The new Germany provides a once-in-a-lifetime living laboratory in which to explore entrepreneurship and family business. On one hand, established West German family-led firms are responding to generational change and the need for new entrepreneurial leadership. On the other hand, the East must rely on entrepreneurship and new venture creation to rebuild this region of Germany. Thus, this study poses the following general research question: “How similar or different are the entrepreneurial orientations and family forces of East German and West German entrepreneurs?” The study explores three dimensions shaping entrepreneurial characteristics and orientations: (a) sociocultural forces (principally the family and personal alliance networks, capturing characteristics associated with demographics, family involvement, and enterprise profiles); (b) personality characteristics associated with entrepreneurial intensity, sacrifice, and achievement motives, which shape entrepreneurial orientation; and (c) environmental perceptions related to infrastructure obstacles confronting entrepreneurial-led family enterprises. The study draws from a sample of 160 East and West German entrepreneurs. The data isolate the differences and identify similarities between East and West German entrepreneurs, as well as provide valuable insights into the family forces shaping SMEs in the new Germany.