<p>This study investigates the determinants of entrepreneurs’ satisfaction, focusing on entrepreneurs from family businesses and considering the influence of gender and parental responsibilities. It draws upon work-family theories to explore the complex dynamics of role enrichment and conflict within the entrepreneurial context. The study involved data from 379 business owners or co-owners from 2020 to 2022. The study employed quantile regression to address the non-normal errors, heteroscedasticity, and outliers in the data, making no assumptions about the parametric distribution of errors. The findings highlight the significant impact of family entrepreneurs’ ownership on family businesses’ satisfaction, leading to role conflicts that negatively affect satisfaction. Specifically, entrepreneurs from family businesses face higher levels of stress due to overlapping business and familial obligations, leading to heightened role strain and reduced well-being. Conversely, improved business performance positively influences entrepreneurs’ satisfaction, enhancing their confidence and self-image. Gender alone does not substantially influence satisfaction, but when combined with parental responsibilities, women entrepreneurs can experience episodes of role conflict that hinder satisfaction. Moreover, the intersection of gender, having children, and family ownership substantially affects entrepreneurs’ satisfaction, particularly family business entrepreneurs. This suggests that the cumulative burden of gender expectations, parental responsibilities, and business ownership amplifies the challenges faced by women entrepreneurs. This study highlights the complex factors affecting entrepreneurs’ satisfaction, including family business entrepreneurs, business performance, and gender-specific challenges. It advances our understanding of work-family dynamics and their impact on entrepreneurial well-being. These findings hold significance for family business entrepreneurs, policymakers, and entrepreneur support systems.</p>