EP 324 – Creating a Canon for Progress: Empowering Global Entrepreneurs with Essential Knowledge – Tamara Winter – Commissioning Editor of Stripe Press

by | Jun 12, 2024

"Well, we think of this catalog as, ideally, a kind of cannon for progress, both in a very sort of explicit sense when it comes to, again, growing the GDP of the internet, making it much easier for people who have very ambitious ideas about a company they want to build to do that, and in an easier way than they might have to do if they were just trying to figure out everything themselves. You don't need to reinvent the wheel." - Tamara Winter

In this episode of the Asia Tech Podcast, Tamara Winter, the Commissioning Editor of Stripe Press, shares her insights on the unique mission and values guiding Stripe’s publishing efforts. Stripe Press aims to disseminate practical and provocative content tailored to a specific audience of high-agency individuals such as founders, executives, and technologists.

Some of the topics that Tamara covered in more detail:

  • How the creation of Stripe Press was serendipitous, born during a conversation between Stripe’s co-founder John Collison and entrepreneur Elad Gil.
  • How physical books offer a timeless and beautiful presentation for important ideas. The tactile experience of a book, from its cover design to the feel of the pages, adds a layer of significance to the content.
  • A dedication to curating a catalog that serves as a canon for progress underscores Stripe Press’s commitment to providing essential knowledge to its audience.
  • Stripe Press’s philosophy is that “the way you do one thing is indicative of how you do everything”. This ethos ensures that each book they publish is not only informative but also a work of art.
  • How Tamara’s own background, growing up in a culturally rich and diverse environment, shaped her understanding of the importance and the power of ideas.
Read the best-effort transcript

Read the best-effort transcript below (This technology is still not as good as they say it is…):

Michael Waitze 0:04
We’re on. Hi, this is Michael Waitze. And welcome back to the Asia Tech Podcast. We are joined today by Tamara Winter, the Commissioning Editor of Stripe Press. Thank you so much for coming on the show. I got it right. It’s sort of because I want to make your data.

Tamara Winter 0:24
Tamara, camera. That’s right, because there’s three there’s like three pronunciations. There’s Tamra to Mara, for anybody who watched Tia and Tamera, then there’s Tamara for anybody outside of the US. Then there’s Tamera, which, as far as I can see is just my dad.

Michael Waitze 0:38
That’s awesome. That’s awesome. And I only say this to people before we start recording, I want to know how to pronounce your name because even I want to get it right. I want to try. And the reason why is because like I said, before we started, your parents made like an active choice to pick a name that they really loved. And they kind of bestowed it on you and gave it to you and they don’t want other people just a muck it up and guess. Do you know what I mean? You know,

Tamara Winter 0:59
I totally agree. And I grew up in a part of Texas, where is it was quite heavy with immigrants in in Dallas. Fair enough. And you get used to at some point, and this wasn’t necessarily my issue, because my name is just Tamara is pretty easy to pronounce. But you get used to this thing where people will kind of either Americanized their names or pick entirely new names. Yeah. Because it’s difficult for people to pronounce. And what I love about I guess, the past few years is that it’s become, I think, particularly after Game of Thrones, it’s like, if you can pronounce generis, you can pronounce this other name.

Michael Waitze 1:32
So I’m so glad you said this. Because I lived in Japan, I lived in Asia since 1990. And I lived in Japan for 22 years, and I worked with guys whose names are like, hudco. Not that hard to pronounce. But he was like, God, never mind. I’m just gonna call myself Harry. So people in in the rest of the world can say my name is we’re always disappointed because I was like, That’s not your name, though. Do you know what I mean?

Tamara Winter 1:52
That’s right. And I always hate when I are. That’s a really strong word. But I always feel very disappointed when I learned that I’ve been mispronouncing somebody’s name. And they didn’t tell me don’t correct me. Yeah. And I think it’s so important. That’s your name, not mispronounced your name. Right. And it’s not it’s not like an inconvenience for somebody to call you the name that you were given

Michael Waitze 1:53
at least try that anyway. I don’t want to dwell on this, but I can’t believe I messed it up. After all.

Tamara Winter 2:17
I’m gonna No, don’t worry about it.

Michael Waitze 2:18
I’ll try to get it right at the end. Okay. Before we jump into the main part of our conversation, let’s give our listeners a little bit of your background for some context.

Tamara Winter 2:27
Sure. So I think for the purposes of this conversation, so as you said, I’m the current commissioning editor at stripe press. And what that essentially means is that I spend most of my time thinking about what comes next in the catalog the future of the catalog. So straight press is the publishing imprint of stripe. We’re a global technology company duly based in San Francisco, and in Dublin. And our whole goal is to create, I mean, our mission is to grow the GDP of the internet, but we create economic infrastructure. We’re companies that want to start scale and grow really sophisticated businesses, typically on the internet, but increasingly, right, everything is kind of omni channel. Yeah. And so I am the commissioning editor of straight press, we published 15 books to date, we have two parts of our catalog. One part of our catalog is called our turpentine books. Now, those are the books that are quite practical in nature. And we’ll get into this a little bit further afterwards. The other side of our catalog is our provocations. And so yeah, we chose those names very intentionally. And so now, before I was working at stripe, I’ve always had a deep interest in economics, and specifically in why some countries and economies grow faster than others. I was born in Nigeria, I grew up in Texas, as I told you, yes, I was born in Lagos, Nigeria. I only lived there for two months, which is long enough to get all the inconveniences without having been a native born American. But not long enough to get any of the cool stuff like Nigeria, you know, so So people always and it’s like, you don’t really count. And I’m like, Well, it took me much longer to get my driver’s license. You know, tell that to the DMV. Yeah, so that’s my background. What’s working?

