This empirical study consists of two parts. The first part of the study examines the cultural characteristics and dimensions of entrepreneurs and factory workers in transition economies during the early transition period to determine if their cultural values were similar to those found in other nations. The second part of the study compares the differences in Hofstede’s cultural dimension scores between entrepreneurs and workers in market economies. It might seem extraordinary that after more than 70 years of a centralized nonentrepreneurial society that all of the communist nations that the current authors studied had essentially the same cultural differences among entrepreneurs that were found in capitalist nations with a long history of entrepreneurial activity.