The high incarceration rate and systemic racism in the United States, along with entrenched social barriers, highlight the need for creative solutions to help formerly incarcerated individuals (FIIs) reintegrate successfully. This paper highlights social entrepreneurial ventures (SEVs) as powerful agents of social change, underscoring the significance of holistic approaches in successful reentry and transformation of FIIs. We delve into the potential of SEVs as catalysts for social justice within the critical HRD (CHRD) framework, examining SEV’s role in advancing learning, challenging power dynamics, empowering marginalized communities, and propelling grassroots-led social change. In doing so, we also emphasize the significance of experiential learning and dialog in cultivating collective knowledge and action within these social movements. We analyze the structural, organizational, and individual factors that demonstrate how HRD and social entrepreneurship complement and broaden modes of engagement. Ultimately, we highlight the promising synergy between SEVs and the CHRD perspective, presenting a transformative approach for both HRD scholars and practitioners and argue that by embracing the values of empowerment, equity, and social justice, HRD can play a pivotal role in fostering more inclusive, equitable, and empowering organizational landscapes.