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This paper examines the Youth Juvenile Justice Fellows program, a nine-month, out-of-school diversion initiative designed to center the voices, agency, and aspirations of justice-impacted Black male youth ages 14–18. Grounded in Hip Hop pedagogy, and community cultural wealth, YJJF provides bi-weekly sessions that integrate mentorship, advocacy training, and financial literacy. Anchored by the youth-adopted mantra “Standing on Business,” the program redefines Black masculinity through dignity, purpose, and self-determination. This study draws on testimonies from six youth participants who engaged in critical dialogue, lyrical analysis and workshops led by local entrepreneurs and justice-impacted mentors. The session includes youth presenters, underscoring the centrality of lived experience in educational justice work.