Michael Waitze 4:14
Can I ask you this though? So if stripe is, as you say, it’s the payment infrastructure of the internet and frankly, for off the internet as well, right as this omni channel when online to offline and offline to online kind of merge into one thing. I get like, I look at all of stripes products, and I get it. What’s the point of the strike press? Like what was the you know, like, what John and Patton were sitting around one day and said, We need to have our own press. We need to be our own publisher. What sure why?

Tamara Winter 4:42
Well, I get this question a lot. And I think before I’m going to answer this, but I think before we talk about why straight press, it’s helpful to know something about who we’re talking to. Right. So many for many publishers. The sort of total addressable market is anybody who reads books ours is, I think, much more clinical than that. So the people that we’re talking to very much resemble stripes, user base, right. So these are people who our audience tends to be very global, very high agency are curious and people who are working in some form or another to push, push and advance the frontier of human knowledge and capability. Fair enough, so many of them will be founders, others will be execs, other technologists, but it’s a pretty wide audience to spin within that you also get academics, policymakers, and so on. Now, when stripe was created, I just mentioned to you that I was born in Nigeria. Now, for for a founder, who was trying to start a company in Nigeria, it takes just guess about how long it takes just to register a business.

Michael Waitze 5:49
So I live in Thailand. So I’m not sure it’s that difference probably faster in Nigeria to be fair, I don’t know six months.

Tamara Winter 5:58
Right? So nine months, a year. Yeah. And about half of your per capita income. And when you try to say that to somebody who is like I am, I live in New York now based in New York, it sounds like entrepreneurship is some sort of a scam. And you think about the fact that data is very expensive. In many parts of the world, it’s just full of friction and fees. So huge expenses and time and money. The reason for stripe to be started is that’s no way for the we want to increase the GDP of the internet, it’s simply should not take you two thirds of the year just to start your business, right. That, to me is just absurd. That’s why stripe was founded. Similarly, if you’re a founder, let’s say you’re in San Francisco, it’s hard enough to get access to the sort of the sort of top founders, executives, investors, you know, to get capital from them or time from them. It’s hard enough, if you’re in San Francisco, it’s that much harder if you are anywhere else in the world. And so while we think our main contribution to increasing human prosperity, and increasing the GDP of the internet will be through our product, the second and key way that we do that is by disseminating ideas that we think are important interests. So I told you about the turpentine side of our catalog. Yeah, you can feel free to interrupt me at any time, I

Michael Waitze 7:19
just want to make a point about Atlas, right? Because I do think that it’s actually really important for people to understand that you’re not just saying we want to make it easier by giving a better way for them to make payments. But there’s an entire infrastructure around startup and Corporation as well, that says, even if you’re in Lagos, even if you’re in Bangkok, we have a way for you to set up a corporation, I don’t I can’t I don’t know if it’s a C corporate or not. I can’t remember C Corp in Delaware in Delaware, right. So that’s the place where everybody’s going to want to set up their companies anyway, I just wanted to be clear that you’re not just talking about it. But there’s actually a product there that does that for you. So you can go from nine months to three days. I forget how long that was pretty fast.

Tamara Winter 7:56
Exactly, Michael. And this is one of the things that drew me to stripe in the first place. Because a lot of people talk in very philosophical terms about, you know, easing the process of entrepreneurship. But Atlas is a very concrete way that we do that. And it is incredible to talk to people, like for example, you know, everybody, all anybody wants to talk about as AI. Just headquartered not too far from us in our in New York is a company called runway, which I’m sure you’ll have heard of. They’re an ML company for video creation. They now you know, I don’t know how many companies can say that they’ve contributed to an Oscar for everything everywhere all at once. So not just any movie, right? Every single one of the founders, they have three founders were born outside of the US. They used Atlas to incorporate now they use stripe for a lot of other things. But I love that you pointed that out, because it’s I think for a lot of people who have never had to think about things like a month long waiting time between Yeah, filing to incorporate your company actually getting it it’s, it’s very hard to make that concrete for people. Yeah, similarly, go ahead. Well, nobody starts their company knowing how to constitute a board, knowing how to think about product, how to start a company. And in fact, right, I think the the open AI saga, you know, some months ago showed us that even people who have been around the block, in terms don’t necessarily. And so are you listening? And so yeah. And in fact, Sam, who is I think, fantastic. He is one of the interviewees in our very first book, high growth handbook. And so it all kind of comes full circle.

Michael Waitze 9:36
I want to get back to something else you said about why some countries grow faster. So I studied economics as well and I lived outside of my home country and I’ve lived in Southeast Asia now for almost 13 years. So I’ve lived in a developing company, a country another developing country, and now I live in the sorry to develop countries now developing countries, right. And I wonder as well, like, Why does Thailand grow slower than Then the United States, right? Why is Singapore growing so fast? And yet Malaysia is less fast since they used to be the same country? And I wonder, from your perspective, right? If you think that having products like Atlas and all the other products that are part of stripe and say, you know, if you can’t do it in your country, we can do it on the internet, right? That’s that infrastructure you’re talking about, that’s getting built and it’s built? Do you think at some point, those countries are gonna have to change the way they operate, because so many people internally, and now building companies remotely, and then not even repatriating capital, so they’re completely leaving themselves out, and giving the benefits to the established companies and countries already, when they could do it themselves.

