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"Hustling" or sex work is a common means of surviving on the streets and paying for drugs among homeless youth. In this article, we formulate the concepts of "street capital" and "street competencies" to describe how 10 young men who have sex with men (YMSM) in New York City accumulated various knowledge and skills throughout their childhood and adolescence, and later entered into homelessness and the street economy as sex workers. While half of these young men described themselves as gay or bisexual, sexual identity was not a primary consideration amongst these youth. All were homeless and/or users of illegal drugs, and all survived through intimate involvement in the "street economy"—an informal system of exchange that circulates drugs, sex, and money across a range of settings and participants. Based upon an analysis of life history accounts gained through ethnographic interviews, we describe common pathways into the street economy with an emphasis on understanding how these 10 young men of diverse backgrounds became involved in homelessness, drugs, and sex work. In doing this, we document the differential sources of knowledge and particular childhood experiences that launched these youth into coherent street careers.