The article analyzes the relationship between entrepreneurial philanthropy and the competitive process. Competitive conditions interacted significantly with entrepreneurial responses to ethical problems posed by the rapid emergence of factory production following the British Industrial Revolution. Entrepreneurs’ attitudes toward regulation and the labor process are used to identify the major differences and similarities in competitive behavior. These variations are explored using nineteenth-century case studies highlighting examples of philanthropy and competitive behavior. The analysis leads to a typology showing that entrepreneurial philanthropic behavior is conditioned by business strategy variables: specifically, combinations of technological and labor resources controlled by individual entrepreneurs and their businesses.