Cognitive elements are some of the most influential features characterizing the “entrepreneurial mind,” yet dominant explanatory frameworks have struggled to clarify how and why entrepreneurs’ behaviors vary so widely from others. Even individuals who come from similar conditions and share the same environment as entrepreneurs differ greatly in their perceptions and behaviors compared to their entrepreneur counterparts. Drawing on and contributing to the theoretical work in social cognitive theory, this research aims to improve the understanding of entrepreneurs’ cognitive processes by exploring Global Entrepreneurship Monitor data, which is the most comprehensive comparative database for entrepreneurship. The first essay analyzes how different experts in entrepreneurship perceive their surrounding environment and opportunities. More specifically, this study discusses how experts who are entrepreneurs perceive their entrepreneurial ecosystem and opportunities differently than non-entrepreneur experts. It is suggested that people act the way they do not only because of different interpretations of the environment but also because of the relative importance they give to context and themselves in their mental frameworks. The second essay analyzes the relationship between optimism about the emergence of future entrepreneurial opportunities and the length of entrepreneurial experience and the ways internal and external motivations can condition this relationship. Results suggest that although entrepreneurs are more optimistic about future business opportunities that non-entrepreneurs, experienced entrepreneurs tend to be less optimistic than novice and potential entrepreneurs. Finally, based on evidence suggesting that entrepreneurs are likely to consider that fostering an innovative orientation is the best approach to increasing firm performance independent of the circumstances, the third study proposes a moderated mediation model of the effect of subjective valuations of innovation on entrepreneurs’ strategic orientation and growth expectations. Entrepreneurs involved in innovative entrepreneurship are more likely to have higher growth expectation, with subjective valuations playing a direct and indirect role in their expectations.