Over the past few years, there has been a surge of interest in entrepreneur mental health and well-being. Research has shown 72% of entrepreneurs self-report a lifetime history of mental health concerns (depression, substance abuse, attention-deficit/hyperactivity disorder, and bipolar), and countless others incur varying degrees of emotional, physical, and spiritual distress. While many have been quick to declare a mental health “crisis” or “epidemic” among entrepreneurs, the reality may not be so simple. Entrepreneurs with mental health challenges may in fact have a competitive advantage—they may self-select into entrepreneurial work as a result of the adaptive qualities conferred onto them by their diagnosis. This article explores the myriad reasons for these high rates (from self-selection to diathesis–stress), including the hypermasculinized nature of entrepreneurial culture, the high-stress nature of entrepreneurial work, and the hidden superpowers embedded in the genetics of entrepreneurs. To conclude, the ways in which the entire ecosystem can become healthier through self-understanding and self-care are discussed.