In this study, we examined how an investor’s expertise can moderate female-led enterprises' challenges when achieving follow-up investments. Prior research indicates that female entrepreneurs often face a disadvantageous position within the investment ecosystem compared to their male counterparts. We investigated whether the professional competence of investors, rooted in their diverse experiences, could help alleviate the challenge of female entrepreneurs when they attempt to achieve follow-up investment. This study classified investors' competencies based on their experiences at the company level, industry level, and multinational level. With these experiences, we examined the moderating effects of these experiences on the difficulties faced by female businesses. We conducted an empirical analysis using data from 4,663 companies that secured investment between 2005 and 2022. Our findings reveal that female businesses indeed face difficulties in securing follow-up investments. However, these difficulties are less pronounced when investors have prior investment experience in the same industry and foreign markets. To summarize, this research highlights the investment hurdles female entrepreneurs face and suggests that investors, armed with a broad range of experiences, can play a pivotal role in aiding the success of female entrepreneurs.