Podcast
John Collison's book list: the books mentioned on Cheeky Pint
Books from the latest episodes
Most recommended on Cheeky Pint
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The Hitchhiker's Guide to the Galaxy
The Hitchhiker's Guide to the Galaxy by Douglas Adams was referenced on Cheeky Pint in two separate episodes. In April 2026, Mati Staniszewski mentioned the book's Babel fish when discussing universal translation and voice AI. In November 2025, the host used a reference from the book to metaphorically describe unsearchable, opaque databases used by hospital systems.
Discussed“From The Hitchhiker's Guide to the Galaxy, this version of the Babel fish. That you can actually understand the world.”
Where to get it
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Flash Boys
On Cheeky Pint, guest Vlad Tenev discussed Michael Lewis's book Flash Boys in August 2025. Tenev noted that the book's release coincided with the initial waitlist announcement for Robinhood in 2013 and referenced online commentary surrounding the book to illustrate public sentiment regarding high-frequency trading.
Discussed“When we announced Robinhood, our initial waitlist in 2013, there was this book that came out, "Flash Boys." And it was basically coincident with the announcement of Robinhood—the Michael Lewis book.”
Where to get it
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Cable Cowboy
During the Cheeky Pint episode published on 2025-10-06 and titled Tobi Lütke is still captivated by internet commerce, 20 years later, guest Tobi Lütke recommended Cable Cowboy by Mark Robichaux. Lütke praised the publication enthusiastically while discussing John Malone and Liberty Media, describing it as one of the best and most engaging books on the subject.
Recommended“Like, I mean, "Cable Cowboy" is already one of the best. It was a great book. It's such a great book, and then, like—”
Where to get it
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Getting Things Done
On Cheeky Pint, Ben Thompson brought up Getting Things Done by David Allen to illustrate his personal productivity habits and system management. He noted that even if a reader does not adopt the exact system outlined by the author, the book itself is exceptionally useful.
Recommended“Like, great book Getting Things Done. Even if you don't use the system, the book is really good.”
Where to get it
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Red Plenty
On Cheeky Pint, John Collison discussed Francis Spufford's book Red Plenty during an October 2025 episode. He recommended the work as a fabulous, fictionalized account used to explore the history of Soviet industrialization and economic growth relative to the West.
Recommended“There's a fabulous book called "Red Plenty" by Francis Spufford that is kind of a fictionalized account of this.”
Where to get it
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The Essays of Warren Buffett
During an episode of Cheeky Pint titled Dan Sundheim of D1 Capital on the art of public market investing, released on October 22, 2025, the host recommended The Essays of Warren Buffett by Warren Buffett and Lawrence A. Cunningham. The host stated that Lawrence A. Cunningham's book, which compiles Buffett's letters to eliminate repetition, was his favorite and well worth reading.
Recommended“Obviously, the Buffett stuff is very worth reading, and there's the Cunningham book that takes all the letters and smushes them together because there's a lot of repetition. That's my favorite book.”
Where to get it
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The Origins of Efficiency
On the Cheeky Pint episode titled "Casey Handmer of Terraform Industries on solar maximalism, hard tech, and reclai," published on October 28, 2025, John Collison recommended Brian Potter's book The Origins of Efficiency. The host highlighted that the work was published by Stripe Press and explained that the author breaks down the precise mechanical and historical processes of how industrial progress happens.
Recommended“In Stripe Press's newest book, "The Origins of Efficiency", author Brian Potter breaks down precisely how that progress happens.”
Where to get it
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12 Angry Men
In an episode of Cheeky Pint released on February 17, 2026, featuring Ramp founder Eric Glyman, one of the hosts brought up the film 12 Angry Men. The host used the movie to illustrate how additional context is necessary to reach moral conclusions, drawing a parallel between the story's shifting evidence and the evaluation of employee corporate expense policies.
Discussed“What was the name of the movie? "12 Angry Men," I think it was where, as you're watching the film, you get some level of detail and someone seems very guilty. It's a dead shut case. And as more evidence emerges, you realize actually, this may be different. And you need more context in order to arrive at maybe a”
Where to get it
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2001, a Space Odyssey
On a November 18, 2025, episode of Cheeky Pint, the host referenced the film adaptation of 2001, a Space Odyssey by Arthur C. Clarke and Stanley Kubrick to highlight how early the 1960s vision for voice-activated, tool-using artificial intelligence was compared to actual technological readiness.
