This study endeavors to reconcile the limited, mixed findings related to entrepreneurship and corporate social responsibility in the family firm context. Specifically, the relationships between entrepreneurial orientation (EO), sustainable investments in environmental and societal initiatives, and the interaction of EO and sustainable investments with family firm performance are evaluated. Data were collected through in-person interviews of 151 top managers of automobile and motorcycle dealerships. Secondary data were collected from ReferenceUSA to confirm the veracity of the primary performance data. Multiple linear regression models were used to evaluate the hypothesized relationships. The results indicate family firms realize higher performance with an EO by being proactive, innovative, and risk-taking. Moreover, sustainable investments are associated with higher family firm performance by either increasing revenues or decreasing costs. EO does not significantly accentuate the positive relationship between sustainable investments and performance. The observed interaction was contrary to expectations with EO acting as a substitute for sustainable investments; firms with an EO use a variety of initiatives, including but not limited to society and the environment, to improve performance. These findings advance the family business literature on entrepreneurship and corporate social responsibility theory by establishing EO and socially responsible, sustainable investments as antecedents of family firm performance while also analyzing the EO-sustainable investment interaction.