Crowdfunding as a digital tool may have the potential to “democratize” the entrepre-neurship funding process as it provides further access for both women entrepreneurs and women investors to participate in the funding process (Josefy, Dean, Albert, & Fitza, 2017; Marom, Robb, & Sade, 2014). Nonetheless, how experts perceive and women entrepreneurs experience the allegedly neutral digital environment of crowdfunding, remains under-investigated. We position ourselves in a context-specific study in Italy. First, we conducted semi-structured interviews with experts of various crowdfunding platforms in Italy to cap-ture a national overview of crowdfunding including gender influences and cultural stereo-types. Second, this was complemented by the inside perspective of in-depth interviews with Italian women entrepreneurs all conducting crowdfunding campaigns. Experts reveal that the Italian context provides a challenge for crowdfunding as the concept is little known and cultural preconceptions exist. Both, experts and women entre-preneurs, mainly believe that in crowdfunding only idea and personal commitment count, independent of gender. Still, there were several barriers for women entrepreneurs for which they developed particular coping strategies. These strategies all foster individualistic tendencies. Additionally, a key factor for success is the already existing social network of the campaigners which might lead to a recreation of social systems. While crowdfunding provides certain opportunities for women entrepreneurs, we challenge the allegedly gender-neutral environment and question the chances of digitalization as non-biased by discrimina-tion. In order to “democratize” the funding process further, the first step, particularly in Ita-ly, must be to target a bigger audience beyond existing networks.