Tamara Winter

Why a $106 Billion Company Publishes Books

VIDEO TRANSCRIPT

Why a $106 Billion Company Publishes Books

Tammy Winter at Main Street Summit 2025

Tammy Winter, who runs Stripe Press — the book-publishing arm of Stripe — sat down with the Main Street Summit host for a wide-ranging conversation about ideas, design, and why the most innovative company in payments also happens to be in the book business.

A $106B Company That Publishes Books

Brent Beshore: Welcome, Tammy.

Tammy Winter: I was actually hoping I'd get an intro like the governor got, but this is fine too.

Brent Beshore: Yeah — well, when you're governor, you can get one. When are you running?

Tammy Winter: I don't know. I live in New York City, so maybe as of the last election I'm going to move here. I'm a Texan at heart, so that's why I'd run.

Brent Beshore: Well, there you go. Tammy, you have this incredible side hustle you run for a big company called Stripe. How big is Stripe — $100 billion?

Tammy Winter: $106 billion at the last valuation. Sorry — it becomes a rounding error at some point. So yes: $106 billion company, and we're publishing books.

Brent Beshore: Before we get into why — you actually brought something?

Tammy Winter: I have always wanted to cosplay as Oprah. So — there's something under your seats.

Brent Beshore: You get a car! You get a car! Wait — she actually did it.

Tammy Winter: This is a book we just published called The Scaling Era. It's by a guy called Tesh Patel — Tesh has had conversations with basically everybody who's either heading an AI research lab or running a major company. In that book you'll find Dario next to Ilya next to Demis next to Zuckerberg. The reason I love that book: this technology is what they're telling us. They're telling us it may double GDP. It may kill us all. It may do both. We wanted to have a record of this moment in AI progress.

And then there's this one — The Origins of Efficiency. The cover image is an Airbus engine you'll find in a Tesla. This book is about why some things get cheaper over time and other things — like healthcare and housing — don't. Does anyone here work in manufacturing or supply chain? You three, let's talk afterwards.

Ideas as an Underrated Asset

Brent Beshore: Okay, but why does Stripe publish books at all?

Tammy Winter: We all know that ideas are valuable, but I think they are underrated and definitely an underappreciated asset — especially in Silicon Valley, where I work. Very few companies in a position to invest in ideas actually do so.

The concepts that built Silicon Valley — ideas about risk and ambition, human flourishing, free markets — these are not values that everybody necessarily agrees with. And we were in a position to put those ideas into books, which I think is the most enduring form of sharing ideas.

Brent Beshore: I'm sure a lot of CFOs in the room are thinking, "This is not something you should actually do."

Tammy Winter: We tend to confuse something being hard to measure with not being valuable. But for us, Stripe Press is profitable — it pays for itself. What's more iconic than a money-losing business you just keep going? But no, it's actually profitable.

Beyond that: about 2% of global GDP runs through Stripe, and a disproportionate number of those businesses are the most innovative in the world. So if our books — things like High Growth Handbook or Scaling People — help those companies grow, it shows up in our revenue. We have multiple deals where the first point of contact with a business was a Stripe Press book. So even if all you care about is the bottom line, it's still a pretty good bet.

Brent Beshore: I'm pretty sure no one reads books anymore — except maybe you, since you're apparently the Oprah of books.

Tammy Winter: We're about to sell our millionth book. So somebody's reading them. About a third of our audience just likes to buy the books and tweet the covers — and I respect that too, because a sale is a sale.

Brent Beshore: It's kind of like nerd jewelry.

Tammy Winter: Exactly. I had a funny call with a VC the other day — when he got on, the founder he was meeting with had every single Stripe Press book displayed in a very unnatural way, but half of them still had the plastic wrap on. So whatever signal he was trying to send, it didn't quite go through. But a sale is a sale.

Why the Books Are Beautiful

Brent Beshore: One thing I noticed since you gave me these books — they're beautiful. The covers are gorgeous, inlaid, nothing like normal books. Why do you do it this way?

Tammy Winter: If we're going to ask you to spend a long time with a book, it should be worth the time you're going to spend with it. A lot of publishers see design as an afterthought, but I think design is an argument for the quality of ideas. When a book is well-designed, it signals that somebody cared enough to do it.

