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Drawing on existing research on prison sport and recent interest in entrepreneurship among people with criminal records, we administered a novel survey with an embedded conjoint experiment to a national sample of 1,100 U.S. adults in 2025 to determine what factors shape choices for personal trainers and whether factors driving overall preferences—such as trainer credentials and references, mode of instruction (in-person vs. online), session price, and trainer race—operate differently when the trainer is presented as having a prison record. Consistent with prior research on reentry, employment, and prison stigma, respondents preferred trainers with other workout backgrounds over those who began their training in prison. Respondents also generally preferred training sessions that were less expensive, in-person, and from qualified trainers. However, when assessing trainers with prison records, respondents preferred those who offered online sessions and charged a higher session price. Findings suggest that while barriers to self-employment remain for people with prison records, certain marketing and service delivery strategies could increase success.