The trend of female self-employment in Italy is stable, with a low level of participation which confirms the prediction of economic theory on discrimination. We contend that gender discrimination alters the distribution of entrepreneurial talent between employees and self-employed workers. This gives rise to the prediction that the self-employed women are less likely to survive when self-employed than men because the lesser entrepreneurial talent of women will increase their risk of failure. Applying Markovian analysis to ISTAT’s labor market transition matrices we verify this prediction: Many women try to set up on their own, but they fail to remain self-employed both because their lesser entrepreneurial talent and because they try to become entrepreneurs without any previous experience of work.