This paper argues that spoiled identity, which results from stigmatization, is an important spur to engaging in entrepreneurial activity. The idea that some people become entrepreneurs in response to fragmentation or damage done to the self is not new. To date, however, this idea been addressed from the standpoint of depth psychology. This paper uses Goffman’s spoiled identity concept to shift the focus from psychological dysfunction to social and contextual dimensions of self-identity, understood sociologically. These issues are explored through the abbreviated life histories of two people, who regard themselves as Australian Aboriginal entrepreneurs. Each person dealt with the effects of stigmatization by using aspects of Aboriginal culture both to position and present themselves as entrepreneurs.