In the context of the social and economic changes in Russia during the transformation period, a historical conflict emerges between the value ethos of the Russian intelligentsia and the practical rationality of entrepreneurs: the new economic habitus of the latter stands in contrast to an anti-capitalist tendency that has been inherent in Russian literature for centuries. The book examines both literary and media discourses of entrepreneurs. It shows that while there is still a strong bipolarity between the writing intelligentsia and the entrepreneurs, this is now overlapped and modified by new discursive trends and meanings that offer a certain recognition to the entrepreneurs.