow:hidden;border-radius:10px;" sandbox="allow-forms allow-popups allow-same-origin allow-scripts allow-storage-access-by-user-activation allow-top-navigation-by-user-activation" src="https://embed.podcasts.apple.com/us/podcast/23-tamara-winter-tacit-trust-caring-curiosity/id1780282402?i=1000719449124"></iframe> <iframe width="560" height="315" src="https://www.youtube.com/embed/rptQNq2ux90?si=2GpixWLq4aSt1HyY" title="YouTube video player" frameborder="0" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share" referrerpolicy="strict-origin-when-cross-origin" allowfullscreen></iframe> # Description Tamara Winter ([X](https://x.com/_tamarawinter)) is the Commissioning Editor of [Stripe Press](https://press.stripe.com/), where she exercises her taste to identify the knowledge and "ideas for progress" that matter most in alignment with Stripe's mission: to increase the GDP of the internet. "Tammy" worked at the [Charter Cities Institute](https://chartercitiesinstitute.org/) and the [Mercatus Center](https://www.mercatus.org/) at George Mason University, which is chaired by [Tyler Cowen](https://x.com/cowenconvos). Tammy is obsessed with tacit knowledge and the illegible parts of the world that actually support so much of our lives, work, and societies. This includes taste, charisma, relationships, and a wide-range of load-bearing infrastructure that supports healthy and trustful societies, from small-talk and manners to hidden forces that prevent anti-social behavior and maintain safe places to live and work. We discuss this and more, including how she selects the ideas worthy of Stripe's audience, her unique career path, her refreshing take on agency, her standards for herself, reading and writing, and how she chooses how to spend her time. Above all, Tammy's incredible love of other people shines throughout the conversation. # Timestamps - 2:09: Taste, absorbtion, and influences - 10:54: Deploying your taste - 15:49: Ideas that matter and taking yourself seriously - 22:13: Aesthetics - 24:16: Choosing Teachers and Authors - 28:15: Charisma & delightfullness privilege - 34:59: Living a relational life - 44:07: Trust, social scaffolding, and small talk - 51:01: Erosion of social norms, low-trust environments, and load-bearing infrastructure - 1:02:17: Cultural arson and the dark sides of "you can just do things" - 1:15:44: The healthy kind of agency - 1:20:45: Tammy's N-of-1 path and who she aspires to rhyme with - 1:28:38: Red herrings of success and focusing on outcomes - 1:32:22: Assortive everything - 1:37:52: Personal and professional standards - 1:43:06: Journaling, great writing, and audience - 1:57:29: Reading & Biographies # Links & References - [Patio11 (Patrick McKenzie)](https://x.com/patio11) - [Sasha de Marigny](https://x.com/sashadem) - [Everett Katigbak](https://www.typochondriac.com/about) - [Stewart Brand](https://x.com/stewartbrand?lang=en) - [Nadia Asparouhova](https://nadia.xyz/) - [Brian Potter](https://x.com/_brianpotter) - [Cedric Chin](https://x.com/ejames_c) - [The Art of Doing Science and Engineering - Richard Hamming](https://press.stripe.com/the-art-of-doing-science-and-engineering) - [On Self-Respect - Joan Didion](https://yale.learningu.org/download/85e1ca3695ab0e000f2c8bf10be1a59d/S574_didion_respect.pdf) - [Working in Public Blog - Nadia Asparouhova](https://nayafia.substack.com/p/22-working-in-public) - [Scaling People - Claire Hughes Johnson](https://press.stripe.com/scaling-people) - [Claire Hughes Johnson](https://x.com/chughesjohnson) - [High Growth Handbook - Elad Gil](https://press.stripe.com/high-growth-handbook) - [Elad Gil](https://x.com/eladgil) - [Virginia Woolf on Montaigne](https://x.com/_TamaraWinter/status/1927409229276557695) - [Ava on Tammy](https://www.avabear.xyz/p/always-on-your-side) - [Old Enough!](https://en.wikipedia.org/wiki/Old_Enough!) - [Sort By Controversial - Scott Alexander (Scissor Statements)](https://slatestarcodex.com/2018/10/30/sort-by-controversial/) - [Scarf tweet](https://x.com/_brentbaum/status/1923019796427256121?s=46) - [Broken windows theory](https://en.wikipedia.org/wiki/Broken_windows_theory) - [Satya Nadella - Dwarkesh Podcast](https://youtu.be/4GLSzuYXh6w?si=S6xsrxlHTY6RTynF) - [Simon Sarris](https://simonsarris.com/) - [Tammy's advice to young people](https://x.com/_TamaraWinter/status/1803439254518837320) - [Anna Wintour](https://en.wikipedia.org/wiki/Anna_Wintour) - [Pamela Harriman](https://en.wikipedia.org/wiki/Pamela_Harriman) - [Esther Coopersmith](https://en.wikipedia.org/wiki/Esther_Coopersmith) - [Consuelo Vanderbilt](https://en.wikipedia.org/wiki/Consuelo_Vanderbilt) - [An Elegant Puzzle - Will Larson](https://press.stripe.com/an-elegant-puzzle) - [Lulu Cheng Meservey](https://x.com/lulumeservey) - [Maran Nelson](https://www.linkedin.com/in/marannelson/) - [Interact](https://joininteract.com/) - [The Making of Prince of Persia - Jordan Mechner](https://press.stripe.com/the-making-of-prince-of-persia) - [Frank Sinatra Has a Cold - Gay Talese](https://www.esquire.com/news-politics/a638/frank-sinatra-has-a-cold-gay-talese/) - [Why not inquire together more? - Tyler Cowen](https://marginalrevolution.com/marginalrevolution/2025/04/why-not-inquire-together-more.html) - [The Common Reader - Henry Oliver](https://www.commonreader.co.uk/) - [In Five Years - Rebecca Serle](https://www.goodreads.com/book/show/50093704-in-five-years) - [Walt Disney: The Triumph of the American Imagination - Neal Gabler](https://www.goodreads.com/book/show/118824.Walt_Disney) - [Up from Slavery - Booker T. Washington](https://www.goodreads.com/book/show/827685.Up_from_Slavery) - [Anna: The Biography - Amy Odell](https://www.goodreads.com/book/show/59366098-anna) - [The Rise of Theodore Roosevelt - Edmund Morris](https://www.goodreads.com/book/show/40929.The_Rise_of_Theodore_Roosevelt?from_search=true&from_srp=true&qid=6Aoe2PlP4A&rank=1) - [Brian Jacques](https://en.wikipedia.org/wiki/Brian_Jacques) - [A Pattern Language - Christopher W. Alexander](https://www.goodreads.com/en/book/show/79766.A_Pattern_Language) # Transcript **Jackson:** Tammy Winter. **Tamara:** Hi. **Jackson:** It's good to be with you. **Tamara:** It's good to be here. **Jackson:** The theme that will bound most of the conversation is something that feels representative of you: this notion that there is one part of the world that is legible, codified, very explicit, well understood, and articulated. Then there's another part of the world that is more human—hidden, illegible, or at least not as explicit, much more implicit. You're more interested in that part of the world than almost anyone I know. ## [00:02:09] Taste, absorbtion, and influences **Jackson:** I want to start with a topic that I know you have complicated feelings about, and yet also have a lot of insightfulness about. It's inspired by a conversation we had at dinner with somebody who you work with. I asked this person what makes Tammy so good at what she does, specifically at Stripe Press. Their answer was twofold. The first part was obvious: there's a bunch of things that go into the day-to-day of being able to publish great books on the tactical side, the structural side, and the mechanistic side. But the second part of their answer about what makes you great is taste. Specifically, what they had to say about it was that unlike in most domains where there's a ceiling on how great you can be, their answer was that taste is something that scales infinitely. That is what makes you so special. Taste is a complicated idea. It's been talked about a bunch recently, particularly in tech and Twitter land. You also talk about this notion, at a more foundational level, that people don't really know what they like and why they like it. You have a clear view, whether it's expressed or not, on what you like, why you like it, and what you believe in. So my first question is, to the extent you can, I'd love for you to identify the threads or the patterns that run across your taste. **Tamara:** I'm not sure I can do that because taste is so nebulous. Every time this conversation comes back into the zeitgeist, I feel as though 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. 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. We can talk about tacit knowledge later. When I think about how I developed my taste, a big part of it starts in childhood, when you're young. **Jackson:** Right. **Tamara:** The first part of taste is absorbing a lot. Everybody has to be honest with themselves and 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 is my father's music taste. I'll be the first person to tell you on any given day. You can almost break it down to: if my dad likes it, I like it. **Jackson:** Right. **Tamara:** This is for a lot of reasons. I remember growing up, my very first concert—I don't know if I've ever told you this—was Earth, Wind and Fire. **Jackson:** I think you may have told me this, but that's amazing. **Tamara:** It was Earth, Wind and Fire and Chris Botti. **Jackson:** Do you have any idea what year this was? Or what age? **Tamara:** I was eight or nine. I remember it. I had grown up listening to "Boogie Wonderland," "Fantasy," and so on. The first part of taste is absorption. **Jackson:** Yeah. **Tamara:** The other part of this, as it relates to my work, is that I read a lot as a kid. It's hard to have a finger-feel for what good writing is if you don't read a lot. **Jackson:** Right. **Tamara:** It's just really hard to do that. I think one theme of what we'll talk about today, culturally, is that everybody wants the version of mastery with the least friction and the least amount of work possible, which I totally understand. But the first part is absorption—just getting a lot of references. I grew up with a lot of references. There was a lot of Motown, but there's some country in there and some popular music. My dad is a pop girl, too; I don't know that he would describe himself as such. There was a lot of weird British 70s experimental stuff. You have to first have a really broad base to sample from. The second piece of this becomes pattern recognition: knowing what you like and why you like it. For me, working at Stripe has been 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 a weird time. My first day was February 24, 2020. **Jackson:** Amazing. **Tamara:** I moved from D.C. to San Francisco to work at Stripe. I had three weeks between getting the job and moving, and one week later, we went remote for COVID. I was in this job, having never done anything related to book publishing or comms. The Charter Cities Institute was about four people when I left; Stripe was about 2,800 at the time. I was completely out of my depth and out of home as well. I didn't start off at Stripe commissioning books, but a lot of the work my team did—this extremely nebulous team that worked on everything from Atlas to Indie Hackers to Patio11 and everything he entails, to Stripe Climate, which is now Frontier, to weird side hustles for Patrick and John—that team's secret sauce was its taste. It became very clear very quickly that everybody around me had a very clear idea of what excellent looks like and what we were trying to do, even though we had no clear mandate. The ability to absorb the best or most interesting parts of other people that you trust is a huge part of how you form your own taste. **Jackson:** Yes. **Tamara:** 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. That was people like Sasha Demarini. She's now the head of comms at Anthropic, but she was the ringleader of this team. Or Everett K. Back, who is a filmmaker by trade. He was the seventh designer at Facebook and one of the first in their really experimental lab. Then he went on to Pinterest and then to Stripe. People like Patio11—those were the people that I was learning from, and of course, Patrick as well. That was extremely fun because their job is to be professionally curious. **Jackson:** It's a way of being, almost. **Tamara:** Yes, it's a way of being—a really active curiosity. That means that you can turn yourself, as Sasha calls it, into a truffle pig for substance. You're always burrowing for the most interesting things you can find in any domain. **Jackson:** You pointed out something really special, which is apprenticing to curiosity by osmosis. It's interesting, too. Maybe the world has less apprenticeship broadly, but so many things are like that. We all have the experience of the older kid or the older sibling, and you want to like what they like for a little while. Or the musician who's trying to sound like somebody and ends up sounding like themselves. I don't know if there's enough conversation about that part of the taste thing. So much of it is relational because there are people you admire or respect, and part of it is even just getting closer to them. By doing so, you also get to see through their eyes, and that's a really cool thing. **Tamara:** It's a very human experience. Our culture moves in waves, and America has a very particular relationship to individuality. This is just the natural state of becoming a human. Everybody has influences. You start with your parents, your peers, and such. What's so interesting is everybody I know who's amazing at what they do is pretty explicit about their influences, whether that was an artist wanting to sound like somebody else or just being incredibly inspired by their style of singing and their way of performing, and then eventually finding their own. It's really interesting that there is some sort of disdain for people just admitting that they are heavily influenced by these seven people. **Jackson:** Of course, I'm not perfectly