The Story of Stripe Press with Tamara Winter

Let's do this! Welcome to Making Media! Humans are an eternal quest for convenience. Save me time, make my life easier. My gosh, that's such a good start to an interview! Welcome back to Making Media! Our guest today is Tammy Winter, the commissioning editor of Stripe Press. Man, I have had the good fortune of getting to know Tammy over the past year and I'm so glad we finally got her on the show. As the name suggests, Stripe Press is a division within Stripe. If you aren't familiar with Stripe, it's one of the most successful private businesses started in the 21st century. Two Irish brothers, John and Patrick Collison, founded the payments processing business back in 2010 and have successfully been fulfilling their mission to increase the GDP of the internet ever since. Now from the surface, there doesn't seem to be great synergies or reasons why a payments business would incubate a publishing arm, particularly one that focuses on publishing or republishing physical books. But as Tammy explains, there is a lot more than meets the eye. We explore the origin story, how bono fits in, and the practical elements of producing such beautiful books. And as the proud owner of a few of them, they really do stand out on a bookshelf, not just for their covers, but also the curation of ideas, which is excellent. We recorded this conversation on Tuesday morning last week before the incredibly sad news that investing icon Charlie Munger passed away. Stripe Press republished Poor Charlie's Almanac earlier this week, and we talk about that two year project with Tammy in our discussion. So if some of the dates seem off to you, that is why. The newly released Stripe Press version makes Charlie's wit and wisdom more accessible and affordable, and I hope it manages to impact many more generations of business people and investors in the same way that the original helped me in my career. You can read it for free online through a truly remarkable website and write a press of put together, and I suggest you should order the hard back copy too. It's a great example of how Tammy and Stripe are making easier and more enjoyable to connect with some of the best ideas in business. Finally, before we get to the conversation, we were also fortunate enough to publish a conversation on the best like the best this week between John Collison and Charlie Munger. It's a fabulous and wide-ranging discussion that complements the book beautifully. I highly recommend you listen to that conversation and visit Stripe Press for more of Charlie's wit and wisdom. Now, I hope you enjoy our conversation with Tammy. Tammy, you are in charge of the best-licking books in business, and I'm a very, very proud owner of a number of those books. I've always been curious about how they came to be and how Stripe Press actually works, so really, really excited to explore that with you today. And I think I want to start at the very beginning. What is Stripe Press's origin story and also what's the purpose? Before I say anything, I should say, I would probably dispute the in charge of the title, but neither hand were there. Stripe Press is a really cool team of about less than 10 of us that work on it full-time, but it very much is a doughnut rather than a pyramid. So there's a life cycle to each book, and I think no part is more important than the others. Anyway, as far as where Stripe Press comes from, there's a short version, and then there's a longer and slightly more philosophical version, so I can give you either one. Let's go for the unabridged version, the full story. The unabridged version, I think the question I get most often when I tell people what I do is, okay, that's cool. What does Publishing have to do with economic infrastructure? Because Stripe Press sits within Stripe. And I think to answer that, it's helpful to know something about who we're talking about and who we're talking to. Let's zoom out a bit. So a very large part of our readership of Stripe's users. So there are millions of businesses around the world, and they really rely on Stripe to start or scale their businesses. But I think in some ways, the Stripe Press audience is both larger and more nebulous, but they share certain attributes. So in this group of people that we're talking about, you have founders, operators, investors, researchers, students, policymakers, and I think for a lack of a better term tinkerers. And so it's a very diverse and diffuse group of people, but they share a particular constitution. I like to say that they're a feedback loop between idea and execution is extremely short. They have an idea and they act on it. They are working in one way or another to advance the frontier of human knowledge and capability. And the last thing is that they believe that the world is getting better and can get better, but that doesn't happen by accidents. They're extremely high agency. So that's one part of it. That's who we're talking to. And I think it's helpful when thinking about not just Stripe Press, but probably any media to think about who they're creating for and who they're not trying to talk to. So we're obsessed with that person. I think both of you are that person. But you know, just as when Stripe was founded, it was still way too difficult to accept payments online. There was this idea at the time that it was a solved problem. So why would you start a payments company? That wasn't true. And similarly, there was a great tweet from David Holtz, the founder of mid-Journey a couple of weeks ago. And he said, you'd be surprised how much of the world's knowledge isn't written down anywhere. And this is really true, especially as it pertains to starting a technology business. So we figured it should be way easier to access clear actionable information about the critical elements, not just of building a startup, but building a company to last. And also that you shouldn't need to have a direct line to a lot of Gil, or Claire Hughes Johnson, or Charlie Munger, to be able to get this information. That's how Stripe Press was born. So why is it a bit of a natural conclusion? And I think not to spend too much time just talking about Stripe, but I think Stripe's attitude from the very beginning has been to see a problem that might even seem like a solved problem. And then decide that we're just going to solve it ourselves. This is true of the origin of Stripe. It's two of things like Stripe Atlas. I used to work in policy, and people in policy tend to focus a lot on the public barriers, the regulatory barriers to starting a business. But there are all sorts of private barriers. The amount of time it takes to get a bank account. The amount of time it takes to register a business. So you get something like Stripe Atlas. The problem with carbon removal, it was a really nascent market, and then Stripe Chromit comes along. So there's a logic to it. The lack of really clear, actionable, easy-to-access information about starting and scaling a business. That's where Stripe Press comes in. And also rip increment, which for a long time was our magazine that we published specifically for developers. Yeah, that's why. That's the longer, more prosaic version. But the sort of version's fine. Everybody thinks that Stripe Press was founded by Patrick. They have half of the equation. It was a callusin, but it wasn't Patrick. It was John. So the shorter version is that a lot of Gil, he was an early investor in Stripe. But a lot of Gil is also every startup's best friend. So he's invested in Airbnb, Enduro, Gusto, Stripe, of course. Notion, PagerDuty, Coinbase, Brex. So many companies. So many excellent companies. BigmoRitual, etc., Ripling. I hope I'm not forgetting any, but I definitely am forgetting something. We can add them in, yeah. He's invested in almost every excellent startup of the last couple of years. And he was having lunch with John callusin one day and told him that he was planning to turn what was that a very successful blog into a book. And he had been blogging for years about all the subjects that are relevant to startups. For example, for no reason in particular, how to