This research aims to enhance our understanding of the relationship between assistive technologies (ATs) and disabled entrepreneurs, specifically who these latter are and how they perceive the value of assistive technologies. Nineteen in-depth semi-structured interviews were carried out remotely with disabled self-employed individuals from France to answer the research question. Semantic analysis was used to make sense of and synthesize the main emerging ideas. The results identified five themes grouped into three main categories. The first is related to the description of the disabled entrepreneurs’ profile, which goes beyond the classic categorization of entrepreneurship. They have developed through their experiences some specific entrepreneurial competencies: personal self-knowledge, self-management, self-awareness, self-assertion, resilience, persistence, courage, emotional intelligence, innovation and adaptability. The second is related to the perceived value of assistive technologies to disabled entrepreneurs and their impact on their daily life. In fact, the disabled entrepreneurs’ use of assistive technologies was found to have implications for the enhancement of their social inclusion and quality of life by gaining more independence, self-control, self-confidence and self-esteem, as well as knowledge and skills. Finally, despite the personal and professional benefits of assistive technologies, issues of digital accessibility were noted as challenges (desires for future assistive technological devices).