Research summary: This conceptual article discusses when and why family firms are motivated to engage in entrepreneurial activities. Drawing on family development theory, we offer midrange reasoning about the impact of enterprising family dynamics—such as the birth of a child or children leaving home—on the motivation for corporate venturing and its changes over time. Moreover, our model also accounts for the contingent effect of ownership and business developmental dimensions. Finally, we predict that motivation for corporate venturing can, in turn, spur the development of the enterprising family. Managerial summary: Overcoming the idea that family firms are either very or minimally entrepreneurial, we focus on the enterprising family and consider its development to explain the motivation toward corporate venturing. We look at the evolution of the roles and norms of family members over time and predict that motivation for venturing increases with family growth until the moment in which a succession takes place and the younger generation receives the baton. We also consider how changes in the ownership structure and business growth influence the relationship between family development and motivation for venturing. The latter, in turn, can trigger the development of the enterprising family itself, with its structure and norms. Our work, in sum, depicts the enterprising family as a springboard for repeated acts of entrepreneurship across generations.