This episode examines tail hedging as a strategic method for protecting investment portfolios against extreme market crashes. Drawing on the theories of Nassim Taleb and Mark Spitznagel, the author explains that markets frequently experience "fat tails," or catastrophic events that occur more often than traditional models predict. To mitigate these risks during periods of asset inflation, investors can systematically purchase out-of-the-money put options to serve as a form of financial insurance. This specific strategy involves allocating a small, consistent percentage of capital to options that gain significant value if the market indices plummet. While this approach incurs a regular cost, it is presented as a vital tool for preserving wealth when stock valuations reach historically dangerous levels. Ultimately, the source argues that such defensive maneuvers are most effective when reward-to-risk ratios are unfavorable for traditional buy-and-hold investors