Since women are half as likely to start a business as men, this study aimed to investigate the perceptions and gender-based obstacles female business owners encountered in the field of entrepreneurship. This topic was examined by interviewing 10 female and 10 male entrepreneurs about how they came up with the idea for their business, prior educational and industry experience, challenges, financing their venture, perceived traits of a successful entrepreneur, and how networks, mentors, and family influenced the process of starting a business. The findings of this study are that women tend to be small business owners and pursue female-oriented industries. In addition, the results show that access to outside funding is more difficult for women because of their own aversion to risk and disconnect between female founders and the potential investor pool. Interviews demonstrate the struggle and societal pressures women feel in balancing work and family. An unexpected discovery of the research is the importance of having a supportive spouse or partner for married entrepreneurs. This study shows the need for future research into the effects of gender and age in pitch competitions, divorce among entrepreneurs, and the relationship between gender and risk aversion.