Jim O'Shaughnessy
Infinite Loops
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!"
Author
Jim O'Shaughnessy
Category
Podcast website
Latest episode
Jul 9, 2026
Where to listen?
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Episodes
Dan Runcie – The Business of Hip-Hop & Music (EP.30) 14.01.2021 1:05:05
In this episode of Infinite Loops we spoke with Dan Runcie, author of the popular newsletter Trapital, which focuses on hip-hop business trends. Our conversation covers: Apple vs. Spotify Music as an investment asset Unique revenue streams for innovative artists The economics of hip-hop Opportunities for artists in Tiktok and other new apps And MUCH more Follow Dan ( https://twitter.com/RuncieDan...
Brian Roemmele – The Intelligence Amplifier (EP.29) 31.12.2020 1:42:46
In this episode of Infinite Loops we spoke with Brian Roemmele, aka "The Voice Expert". Our long and in-depth conversation covers: The rise of Voice systems like Alexa The future of voice, AI, and knowledge Brian's exciting invention Intelligence Amplification And MUCH more Follow Brian ( https://twitter.com/BrianRoemmele ) on Twitter, and check out his website http://voicefirst.expert/ .
Pete Weishaupt – The Golden Age for Creators (EP.28) 24.12.2020 51:43
In this episode of Infinite Loops we spoke with Pete Weishaupt. Our conversation with Pete covers: Starting an e-commerce business Running cheap experiments How to leverage Twitter Behavioral economics And much more Follow Pete ( https://twitter.com/peteweishaupt ) on Twitter, and read his blog here https://maverickmedia.substack.com/ .
Alex Danco – Shopify, SPACs & Status (EP.27) 17.12.2020 1:14:20
In this episode of Infinite Loops we spoke with Alex Danco of Shopify. In this wide-ranging discussion we cover: Alex's first 6 months at Shopify Social Capital & SPACs How Twitter has changed status networks The rise of e-commerce Can Founders Lie? And much more Follow Alex ( https://twitter.com/Alex_Danco ) on Twitter, and read his blog here http://alexdanco.com/ .
Tren Griffin- Escaping Gravity (EP.26) 03.12.2020 1:15:38
In this episode of Infinite Loops we spoke with Tren Griffin, Senior Director at Microsoft and author of the popular business and investing blog 25iq . In this wide-ranging discussion we cover: Base rates and 'escaping gravity' Living a rewarding life. Entrepreneurship and risk-taking The importance of becoming an 'Editor' And much more Follow Tren ( https://twitter.com/trengriffin ) on Twitter, a...
Josh Brown & Brian Portnoy – "How I Invest My Money" (EP.25) 19.11.2020 1:10:31
In this episode of Infinite Loops we spoke with Josh Brown & Brian Portnoy, authors of the newly released book How I Invest My Money . In this discussion, we cover: How Brian and Josh invest personally. Highlighted stories from some of the 25 contributing authors. The concept of "Funded Contentment" How money can be wielded as a weapon Behavioral biases and money Roasting Jamie… and much more Fol...
Michael Batnick – The Irrelevant Investor (EP.24) 05.11.2020 58:07
In this episode of Infinite Loops we spoke with Michael Batnick, Director of Research at Ritholtz Wealth Management. In this conversation, we cover: Michael's journey to Ritholtz Wealth Management His terrible experiences in the insurance industry Breaking into finance How the Ritholtz Wealth Management business has grown And much more Follow Michael on Twitter at https://twitter.com/michaelbatni...
James Clear – Constructing Habits & Systems (EP.23) 22.10.2020 1:02:05
In this episode of Infinite Loops we spoke with James Clear, author of the bestselling book Atomic Habits . In this fascinating discussion, we cover: Maintaining habits amid COVID-19 The importance of time horizons Writing as an antidote to confusion The steps for forming atomic habits And much more Follow James on Twitter at https://twitter.com/JamesClear , and find his book here Atomic Habits .
