This paper aims to study the issues and unique characteristics surrounding the birth and development of the private sector in People’s Republic of China (P.R. China); to analyze the interaction of entrepreneurial behavior and the country’s unique and continuously changing regulatory and institutional environment; to examine the actions, outcomes, and composition of this emerging entrepreneurial class; and to analyze the implications for entrepreneurship research in transitional economies. The paper offers a model built on a dynamic and transitional cycle. Using this model, the paper examines how uncertainties, ambiguities, and changing regulatory environments may create opportunities, bolstering the entrepreneurial class as well as an impressive private sector in a country where entrepreneurs and private business can be at odds with socialist ideology and culture in addition to many regulatory and institutional obstacles. Rather than relying upon limited survey data targeted at specific locations, industries, or time periods, this study is based on seven large-scale surveys conducted from 1993 to 2006 in both urban and rural areas extending horizontally across different industries in P. R. China, with a primary focus on private business. The findings are relevant for future research and government policy in transitional economies.