The overemphasis on individualism in much normative entrepreneurship discourse belies the powerful role played by local level and communal forms of barter, culturally based collectivist models of organization, social enterprise, and other forms of co-investment. Following Rindova et al., we argue innovation in entrepreneurship can be an emancipatory process with broad change potential to bring about new economic, social, institutional, and cultural environments. New forms of productive social relations and cooperative effort generate new ways of liberating individual and collective existence. However, the dark side of entrepreneurialism also casts its shadow over the pursuit of an idealized commons. Romanticizing forms of collective entrepreneurialism as a means for elevating vulnerable groups may have contrary effects, especially for those already socially and economically marginalized. Theorizing entrepreneurship from a critical perspective, we draw on Laclau’s emancipation–oppression dualism. We explore the contradictions and potentialities of locally based communal entrepreneurship as expressions of a dynamic tension, which is simultaneously both transformative and exploitative in orientation.