Annie Duke – How to Decide (EP.22) 15.10.2020 1:21:02
In this episode of Infinite Loops we spoke with Annie Duke, former professional poker player, decision-making expert, and best-selling author. Her latest book is How to Decide: Simple Tools for Making Better Choices , which was released this week. In this conversation, we cover: COVID-19 and decision-making Resulting and the 2016 election What drove Annie to write her new book Writing as a powerfu...
Adam Townsend (Pt. 2) – The Sale (EP.21) 08.10.2020 1:06:15
In this episode of Infinite Loops we invited Adam Townsend back on to speak exclusively about Sales, and why it is so important. In this conversation, we cover: Extreme salesmanship What you cannot learn from Sales books The sales we don't even realize we're making The right and wrong approaches to selling And MUCH more. Follow Adam on Twitter at https://twitter.com/adamscrabble .
Brent Beshore – Boring Businesses, COVID-19, and Doing Better (EP.20) 24.09.2020 1:15:35
In this episode of Infinite Loops we spoke with Brent Beshore, CEO and Founder of Permanent Equity. In this conversation, we cover: What Brent has learned since making his first deal. How COVID-19 has impacted the businesses in Brent's portfolios The importance of time horizons The lasting changes from COVID-19 Finding the right partners and teams in business You can follow Brent on Twitter ( http...
Ron Howard – The Past, Present and Future of Entertainment (EP.19) 10.09.2020 54:35
In this episode of Infinite Loops we spoke with legendary actor, documentarian, Co-Founder of Imagine Entertainment, and academy award winning director Ron Howard. In this wide ranging discussion, we cover: The pressure and thrill of directing a Beatles documentary How the movie industry has evolved, and the impact of COVID-19 How documentaries differ from traditional movie making The future of en...
Phil Pearlman: Westerners Discuss the Tao ("Don't Suck") (EP.18) 03.09.2020 55:33
In this episode of Infinite Loops we spoke with Phil Pearlman. We discuss: What Phil has learned from studying the Tao The narratives you tell yourself The most important rule: Don't suck How marketing & finance has evolved over Phil's career And MUCH more… Follow Phil on Twitter ( https://twitter.com/ppearlman ) to stay up to date on all of his exciting projects.
Tyrone Ross: Giving Back, Empowerment, and Gratitude (EP.17) 20.08.2020 1:07:05
In this episode of Infinite Loops we spoke with Tyrone Ross. We discuss: Tyrone's inspiring journey Empowering youth through financial literacy The power of gratitude Bitcoin and cryptocurrencies And MUCH more… Follow Tyrone on Twitter ( twitter.com/tr401 ) to stay up to date on all of his exciting projects.
Rory Sutherland: Human Behavior, Innovation, and Alchemy (EP.16) 23.07.2020 1:51:20
In this episode of Infinite Loops we spoke with Rory Sutherland, Author of Alchemy: The Dark Art and Curious Science of Creating Magic in Brands, Business, and Life , and Vice-Chairman of Ogilvy Group UK. We discuss: The relationship between marketing and innovation. Human psychology and behavioral economics. The importance of framing. "Stated" preferences and "Revealed" preferences Follow Rory on...
Bronwyn Williams: Self Sovereignty, Futurism, and The State (EP.15) 09.07.2020 1:05:34
In this episode of Infinite Loops we spoke with Bronwyn Williams. We discuss: What being a 'futurist' means Accelerating trends as a result of COVID-19 Geopolitics and the African continent Technology and economic development The future of governance Follow Bronwyn on Twitter ( https://twitter.com/bronwynwilliams ) and check out her website here ( https://whatthefuturenow.com/ )
Anthony Pompliano: Building a Brand, Moats, and Bitcoin (EP.14) 02.07.2020 1:16:34
In this episode of Infinite Loops we spoke with Anthony Pompliano. We discuss: Building a personal brand and business The Bitcoin landscape Moats and innovation The power of Twitter for networking And much more… Follow Pomp on Twitter ( https://twitter.com/APompliano ) and check out his website here ( https://www.youtube.com/c/AnthonyPompliano )
Adam Townsend: Wall Street, Policy, and Wealth Generation (EP.13) 25.06.2020 1:30:55
In this super episode of Infinite Loops, we spoke with Adam Townsend. We discuss: Adam's illustrious career on Wall Street Wealth extraction Extreme salesmanship Adam's COVID-19 blog Chinese foreign and domestic policy And MUCH more… Follow Adam on Twitter ( https://twitter.com/adamscrabble ) and check out his website here ( https://www.adamtownsend.me/ ).