Tamara Winter 10:40
I love that you asked that. Because just this morning, I was chatting with a woman called Sarah, who was, I’m in Singapore right now. So we’re chatting in Singapore, which people may not know. And she works for open gov, which is part of Govtech in the UN in Singapore. And she was telling me about how they actually have been, you know, when it comes to a lot of the work that they do is about how governments can integrate technology and use data and more interesting and sort of incisive ways. And what was so interesting is that their biggest collaborators are, in fact, not the US and UK like you would expect. But other emerging economies not that Singapore is an emerging economy, but emerging economy. Yeah, they just came back from Ethiopia. And there they met some folks in from Rwanda, they’ve spoken a lot with the Government of Cambodia. And it’s so interesting to me, because I think what you’re finding is the internet has this democratizing effect where, you know, it used to be that if you were if you weren’t in San Francisco, right, so you could have been in Garland, Texas, where I grew up, forget it, you know, there’s no way that you’re meeting and Arthur Rock who’s going to finance your startup. And what we’ve seen at stripe, and certainly I think other companies will bear this out is that increasingly, it’s not, it’s not like the end all be all being located in this, you know, 30 square mile area of San Francisco. And so you, I think you do see countries really kind of feeling that competition, and nobody wants to, nobody wants to see really talented, sharp people, everybody wants to build many people, right, they want to be able to do build a company like Stripe, where right where they are right, you know, saying that somebody needs to move to San Francisco to be able to, you know, build a company of stripe scale is first of all unsustainable. And second of all, we know at least now, right? The trends are showing people are sort of leaving the US or they’re feeling less pressured to have to be in the US or London, or what have you to build a really successful and robust company. But the part that you pointed out was the competition. Yeah, that is what’s so interesting. Before so when I was working on charter cities, I would kind of keep track of things like what governments are kind of making, making overtures to people to come move there. Finland, Finland had, like, you know, their sort of year long search for people to move to Finland. And then after COVID, they had like Helsinki and a box, which you could apply to get Helsinki in a box, you know, you see, you see, not just you but in Saudi, you see African tech, it’s so interesting to see the competition, not only between, you know, it used to be the US is like competing. Nigeria is competing with the US for their talent. Now, it’s, oh, I’m a talented engineer in Africa. I can go to Egypt, I can go to Kenya, I can go to Rwanda. I can go to Ghana, Nigeria, South Africa. Yeah. And so it’s just a really exciting thing to see all this regional competition. So collaboration. Oh, I

Michael Waitze 13:41
love it. I love it. If you could go back, I think it’s like 65 years to the founding of Singapore, right? When it was no, no. 60 years, 58 years

Tamara Winter 13:47
when it was kicked out of Malaysia. That’s right. Yeah. And

Michael Waitze 13:51
we’re just just like a fishing village. And if you had predicted to me or to anybody back then that would have the highest GDP per capita, almost in the world, but definitely in the region, for sure. Nobody would have believed you. But what they’ve built there is something pretty cool. But what they first had to do is go to other countries and find like the best little pieces of every system that they had there, implement them there in a really interesting way. And then 30 years later, or 40 years later, you know, the UAE actually came to Singapore and said we want to build the DIFC, right so the Dubai International Financial Center, we want to say who’s the model for this and they went to Singapore learned a lot took back and and of course they customize it because the UAE is not Singapore, there are differences there. That’s right. And what’s even cooler isn’t only because you brought up Rwanda, is that Rwanda and Burundi together have kind of gotten together, at least in my reading, and have gone to Dubai and said, We want to build the DIFC here. And they want to like now they’re passing from Singapore to Dubai into Africa. And I’ll tell you what, it’s scary because once that happens, it’s I know it’s there. 51 countries in Africa, but it’s still one point something billion people want to 1.4 billion people. And you know that comment He’s getting his stuff together. And there’s venture capitalists in Egypt and in South Africa, and once they start investing in Nigeria, and in Ethiopia, and in Kenya, I think the world forgets how like resource rich the whole continent is. Well

Tamara Winter 15:12
in Nigeria to for that matter, right? Yeah. Yeah, big, who’s one of my, he’s one of my inspirations. he co founded Andela and flutterwave. You know, how many people consider co founded one sort of wildly successful company versus two, he has the Africa Future Fund. And he’s very invested in, in just kind of really seeding Africa’s tech ecosystem. It’s just so promising. Yeah. You know, something. So when I was working on charter cities, they were sort of a common, a common thought when it came to, you know, can you build cities from scratch, and everybody wants to study, Hong Kong, Singapore, Schengen, and Dubai very carefully. And the more I spent time in the ecosystem, the more I appreciated how little I actually knew about each of those companies, or countries, excuse me, and in children’s case cities and how they became successful, right? I think, particularly in America, and particularly people who are in economics, I’m going to tell on ourselves sort of that there is just a complete lack of nuance. And like willingness to kind of complicate the story, like just just in let’s take Dubai’s case, right, Dubai had its first bridges, airport, road port, all of these things before they ever found a drop of oil. And when they did find oil, they had much less of it than their neighbors. And so people will look at somewhere like a Dubai and try and kind of pinpoint the causes of success. This is what ends up being quite tricky about economics. Yeah, yeah. In the end, it’s very difficult to answer the question in any sort of succinct way about why some places grow faster than others. What we do know that institutions seem to be a really meaningful part of the puzzle. And so when you look in the case of Singapore, Hong Kong, Schengen, Dubai, all of these places thought very carefully about their institutions. And it’s funny, because so I spent a lot of time in Zambia, working on charter cities, and we got to go to the Zambian Central Bank, which, you know, story for another time, or maybe later in this conversation. But we spoke a lot about them visiting Schengen. And what you will learn is that Africa is littered with special economic zones, they are truly all across the continent did not know, but especially Economic Zone is exactly you wouldn’t know. Because it’s, you know, that lot of good. The central bank governor said that it’s done us and, and it’s very interesting, because we were, we went to the Lusaka East Special Economic Zone, met a woman called Monica, who her company is called Java foods. They basically create fortified foods. And she had worked in Nigeria for a long time she was in she was back in her native Zambia, she wanted to set up her business and her factory in the Lusaka socket, use special economic zone. And it didn’t have any power. So it has no taxes. No, it has no special visas, a special thinking regime regime but no power. And so I think there’s a real danger, and trying to earn over learn the lessons of Singapore, Shenzhen, Dubai, Hong Kong, or any place without really kind of, as you said, thinking very carefully about which institutions matter exactly, and how to how to kind of really mix and match the things that matter. It’s so fun that we get to talk about this, because it’s been so long since I’ve gotten to be really steeped in this literature. It’s for anybody who’s listening. The book that I was referring to about Dubai is a book called City of Gold. Okay. And it’s an excellent one. And, of course, when it comes to Singapore, you kind of have to read from Third World to First, but certainly don’t want to stop there. Because as I said, you know, when people talk about Singapore in the US, it’s similar to when we talk about Scandinavia. Yeah, there’s just like, I don’t know, there’s just a real lack of nuance.