original. **Tamara:** This is the experience of being human. I've been completely influenced by you since we've been friends, and I would imagine the other way. I feel very shameless about this. To your point, what's really hard is choosing your influences, choosing what to ignore, and choosing what gets right access to what I think about any given thing. That's the hard thing. **Jackson:** That's a really refreshing answer. ## [00:10:54] Deploying your taste **Tamara:** Maybe more interesting than any of that is: can you deploy your taste? That is the thing that is the hardest. You can spend years just watching all of these people I mentioned do things. At some point, I became the commissioning editor of Stripe Press. When you get there, ideally, you can use this knowledge and this judgment that you've accumulated over the years to make decisions about what to create or, in my case, what to commission. If I read a proposal, I can pretty instantly tell you that's a Stripe Press book or that's not a Stripe Press book. I don't need to read it five times to figure it out. **Jackson:** There's some kind of high-dimensional algorithm that you've developed over a long period of time that might not even be super easy to put into words, but it's clear when the input comes in. **Tamara:** It's not easy to put into words, and that's why it's tacit knowledge. For example, if you look in our catalog at people we've either published or are about to publish: Nadia Eghbal, who wrote \*Working in Public\*; Brian Potter, who wrote \*The Origins of Efficiency\*, which is not out yet; and Stewart 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. **Jackson:** I connect to this because I have had the same experience with the podcast. **Jackson:** I have groupings like you just described. Obviously, all the Stripe Press authors aren't in the same group, but I've noticed these retroactive patterns and that sometimes there's overlap. Nadia, whom you mentioned, and I recently interviewed Yancey. There are direct connections, but there are also these threads that connect in hindsight as they come together. One of the things I've told people about how I choose people to come on the show is if I threw a dinner party with all the previous guests, would this person be a good add? **Tamara:** Can they hang? **Jackson:** That's basically the only codified version of it. It's very similar to what you say, which is I have a clear sense of yes or no, but I can't really tell you why. It's the same type of thing. **Tamara:** It's this kind of automatic judgment. 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. At this point, it's an automatic judgment. It's great because it saves me time. I don't have to think for long periods about whether or not this person belongs in the catalog. It's always pretty clear. **Jackson:** One last thing on this that I really admired in your answer is that the part of the taste conversation that most comes up is, "Does somebody have good taste?" It's this hindsight evaluation: Is their evaluation ability good? You didn't really talk about that. You talked about the thing on both sides of it, which is inputs and influences all the way back to your dad's influence on your music. That's how all taste is developed, whether by osmosis, what we read, or where our attention goes. And then you talked about deploying taste—actually doing things with it. My sense is that's one of the reasons the taste thing has become so overblown and empty. It's just, "Does Tammy have good taste?" What does that mean? Good taste in what? That's way less interesting than asking what inputs are feeding me. To extend the word "taste" to what it literally means: 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? **Tamara:** Exactly. I don't think we need another cultural critic. I think we have enough. I am increasingly uninterested in cultural analysis and way more interested in whether you can deploy it. It's like the joke, "If you're so smart, why aren't you happy?" If your taste is so good, why aren't you deploying it anywhere? **Jackson:** That's heavy. **Tamara:** That's a big challenge: learning how to move from, "I know what I like and why I like it," to taking what I like—all these patterns I've learned, all this judgment I've developed—and using it to make decisions about what to create or, in my case, what to commission. **Jackson:** It's really cool. **Tamara:** What makes that tacit knowledge and not explicit knowledge? Cedric Chin is probably the best person writing today about tacit knowledge. He's a writer, a business analyst, and a consultant based in Singapore. He describes tacit knowledge as the process of moving from conscious incompetence to conscious competence to unconscious competence. That's what we're talking about. Can you make these snap decisions? Can you figure out how to deploy something without needing to go through a laborious mental process? Can you deploy it? That is basically all I care about these days. **Jackson:** That last bit is the master who can't even necessarily explain why they do what they do. ## [00:15:49] Ideas that matter and taking yourself seriously **Jackson:** You've said that the books we publish are a vote for ideas we care about and that what people see—their frames of reference—really affects what they do or don't create. In that theme of deployment, Stripe Press has two tracks. One is what you call turpentine: the very pragmatic, "here's how to do things." Then you have 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 tech company to be doing? **Tamara:** A lot of this goes back to who we're talking to and who we're not trying to talk to. I'm pretty uninterested in the media, but I am hyper-obsessed with the kinds of people who are like you. **Jackson:** Right. **Tamara:** People who are obsessed with and working to extend the frontier of human knowledge or human capability; who have a deep love for people, who think that people have an incredible capacity to create, and are themselves doing that. They tend to be extremely curious. They can tell when you're feeding them nonsense. They have a level of discernment, which means you can't just feed them anything. I'm hyper-obsessed with them because those kinds of people's feedback loop between idea and execution tends to be quite short. **Jackson:** Yes. **Tamara:** They think about something and they go do it. It doesn't mean it's perfect every time, but Nadia talks about this. **Jackson:** Yes. **Tamara:** My favorite part of the blog post she wrote when she announced \*Working in Public\* was that she talked about how she's obsessed with writing that makes things happen. **Jackson:** Yes. **Tamara:** Us too. **Jackson:** Right. **Jackson:** Ideas are high leverage for this demographic of people. **Tamara:** Totally. **Tamara:** You can incept these memes—they may or may not be good memes, but they're so sticky, and they're particularly sticky in this environment. To take one that has been beaten to death: "You can just do things." If you really internalize the idea that you can just do things, suddenly you don't make excuses. Things that don't seem possible become possible. We'll have to come back to why that phrase seems to be mostly deployed in service of antisocial actions later. That's what I really care about. I want anything that makes individuals think of themselves as actors who can mold the world. **Jackson:** Yes. **Tamara:** That doesn't necessarily always mean on a grand scale, but anything that offers people an internal locus of control. **Jackson:** Yes. **Jackson:** The crux of it is the world isn't happening to me exclusively, but I can actually assert myself upon the world. **Tamara:** One of my favorite books in our collection is \*The Art of Doing Science and Engineering\* by Richard Hamming. 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. So many people who are responsible for some of the most load-bearing pieces of either digital infrastructure or companies see him as an incredibly important frame of reference. The last chapter of that book is a chapter called "You and Your Research." It's a talk that I return to at least once a quarter. What stuck with me is that that message felt like the exact opposite of the cultural programming I was exposed to growing up. There is a lot of messaging that will come to you as a young person—or in my case, as a young woman of color—that I don't think is malicious, but wants you to think of yourself as a person to whom things happen. There is so much media and programming from all corners that asks people to demand less of themselves or to think of the world in terms of these impersonal, cold systems which determine everything. **Jackson:** It's the man. **Tamara:** It's the man. It's those politicians. It's those people. It's them. It's always them. “You and Your Research,” and by extension, \*The Art of Doing Science and Engineering\*, is a set of lectures that he gives during his time as a professor at the Naval Postgraduate Academy. 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.” That all starts with asking the right questions about the world. You're not likely to get anywhere if you don't ask the right questions. I want you to see nothing as more important than whatever your personal mission is in life. There's a sense of seriousness, of expectation, that emanates throughout all the pages. We're now 30-plus years past him writing the book, and you read it and you immediately feel convicted. **Jackson:** That's the best kind of writing. **Tamara:** It holds up. Tons of people that I really respect and have learned a ton from have that as a formative essay for them, and I do too. 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 should take yourself seriously. I don't want to make it seem like I was totally defenseless in the face of all this messaging that I got as a kid. But I grew up in a suburb of Dallas. My biggest frame of what success looked like to me was being a doctor, a lawyer, or an engineer. Now, some of that is also being Nigerian. **Jackson:** I was rereading "On Self-Respect" by Joan Didion, and there's a line in there where she's talking about character. It's exactly what you're saying. She says, "Character is taking responsibility for your own life." **Tamara:** People with self-respect know the price of things. They don't engage in an affair and then feel like, "It was you that made me do it." They don't throw rocks and hide their hands. They know the price of things. ## [00:22:13] Aesthetics **Jackson:** One other part of the Stripe Press taste that might seem trivial, but I sense you take very seriously, is aesthetics. What kind of heavier lifting or deeper impact do you think aesthetics have? **Tamara:** I really do think people judge books by their covers. The argument that we're making with Stripe Press is that we think these books and the ideas contained within them are important enough that if you internalize them, they will change your life. This could be you and your research, a journal about the making of a video game, or Claire Hughes Johnson's book about management if you're starting a business. We think that these ideas are worth the $30 or $40 that you're going to spend. **Jackson:** To buy the book and, much more than that, a bunch of your time. **Tamara:** Exactly. The median page count is 300 or 400 pages. If we think that, then it is only fitting that the container for those ideas is also something that the Stripe Press design team put a lot of time and care into. They're working just as hard to make sure the outside matches the inside. I also think that there's just a lot of ugly stuff in the world. It is your responsibility as a person to not add to the amount of ugly stuff in the world. **Jackson:** John has that amazing line about the world being a museum of passion projects, which is the other end of that. **Tamara:** That's right. **Jackson:** Everything around you doesn't happen arbitrarily; it happens because a few people really care. ## [00:24:16] Choosing Teachers and Authors **Jackson:** On this note of tacit knowledge, there's a lot of knowledge, even very practical knowledge, in the world that isn't written down. **Tamara:** Yeah. **Jackson:** But there's also a lot of things that aren't written down for good reason. How do you parse what types of things are worth codifying, especially the pragmatic, "here's how you do things" advice? In some cases, the books become the de facto guide on how you should think about scaling an organization or building a startup. There are high stakes in saying, "This is the go-to advice for how to do something." **Tamara:** That's right. The most important thing there is picking the right person to author that book. There are a lot of books out there already about scaling companies and people development. But one of the reasons Claire Hughes Johnson was such a great person to write \*Scaling People\* is that she is who a lot of people wish they had when they start a company. If you're a founder, you're focused on a couple of things: refining the product and acquiring customers. In the best-case scenario, if you're starting a company, things will go so well that you've got to hire. By the time you start having to hire people, it's probably too late. **Jackson:** The plane's in the air. **Tamara:** Exactly. **Tamara:** Claire is one of those people who thinks about these things fundamentally. She really loves people. She's the heart of Stripe. She has seen the dynamics of building and scaling an organization at two really important companies over the last 20 years. One was Google; she was at Google before it was even public. And then at Stripe, when it was fewer than 150 people. **Jackson:** That makes perfect sense. And yet there are also a lot of people who are effective who are bad at communicating their ideas. **Tamara:** This is true. It's something we struggle with when it comes to picking Turpentine people. This is the tacit knowledge where if A, but B, but if C, then D—and this is C. It's not always the same people who are great at doing and teaching. C Right? **Tamara:** Often people who are really good at a particular thing have no idea how to talk about it. **Jackson:** That generalizes from company stuff to the master craftsman. **Tamara:** Exactly. One of the constraints at Stripe Press—and we have a lot of them—is that we are not going to get anybody to write a Turpentine book who isn't a deep practitioner. 