Drawing from evolutionary psychology and the too-much-of-a-good-thing (TMGT) effect, the current research considers whether basic moral values held by entrepreneurs might serve as a double-edged sword that leads such persons into starting new ventures but eventually undermines their satisfaction and performance. Research from the field of social psychology has created a classification of twenty-four character strengths that are found to be consistently valued across all major cultures (Peterson & Seligman, 2004). These character strengths cluster together to form six distinct virtues. Individuals act out their virtues through the application of their associated character strengths. The present research focuses on the virtues of “justice” and “wisdom and knowledge”. These virtues were selected for study based on anticipated sex differences with respect to how they relate to important entrepreneurial outcomes. Specifically, the current research considers whether there are sex differences in the relationship of these virtues with entrepreneurial entry, satisfaction and performance.