Entrepreneurial well-being is integral to entrepreneurs' lives, enabling them to effectively overcome challenges while achieving business success. Passionate engagement in entrepreneurial activities enhances well-being by generating positive outcomes. However, entrepreneurial passion also leads to poor well-being outcomes, referred to as obsessive entrepreneurial passion. Obsessively passionate entrepreneurs enjoy the attachment to their business but experience greater stress and negative emotions due to its rigid and controlling nature. Thus, it is critical for entrepreneurs to regulate their passion while coping with stress and associated negative emotions to pursue desired outcomes. To address this issue, we propose a dynamic model to explain how obsessively passionate entrepreneurs can manage negative emotions triggered by stress and to regulate their obsessive entrepreneurial passion to shape their well-being. Using the lens of cognitive appraisal theory, we explain 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 highlight entrepreneurs who employ approach strategies to cope with negative emotions can regulate their passion by enhancing the level of obsessive entrepreneurial passion without detriment to their well-being. However, using avoidance strategies will cause them to reduce their attachment towards business, leading to lower well-being.