Today I speak with David Sun, a retail trader who started his own hedge fund. Coming from a non-traditional background, David takes a non-traditional approach in his investment mandates.  Focused on selling options to capture the volatility risk premium, David believes that markets are ultimately efficient and therefore foregoes using any sort of active signal.  Instead, he focuses on explicitly controlling his win size relative to his loss size, and then choosing a strategy with a win rate that bumps him into positive expectancy.  By then maximizing the number of “at bats,” he lets the Central Limit Theorem take care of the rest.  It’s an approach he calls “expectancy hacking.” We discuss this approach in both theory and practice, addressing issues such as trading costs and slippage drag, as well as both sequence and event risk.  David’s approach is certainly non-traditional, but highlights some unique concepts of how traders may be able to architect a payoff profile around a risk premium. Please enjoy my episode with David Sun.