This study explores how the nature of an entrepreneurship environment may provoke desired entrepreneurial success. To illustrate this, our study investigates Puerto Rico’s (P.R.) unexplained stagnant entrepreneurial environment when compared to other high-income countries. A quantitative study using Partial Least Squares (PLS) was conducted to determine: How and to what extent do systemic and individual factors— mediated by inter-organizational and individual social networking activities—impact the likelihood of entrepreneurial success? Our findings reveal that systemic factors in P.R. as a whole are not working as suitable sources for the complementary relationships needed to create an environment conducive to successful entrepreneurship. Meanwhile, Puerto Rican entrepreneurs are not using networks efficiently to overcome the inadequate institutional structure. Therefore, to nurture a successful entrepreneurial environment, policy makers must design a better interconnected entrepreneurial system that will work in harmony with entrepreneurs; while entrepreneurs in turn must be taught to effectively use their networks.