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We aim at analyzing female participation in Italian academic spin-offs using publically available data and a unique hand-collected database of all academic spin-offs set up in Italy from 2002 to 2007. We base our study on three complementary levels of analysis: macro, meso, and micro level. We show that the gender gap in academic spin-offs is relevant and that a certain degree of spatial heterogeneity—possibly reflecting cultural and environmental differences between Italian provinces—exists. Furthermore, our findings show a disadvantage of females in the startup funding phase: an unfavorable circumstance that reduces their chances of success and force them to create new businesses mainly in the service sector. Social relationships and empathy among females may help compensate their disadvantages and break down barriers to entrepreneurship.