To capture the talents of the next generations in new venture creation and to maintain the levels of entrepreneurship in our society, a vibrant “pipeline” of potential entrepreneurs is required. Previous research has shown this pipeline may still be weak, especially for women entrepreneurs. This paper explores the relationships between gender, entrepreneurial education, and entrepreneurial self-efficacy on entrepreneurial intentions and behaviors using the data from different sample groups in three different stages of education and career development: middle and high school students, MBA students, and Early Career adults. The results of our analyses underscore the importance of entrepreneurial self-efficacy as a key component in understanding entrepreneurship interest and actual career choice. The positive influence of entrepreneurship education on self-efficacy proved stronger for women than for men. Implications for entrepreneurship educators as well as study limitations and areas for future research are discussed.