constitute a board, something that's very hard to do for first time startups. And as we're learning for not so first time startups as well. And all these different things, John told him, well, why don't you give it to us. And we'll put it together in a book and we'll call it Stripe Press. And it's so funny because when we launch Stripe Press, or whatever it looks like now, it was a delightful experiment at the beginning. So you can go to Patrick callusin's Twitter account and just search Stripe Press. And you'll see that he launches Stripe Press with a single tweet. And it just says Stripe Press, Cohen, and no marketing. Just there wasn't a Stripe Press and then one day there was. And I don't think that we knew it would into what it is now, but that was about five years ago. And so as far as experiments go, it's still kind of early days, but it's fun that it's lasted this long. So the beauty of many great things is you don't know what they are when they start, but they morph into these beautiful things. You got into a lot there with that answer. And it's always good when I can just cross off questions because you've answered them. But I want to dive into something you mentioned there about what the goal is and the mission is and it ties into Stripe growing the GDP of the internet. And Stripe Press, John and Patrick mentioned this on a podcast that Stripe Press can inspire that next wave of entrepreneurs as well. And I think when I look at the books, you have some that are informational guides almost very tactical. And then you have some which are more inspirational in some ways. I think of the making of Prince of Persia, whether it's inspiring or it's this journey. It's one of my favorites. Oh, I love it. It was absolutely one of my favorites and one that I think about quite frequently. How do you think about those two things when you're thinking about making the books just in terms of these guides or these really tactical informational things versus the more inspirational open ended ones? I always want our catalog to be balanced between both and our mission statement is ideas for progress and that's a lofty mission. So what does it really mean? I think what it means when we break it down to its constituent parts is that we want to create a better landscape for entrepreneurship. But we also want to catalyze research and development. And we also want to, in general, inculcate the idea that problems in the world, big problems in the world are tractable. So this is true, whether we're looking at nuclear energy, which is something that versus my flying car talks about a lot or just the idea that economic growth isn't just a good thing, but it's a moral imperative, but to answer your question. So we have two big books and really a third, but we'll just talk about the first two, the first is turpentine. So while we don't just exist, we're not a content armistripe, we are very interested in what our users need. You're a first time founder. There are, like I said before, all sorts of things that you don't necessarily know how to do, whether that's constituting a board or hiring and then particular disciplines within technology engineering management. So one category of our book and actually the more successful category of book for us, if you look by the numbers, is the turpentine book. So there's a great public Picasso quote that I know you to know when our critics get together, they talk about lofty things like form and structure and meaning. And when artists get together, they just talk about where to get you turpentine. So we hope that our books can be cheap turpentine for our users. If you want to go to Harvard Business School, which I'm sure will teach you something about many things, in fact, about being an excellent founder, I don't know what that price tag is, what 60,000 a year. What's opportunity cost and counting compared to the much more reasonable $20, we have really got to raise the prices. So then that category of book, we're really looking for the world class expert in a particular discipline. A lot, Gil, not just as an investor, but at several different companies from Google to Twitter to color health where he was a co founder has seen all parts of scaling a really successful startup from the very first person to the 10,000 person. He is unusually well suited to write a book about how to think about taking your startup from the very first stages to potentially an acquisition or going public. And in that Pygothan book, you get interviews, not just with him, but also with Paul Graham, with Reed Hoffman, with Claire Houston, which is the seed of her book. And then you have, I think, an underrated book in a catalog, not underrated by the numbers is one of our most popular, an elegant puzzle, which is all about engineering management. So Will Larson, who's now the CTO of calm before that was at strike, this book about the discipline of engineering management and how to create a really effective engineering organization that information mostly wasn't really written down anywhere. And same thing for our very last book or most recent book, at least for the next week, scaling people by Claire Houston. It's amazing when she talks about where that book came from. Everybody wants the story of Claire had just been bursting to write this book and sees accumulated lessons of 20 years, and it is. But in fact, the reason for that book was actually quite a practical one Patrick and John would have coffee or dinner with founders all the time. And they noticed that over and over and over again, the questions that people had were questions related to Claire's domain of expertise. The founders start a company, they think a lot as they should about product development about customer acquisition, but there's this third pillar of a great company, which is the internal foundations, right. And really Claire's domain is planning for success. If you are a founder and you start, you get your first couple hundred customers or even thousand, you have to grow pretty quickly on the inside. And by that time, it's too late to go back and think about things like what's our philosophy on hiring, what are our organizational principles. What do we reward in this organization? What do we punish? How do people advance in this organization? How do you think about management? So that's where scaling people comes from. Those are turpentine books. But the other thing we think about a lot is, I'll give you, I guess, a more sophisticated way that I think about this, and then the much less sophisticated way I think about this. What do we think is important enough to meme into the minds of those people we were describing at the beginning, those people whose feedback loop between idea and execution is exceptionally short. What people believe about the world affects what they build or don't build. So if people think, for example, that economic growth is not just like a nice to have, but actually incredibly important in the foundation of progress. If people believe that when we look at where's my flying car, that in order to resolve the climate crisis, maybe the best thing that we can do is not just consume less, but in fact, tap into new and abundant sources of energy. If people believe that our next book is Port Charlie's Almanac, that it's not just great to do business, but the way that you do business really matters, the way that you conduct yourself, the principles that you adhere to or don't really matters. Those are the things that we just want the next Patrick and John call us in to be thinking about as they build their businesses and want the current Patrick and John call us and to be thinking about that too. So that's how I think about that category of book and the only other part is I also think that my background's not intact. It's in policy and economics. It was funny when I joined when I made my way into the industry. How many people have such short memories and also are very unaware of other industries which they can learn from one other thing that we try to do with the catalog is to provide context to the people who read our books. We want them to have context on the industry. So