This qualitative case study examined the key components and characteristics of an entrepreneurship training and mentorship program for incarcerated males. For the previously incarcerated, barriers to employment serve as an impediment to financial stability when transitioning back into the community. To address obstacles to employment, entrepreneurship training programs have emerged, which focus on preparing returning citizens for self-employment opportunities as an alternative to private employment. In order to understand what constitutes effective training for this marginalized population, this study evaluated the key factors and features identified by those closely associated with a training program. The research study collected and compared data from multiple sources, including a review of artifacts as well as semi-structured interviews with both formerly incarcerated participants and program volunteers. The research methodology resulted in three main study findings: 1) the training program had a multi-faceted structure, 2) the program had a visible impact on the local community and participants, and 3) distinct motivating factors and obstacles existed that impacted participation. In addition to offering a diversity of learning pathways, individualized support services, and technical knowledge, the program was collaborative and developed important soft skills to support participants in the transition back into society. The strength of the organization's leadership and the program's mentorship component were lauded by both participants and volunteers as being a key factor in providing a stable, supportive social network for the returning citizen. The training increased engagement, reduced stereotypes and biases while promoting a diversity of voices that encouraged creative solutions to business and societal problems. The program was not without obstacles, as limited participant resources, financial barriers, access to the incarcerated, time and space limitations, inmate-engendered issues, and lack of support from the correctional environment impacted effectiveness. Based on the study findings, ten recommendations emerged for actionable solutions and further research. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]