It is believed that highly involved business owners and community members will yield benefits to ensure business and community sustainability over time. However, little research has delved into understanding the role of business owners’ involvement and the community’s involvement in business outcomes. Thus, the purpose of this study was to investigate the reciprocal involvement of family business owners and the community. To investigate this phenomenon, this study utilized survey data from a rare group of business owners who currently operate long-standing businesses. Results indicate that more involved business owners perceived higher levels of business success. When seeking a profit, business owners also tended to be more involved in the community than owners not seeking a profit. However, family-owned businesses felt that the community did not contribute to their businesses and did not stay involved over time. Overall, business owners felt that they contributed more than the community provided in return. Recommendation is made to stress in entrepreneurship curricula the importance of reciprocal involvement between businesses and their communities and vice versa to promote business and community sustainability over time