one of the books I think that our catalog that's quite underrated is the big score and the big score is great. It tells the history of Silicon Valley, Mike Malone, who's the author of that book. He was the very first tech reporter at the San Jose Mercury News, so it's in the mid 80s or so when he starts, but the book starts with the founding of Stanford. So the Stanford Sun passes away and the grant Stanford this land that comes to Stanford University and on through the variant brothers, Hewlett and Packard, fair child, semiconductor Intel, and it ends just as the Mac is being introduced or other books like the art of doing science and engineering Richard Hamming. He's not necessarily a household name, but he was critical about labs. He invented hamming codes. He's also at the Manhattan Project, but he and his wife worked on the project at the end of his life. He was a professor at the Naval Postgraduate Academy. So this book is one part on orthodox memoir another part history of how great things happen specifically at Bell Labs and that at the Manhattan Project and finally an imploration for people to take themselves and their work very seriously. So the last chapter in that book is a very famous essay called you in your research and it's really inspiring for me because I think so many people grow up today. It's not like a lament. I think it's very annoying. Everyone always thinks that things are getting worse, but I do think it's true that maybe culturally we've lost some of the idea that you should maybe not take yourself really seriously, but take your goals and your aspirations and your dreams really seriously. Again, that it's great to be optimistic, but optimism without agency is just polyannishness. So we really try to publish things that make in particular really young people. I love when I get to talk to founders and people who created really successful companies, but I'm particularly obsessed when you can catch people when they're teenagers. So having them really internalize the lessons of something like you in your research is great. And in the big score, one way to read the book is as a history of Silicon Valley. Another way to read it is as a celebration of people who were sort of unreasonable and every aspect of their lives and to say it's okay to be obsessive about the thing that you want to create. You mentioned that your background and roots are in policy. Can you draw the thread for us from there to here? I would love to get your personal story before we go further into the strike press. The thread is dramatic or not dramatic. The threat is hard to follow. I'm not super old. I'm 28, but I wouldn't classify that as all this. It feels old, but I'm now at the age where I get to talk to really sharp young people who are thinking about their careers and everybody always wants to know how can we repeat a particular path. I feel really strongly that you can basically not repeat any paths. And it's like I was talking about the art of doing science and engineering. I'm basically the anti hamming hammings entire thing was you should have a vision of greatness and you should execute on it. And that's certainly true for a lot of the people I know who have done great things just look at my sister. I sisters always know that she wanted to be a doctor and she's finishing up in med school in May. I was basically the opposite so I followed my curiosity throughout my career. So I think the way to understand my career is that I have been following Tyler Cowan around for the entirety of it. So I started off I studied economics at SMU and when I graduated, I really wanted to go work with Tyler Cowan or find some way to get on his radar. I loved marginal revolution and marginal revolution University, I tutored in college. And so I would use he and Alex taberox videos to teach, but I also read marginal revolution. So I went to Mercatus and it was really fun and I got to do research and I was primarily working on cronyism and corporate welfare, but also barriers to entry, so things like occupational licensing certificate of need laws, which make it really difficult for new hospitals to open scope practice laws, which make it more difficult than it should be for nurse practitioners or positions assistance. To practice, they can do a lot of the things that a doctor can do, but for whatever reason, it's just super difficult. Now as I was working there, it was great because you're working with some of the most interesting and effective scholars. I think that George Mason University is really underrated, even though it's increasingly very highly rated, but I just would do whatever I could to get on Tyler's radar. So I would drop stuff outside of his door, which was ridiculous, and I guess my thought process was, well, if I do this enough, he'll have to invite me in and then we'll become best friends and then who knows what we'll do together, but it never actually happened that way. I ended up actually meeting him at a book launch party and he was like, you know, you can just come say hello. And I'm like, what was all this for? And he has really become for me a really important mentor and it's like I talked to Tyler all the time, but he's one of those people who is constantly working in the background of your career. Moving obstacles out of your way or vouching for you in rooms that you're not in. And I just owe him a tremendous debt of gratitude. Now after that, I left and I went to work on charter cities. And that was extremely fun. I was born in Nigeria. I care a lot about just like I said economics and growth. It's easy and it's interesting to talk about economic growth when you're talking to people whose entire lives are. We take it for granted in the U.S. We're sitting here having this conversation over Zoom by Ryan Nigeria where I was born, even if I had all the money in the world, our there is just very unreliable. There's a great quote from Shalazza founder of Paystack, which Stripe acquired recently, but he was talking to YC founders and he was talking about how when you're in Nigeria, being a founder requires you to think like a state. You don't just have to think about product and customer acquisition, but in fact, you have to think about how to supply reliable power to your employees. So there are all these obstacles. So when people talk about economic growth and the way that it makes living standards better. I think about what happened for my grandmother when she could finally afford having a stroller at my age, she had three kids and was pregnant with her fourth and what that did for her and for her business. So I care a lot about economic growth. So I spent a lot of my early 20s traveling between Zambia and South Africa, Kenya and other places and it was really cool to talk to, for example, the central bank governor of Zambia and to talk to them about the potential lessons for places like Singapore or Shenzhen for Zambia. And I would meet people like Muayyama Sokwattwane, who's built one city is now working on a second in Zambia from the ground up. And at the same time, you had a lot of people in Silicon Valley who were very increasingly interested in charter cities as well for different reasons, but that was my first introduction to the valley. So that happened to meet Patrick Callsson at an event. And once again, I was like, look, I don't know anything about Stripe, but I love Stripe Press. In particular, I love Stubborn attachments. I love Tyler, Patrick and Tyler are very good friends as well. So that became an extra connection point. So I spoke at Stripe later that year. And I spoke about charter cities. And that's where I ended up meeting my first manager at Stripe Sasha DeMarini, who is an incredible woman and I could honestly talk about her forever. So this is 2019 and then in 2020, I was asked if I would maybe consider interviewing at Stripe. So I did and I started at Stripe one week before we went remote because of COVID. We might have buried the lead there with your background, which is quite fascinating. And that recent name, we got to work with Sasha on a project recently, which was excellent. So you've intersected with