Some curricular elements are threshold concepts that involve "troublesome knowledge," not because they are difficult for students to comprehend per se, but because they are challenging for students to fully appreciate. In this article, we suggest that entrepreneurial failure is a threshold concept in entrepreneurship courses because students may get so fixated on failure's economic costs that they neither fully appreciate the social and emotional costs nor recognize the potential benefits of failure to entrepreneurs. In a multiphase empirical study, we explore the effects of entrepreneurial experiences on how students categorize and conceptualize entrepreneurial failure. We find that students with entrepreneurial experiences provide more complex, multicategorical descriptions of failure and are more likely to represent the useful aspects of failure in their descriptions. Our findings highlight the role of experiences in facilitating students' understanding of the threshold concept of entrepreneurial failure and suggest that entrepreneurship educators can leverage student experiences to promote more complex representations that account for both the costs and benefits of failure.