Most Caribbean NPOs operate like traditional NPOs, non-business-like and dependent on donor organisation for operational survival. However, the evidence demonstrates that traditional NPOs with entrepreneurial leaders, once provided with business management training concepts, operate business-like and invest in earning income. Entrepreneurial NPOs have a greater potential of using business management strategies and demonstrating accountability with self-generated funding, indicating the full conceptual position of the EMES school of thought on social entrepreneurship [SE] and social enterprises’ best practices. Further, similar to international experiences, appropriate institutional support enables Caribbean entrepreneurial NPOs’ operational and financial self-sustainability enabling their creation of sustainable social impact. These findings add to the knowledge of SE from conceptual and contextual perspectives, with demonstrated implications and associated recommendations for academia, Caribbean governments, and the business and social sector.