Homeless youth (HY) who lack employment in the formal economy typically turn to the street economy (e.g., prostitution, drug selling) for survival. Guided by the theory of social control, the present paper explores factors influencing HY's initiation into the street economy. Eighty HY (ages 15-23) were recruited from four community-based organizations. All participated in structured interviews and 25% participated in qualitative interviews. Almost all HY had participated in the street (81%) and formal economies (69%). Five main factors simultaneously influenced initiation into the street economy: social control/bonds, barriers to the formal economy (e.g., homelessness, educational deficits, mental health problems, incarceration, stigma), tangible and social/emotional benefits of the street economy, severe economic need, and the active recruitment of HY into the street economy by others. Qualitative and quantitative data sources were congruent. Intervention efforts are needed at multiple levels of influence to promote HY's success in the formal economy.