The comparison between the operations of the two nonprofit organisations [NPOs] demonstrated the importance of social entrepreneurship [SE] strategies for NPOs’ operational sustainability, with one showing the transitional path. From its inception, Nature Seekers operated like a social enterprise, entrepreneurial and business-like, with earned income financial strategies, resulting in its operational sustainability. Upon start-up, Chosen Vessels was a traditional NPO managed by an entrepreneurial leader with a passion for social change but no business knowledge or experience, resulting in inefficient operational processes and financial problems. Business management training resulted in recognising its operational deficiencies and the application of the SE business management strategy, resulting in improved operational performance. The critical observation is the value of business management training for NPOs. This formal or informal training enables business-like behaviour, leading to NPOs’ operational sustainability in addressing their social mission, suggesting that the relationship between NPOs’ SE strategies and their levels of sustainability is via entrepreneurial leadership with training and experience in business management. Further research would clarify and ratify this new knowledge in the field of social entrepreneurship.