This paper examines job growth expectations of young entrepreneurs in two small-island Caribbean states, Jamaica and Trinidad and Tobago, using data from the 2013 Global Entrepreneurship Monitor's Adult Population Survey. Results from regression analyses reveal that job growth expectations of young Jamaican entrepreneurs were lower compared to their counterparts in Trinidad and Tobago. Young male entrepreneurs are more likely to increase job growth compared to young female entrepreneurs in both islands. Moreover, the analysis indicated a positive relationship between educational levels of young entrepreneurs and projected job growth in both countries. However, the benefits of education were different in these countries: if the level of education is increased by the same degree in both countries, job growth is expected to be relatively higher in Jamaica versus Trinidad and Tobago.