a lot of very, very interesting people throughout your career. It's very obvious the connections that you've made organically. I think before you got to Stripe, which is very interesting to hear how all of it ties together. Some of us step into the organizations and then we meet people on behalf of the organizations. This feels like it was very organic. The thing I'm not mentioning is that my biggest career tool was the artist formerly known as Twitter X. I grew up in Garland, Texas. I was born in Nigeria, grew up in Texas. And I went to SMU. So I didn't necessarily have a ton of exposure to people working in technology or in finance or anything like that. Actually, that's not true. Both of my parents work in finance, but I just was really interested in economics pretty early on. And the great thing about Twitter is that at the time I was 18 when I started tweeting. So about 10 years ago, you could tweet at Tyler Cowan and people would tweet back at you. This is insane. There is basically no other tool where you could talk to the people that you admire. And for me, the celebrities were brilliant economists that I was obsessed with. But there's no other platform where you could talk to these people. So I have gotten basically every job I've ever had through Twitter. And at first when I was tweeting was really deranged stuff. I've lived many lives online. At first, I was tweeting. It was very political and tweeting a lot about economics and there are all sorts of funny detours ideologically. But it was great because it was a way that if you had an otherwise unremarkable background. I guess I used a good school. And I really enjoyed it. And I did research in the business school because for whatever reason it was easier to do research in the business school than it was in the econ department. But Twitter became a really cool way for me to distinguish myself. And it was helpful because I didn't go to Harvard. I didn't grow up with tons of family connections. I grew up, like I said, in a lovely and quiet summer of Garland, Texas, the summer of Dallas, rather. So Twitter was a really, really powerful tool. You hear the story again and again and again. I think people think now the platforms been through a lot in the last couple of years. But I still think it's an incredible tool to meet people to find your people. It's a way to turn yourself into a bit of a lighthouse. So it's not always the easiest to go out and get people to take you seriously. We valorize the cold email. And it's not to say don't cold email. Do it. But another way to help yourself is to turn yourself into a lighthouse for the people that are interested in things you're interested in. So for me, that was a really cool way to demonstrate competence. Even if otherwise I didn't go to California until I was working. I started working at the Tardis Institute. So 2018 was my first trip to California. So I'd been to Zambia before I'd been to California. So I think Twitter was a huge, huge help to me. It's nice to balance the scales while everyone else is deriding the platform. I also got this job through that particular technology. So I hold hard to leave with what you just said. If we go back to strike press and you mentioned that it has a very lofty mission in terms of ideas for progress. How do you measure success relative to that mission? Is it something that we think about a lot in terms of media businesses? It can be hard, particularly when you're publishing physical books. So I'd love to hear you riff on that. This is a great question because when we were starting my predecessor, ReWolfson, she I think is just an incredible person. I think she's one of the striped as people I know and she's become one of my best friends. And I love looking back at the early documents that she and Sasha and Everett took back. Another colleague of mine who was like my creative partner for the first couple of years at Stripe. They were very interested in not measuring success the way that traditional publishers would. So if we think about again who we're talking to and we're talking about really our focus is people who don't necessarily have a lot of time. So they're not picking up scaling people because they just felt like reading a 500 page book. When it comes to turpentine books, what success looks like is somebody saying I didn't know how to do this. And because I picked up scaling people hiring got that much easier hiring is the longest chapter in scaling people. The whole idea is this information should be highly actionable and highly specific while still being general enough that you can modify it and choose your own adventure. So when it comes to turpentine, I couldn't tell you how many times I get emails, Patrick gets emails, John gets them, the authors get them. This is something I didn't know how to do and it helped me do this. And it's cool because you have these conversations with people, a friend of mine, Mishka or Xay, she is a founder and she was born and raised in Pakistan. She now is in California, but her first company called this code works at the Pinterest of code for her. A high growth handbook was an extremely helpful manual because if you're a woman entrepreneur anywhere, but in Pakistan in particular, these are resources that you don't have. But then you also will have this conversation with Toby of Shopify. The first time I met him, him telling me I love straight press. I love Shopify. So when it comes to turpentine, the goal isn't so much to be able to show Patrick and John these incredible sales figures. However, we are running a business here. It's really to help the people that we exist on behalf of do things quicker. But then it's more navelist on the big ideas side there. The goal really is to exact change. One of the things I loved about Mercatus is that you could not notch something as a victory if you didn't literally see policy change as a result of something you published. So the bar was very high. There were plenty of think tanks who just write papers all day and I'm sure they're very good, but they don't do anything. Mercatus's bar was that you do not get to call something a victory if you're in the monetary team. If you don't literally see a rule change at the Federal Reserve, it's not a victory. So similarly, I think the proof is in the pudding when it comes to who are we influencing? Who's actually making different decisions as a result of the books that were publishing? I think a really cool victory. And you don't always get something that's this clear cut, but this is really cool. So I love where's my flying car. Josh Dore's hall. He's this incredible mad scientist. He's a world's class native physicist, but he also wrote a lot about just energy. He's an energy fanatic. And he has this curve called the Henry Adams curve that he's names and the idea is the energy intensity of a civilization or energy usage. And basically what he notes is that until about 1971 or so, the energy, the Henry Adams curve had been increasing about 7% per annum and we stop. So he basically argues that if we look at why the US and not just the US, but the Western world seems to start stagnating in 1971, energy and our disavowal of continuing to create more abundant energy sources has a lot to do with why we start stagnating. And how do we kept on that path on the Henry Adams curve are GDP would be four times what it is today. And his question is how can we recover that future. So Bono noted nuclear energy hater. He was given a copy of where's my flying car by John at this incredible festival called the docky book festival in Ireland. It's huge there. So he got the book and you never know what's going to happen when you give somebody a book you hope for good. You can imagine my surprise when last summer I'm reading the New York Times and Bono is doing one of those books that really inspired me. And when I see that he's flagged, where's my flying car as a book that was very meaningful to him. And now Bono is a pro nuclear advocate. And can we claim total credit for that? I'm not saying we can, but it's very rare that you get something so clear cut. Or seeing revolt of the public, which