This article discusses lessons learned from a social enterprise project supporting sustainability education in central North Carolina (U.S.A.). Since 2011, Eco-Cycle,1 a retail shop featuring creative-reuse has provided support for a community meeting space that offers weekly environmental education workshops. Many approaches to social justice-oriented green initiatives in the United States emulate urban agriculture models and tend to be grant-dependent in early years, only achieving economic sustainability with difficulty. In contrast, our non-profit co-op of upcycler crafters and vintage vendors grew out of production and marketing of upcycled rain barrels, based on a social enterprise approach rather than a traditional model. I discuss the stepping-stones to this venture, which originated through a neighbourhood energy conservation initiative, followed by alliance-building with non-profits to promote green job creation. I relate the complications and surprising forms of synergism emerging from the social enterprise approach to social theory on cooperatives and community-based development models.