More than two million youth in the United States are homeless at some time each year (Whitbeck, 2009). They often have histories of depression, complex trauma, substance abuse, and physical and sexual abuse—all of which make obtaining and maintaining competitive employment difficult. Epidemiologic data indicate that 26% meet the clinical criteria for major depression, 35% have attempted suicide, and 72% use illegal substances to cope (Rotheram-Borus & Milburn, 2004). Their connection to school is also irregular or non-existent, which contributes to low educational levels and limited employment skills. Several studies suggest that over one-third of youth who are homeless have dropped out of school, do not attend school regularly, or fail to earn a high-school diploma by age 18 (Thompson, Pollio, & Constantine, 2002; Whitbeck, 2009). These mental health and behavioural health challenges, combined with low educational and employment skills, contribute to high unemployment rates among youth who are homeless compared with their housed peers. Housed youth in the general population (aged 16–24) have unemployment rates ranging between 8% and 17% (U.S. Department of Labor, Bureau of Labor Statistics, 2016), whereas unemployment rates for youth who are homeless range from 39% to 71% across various samples of youth living on the street or in shelters (Courtney, Piliavin, Grogan-Kaylor, & Nesmith, 2001; Ferguson & Xie, 2008; Lenz- Rashid, 2006; Whitbeck, 2009).