<p>We investigate the impact of entrepreneur’s insomnia on psychological capital and the moderating role of gender in two countries. In a cross-sectional study, we found the expected negative relationship between insomnia and psychological capital suggesting a psychological cost. Conversely, our diary study revealed a counterintuitive positive relationship. We resolve this paradox by showing that this positive result is driven by active and short-term psychological management required in a high-performance hustle culture. Advanced dynamic modeling reveals insomnia stickiness and behavioral compensation and shows that an entrepreneur learns to maintain psychological capital despite insomnia. We also find that, in high insomnia conditions, a woman entrepreneur has lower psychological capital. This work highlights the important role of context and adaptive behavior in shaping entrepreneur’s insomnia.</p>