The initial school to work transition is a critical time for individuals in achieving the economic benefits of post-secondary education. Community colleges perform a key role in this connection to the workplace for disadvantaged groups. This research examined the effectiveness of a large comprehensive community college in achieving successful transition to the workplace for equity and female graduates. Data were derived from a recent graduate survey and from institutional data on demographic and achievement characteristics. Various statistical techniques were used to analyze the initial workplace conditions for disadvantaged groups and the influence of explanatory variables on employment and earnings. Findings indicate that women earn less than men and that equity graduates have higher initial unemployment rates. Results suggest human capital theory may not be able to explain these differential occupational outcomes and the lower returns for equivalent educational investments.