Discussed“Like the movie "2001: A Space Odyssey," which is in the '60s, like that was a voice activated AI with tool use, you know, capabilities.”
Where to get it
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Apple in China
On an episode of Cheeky Pint from November 2025, the host mentioned Patrick McGee's book Apple in China. The host brought up the book while discussing product bundling decisions made by tech companies, noting how decisions inside Apple often originated from seemingly random choices.
Discussed“My understanding reading the "Apple in China" book is it was like a totally random decision that someone just made it, you know, one day.”
Where to get it
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Boyd
On an episode of Cheeky Pint titled Garrett Langley of Flock Safety on building technology to solve crime, released on March 5, 2026, John Collison discussed the book Boyd by Robert Coram. Collison noted that he had read the biography only recently and observed that it is frequently discussed in Silicon Valley circles, specifically in relation to John Boyd and his famous OODA Loop concept within military and strategic contexts.
Discussed“the Boyd book by Robert Coram, which I only read recently, but it's like one of those kind of Silicon Valley, and everyone talks about it, and everyone talks about him in the context of his OODA Loop.”
Where to get it
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Cadillac Desert
During an episode of Cheeky Pint released on October 28, 2025, Casey Handmer and the host discussed the Bureau of Reclamation and water management infrastructure in the American West. In that context, Handmer brought up Marc Reisner's book Cadillac Desert, noting that the text goes into extensive detail on the subject and praising it as a great book.
Discussed“If you've read "Cadillac Desert", it goes into some detail here. That's a great book.”
Where to get it
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Consider Phlebas
On Cheeky Pint episode Marc Andreessen and Charlie Songhurst on the past, present, and future of Silico released on 2025-10-01, John Collison brought up Consider Phlebas by Iain M. Banks while discussing science fiction depictions of advanced societies involving artificial intelligence.
Discussed“Have you read ever, Iain M. Banks, the science fiction author? The Culture Suits.”
Where to get it
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Design Patterns
During an episode of Cheeky Pint titled Tobi Lütke is still captivated by internet commerce, 20 years later, released on October 6, 2025, John Collison brought up the book Design Patterns by Erich Gamma, Richard Helm, Ralph Johnson, and John Vlissides. Collison referenced the programming text editors book to illustrate software craftsmanship, noting that Erich Gamma dedicated his career to building multiple editors.
Discussed“VS Code is Erich Gamma's fourth editor, right? It's like he spent his entire life making these things. That's craftsmanship. Yeah, it's like he wrote the "Design Patterns" book that many of us read at some point literally about programming text editors, right?”
Where to get it
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Elon Musk
On the October 1, 2025, episode of Cheeky Pint titled Marc Andreessen and Charlie Songhurst on the past, present, and future of Silico, John Collison discussed Walter Isaacson's biography Elon Musk. Collison noted that although the recent book received a mixed reception, he found it pretty useful for anyone wanting to study the management methods of Elon Musk.
Discussed“And, by the way, I thought the Walter Isaacson book, it got a mixed reception, but I thought if you want to study the Elon method a bit, it was actually pretty useful for that, the recent biography.”
Where to get it
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Emma
On the March 24, 2026 episode of Cheeky Pint, guest Dmitri Dolgov of Waymo appeared on the show to discuss the twenty-year journey toward fully autonomous vehicles. During the interview, Dolgov mentioned Jane Austen's novel Emma only to note that his team had published a research paper sharing the same title to illustrate fine-tuning Vision-Language Models for predicting driving trajectories.
Discussed“In fact, a while ago, we published a paper called EMMA, that did exactly that.”
Where to get it
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Fragile by Design
On Cheeky Pint, in an episode titled Tobi Lütke is still captivated by internet commerce, 20 years later released on October 6, 2025, John Collison discussed the book Fragile by Design by Charles W. Calomiris and Stephen Haber. Collison talked about the book, which examines the history of various banking systems around the world, and highlighted that the chapter focusing on Canada was particularly good.
