With the increasingly egalitarian division of childcare responsibilities in couples, we are seeing more and more male entrepreneurs who wish to be involved fathers yet face difficulties in jointly managing high demands in both their business and family domains when transitioning into parenthood. Intriguingly, this trend has given rise to a new phenomenon of overwhelmed “dadpreneurs” who seemingly struggle with transitioning into parenthood even more than female entrepreneurs, despite still assuming less childcare responsibilities than their female counterparts. We abductively probe potential explanations for this anomaly using longitudinal Swedish register data covering the period of 2008 to 2020. Applying a quasi-experimental event study setup with stacked difference-in-difference analyses, our findings suggest that the transition into parenthood has more negative effects on male than female entrepreneurs’ new venture performance once they assume comparable childcare responsibilities. Findings from abductive analyses are thereby consistent with the notion that female entrepreneurs are more effective and skilled in juggling work and family responsibilities, and that these superior juggling skills are acquired through gender socialization. To succeed in entrepreneurship, entrepreneurs may thus no longer only need to be Jacks/Jills-of-all-trades within the business, but across all domains of their life.