Studies indicate that more male entrepreneurs are pursuing business ventures than their female counterparts. Latterly, there has been increased research interest in female entrepreneurs and their positive contribution to the retail economy. The main purpose of this study was to examine how some specific masculine traits can be enculturated into individuals (i.e. female entrepreneurs). The study also reviewed literature that discussed reasons which hinder female entrepreneurs in the retail world. The reasons range from being risk averse, being too agreeable and being overly anxious about failure. Through qualitative research exploration of female entrepreneurs, semi-structured interviews were undertaken to examine and understand their experiences. Themes which emerged from questioning the ten female entrepreneurs enabled the researcher to construct a theoretical framework. Analysis of the content findings showed that female entrepreneurs were indeed willing to adopt specific masculine traits. The result of this investigation is that through implementing specific masculine traits, female entrepreneurs have greater chances of success in their retail businesses. Although the research presented valid findings regarding the benefits of masculine traits on the retail industry, the research was limited by the sample size and the location of the research. This contribution remains unique in the way that it provides valuable information to the retail industry about the process of overcoming failure through enculturating masculine traits into female entrepreneurs.