We compare nine African countries to see how historically-embedded institutional frameworks and other environmental conditions affect the likelihood of applying individual resources into most productive forms of entrepreneurial start-ups. Accordingly, we develop hypotheses about how historical and institutional factors influence occupational choices related to entrepreneurship. We utilize the 2013 Global Entrepreneurship Monitor (GEM) individual level data for African countries to test these ideas. We run regression models to explore how these factors explain the likelihood of being engaged in a start-up activity, differentiating between necessity and opportunity driven entry and between high and low aspirations entry.