Entrepreneurship scholars have focused primarily on the rewards of entrepreneuring behaviors. As an alternative to this perspective, we examine serial entrepreneurship through the lens of psychological addiction, and demonstrate how such a frame can yield important insights into behaviors that represent a possible ‘dark side’ of entrepreneurial action. We represent these insights to include: 1) a more comprehensive understanding of a possible ‘dark side’ of entrepreneuring - we offer the notion of addiction, and investigate the possible negative implications of addictive behaviors given an entrepreneurial environment; 2) an explicit examination of the specific qualities and attributes of the entrepreneurial experience which may contribute to addictive behaviors - what physiological, cognitive, and emotional returns to the individual resulting from entrepreneurial action may lead to the manifestation of a compulsion to create and grow new ventures; and 3) we suggest that addiction, as a theoretical lens, necessitates theory-building focused both on how the entrepreneur influences the venture, but importantly on how the venture influences the entrepreneur. This reciprocal relationship is understudied in the entrepreneurship literature.