
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

May 6, 2021 • 1h 20min
Jeremiah Lowin — Embracing Uncertainty (EP.46)
In this episode of Infinite Loops, we speak with Jeremiah Lowin, CEO at Prefect. In this conversation we cover: Overcoming inertia When information challenges your beliefs Choosing the right words for expression Narratives and decision-making Building a culture that appreciates uncertainty And A LOT more Follow Jeremiah on Twitter (https://twitter.com/jlowin), and learn more about Prefect at https://www.prefect.io/

Apr 29, 2021 • 1h 19min
Jesse Livermore – What Now? (EP.45)
In this episode of Infinite Loops we spoke with OSAM Research Partner Jesse Livermore (pseudonym). In this conversation we chat: MMT and valuations Bitcoin: Bull & Bear Cases Transactional valuation Intrinsic valuation Managing future crises And MUCH more Follow Jesse on Twitter (https://twitter.com/Jesse_Livermore), and check out his writing here (http://www.philosophicaleconomics.com/).

11 snips
Apr 22, 2021 • 1h 13min
Daniel Jeffries – Questioning Everything (EP.44)
In this episode of Infinite Loops we spoke with Daniel Jeffries, futurist and author. Daniel’s newest book is Mastering Depression and Living the Life You Were Meant to Live. In this conversation we chat: The multiverse Why Dan wrote his newest book Mimetic desires and human behavior Questioning everything And MUCH more Follow Daniel on Twitter (https://twitter.com/Dan_Jeffries1), check out his writing (https://medium.com/@dan.jeffriescheck), and find his new book here.

Apr 15, 2021 • 1h 5min
Howard Lindzon – The Larry David of Finance (EP.43)
In this episode of Infinite Loops we spoke with Howard Lindzon, Founder & General Partner at Social Leverage, and Founder of StockTwits. In this conversation we chat: Why Howard is Larry David The reasons he launched a SPAC How SPACs differ from Venture Capital His thoughts on FinTech & Crypto And MUCH more Follow Howard on Twitter (https://twitter.com/howardlindzon), and check out his website (https://howardlindzon.com/)

Apr 8, 2021 • 1h 4min
Joe Weisenthal - Rapid Fire (EP.42)
In this episode of Infinite Loops, we spoke with Joe Weisenthal, Executive Editor of Digital News at Bloomberg. In this fun and thought-provoking conversation we chat: • NFTs • Bitcoin Believers and its viability • MMT • Robinhood • And MANY more sensitive subjects Follow Joe on Twitter (Twitter.com/thestalwart).

Apr 1, 2021 • 1h 4min
Bill Brewster – Asking Tough Questions (EP.41)
In this episode of Infinite Loops we spoke with Bill Brewster, investor and host of The Business Brew podcast. In this conversation we covered: How Bill’s investment career took shape. The tragic story of Bill’s relative. Important questions on Robinhood. Investor education. Gambling vs. Investing. And MUCH more. Follow Bill on Twitter (https://twitter.com/BillBrewsterSCG) and check out Bill’s podcast (https://www.podpage.com/the-business-brew/)

Mar 25, 2021 • 51min
Josh Wolfe - Inventing The Future (EP.40)
In this episode of Infinite Loops we spoke with Josh Wolfe, co-founder and managing partner at Lux Capital. In this conversation we covered: The acceleration of technological change. Inflation, the dollar, and crypto. Macro and geopolitical risk. Lux’s portfolio companies And MUCH more Follow Josh on Twitter (https://twitter.com/wolfejosh) and check out Lux Capital (https://luxcapital.com/)

Mar 18, 2021 • 1h 13min
Alex Danco - Makes A Scene (EP.39)
In this episode of Infinite Loops we spoke with Alex Danco of Shopify. In this wide-ranging discussion we cover: How to create a scene Great scenes and movements from history The Canadian startup market The Pepsi/Coke blind taste test And MUCH more Follow Alex (https://twitter.com/Alex_Danco) on Twitter, and read his blog here http://alexdanco.com/ .

Mar 11, 2021 • 60min
Anna Gat – Learning Through Discussion (EP.38)
In this episode of Infinite Loops we spoke with Anna Gat, Founder and CEO of Interintellect. In this conversation we covered: Power of conversation The Salons that Anna runs The importance of framing Communication differences in genders Fostering human connection And MUCH more Follow Anna on Twitter (https://twitter.com/TheAnnaGat) and check out Interintellect (www.Interintellect.com)

Mar 4, 2021 • 1h 4min
Max Arbitrage – Healthcare, Investing & Biology (EP.37)
In this episode of Infinite Loops we spoke with the man behind anonymous Twitter account Max Arbitrage. Max is an investor, entrepreneur, and top mind in the health care industry. In this conversation we covered: Game theory and modern markets Deterministic vs. probabilistic thinking Max’s entrepreneurial ventures Fixing what sucks in an industry The perils of status games And MUCH more Follow Max on Twitter (https://twitter.com/max_arbitrage).