This article contributes to the civic identity development literature by exploring how a scholarship program emphasizing entrepreneurship and economic revitalization can facilitate engagement across difference in pursuit of shared anti-poverty commitments. Drawing on theories of entrepreneurial action, civic identity development literature, and a mixed methods approach, we propose a framework for how students conceptualize identity, race, and poverty as "entrepreneurs of connection." The role of uncertainty is central to entrepreneurial action and a hallmark of community engagement. Combining an inquiry into their own sense of identity in relationship to their peers and community partners, students contribute to the development of the entrepreneurial ecosystem by making connections at the interpersonal, organizational, and systems levels. Students merge an understanding of their personal identities and situational context to build trust with diverse peers and community partners. Entrepreneurs of connection take action with community partners to pursue innovative solutions with a focus on social change.