Michael Waitze 18:59
Oh, for sure. And find it. Like, I’m sure, like anybody United States, not anybody, but mostly anybody just go find it on the map. I did. Anyway, I love the fact that you brought this back to books. Because my mind is racing trying to like provocations. I think I understand. That’s get to that second, but turpentine. What does that mean?

Tamara Winter 19:18
Yeah, so turpentine is based on a Pablo Picasso quote, and he says that when? Well, I just have been a bookworm my whole life I can tell, which has been fun, but I’m sure it was, like exhausting for my dad. We had this sort of ritual where he gets to USA Today. And it’s stolen within the week. And you know, maybe he finds it again, and maybe it’s got like taffy on it by the time he gets it back or something. Growing up my favorite person was like, truly Wolf Blitzer. If you’re African, you grew up with CNN on so it’s like Wolf Blitzer. Christiane Amanpour. But the turban tine part of our catalog. So when Pablo Picasso says that said that when art critics get together, they talk about lofty ideals like form, and structure and meaning. Yeah, but when artists get together, they just talk about where to get cheap turpentine. They care about sort of the practical stuff. And so when we started stripe press, the big focus, as we talked about earlier, is that if you are somebody who’s coming to one of these books, you’re building, a fast growing company, you simply don’t have time for the fluff is sort through a bunch of fluffy stuff to get to what you actually want to know about product market fit about hiring, not whatever. And so we have a couple of books in that vein in our catalog, high growth handbook, our very first book, which I love that book, it was written by a lot, Gil, who was an early stripe investor A lot is he’s representative of my favorite type of turpentine author, when we’re looking for those authors. We’re typically thinking about who is when we think about this subject, who is the person to write this book a lot, Gil is one such author. So he was early at Google, he was a VP at Twitter. He’s co founded several companies. And he has invested in something like 40, to 50, unicorns. And so many of the fastest growing companies, particularly in Silicon Valley, but increasingly elsewhere rely on a lot of his excellent expertise. He’d written a blog for years, about different facets of building a company. And he came to John Collison one day, and they were having lunch. And he and a lot mentioned to John that he was putting a book together based on his long running series of essays. And John said, well give it to us. We’ll put it together in a book, we’ll call it. I don’t know, Stripe press. And that’s how striped press was born. And it’s so important that it was that book, because it was instantly the feedback that we got with a book like that. You’re not reading it for fun, right? Because it’s all about the discipline of scaling a startup. So it’s going to be everything from you know what to do now that you’ve got product market fit, how to acquire customers, how to constitute your board, how to think about things like your exit, are you going to have a merger? Are you going to go public? Are you going to get acquired, and it’s littered with interviews with folks like Mr. Taneja, Paul Graham, Patrick Collison, Sam Altman, Marc Andreessen, CLAIRE HUGHES JOHNSON, I’ll pause and clear he’s Johnson because she’s the author of our latest turpentine book, which we can get into. But I’ll just pause there first,

Michael Waitze 22:33
I want to make a metaphor for you. And I want to see if you agree with this, right, because you said something that’s really important to me that most founders don’t have time to sort through a bunch of things and find the information that’s relevant relevant to them. And I want to make I want to make the reverse, not case because I agree with that completely. But a reverse statement that says that that’s the biggest problem for most startups to begin with. Because what you’re talking about is discovery. How do I discover the things that are important? And I think for most founders, the idea for them is not how do I raise money? How do I find product market fit? I would argue with people about this, but I would say is, your biggest problem is how do people discover you, and I’m not talking about pure marketing, I’m really talking about discovery. And I think it’s really great that you made that point, because at the core of just like trying to learn something is just how do I even find out what I need to learn? Right? That’s right. Yeah. And that’s

Tamara Winter 23:25
why you say this. There was a tweet I saw the other day, about how can you tell somebody is a really, really excellent high IQ, not in the sort of number sense? Like how do you how do you know you’re dealing with somebody who’s incredibly sharp, and multiple people made the same point referring to folks that they had worked with, it’s people who can, in very few questions, drill down to the essential heart of a particular issue, or of a matter. And you see this often, with not just successful one time founders, but multiple times successful founders. And, you know, let’s just move on past founders, really, really effective operators as well, you know, when you’re meeting with them, and they are able to relatively quickly take from chaos ambiguity, what have you and figured out very quickly, what the actual crux of whatever the issue is, and it’s, it’s an excellent thing to behold. And we hope that our books are just that all the way through, right? So we don’t need to kind of convince you of the importance of entrepreneurship or convince you that you should have managers or that you should hire in a thoughtful way, right? We assume that you’ve got all of that. And now let’s give you the actual substance that you’re looking for. I want

Michael Waitze 24:34
to ask you something else. I remember my when my brother was in medical school, and this is gonna have to be 30 years ago now.

