Prior research identified two important (dis-)advantages in entrepreneurs’ networking and access to funding: the entrepreneurs’ social networks at the inception of their ventures and their gender. However, to date, both have been analysed in isolation, neglecting their interplay. Based on a qualitative comparative case study with 52 entrepreneurs, we identify three networking approaches: calculated networking, trusted networking, and serendipitous networking. The former two allow entrepreneurs to achieve superior outcomes—but only for those with relevant initial networks. Female entrepreneurs, in particular, experience fundraising challenges through calculated and serendipitous networking approaches, leading to comparatively inferior outcomes. Trusted networking, on the other hand, provides equally beneficial outcomes for both genders; however, it requires a relevant initial network. Interestingly, we found that female entrepreneurs face different biases and concomitant disadvantages depending on their initial network.