To explore inconsistent findings in the perceived self‐efficacy and entrepreneurship literatures as they relate to the type of complex, risky decisions (i.e., those that commit financial resources to generate new revenue) made by marketing managers, entrepreneurs, and corporate intrapreneurs, this paper uses a series of four theoretically driven, empirical studies to investigate gender differences in risk‐taking self‐efficacies (i.e., one's perceived abilities to make financially risky, business development decisions). The results indicate the following: (1) no gender differences in risk‐taking self‐efficacies absent a task; (2) after performing a complex, risk‐laden task, the risk‐taking self‐efficacies of subjects receiving negatively valenced outcome information and women were less than those of subjects receiving positively valenced outcome information and men; (3) this effect remains for women when experience in the task domain is high and when diagnostic information about prior outcomes is provided; (4) the reason for the effect appears to be that men and women use information about their prior decision's outcomes differently when assessing their risk‐taking self‐efficacies; and (5) the effect disappears when social cues intended to facilitate accurate performance comparisons are introduced into the task environment. These findings support existing theories, identify areas needing development, and show how these effects can limit participation in both complex, risk‐laden tasks and careers that are thought to involve performing such tasks.