TIP758: Current Market Conditions & Investment Opportunities w/ Derek Pilecki
Host Clay Fink interviews hedge fund manager Derek Pilecki about his recent performance and how he is navigating current market conditions in the financial sector. Pilecki explains his process of targeting ideas with potential to double in three years, combining value investing with an awareness of momentum and technicals, and selectively using leverage at both the company and portfolio level. He discusses opportunities in regional and European banks, beaten-down fintech names, case studies in Robinhood and WEX, and his views on interest rate cuts, inflation, and the real estate market.
TIP757: Richer, Wiser, Happier Q3 2025 w/ Stig Brodersen & William Green
Host Stig Brodersen and co-host William Green have a wide-ranging quarterly Richer, Wiser, Happier discussion on universal truths, money and happiness, and the role of books and teachers in living well. They explore epistemic humility, cultural and psychological differences in values, and how these insights apply to investing decisions. They also examine research on income and happiness, how wealth can and cannot improve life, and share their own reading habits and spiritual influences that shape their thinking about how to live.
TIP756: The Rise and Fall of Julian Robertson's Tiger Fund w/ Kyle Grieve
Host Kyle Grieve presents a solo deep dive into the career of hedge fund legend Julian Robertson and the rise and fall of his Tiger Fund. He covers Robertson's background, investment philosophy, famous trades such as the mid-1990s copper short, his use of networks and sentiment to find mispricings, and his seven core stock-picking themes. The episode also examines how leverage, fund size, market bubbles, and centralized decision-making contributed to Tiger's eventual closure during the dot-com era.
TIP755: My Process for Finding Great Investments w/ Kyle Grieve
Host Kyle Grieve shares his personal investing philosophy, tracing how early speculative losses in cryptocurrencies led him toward disciplined value investing in equities. He explains his return goals, focus on absolute rather than relative performance, a two-bucket framework (quality compounders and microcap inflection-point stocks), detailed criteria for evaluating management and capital efficiency, and his sell and portfolio management rules. Kyle also covers concepts like circle of competence, behavioral biases, environment design for inaction, and reflects candidly on mistakes of commission and omission to illustrate how he continues refining his process.
How To Turn $100K into $4,000,000 with Distressed Investing
The hosts interview a distressed investor named Tom who specializes in buying bankruptcy claims, especially in crypto-related cases like Mt. Gox and FTX, and walk through how his niche works. He explains the "stake and sizzle" approach to finding situations with both downside protection and significant upside optionality, details the hustling and legal knowledge required to trade claims, and shares stories from early crypto bankruptcies and his own investing background. Later, he candidly discusses a controversial Delaware receivership case that resulted in fines and a settlement, and closes with core investing philosophies and a reading list for learning more about distressed and value investing.
TIP754: Rule Breaker Investing w/ David Gardner
Host Clay interviews David Gardner, co-founder of The Motley Fool, about his new book "Rule Breaker Investing" and the distinctive growth-oriented philosophy that produced multiple 100-bagger stock picks like Amazon, Netflix, and NVIDIA. Gardner explains why he diverged from Warren Buffett-style value investing, embraces losses as part of a venture-capital-like approach, and focuses on qualitative factors such as leadership, culture, and brand that traditional valuation metrics ignore. The conversation also covers his six traits of Rule Breaker stocks, six habits of Rule Breaker investors, conscious capitalism, the importance of optimism, and several current companies he believes embody his framework.