There are two highly successful community based organizations (CBOs) in Barbados, the Pinelands Creative Workshop and the Israel Lovell Foundation. Both of these entities are linked to impoverished neighborhoods and over the past 20 years have been successful in social empowerment and transformation through the strategic and creative use of the arts. Additionally, both these CBOs have strong affiliation with the political representatives and leaders of their constituencies. This combination of CBOs, the arts and political support has led to a model that is now being duplicated throughout the rest of Barbados and the Caribbean. Of particular interest is the fact that both these groups are now engaging entrepreneurial development as part of their new mandate and social agenda. This paper will examine the evolution of these CBOs and their models for achieving social transformation. Much of the research will be primary drawing directly from the source of their leadership and members as well as the author’s experience in managing their arts projects through Barbados’ Cultural Action Fund. It is hoped that this attempt to examine this model will serve to inspire further research.