Several theoretical traditions offered insights into individual success in conventional activities. This analysis extends these previous discussions by suggesting that explanations of success also apply to crime. The discussion notes that research on conventional success focused on the effects of human and social capital; criminal forms of human and social capital are important for illegal success. In addition, various aspects of conventional personal capital also have important roles in both legal and illegal prosperity. These aspects included a heightened desire for wealth, a propensity for risk-taking, a willingness to cooperate, and competence. The present research involved a panel study of 482 street or homeless youth ages 24 or under in Toronto, Ontario, and Vancouver, British Columbia. Participants provided information about their legal and illegal activities, the amount of money earned in each area, and demographics. Results revealed that 58 percent of the youths had sold drugs at least once since leaving home. Results revealed that one component of human capital, specialization, and two personal capital attributes, a willingness to collaborate and a desire for wealth, have sizable effects on success in illegal enterprises. A third contributor to legal prosperity, competence, intensified and gave direction to two of these effects. The analysis concluded that the findings offered some support for the hypothesis that theories of legal prosperity also explained illegal success and affirmed the usefulness of economic theories for studying crime. Tables, figures, notes, and 72 references (Author abstract modified)