Objective: To reduce mental health symptoms and high-risk behaviors and increase social support and service utilization among street-living youth, the authors conducted a pilot study to assess the feasibility of the social enterprise intervention (SEI) at a homeless youth agency. Method: Convenience sampling was used to recruit 16 street-living youth from the agency. SEI participants received 7 months of vocational and small business training and service referrals. A comparison sample of 12 agency youth was used. Results: Findings from independent sample t tests demonstrate that SEI participants displayed significant improvements at 9 months in life satisfaction, family contact, peer support, and depressive symptoms. Conclusions: Preliminary findings suggest that the SEI was feasible within the agency setting and associated with higher mental health and social outcomes. (Contains 3 figures and 3 tables.)