This dissertation examines cultural understandings and lived realities of entrepreneurship across South Africa’s economic landscape, comparing the experiences of Cape Town’s Black entrepreneurs in under-resourced townships to those of White entrepreneurs in the wealthy, high finance business district. Based on 13 months of participant observation and interviews with 60 entrepreneurs, I find major differences between these groups of entrepreneurs, which I explain in three independent analyses that together form this dissertation. The first analysis examines the entrepreneurial motivations of Black entrepreneurs in Khayelitsha, Cape Town’s largest township. This analysis gives insight into expressed cultural values of entrepreneurship beyond a priori neoliberal analytical frameworks. The second analysis compares the material resources that Black entrepreneurs in Khayelitsha and White entrepreneurs in downtown Cape Town require for their businesses, and the mechanisms through which they secure these resources. This analysis demonstrates how historical structures of economic inequality affect entrepreneurial strategies. The third analysis assesses the non-material obstacles and challenges that both Black entrepreneurs in Khayelitsha and White entrepreneurs in wealthy areas of downtown Cape Town face in initiating their business ventures. This analysis highlights the importance of cultural capital to entrepreneurship and explains how non-material obstacles differ for entrepreneurs in different positions of societal power. Taken together, my findings contribute to two long-established lines of anthropological scholarship on entrepreneurship: (1) the moral values and understandings of entrepreneurship, and (2) the strategies and practices of entrepreneurship. I demonstrate the need to expand anthropological understandings of entrepreneurship to better theorize diverse economies, localized understandings and values of entrepreneurship, and the relationship of entrepreneurship to notions of economic justice. Yet, through comparative analysis I also demonstrate that diverse and localized values of entrepreneurship must be considered within the context of societal power structures; such context allows scholars to assess if and how diverse entrepreneurial values have the potential to make broad-scale social and/or cultural change. As such, I argue for the importance of putting these two streams of anthropological research into conversation with one another in order to gain a more holistic understanding of the relationship between the cultural meanings and the practices of entrepreneurship.