This episode explores the impact of debt on longevity and financial stability, drawing insights from Morgan Housel's analysis of long-lasting Japanese businesses, Shinisei, which typically avoid debt and hold substantial cash reserves. Howard Marks reflects on his 2008 memo, "Volatility plus Leverage equals Dynamite," emphasizing that the prudence of using borrowed money depends on the riskiness of the assets being purchased; stable assets allow for more leverage, while riskier assets require less. The discussion highlights that debt, or leverage, is used to increase capital efficiency, magnifying potential gains but also amplifying losses, with the added risk of ruin during downturns. Marks stresses the importance of recognizing volatility and the potential for extreme events, which are often underestimated, leading to excessive leverage. Furthermore, the episode examines the cyclical nature of attitudes toward risk and debt, noting that periods of prosperity often lead to the overestimation of leverage's benefits and the underestimation of its risks. Ultimately, the right approach to debt involves optimizing rather than maximizing, using it moderately with cautious assumptions to balance potential gains against the risk of significant losses and ensure long-term financial survival.