The current economic climate demands more innovative approaches to increasing labor market participation for people with disabilities. Social entrepreneurship offers one alternative pathway to employment. However, little is known about the motivational and attitudinal factors influencing social entrepreneurship for people with disabilities. Using empirical data from focus groups comprised of social entrepreneurs with disabilities, and interviews with key stakeholders working in the fields of policy, disability, and business, this research frames its analysis in the intersection of disability studies and entrepreneurial studies to explore: what motivates people with disabilities to pursue social entrepreneurship, if they continue to encounter attitudinal barriers and discrimination, and whether motivational and attitudinal factors affect their social entrepreneurship. Findings indicate that despite social entrepreneurship having been promoted as a strategy for circumventing employment discrimination, the individuals with disabilities in this research continued to encounter attitudinal barriers and discrimination affecting their employment decisions. Future research should focus on interrogating what might be gained in the spaces where need and opportunity intersect and exploring the extent to which motivations overlap for social entrepreneurs with disabilities in theory, policy, and practice.