ABSTRACT The current entrepreneurship research has primarily focused on external environmental factors that influence enterprise development in developed economies, whilst studies from developing economies are lagging. Yet, evidence from the World Bank and Global Entrepreneurship Index suggest that entrepreneurship practice in developing economies has peaked. Using semi-structured interview data from 20 entrepreneurs in The Gambia, we examined their motivations for entrepreneurship, the market opportunities and challenges hindering enterprise growth. We found the factors influencing motivation to be individual (necessity, poverty, job creation, personal knowledge, and experience) and contextual (opportunity recognition, ethnic and religious norms). Interestingly, three forms of opportunities were identified: entrepreneurial networks, competitive market, and discovery. Nonetheless, the entrepreneurs faced individual challenges – insufficient finance and unskilled staff – and contextual limitations such as political change, limited government reforms, high taxes, high business cost, and market uncertainty. We offer critical insights into individual and contextual motivations for entrepreneurship, extending the current discourse. In addition, we expose specific dynamic market influences for enterprise development in a developing economy.