We don't publish 15 books a year — what you see displayed plus these two are all the books we've ever published. That's because we spend a lot of time with the authors. We don't have any ghostwriters — every single one of our authors wrote their own book. We edit them. We fact-check them. You would not believe how many books are never fact-checked by anyone.

And then we spend a ton of time on design. These ideas took effort to compile; they take effort to absorb; and that effort will be rewarded. I can only describe the typical publishing aesthetic as "girlboss chic" — crazy fonts, a ton going on the covers, everything feels quite disposable. We wanted to create the opposite of that. There's also just a real value in the tactile physical object.

Turpentine Books vs. Big Ideas

Brent Beshore: When you're selecting books, I picture you as the Harry Potter sorting hat — "Gryffindor!" How do you decide what to publish?

Tammy Winter: Sometimes it's obvious. There are two categories. The first we call the "turpentine books." There's an apocryphal Picasso quote: when art critics get together, they talk about form and structure and meaning; when artists get together, they just talk about where to get cheap turpentine. We hope that for the books specifically geared toward businesses, they're cheap turpentine. You're running businesses — you don't have time to sit with every page. So those books are meant to be read when you need them.

Scaling People, our management book by Claire Hughes Johnson — she was Stripe's COO, though most of our authors had nothing to do with Stripe. She was at Google before that, led teams across Gmail, AdWords, and self-driving cars, and was so early her email is literally claire@google.com. The biggest chapter in that book is about hiring. I'm always thinking about what the unorthodox business curriculum looks like, and we look for the best person in the world to write each particular book.

But then there's a second category — the big idea books. What people believe about the world affects what they build or don't build. You don't see many people making the affirmative case for free markets anymore. So we publish books like Where's My Flying Car?, which basically argues that around 1971 we stopped caring about energy production and material advancement and switched our focus. I think that's an incredibly important message right now.

Brent Beshore: How do you know it's resonating?

Tammy Winter: A couple of years ago, Bono was doing one of those "what I've been reading" lists, and a few pieces down the page I see he cited Where's My Flying Car? as the thing that changed his mind about nuclear energy. That's kind of crazy. The kinds of people who read Stripe Press books are people like you — they have an extremely short feedback loop between idea and execution.

Sometimes the picks are just obvious. We were having dinner at Charlie Munger's house in 2022 and he said, "Maybe you guys would like to take Poor Charlie's Almanack and put that together." Many of you have the original — it's like a weapon, you can't take it anywhere. You're supposed to have it on your nightstand when you have a call with your LPs. So we republished it in what we think is a slightly less unwieldy package.

What's Coming Next

Brent Beshore: Give us the runway. What's coming, and what are you thinking about on the border of doing or not doing?

Tammy Winter: I really want a great book about iconic Japanese companies. I've read a couple of Honda biographies, a Sony biography I love, a Nippon Steel biography I really like. So I'm thinking about Japanese companies.

Our next Stripe Press book is by Stewart Brand, who created the Whole Earth Catalog. The thing he's most known for: when Steve Jobs gave his famous commencement speech, he said "Stay hungry, stay foolish." Many people think that's Jobs's line. It's not — it's Stewart Brand's line. The book is called Maintenance — the maintenance of everything. Stewart is 88 years old and has spent the last 13 years writing about why maintenance matters, why it is underrated as a force of progress, and why it may be the most essential thing to any civilization. I'm really excited about it.

Brent Beshore: What else is up your sleeve?

Tammy Winter: For the investors in the room — many of you will have read Nick Sleep's letters, so we'll republish and package those. But he's also been writing quite a lot more, and I'm really excited about that. Alongside it, we're republishing the biography of Frederick Taylor Gates — the Southern Baptist pastor who basically convinced Rockefeller he should be doing a lot more with philanthropy. We get a lot from him, but maybe the biggest thing we got from him is the University of Chicago.

Brent Beshore: Amazing. So if people in the audience want to write a book, they just email tammy@stripe.com?

Tammy Winter: Exactly — tammy@stripe.com. And I'll be around, so I'd love to chat too.

Brent Beshore: Thank you so much for being here, Tammy. Good to see you, and thanks for the books.

Tammy Winter runs Stripe Press, the book-publishing arm of Stripe. She spoke with Brent Beshore at Main Street Summit 2025.