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 scale it, but it's just not an option for us. C Right. **Tamara:** 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. He has been on the cap tables of so many of the most important companies in the last 10 to 15 years. You don't acquire that kind of portfolio by accident. 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, as is really important right now, how to exit—whether that's going to be a merger, an acquisition, an acquihire, or going public. 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. ## [00:28:15] Charisma & delightfullness privilege **Jackson:** Another idea that anyone who's ever met you would agree you embody is something I'll 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? **Tamara:** How do you answer this without sounding like the most annoying person on the planet? **Jackson:** I'll tolerate it. Give us some theories. **Tamara:** I have some theories. The first is that I am a middle child. The plight of the middle child is that there's always somebody a little cuter than you and somebody who's been doing this longer than you. **Jackson:** It's brilliant. **Tamara:** So you have to stand out somehow. The plight of the middle child is that you have constraints. Constraints are great. **Jackson:** Constraints. Necessity is the mother of invention. **Tamara:** So true. My parents constrained me with this kid who's cuter than me and this guy who's been doing it longer than me. This probably started from a young age. Maybe that's the root of it. **Jackson:** You had to figure out how to get people's attention or get people to like you. **Tamara:** I've always been really curious, and the thing that I've always been most curious about is other people. I really love people. There could be a lot of reasons for this. Maybe one reason is that we share a religious background. There's a commandment to love people as yourself. That's just the commandment, but maybe part of getting lucky is making it easy for people to bless you. One of our good friends, Alicia, calls it flirting with the world. **Jackson:** Amazing. There's a notion around charisma that I really like, which is that it's much more about how you make other people feel. 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 that has less baggage. You've talked about 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 warmth, this dial of sun that's turned on. You can meet you once and get it, or at least get a seed of it. Can you talk a little bit more about delightfulness privilege? I think you're playing on pretty privilege for people who are underground. **Tamara:** This is not the same thing. I think what it is is that there's a ton of social infrastructure which seems totally unimportant, but is, in fact, everything. That means 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, or the way that you tend to react when you are hosting a party and somebody comes in that doesn't know anybody, and how you decide to integrate them or not. These kinds of things are 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 being given free things constantly, like free glasses of champagne. It happened four or five different times at different restaurants in different conditions. The question is, why does that happen? **Jackson:** Maybe you're just lucky. **Tamara:** Maybe we're just lucky? **Jackson:** I don't think so. **Tamara:** Maybe it's niceness. I find it hard to talk about this because I don't want someone's takeaway to be that this is how you interact with people to get stuff out of them. 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? **Jackson:** I worked at Chick-fil-A. **Tamara:** It's not quite the same thing, but I was a hostess and then a server for a little while. You know what it's like to have had a really long shift, a really long day. You're fighting with your partner, you've got a headache, and you have to keep waiting on people. It's 9:00 at night. 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 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?" 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. **Jackson:** That says a lot about society. **Tamara:** It happens infrequently, and Tammy is only one step away from Karen, so you don't know what's going to happen. Instead, I'd like to be able to say the name of the person that I'm going to be interacting with for two hours. What we're describing could be called niceness, but it becomes automatic. We have a lot of friends for whom something like this is true. These micro-interactions compound like anything else over time, and it produces a kind of effect that I would call luck. **Jackson:** I wonder if part of this is the notion that we've all just gotten cynical. "You want my name? What are you going to do with it? You're going to complain to my manager?" **Tamara:** Every micro-interaction you have with people feeds one perception of them or another. I'm not sure I have this, but a lot of people we know do. There's one version of charisma that's the cliché: They just light up a room. There's a subset of people who are able to capture and sustain attention wherever they go. Then there's another kind of person, and sometimes they're the same, who makes you feel like you are the only person in the room. It would be illegal for them to take their attention off of you. That's so powerful. Every time you have an experience like that, it's the most meaningful thing in the world. **Jackson:** No wonder those people end up being successful. Everyone who interacts with them feels important, special, and liked. **Tamara:** It's particularly impressive when you see this happen at a scale where they're the kind of person who, because they're so successful, is used to people deferring to them and being way more interested in them than they would receive reciprocally. You and I both know people who are quite successful. They're used to people deferring to them, but 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 talking about themselves. **Jackson:** It's a way of being versus this path to success. ## [00:34:59] Living a relational life **Tamara:** Some months ago, I read Virginia Woolf's essay on Montaigne. In part of the essay, she talks about the way that he lived his life, but she also starts talking about his orientation towards people, and by extension, hers. She considers it a social deformity if you're the kind of person who can't laugh easily with your neighbor or make conversation as easily with the banker as you can with the plumber. She sees this as a critical part of being a human being, which I tend to agree with. **Jackson:** I have that quote right here, and I wrote it down because it's the most distinctly Tammy thing I've ever read. This excerpt in particular 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 is it so important to live a relational life? **Tamara:** I don't think that you can live any other way and live healthily. We were joking about this the other day. We are friends, but we also have this 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. And it's really lovely because there's this interlocking web of people. That's really cool when you, Devin, Ann, 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 need your village around you. Or even better, when you're needed. It's one thing to 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." 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 this breakdown of community as understood this way—these thick connections. I feel really lucky that that's not the life that we live. That doesn't mean having 40 best friends, but just having a core of people that you can rely on, that rely on you, and that even expect things of you. And maybe my favorite person who writes about this is Ava. She has this very ambitious model of friendship. For example, she's constantly telling me that me not living in San Francisco—and you too, by the way—is ruining her life. You can actually demand that your friends live near you, and I love that. There are a lot of people who I think prefer to live a life that doesn't require them to have obligations to anyone. But when it really comes down to it, everybody wants to get the call. **Jackson:** 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-Rémy in 2023. It was springtime. And she told me she decided to be vulnerable with me starting now and that we were going to be close. I was a little bemused because she had not so far been particularly vulnerable at all. 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." **Tamara:** I love her so much. **Jackson:** There's something inside of this, though—and you might not like the words I'm going to use here—but there's a social agency, or at the very least, a willingness to impose your will on the world socially. It's that feeling of, "Hey, sorry, whether you like it or not, we're going to be friends now." And that also ties to something else you were saying: The obligation is the gift. Can you talk about what's inside of telling somebody, "Hey, we're going to be friends now"? **Tamara:** Honestly, I think that was a little obnoxious of me. We'd had enough interactions to that point. We had people in common who kept telling us individually, “You two would really like each other.” And I was ready to go all in. I think that we're going to be friends for 50, 60, 70 years, so we should just start now. We might as well start now. That doesn't work unless you have these repeated interactions. It means, for example, that every time you go to dinner, you're not going back and forth about how to split the bill. It's just, "You get it this time, I'll get it next time." And there's this reciprocity there. 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 kid, who couldn't have been more than 10, comes up to him and asks, "What would you do with one more day with Charlie?" He says, "I would probably spend it the way I spent every other day with Charlie." They were constantly in contact, even if they weren't in the same place. And he said to the young person, "If you find somebody like this, my suggestion to you is that you lock it down and you try to meet with them as often as possible." I guess that's my model of friendship. C Right. **Tamara:** I happen to live abnormally close to my village here in New York. And it's funny that when I go to San Francisco, there really is one square mile that most of my people live in. I don't know what's behind that. I also think part of it is cultural. I have a really big extended family, but I didn't grow up around a lot of them. But there is this expectation that you have a cousin in every city, or someone that's functionally a cousin. And that's really beautiful and really lucky. **Jackson:** How would you describe your taste in your friends? What types of qualities get somebody in? **Tamara:** What does get somebody in? I think this is the most important thing: we're not opting out of this friendship. You'll hear increasingly these days about friendships just going wrong or friendship breakups. I think nothing is harder than a friendship breakup. **Jackson:** It's like in \*The Banshees of Inisherin\*—a crazy friendship breakup. **Tamara:** And he just decides one day, "I just don't like him anymore." C Right. **Tamara:** It's a motif that's repeated, especially through the first part of the movie. "I just don't like him anymore." This idea is most important to me. We're not opting out. If we are close friends, we can go through as many ruptures and repairs as we need to. And paradoxically, it makes it less likely that you run into these arguments. This is the consistent orientation to all of our friends, because we share a lot of these people in common. You don't get to opt out of this friendship. We're doing this for 60 years. What does that actually mean practically? It 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. Eventually, when we're all married, we have this group orientation towards each other on some level, such that it even extends to how we date. C Right. **Tamara:** We don't all want to date partners who need to be all of our best friends. The idea is that if there's ever a day that I'm sick, and you and your wife needed something, I need him to go in my place, and vice versa. You would do the same thing. This changes every interaction because it means we don't need to be next to each other all the time, although we are in pretty regular contact. That will change as people have kids. A lot of my best friends in other cities, whether it's in D.C. or Dallas, already have families with two, three, or four kids. You see the same orientation. It's not a perfect one-to-one, but if I'm in D.C., there are three or four people that I have to see every time. Even if I go a year without talking to them, if I really needed something, they would be there, and