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Every Thursday, join Jim O'Shaughnessy and his favorite people as they arm you with the tools & fresh perspectives required to upgrade your HumanOS and thrive in our messy, probabilistic world.
Visit our Substack at newsletter.osv.llc for full transcripts, highlights, weekly doses of timeless wisdom, and a bounty of other goodies designed to make you go, "Hmm that's interesting!"
Afleveringen
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Infinite Loops Classics | Mike Maples, Jr. — How To Become a Pattern-Breaking Founder
5 november 2026 · 1 uur 36 min
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! Lees meer
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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
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Tren Griffin - How To Write, Publish & Sell A Book In The AI Era (Ep. 334)
29 oktober 2026 · 1 uur 45 min
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. Lees meer
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: T…
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Spencer Greenberg - 106 Self-Help Books Distilled Into 12 Strategies (Ep. 333)
22 oktober 2026 · 1 uur 46 min
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. Lees meer
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 mi…
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Ed William - Writing A Biography That Reads Like Fiction (Ep. 332)
15 oktober 2026 · 1 uur 20 min
Pre-order No One's Coming to Save You today: https://infinitebooks.com/products/no-ones-coming-to-save-you Lees meer
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 Wi…
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Emma Camp - Why Gen Z Is Afraid of Rejection: Dating, Therapy Culture & Housing (Ep. 331)
8 oktober 2026 · 1 uur 21 min
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. Lees meer
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
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Julie Fredrickson - The Right to Compute: AI Agents, Nuclear Power & Human Data (Ep. 330)
1 oktober 2026 · 1 uur 28 min
Julie Fredrickson, Managing Partner of Chaotic Capital, rejoins Jim O'Shaughnessy on Infinite Loops to talk about Montana's Right to Compute Act, why verified human data may become one of the most valuable assets online, what nuclear power and the encryption wars teach about regulating AI, why chatbots keep recommending the same sunscreen, and what 2,089 days of daily public writing taught her about being wrong. It is her second Infinite Loops conversation, three years after Episode 181. Lees meer
Show Notes
Julie Fredrickson & Jim O'Shaughnessy
Julie Fredrickson: Managing Partner of Chaotic Capital, an early-stage venture fund, and a former founder in e-commerce and beauty. Chaotic Capital
Julie on X: Julie's preferred way to be reached. Follow Julie on X
Julie's daily writing: More than 2,000 consecutive days of public writing, started January 1, 2021. Read Julie's blog
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
Julie's Work & Projects
Montana's Right to Compute Act: The first state law protecting people's right to own and use computers and AI tools, which Julie advocated for. Read the Right to Compute Act
Valar Atomics: The small modular reactor company founded by Isaiah Taylor, where Julie invested. Valar Atomics
Julie's first Infinite Loops episode: Episode 181, "Circumstances change. Humanity doesn't. Plan accordingly." Watch Episode 181
Books & Ideas Mentioned
The Beginning of Infinity by David Deutsch: Jim's reference for why no one in 1900 could have predicted the internet. The Beginning of Infinity
Carlota Perez: The economist whose work on technology booms and build-outs shapes Julie's view that AI is still in its invention phase. Carlota Perez
Rainbows End by Vernor Vinge: The novel Julie cites for a future where people ea…
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Derek Sivers - Living Many Lives: Parenting, Moving Countries & AI (Ep. 329)
24 september 2026 · 1 uur 44 min
Derek Sivers, author, entrepreneur, TED speaker, and founder of CD Baby, joins Jim O'Shaughnessy on Infinite Loops to talk about parenting a teenager who is ready to leave home, why he moves countries on purpose and plans to live in Bangalore and Shanghai next, the certainty slider, and how AI can make you less dependent on big tech, not more. It is his first podcast after more than a year of saying no to every request. Lees meer
Show Notes
Derek Sivers & Jim O'Shaughnessy
Derek Sivers: Author, entrepreneur, and TED speaker, and founder of CD Baby, once the largest seller of independent music online. Derek's website
Derek on X: Where Derek shares his writing. Follow Derek on X
Derek's TED talks: Including "How to Start a Movement," his most popular talk. Watch Derek's talks
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
Derek's Books & Projects
Useful Not True: Derek's book on skepticism and choosing beliefs because they are useful, not because they are true. Useful Not True
How to Live: 27 conflicting answers on how to live, which Derek calls his masterpiece. How to Live
Hell Yeah or No: Simple mental models for deciding what's worth doing. Hell Yeah or No
Anything You Want: Derek's bestselling book of 40 lessons from starting, building, and selling CD Baby. Anything You Want
Tech Independence: Step-by-step instructions and a setup script for running your own server and email instead of depending on big tech. Tech Independence
Books & Ideas Mentioned
Personal Development for Smart People by Steve Pavlina: The book whose idea about seeking surprise sent Derek around the world. Derek's notes
China's World View by David Daokui Li: Derek's pick for understanding the Chinese government's point of view. Derek's notes
Maverick by Ricardo Seml…
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Brent Seales - How AI Is Reading the Only Library That Survived Antiquity (Ep. 328)
17 september 2026 · 55 min
Dr. Brent Seales, computer scientist at the University of Kentucky and co-founder of the Vesuvius Challenge, joins guest host Nick Tawil on Infinite Loops to explain how synchrotron X-rays and machine learning are making unopenable ancient scrolls readable, and why the work has now shifted from engineering to reading. This summer in Naples, his team presented results from three sealed Herculaneum scrolls, including the first read end to end. Lees meer
