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Tamara Winter on how book publishing and tech are more interconnected than we realise

During her trip to Sydney from New York, Missing Perspectives stepped inside The Stripe Press commissioning editor's world. From getting to meet legends of the investing world like Charlie Munger to connecting with founders in Pakistan, Tammy loves disseminating big ideas through books.

Tamara Winter, the commissioning editor of Stripe Press, was one of the epic women to hit the brightly coloured stage at Blackbird’s Sunrise event in Carriageworks, Sydney last week. It's there she shared her love of books as change-makers, and broke down how she approaches publishing.

Tammy was born in Nigeria, but grew up in Dallas, Texas. Spurred by the innumerable differences between Nigeria and the United States in terms of infrastructure and opportunity, she’s had a lifelong interest in why economies grow whille others stall, and why some economies grow faster than others. 

For a time, she worked on charter cities, before a chance meeting with Stripe Payments chief executive Patrick Collison led her into the world of the online payments giant. 

Now, Tammy heads up Stripe’s publishing arm - and yes, we’re talking physical, hardback books that you can touch, smell, and cosy up with by the fire. In an industry dominated by consolidated legacy publishing houses, more niche brands like Stripe Press, which was founded in 2017, are in rare company with McSweeneys, Panterra Press, Hachette and Spinifex.

From Poor Charlie's Almanack by Peter Kaufman (a distillation of all the key principles and mental models from deceased investor, billionaire, and lifelong philosopher Charlie Munger) to Scaling People by Claire Hughes Johnson (a Stripe and Google executive on how to manage and empower employees in fast-evolving companies), Tammy and her team want founders from Sydney, Australia to Islamabad, Pakistan to have access to great minds in science, technology and economics for US$30.

We cosied up on a basic - but functional - couch with Tammy backstage after her Sunrise talk "Craft and Beauty". We invite you to grab a wine or a tea, and dig into what flowed from our chat. 

Natasha Gillezeau: Tammy. Thank you so much for making the time to chat. There’s a great book that was recommended to me by a Missing Perspectives contributor Cara Davies - who started and sold a digital health tech startup - called The Unfair Advantage. What’s your 'unfair advantage' - the thing that makes you uniquely you, and how does this inform what you’re doing at Stripe Press? 

Tammy Winter: I think there’s almost nothing I wouldn’t do to satisfy my own curiosity about anything. A lot of the people I know have very particular skills. Within Stripe Press, we have an incredible typesetter - Kevin. We have a managing editor - Rebecca who makes the books more robust. We have our creative directors. My role as the commissioning editor is to ask what’s interesting and important enough that I think our readers should also ingest it? And I see myself as an audience member. I loved Stripe Press before I worked there. 

It’s unusual for a financial technology company like Stripe to have a publishing house. What do you think the tech world could learn from the publishing world, and what can the publishing world learn from tech? 

Books are the oldest technology, and books endure. The same books that are bestsellers now, were bestsellers a hundred years ago. So what technology can learn from publishing is to focus on things that endure generation after generation and will matter long after you’re around, because books are essentially a conversation between generations.

What publishing can learn from technology is a layer of flexibility and willingness to try things. I’m in the United States, so many of the big publishing houses have very established ways of doing things. It’s very difficult to get your book published if you don’t come in with certain things like a huge fan base or a literary agent. All of these things are barriers to entry.

But in technology, the minimum viable product of your company can be you and your laptop, and that’s so empowering. Now, more people can go and publish their own books, but for a long time, the publishing industry were these very powerful gatekeepers when trying to get your ideas out into the world.

At Stripe, do you have certain minimum requirements for authors? Because you need something better than 'Hey, I’ve just had this idea over breakfast'. What are your minimum requirements for considering an idea? 

We have a book proposal process. The number one thing I’m interested in is if I think your idea is robust and worth disseminating to our audience. It doesn’t necessarily imply you have a particular background. In our Turpentine range, which are very discipline based - for that type of book we are looking for the person who has expertise on a subject. 

Take Claire Hughes Johnston. She joined Google when it was about 2000 people, and then joined Stripe when we were about 100 people. She has learned more about how to build excellent teams, how to be a self-aware manager than all the years I’ve been alive. For those kind of books - we’re looking for the person to write that book. 

But for our more provocative books, you can literally be Nadia Eghbal, who wrote Working In Public. Her thesis in that book is that our understanding of how open source technology is built, maintained and created is really outdated. We tend to think of it as really collaborative - a couch full of people maintaining technology. But most of this technology is actually maintained by one person, or a solo person, working for very little explicit benefit.