vice versa. ## [00:44:07] Trust, social scaffolding, and small talk **Jackson:** brought up Charlie and Warren and this web of people. There's an idea that applies to friendship and professional relationships. You've described the real thing people should take away from Warren and Charlie—not 50 years of compounding—as "a seamless web of deserved trust." Can you describe that phrase? **Tamara:** It's not a phrase that originates with me; it originates with Charlie. There are all of these invisible, totally load-bearing structures that we don't appreciate. One of those is trust: the idea that I can interact with you without having to negotiate every single interaction. **Jackson:** A repeat iteration game. **Tamara:** Exactly. I can live my life and do business with this person or firm, and I don't have to constantly think about, "Is this person going to cheat me? Do they mean what they say when they say it?" This scales all the way up and down, to personal relationships and to entire societies. How easy is it to get things done? Do you think that most people can be trusted? The seamless web of deserved trust means being the kind of person who says what you mean and does what you say you're going to do. You're the kind of person that makes it easy for people to interact with you. Part of this delightfulness thing is: are you the kind of person that's easy to interact with? Are you predictable? **Jackson:** A different version of this, or maybe the other end of the spectrum: you used the frame "load-bearing." Another thing you've talked about that I admire in you is your appreciation of small talk. **Tamara:** I love small talk. **Jackson:** It's the exact opposite end. It has none of the weight of the friendship stuff we were just talking about, yet you've made the case that it's doing a lot of work in the background, too. **Tamara:** I'm small talk's strongest soldier. I will go to war for small talk. **Jackson:** Give us the case. **Tamara:** I totally buy a lot of the reasons that people dislike small talk. It's a waste of time, it's not going to get you anywhere, and I don't care what your favorite color is. **Jackson:** I would also add that a lot of people would hear what you just said about living a relational life—even being charismatic or flirting with the world—and agree. I suspect a large percentage of those same people, who otherwise put a lot of weight into relationships, think small talk sucks or doesn't matter. There's an interesting dichotomy there. **Tamara:** I hear that, and I understand that. I would argue that it's this invisible substrate that matters a ton. You can't build a skyscraper without a foundation. Let's take it in a couple of domains. In business, for example, I'm trying to do a deal here. I really don't care how your commute was on the way over. When people are employing small talk in business, I'm trying to see if you know how to read social cues. I'm trying to see 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. That's what I'm doing when I'm doing small talk in business. **Jackson:** That framing is almost like testing for something, but you're also trying to create ease. It's an invitation as much as it is a question. **Tamara:** I'm trying to find points of compatibility. You're trying to find these leverage points by which you can go deeper. One of the things I struggled with early on in my time in SF was this real habit that people had of saying, "I don't want small talk; I want big talk. I need to know what happened to you at 17 that explains why you are the way that you are." And it's like, hold on, we don't know each other. **Jackson:** We're at a house party. **Tamara:** Or you're on a first date. **Jackson:** I'm guilty of this. **Tamara:** Maybe I don't care what your favorite color is, but you can't build a relationship that lasts decades without establishing this basic social trust. **Jackson:** Proximity is another form of this. A sign of a really great friendship is not that you can sit and have a super deep two-hour conversation. It's that you can be perfectly comfortable in silence for five hours driving or shopping for groceries. It's both of those things. **Tamara:** When a friend of mine, Caleb Watney, and his wife Katerina Watney got married, for some portion of their relationship it was long distance. One of the things I referred to was Tyler Cowen's guide to long-distance dating. He says that instead of trying to make every time you're together a unique, distinct experience, you should do a lot of mundane stuff. What is marriage if not eating dinner together every night? Do I think I could eat dinner with this person for a long time? **Jackson:** Give me the most boring environment setup possible and am I still engaged? **Tamara:** Does it still work? There's a societal layer to small talk that matters a lot. America has a lot of heterogeneity in the population, which means that things like small talk are this important social ritual that maybe Europe doesn't need because there's a lot more homogeneity in an individual population. **Tamara:** Small talk is how you establish, between people who have very different cultural contexts and are coming from a different place, that— **Jackson:** We're on the same social kindling. **Tamara:** We're on the same team. It offers you a lot of low-stakes, repeatable interactions. Where I'm from, the South is famous for this level of hospitality. **Jackson:** Inside of this is also manners, politeness, and etiquette. They're all in this bucket. It seems that people are asking, "Do we really need these?" It's like a Chesterton's fence. **Tamara:** It's only when it's gone that you realize that the thing which seems pointless and silly is load-bearing. Some people may listen to this and say I'm overthinking it, which I'm fine with. But it does seem pretty important. ## [00:51:01] Erosion of social norms, low-trust environments, and load bearing infrastructure **Jackson:** your frame on this is the notion that we're all so desperate for community, and yet we don't want any of the obligations that go with it. This applies to friendship, too. It feels very heavy in today's era. It's, "I want relationships and I want community, and I also want to do it on exactly my terms, with exactly what I want." **Tamara:** In the least restrictive way that asks as little of me as possible. There's a flip side to what we're talking about. When you have these shared social scripts and they start to break down and not be universal values, you see people wanting to curate their own environments. **Tamara:** One of the things I am interested in is the rise of private security. I used to work on charter cities, and when you go to places like South Africa, Zambia, or my home country, Nigeria, you'll see that you live in the country, but you actually live in your enclave. This is a part that you've been able to curate. 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. You don't want to interact with everybody in the population because it's not a high-trust population. In low-trust areas, people stay in their clans. As it becomes higher trust, you can trust more different kinds of people and interact with more strangers. You don't see this in places with a lot of low trust. I'm particularly interested in the rise of private security in the US because you can't necessarily trust that we're all following the same social scripts. This also includes the reintroduction of things like members' clubs, or existing members' clubs becoming a tier more exclusive because you have people who would rather not interact with the median person. I think that this is unfortunate, but this is what happens when you lose these social scripts. **Tamara:** A month or two ago, you saw the fuss over the Uber bus. It's like Uber carpooling. **Jackson:** It's the airport shuttle. **Tamara:** It's not the airport shuttle. I think they're actually testing a regular bus. **Jackson:** Uber invented the bus. **Tamara:** Congrats, you invented a bus. But what a lot of people were quick to point out was this isn't really a bus. This is a way that I can pay a little bit more to not have to deal with the dysfunction that comes with riding the subway. If riding the subway was a perfectly pleasant experience where I don't ever have to come into contact with people acting crazy, then you don't need things like a bus. **Jackson:** The extreme version of this is the culture of LA, where you never walk or take public transit. The implicit thing there is that I never have to interact with another person that I don't choose to. When that is the fabric of society… **Tamara:** It's not great. **Jackson:** This is a great lead-in to the next thing I want to talk about. You use the phrase "load-bearing" a couple of times, and you've thought about this a lot in the context of societies. In healthy societies, I suspect there's a scaffolding that allows us to move freely and safely—a hidden infrastructure. Can you talk about what is embodied in that ability to move freely and what you mean by that? We'll talk about the implications on both the social and security sides. **Tamara:** Do the social conditions wherever you live make it easier or harder for you to go about your day as normal, to live your life? You and I have talked about this before, but what we're discovering—at least if you let Twitter tell it—is this mass rediscovery of why shared social scripts matter so much. **Jackson:** Another Chesterton's fence. **Tamara:** It's not just politeness. It turns out that we don't all agree on why you shouldn't take loud phone calls in public. When you're going out to eat, why not just take turns paying instead of negotiating back and forth about who's going to pay? In the first example, shared spaces require shared consideration. With the second, reciprocity is the foundation of having relationships that scale over time. You don't want to live in a place where you have to negotiate every single thing about your day. **Jackson:** That is the lack of ability to move safely and freely through the scaffolding. **Tamara:** Exactly. 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. When you don't have social trust, there are entire parts of your environment that just become off-limits to you. It's really unfortunate for the people in your population that are already pretty vulnerable—for example, kids. We talk a lot about why kids can't move freely anymore and the loss of mobility that children in many countries have enjoyed. But there are still countries in which... **Jackson:** You see kids wandering around Japan. It's crazy. **Tamara:** There's that whole show, \*Old Enough!\*. The point of the show is that a two-year-old can operate functionally in your city, and a parent would let them. The youngest kid on that show was two years old—he was probably almost three—running an errand. The thing you worry about the most is, is he going to remember the grocery list? That's unheard of here. C Right. **Tamara:** And in the first episode... **Jackson:** Not that I sent my two-year-old. **Tamara:** But will he remember the grocery list? **Jackson:** There are so many ways we could take this. One thing I like a lot about how you think about it is COVID being this forcing function for some of these things. 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 face the Chesterton's Fence of them. A classic example is, why does etiquette actually matter? An example you brought up that sticks in my head is: why do you not take your wine bottle home with you if no one opens it at the dinner party? These types of little things. Can you elaborate on that? **Tamara:** I don't know that there's much to elaborate on. **Jackson:** You brought up the speakers as another one, or greeting someone in retail. Talk about why some of those things are load-bearing. **Tamara:** It's these shared scripts that make it easy for a stranger to interact with you. Without that, you don't have anything else. C Right. **Tamara:** There is often an over-emphasis on the obvious things you can see in any social situation or in governing. C Right. **Tamara:** And what we miss is that you can basically only operate at the level of effectiveness of the least effective part of your society. C Right. **Jackson:** It's like a minimum viable threshold. **Tamara:** Exactly. We were just in Montecito with a mentor and friend of ours, and we decided as our gift that we were going to get him books. We were going to sign them and tell him why we got him the book. 