Discussed“Did we recommend the Calomiris book to you? "Fragile by Design," which is a history of various countries' banking systems. I'm literally just reading it. Oh, you are? That's so— And the Canada chapter is particularly good.”
Where to get it
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Oracle Application Express 3.2 - The Essentials and More
In the Cheeky Pint episode titled "Satya Nadella describes how lessons from Microsoft’s history apply to today’s bo," released on November 18, 2025, the host used a reference to Oracle Application Express 3.2 - The Essentials and More by Arie Geller and Matthew Lyon within a broader company history discussion. John cited related Oracle literature while talking about Larry Ellison pitching enterprise data solutions during executive briefings in Japan in the 1990s.
Discussed“My favorite example of this is I read like the book "Softwar" on, you know, the history of Oracle, and it talks about Larry Ellison doing EBCs, I think they're talking about one in Japan, in the 1990s.”
Where to get it
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Pioneering Portfolio Management
On an episode of Cheeky Pint titled Marc Andreessen and Charlie Songhurst on the past, present, and future of Silico, released on October 1, 2025, Marc Andreessen brought up the book Pioneering Portfolio Management by David F. Swensen. Andreessen referenced Swensen, whom he described as the smartest portfolio manager for liquid portfolios, to explain how investors must evaluate venture capital and long-horizon assets.
Discussed“David Swensen who was considered to be the smartest portfolio manager for liquid portfolios, wrote a book where he goes through the following, and he talked about this a lot, which basically, is for something like venture, you really got to look on it.”
Where to get it
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Rise of the Machines
On the Cheeky Pint episode Marc Andreessen and Charlie Songhurst on the past, present, and future of Silico, published on 2025-10-01, guest John Collison mentioned Rise of the Machines by Thomas Rid. Collison brought up the text to examine the prehistory of artificial intelligence, noting that it details early debates regarding cybernetics that took place in the 1930s.
Discussed“There's a book called "Rise of the Machines" that has the prehistory of AI, and, I believe I remember correctly, there were actually debates about this in the 1930s.”
Where to get it
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Softwar
During the Cheeky Pint episode titled "Satya Nadella describes how lessons from Microsoft’s history apply to today’s bo," released on November 18, 2025, the host brought up Matthew Symonds' book Softwar. John cited the book as his favorite example to illustrate a historical business lesson about Larry Ellison. He used the text to describe how Ellison pitched the idea of centralizing all company data into one repository while conducting EBCs in Japan during the 1990s.
Discussed“My favorite example of this is I read like the book "Softwar" on, you know, the history of Oracle, and it talks about Larry Ellison doing EBCs, I think they're talking about one in Japan, in the 1990s.”
Where to get it
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The Digital Silk Road
On an episode of Cheeky Pint released on March 5, 2026, guest Garrett Langley brought up The Digital Silk Road by Jonathan E. Hillman. Langley used the book to illustrate how China successfully utilizes infrastructure deployments and connectivity to exert ownership and influence over developing countries in Africa.
Discussed“There's a great book on this topic. If you look at what China was able to do in Africa with their infrastructure deployments on connectivity, they own those countries.”
Where to get it
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The End of Accounting and the Path Forward for Investors and Managers
During an episode of Cheeky Pint titled Ambrook CEO Mackenzie Burnett on American agriculture, rural resilience, and car, released on September 17, 2025, John Collison brought up the book The End of Accounting and the Path Forward for Investors and Managers by Baruch Lev and Feng Gu. Collison highlighted the work as one of his favorite accounting books, noting its critique that GAAP is poorly suited to the modern era.
Discussed“One of my favorite books about accounting is "The End of Accounting," which talks about how GAAP is basically poorly suited to this day and age. And one of the things it points out is that accounting is trying to do many jobs, right?”
Where to get it
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The Innovator's Dilemma
On the August 20, 2025 episode of Cheeky Pint, guest Brian Armstrong brought up Clayton Christensen's book The Innovator's Dilemma. Armstrong referenced the book to explain why traditional banks struggle to embrace cryptocurrency due to the difficulties organizations face when trying to move away from systems that make them massive profits.
Discussed“It's a little bit of that Innovator's Dilemma type thing—Clay Christensen— where culturally it's so hard to get an organization where they're making tons of money off the traditional system.”
