The paper looks at the important issues of entrepreneurship and the emergence of entrepreneurs in the Republic of South Africa, in the context of education and social policy. The authors argue that this necessary emergence through, the processes of transformation is too slow and is at the cross roads, after nearly 23 years of democracy, post 1994. In similar vein, the paper in its introduction indicates that higher education funds must be targeted. The paper does not delve into the history and definitions of entrepreneurship and of entrepreneurs. It further argues that, the next president’s priority needs to be job creation in terms of sustained social policy imperatives. This has failed miserably under the current President Jacob Zuma and the democratic government of the country. It also discusses the concept of incubators which can create thousands of jobs for the beleaguered South African Economy. It situates the subject matter from the perspective that the Chief Justice of South Africa criticizes businesses and, states that transformation is too slow. On the other hand the paper argues that the bargaining councils and trade union movement in South Africa fail small businesses and, the narrative explores very briefly the issue of rigid business practices that do not inspire workers. It further argues that, the technical college system is broken and stymies the important emergence of entrepreneurship. In articulating the discussion in this paper, the authors cogently argue that, the trade unions of South Africa, has cozied up to government and, in so doing have trampled upon the rights of workers. Tied to these aspects is the reality that South Africa’s startups fail to gain traction. Amidst other issues the authors further argue that, universities must meet labour needs and play an important role in developing the modalities for entrepreneurship in terms of producing entrepreneurs.  It finally argues that entrepreneurial success goes beyond political sentiment and asks the vexing question as to why our neighbours Botswana can create so many new entrepreneurs.   Key Words: Jobs, Universities, Labour, Entrepreneurship, Entrepreneurs, Startups, Political, Technical Education, Practices, Inspire, Transformation, Incubators, Job Creation