This study explores the roles of female business owners and managers in a transitioning post-socialist economy. It draws on three case studies of media firms founded in the early 2000s and 2010s in Kyrgyzstan by women. Kyrgyzstan is a curious context for management-related gender issues since women are highly literate and highly economically active. Yet, female media business leaders are still uncommon. The women that belong to the first generation of urban business owners seek legitimation. It is particularly acute for the businesswomen that are engaged in cultural production such as media since they are rare birds compared to their female counterparts doing trade and commerce. Kyrgyz female business owners engage in a sophisticated game of being a commercially successful manager, and at the same time, artfully downplaying one's career achievements in front of the social circles. This paper explores women's roles through their education, family and marital status, and class awareness.