This study compares and contrasts perceptions of entrepreneurship success factors in Estonia and the USA. The 115-item E-World survey is used to highlight differences of implicit beliefs about behaviors and characteristics of successful entrepreneurs between the USA, a country with a long history of entrepreneurial development, and Estonia, a small economy where entrepreneurship has played an important role in the transition from a command to a market economy. Cultural differences and the institutional context emerge as key models in interpreting the social obligations of entrepreneurs, thus linking future orientation and communication, and entrepreneurs' perceptions of entrepreneurial risks and challenges.