really was I think a new and novel framing of thinking about the ways in which institutions lost the trust of the public. When we see revolt of the public being cited by universities and by the IMF and reports. Those are the things that we're looking for. We're looking for stubborn attachments to be cited by founders and policy makers as Tyler in that book. He's not just saying economic growth is good, but in fact, it's a moral imperative. So if you are in a position to do anything about growth, whether you're an entrepreneur or a policy maker identifying policies and working to increase economic growth. That's not just a good thing to do. That is actually your duty. You have an obligation to do that. We really are looking for those books to seep into not just the public consciousness, but specifically the minds of people who are in positions to do something about the issues that we care a lot about. So that's how we're marking success. But I have to say, I don't think anything will be a satisfying or as exciting as when I get to talk to a 12 year old at striped sessions last year. I was there and I met this 14 year old girl who just happened to be there. She had to be the youngest person there. I think there was like a baby there or two, but she's a 14 year old. And you're thinking, she doing a striped sessions, she just particularly interested in the latest releases of radar, but she came and I was just, oh my gosh, I have to give her all the striped press books. And I got an email from her couple of months later. And it was just the sweetest thing in the world, because I remember what it was like to be an 18 year old and to not have tons of money for the striped press books. I will say one more thing, which is that I was a pioneer pioneer still exists, but it was created as earlier stage, YC for just young promising talent anywhere in the world. When I was at the charter cities institute, we became pioneers and that was actually that trip was my first trip to strike. And that's where I meet Sasha and John calls in for the first time. We went to the library, we were given a tour and I was just looking at the striped press books and at this point, I'm not making a ton of money. So it's like I have tons of money to spend on striped press books and I was looking at them and Sasha was like, well, you can take more than one if you want. And I just never forgotten that it just meant the world to me. And so I'm excited. I love when you get to talk to somebody who's built something incredible, who loves our books. But I think that there's nothing really like talking to the 18 year old in Dublin, who has never been asked to take themselves and their ambitions and their goals really seriously. Well, it's super interesting because we think about this a lot and there are the things you can measure. And then there are the things you can't measure, but you know are true. And sometimes I don't always show up in the New York Times with a specific reference to a book, but. But increasingly was strike press books, they are, I have to say that. Exactly. And you collect enough of those, it becomes a body of evidence that I think is hard to deny, which is always going to be tricky. And it takes organizations with longer term visions and a willingness to understand that this isn't just going to be a direct number thing that you can measure. But I think those things are super, super important. There has to be this willingness to believe in things that you can't always measure. There's an analogy I love and I told myself I wasn't going to finish this conversation without talking about this. My beloved Dallas Cowboys, the Dallas Cowboys are in fact a pretty good model for how we got here. What do I mean by this? Okay. So in 1960, that's when the Cowboys are founded. And then just three short years later, Dallas became the city that killed the president. We're talking about this in the wake of this. It's been 60 years. And then just 15 years later, suddenly the Cowboys or America's team. I think people when they think about the Cowboys are really hyper focused on Jerry Jones. But if you go back to the beginning, the founder of the Cowboys is this oil billionaire called Clint Merchason. So he makes two really important hires, the president and the GM text sham. And then Tom Landry, the iconic Dallas Cowboys coach, the most beloved Dallas Cowboys coach of all time. So they're the triumph for it. So what happened? Well, nothing actually worse than nothing. The Cowboys lose for the first four or five years of Tom Landry's head coaching career. And everybody's like, fire this guy. What are you doing? This is ridiculous. Dallas again is not in a great place as a city, but we're just losing. And so what sham and Merchason decide to do is to extend his contract to give him a 10 year extension. And again, this is not the thing that, look, I'm not a coach myself. I'm not a GM. I've never owned a team, although hopefully that's something I can do in the future. But I don't think you generally, the conventional wisdom is not you extend the guy who's been losing for four years, but they do. And what happens? Well, the very next year the Cowboys start winning. And by the time Tom Landry leaves, he gets fired by Jerry Jones, they won two Super Bowls and the Cowboys are America's team. And I think people again, they over focus on Jerry Jones, but the great thing was that Clint Merchason and Tech Sham had the foresight to say, look, we want to set up this organization in such a way that text feels that he has total creative freedom. We understand that if we're going to make this into a winning organization, it's not actually going to be a one year play or two year play or three year play event. But in fact, it's going to be a longer term play. So by the time Tom Landry leaves, then in the next era, that's really arguably the Cowboys greatest era. But there is this early creative freedom and trust that was placed in him. And I don't think you get the same results without that. And I think similarly, I'm often talking to people about, how do you make your own striped press, which I think is that and of itself is just a funny question. But the question I think that's a better one is, what is the organizational setup that allows for a thing like a striped press to be started and also to be sustained. And I think you really do then need a Clint Merchason or a Patrick and John call sent who aren't constantly breathing down your next to ask, okay, what is the business case for giving an 18 year old in Pakistan, a free striped press book. And that's a really beautiful thing and it's a lucky thing and it's quite a rare thing as well, which doesn't mean just out here spending money. You'd be surprised at what you can get done on a surprisingly lean budget. I think that on the sports analogy, many people reference the bill, Walsh book, the score takes care of itself. And his first two seasons, he was the worst coach in the NFL. It was telling where whether it's the J curve, the hockey stick, whatever it is. Sometimes there needs to be that foundation building before there's the ultimate launch. So yes, I like any time we can pull the sports and even if it's the Dallas Cowboys, which will push side, I did have one other question, which is why physical books and thinking about technology business, very embracing of online with blogs, Twitter, everything. Now I do know that both John and Patrick appreciate physical infrastructure and everything. So there's a physical element to this, but I was wondering if there's anything there specific to why physical books. I mean, what's more enduring than the physical book? What is a technology that is more enduring than that? They're very few. So that's why there's almost nothing more enduring than books where we're talking about the Bible, the earliest scrolls. It's really fun to watch the scroll prize, which not for Edmund has been a helmet with Professor Brent. I can't remember his name in Kentucky. There's nothing more enduring than the written word. So that's why. But I think as far as the physical side, people often say, can you please just publish them in