In Chile, during the past two decades several reforms have been implemented with a goal of dismantling institutional barriers constraining equity funding along with the allocation of government investment in public financing programs. The purpose of this chapter is to analyze how public policy may influence the cultural legitimacy of entrepreneurship in a region. Understanding how entrepreneurship policy and programs, and specifically the unique Start Up Chile initiative, may impact the culture towards entrepreneurship and the perception of entrepreneurship as a career choice. The main findings suggest that the introduction of Startup Chile resulted in a spike in interest in Chile as an entrepreneurial ecosystem.