In this study, we use affective computing technologies to evaluate the emotions entrepreneurs display and convey to others. Rather than assume that the emotional experience of entrepreneurship is consistent across individuals, we examine variation between entrepreneurs in such expression. Further, we uncover substantial variation in emotional expression within individuals as they reflect on different specific aspects of their venture and entrepreneurial experience. Using 37 videos of entrepreneurs telling their oral histories, sampled every 200 milliseconds, we uncover key differences between and within entrepreneurs across their stories. Further, we identify important affective triggers such as failure, motivation to start their venture, significant accomplishments, and future plans and goals.