Tamara Winter 24:42
So you and I are both the sibling that didn’t go to medical school that and

Michael Waitze 24:46
believe me, I’m still hearing about it. Well, okay. My sister

Tamara Winter 24:50
graduates in two weeks graduations. I’m sure I can eat right, right. Congratulate, in a way congratulations to us. I feel like we all went through medical school today. Congratulations,

Michael Waitze 25:00
exactly. But I remember talking to him, I said, Wouldn’t it be cool, if instead of like carrying around that clipboard that doctors carry with him that just had was just a digital representation of all this stuff. And every time you went into the room and just NFC knew I didn’t know the NFC chip, but you just knew where you were and who was in the room and stuff like that. And you could just have all their information with you at all times, it will be so much easier to search for stuff, you’re not flipping through pages. And he said something really interesting to me, he said two things really interesting to me. He said, that’s never gonna happen. So he’s not as into tech as I am. But he also said, doctors want to touch the paper, they want to write it down themselves, they want to remember and I’m curious why, in the age of like, everything being digital, and with no, I’m serious about this, right, with stripe itself being like a digitally native company, why you decided that it was a good idea to print books out?

Tamara Winter 25:54
That’s right. I think that books are among the oldest technologies. And every time I say that somebody will roll their eyes but like it, and they endure every book is is a story between the author and the reader, right. And these books are one of the best ways that we have storytelling and speaking across generations, right. And it’s interesting, because I was just doing something a fireside chat in Sydney last week. And my interlocutor said, you know, the first thing I did when I got this book, he’s holding one of our books was smell it and sell your books.

Michael Waitze 26:33
It’s like getting a new car, though. The greatest thing about a new car is it’s not like the speed and all that stuff. It’s like getting going. This is new. This is new. It’s like fresh paint. Yeah, I won’t say that. I smell. Yeah, no, I agree. But I want to know why there’s something too, but I’m I’m 30 years older than the founders of stripe, right? So for me a book is the way that I read and learned everything. I can’t read a digital book I’ve tried. But there’s no way to do all the things that I like to do with a book on a Kindle or whatever the book reader is, you can’t do the same thing. You don’t I mean, you can’t fold the paper down. You can’t put an ace of spades into like, lock the paint like this can’t do any of this stuff. It’s no, it’s not nearly as fun. But I want to know why you did.

Tamara Winter 27:16
Right. Yeah, I think that we think that these ideas are timeless. Don’t they deserve a presentation that suits that? Yeah. And so at that point, it’s, it’s more than just for us? And I love this question, right? Because, exactly, you know, we do two physical products. One is terminal or point of sale, device. And then the other is straight press books. And what we’re saying right like is that if you take this book, right, you need to know how to do something, you need to know how to scale an internal function. You want to think of it as sort of systematic way about engineering management, whatever. That deserves. A not just a physical presentation, but a beautiful physical presentation. Yeah. Well, I always say, you know, you can’t judge a book by its cover, you shouldn’t? Well, you actually can’t, you can’t. And you should actually. And you can think you can, you can think of the sort of the time that went into designing these books is like a downpayment on your time for reading it. It’s just important for us to give the ideas a package that we think suits them. And it’s so interesting, because this is how it used to be when you publish books, right? And it used to be far more expensive. So there’s far less reason today to publish, you know, ugly or to not publish a book. Yeah. That’s right. That’s right. And I think it’s, it’s very interesting, because in technology, we’re always focused on what’s new, what’s coming next. kind of pushing the curve ahead. But I think with books, they’ve always been about what’s enduring, that don’t change, things that are relevant in more than 10 years and as choosing not only to have our books in physical form, but in hardcover form is our way of telling you and sort of a very expensive way that we think that this is worth you keeping it’s important. It’s worth you treating as an artifact. It’s important. Yeah. The sort of side effect of this is that you have people who I would call them straight press. Shelby’s I would say, you know, there’s some, it’s not zero, some part of our readership that just simply likes having beautiful books around for what it signals. So more than once I’ve ended up in a conversation with somebody who’s been super eager to show me their strike press Shelby. When you ask them what their favorite book catalog is. Oh, wow. And I’m like, the blue out of that. Can we be mad at them and right, and I actually somebody once said that and I’m just like, well, we have five blue books. It couldn’t be any good.

Michael Waitze 29:51
How How does this work though? So for the books that you don’t publish yourself? Sure. Like because I looked at I looked at the list of books right? All of them are not being publish by stripe press. They’re just books that have existed that maybe you or the team thinks are important. How do you like? How do you get the rights to them? What are the mechanics there for that? And why do you publish them when they’re already available?

