The paper compares entrepreneurship in similar cultural settings with a different path of development for 40 years. The analysis confirms a still lower level of entrepreneurship in East Germany in the year 2000, although patterns of entrepreneurship in both regions are broadly comparable. Entrepreneurs are predominately male, and they mainly operate in trade and services. But the analysis also shows distinctive characteristics of East German entrepreneurship, e.g., a higher participation of female entrepreneurs. Overall, the findings draw attention to the institutional embeddedness of entrepreneurship, which is influenced by the regulatory frame, societal values and norms of behaviour, which contributes to differences in the nature and extent of entrepreneurship.