This research sought to examine the lived experiences and minds of entrepreneurs who had influenced society in ways beyond the domain of the private sector. An entrepreneur was defined as an individual who pursues opportunity or is driven by the perception of opportunity. It was proffered that a divide exists in our understanding of an entrepreneur—as person—and an entrepreneur—as business starter. To a great extent, this divide has limited exploration of the connections and benefits that entrepreneurial thinking might bring to education. This was a qualitative and interpretivist study based on interviews with a purposive sample of entrepreneurs who have had a major influence in private, public, and more generally in the plural sectors in and around Canada. Nine entrepreneurs were invited to tell their life stories, to provide their perceptions of how entrepreneurs think and to relate how they believed they had developed their skills. Using in-depth interviews, the researcher was able to discover, in part, the essence of how these entrepreneurs thought, how they made decisions, and how they viewed themselves and their world. The findings and insights add to the growing body of literature on entrepreneurship. The researcher argued that the dissertation had given light to the lived experience of entrepreneurs. Understanding how these persons had become entrepreneurial and how they had recognized opportunities for their own mentorship were addressed by the research. How these entrepreneurs thought, their motivations, and interests, as well as how they perceived their role in the world provided valuable insights, especially as one seeks to understand how to cultivate or develop, nurture and encourage entrepreneurs, and to foster entrepreneurial behaviour throughout the education sector. The exploratory insights from these rich interviews serve to further foster fruitful conversations on potential alignments between the ways and thinking of entrepreneurs and educational systems.