Tamara Winter 30:13
Yeah, it’s such inside the inside, right? Well, we think of this, we think of this catalog as, ideally, a kind of cannon for progress, both in a very sort of explicit sense when it comes to, again, growing the GDP of the internet, making it much easier for people who have very ambitious ideas about a company they want to build to do that, and in an easier way than they might have to do if they were just trying to figure out everything themselves. You don’t need to reinvent the wheel. But on the other side, you know, this, this idea of provocations, you know, almost everything is upstream, or downstream, rather, of ideas. Right. So yes, the other part of why stripe press exists, is that we think, at the heart of great companies, great institutions, and lasting companies and institutions, our ideas, this isn’t to say that ideas are the only input, right? There are things like agency ethics, you know, there’s all sorts of contexts that matters. But upstream of everything else, is just what you believe about the world. Right? Yeah. And, and so when we when we think about, yeah, when we think about publishing part of the part of what we’re trying to do, and part of what I’m trying to do when I’m sifting through all the potential reprints in particular, is what do we think is important enough? That again, we told you, the people were talking to you specifically, are these very curious, we can assume they are globally minded, we can assume they’re extremely high agency, what do we think that they should internalize as part of their worldview? That will lead us to books like for example, The Art of Doing science and engineering. Now, that book was written by Richard Hamming. He, among other things, was a central figure at Bell Labs, he then went to the Los Alamos, and he also is a computer science pioneer, he invented hamming code. So you can think of him alongside folks like Claude Shannon. And that book is what’s his textbook at his last gig in his life, which was as a professor at the Naval PostGraduate Academy. And, among other things, it’s one part unorthodox memoir, one part manual for how to think, how to develop patterns of thought that are correct, you know, right thinking, it’s so funny in the US, we’re constantly having this conversation, or I don’t have to tell you, you’re American, about the quality of our education system. Were they really learning? Yeah. Does anybody learning to you know how to learn how to learn? And in fact, the subtitle of that book is The Art of Doing science and engineering, learning to learn. Yeah, the very last chapter of that book is a very famous essay called you and your research. And it’s all about how to ask the right questions about your life, how to keep your door open, as it were intellectually, at Bell Labs, what he noticed is that the scientists who kept their doors open, were much more likely to end up being the authors or discoverers of particularly important innovations, because they were much more likely to cross pollinate with somebody else,

Michael Waitze 33:22
somebody else was much more likely just to walk into their office and say, what are you working on? Because the thing I’m working on, I’m stuck, maybe I just want to change the world. And I can just talk to you, and then the guy leaves and goes, That’s what I was waiting for. Thanks. Enjoy your, you

Tamara Winter 33:35
know, ideas bumping into each other what is what is innovation, but that right, and obviously, you want to give yourself more shots on goal. And so that book, you know, Richard Hamming has he he died in the early 90s. Right? So there was nobody and he died without children. So with a book like that, it was a particularly interesting one, because it was very difficult to figure out who owned the rights. It turns out that book is what we call an orphan orphan book. Yeah, nobody really knows who owns the rights to it, there’s no clear clean claim to it. But if you want to go try and buy that book off of Amazon, it’s like it was like $1,000, but where we published it. So sometimes it’s very easy for us to make the decision. Got it, it clearly has value. There’s something there’s a sort of fundamentally important message there. And it’s incredibly expensive. And so there’s a bit of a meme now, where if there’s a book you love that’s out of print. And it’s like, $700, just tweet it at at stripe press at Patrick at John, and we’ll see what we can do for you. That’s one way, right? Another is just books that we just think should be more widely disseminated books like where’s my flying car? Yeah. You know, when we think about, for example, climate change. One, there are just competing schools of thought. So one of the ways that we do strike presses is sort of expression of our values in the world. And one of those values is that in fact, big, crunchy problems are tractable. And often they’re not impossible. And there’s a huge leap of world of difference between something that is impossible and something that is improbable. Yeah, for sure who do very important things in the world tend to live in that chasm, right. And so where’s my flying car is a different way to think about the climate crisis, which is very real, you know, one school of thought is that we ought to just succumb to degrowth, that we ought to impose austerity on ourselves. And it gets printed particularly pernicious when we think about what emerging economies ought to do. Right. It’s quite a lot of scolding that happens.

Michael Waitze 35:35
Yeah, let’s have you guys stay poor. While we have polluted for 100 years like it doesn’t that doesn’t feel right solution, does it?

Tamara Winter 35:42
Our industrial revolution, not you don’t get to participate in that feels like the wrong idea. That’s right. And it’s icky. It hits everybody’s ears wrong. Yeah. And maybe most importantly, it doesn’t even work. Whereas a different framing is that we ought to be thinking about abundant energy. And in fact, you know, from the beginning of the Industrial Revolution, our energy intensity, which is the amount of energy, you know, a civilization would consume was increasing pretty steadily 7% per annum until about 1971. And so Josh doors Hall, who is the author of that book, spends the entirety of where’s my flying car? Trying to answer that question, where’s my flying car? Why did we somehow get off track in terms of growth in 1971? And how might we recover that future that we were promised? And so with that, that book he self published, and we just reached out to him? Often, the way that we will select books is by cultivating if our author is still living cultivating relationships with them. It’s all very relationship based, because I can’t throw the same amount of cash that up Penguin Random House, or Simon and Schuster would be able to,

Michael Waitze 36:56
yeah, but also you’re publishing different books. And you actually have a reason like if you go, and again, nothing against Penguin Random House at all, but they don’t have a thesis, right? You have an idea?

