Will significant numbers of today's youth become able to succeed in careers that require entrepreneurial capacities? Who among today's youth will have the talent, skills, knowledge, and drive needed to become successful entrepreneurs? To answer these questions, it will be necessary understand the developmental bases of individual and ecological variables linked to successful entrepreneurship and their interrelations over the course of the first decades of life. Accordingly, we use a relational developmental systems approach as a lens to examine what is currently known about the development of entrepreneurship during adolescence. We present an approach to understanding the mutually influential relations between youth and contexts that eventuate in the development of entrepreneurship capacities during this period of life. We also examine how the evidence from such research could inform the design of innovative educational programs that promote interest and skill in entrepreneurship among youth.