We worked with Men on the Side of the Road (MSR) in Windhoek, Namibia, to create an entrepreneurship training program, “Pathway to Self-Employment.” We created this program after interviews with self-employed MSR members and entrepreneurship professionals as well as through the experience of helping an MSR member in the implementation of his business. We piloted our training program and made changes based on feedback from MSR members and staff. The “Pathway to Self-Employment” will be implemented by MSR and become a gateway to further entrepreneurial courses in the Windhoek-area.