We investigate how parental income during one's upbringing relates to his or her effectiveness as a leader after entering an organization. Drawing on research on the psychological effects of income, social learning theory, and the integrative trait-behavioral model of leadership effectiveness, we propose a negative, serially mediated association between higher parental income and lower future leader effectiveness via high levels of narcissism and, in turn, reduced engagement in behaviors that are viewed as central to the leadership role. We test our model using multisource data collected from active soldiers in the United States Army. Results reveal that parental income exerts indirect effects on leadership effectiveness criteria because a) parental income is positively related to narcissism as an adult, b) narcissism relates negatively to engaging in task-, relational-, and change-oriented leadership behaviors, and c) reduced engagement in these behaviors relates to lower leader effectiveness. Our investigation advances theory by identifying pathways through which parental income relates to the effectiveness of leaders in organizations, and by illuminating the origins of a trait (narcissism) that predicts the behavior and effectiveness of leaders.