Numerous studies concern the activities of entrepreneurs and the economic, social, and political impact they have had on societies throughout history. While many scholars have devoted much attention to the quantitative elements associated with entrepreneurial activity, few have focused on the underlying qualitative factors leading to the success or failure of entrepreneurial activities. This research focused on the developing and transitional economic conditions in post-communist Russia. Among the concepts examined were the relationships of the entrepreneurs to political, economic, social, ethical, and cultural influences that influenced the rise of entrepreneurship within formerly Russian-speaking sectors of the region. The study revealed numerous trends and patterns that emphasized strong cultural beliefs, national pride, and a notable difference in the rate of change between Kiev and St. Petersburg since the fall of communism. However, the spirit of entrepreneurship is strong, as the number of new business entities continues to grow and as leadership traits begin to develop within the newly formed free-market system.