Infinite Loops

This week, we're re-upping one of my favorite episodes from the archives: my chat with Mike Maples, Jr., from September 2024. Normal scheduling will resume next week. Enjoy!
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Mike Maples, Jr., co-founding partner of the VC firm Floodgate, is the veteran seed investor behind some of the 21st century's great success stories, including Twitter, Twitch, and Applied Intuition.
His book, Pattern Breakers (co-authored with Peter Ziebelman), articulates a new model of foundership, one built on the simple premise that transformative startups upend rather than improve current practices.
I had a blast quizzing Mike on the nuts and bolts of pattern-breaking foundership, from finding true believers to waging asymmetric war on the status quo.
Important Links:
Pattern Breakers: Why Some Start-Ups Change the Future; by Mike Maples, Jr & Peter Ziebelman
Twitter
Substack (Starting Greatness)
Floodgate
LinkedIn
Show Notes:
Seagull mode: an unexpected founder paradigm
How to wage asymmetric war on the present
Evading the comparison trap
Finding your people: how to build a movement
Why we should continually seek the truth
The customer isn't always right, but the ones living in the future are
Why disagreeableness is undervalued
How to fix a pitch Frankendeck
Don't use jargon as a substitute for clear thinking
How to find the true believers
How to live in the future
How founders are like trainspotters
Why wanting to be a founder is a bad reason to start a company
Reading habits of a pattern-breaker
The unreliability of memory
Mike as emperor of the world
MORE!
Books Mentioned:
Jonathan Livingston Seagull: A story; by Richard Bach
The Genius of the Beast: A Radical Re-Vision of Capitalism; by Howard Bloom
The Beginning of Infinity: Explanations that Transform The World; by David Deutsch
What Works on Wall Street; by Jim O'Shaughnessy
Poor Charlie's Almanack: The Essential Wit and Wisdom of Charles T. Munger; by Charles T. Munger

Tren Griffin, author of Charlie Munger: The Complete Investor and the 25iq blog, joins Jim O'Shaughnessy on Infinite Loops to talk about why writing a book is rarely about money, how AI is reshaping writing and publishing, why every author is really starting a business, how to build a book in public, the Charlie Munger lesson that changed his life during the dot-com boom, whether serious reading is really dying, and how to find a passion worth following.
Show Notes
Tren Griffin & Jim O'Shaughnessy
Tren Griffin: Investor, writer, and author of the 25iq blog. Read 25iq

Charlie Munger: The Complete Investor: Tren's book on how Munger approached investing and life. Charlie Munger: The Complete Investor

Tren on X: Follow Tren on X

Infinite Books: Jim's publishing company. Infinite Books

Tren's earlier conversation: Welcome to the Tren-verse, Ep. 86. Watch

Jim O'Shaughnessy: Host of Infinite Loops, founder and CEO of O'Shaughnessy Ventures, and author of the New York Times bestseller What Works on Wall Street. Follow Jim on X

Full transcripts: Transcripts and highlights from every Infinite Loops conversation. OSV newsletter

Books & Ideas Mentioned
The Psychology of Money by Morgan Housel: Tren's example of how stories sell nonfiction. The Psychology of Money

Runnin' Down a Dream by Bill Gurley: The book Tren recommends on turning passions into a career. Runnin' Down a Dream

Kelly criterion: The bet-sizing formula Tren calls one of the hardest ideas to explain simply. Kelly criterion

Why Greatness Cannot Be Planned by Kenneth Stanley and Joel Lehman: Jim's case for taking unexpected opportunities seriously. Kenneth Stanley

1,000 True Fans by Kevin Kelly: The essay behind Tren's advice to build a community of super fans. 1,000 True Fans

Duncan Watts on social influence: Why bestsellers emerge from people copying what others buy. Duncan J. Watts

Mimetic desire: René Girard's idea that we want what others want. Mimetic theory

Influence by Robert Cialdini: The reciprocity principle behind Jim's warning about manipulation. Influence

Reflexivity: George Soros's idea from The Alchemy of Finance, which shaped Tren's thinking on feedback loops. Reflexivity

