Objectives: The purpose of this research is to broaden views on connection between culture, individual cultural values and individual peculiarities (Hardiness) of entrepreneurs, who have chosen entrepreneurship as a strategy of achievement of their life goals. Methods: We have performed cross-cultural research of entrepreneurs (N=163), representatives of medium- and small-sized business, in several countries: Russia, Italy, Central Asia (Tajikistan, Kazakhstan, Kyrgyzstan). Individual values (S. Schwartz) and Hardiness (S. Maddi) have been measured. Findings: In both developing countries with transition economy (Russia and Central Asia) and in countries with higher level of economic development (Italy) the factor of involvement into entrepreneurial activity is a ratio of individual values (Self-enhancement and Openness to change) and level of Hardiness. According to the discriminant analysis, such values as Self-Direction, Hedonism and Power have a key role in differentiation of entrepreneurs of European countries (Russia and Italy) and countries of Central Asia. Discriminant analysis shows that entrepreneurs of Italy and Russia belong to opposite poles: harmony versus power. The entrepreneurs of Central Asia take intermediate position. The Italian entrepreneurs are closer to the pole, which combines social commitment to harmony (Universalism) with individualistic Self-Direction and Hedonism, and entrepreneurs from Russia are closer to the strictly individualistic pole, which combines Self-Direction and Hedonism with tendency for Power. Novelty/Improvements: The obtained data demonstrate that selection of entrepreneurship as a behavioral strategy for achievement of life goals depends on combination of characteristics of cultural context, as cultural resource, and Hardiness, as personality resource.