This research looks at the role that an entrepreneur’s gender and prior experience (failure vs. success) play in crowdfunding investment decisions. Crowdfunding has recently emerged as a female-friendly platform used by entrepreneurs in order to secure finances, yet empirical evidence suggests that females are still not funded to the same extent as male entrepreneurs. We hypothesize that investment decisions will be influenced by the entrepreneur’s gender and we explore this effect under the circumstance that the entrepreneur holds some form of prior experience (success/failure). The role of the entrepreneur’s gender is examined in the context of determining whether the entrepreneur’s prior experience (failure in particular) is viewed positively or negatively by the investor. Adopting an experimental methodology, we test a number of hypothesized relationships between prior success/failure, gender, and funding. In short, the proposed research model suggests that prior entrepreneurial experience has an impact on the investment decision, and this relationship is moderated by the entrepreneur’s gender.