Benoit Mandelbrot: Whose The (Mis)Behavior of Markets Jim credits with shaping the models he built to pick stocks. Benoit Mandelbrot

Gödel, Escher, Bach by Douglas Hofstadter: Jim's example of a hard book that AI could open up to more readers. Gödel, Escher, Bach

Clarke's third law: "Sufficiently advanced technology is indistinguishable from magic." Clarke's three laws

Cabo Wabo: Sammy Hagar's tequila, Tren's example of a founder bringing a ready-made community to a product. Cabo Wabo

Menlo Ventures consumer AI survey (2025): About 3% of AI users pay, in line with Tren's point that most people use AI for free. Read the release

Spencer Greenberg, mathematician, founder of Clearer Thinking, and co-author of The 12 Levers, joins Jim O'Shaughnessy on Infinite Loops to talk about which self-help techniques hold up to evidence, why memory works like autocomplete, how exposure therapy cured his lifelong social anxiety, why the law of attraction can backfire, how to design hiring interviews that predict performance, and what his team found replicating new studies from top psychology journals.
Show Notes
Spencer Greenberg & Jim O'Shaughnessy
Spencer Greenberg: Mathematician and entrepreneur, founder of ClearerThinking.org and Spark Wave, and host of the Clearer Thinking podcast. Clearer Thinking

The 12 Levers: Spencer and Jeremy Stevenson's evidence-based toolkit for improving your life. The 12 Levers

Clearer Thinking podcast: Spencer's interview show, where Jim has been a guest. Listen

Transparent Replications: Spencer's project that randomly picks and re-runs new studies from top psychology journals. Transparent Replications

Importance hacking: Spencer's essay on the problem his replications uncovered. Read the essay

Jim O'Shaughnessy: Host of Infinite Loops, founder and CEO of O'Shaughnessy Ventures, and author of the New York Times bestseller What Works on Wall Street. Follow Jim on X

Full transcripts: Transcripts and highlights from every Infinite Loops conversation. OSV newsletter

Books & Ideas Mentioned
Reality tunnels: Robert Anton Wilson's idea that everyone perceives a different version of reality. Reality tunnel

The Challenger memory study: Research showing how far people's memories of a major event drift over time. Flashbulb memory

Spaced repetition: Spencer's recommended method for remembering what matters. Spaced repetition

My Dinner with Andre: The film that shaped how Jim designed Infinite Loops. My Dinner with Andre

Behavioral activation: The evidence-based depression technique Spencer describes. Behavioral activation

Daniel Kahneman: Whose work for the Israeli military showed which interview methods actually predict performance. Daniel Kahneman

Pre-mortem: The technique of imagining a plan has failed and working out why. Pre-mortem

Replication crisis: The finding that many published psychology results don't hold up when re-run. Replication crisis

John Sarno: The NYU physician whose work on the mind's role in chronic pain Jim credits with curing his frozen neck. John E. Sarno

Molecules of Emotion by Candace Pert: Jim's reference on how emotions show up physically in the body. Candace Pert

Mirror box therapy: The phantom limb treatment Spencer uses to show the brain can reinterpret a pain signal. Mirror box

Pre-order No One's Coming to Save You today: https://infinitebooks.com/products/no-ones-coming-to-save-you
David Rhoiney was five when his father walked out, forcing David to become the "man of the house."
Compton, Oakland, Long Beach: no matter where they turned, fear and hunger waited. Long nights in the homeless shelter. Drive-by shootings. Strangers in overalls dragging his mother away. As his world collapsed, David lost hope. No one was coming to save him.
But he could save himself.
When basketball threw him a lifeline, David grabbed it. So began an unlikely journey, one that carried him from living in a Volkswagen Jetta onto the courts of Division I, through the halls of the Naval Academy, into the corridors of national intelligence, and under the watchtowers of Guantánamo Bay. At last, scalpel in hand, David reached the operating room, where he could become the man his family needed.
Ed William, a former lawyer, spent several days interviewing David and spoke to dozens of people from his life. The result is Ed's first book, No One's Coming to Save You: The Escape of David Rhoiney, out from Infinite Books on 8 December and now available for pre-order: https://infinitebooks.com/products/no-ones-coming-to-save-you
"A powerful and deeply moving account of a boy forced to grow up too soon and the man he fought to become."
—Rob Henderson, bestselling author of Troubled
Ed joins Jim to discuss:
The time David was forced to fight a schoolyard bully in front of his family.

