How Books Shaped the Collison Brothers’ Path to a Billion-Dollar Company

with book recommendations to follow the same path.

In 2005, a 16-year-old Irishman named Patrick Collison found himself in Boston for the first time. Passionate about computers, he had sent an email to Paul Graham, Y Combinator’s founder, proposing a meeting. Graham accepted, and they arranged to meet at Café Algiers on Brattle Street at 2 p.m. While Patrick was waiting in the café, he saw Graham arrive, looking rushed. “Patrick, I’m so sorry but something’s come up. Can you wait here and I’ll come back?” Graham said, before hurrying out. Patrick spent the next two hours reading his book until Graham finally returned.

He could have felt impatient. Instead, he opened his book and read. It was another chance to learn. That quiet habit would define the Collison brothers: an insatiable appetite for reading to prepare for what comes next.

Café Algiers, Boston. Picture from The Harvard Crimson.

Patrick Collison and his younger brother John grew up in Dromineer, a small village on the eastern shore of Lough Derg in County Tipperary. Remote and poorly connected, the place had little to offer in terms of technology. Until their mid-teens, the Internet at home was so unreliable it was almost useless. So instead of spending their days behind a screen, the brothers used to play outside and immerse themselves in books.

Their scientist parents filled the house with books and encouraged curiosity without ever pushing a set path. Reading became a daily ritual. Physics, biology, history, biographies, novels, they read it all. After school, the two kids would go straight to the library in nearby Nenagh and spend hours among the shelves. It was in those stacks that Patrick and John first read about computers and the Internet.

For years, books were their only access to it. When the family finally installed a dial-up connection, Patrick quickly dived into programming. But the line was so slow that he always kept a book open next to the computer. “You could read a page of your book, look up to see if the page had loaded, and chances are it hadn’t, so you went back to your book,” he remembered during a talk at Startup Grind.

That curiosity soon found a stage. At fifteen, Patrick entered Ireland’s Young Scientist and Technology Exhibition with an artificial intelligence project that won him second prize. The following year, he came back with something even more ambitious: a programming language he had built from scratch, which earned him the competition’s top award and national recognition. John, just two years younger, was no less precocious. By the time he finished secondary school, he had achieved the highest-ever score in the Irish Leaving Certificate exams, a record that made headlines across the country.

Their passion for computers carried them into entrepreneurship before either had reached twenty. In 2007, still teenagers, Patrick and John launched their first company, Shuppa, from their family home. The idea was to build tools for online sellers, but the project quickly evolved when they were accepted into Y Combinator. There, they merged with another team to create Auctomatic, a software platform for eBay power-sellers. Within a year, the startup was acquired by the Canadian firm Live Current Media for about $5 million, making the Collisons millionaires at just 19 and 17.

The two brothers who had discovered the Internet through books were now shaping its future.

View of Dromineer and Lough Derg. Picture from Discover Lough Derg.

In 2011, Patrick and John Collison met Peter Thiel after a Y Combinator dinner. At the time, the brothers had been working on Stripe for about a year, and the PayPal founder shared lessons from building one of the world’s most renowned payment companies. Soon after, he invested in Stripe’s $2 million seed round, joined by Silicon Valley heavyweights such as Sequoia Capital, Andreessen Horowitz, SV Angel, Elon Musk, or Sam Altman.

Yet, just a few months earlier, things hadn’t been going so well for the two brothers. As they went from meeting to meeting with banks and card networks, the feedback was almost always the same: this will never work.

It’s in part thanks to books that the brothers found the willingness to persevere, and Charlie Munger’s Poor Charlie’s Almanack is perhaps the clearest influence here. John Collison read the book during the early days of Stripe and describes it as “an ode to thinking for yourself”, giving him the confidence to question received wisdom. The book’s emphasis on multidisciplinary thinking and multiple mental models — Munger’s hallmark — has been very useful to him in evaluating Stripe. By drawing on models from economics, psychology, physics, and history, he could choose the framework that fit the problem rather than forcing every problem through the same lens.

After their official launch in September 2011, growth came out quickly, with a surprising level of word of mouth for a financial infrastructure business. During this phase of early growth, another title particularly stood out: The Dream Machine, by M. Mitchell Waldrop. The book retrace the history of computing and the story of how J.C.R. Licklider imagined an “intergalactic computer network” long before the internet existed. Patrick Collison was so enthusiastic about this book that after finishing it, he went and bought a whole bunch of copies to give away to people at Stripe, quickly exhausting Amazon’s supply.

That reverence for reading translated into a distinctive writing culture inside Stripe. The brothers insisted on long-form memos and carefully argued proposals. “The first emails I saw from our CEO literally had footnotes,” recalled a former Head of Docs at Stripe in a blog post. “He structured his emails to be like research papers and put the peripheral information at the bottom so as not to detract from the core information.”

This commitment extended to Stripe’s meetings. While many companies default to slide decks, Stripe borrowed from Amazon’s practice of written narratives. In another blog post, a Stripe employee explains that a typical meeting begins with the organizer sharing a Google Doc. Cameras go off, and everyone spends 10–15 minutes reading silently, leaving comments in the document. Only then does discussion begin.

