This article addresses a research gap in conceptualizing ecosystem approaches to social entrepreneurship development and scaling social innovation. Towards that end, we performed analyses on 268 social startup projects in Hong Kong, examining target beneficiaries and social issues. Semi-structured interviews were conducted with 33 founders to collect information about critical incidents that took place after they received seed funding from an incubator. The interviews revealed distinctive struggles among social entrepreneurs including business modeling for blended value and for low-income markets as well as organizational field dynamics surrounding contested issues. We conclude by offering propositions for social enterprise ecosystem research with an issue field lens.