The authors test a general model of career mobility and entrepreneurship based on the premise that job transitions between organizations are influenced by the unique role of the organizational founder. Three related ideas inform the authors' inquiry. First, individuals in that role are endowed with the right to act as representatives of their organizations which increases commitment and deters external mobility. Second, the founder role, because of its uniqueness, defines how entrepreneurs think of themselves thus aligning person and position. Repeat entrepreneurship occurs because after a founder leaves, this alignment is disrupted and the need to restore it leads to becoming a founder again. Third, the authors see the founder role as imbued with charismatic authority. This creates an aura of deference and a propensity to emulate the founder that inspires organizational members working alongside the founder to themselves become entrepreneurs. The authors investigate these ideas empirically in the context of the global high-end fashion industry through a research design that allows us to compare leading designers' career histories as both founders and members and their transitions to and out of entrepreneurship.