The shortages of entrepreneurial skills, both perceived and actual, have lowered the rate of opportunity-driven women’s entrepreneurship. This paper contributes to the literature on entrepreneurship, gender and development with a theoretical and empirical analysis linking gender differences in entrepreneurial outcomes to skills and business training. The role of skills, including self-confidence, and training for the entrepreneurial performance is tested on a survey of urban entrepreneurs in Swaziland. The results help explain why narrow business training programs for female entrepreneurs have often limited success in improving performance of women-run firms. Training programs for women entrepreneurs encompassing advanced business and technical (e.g. hard) skills as well as networking and confidence building (e.g. soft skills) could be more effective.