The need for sleep has important implications for entrepreneurship. Researchers have come to understand that sleep insufficiency affects creativity, innovation, self-control and operational efficacy. Yet quality sleep often eludes an entrepreneur because of the demands from the business environment, fear of failure and job insecurity, among other things. Hence, a sleep paradox exists where aberrant sleep patterns or sleeplessness undermine success. However, aberrant sleep patterns and sleeplessness are a necessary part of successful entrepreneurial experiences. The current research used a qualitative design to understand how successful entrepreneurs retrospectively perceive aberrant sleep patterns or sleep restriction (i.e., sleeplessness); but, more importantly, how they implement coping mechanisms to overcome this paradox to achieve positive outcomes for their business. Successful entrepreneurs of the current research were seen to self-regulate their actions to address the vagaries of entrepreneurial experience. They manage aberrant sleep patterns or sleeplessness by taking steps to develop adaptative tools (i.e., coping mechanisms such as mental, physical and behavioural shortcuts) to aid decision-making in an uncertain business environment and to facilitate the sustainability of their entrepreneurial endeavours.