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. Of course, Montecito is not your median town in America in any meaningful sense. It is a total enclave. **Jackson:** Idyllic. **Tamara:** But there are places that aren't nearly as wealthy that still enjoy this level of social trust. The church that I went to growing up is not in the best part of Dallas; it's near lots of apartments. But often the doors to the church are open. They're unlocked. **Jackson:** Yes, this is captured. C Right. **Tamara:** Anyway, back to Montecito. I went to this bookstore, and I didn't bring my wallet with me. I forgot to. **Jackson:** You're in Montecito. These things are taken care of. **Tamara:** You just think you can use Apple Pay anywhere. **Jackson:** Sure. **Tamara:** In this particular store, I couldn't use Apple Pay. I picked out a couple of books that I really wanted to get, and I was thinking they don't take Apple Pay. They don't have tap-to-pay, so it's over for me. The store owner said, "No, that's fine. Take the books. When you get back to New York, just send me a check." I asked, "What?" He said, "Yeah, just send me a check. It's fine." He really wasn't trying to argue with me. He said it as though it were the most natural thing in the world. **Jackson:** There's an abundance in that, rather than scarcity. **Tamara:** Because in his world, in his daily context, everybody can be trusted. If you're in Switzerland, their public transit system handles at least 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 because you're behind some person who's new... **Jackson:** Some person who's new. **Tamara:** A tourist who doesn't know how to use it. In Switzerland, you just walk straight on because the assumption is that the population is going to pay. **Tamara:** Instead, what happens is you get random ticket checks, and if you're found… **Jackson:** Oh, you just pay on your phone? There are no gates? **Tamara:** Exactly. You just walk straight on. **Jackson:** Wow. **Tamara:** The assumption is you've already paid. If you're found to have not paid—to be fare evading—you get a fine of about 100 Swiss francs. **Tamara:** There's a lot baked into that scheme: the assumption that most people will pay. Interestingly, they've seen fare evasion rates increase about 50% in the last couple of years, since around 2018. One of the countries that borders Switzerland is Germany, and another is France. They think on the French side of the border, you're getting a lot more people coming from France, where there's a less strong norm about paying. They think that's what's happening, so there's some debate about what to do about this. ## [01:02:17] Cultural arson and the dark sides of "you can just do things" **Jackson:** Implied in all of this are norms and staying above the tragedy of the commons. 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? **Tamara:** I call many more things cultural arson than my friends would. Let's take an example. A couple of months ago, there was a scissor statement that happened. **Jackson:** A scissor statement is a reference to a Scott Alexander blog post that everyone should read. The essence of it is like "the dress"—the blue and white one or the black and gold one. It's a situation where it's obvious to everyone that the answer is yes or no, and no one can understand how anyone could believe the opposite. **Tamara:** Thank you for that. **Jackson:** Had to mansplain a little bit. **Tamara:** This originated, as so many annoying things do, in tech Twitter—or maybe it was rationalist Twitter; there's some overlap. A guy is recounting a story of being out with his girlfriend on a very cold day. He tells his girlfriend, "I'm cold." And she does what he thinks is the highest-agency thing. **Jackson:** You can just do things. **Tamara:** Exactly. You can just do things. So what does she do? She goes to the first hotel that they pass and tells them that she's just stayed at the hotel and has forgotten her scarf. This is some European country, so they end up pulling out the scarves, and she takes the nicest one. She gives it to her boyfriend, and he's no longer cold. He tweets this, and I think this is an innocent story. I don't think that this guy is a bad guy, but he probably expected the overall reaction to be positive. C Right. **Tamara:** Your girlfriend is so high agency. I wish I had a girlfriend. **Jackson:** Like anyone would do. C Right. **Tamara:** No, I actually wouldn't do something like that. The only reason 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. There is a real lack of appreciation for... **Jackson:** And by the way, the person who lost the scarf actually now won't get it. **Tamara:** You don't know how long it's been there. Maybe it's been there for months, in which case, fine. But you don't know that when you're choosing to tell a lie about needing a scarf. It's fine if one person did that, but if everybody did that? There's a very tortured logic that a lot of young people employ towards shoplifting these days. C Right. **Tamara:** The idea is, "I wouldn't shoplift from a mom-and-pop..." **Jackson:** "...shop, but Amazon..." **Tamara:** Whatever. **Jackson:** Or Walmart, Target. **Tamara:** And today, it takes me forever to get some freaking toothpaste. It's not necessarily because of young people. C Right. **Tamara:** Nobody thinks when they decide to fare-evade, or take a scarf that doesn't really belong to them, or steal something, that it could cause a ripple effect. **Jackson:** It's like a paper cut. **Tamara:** That's right. It's like death by a thousand cuts. No one person acting this way is going to ruin the experience. But if everybody acted that way... This is the genius of broken windows theory, which has been empirically borne out. in a neighborhood and a window breaks and you don't fix it, you can expect that in due time, every window in the neighborhood is going to be broken. **Jackson:** Wow. **Tamara:** He also has this phrase called "defining deviancy downwards," where you slowly lower the standards of behavior. The lowest common denominator slowly gets worse over time. You see this borne out in so many places. If you're at a concert and one person thinks it's okay to throw something at the performer, you're starting to see this way more often. People are throwing things that are hitting performers—throwing people's cell phones at them, and it's hitting people in the face. If you let even a little bit of these things slide, you end up with an environment that's just worse. It raises the opportunity cost of being in public. C Right. **Jackson:** How would you describe this to people? For the most part, American listeners probably take for granted the way we are able to move socially through our scaffolding freely. How would you challenge people or illustrate this? You brought up South Africa briefly. You once told me South Africa looks a lot like LA, and yet... **Tamara:** In certain places, anyway. The first time I visited South Africa, I was in Johannesburg and specifically Sandton, which is one of the wealthiest parts, if not the wealthiest part, of Johannesburg. It's also the business district. From your hotel, you look out and you see Deloitte over there, the Radisson Blu over there, and the Hilton South Africa over there. The first time I went, I tweeted a picture of Sandton and asked, "Where do you think I am?" The responses I got were Los Angeles or Tyson's Corner, Virginia, which was not a horrible guess if you've ever been to Tyson's Corner, Virginia. If anyone had been paying attention to the lights, they would have seen I wasn't in America. But the very first thing I was told by the people we were with, in broad daylight, was to never have your phone out. Last week in London, I was going for a walk with my manager, Sam Bowman, and he said the same thing to me. We were talking about London, not South Africa. He knows people who've had their phone stolen from them. One of the ways people will do this is by being on a motorbike. **Jackson:** I watched a guy do this in London. He just ripped it out of somebody's hand. **Tamara:** That's insane. **Jackson:** Yeah. **Tamara:** For people who can't imagine this, every decision that you make becomes more frictionful. You can never just turn your brain off and exist. My sister did a study abroad for a summer in Spain. She was in both Seville and then also in Barcelona. She would call me at 3:00 a.m. her time, just walking alone through the streets to get back home because Spanish people are up all night. And I would be like, what the hell are you doing? Because there's no chance that I'm going to be walking around at 3:00 a.m., generally speaking. But she is in an environment that has the social infrastructure to support a single young woman walking around without having to be particularly vigilant. Now, of course, there is some level of vigilance, but the idea that you could just be on your phone, not really paying attention because you know the way home, and get home safely—this is what I want for everybody. Until you are in an environment where you do have to think about every single piece of your environment, it doesn't really click. It's unfortunate because in the West, and specifically in America, people won't really appreciate it until we get there. They go to CVS and all of a sudden every single thing they need is locked up. **Jackson:** Or better yet, the Walgreens has the glass broken in, as was the case for parts of San Francisco for a little while. **Tamara:** San Francisco is getting better, but they finally got a Whole Foods, and the Whole Foods shut down a year later because they couldn't stop people from loitering and using it as a public bathroom. There was also just way too much theft. A lot of times people will laugh at this. 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 people who would excuse this kind of behavior than I do for the antisocial person who just lacks impulse control for whatever reason. **Jackson:** Or just had an emergency. Every incremental action of this type can be justified, sort of. **Tamara:** You can go to the end of the earth and hear people say, "Poverty is the reason why I need to steal dozens of whatevers from CVS." It's the tyranny of root causes. You can make any excuse in the world. People say this about fare evasion, but in most cities, the people evading fares are not the poorest people. Most cities have programs that allow low-income people to ride for free or at very reduced rates. Sometimes in society, there's an overemphasis on the extremely visible parts of disorder and a lack of appreciation for the little cultural cracks that eventually lead to major problems. I know the CVS example is insane, but five years ago, you could go to any CVS and get anything you needed. **Jackson:** What's inside of all of this? You've described a case against mercy, which sounds very extreme. **Tamara:** That's the name of a piece I'm currently writing for Works in Progress. **Jackson:** Wow. **Tamara:** So we can't linger here for too much longer because you have to read the piece. **Jackson:** What I think I'm hearing is that we've talked about examples here of soft scaffolding and hard scaffolding. Soft scaffolding is more about social things and norms. Hard scaffolding is about whether I can walk around this city safely without being mugged. What you're pointing at is this notion that it's a continuous gradient. The soft things eventually give way, breaking the dam by a thousand cuts and making the hard things possible. **Tamara:** Exactly. I tend to focus on the substrate—the stuff that isn't obvious, because that's the load-bearing stuff you don't expect. A live conversation in tech right now is about norms. There are things relating to acqui-hires, acquisitions, and what employees owe their employers. There are entire companies that, as they currently exist, contribute to an environment that makes tech more low-trust and makes people more suspicious of each other. Even if that's not what the technology actually does, what does it mean when you brand something as cheating technology? There's this argument that there's already rot, so all I'm doing is exposing the rot. **Jackson:** Or better yet, that's high agency. You can just do things. **Tamara:** It's high agency. But making things worse doesn't make them better; it just makes things worse. The way to make things better is to make them better. That sounds like a tautology, but this is basic stuff. I find it both heartening and disheartening to see a lot of people I appreciate saying, "I really don't like that. I don't want us to become the kind of place that rewards what I think is cultural arson." We have lost the ability to distinguish. Some people use in ways that I think are just bad. Even though there are a lot of cultural consensuses that no longer hold, "cheating is bad" is one that I think still holds. **Jackson:** But will it in ten years or five years? **Tamara:** It certainly won't if we all reward that—or not even reward it. **Jackson:** Rewarding it is another step. It's almost just, "Ah, it's fine." **Tamara:** What you've seen is a lot of people who we admire, who you can see are doing bits. You interact with them in real life and they are not saying the insane stuff that they say online. It's so clear that they've been either audience captured or something has broken in their model of the world, in their brain. **Jackson:** I think it doesn't matter. **Tamara:** There's this fundamental nihilism. I'm just saying things. I'm in the arena saying ## [01:15:44] The healthy kind of agency **Jackson:** I love your commentary on agency. It is so captured by the "you can just do things" thing. There are two ways to internalize that. The first is that the world is plastic. You can experience the world as happening to you, or you can experience it as asserting yourself on the world. That is so powerful. Arguably, there's nothing more important to teach. That is so important. And yet, there's also a version of this "you can just do things" agency that you're pointing out, which is that you can just take what you want. That is not the same thing and not necessarily good. **Tamara:** It's certainly not the way I would advise young people to go about entering this industry. I think tech in particular—whatever a lot of people want to say about it, however people want to criticize 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. **Jackson:** This goes back to scarcity and abundance. One of those definitions of agency is abundant, and the other is scarce. That is so important. **Tamara:** In a lot of different places, positive sums are baked in. One of the biggest places that exists is in employee equity. **Tamara:** You're getting a share in this company. It's common that people are constantly doing favors for each other, and 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. You end up with a dynamic that's rather like Scorsese and De Niro, where you have investors and founders that tend to work with each other again and again. Of course, you build networks, and that's a really great, valuable thing. 