We Study Billionaires - The Investor’s Podcast Network

In a captivating discussion, Harris Kupperman, founder and CIO of Praetorian Capital Management, shares his investment strategies shaped by macro trends and events. He reveals the secrets to effective macro investing and the importance of solid capital allocation. Kupperman argues against overhyped stocks while advocating for asset-heavy investments during inflation. He underscores the value of patience and adaptability in an ever-changing market, and explores the pros and cons of hedging as a strategy. This conversation is a goldmine for investors eager to rethink traditional approaches.

In this episode, Clay explores When Genius Failed by Roger Lowenstein, the gripping story of the rise and fall of Long-Term Capital Management (LTCM). Founded by Wall Street’s brightest minds, including Nobel Prize-winning economists, LTCM generated astronomical returns using complex mathematical models and extreme leverage—until a financial crisis in 1998 exposed its fatal flaws. Clay also discusses the dangers of overconfidence, the illusion of diversification, and why excessive leverage can be a ticking time bomb. Additionally, he shares details on an exclusive value investing event hosted by TIP in Big Sky, Montana, in September 2025. IN THIS EPISODE YOU’LL LEARN:00:00 - Intro03:34 - How John Meriwether and a team of Wall Street’s brightest minds, including Nobel laureates, built a hedge fund that seemed invincible, using sophisticated financial models and extreme leverage.25:55 - LTCM’s reliance on mathematical models that assumed markets behaved rationally, leading them to underestimate the possibility of extreme events.48:30 - How the Russian debt default triggered widening credit spreads, exposing LTCM’s overleveraged positions and leading to catastrophic losses.54:49 - Why LTCM’s failure posed systemic risks to the global financial system, forcing the Fed to coordinate a rescue with major Wall Street banks.01:08:17 - The dangers of excessive leverage, overconfidence in financial models, and the mistaken belief that markets always revert to historical norms.01:15:09 - How to attend our new value investing event in Big Sky, Montana, bringing together passionate investors for deep discussions and meaningful connections.And so much more! Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.BOOKS AND RESOURCES Join Clay and a select group of passionate value investors for a retreat in Big Sky, Montana. Learn more here. Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, Kyle, and the other community members. Lowenstein’s book: When Genius Failed. Mentioned book: Big Mistakes. Related Episode: Listen to TIP514: Permanent Supply Chain Disruptions that Will Destroy the Economy w/ Jim Rickards. Email Shawn at shawn@theinvestorspodcast.com to attend our free events in Omaha or visit this page. Follow Clay on X. Check out all the books mentioned and discussed in our podcast episodes here. Enjoy ad-free episodes when you subscribe to our Premium Feed. NEW TO THE SHOW? Get smarter about valuing businesses in just a few minutes each week through our newsletter, The Intrinsic Value Newsletter. Check out our We Study Billionaires Starter Packs. Follow our official social media accounts: X (Twitter) | LinkedIn | Instagram | Facebook | TikTok. Browse through all our episodes (complete with transcripts) here. Try our tool for picking stock winners and managing our portfolios: TIP Finance Tool. Enjoy exclusive perks from our favorite Apps and Services. Learn how to better start, manage, and grow your business with the best business podcasts. SPONSORSSupport our free podcast by supporting our sponsors: SimpleMining Hardblock AnchorWatch CFI Education Found Fundrise Indeed The Bitcoin Way Vanta Shopify Onramp TurboTax HELP US OUT!Help us reach new listeners by leaving us a rating and review on Spotify! It takes less than 30 seconds, and really helps our show grow, which allows us to bring on even better guests for you all! Thank you – we really appreciate it!Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fmSupport our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fmSupport our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fmSupport our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Learn more about your ad choices. Visit megaphone.fm/adchoicesSupport our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm

Join Jeff Ross, a macroeconomic expert, American Hodl, a Bitcoin community leader, and Joe Carlasare, a legal analyst, as they dive into the economic landscape surrounding Bitcoin. They discuss the impact of dollar weakness and liquidity on global markets, along with insights into Bitcoin bonds. The conversation tackles the implications of tariffs on inflation and reveals critical updates on regulatory frameworks affecting the cryptocurrency industry. Their predictions on contrarian buy signals for Bitcoin offer intriguing insights for investors.

Pico Iyer, a renowned author and speaker celebrated for his TED talks, discusses his latest book, "Aflame." He shares insights on finding peace and clarity amidst chaos, emphasizing the importance of silence in nurturing a calm mind. Iyer reflects on his extensive stays at monasteries, illustrating how craving less leads to greater fulfillment. He champions the concept of an 'inner scorecard,' likening great investors to monks. The conversation also touches on the power of solitude and gratitude in navigating life's challenges.

In this discussion, Cristiano Souza, founder of Zeno Equity Partners, shares his investment wisdom gleaned from 28 years at Dynamo. He reveals his three key criteria for identifying exceptional businesses. Cristiano dives deep into the elusive founder's mindset, the growth potential of LVMH, and the importance of management team evaluation, including his own past mistakes. He highlights why Linde PLC is a staple in his portfolio and discusses AppFolio's strong positioning in property management, emphasizing long-term strategies amidst market volatility.

Daniel Batten, an energy expert and investor at the forefront of Bitcoin mining infrastructure, dives into the synergy between Bitcoin and renewable energy. He discusses how Bitcoin mining can transform methane emissions into energy solutions and decentralize global energy markets. Batten explains the future of heat reuse in mining, innovative methods like zinc recycling, and the dynamic intersection of AI with Bitcoin. He also sheds light on how Bitcoin is revolutionizing energy consumption, even challenging perceptions of nuclear energy's role in sustainability.

Kyle Grieve chats with Adam Wilk, Founder of Greystone Capital Management, who transitioned from NBA scouting to investing. They discuss the art of spotting hidden value—skills honed while evaluating talent for sports. Adam emphasizes incremental progress in investing, revealing how a labor-intensive approach leads to better insights. He also shares lessons on identifying quality small-cap stocks, the impact of low costs on market sensitivity, and the importance of authentic partnerships in investment strategies. A fascinating blend of sports and finance!

Tae Kim, a senior technology writer at Barron's and author of "The Nvidia Way," dives into Nvidia's remarkable journey. Discover how Jensen Huang's relentless ambition and a unique corporate culture have propelled Nvidia to the forefront of AI innovation. Kim shares insights from over 100 interviews that reveal Nvidia's strategies for thriving in a competitive market. He discusses the company's transformation, the invention of the GPU, and how their forward-thinking approach positions them as leaders in the generative-AI revolution.

Matthew Mezinskis, an expert on global liquidity, delves into Bitcoin's unique design and its role as a safeguard against centralized financial risks. He discusses Bitcoin's price modeling, including stock-to-flow analysis, and how macroeconomic trends influence its value. The conversation highlights the impact of global liquidity, Bitcoin's potential as a store of value, and the significance of Layer-2 solutions in enhancing liquidity. Matthew also shares a bold prediction about Bitcoin's transformative role in the future of global finance.

Stig Brodersen and William Green explore what made them richer, wiser, and happier in recent months. They discuss how to embrace vulnerability and the healing power of kindness, while sharing personal anecdotes about confronting emotional struggles. The conversation highlights the importance of genuine connections and navigating trust in the investing community. They also reflect on cultural attitudes toward success, the impact of small acts of generosity, and finding wisdom through literature. Join them for insights on personal growth and forging meaningful relationships.