This chapter explores the origins and development of Hang Time, a community-driven reentry program co-founded by Charlie Grady and Mike Gustafson. It traces Charlie’s experiences with the PBJ program, where he identified the shortcomings of traditional, metrics-focused reentry initiatives. Frustrated by the slow pace of meaningful change, he sought to create a program centered on sustainable community relationships and mutual respect. The chapter details Hang Time’s core values, the structure of its community forums, and real-life interactions that highlight its impact. Emphasizing trust, accountability, and empowerment, Hang Time ensures that promises are kept and that individuals reentering society have a say in their journey, free from excessive judicial oversight. The program’s success is rooted in its commitment to treating every participant with dignity and fostering genuine, long-term support networks.