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This manuscript focuses on factors — in particular, political credential and mobilization of personal contacts — associated to becoming a cuentapropista, namely a self-employed worker in the emerging private sector. Data were collected shortly before the launch of the recent reforms plan aiming at revitalizing the market-oriented reforms of the 1990s. The results suggest that being a member of the PCC is negatively associated to entering in the private sector. Older individuals and recipients of remittances have instead a higher probability to become a self-employed worker. Moreover, the results provide some support to previous findings that turning to personal ties — especially if strong — to successfully complete a job search, is a common practice in Cuba.