Drawing from neo-institutional theory, we examine the relationship between preference for entrepreneurship and actual entrepreneurship behavior across multiple countries and cultures. We elucidate how multiple societal-level cultural models, namely Hofstede, Global Leadership and Organizational Behavior Effectiveness (GLOBE), and Schwartz affect the individual-level process connecting expressed preference for self-employment and actual behavior. Our hypotheses were tested using a multilevel technique on a sample of 20,755 individuals across 24 countries. The findings indicate that the moderating effect of predominant cultural cognition is partially supported. Contributions and implications for theory and practice are also discussed.