Tamara Winter 37:05
Or they have a bunch of PCs? Yeah, for sure have like a million different imprints for sure. I totally understand what you’re saying. And I completely agree,

Michael Waitze 37:12
right? Like, I just want to I think I wrote it down like you have a there’s a reason why you’re doing this, right? You’re trying to, for these high agency, very busy founder style people and very high level thinkers, you want to give them just go don’t even look anywhere else. Just come here and read these books, because these are going to be the most effective way to learn the things that we’re pretty sure you want to learn. And then everybody else likes you want to learn. And sure penguin publishes great books and Random House. They all publish great books. But I don’t know which ones right. They’re ruining my discovery problem, which we talked about earlier. That was the only point I’m trying to

Tamara Winter 37:42
make. No, I told nothing against them. And it’s something we think about no. And in fact, one of my one of the people I most admire in publishing is an editor at Penguin, a woman called Bria Sanford, and she edits. But it’s interesting because she edits to very specific imprint, so one called Sentinel and one called thesis. And she in fact, has a very Exactly exactly. Right. And so it is interesting, we we kind of try and stay in our lane so to speak. But I think you just pointed out a really interesting issue, which is a much larger one that you see, across just the world of let’s just call it content. Yeah. We think very carefully when we’re selecting a book, because I think if you make things, it is your responsibility, not to add to the amount of clutter greed, and like mediocrity,

Michael Waitze 38:33
I won’t do it in a world I’d rather do nothing, you know, yeah, I’d rather do nothing, right. Yeah.

Tamara Winter 38:38
And so we should act, in fact, many fewer books then than our peers do. Because we would rather publish one book a year that we feel very strongly is worth your time. It’s the only thing you can’t get back then to publish, you know, 30 books of middling quality.

Michael Waitze 38:55
Yeah, no, I don’t want to be too I don’t want to be the mark cuz Stobie of like book publishing, right? And just like published was that, who is that you should look it up over time to market stop. It was this artists like the 80s, who was just like, all of my art stinks, the whole art world stinks. And I’m just gonna paint this stuff. And the more he said that he was just going to be prolific and make really terrible art, the more people wanted to buy it. And it was still terrible and mediocre, but he was just like, a really great salesperson. But I don’t want to be that I agree with exactly. I’d rather put out like one podcast a year that was just killer, good. Then then 1000 that were just like, man, it just

Tamara Winter 39:28
died. But what do you think that comes from? Because this is something I’ve been having a sort of ongoing conversation with different friends, different mentors, about is this something that can be taught this level of pride sensitivity to? Yes, yes. And and in an actual sense of shame. Like if you were to ship something that you thought was beneath what you know, you’re capable of that you would genuinely feel badly about that? Yeah, absolutely. It’s something that can be taught to you

Michael Waitze 40:00
Think so. And again, I think your surroundings matter. Here’s the thing though Marcus Dobie was specifically trying to go out and earn a ton of money in a way that was kind of that was that was his goal. My goal, I think, which is very similar to yours is, I want to have a substantive conversation that’s going to impact other people’s lives in a positive way. Like, that’s my whole thing. That’s why I do what I do. That’s why you publish what you publish, you could publish a really salacious book, or like some other kind of crazy book, and so millions of them, but why you will, what would be the point when you go home and talk to your family? And just be like, Why are you doing that? Yeah,

Tamara Winter 40:37
it’s so funny that you say this. Just it reminded me of a conversation I was having last week, where the my interviewer asked, okay, but isn’t, isn’t, you know, all of the signaling that you do about quality? Isn’t that fundamentally just signaling? No. And then he mentioned, a an anecdote from Steve Jobs, you know, the idea that the inside of the Mac should be as beautiful as the outside, even though no one was seeing it. Isn’t that kind of a pointless endeavor? No. And it’s funny, because that anecdote doesn’t come from Steve Jobs originally. It’s something he learned from his father, who was not, you know, a hit making technologist, but in fact, a an excellent mechanic. Yeah. And he. And so where that story comes from one day is that Steve was painting a fence with his dad, and his dad told him, the backside of the fence should be as beautiful because the front side, even if no one’s gonna see it, and it matters, not because anyone’s gonna see it. No,

Michael Waitze 41:39
go ahead. But because you’ll know exactly as you’ll know, you’ll know. And it

Tamara Winter 41:43
is a it is an expression of your values and your principles, that in fact, I did this thing to perfection. And it’s not necessarily for somebody else. And for that, I feel very fortunate because I’m surrounded by people like that, not just at stripe press. But within stripe. I think this is the thing that has distinguished stripe from anywhere else that I’ve worked in a very specific way.

Michael Waitze 42:05
I want to, yeah, sorry, I want to make another statement read because I think this is really important that the back side of the fence has to look just as good as the front side of the fence. Because you’ll know, it’s the same thing when you say like integrity that you do when no one’s when no one’s around, because and I’ll tell you why. It’s not just for the self satisfaction of doing the right thing. It’s because if you get into the habit of cutting corners in any part of your life, when it comes down to a stress point, you’ll always cut the corner. Because that’s always been the easiest thing for you to do. But if you’ve never lazy, sorry, if you’re never lazy, then that also seeps into every other part of your life. So like, you make your bed in the morning, you don’t put dishes in the sink, you clean them right away, like all these little things matter. And then your whole life is easier. And there’s no clutter getting back to that. Sorry, I interrupted, you know,

