Paradox is increasingly being used in management research due to escalating technological change, global competition and workforce diversity (Lewis, 2000). While it has been recognised that the entrepreneurial process is also paradoxical and is especially untidy, non-linear, inconsistent and unpredictable in nature (Ropo et al., 1995), there have been few developments in entrepreneurship research on this. This paper attempts to address this by mapping some of the paradoxical patterns in the entrepreneurial process as entrepreneurs seek to create predictability and value out of the ambiguity, chaos, and uncertainty. In so doing, it also seeks to understand the complex paradox of why entrepreneurs have to fail before they can succeed and why, even after succeeding, they can still continue experiencing failure.