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 to develop an internal locus of control and an appreciation for cause and effect. Not to belabor the point, but I do think there is a cultural script that really wants young people—and some young people in particular. I'm a Black woman. I can be no other. I've been a Black woman for 29 years. Some of the advice that I got, even 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 have to work twice as hard to get half as much. I'm not saying that those dynamics don't exist, and I've seen it in my own life. But the practical effect of internalizing messages like that is that you shouldn't even 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. **Tamara:** but You should be an actor, an active participant in your own life. Maybe think of yourself as a main character. There are all sorts of ways in which the world is malleable, and there are invisible rules that exist on paper but don't really exist. You can cold email anyone. A couple of months ago, Dwarkesh interviewed Satya at Microsoft. The way that he did that—I'm thinking he had a strategy—he literally just emailed him. He had done some work beforehand to say, "These are the kinds of questions that I would ask you." I'm not saying I could get Satya tomorrow, but maybe I could. Maybe I could. I think it's so healthy, especially from a young age. Someone that we both love is Simon Sarris. He's written a lot about developing agency, especially in your children, and instilling it in them. I agree with him on this. There is this innate desire in humans to want to be useful, and you see this in very young children. I've stayed with him and Semi for a weekend. At the time, they just had Luca; they now have three kids. Even then, Luca was two or three at the time, and he was doing chores. He has internalized this idea that if he wants something, he can go make it or get it. He can go get an egg from the chickens. 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 meet the world absolutely out of abundance, which is one of those words right now. **Jackson:** That ## [01:20:45] Tammy's N of 1 path and who she aspires to rhyme with **Jackson:** 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 the things she brought up was that you have a very N of one 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" excerpt. You have some threads from other friends. He says, "Interesting paths are not repeatable, but they rhyme." Who are you aspiring to rhyme with? **Tamara:** Who am I aspiring to rhyme with? It's some combination of Anna Wintour, Pamela Harriman, and Esther Cooper Smith. **Jackson:** I don't know the last two. **Tamara:** So, who are Pamela Harriman and Esther? **Jackson:** Who is Anna Wintour, while we're at it? **Tamara:** Anna is the outgoing, soon-to-be-former Editor-in-Chief of Vogue and a total force of nature. One of the things that's really interesting about her is that she was the image-maker for so many people. If you're a female politician struggling with likability, you go to Anna. If you're an athlete leaving sports to pivot into doing a beauty brand, you go to Anna. If you're a new celebrity in the middle of awards season and you're hoping to get your name and your face in front of the most important people, you want to be in Vogue. There's this cultural capital that Vogue has. People want to say that it's declining, and I do think it's declining. **Jackson:** Right. **Tamara:** 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 is Vogue's first 2020 issue. They called it the motherhood issue, and they had four different covers with celebrities like Cardi B, Ashley Graham, and Stella McCartney. The whole idea is that for so long, women were expected to compartmentalize the things that they do. You are a mom here, and here you are superwoman. But in fact, for many women, being mothers has unlocked a lot of their own creativity. Stella McCartney says it has made her think in really careful ways about the clothes that she's making. Cardi B says she always wanted to be a young mom. A lot of people said when she had a baby that she would be ruining her career. Well, here we are. Her daughter just turned seven, and Cardi B hasn't gone anywhere, although we are waiting for the sophomore album. And where are we today? Now we're all talking about fertility and the 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. **Jackson:** The Twitter history is always there. **Tamara:** Anna was the cultural curator. Nowhere is that more clear than at the Met Gala. There's a ton of people who will say they don't care about that or have never heard of it. To that I say, there are a lot of people who don't watch the Super Bowl. Those of us with taste like both. Esther Cooper Smith is really interesting. She is an archetype of woman that I think is underrated. She was a socialite in D.C. and a huge donor, mostly to Democratic causes, but her real value was as a hostess. Just like with Anna, Esther is who you went to to remove the friction in some literal geopolitical conflict. 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. **Jackson:** Wow. **Tamara:** She was such a trusted, great host, and the art of hosting is something that is lost on a lot of people. It's one part curation, but it's also one part knowing how to invite people into a space and invite them to open up in ways they wouldn't necessarily, maybe even one-on-one. Beyond that is the power of that kind of social grace and social intelligence. It's interesting to me that I'm seizing on both fashion, Vogue, and hosting, because for a long time these have been uniquely female sources of power. They are ways to accrue influence that don't require you to have beaten sexism. **Jackson:** have totally embodied a much more masculine Most of the best historical examples of women succeeding in other areas of business are because they down-leveled their femininity in some ways. **Tamara:** These are areas in which your femininity is a total asset. A lot of people devalue things like this. **Jackson:** Partly because they're more illegible. **Tamara:** Exactly. I'm not a royal family watcher, but people often say about Queen Camilla that she is the person 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 you are the only person in the world for the entirety of that dinner. These are forms of social leverage that are really enchanting to me because they don't require you to brute-force anything. If I want my path to rhyme with anything, it's far more of that than anything else. The third person you mentioned, Pamela Harriman, is interesting. There used to be this kind of transatlantic person who had cultivated a social scene both here and in the UK. Of course, this is very class-based. There are some really dramatic examples of this with the dollar princesses—the American women with fortunes who married into UK titles because they each had what the other wanted. You have the most famous example with Consuelo Vanderbilt, but there were all sorts of people who used to exist on both sides of the Atlantic. They were really fierce individuals who had a lot of—in Pamela's case—not just social influence, but political influence. 27:19 Right. 01:27:20 She was a close confidant of Winston Churchill. Not that I want to be a close confidant of any specific president, but there are these quiet ways to influence things, maybe more enchanting than having to take tons of power. **Jackson:** 01:27:44 ## [01:28:38] Red herrings of success and focusing on outcomes **Jackson:** Also in that advice essay, you say to avoid chasing the red herrings of success. was about a year ago, and I'm curious how you reflect on that a year later. It's especially relevant because you work in media and in the land of ideas and narratives. I've been reflecting on this a lot as I make more media, and I wonder to what extent media, ideas, and narratives could be those red herrings. How do you think about inputs and outputs more broadly? **Tamara:** 01:28:25 How do you know that the stuff you do matters? **Jackson:** 01:28:30 Of course, you're never going to know. But there's a meta-question about the… **Tamara:** 01:28:35 The metrics by which you judge yourself. 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\* or \*High Growth Handbook\*, I'm hearing from founders, executives, and engineers. One of our bestselling books is \*An Elegant Puzzle\*, which is all about engineering management. That seems like such a niche field, but it is one of our bestselling books. I care way more about whether the people who are working in these particular industries and disciplines find it useful. The whole point of Turpentine is that it's actually supposed to be useful and fundamental in some important way. Nobody is born knowing how to be an engineering manager, and it's always the best when I hear from people directly. We do these pop-ups now where we'll just show up in a city and have a one-day coffee shop. Inevitably, I get into dozens of conversations about how a particular book helped them set up their company or helped them run it. A lot of Claire's time right now is spent speaking to companies that are already huge, because her particular philosophy when it comes to running an organization is actually quite novel. It's not one weird trick for management or inundating you with a million examples that are impossible to generalize, but instead a principles-based framework for all sorts of things, like hiring and whatnot. That, to me, is the metric. When it comes to Turpentine, it's hard to know if you're moving the culture in a particular direction. But that is hopefully the metric. Another one is something I say in the "Advice to a Young Person" piece: You unwittingly end up creating an announcement economy. You're constantly announcing the intention to do things, and it turns out you can get just as much praise, money, and all sorts of good things by announcing an intention to build something as you can by actually building it. We're in this time of incredibly glossy pre-launch videos. I was talking to Lulu Meservey the other day, and she actually took the other side of this argument. Part of what you're trying to do when you launch a really glossy video first, even if the product hasn't quite caught up to the capabilities, is to demoralize the competition. You want to make it harder for people to think it's worth working on what the competitor is doing. **Jackson:** 01:31:15 Right. And you're also trying to aim for the moon and hit the stars. **Tamara:** 01:31:19 Right. **Tamara:** I tend to think that it actually just amounts to overpromising, and maybe sometimes you never actually get there. ## [01:32:22] Assortive everything **Jackson:** There's another part of your path that you have described as a sort of everything, or maybe it applies beyond just your path. You've used framings like, "I'll end up there" or "the right people will get there." Another thread of this that I feel is important is the notion that friction in certain contexts is good. Can you talk about what that all means? **Tamara:** I certainly don't mean to imply that friction everywhere is good. There is plenty of friction that keeps people out. Part of the reason Stripe Press exists is because it's way too difficult, even if you're in San Francisco, to get a meeting with the likes of a lot, Claire, Will Larson, and so on. It's that much more difficult if you're anywhere else in the world. **Jackson:** Right. **Tamara:** I have an appreciation for friction, but in some places, having some friction actually ends up meaning that whoever ends up in that thing is high signal. There's a lot that we can take from that fact. Let's just take YC. There's a lot that we can take from the fact that Paystack and Stripe ended up in YC coming from very different places. **Jackson:** Right. **Tamara:** You actually do want some friction. To take a different example, a friend of mine, Maren, founded a technology fellowship called Interact. It's a fellowship for young people, and not just aspiring technologists. Increasingly, we have a lot of people who are interested in taking a much more academic lens to technology, so it's a really interesting multidisciplinary community. But either way, it's a fellowship for people who are 18 to 24. One of the most important features about Interact is that Maren does not advertise it anywhere. **Jackson:** I've never been a part of it, but I've met a lot of people in it. There's something about you guys that isn't super legible and probably wouldn't be the case if it were as well-known as YC. **Tamara:** That's right. It's so interesting because if I hear that the person who's in front of me is an Interactor, it just tells me a bunch of things about them off the bat. **Jackson:** Right. **Tamara:** What's particularly interesting about Interact 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. **Jackson:** Right. **Tamara:** At some point, we let in the first international student, and then it kind of just goes from there. It's not like when I was 18 to 24, I would have recommended every single friend of mine do Interact. But again, there is some useful friction. I'm not sure that you would get a better crop of Interactors if, instead of being primarily word-of-mouth-based, you were to plaster signs about Interact everywhere. **Jackson:** Or