The purpose of this article was to present a description and first-stage evaluation of the impact of the Ice House Entrepreneurship Program on the learning experience of participating prerelease inmates at a Mississippi maximum-security prison and their perception of the transfer of skills learned in program into securing employment upon reentry. The Ice House Entrepreneurship Program is a 12-week program facilitated by volunteer university professors to inmates in a prerelease unit of a maximum-security prison in Mississippi. Participants’ perspectives were examined through content analysis of inmates’ answers to program Reflection and Response Assignments and interviews. The analyses were conducted according to the constant comparative method. Findings reveal the emergent of eight life-lessons and suggest that this is a promising approach to prison programming for prerelease inmates. This study discusses three approaches to better prepare inmates for a mindset change. The rethink, reform, and reenter approaches help break the traditional cycle of release, reoffend, and return.