In this paper, we explore the effect that failure experiences have on entrepreneurs' well-being, and also observe the changes of such effect in different entrepreneurial environment. By doing hierarchy regression, we found that entrepreneurs' prior failure times have a negative relationship to entrepreneurs' well-being, and such relationship is strengthened when entrepreneurs are embedded in a entrepreneurial friendly environment. Our marginal effect analysis also confirms our hypothesis that entrepreneurs' overall well-being, as well as their job satisfaction, life satisfaction and psychology well-being, decreases with failure times increasing.