PurposeThis study provided a unique opportunity to analyze five generations of a small but continually evolving family-owned media organization with multiple media outlets operating across delivery platforms. The purpose of this paper is to identify variables that contributed to entrepreneurship and sustainability, holding the family business intact for more than 100 years.Design/methodology/approachThis study used organizational ecology in a qualitative case study to interview entrepreneurs from three of five generations. Additionally, current employees, family and friends, along with letters, cards, published articles and financial data were included in the analysis. Entrepreneurial themes based on organizational ecology were identified including variation, selection, retention, as well as values, innovation, service and adaptability.FindingsThe company in this study began with the purchase of newspapers and start-up of a news service in 1904. By the third generation, entrepreneurial initiatives included additional newspapers, as well as a television start-up. In the fourth and fifth generations, the company evolved into what the family termed a “media development company” with a mix of revenue platforms including electronic newspapers, websites, radio stations, live events and syndicated programs.Research limitations/implicationsLimitations included sample size and focus on the perspectives of family members. More research is needed to identify the struggles within the family media firm and the more troubling aspects of a family company as indicated in the literature and their possible downside to both employees and family members who work for the short term or long haul in smaller, family-owned companies.Practical implicationsSustainability of family-owned media organizations occurred through a balance of entrepreneurial activities and family values. Revenue flows resulted from adapting business models from selling advertising in local newspapers to providing funding and other support to local businesses gaining footholds. Market innovation, risk and community-minded solutions resulted in survival through stages of variation, selection and retention.Social implicationsFor family media companies to thrive, entrepreneurship and adaptability are key. Significant contributions to theory from this study indicated organizational ecology is a useful tool in analyzing the evolution of a media company through stages of variation, selection and retention. After almost 80 years of operation in the retention stage, the company started over in the variation stage with new products including radio, internet, live events and community business ventures. Timely diversification was key as media and community landscapes changed.Originality/valueUnique findings indicated sustainability came through a family-oriented approach to business that carried on throughout generations: a long-term view with a commitment to family values, the promotion of entrepreneurial opportunities for family and non-family members and an external focus as media development companies on the success of local businesses and communities in which they operated.