This paper examines the rise of social enterprise in relation (and in response) to the contemporary nexus between education and work. Contextualising social enterprise within the broader trend toward private influences in education, the paper explores how diffuse networks driven by both market ideals and a social conscience are shaping new sites of education and work on the margins. Drawing on in-depth research undertaken on the experiences of homeless street press sellers of the social enterprise "The Big Issue," I bring focused attention to the lived experience of these transformations in policy and practice. The analysis reveals how entrepreneurialism intersects with precarious poverty to frame sellers' cultivation of their skills and techniques as enterprising workers on the margins.