This paper explores the relationship among socio-political culture and the economic environment. It places the entrepreneur at the forefront of the Transitional Economy and identifies the entrepreneur as a catalyst for change and progress. Within wider world changes, this discussion and interrogation of entrepreneurial development in the Transitional Economy provides new knowledge from the perspective of both the authors and the perceptions of 638 respondents who contributed to the research. The concluding model makes explicit that the constructs Freedom and History serve as moderators for entrepreneurial development in the Transitional Economy and suggests that the strength of an individual is created by societal construct. The progress of entrepreneurs is enhanced where there is political and economic freedom to operate, informed by historical knowledge.