This paper explores how firm characteristics, entrepreneur profiles, and institutional framework either strengthen or diminish the relationship between systemic and individual factors and entrepreneurial success in Puerto Rico’s (P.R.). Building on our earlier qualitative research a quantitative study using a structural equation modeling (SEM) approach was conducted to determine: How and to what extent do systemic and individual factors —moderated by institutional framework and firm and entrepreneur characteristics— impact the likelihood of entrepreneurial success? Our findings reveal that firm characteristics, entrepreneur profile, and institutional framework will moderate the relationship between systemic and individual factors and entrepreneurial success, with individual and inter-organizational networks as mediators. Therefore, we can argue that differences in the likelihood of entrepreneurial success exist based on the group’s characteristics. Policy makers and entrepreneurial stakeholders need to be aware of such differences among groups to develop their strengths and use it to spur entrepreneurial activities.