Risk taking is fundamental to entrepreneurial activities and a central theme of the entrepreneurship literature. However, research on the risk taking propensity of entrepreneurs has met with virtually no empirical evidence on how socio-cultural factors influence on taking entrepreneurial risk in the context of South Asia where entrepreneurs consistently face challenges of high uncertainty due to socio-cultural and politico-economic complexity and instability. Purpose of this paper is to address this paradox by examining entrepreneurial risk through the lenses of socio-cultural, politico-economic and decision making. Given the self-evident that nature of complexity, irrationality and uncertainty in this context, a sophisticated exploration of entrepreneurial social reality of risk taking and management requires the fundamental philosophy of subjectivism and therefore this study adopts qualitative inductive case study methods in a sample of Sri Lankan entrepreneurs. The study found that entrepreneurs do indeed use their social and cultural understanding to a great extent in their decision making.