In the years of the financial and sovereign debt crisis in Greece, many viable businesses that are facing financial difficulties are led to liquidation rather than timely restructuring, with very few entrepreneurs having a second chance. This corporate failure faced by Greek companies in recent years may have been caused by either endogenous or exogenous factors or a combination of these two. In this paper we investigate the factors (economic, social and political) that will help to facilitate entrepreneurs' access to a second and third opportunity, taking also into account socially vulnerable groups such as disabled people and women entrepreneurs. Moreover, we try to find the characteristics that would encourage honest bankrupt entrepreneurs to a second business venture and the sectors where a second chance may have increased chances of sustainability in Greece. The aim of our research is to lead Greece to higher levels of self-employment, reduction in unemployment, and exit from the crisis.