Two women who once made headlines for their criminal convictions have transformed their lives and are now helping Boston teenagers build entrepreneurial skills and launch their own businesses. Dr. Jamila T. Davis and Dr. Ayana K. Bean, both featured on BET’s “American Gangster: Trap Queens,” have established the Boss Up Boston program, which has already helped teens create over 40 businesses in just eight weeks.
From Federal Prison to Community Leadership
Dr. Jamila Davis served 12½ years in federal prison for bank fraud. During her time behind bars, she developed the Voices of Consequences Enrichment Series, a healing curriculum for incarcerated women. This program has since been adopted by the Bureau of Prisons and approved for First Step Act time credits.
“I created curriculum in a prison cell,” explains Dr. Davis. “My lack of financial literacy and doing the wrong thing landed me in federal prison. This work—this movement—is about righting those wrongs and making sure the next generation doesn’t have to fall to rise.”
Boss Up Boston: Teaching Teens to Build Their Own Future
The Boss Up Boston program launched in 2024 as an earn-while-you-learn entrepreneurship training initiative for youth ages 14 to 18. Despite starting with no dedicated funding, Davis and Bean partnered with the City of Boston to provide stipends to students through the SuccessLink Summer Employment Program.
Using a curriculum based on “Boss Up! The Official Guide for Teen Entrepreneurship” created by Dr. Davis, students have successfully launched businesses ranging from beauty brands to catering companies, merchandise lines, and wellness products. The program operates under Partners Uplifting Our Daughters and Sons (PUDS), where Dr. Davis serves as Program Director.
Building Financial Literacy and Second Chances
Dr. Ayana K. Bean, who also served time for financial crimes, returned from prison determined to help others avoid similar mistakes. Through her foundation, A Year And A Day, she focuses on financial literacy, reentry support, and empowerment for justice-involved women.
“We came from systems that weren’t built to heal us. But instead of being erased, we chose to lead,” said Dr. Bean. “Now we’re building new systems—ones that pour into Black girls, urban youth, and women who need a second shot.”
Recognition and Expansion of a Grassroots Movement
The impact of Boss Up Boston has earned recognition from city officials. Dr. Bean received the Extraordinary Women Award, along with two youth entrepreneurs from the program, Rex and Maliyah. Due to its success, the program has expanded into a year-long model serving an additional 20 students.
Fellow justice-impacted leader Syrita Steib, Executive Director of Operation Restoration, provided initial seed funding and mentorship to help launch the pilot program. This community-based approach has created a powerful network of volunteers and mentors committed to youth development.
Transforming Personal Setbacks into Community Assets
Both women have earned impressive credentials since their release. Dr. Davis completed her Ph.D. through academic research and study, while Dr. Bean recently received an honorary doctorate recognizing her impact on urban communities, financial empowerment, and second-chance leadership.
“This isn’t a program. It’s a movement,” said Dr. Davis. “We’re proof that with lived experience, vision, and a community-first mindset, you can flip the trap and build legacy.”
A Blueprint for Community-Led Change
Today, Davis and Bean serve as national voices for justice-impacted leadership. Through the Institute of Research for Social Justice in Action (IRSJA), they train credible messengers, youth leaders, and community builders across the country.
Their work demonstrates how lived experience can become a powerful tool for community transformation. By teaching entrepreneurship skills to teens, they’re helping young people avoid the pitfalls they once faced while building economic opportunity in underserved communities.
Those interested in learning more about the Boston Boss Up Teen Entrepreneurship Program can visit Partners Uplifting Our Daughters and Sons at www.eglpud.com.
