The Small Business Administration (2009) reported the small business sector employs approximately half of U.S. workers and creates 60–80% of all new jobs. The U.S. workforce is now comprised of four different generational cohort groups, each group with its own history, value-shaping experiences, and motivational patterns. This is a quantitative study, a survey of leaders in the direct-to-consumer catalog industry with revenues ranging from $15–100 million. The first purpose of this study was to determine the degree to which leadership styles (transactional, transformational, and laissez-faire) are used by four different generational cohorts (Veterans, Baby Boomers, Generation X, and Generation Y) of small business leaders in the direct-to-consumer catalog industry. The second purpose of this research was to determine how well the degree of leadership style predicts organizational outcomes in these small business organizations. The Multifactor Leadership Questionnaire was used to address the hypotheses and multivariate analysis of variance and multiple regression were used to analyze the data gathered. This research bridges a gap in the literature on leadership styles, organizational outcomes, and the generational differences in the direct-to-consumer catalog industry.