Show Notes
Brent Seales & Nick Tawil
Dr. Brent Seales: Stanley and Karen Pigman Chair of Heritage Science at the University of Kentucky and co-founder of the Vesuvius Challenge. Brent Seales at the University of Kentucky
Vesuvius Challenge: The open competition Brent co-founded with Nat Friedman and Daniel Gross to read the carbonized Herculaneum scrolls. Vesuvius Challenge
The June 2026 breakthrough: The announcement in Naples of new texts, titles, and authors recovered from the scrolls. The day the Herculaneum scrolls began speaking again
Nick Tawil: Guest host and head of Infinite Films. Connect with Nick
The Scrolls & the Discoveries
The Herculaneum library: Roughly 1,800 scrolls carbonized by Mount Vesuvius in 79 AD, the only library from antiquity that survived. Vesuvius Challenge: the scrolls
Philodemus, On Gods, Book 8: A title and author read from a sealed scroll, establishing that the work ran to at least eight books. CNN on the discovery
The En-Gedi scroll: The burned Torah scroll Brent's team read without opening, containing one of the oldest known copies of the first two chapters of Leviticus in the canonical Masoretic text. Vesuvius Challenge on En-Gedi
The $1 million prize: The open competition to fully unroll and read one of the remaining sealed scrolls. Current prizes
Films & Coverage Mentioned
The Vesuvius Challenge: The upcoming documentary from Infinite Films and Scott Free, in partnership with Calliope Pictures, narrated by Guy Pearce. Deadline announcement
Secrets of the Dead: The Herculaneum…
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Ryan Resch - How Data Changed the NBA and What AI Changes Next (Ep. 327)
10 september 2026 · 1 uur 43 min
Ryan Resch, former Assistant General Manager and VP of Basketball Operations for the Phoenix Suns, joins guest host Jimmy Soni on Infinite Loops to explore what happens to competitive advantage when every team has the same data, and why the real edge comes from the questions you ask of it. Ryan traces his path from a cold email to Baylor coach Scott Drew to nearly a decade in the Suns front office and his current work leading data and AI in private equity. Lees meer
Show Notes
Ryan Resch & Jimmy Soni
Ryan Resch on LinkedIn: Former Suns Assistant GM and VP of Basketball Operations, now leading data and AI at 1949 Capital Partners. Connect with Ryan
Beyond the Dashboard: Ryan's Harvard Business School interview with Boris Groysberg on optical tracking, dashboards, and AI. Read the interview
Shore Capital Partners: The private equity firm founded by Justin Ishbia, where Ryan helped roll out AI tools. Shore Capital Partners
Jimmy Soni on X: Guest host, bestselling author, and editor-in-chief of Infinite Books. Connect with Jimmy
Teams, Leaders & Data Discussed
James Jones: The 2020-21 NBA Executive of the Year, whose Suns rebuild started with raising the floor. Executive of the Year
Scott Drew: The Baylor head coach who answered Ryan's cold email and later had him build lineup data. Scott Drew at Baylor
SportVU: The camera system that brought optical tracking to every NBA arena in 2013-14. SportVU and the NBA
Second Spectrum: The machine learning platform that turned tracking data into tagged plays and dashboards teams across the league use. Second Spectrum and the NBA
Hawk-Eye: Sony's 3D tracking system, used across the NBA since 2023-24. Hawk-Eye and the NBA
Books, Shows & AI Tools Mentioned
Moneyball by Michael Lewis: The 2003 book on the Oakland A's that frames how analytics moved from baseball into basketball. Moneyball
Hyperion by Dan Simmons: The first book in the sci-fi series Ryan is reading, and a window into how earlier writers imagined AI. Hyperion
Th…
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Brian Chau - How AI is Reinventing Investigative Journalism (Ep. 326)
3 september 2026 · 1 uur 46 min
Brian Chau, founder of Effort News, joins Infinite Loops to explore how AI could fundamentally reshape investigative journalism—not by writing articles, but by searching, analyzing, and connecting millions of legal, financial, and government records that humans could never examine manually. Lees meer
Show Notes
Brian Chau & Effort News
Effort News — Brian Chau's document-led investigative journalism publication, using AI to search and analyze large datasets while keeping the reporting and final writing human-reviewed. Effort News
About Effort News — More on Brian's approach to AI-assisted investigative reporting and the publication's editorial principles. About Effort News
Effort's Null Results — Investigations where Effort searched the available evidence but found no newsworthy result. Null Results
Brian Chau on X — @brianchau57. Follow Brian on X
Investigations Discussed
The $1.2B Refugee Services Program that Funds Pro-Asylum Religious Groups — Effort's investigation into federal refugee-resettlement grants and the organizations receiving them. Read the investigation
The 19th-Century Family Fortunes Funding Degrowth — Effort's investigation tracing funding for Partners for a New Economy through donor-side disclosures and the Swiss Philanthropy Foundation. Read the investigation
Partners for a New Economy (P4NE) — The philanthropic fund discussed in Brian's explanation of tracing obscured donor funding. P4NE
Swiss Philanthropy Foundation — The organization that hosts P4NE's pooled philanthropic fund. Swiss Philanthropy Foundation on P4NE
How to Go Viral on the New X Algorithm — Effort's analysis of X's open-source recommendation algorithm, which Jim references near the end of the conversation. Read the investigation
Freedom Fuel Network — Brian discusses Effort's then-upcoming investigation into the mysterious network of discounted gas stations in Pennsylvania and New Jersey. Effort has since published its findings, Who Supplies Freedom Fuel?, on its site. Eff…
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- Categorieën
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- Elke week
- Lengte
- Meestal 1 uur 35 min
- Afleveringen
- 348
- Laatste aflevering
- 5 november 2026
- Eerste aflevering
- 25 november 2019
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