The chapter reviews existing literature to provide insights into the impact of gender and culture on women entrepreneurs in sub-Saharan Africa. It discusses how gender and culture influence business growth, resilience, and stakeholder management. The chapter further establishes that business growth in women-led entrepreneurial ventures is relative and may not be measured by conventional outcomes. We also found that educated women in Africa, with adequate social capital, are taking up entrepreneurship, but the sociocultural and economic context within which they operate continues to challenge their enterprises. This review recommends further empirical studies on women’s entrepreneurship and the role of “charismatism” as a driver of women’s entrepreneurship in Africa. It also recommends studies into how societal stereotypes and expectations have evolved and how this enables or impedes women entrepreneurs.