soft cover? Is there any reason you need to go to this particular expense? They all need to be hard covers. And to them, I say we are in fact working on our first soft covers breaking news. Yeah, yeah, you guys heard it first, but I think that ideas that are timeless that we feel are timeless deserve timeless boundings. They deserve to be presented in such a way that in fact, with our books, you can judge the book by its cover. I think it's important not just to think of the utility, but also to make it beautiful because beauty is a teacher. I think that the presentation should, if we really believe that the ideas in these books are deeply meaningful and useful, you should have an outer appearance that suits it and then a similarly timeless and not easily disposed of. To tie in with that and just a concept of beautifulness and Patrick on the best of the best recently talked so well about why he cares so much about how things look across the whole organization. Let's try to pass this square within that. I would love for you and with poor Charlie's element coming out. I would love for you to talk us through how these books come to be and how you think about the design and what they look and feel like. So when it comes to publishing a book, there are basically five elements that all publishers do to varying degrees of skill and craft. So one is editorial choosing what gets published, but also the work created to create a final piece of writing. And at strike press, I really do think strike press just has the greatest managing editor in the world Rebecca Hiscott. She just is incredibly talented. She works really closely with all of our writers and then the production defining the look and the feel of a book. And we really love we offer something called an author questionnaire because it's extremely important to us to understand what each author's goals are with their book. Do you want to have happened in the world as a result of you writing this book. The idea is writing that makes things happen. So we don't just want the work to stay on the page. And they work with our really creative team. So our creative director Jeff Halber. He spends a lot of time with the author questionnaire because he really does want to understand what are they telling me is important about this book. And how does it need to be represented visually, leave an incredible type setter Kevin Wong who thinks about how the book should be organized internally. You'll see when you get poor Charlie's Almanac that there are lots of QR codes because there's going to be a first time digital experience that I'm extremely excited about, but I can't say too much about just now. And then you have other folks in our design team Josh Miranda or art director, who is the person responsible for a lot of the amazing covers that you see for them. It's really cool how many things they make that never actually see the light of day. So for any cover you see there might have been 30 to 50 other alternative covers and sometimes we share with those alternative covers the covers that would have been. But we're constantly iterating and fine tuning and ideally there are a couple of people that we really want to be delighted by each cover number one is the author we want them to feel like this design has captured some important essence of this book that they're publishing right. And sometimes that means rev after rev after rev and there have been times when we even pushed back a launch because it was just that important to make sure we had the exact right cover for the particular book. Sometimes Patrick, he obviously is busy running a company, but he will often offer input, which is really helpful on the design because he also has something an idea in his mind of how things should look, but it really just speaks to the obsession of the folks on our team every person on our team. We're so terrified that you're going to pick up a book the people who again are reading our books. They don't necessarily have time to waste it's the only resource that you just can't make more of so we're always terrified that we're going to be wasting your time. You should feel that by picking this up and spending however long you spend with it that your life has been made better in some way that you've learned something that you know how to do something that you feel inspired in some way. And every single piece of how you interact with the straight press book should contribute to that feeling right so our team we just had an onsite and it really just is the most creative group of people and it's so fun. It's like doing an apprenticeship with the best people in their particular trade whether it's type setting or editing or Bobby who is the mastermind who gets the books everywhere. I've learned through working with him and through working on straight press the intricacies of the global supply chain and all the ways that things can go wrong and he's magician. So everybody just has this obsessive focus with what we do it's just fun it's cool very well set and how do these projects books come to be and in particular where the poor Charlie's arm that originate from. So each book is different in how it comes to us but often we're often the not a lot of straight presses relationship based. So some of these books are not necessarily on the market for a reprint and I think poor Charlie's is a really good example of that so some of our earliest books three machine or where's my flying car these are reprints but they're reprints that we acquired on the basis of pre existing relationships dream machine was genuinely one of Patrick's favorite books. And so Mitch Waldrop it was easier to get that book and by a similar token Patrick and John had dinner at Charlie's a couple of years ago and what I'm told is that that dinner three hours into it Charlie is like all right what's next and John and Patrick are like we're tired. So they're flagging and he's not and they just keep going and okay thought nothing of it they continue that relationship. And in the summer of 2021 we get a message from Peter Coffman CEO Glen air former chairman at West go and long time collaborator of Charlie's we got on the phone with him and he said look they had gotten a bunch of requests to reprint poor Charlie's on the. But they just were never that interested so we actually didn't ask for it was one of these really beautiful and totally serendipitous moments where they gave it to us. And it wasn't totally clear we would get this initially we're talking the first call and I think Peter China sizes up who really are these kids what do they know about Berkshire about we're Charlie's all maniac. I was I think 10 when the original came out so we're just talking and he tells us at one point that the publishing company that they worked with is based in Marceline Missouri. I was like there's only one other thing in Marceline Missouri and it's Walt Disney's hometown what are you doing in Marceline Missouri and he's like what do you know about Marceline Missouri and we just got into it. Peter is a huge Disney fan and so am I that's where we hit it off and it was so cool but initially what we were only going to do the question was we want to make poor Charlie's as widely accessible as possible. A lot of the early obsessives of PCA are not in America but in fact in India in China so their goal with giving us PCA was really to make it as widely accessible as possible and it took some convincing to say well why don't we also republish the book because I love PCA. But it is not a B tree in the sense that you cannot just take that anywhere. It's a great weapon should you ever need. It's not the most portable and so they said okay, okay, we'll also let you republish it and we trimmed it a bit but it's been so fun. The process of putting that book together has been the process of really understanding how a great person has lived his life at the beginning it was amazing. I would have calls every other week with Peter Kaufman and I was terrified of the beginning of doing something wrong and he just said you're not going to mess this up because we won't let you which is both really gratifying