Before that, Nadia was not an engineer herself, she’s not a maintainer herself, but she embedded herself among the people she was writing about. Kind of like Jane Jacobs in a way, very self-taught, very self-directed. So I don’t think I’m looking for a particular background. I'm looking for a particular profile of person - relentless, not easily satisfied, and extremely curious. 

I love that. I got the vibe from your interview with Making Media that you think about books as purveyors of certain ideas that you want to disseminate. To what extent do you see books as a form of entertainment versus as activism? 

I don’t necessarily see the two as opposed to each other. But the books we publish are very much a vote for ideas that we think are very important. What people see - their frames of reference - really affects what they do or don’t create. And when we think about Stripe Press, our big focus is just increasing the reference points that the people we’re talking to have to pull from.

This idea that maybe economic growth isn’t just a nice to have, maybe it’s a moral imperative. Or in management, before you think about how much you want to get out of your team, you should first think about self-awareness. You need self-awareness for mutual awareness. Or this idea that how you do business, and the standards that you hold yourself to, are so much more important than what’s easily measured, which is what I got from sitting around talking to Charlie Munger. He wasn’t super happy to sit around and talk about money - but he did have very strong opinions about how to conduct yourself in business.

After spending time with Charlie Munger - did you leave feeling like you needed to be a better person? 

People love talking about Charlie Munger and Warren Buffet like - they are best friends, richest guys - but there will never be another Charlie Munger.

The most important thing about him is that he didn’t think that every dollar was the same. He thinks that there are unsavoury, unjust, unpraiseworthy ways to make a dollar. He famously hated crypto.

He had such high standards - he told us this story of when he was walking through Costco, and he came across a manager who was being quite abusive to an employee - and he fired that guy on the spot. So much of what I learned is that the way that you do business is so much more important than almost anything else. And I think it affects almost every other part of your business.

Not only did he die quite wealthy, but that when he died, he had people working for him who had worked for him for forty years.

I think it’s so important to spend time with mentors, whether in person or through words, as they are like North Stars in life. Was there anything about Charlie Munger that you were like - putting crypto to one side for a minute - that this man is really from a different generation? Or do you feel that he speaks to really universal principles?

I think that Charlie was extremely focused on principles that don’t change. He said to focus on what doesn’t change. Pick the things that generation after generation won’t change, and that’s where you should invest your time and money. You definitely get the sense you are from a different generation - he designed and built his house 70 years ago. So it looked and smelled like your grandparents' house. 

Okay, so his interior design might not be millennial pink. 

Sure – but I think what I got from him is how much doesn’t change. Just last week I was spending time with another one of our authors, Stewart Brand.

Stewart is in his eighties. One of the things I find really interesting about both of them is that both Charlie and Stewart have/had long-running collaborators. They have these long-running relationships that get more and more interesting with each decade.

But it’s hard to answer this question - of course he’s from a different generation, but it’s hard to measure where this actually shows up. It’s in being quite cranky about certain things. But more than anything, he had this obsession with correct principles, and having the correct principles of the world.

Tammy Winter on ... her top 3 Stripe Press books

  1. The High Growth Handbook by Elad Gill

This is the book that started it all, which Tammy calls a "mini MBA for US$20".

Elad Gill was an early investor in Stripe, among other successful Silicon Valley companies. Gill shares his wisdom on everything from how to constitute a board, finding product market fit, and how to hire - and fire - the right people.

  1. Where Is My Flying Car? by Josh Storrs Halls

Josh Storrs Halls takes a contrarian position on how to respond to climate change - he argues that while it's great we're more climate conscious than ever before, the answer is not to consume less. Instead, he says we need more energy, but it needs to be clean energy, because part of what's made our civilisation so prosperous is increasing energy intensity.

3. The Making of Prince of Persia by Jordan Mechner

Jordan was 24 when he moved to San Francisco and started working on video game franchise Prince of Persia. At the same time as trying to create a video game, he’s going through the normal ups and downs of post-college life - renting an apartment, trying to date, looking for work.

"It’s a raw, unvarnished journey - and I love giving that book to young founders," Tammy says. "I read that book when I joined Stripe, I’d just moved to San Francisco from Washington DC, I knew nobody, and we went into lockdown. Like so many others, I felt like I was losing it a little bit. So that book was a great comfort to me, and will always hold a special place in my heart".

Editor's note: Missing Perspectives received a media pass to attend Sunrise courtesy of Blackbird to cover the event.