do performance marketing to make sure you're the most targeted. **Tamara:** Exactly. For some period of time, I think Stripe Press was like that as well. There have been requests for us to do media about it—to talk about why we are doing this. This is a question everyone always asks: "Why does a technology company have a press?" But maybe you don't need to explain it. Also, with my path to Stripe Press, there was no particular reason I should have stumbled into it, being somebody who's focused on charter cities in D.C. But it just so happened that a year before discovering \*Stubborn Attachments\*, I'd worked at Mercatus with Tyler Cowen. It is interesting to me that oftentimes communities end up forming in the right way, and you don't need to necessarily— **Jackson:** Go super emergent, or the dots connect in reverse. **Tamara:** The dots connect. You can brute force your way into assortativeness. One way to do this is by turning yourself into a door-to-door salesman. You can actually send a thousand cold emails. But a far more interesting place to find yourself can be found if you decide to instead be a billboard, whether it's by tweeting or by your blog. Writing online is still incredibly underrated. You put out these signals to the world: These are the things I'm interested in. These are the questions I'm asking myself. If you want to inquire together, make it easy for people to reach out to you. **Jackson:** It's like working smarter rather than harder. Sending a thousand cold emails is very respectable, but there is a version of it that is more specific or more... **Tamara:** Nuanced. And also driven by the things you actually care about. You might find that after sending your 567th email, you find yourself in front of Fortune 500 CEO number six. But that doesn't mean they have anything in particular to teach you. It doesn't mean they're not brilliant. But that's often far less useful than doing some work to figure out what you're interested in. Following your own curiosity is pretty underrated. ## [01:37:52] Personal and professional standards **Jackson:** We've talked about dignity, self-respect, and doing a great job regardless of how crummy the job might be. Another way to frame all of that would be standards. There's an amazing quote from an interview that you gave about the time you got to spend with Charlie Munger. You said that what you got from talking to him was the idea that how you do business and the standards you hold yourself to are so much more important than what's easily measured. He wasn't happy to 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? **Tamara:** Ultimately, what you want to create is what Charlie described so perfectly: a 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 increasing amounts of work. So how do you set yourself up for that? One of the big things is never compromising the quality of the book. That has to be paramount. 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. **Jackson:** In jobs like this—and investing is similar—it's hard to not feel like you got to be busy. **Tamara:** You get desperate. Or something else that happens, and I'm sure you've had this where people have pitched themselves for your podcast. We've gotten inbound from really big names, which, if we had chosen to publish them, would have led to instant bestsellers—books from big names that you know, or people coming from companies that you absolutely know are very important. It's worth it to us not to compromise 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 for the kinds of people we are talking to to internalize. That's the bar. **Jackson:** The stakes are high. **Tamara:** The stakes are pretty high because 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 building on the past catalog or taking us in a new direction we're excited about. It's never about compromising the quality of the book. Number two is being delightful and easy to work with. There was probably a time where I was a bit of an enfant terrible. **Jackson:** Many such cases. **Tamara:** I was once given feedback, maybe multiple times, about getting really emotionally invested in things. For example, everybody on my team used to know if I was having a good day or a bad day. I got this feedback from two different managers, and I really struggled to hear it because it felt like too much pressure on me. But the feedback was that a lot of the team feels how I feel. I have a disproportionate impact on the mood. So if I'm excited about something, we're all excited with me. But if I'm doubting something, if I'm down on it, or if I'm just in a bad mood that day, that affects how other people feel. That's 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. What I've tried to do is make myself a really predictable person to interact with. **Jackson:** Right. **Tamara:** I might be having a good day or a bad day, but you shouldn't be able to tell. It’s about being delightful to work with. Finally, there is this piece of not cutting corners—not just in selecting the books, but in general. There have been several opportunities, even this year, where we could have just gone with a cover and that would have made our lives easier. **Jackson:** Right. **Tamara:** We have two books this year that are coming out later than we planned because we weren't happy with the covers that we had picked. But again, how you do one thing is how you do everything. 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 internalize the idea that we're not going to let this go. That means there is a trade-off between speed and execution. ## [01:43:06] Journaling, great writing, and audience **Jackson:** The first book you worked on at Stripe Press was the republishing of \*The Making of Prince of Persia\*. I read a good chunk of it recently, and it's an 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. You've journaled for at least eight years. Aside from being the fodder for the Tammy Winter book someday, what keeps you journaling? **Tamara:** One of the things I tend to do, which I realized was not super productive, is purely verbal processing. **Jackson:** Yeah. **Tamara:** For me, there is nothing better than having the same conversation, just riffing about the same thing eight different times. I will call Alicia, then Sab, then you, then Ava, and just have the same conversation again and again. I get joy from that. **Jackson:** And you find new things, too. **Tamara:** You do find new things, but it ends up being on some level unproductive. But again, that's maybe some of that social substrate that really matters. On the other hand, it's nice to have a contemporary record of just how things are going. It's like a temperature check. For me, it does a couple of things. One, it is a way to process things and make progress on whatever it is that doesn't rely on me having to have somebody else there. **Tamara:** We haven't talked about this at all in this conversation, but you and I are both Enneagram Sevens. I know there are a lot of people who think it's one step up from astrology, but to the extent that you think it's real, one of the characteristics of a Seven is… **Jackson:** Inputs to realness, at the very least. **Tamara:** They're inputs to realness. One of the characteristics of a Seven is that the hardest thing for them to do is to sit in silence and to self-reflect. There are things about themselves or their own experience that they are scared of. There is a balance to be drawn between completely lacking self-reflection and therefore self-awareness, and navel-gazing. But I found it useful to process things by writing about them. **Tamara:** What's really interesting is that I'll go back and look at things after the fact. When there are really negative memories, when something bad happened, it's a way to get through it more quickly because you're able to name it and identify it. 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. It’s day after day of being in this incredibly low mood or state, and it's really hard to read. But human memory is an incredible thing because eventually you forget that stuff. **Tamara:** Thank God we forget. We could go on a whole tangent about why ChatGPT's memory function is so frustrating to me. **Jackson:** But we'll save it next time. **Tamara:** On the other hand, it's also really lovely to have a record for me of these wonderful people who float in and sometimes out of your life. There's always a really fun thing where the first time somebody appears in my journal, I find that really interesting. I find it interesting when people make it into multiple journals. You are definitely in my journal somewhere. It's a record of people that I love, which I also think is great. We were just in Montecito, there's a week's worth of reflections about why that week was both a catalyst and a retreat and a sanctuary. **Jackson:** By the way, we are unreliable narrators. You're an unreliable narrator when you're journaling, but that's a different cut on it than the memory of the memory you have. I found it's a really great way to stay in touch with my past self and maybe even my future self, acknowledging that we're all just subjectively experiencing this version of it. **Tamara:** It's so funny what goes into what we choose to remember and what we choose not to remember. To your point about keeping in touch with your past self and your future self, maybe it makes me more attuned to the present moment. I'm prone to daydreaming and to thinking very far into the future or ruminating on something in the past. In the same way that a gratitude journal makes you much more likely to look for things to be thankful for throughout your day, this journal is also keeping me more attuned to the present moment. **Jackson:** We've talked a lot about the content of writing and the books that you publish. From a more stylistic standpoint, what actually makes for good writing? **Tamara:** I'll focus on the domain I know best: nonfiction. The best writing is first and foremost clear. To effectively communicate something, I have to know what you're saying. This often goes wrong when people read just enough to grok a particular writer's style and try to copy it. The writing becomes less interesting, or they use more complicated terms than necessary to explain something simple. The prose becomes overloaded because they think that's what makes for good writing. But the best writing, especially nonfiction, is fundamentally clear. **Jackson:** It's in service of something. Too much of the writing can get in the way of explaining or teaching. **Tamara:** Or storytelling. **Tamara:** Second, a lot of the best writers have somebody in particular in mind, so they're not writing to the void. Sometimes that person is themselves. Brian Potter is a great example. When he's writing, he's answering a question that he has, and you get to come along for the ride. He's the kind of person who will spend days reading 500 sources just to answer the question. He doesn't sit down at a blank sheet of paper every Monday and ask, "What are we going to write about this week?" He just has these natural questions about the world. This is one of the things that he, Nadia, and Stuart have in common. There's a natural curiosity that spills out of the writing. You can tell the person has deeply considered something, and maybe that's just what makes it more enjoyable for me. **Jackson:** That's part of great writing. **Tamara:** But at the same time, it doesn't over-explain. Stripe has a principle: speak up to the reader. You can trust that the person you're writing for doesn't need you to spell out the implications of every single argument. For one, that would make the piece too long. For another, you want to assume a certain competence on the part of your reader. If they are unfamiliar with something, they will just look it up and figure it out. **Jackson:** Scissor statements. **Tamara:** Exactly. Had you not said that, you would have deprived the keen listener from discovering that concept on their own. That might have taken them down a rabbit hole where they find things like \*I Can Tolerate Anything Except the Out-Group\* or Scott's reflections on Propion. You don't have to overexplain everything. Good nonfiction writing can be just as fun and take you on just as much of a journey as good fiction writing, even though you're doing different things. **Tamara:** Earlier this year, I finally read \*Frank Sinatra Has a Cold\* and sent it to our group chat. It's amazing. I get why it is the canonical profile. This profile is written without Gay Talese ever speaking with Frank Sinatra. How do you construct this piece of writing that is a journey and is truly fun to read? C Right. **Tamara:** There’s this digression into his mother, and you realize you want a whole profile just of her. You get his weird relationships with his ex-wives, his super sweet relationships with his family, his perfectionism, and his more unsavory connections. You get all of this because he's able to write in a way that's more like music than straight prose. Ideally, you end up at a point where I'm reading it and I always know I'm reading this person's writing. Not having that doesn't mean your writing is bad, but I do love seeing a signature. **Jackson:** You are known to write very deep essays on various topics and send them to a small group of people or one person. How do you think about audience in terms of your writing and the public-privateness of it? **Tamara:** It is layers of irony that I have my particular job and I refuse to write publicly. I don't even tweet that much anymore. There are a couple of reasons for