Today’s society is reshaped by the new multicultural settings and cultural diversity which gives a certain specificity to social, economic and political developments. The successful business and social business assumes the ability to analyse and to solve eco- social problems, to think ethically, creatively, to work and cooperate in multicultural teams but with a competitive complement, to manage risk and to handle uncertainty. This paper aims to identify students’, teachers’ and entrepreneurs’ perceptions on values which are relevant to profilemaking of a successful entrepreneur who grows his/her business/social business in a multicultural context. We developed an exploratory study based on cross-sector and cross-country comparative data, using the questionnaire survey method on a sample of 231 subjects from Suceava, Romania and from Chernivtsi Oblast, Ukraine. Our study results confirm that the perception on values relevant to profile-making of a successful entrepreneur presents significant differences in accordance with the socio-professional status, with the cultural context of belonging and with the gender of subjects. The findings could provide an evidence based guiding list of indicators in order to sustain the axiological perspective of the entrepreneurial education in both national and international context of higher education institutions and to select the appropriate ways of building the entrepreneurial competencies through the Education for Entrepreneurship and for Social Entrepreneurship.