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The Myth of High Win Rates

In this episode of Thinking in Options, the focus shifts from win rates to the concept that truly determines long-term trading success: expected value. Using clear examples—from roulette tables to common options strategies—the episode explains why high win rates can be misleading and often hide large, infrequent losses. Listeners will learn why markets reward payoff-weighted outcomes rather than frequency of wins, and how many popular strategies—like consistently selling out-of-the-money puts—can create the illusion of safety while quietly accumulating tail risk. The takeaway: profitable trading isn’t about how often you’re right, but whether the payoff when you’re right outweighs the risk when you’re wrong.