This chapter analyzes the intersection of entrepreneurship, innovation, digitalization, and risk in family businesses, focusing on the bibliometric cluster “Entrepreneurship, innovation, digitalization, and risk” (yellow cluster). The analysis shows that, compared to their non-family counterparts, family businesses tend to adopt a more cautious entrepreneurial approach, favoring incremental innovations, reactive strategies, and gradual change processes aimed at limiting risk exposure and preserving the continuity of family control. At the same time, the chapter highlights how the presence of a new generation of leadership, the contribution of external human capital, and the formalization of governance processes can trigger trajectories of transformation in which innovation, including digital innovation, becomes a lever for reducing perceived risk, strengthening competitiveness, and opening the entrepreneurial family to more systematic risk management approaches.