This talk reflects on 15 years of friendship and ethnographic conversation on mass imprisonment in the Andes between Arbolito, Nunez's long-time collaborator, and Nunez. It explores the role of prison economies in Latin American carcerality on the one hand, and the use of race and technology in small-time financial crimes on the other. Through a focus on life experiences of organized crime and incarceration, this talk attempts to reframe the prison system as a space of entrepreneurship within an economy of exclusion and inequality, rather than seeing it exclusively as a control mechanism or penal institution.