this. One, part of what I'm trying to do when I write is to figure out what I think about something, and I don't really write unless I'm moved to. I used to do a lot of this thinking on Twitter when it was a place where you could A/B test thoughts. It wasn't the norm that everything you tweeted was a complete thought. You were just testing out a belief you have, and somebody would certainly come along to correct you. **Jackson:** But it was a little unfinished, and that was allowed. **Tamara:** And you could go on this shared inquiry together, which is interesting and beautiful. But Twitter is totally professionalized now; it's like our LinkedIn. Every tweet is a chance to get hired by somebody. There are all these implications to what you tweet, and I don't enjoy that. I like the intimacy of a personal correspondence. I can still have that dynamic that was so great on Twitter, but with people I care about and want to hear from. You're not dealing with people who are determined to misunderstand you, which happens if you get an audience large enough or if your tweet escapes containment. You tweeted about pancakes, so you hate waffles. **Jackson:** Yes. **Tamara:** I don't have enough self-control to ignore those people. If I'm not careful, I'll end up two or three replies deep with "egg\_lover\_624389," and that's not a way to spend your day. I am, however, a prolific Redditor. **Jackson:** I would not have guessed that. **Tamara:** I love the intimacy of a personal correspondence. During COVID, Ryan Orbach and I had a long-running thread where we emailed each other every day about something that was on our minds. They were very different in terms of what we were thinking about day to day. There was one day when I wrote about what it's like when people put you on a pedestal and how dehumanizing that can be, or what happens when you do that to other people. There was one day where I just wrote about management, and one day where we wrote about the interior design of condemned places. These are places that say to you, at least in America, that we really dislike you and you have done something wrong to end up here. In a lot of places, that might be mental institutions or sometimes public housing. We often take this very punitive view of public housing—that it shouldn't be that nice, it shouldn't be beautiful. A lot of times, this is the approach people will take to schools and prisons. Day to day, we were thinking about something and exploring it together, and that was really fun. Every so often, I'll put together these curriculums for myself. I have my "woman curriculum," and I'm just reading all sorts of things. I'd never read Nora Ephron, so I did the woman curriculum. I just really value this group of people. A lot of what we all have in common is that we're really curious, really responsive, and we love the written word. You can just inquire. Tyler says this in a piece recently: "inquiring together." And I just want to inquire together where it feels most fruitful. Right now, it doesn't feel like Twitter is that. But I have this Substack that's just sitting there and I haven't done anything with it. Maybe I'll do something. Here I am on this podcast. **Jackson:** Here you are. **Jackson:** It's a good reminder that writing, and anything creative, but maybe especially writing, doesn't have to be one-to-theoretically-everyone. ## [01:57:29] Reading & Biographies **Jackson:** Do you have any advice for reading? **Tamara:** Do it. **Jackson:** Wow. Tammy Winter of Stripe Press on reading: Do it. **Tamara:** Do it. Just read widely, read a lot, read all the time. But the best advice that I could give on reading has been given by somebody else. It's a guy called Henry Oliver. He's based in the UK and he has a Substack called The Common Reader. What I love about him is he is such a passionate advocate for reading, but specifically for reading the classics. There's a reason why certain books have endured over time. He's a huge advocate of reading the classics and of letting yourself be challenged. Today, there is way more infrastructure than there has ever been in human history to do that. So you don't get caught up if you're reading \*Madame Bovary\*. **Tamara:** There's the difficulty of reading something that was in a different language and is now in English, or the difficulty of reading prose that you're not used to, if you're reading \*Bleak House\* or \*Middlemarch\*. A fun thing I can offer is that I think, just like people can get writer's block, you can get reader's block. I was going through that. I have to read as a function of my job, but there was a point where I just stopped reading for pleasure. The thing I did was pick up the least nutrient-dense, most ridiculous novel that I could. It's one of those novels where you know where it's going 30 pages in, but you have to keep reading. It was called \*In Five Years\* by Rebecca Serle. If you were to Google it, you'd see that it is very well received by lots of people. A lot of people love that novel, and there's nothing wrong with it. But I'm not deluding myself. This is not hard literature. It was the thing that I needed to break the ice and start reading again. You can just start by reading a little bit at a time. A lot of people's challenge is that all of our attention spans are just totally shot. The way that you pick up that habit again is the same way that you eat an elephant: one bite at a time. **Jackson:** Why do you love biographies? **Tamara:** I love a biography. It's related to what we were saying earlier: Interesting life paths often don't repeat, but they rhyme. If you're really interested in people, one place you can go and immerse yourself in stories about people is biographies. 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. Because a lot of interesting life stories rhyme, you can draw a lot of courage from them. You can read about people. The biographies that I'm most interested in are not the ones from 20 years ago, but from a hundred years ago. If we care about things like agency, you can learn way more from the fact that Walt Disney's mother wouldn't let him go off and fight in World War I. If you were younger than 18, you had to have a permission slip from your parent. Because she wouldn't write one for him, he forged her signature. Or Booker T. Washington. His autobiography is called \*Up from Slavery\*, and he walks across state lines for the mere possibility of an education. He walks for days, and somewhere in the middle of the walk, his mom dies. He's squatting in a cabin in the woods when his brother has to come and tell him that their mother has died. And he just keeps going. He finally gets to the school, and when he gets there, there's no guarantee that he's going to be allowed to be educated. He ends up being something akin to the janitor. When he's not taking lessons and he's not studying, he's also cleaning the school. This education is totally formative for him. Or to take a totally different example, Anna Wintour was a nepo baby, but that's not what's important about her. What's interesting about her is that from a very early age, she constantly called her shot. She's sitting across from Grace Mirabella, who asks, "What job do you want?" "Yours." You can borrow a lot from interesting people's life paths. I certainly have. Those are the kinds of lives that I'd like to rhyme with. Sometimes in other people's stories, you can pick out these important traits that you wish you had in your own life. Maybe in the past, I've borrowed things I wish I saw in myself. **Jackson:** Oh, wow. **Tamara:** Borrowing courage. Let's take Teddy Roosevelt. Teddy Roosevelt experienced a lot of tragedy in his life. His mom and his wife die on the same day, Valentine's Day. It's also the day his wife gives birth to his daughter, Alice, who he names after her mom. He writes in his journal that day, "The light has gone out of my life." He basically stops living for a while. He leaves his child with his sister, Baymi, and just leaves. He has to go. 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 had anybody close to me die before. I experienced so much grief because I'd never had to do that before. Sometimes, if we're honest with ourselves, we're borrowing the qualities that we wish we had in ourselves. Good fiction can often do this, too. This is part of the reason why good children's literature is so good and so important. **Jackson:** Right. **Tamara:** It's able to teach. It takes young children seriously and tries to give them the tools they will need to confront the things that are inevitable in life. **Jackson:** Right. **Tamara:** They will face grief. They will fail. People like, let's just take an example, C.S. Lewis or Brian Jacques. He wrote the \*Redwall\* books that I used to love. I was obsessed with those books. They have a fundamental respect for their reader. I think a lot of people who read a ton also think this way, borrowing these qualities from the people they're reading about. But also, it's just fun to read about people's lives. You get the highlights, but it's nice to dig into the minutia. I love the minutia. **Jackson:** Yeah. **Tamara:** There are some real There are some real limitations to biographies. Sometimes they're only as good as whoever is capturing it. And there's a lot that you just leave out because you have to make it a clean story. Often in a biography, you want there to be a through line of the story. **Jackson:** Right. **Tamara:** You almost begin with the conclusion in mind. That's not the worst thing in the world, but it does color how you have to read biographies. A cool thing about biographies is that sometimes the best ones suggest who should have a biography that doesn't. You read Walt's biography and you realize, where's the biography of Roy? Or you read \*Frank Sinatra Has a Cold\*, and you realize, I need a biography of his mom. What an interesting woman. A force of nature. That's fun. **Jackson:** I love that. My final question is higher on the difficulty, so I'm sorry. I want you to give me a title for three prospective future biographies. The first is Patrick Collison. The second is your father. And the third is you. **Tamara:** This is insane. If we start with Patrick, hopefully he never listens to this. **Jackson:** That should probably be the easiest. At least you have the most distance. **Tamara:** What's interesting is that a lot of people will assume what he would be interested in. In fact, he has a lot of wide-ranging interests that aren't what you'd expect. For example, he is obsessed with great architecture. His prospective biography would be one of two things. One would be a really obscure term that comes from biology or something, with an extremely long subtitle that gets unpacked in the foreword. **Jackson:** But it's also a metaphor. **Tamara:** Exactly. Or it would be a very elegant, simple term. I think it's the latter, because one of the people that he really loves and admires is Christopher Alexander. There is a lot of relationship between things like \*A Pattern Language\* and building great software. He would take something from architecture or from a totally unrelated field that is an elegant and beautiful term. Something like \*A Pattern Language\*. That's not exactly it, but something like that. **Jackson:** You also have to make sure Christopher Alexander gets mentioned in every interview. I do, so I'm glad. **Tamara:** It's literally illegal if it doesn't happen. For my dad, one of the great things about having a great dad is that you have the period that is a canon event. This period where nobody in the world knows more than you do. I've never known more than I did when I was 18. If you are so fortunate to keep having your dad around, you eventually get to this place where you could call him every day and say, "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 so personally: "I know that you will always be able to find happiness, but what I really want for you is contentment." So maybe the title is \*Contentment\* or something along those lines. That means something very specific. **Tamara:** I travel a lot. I love being professionally curious and trying a lot of things. A really happy and meaningful life is one where every little thing that you do is imbued with meaning, so you don't need to constantly be chasing novel experiences. That was something his mom told him, and I think that's probably my dad's. Mine, on the other hand, would be some tortured metaphor. This is a total cop-out, but it's a little bit like talking about tacit knowledge, where you need a bit of perspective to be able to name something. It would be better to have somebody that really loves you or really hates you suggest a title, because it's hard to do yourself. It feels really self-aggrandizing. I don't want to answer this. **Jackson:** That's a fair cop-out. You need some distance. You have a lot of things left to do. **Tamara:** That is a trend, though: people writing memoirs at younger and younger ages. **Jackson:** That's true. Maybe it's time. The most Tammy thing to me, the inescapable thing, is that you truly, deeply love other people. We've talked about it a lot, and it's something I admire. **Tamara:** Maybe something along those lines. We'll keep workshopping it. **Jackson:** I have to come up with a title for this episode. Tammy, thank you very much. I genuinely mean it. This was wise, fun, funny, and full of life. **Tamara:** Someday we'll tell the story of everything that we had to do to get this episode. **Jackson:** It was all worth it, genuinely. Despite some technical difficulties. **Jackson:** Thank you. **Tamara:** Thanks, Jackson.