This chapter aims to analyze the influence of entrepreneurial skills and contextual factors on the promotion of entrepreneurship. To this end, the factors analysed in this chapter are grouped into three levels: individual, university, and government. In addition, all the factors are examined from a multi-country perspective, grouping the economies in function of their levels of incomes. Thus, the chapter offers a comprehensive revision of the main factors -at different levels of analysis and from a geographical perspective- that influence the development of entrepreneurial initiatives. In addition, sustainable entrepreneurship, which integrates economic, social, and environmental aspects, is also analyzed as a way to stimulate economic development. The theoretical arguments are reinforce through the employment of the specific data obtained from the international reports of Global Entrepreneurship Monitor (GEM) and Global University Entrepreneurial Spirit Students Survey (GUESSS).