Writing forces you to slow down and structure your thinking in a way that speaking or unexamined reflection doesn’t. When ideas are only in your head, they can stay vague or contradictory. Putting thoughts into sentences requires choosing precise words, organizing them logically, and making connections explicit, which naturally sharpens reasoning.

The Dream Machine book, reissued by Stripe Press.

You can find books absolutely everywhere in Patrick Collison’s home: in the living room, the kitchen, the bedroom. He reads in the morning and at night, while eating alone, while waiting for a meeting like that day of 2005, and even while walking.

When choosing what to read, Patrick Collison looks at what has inspired the people he admires. He often favors older, time-tested works over the latest releases. He believes readers “should be much more biased towards older books” than they typically are. By letting books prove themselves over decades or centuries, he increases the odds of picking up enduring classics rather than fleeting trends.

Patrick Collison looks for the intersection between books that are worth reading and books that are enjoyable to read. Usually, he’d open a book in the middle, read a few pages, and ask himself: do I want to arrive here? If not, he sets it aside, though he keeps it visible, ready to catch his eye again later. If yes, he starts over from the beginning. And sometimes he abandons one book halfway only to jump into another that happens to be lying around. That’s why he loves physical books. Their presence invites serendipity. By his estimate, he starts one out of every two books he buys, and finishes one out of three. But that doesn’t stop him from reading one or two books per week.

Once immersed in a book, Patrick Collison annotates heavily. He writes notes in the margins, and keeps a quick index of page numbers at the end of the book — usually thirty or so — marking the passages he found most striking. He rarely rereads a book cover to cover, but often dips back into specific sections he’s annotated.

On rare occasions, if he has particularly enjoyed a book, he’ll take the time to summarize it in a Google Doc or an email to friends. The act of writing a summary, he says, helps with synthesis and recollection. That’s what he did, for example, with Joel Mokyr’s A Culture of Growth. He also shares thoughts on books from time to time on X. He recently tweeted that Fragile by Design from Calomiris and Haber was one of the best books he had read on financial services regulation.

Collection of Stripe Press books.

When you walked into Stripe’s former offices in San Francisco’s SoMa district, you would sit in a lobby where a coffee table was covered with reading material. You wouldn’t find the gossip magazines of a doctor’s waiting room, but instead engineering journals, issues of The Paris Review, novels, and the Twelve Tomorrows sci-fi anthology.

There was something deeply connected to the Collison brothers’ childhood in this room, and, more broadly, to Stripe’s culture: curiosity and openness. The two young Irishmen didn’t read only to learn about technology but to collect ideas from unexpected places, many of which later found their way into their work. This is likely why Charlie Munger’s concept of multidisciplinary thinking resonates so strongly with them.

To realize how large their horizon of lecture is, you just have to visit Patrick’s personal website. He shares a long list of 600 books he recommends, with a gigantic diversity. He often does the same on X. Want to read about business strategy? Find 7 Powers: The Foundations of Business Strategy. About progress? The Beginning Of Infinity. About science? Scientific Freedom. About venture capital? The Power Law. Or a novel? Try Middlemarch or Madame Bovary.

His little brother’s recommendations are just as eclectic. He often shares books he enjoyed reading on X, like The Art of Doing Science and Engineering by Richard W. Hamming, American Kingpin by Nick Bilton, or Financial Shenanigans by Howard Schilit.

This breadth of knowledge not only shaped Stripe’s culture, but also its mission. The brothers are deeply interested in the history of scientific progress and economic growth, and they actively apply those interests to Stripe’s vision. Their mission is about more than just making money movement easy. It’s about “increasing the GDP of the internet”. That mission reflects the intellectual curiosity they nurtured through years of reading across disciplines.

It also explains why Stripe invests in publishing. Through Stripe Press, the company republishes overlooked or out-of-print books that the Collisons consider valuable for understanding progress. You can buy Poor Charlie’s Almanack, The Dream Machine, but also The Origins of Efficiency or Where Is My Flying Car? The books cost between $20 and $40, hardly moving the needle on their $4 billion revenue in 2024, but they offer a rare glimpse into the company’s culture. And there’s also Works in Progress, a quarterly magazine and newsletter which highlights essays and research on economic growth, science, technology, and culture.

Ultimately, John and Patrick Collison’s passion for books serves not only the culture and vision of their company, but also its brand. After all, which other financial company sells books about flying cars?

What is striking about the Collisons is not only that they make time to read, but that reading is inseparable from their work. Books help them step back, think broadly, and shape Stripe’s culture, vision and brand. And when you notice how many successful leaders share the same habit, it’s hard to ignore the signal that reading helps. The challenge lies in turning inspiration into execution.

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Main sources and references:

I’ve drawn many insights about Patrick Collison’s reading habits from The Knowledge Project and The Tim Ferriss Show. Chris Atwood Zou and Dave Nunez in a Slab article shared valuable perspectives on Stripe’s culture. Wired, Startup Grind, and The Social Radars were also great sources of anecdotes. I recommend checking out Patrick Collison’s website and X account, as well as John Collison’s. Finally, thanks to Charles Delaville, Head of Communications at Stripe France, for reviewing this article.

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