Tamara Winter 42:51
I love that. And you didn’t interrupt me because I think that’s exactly it, right? It’s funny because you know, anything, anything that you do, you can make it to like a bit of an idle. And so even as you said, it’s it, you don’t just do it because you want to feel good about yourself. But in fact, it just is true that the way that you do one thing is the way that you do everything. Yeah, I think so. And it’s so funny, because I think for I, I’ve just come up on four years at stripe, I was trying to think about what, what I thought was special about it. And I think everybody, you know, often you’ll hear people talk about their workplaces. And it’s like, wow, this is just the most, and especially people who are based in US tech companies are prone to moralizing, a little bit out of place, or Yes, yes, you know, there’s a bit of self aggrandizement, if you will. But what’s really interesting about this, this just this is just in the culture, this idea that it is just your responsibility, not to add to the amount of clutter in the world. And so you see it in every part of the company from the way that our product announcement will ship to the way that, you know, when we redid our new website, the way they thought about theirs, when when we launched the new website, this was two years ago, there was a spinning globe that we created, and just the amount of time and effort that went into the globe. Right? Like how you do one thing truly is just how you do everything. It’s so interesting. Because I think you’re so right, when you’re surrounded by people for whom that’s just the default option. Yeah, suddenly, you know, your standards start to increase. And I don’t know that I when I joined stripe was, you know, I think I’ve always kind of been sensitive to this sort of thing. But I don’t know that I had, you know, the unreasonably high standards for you know, what books are worth publishing and reading beforehand. Have you always had, are there things that you have? I know you’re supposed to be interviewing here? No, I’ve been asking people this recently. What are the things that you have unreasonably high standards for? So my answer I will tell you my laughter But mine is not this particularly lofty thing.

Michael Waitze 45:01
So, I always buy by the time I kind of get to know somebody really well, and they see the way that I work. And they see like how detail oriented I am I, I say that I’m an unnecessarily serious person. And I can see that it manifests itself in a bunch of different ways. I don’t think there’s a specific thing where I have really high standards. But I do think it’s really important that, like, you said that the back part of the fence has to look like the front side of the fence. And yes, I’m really specific about, let me put you this way. We did a video with a very large Japanese insurance company, and we were just about to publish it. And, you know, because my company is still really small, I had to approve it first. And at the end of the day, we filmed in their office. And in a Japanese office, there’s always a fixed place for the fire extinguisher was on the other side of the window. And then that window was kind of what’s the right word? You couldn’t see outside of it. But you can see the red thing.

Tamara Winter 46:00
So it was it was like a one way No, no, no,

Michael Waitze 46:03
it was like there’s a word for it. I can’t remember what it’s called. So it was tinted? Yes, kind of tend to have it was translucent, but not transparent. Right. But you could see through it a little bit. It was a cloudy, I know there’s a better word for it. But I can’t think of it. And I saw it and I couldn’t unsee it. And I can’t just do I can’t do low quality work. Right. So I actually had the editor figure out a way to create a mask that looked like that window, but took away the red before the other people saw it. So now if anybody listens to this, they’ll know that that was there. I just have really high standards around like getting doing the right thing, I guess I don’t know, it’s hard to explain. But it’s everywhere in my life. No, but I

Tamara Winter 46:42
it’s interesting, because there are, I’m very curious about if that is something that is just certain people are just like this in ways that maybe other people aren’t. And it’s frankly reminded me of Charlie Munger. And it was really interesting, you know, the amount of time we spent working on poor Charlie’s, in September of 2022, we went to Charlie’s house to film an interview with he and John Collison, one of the very first things that he said was that, you know, often I mean, he was 99, right? So he spent his whole life with people, and particularly the second half of his life with people asking him about, you know, different ways to make money and so on. And he was adamant throughout his life that not every dollar is equal. And the way that you conduct business was almost more important than anything else. And it was so interesting, because he started off that conversation. name dropping several companies that he just really did not rate at all. Because he felt that their way of making money was dishonorable. Yeah, you think about this, people who have these principles that they just do not bend, or adapt for anything or anyone who and people for whom they apply the principles most strongly to themselves? Yeah, I will say, the other half of this equation is certainly my particular bias, which is like a bit of self righteousness. You know, these things are not these things are not, you know, universally perfect. I think that is definitely sort of the underbelly of this like a bit of self righteousness, maybe sometimes pretension. But I think 99% of the time, it comes from a very good place. And it is, it’s like a gift to everybody around you, when they know that the thing that you were sharing with them is something that, you know, you’ve taken time on, you didn’t cut corners. And I love that you said gave that example about the video that you were creating, because there have been multiple times when we have delayed the launch of a book because we didn’t think we had the right cover yet. Yeah. And with any given book, we’ll go through dozens of iterations, which is, you know, fair to say. But we have to find the right cover. And sometimes I’ll tell you, it feels like man, like, do we have to do this every time? Do we have to Yeah, you know, work ourselves into a tizzy for the our next book. We’ve spent so long trying to figure out the perfect subtitle for that book. It’s so funny because you never hear books, referred to with their subtitle you only say the first part whatever’s before the colon. So I’m sitting here racking my like, I don’t know how many conversations we had about the subtitle. But when you talk about, you know, what it takes to make something that good, that’s what it takes. And that’s the sort of hard to fake stuff, not the not the I guess whatever people see us signaling. It’s that kind of stuff that’s unsexy, annoying, frustrating, time consuming for like dubious benefit it would seem and I think I’ve never regretted taking extra time on something I’ve never, but I have always regretted trying to ship something that I didn’t think was quite good enough for expedience.

Michael Waitze 49:57
Tamara Winter the Commissioning Editor of Stripe Press. I mean, I think we could have done another hour of this but I think that’s the perfect way to end on that sort of principled feeling of I want to get the right thing done and I kind of don’t care how long it takes. This was awesome. I really appreciate your time. Thank you again so much for doing this.

Tamara Winter 50:15
Thank you. This is an awesome.


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