The Prison to Proprietorship Act would establish a new program requiring the Small Business Administration to provide entrepreneurship counseling and training services to incarcerated individuals in federal prisons. The program targets people held in minimum, low, and medium security federal facilities, offering them business planning assistance, financial literacy training, five two-day classroom sessions, and one-on-one mentoring to help them start or expand small businesses after release. Services would be delivered through existing women's business centers and small business development centers, prioritizing those closest to each federal prison, and participants would receive a certificate upon completion. Incarcerated individuals eligible to be released within 18 months would receive priority access, and they can continue receiving services after their release. The bill requires the Small Business Administration to submit annual reports to Congress on program participation, effectiveness, and participant demographics, and authorizes funding to reimburse the centers for providing these services.