and also. So it's been so fun for the past two years really that's how long it's taken to one develop this digital experience so that when when we launch on December 5 anybody will be able to read the book in its entirety online for free but also for people who are true believers or just want the book will have the physical book as well. So the substance of it hasn't really changed we've kept the 13 speeches and talks that make up the core of it John callison wrote a new forward but we just think that this book is such a classic it's so important it's not just about how did you business but a way of doing business that I think is exceedingly rare increasingly rare so I'm excited for it next week you all are going to be the ones to launch the interview that we recorded last September with Charlie at his house in Los Angeles with John callison and there are more things that will be coming out. I'm super excited and I'm grateful to be working with you all I'm a huge fan of colossus in general I think you all are one of if not the freshest new network of editorial of media you tackle so many different things from business breakdowns to founders and what I love about y'all is that working with you is so much fun so much of a key to what we do. It's surprising but an editorial lots of people are not that nice. You're not the easiest to work with we hear this all the time from authors out terrible of an experience they have so being delightful is in fact a competitive advantage and you guys have that state so I'm grateful to get to call you guys friends but I'm also a huge fan. That's very kind of I'm glad this is not a video because I'm blushing currently it's mutual yeah it's very mutual feeling are we really can't wait for next week we have the fortune as you said of highlighting John Charlie's conversation and has only this to a few times already it truly is excellent predictably excellent but it is excellent. I want to get you out on this final question and you like us are an outsider in the media industry and you're making content I hate to call it content. I do too I really do hate that word apologies you making books that we absolutely love I would love for your reflections on the media industry and what you've learned about doing what you do now relative to where you were a decade ago. I think it's really helpful to not have grown up working in media but I've been steeped in it from a young age I would steal my dad's copies of USA today or time magazine or news week and so I've been reading and watching for a long time. So when I talk to people about media I think the thing that is so critical and that people often forget especially when you get really big that your audience is huge and super diffused that's hard to know who they are. You really want to know who you're talking to you want to have a sense of the uncommon denominators of your audience and what is it that they care about what do they respond to. And I know it seems kind of ridiculous but with every book that we consider we are thinking about I literally have people in mind and I think about how would this person react to it how that person react to it. We're just obsessed in the same way that you want your business to be obsessed with the customer we are obsessed with our readers and you can tell when somebody just really really really obsesses over whoever's on the other side of what they're making. So I take a lot of cues from interesting alternative and strange media efforts I think the whole earth catalog is just incredible you think about the whole earth catalogs principles they wouldn't publish anything in there that wasn't practical that wasn't actually a tool but also it had to be something that was fairly cheap to produce and procure. And could be easily accessed from anyone in the US or you look at Craig mod Craig mod one god willing we can get a book from him one day but he takes so much of what he does so seriously often his most notable writing for me at least is writing about walking walking how is it that walking can be the way that he writes about walking can unlock these incredible new worlds. I think about Kevin Kelly and his book vanishing Asia he's an anthropologist he is constantly evaluating cultures and trying to understand what we can take from them and you see a lot of this is just the DNA of the long now in general. Zander rose he has his research project on extremely long lived institutions these people are obsessives in a particular way and they're obsessed with things nobody else would be obsessed with it's ridiculous session is a practice. Yeah exactly that's actually what I'm really obsessed with right now and who I'm taking a lot of cues from I love people who are unreasonable about whatever it is they're studying who are tinkers because I think that what they do it's the Kevin Kelly line of a thousand true fans. You don't actually need to create for everybody it's actually totally reasonable and maybe even more powerful to be super super clear about who you're talking to who you're not trying to talk to. And by doing that you can end up creating something that resonates with a lot more people than your original audience I'll say a couple other examples I'm obsessed with Andy Matushak I think half of what he doesn't like I don't even know what's going on over there but he's so driven by his own curiosity and it makes everybody else. Want to know what he's up to I think Brian Potter is an upcoming strike press author he writes mostly about production efficiency genuinely why do some things get cheaper and other things don't and he writes about he's a civil engineer by trade. How much is there to say about the economics of steel it turns out there's a lot to say about the economics of steel and you all too I don't know I love people who are just incredibly curious and I take a lot of cues from people who were this exacting in their craft. I love teary muggler I think there's also designers that incredible but I love him what I love so much about him is that he had so many inputs huge sci-fi fan and so even see this in his run ratios he had multiple run ratios that are like really sci-fi themed his whole thing was that fashion can do a lot of things and one thing it can do is give you a perception of yourself that you didn't necessarily have before so his whole thing was he wanted to design for the woman who was force of nature and you think about the time he's coming up in the 60s 70s 80s where the role of women is really being re-expected. And everything he does is in service of creating this woman who is the force of nature down to the perfumes that he manufactures angel and alien alien is extremely polarizing perfume. It's very jasmine forward you love it or you hate it but that's exactly what he wanted people were forces of nature in fact are often polarizing so honestly I don't pay a lot of attention to the ways in which maybe traditional media is failing because I'm not sure that it would be particularly helpful but I am really obsessed with you can't see me. But earlier I was wearing my founders sweatshirt David Senra this is not revolutionary he sits in his room and he reads biographies and then he writes to himself about what he's learning and then he delivers that content to you. This is not revolutionary but he did it originally for an audience of one for years he was doing that and nobody was listening he said that not me he said that and now founders is huge everybody's listening to founders so I feel like there's a lot more to be learned from those people because those people don't burn out. You actually can't compete with David Senra because he's never going to stop doing what he's doing Stuart brand whole earth catalog was amazing but right now he's writing a serialized book for our partners works in progress on maintenance the maintenance of everything. It's so funny because he's writing them a chapter at a time but it's taking him a lot longer because he gets into these incredible digressions about particular things this man is 85 almost 86 years old if he's not already 86 and he's still doing this. These are the people that I