We introduce the concept of “relational reflexivity”—drawn from realist and relational sociological theories—to examine how external actors engage in the collective process of endogenous social change driven by community-based entrepreneurship. Relational reflexivity allows individuals to reflect on the quality of their relationships (relational goods), transforming their identities and developing new relationships. By comparing the life stories of two individuals, we identify two relational paths establishing different types of relationships with community-based entrepreneurial ventures. In the first path (embedded transformation), reflection on trust and mutual recognition of expertise enables an external scientist to join the entrepreneurial venture. In the second path (institutional facilitation), reflection on public transparency and the constitutional roles enables a head of a semi-public organization to shift the policy approach from viewing entrepreneurs as “beneficiaries” to recognizing them as “rights-holders.” In both cases, relational reflexivity connects collective action to broader processes of social change.