From 2021-2025, University of Wisconsin-Madison Extension led a cross-sector collaborative to solve a multi-part problem in Wisconsin: inequities in both entrepreneurship and incarceration, alongside high recidivism. Responding with entrepreneurship education for justice-impacted state residents, Extension educators followed the same steps their participants were learning to grow the program. This paper describes the effort through typical Extension program development steps as well as entrepreneurial language. Comparing the two shows that common Extension skills are well suited to social entrepreneurship, which creates a community benefit from new funding and partners. It ends with a discussion of lessons learned and suggestions for trying again.