
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!"
Latest episodes

Dec 3, 2020 • 1h 16min
Tren Griffin- Escaping Gravity (EP.26)
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, and read his blog here 25iq.

Nov 19, 2020 • 1h 11min
Josh Brown & Brian Portnoy – “How I Invest My Money” (EP.25)
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 Follow Josh (https://twitter.com/ReformedBroker) and Brian (https://twitter.com/brianportnoy) on Twitter, and their new book here How I Invest My Money: Finance Experts Reveal How they Save, Spend, and Invest.

Nov 5, 2020 • 58min
Michael Batnick – The Irrelevant Investor (EP.24)
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/michaelbatnick , and find his blog here The Irrelevant Investor.

Oct 22, 2020 • 1h 2min
James Clear – Constructing Habits & Systems (EP.23)
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.

41 snips
Oct 15, 2020 • 1h 21min
Annie Duke – How to Decide (EP.22)
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 powerful tool for testing your knowledge And MUCH more. Follow Annie on Twitter at https://twitter.com/AnnieDuke , and find her new book here https://www.amazon.com/gp/product/0593418484?tag=randohouseinc13176-20.

11 snips
Oct 8, 2020 • 1h 6min
Adam Townsend (Pt. 2) – The Sale (EP.21)
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 .

Sep 24, 2020 • 1h 16min
Brent Beshore – Boring Businesses, COVID-19, and Doing Better (EP.20)
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 (https://twitter.com/BrentBeshore) and learn more about Permanent Equity here (https://www.permanentequity.com/about-our-firm)

Sep 10, 2020 • 55min
Ron Howard – The Past, Present and Future of Entertainment (EP.19)
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 entertainment and how streaming changes things And MUCH more Enjoy!

Sep 3, 2020 • 56min
Phil Pearlman: Westerners Discuss the Tao (“Don't Suck”) (EP.18)
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.

Aug 20, 2020 • 1h 7min
Tyrone Ross: Giving Back, Empowerment, and Gratitude (EP.17)
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.