This chapter highlights the challenges of women business owners in sub-Saharan African (SSA) using in-depth interviews from four different countries. The primary aim of the chapter is to pinpoint shared challenges of women entrepreneurs and/or business owners drawing upon their narratives and attributions. 1 The chapter unpacks four critical dimensions impacting upon the similarities and/or differences in experiences – notably owner’s background (nationality, ethnicity, education, family etc.); prior motivations (why they chose to start up); challenges (including start-up capital, government regulations, personal achievements), and plans for the future.