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Family firms are widely recognized as a major source of technological innovation and economic progress. Yet, over time, some family firms become conservative and unwilling to take the risks associated with entrepreneurial activities. Adopting a broad definition of entrepreneurial risk taking, this study uses agency theory to highlight key correlates of risk taking among 209 U.S. manufacturing family firms. The results show that family ownership and involvement promote entrepreneurship, whereas the long tenures of CEO founders have the opposite effect. These results urge managers to capitalize on the skills and talents of their family members in promoting entrepreneurship and selective venturing into new market arenas.