Entrepreneurs may transform prior experience into knowledge that furthers their subsequent entrepreneurial behaviour in different ways (Politis, 2005). Habitual entrepreneurs may learn and accumulate human capital from PBOE ‘success’ firm closure and/or PBOE ‘failure’ firm closure (i.e., for economic and/or non-economic reasons). Entrepreneur experimental learning experience from PBOE may, in part, enhance subsequent entrepreneur opportunity creation and discovery, as well as superior firm development. In this chapter, we focus on entrepreneur rather than organization learning. The article by Ucbasaran et al. (2003) is a theory-building study that builds upon insights from human capital theory and RBV of entrepreneurship. Adopting theoretical sampling of eight habitual starter and acquirer entrepreneurs, this study explored whether the nature and extent of entrepreneurs PBOE shaped their subsequent behaviour and learning. Similarities and differences between habitual starter and acquirer entrepreneurs are highlighted. Several theoretically and empirically derived propositions are developed.