Where to get it
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The Revolt of the Public and the Crisis of Authority in the New Millennium
On an episode of Cheeky Pint released on October 1, 2025, featuring Marc Andreessen and Charlie Songhurst, Andreessen discussed The Revolt of the Public and the Crisis of Authority in the New Millennium by Martin Gurri. Andreessen stated that the author really nailed the subject matter, using the book to explain the decentralizing effect that true transparency and free speech have on centralized institutions.
Discussed“I think Martin Gurri, the guy who has published this book. I think he really nailed it...”
Where to get it
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When Genius Failed
On Cheeky Pint on October 1, 2025, featuring Marc Andreessen and Charlie Songhurst, Marc Andreessen brought up Roger Lowenstein's book When Genius Failed. Andreessen shared that he had read the book recently, praising it as a fantastic work while discussing Long-Term Capital Management and the 1998 financial crisis.
Discussed“I read that book recently. It was really good. It's a fantastic book.”
Where to get it
Guests who recommended books
- Marc Andreessen (2)
- Vlad Tenev (2)
- Mati Staniszewski (1)
- Dmitri Dolgov (1)
- Garrett Langley (1)
- Ben Thompson (1)
- Tobi Lütke (1)
- Brian Armstrong (1)
Latest mentions
“From The Hitchhiker's Guide to the Galaxy, this version of the Babel fish. That you can actually understand the world.”
“In fact, a while ago, we published a paper called EMMA, that did exactly that.”
“There's a great book on this topic. If you look at what China was able to do in Africa with their infrastructure deployments on connectivity, they own those countries.”
“the Boyd book by Robert Coram, which I only read recently, but it's like one of those kind of Silicon Valley, and everyone talks about it, and everyone talks about him in the context of his OODA Loop.”
“What was the name of the movie? "12 Angry Men," I think it was where, as you're watching the film, you get some level of detail and someone seems very guilty. It's a dead shut case. And as more evidence emerges, you realize actually, this may be different. And you need more context in order to arrive at maybe a”
“Like, great book Getting Things Done. Even if you don't use the system, the book is really good.”
“My favorite example of this is I read like the book "Softwar" on, you know, the history of Oracle, and it talks about Larry Ellison doing EBCs, I think they're talking about one in Japan, in the 1990s.”
“My favorite example of this is I read like the book "Softwar" on, you know, the history of Oracle, and it talks about Larry Ellison doing EBCs, I think they're talking about one in Japan, in the 1990s.”
“Like the movie "2001: A Space Odyssey," which is in the '60s, like that was a voice activated AI with tool use, you know, capabilities.”
“My understanding reading the "Apple in China" book is it was like a totally random decision that someone just made it, you know, one day.”
“There's a fabulous book called "Red Plenty" by Francis Spufford that is kind of a fictionalized account of this.”
“In Stripe Press's newest book, "The Origins of Efficiency", author Brian Potter breaks down precisely how that progress happens.”
“If you've read "Cadillac Desert", it goes into some detail here. That's a great book.”
“Obviously, the Buffett stuff is very worth reading, and there's the Cunningham book that takes all the letters and smushes them together because there's a lot of repetition. That's my favorite book.”
“VS Code is Erich Gamma's fourth editor, right? It's like he spent his entire life making these things. That's craftsmanship. Yeah, it's like he wrote the "Design Patterns" book that many of us read at some point literally about programming text editors, right?”
“Did we recommend the Calomiris book to you? "Fragile by Design," which is a history of various countries' banking systems. I'm literally just reading it. Oh, you are? That's so— And the Canada chapter is particularly good.”
“Like, I mean, "Cable Cowboy" is already one of the best. It was a great book. It's such a great book, and then, like—”
“I read that book recently. It was really good. It's a fantastic book.”
“David Swensen who was considered to be the smartest portfolio manager for liquid portfolios, wrote a book where he goes through the following, and he talked about this a lot, which basically, is for something like venture, you really got to look on it.”
“There's a book called "Rise of the Machines" that has the prehistory of AI, and, I believe I remember correctly, there were actually debates about this in the 1930s.”
Episodes
Link to this list from your show notes
Host or produce Cheeky Pint? Give your listeners every book mentioned on the show, with the episode and the minute it came up. New episodes are added as they come out.
