This paper explores the influence of an entrepreneur’s family on the entrepreneur’s well-being, their business experience and vice versa. Set in a relatively under-research context of business exit, the study has analysed the entrepreneurial journey of 46 cases of business exits using gender as a bio-cultural construct. Empirical findings reveal the underlying causal mechanisms that mediate the work-family interface of an entrepreneur’s life and consequently their business exit decision. Gendering is not confined to social dyn­­­­amics but shapes the coping and post-exit recovery mechanisms as well.