This study investigates the impact of socio-emotional wealth (SEW) on family firm entrepreneurial orientation (EO) in in Saudi Arabia, and the moderating effect of generational involvement on this relationship. Our data set comprises 241 privately, wholly owned family firms. We examine EO as a strategic orientation expressed in terms of both firm behavior and how managers approach risk-taking attitudinally. Our study finds that SEW is positively related to firms’ entrepreneurial behavior, but not managerial attitudes toward risk-taking. However, the positive effects of SEW on firms’ entrepreneurial behavior diminish as the number of generations involved in the family business increases. The broader implications for enabling entrepreneurship within Arab transforming economies adhering to strong cultural tribalistic norms are discussed.