David's unusual experience of the Rodney King riots.

The note David wrote to God every night.

The English teacher who changed David's life in one hour. 

The prep school coach who cancelled David's credit cards. 

How a five-foot-three kid ended up playing Division I basketball. 

David as a role model for young men.

The guilt underpinning David's success.  

The single word that describes David. 

Why Ed's interview plan fell apart in the first 5 minutes. 

Why Ed was inspired by Into the Wild and Raiders of the Lost Ark.

How Ed captured David's voice.

Much more!




Show Notes
Ed William & Jim O'Shaughnessy
Ed William: Writer, editor, former lawyer and author of No One's Coming to Save You. Read Rough Cuts

The book: No One's Coming to Save You: The Escape of David Rhoiney, out December 8, 2026. Pre-order

Infinite Books: The publishing imprint behind the book. Infinite Books

Jim O'Shaughnessy: Host of Infinite Loops, founder and CEO of O'Shaughnessy Ventures, and author of the New York Times bestseller What Works on Wall Street. Follow Jim on X

Full transcripts: Transcripts and highlights from every Infinite Loops conversation. OSV newsletter

Books, Films & Ideas Mentioned
Into the Wild: The film Ed compares to the Houston chapter, where David almost stops to rest. Into the Wild

Raiders of the Lost Ark: Spielberg's "no boring bits" approach that set the book's pace. Raiders of the Lost Ark

Mad Max: Fury Road: Ed's model for a story that never stops moving. Mad Max: Fury Road

The Pursuit of Happyness and Good Will Hunting: The stories Ed sees as the book's closest film parallels. The Pursuit of Happyness / Good Will Hunting

What Works on Wall Street: Jim's book, which David challenged him on in their first conversations. What Works on Wall Street

Behaviorism: The mid-century "give me a baby and I'll make it anything" school Jim cites in the nature-versus-nurture debate. Behaviorism

Emma Camp, senior newsletter editor at The Wall Street Journal's Free Expression, joins Jim O'Shaughnessy on Infinite Loops to talk about why Gen Z is dating less and spending more time alone, how therapy culture and helicopter parenting can turn growing pains into permanent labels, why the fix for the housing shortage is more housing, and why she invites everyone she's met to every party. She also previews her forthcoming essay collection on Gen Z and risk aversion.
Show Notes
Emma Camp & Jim O'Shaughnessy
Emma Camp: Senior newsletter editor at Free Expression, The Wall Street Journal's opinion newsletter, and former Reason magazine editor. Read Free Expression

Emma's breakout essay: Her reflection on the 2022 New York Times op-ed that started her career. After My Big Break

Jim O'Shaughnessy: Host of Infinite Loops, founder and CEO of O'Shaughnessy Ventures, and author of the New York Times bestseller What Works on Wall Street. Follow Jim on X

Full transcripts: Transcripts and highlights from every Infinite Loops conversation. OSV newsletter

Books & Ideas Mentioned
The Grim Old Days by Chelsea Follett: Emma's reference for how hard life was for the average person before modern markets. Chelsea Follett

The Genius of the Beast by Howard Bloom: Jim's reference for what capitalism achieved that earlier systems couldn't. The Genius of the Beast

Jefferson Literary and Debating Society: The University of Virginia society where Emma threw a party every Friday. Jefferson Society

Partiful: The app Emma uses to invite everyone to every party. Partiful

Sally Rooney: The novelist Emma writes about in her essays on modern relationships. Sally Rooney

Attachment theory: Emma's frame for why a secure marriage lets her take more social risks. Attachment theory

NAR 2025 Profile of Home Buyers and Sellers: The data on first-time buyers reaching a record median age of 40. Coverage