like to take my cues from what a wonderful way to close I have some homework to do you do you do homework. Thank you so much for letting us peek inside the curtain that's right press there are a million more questions we have and we'll have to get you back on the show next year. Thanks for having me. Now we finally tied Tammy down into a recording we've been trying to get her on the show for a few months you promised and said hey I'm going to come on making media as a matter of when not if and finally we managed to make it happen and I'm very glad we did. Same it was great to do we've had conversations with her prior to this getting her on mic hearing more for background which I didn't have the full extent of was a lot of fun and then just getting to ask some of the questions that I was always curious about in particular it's very clear what they're ultimately trying to do. And I think how you measure some of those things is always tricky but just hearing a different perspective on how they're measuring things and to me there's something interesting about that thread of what does it mean if you can't measure it. One side of the equation but I think a lot of the most interesting things are really really hard to measure and inspiration or unlocking of ideas presenting people with the tools that they can then use to create things there's a real value to that and it is difficult to measure how that's resonating with your audience. But that doesn't mean it's not worth it and yeah it's just really neat to get a totally different perspective from people we respect a lot that are doing something similar to what we're doing with a different business attached to it. There's something to be said about as you could hear she's incredibly intelligent and eloquent and people she's operating with very accomplished as well there's so much to be said in these creative endeavors where you have to satisfy yourself first. So I feel like this is a really genuinely good piece of output like Claire who obviously scaled strived to a really big business clearly if she's really happy with that book the chances are the books really pretty good and that goes with all the authors that they work with and just their own sense of what's good and what's not is really important to this stuff and we talk about a lot on the podcast side. We don't always get it right but we hope that we have a decent barometer for whether a conversation is useful or interesting and whether it's not and you have to have that because particularly when you're publishing physical books and even podcasts. You don't get the chance to engage with your audience one-on-one very often often people will send that stuff but then it starts to feel like anecdotes and you think well maybe I'm missing the big picture here. So that internal sense of is what I'm putting out the world here additive useful interesting engaging all the above and I think that's what came through from Tammy as well. Absolutely do you have a favorite book the Richard Hamming's book is really I loved and there are chapters in there that I just couldn't understand but the other chapters more than made up for it and particularly his list of how to do great work and make a great living in a career that sticks me a lot and I make copious mountain notes on that book and there's something about just them being so beautiful. Which is your favorite but the making of Prince of Persia which I think is an out of consensus one but there's something to it being a very different time in the 80s and 90s with the development of a video game. The perspective of the person making that you can almost interpret him as lazy at some points yes this insanely long time horizon to build this there's just so many interesting personal anecdotes there's so many interesting anecdotes about where the industry was at this time. And where he travels so it's this neat personal story mixed in with a neat business story which I just really enjoyed it was that perfect balance of information entertainment for me. It's basically a diary isn't it yeah it's the journals that he kept while he was doing it that's why you get just a lot of very interesting things mixed in there. You're very good at this you've always said to me that you should write more of a diary quote unquote about your life and business and stuff and I think when you read books like that it shows you why when you go down to write them at the end of the day. This is nonsense was the point of it it seems like a very obvious thing there's nothing inspirational here it's just what happens today but when you then collect those together over a period of many years that you can turn them into something super useful not just for yourself. And your brain will play tricks on you I think one of the most interesting things now is even something like your phone that tells you what you're doing a year ago or a month ago or a week ago and you just forget your brain has a funny way of just filling in the last three days and making that 95% of what you think reality is versus the last three months or three years whatever it is and yeah it's just funny how distorted your views can become and then obviously changes what things were like in the past. So when you get these things those journals documented it's excellent and you can't do them after the fact so that's always a tricky part. Today to another plus one for physical media in this episode we talked to Amy asked the answer you said how important architectural digest the magazine is to their business and sickly even their YouTube efforts and you don't think there's a massive link between them but she very eloquently told us that there was and again Tammy saying we make books because they're the most enduring pieces of media that you can possibly think of again a fascinating insight for business has been built digital native from the ground up for developers I think 100% agree it's very interesting it's also not entirely shocking when you read. Some of Patrick Coleson's blog posts about what he's interested in and similarly with John and what he talks about they very clearly have an appreciation for physical infrastructure and I think just the physical world that we live in so it didn't shock me but at the same time it is interesting and I think it's a symbolic thing and it has meaning behind it so not to be taken with a great of salt that they're doing it. And we talked a bit about or Charlie's on and I remember people this is like eight nine years ago people saying I was reading to the list of investing books that I should read. For Charlie's on that would always be at the top of that list and then I finally ordered it on Amazon the price would swing around wildly some glad someone's holding that out and then if time this huge box turned up when I picked it up it was so heavy and I can believe that this amazing book that I'm kept talking to me looked as big and heavy and bulky and cumbersome as it did so I'm glad it's getting wrecked by in some ways because his wisdom and with does deserve maybe slightly need to form factor. It was a one of one in terms of the uniqueness of that book and it didn't quite fit right on a bookshelf nor as a coffee table book. It had its very own design that was specific to it so it'll be nice to introduce a different version of that I agree and I was laughing. It's not exactly a beetroot is the understatement of the year but yeah it's a special one and I think there are just timeless lessons in there. The other piece I'd want to recommend off the back of this conversation if you are still interested go and listen to Patrick as you want to see his conversation with Patrick and John Collison that we aired on invest like the best a few weeks ago. There's a really good segment in there from Patrick about why they sweat the details why they care about making things aesthetically pleasing and he articulates all the reasons that don't necessarily show up and pure cold numbers but they do in feeling and just culture. So I would recommend listening to that that's all I had. Likewise yeah this was excellent a lot of fun and we will talk to you next week.