Purpose/Objective: Entrepreneurship is increasingly emerging as a viable employment option for many people with disabilities. It provides opportunities to develop interests, skills, and passion for starting a business. We conducted multiple interviews with various stakeholders to identify the perceived supports and barriers that people with disabilities encounter in the process of pursuing entrepreneurship. Research Method/Design: Individual interviews included 20 entrepreneurs with disabilities, 6 service providers, and 5 school administrators. This qualitative study used a constructivist grounded theory approach to shape the process of data collection, analysis, and theory building. Results: People with disabilities interested in pursuing entrepreneurship benefit from facilitators such as social support, mentoring, and access to space, equipment, and money. Personal qualities include their desire to be “my own boss,” help others, earn money, creativity, persistence, and flexibility. On the other hand, they may face several systemic barriers, such as the lack of infrastructure to set up the business, discrimination, lack of formal support from Vocational Rehabilitation counselors or their school settings, and/or lack of money. Conclusions/Implications: The systemic barriers can make it difficult for entrepreneurs to start and/or continue to operate their businesses. We discuss the implications of the findings for the development of entrepreneurship training for youth with disabilities and offer recommendations for future research and practice in the rehabilitation field.