This study focuses on how life satisfaction mediates the links from dispositional optimism to entrepreneurial success and exit intentions. The theoretical basis of this study is a hierarchical approach to personality, and its primary contribution is to the research on psychological entrepreneurship. To analyze potential links among these constructs we develop five hypotheses and then test them on small and medium-sized entrepreneurs. Hypotheses are tested by using consistent bootstrapped PLS-SEM estimations. Our results indicate that dispositional optimism is associated with entrepreneurial success. Our study also reveals that life satisfaction mediates the relationship between dispositional optimism and entrepreneurial success in addition to the relationship between dispositional optimism and exit intentions. Our study demonstrates that entrepreneurial success is related to exit intentions. We conclude by discussing the implications for researchers and practitioners.