Chris Sommers - Adventures at Sea (EP.12) 18.06.2020 1:14:54
In this episode of Infinite Loops we spoke with Chris Sommers, CEO at Unhedged. We discuss: Sailing the world for 4 years without knowing how to sail Chris' experience at Greenlight Capital Shorting Lehman's stock in 2008 And much more… Follow Chris on Twitter ( https://twitter.com/QuisitiveInvest ) and learn more about Unhedged here ( https://www.unhedged.com/ ).
Chris Sommers - Adventures at Sea (EP.12) 18.06.2020 1:14:54
In this episode of Infinite Loops we spoke with Chris Sommers, CEO at Unhedged. We discuss: Sailing the world for 4 years without knowing how to sail Chris' experience at Greenlight Capital Shorting Lehman's stock in 2008 And much more… Follow Chris on Twitter ( https://twitter.com/QuisitiveInvest ) and learn more about Unhedged here ( https://www.unhedged.com/ ).
Eric Jorgenson: The Almanack of Naval Ravikant (EP.11) 04.06.2020 1:11:25
In this episode of Infinite Loops we spoke with Eric Jorgenson, Product Strategist at Zaarly, and author of the Almanack of Naval Ravikant . We discuss: Who is Naval Ravikant? The key lessons from Naval's writing and career What made Eric want to write this book? Wealth, happiness, and leverage And much more… You can follow Eric on Twitter ( https://twitter.com/EricJorgenson ) and learn more about...
Ed Latimore: Lessons from Boxing, Sobriety, and Building Mental Fortitude (EP.10) 28.05.2020 1:07:21
In this episode of Infinite Loops we spoke with Ed Latimore, a former professional heavyweight boxer (13-1-1) and full-time author that writes about getting sober, forgiveness, and self-improvement. We discuss: The path to sobriety and lessons learned Ed's extraordinary boxing career What Ed dubs the 'manosphere' The importance of transparency and grit And much more… You can follow Ed on Twitter (...
Christie Hamilton: Institutional Investing, Due Diligence During COVID-19, and Advocacy (EP.09) 21.05.2020 48:57
In this episode of Infinite Loops we spoke with Christie Hamilton, Head of Investments at the $2 billion Children's Health Medical Center of Dallas. We discuss: Misconceptions about institutional investing The importance of transparency Due diligence during COVID-19 The traits of a good mentor and mentee And much more… You can follow Christie on Twitter( https://twitter.com/ROIChristie ), and can...
Dan McMurtrie: Pandemic Investing, Venture Capital, and Frontier Markets (EP.08) 07.05.2020 1:22:15
In this episode of Infinite Loops we spoke with Dan McMurtrie, Founder & CEO of Tyro Partners, and Partner at Anchorless Bangladesh. In this in-depth discussion, we cover: Disastrous double dates Navigating uncertain markets in a COVID-19 world Succumbing to behavioral biases in volatile times The investment opportunity in frontier markets Companies that Anchorless is working within Bangladesh The...
Chris Arnade: Seeking Respect in Backrow America (EP.07) 01.05.2020 46:53
In this episode of Infinite Loops, we spoke with Chris Arnade, author of the bestselling book Dignity: Seeking Respect in Backrow America. We discussed: Why Chris left Wall Street to document 'back row America'. How Wall Street has changed over the years Why Chris's work triggers certain crowds of people The importance of McDonald's to American communities The lessons he's learned from traveling...
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