We Study Billionaires - The Investor’s Podcast Network

Kyle discusses the investing evolution of John Maynard Keynes and the timeless lessons modern investors can draw from his successes and failures.

IN THIS EPISODE YOU’LL LEARN:
00:00:00 - Intro
00:03:50 - Why John Maynard Keynes is such a fascinating case study in evolving as an investor
00:08:28 - A key resource that helped him think of assets from a bottom-up approach
00:10:59 - Why Keynes's experiences of going broke multiple times helped shape him into a long-term thinker
00:17:13 - How he thought about speculation and investing, and used that to beat the market
00:28:16 - How he improved his temperament, overcame overconfidence, and adopted a long-term mindset
00:36:21 - His thoughts on diversification and reducing risk
00:41:30 - Why he believed that markets were social systems, and the errors that exposed investors to
00:50:25 - What he thought about short-term volatility
01:01:16 - Why Keynes used adaptability as such a powerful tool
01:03:50 - Six impactful takeaways

Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.

BOOKS AND RESOURCES

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William Green highlights essential truths about investing, business & life that emerged from two of his favorite interviews with Howard Marks and Nima Shayegh. This episode also explores powerful lessons on resilience from Bill Miller & Epictetus.

IN THIS EPISODE YOU’LL LEARN:
00:00:00 - Intro
00:04:31 - How investing legend Howard Marks views the euphoria over AI
00:11:10 - What potential mistakes he warns against in this environment
00:13:23 - What essential lessons William Green has learned from Howard
00:23:00 - How Howard keeps an even keel amid extreme uncertainty
00:26:09 - Why Howard, like Einstein, doesn’t think much about the future
00:34:19 - Why investing early & not “tampering” is the key to success
00:38:39 - How Nima Shayegh looks beyond numbers to find great stocks
00:44:19 - How to harness intuition & emotion in the investment process
00:49:13 - How products from Tesla & Amazon inspire “blown-awayness”
00:57:10 - What Nima learned from his famed mentor, Lou Simpson
01:04:38 - How Lou’s success was built on humility
01:19:55 - How Lou & Nima inspire William’s yearning for a spacious life
01:23:56 - How to handle suffering with help from Bill Miller & Epictetus

Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.

BOOKS AND RESOURCES

Join the exclusive ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TIP Mastermind Community⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to engage in meaningful stock investing discussions with Stig, Clay, Kyle, and the other community members.

Inquire about William Green’s ⁠⁠⁠⁠⁠⁠Richer, Wiser, Happier Masterclass⁠⁠⁠⁠⁠⁠.

Howard Marks’ Memos: The Complete Collection.

Edward Chancellor's Devil Take the Hindmost.

Allen Benello, Michael van Biema, Tobias Carlisle's
⁠Concentrated Investing.⁠

William Green’s podcast interview with Howard Marks.

William Green’s podcast interview with Nima Shayegh.

William Green’s book, ⁠⁠Richer, Wiser, Happier⁠⁠.

Follow William Green on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠X⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.

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Support our free podcast by supporting our ⁠⁠sponsors⁠⁠:


HardBlock⁠


⁠Human Rights Foundation⁠


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⁠Fundrise

References to any third-party products, services, or advertisers do not constitute endorsements, and The Investors Podcast Network is not responsible for any claims made by them.
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Clay explores Daniel Kahneman’s book Thinking, Fast and Slow, unpacking the cognitive biases that quietly shape our investment decisions. While markets often appear to be driven by data and logic, our decisions are frequently influenced by intuition, emotions, and mental shortcuts we don’t even realize we’re using. 

IN THIS EPISODE YOU’LL LEARN:
00:00:00 - Intro
00:04:15 - Why temperament matters more than IQ in investing
00:11:10 - The difference between System 1 and System 2 thinking
00:16:01 - How cognitive substitution leads investors to answer the wrong questions and unknowingly ignore the more important questions
00:38:08 - How loss aversion shapes investor behavior during drawdowns and market volatility
00:54:01 - Clay’s updated views on Constellation Software

Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.

BOOKS AND RESOURCES

Join the exclusive ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TIP Mastermind Community⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to engage in meaningful stock investing discussions with Stig, Clay, Kyle, and the other community members.

Learn how to join us in Omaha for the Berkshire meeting ⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠⁠⁠⁠.

Daniel Kahneman’s book: Thinking Fast & Slow.

Sequoia Fund’s 2025 year-end letter.

Follow Clay on ⁠⁠X⁠⁠ and ⁠⁠LinkedIn⁠⁠. 

Related ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠books⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ mentioned in the podcast.

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Alex Gladstein and Justin Moon break down the fundamentals of large language models and explore the rise of OpenClaw as a self-sovereign AI assistant.

Justin explains context engineering, local inference, and vibe coding, while Alex dives into the AI for Individual Rights program and its mission to empower activists.

IN THIS EPISODE YOU’LL LEARN:

00:00:00 - Intro
00:04:12 - What Large Language Models (LLMs) are and how they differ from traditional programs
00:05:15 - Why AI feels like magic—and what’s really happening under the hood
00:06:01 - The key differences between open and closed AI models
00:06:50 - Why capital structures influence AI model openness
00:09:09 - How persistent memory enhances AI agent performance
00:12:18 - What inference means and why context is a scarce resource
00:19:32 - How AI agents combine traditional software with LLM reasoning
00:21:10 - The evolution from MCP-style systems to skills-based context engineering
00:25:41 - What “vibe coding” is and how it lowers the barrier to building apps
00:44:07 - How the AI for Individual Rights program supports activist-driven innovation

Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.

BOOKS AND RESOURCES

Oslo Freedom Forum: Website.

Justin:  Nostr account.

Related episode:  Is AGI Here? Clawdbot, Local AI Agent Swarms w/ Pablo Fernandez & Trey Sellers.

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