Purpose We designed and evaluated for feasibility an intervention - Yo Puedo - that addresses social network influences and socioeconomic opportunities in a neighborhood with substantial gang exposure and early childbearing. Methods Yo Puedo combined conditional cash transfers for completion of educational and reproductive health wellness goals with life skills sessions, and targeted youth 16-21 years of age and same-aged members of their social network. We conducted a two-arm study with social networks randomized to the intervention or a standard services control arm. We evaluated intervention uptake, adherence, and safety; and assessed evidence of effects on behavioral outcomes associated with unintended pregnancy and sexually transmitted infection risk. Results A total of 72 social networks composed of 162 youth enrolled, with 92% retention over 6 months. Seventy-two percent of youth randomized to the intervention participated in intervention activities: 53% received at least one conditional cash transfer payment and 66% came to at least one life skills session. We found no evidence that cash payments financed illicit or high-risk behavior. At 6 months, compared with controls, intervention participants had a lower odds of hanging out on the street frequently (odds ratio [OR],.54; p =.10) and a lower odds of reporting that their close friends had been incarcerated (OR,.6; p =.12). They reported less regular alcohol use (OR,.54; p =.04) and a lower odds of having sex (OR,.50; p =.04). Conclusions The feasibility evaluation of Yo Puedo demonstrated its promise; a larger evaluation of effects on pregnancy and sustained behavioral changes is warranted. © 2014 Society for Adolescent Health and Medicine. All rights reserved.