Entrepreneurs are known for their deep emotional attachment and commitment to their ventures. Experiencing such intense positive emotions can paradoxically lead to obsessive entrepreneurial passion (ObEP), an uncontrollable form of passion negatively associated with well-being. Despite the negative consequences of ObEP, entrepreneurs may still develop an uncontrolled emotional bond with their businesses. While research has focused on the benefits of entrepreneurial passion, there is limited research on how obsessive passion forms and its potential effects on well-being are still a topic of debate as prior studies show mixed and inconclusive findings. As such, our overarching concern is to know why entrepreneurs develop ObEP and how it potentially shapes their entrepreneurial well-being. To examine this research question, we conducted three interrelated studies. In our first study, we examined the potential drivers of obsessive entrepreneurial passion and its impact on subjective and psychological well-being by employing a quantitative research design. We identified affective entrepreneurial commitment and perceived competitive pressure as two potential drivers of obsessive entrepreneurial passion based on the premise that passion can emerge from internal and social pressure. We found that both drivers can fuel obsessive entrepreneurial passion, which negatively mediates the relationship between affective entrepreneurial commitment and subjective and psychological well-being, as well as the relationship between perceived competitive pressure and both types of entrepreneurial well-being. In our second study, we used qualitative methods to examine the underlying psychological process between obsessive entrepreneurial passion and well-being. As obsessively passionate entrepreneurs place heightened importance on their self-worth, they tend to cognitively evaluate themselves and verify their self-worth, paying attention to their own perspectives and those close to them. Thus, such cognitive self-evaluation of entrepreneurs can explain the underlying psychological process between obsessive entrepreneurial passion and well-being outcomes. We introduced a dynamic process model to explain how the cognitive self-evaluation of obsessively passionate entrepreneurs (ObPEs) results in different well-being outcomes due to experienced discrepancies and conflicts. The model portrays four phases: the emergence of ObEP, cognitive evaluation of the self, feelings of self-discrepancies and conflicts, and well-being outcomes. In addition, we explained the detrimental side of obsessive entrepreneurial passion by highlighting the vicious cycle of passion. In our third study, we proposed a dynamic model to explain how obsessively passionate entrepreneurs can manage negative emotions triggered by stress and regulate their obsessive entrepreneurial passion to shape their well-being. Using the lens of cognitive appraisal theory, we explained that obsessively passionate entrepreneurs will appraise stress as challenges or threats depending on their goals, beliefs, and ability to access resources to cope with the negative emotions triggered by stress. We highlighted that entrepreneurs who employ approach strategies to cope with negative emotions can regulate their passion by enhancing their level of obsessive entrepreneurial passion without detriment to their well-being. However, using avoidance strategies will cause them to reduce their attachment to business, leading to reduced well-being.