Racial discrimination is a pervasive societal issue that profoundly influences the opportunities and experiences of racial minorities. While in this context entrepreneurship is often framed as a necessity-driven response to structural disadvantages, this perspective overlooks the diverse motivations and pathways of racialised actors. Drawing on 43 podcast interviews and 24 in-depth follow-up interviews with U.S. Black entrepreneurs, this study examines how experiences and interpretations of racial discrimination shape entrepreneurial motivations and venture trajectories. We find that discrimination perceived as a personal threat often drives individuals to “break free” from workplace inequities, whereas those interpreting discrimination as a structural issue are motivated to “break up” systemic barriers, fostering collective advancement for the Black community. Furthermore, shifts in entrepreneurial motivations frequently occur, with initial self-oriented goals evolving into prosocial aspirations. Our findings challenge necessity-driven accounts, highlighting the dynamic interplay between racial discrimination, agency, and entrepreneurship as a vehicle for both personal emancipation and community empowerment.