Despite an increased interest in the phenomenon of stigma in organizations, we know very little about the interactions between those who are stigmatized and those who stigmatize them. To overcome this critical shortcoming, we examine the role of stereotypes held by both boundary spanners and customers of stigmatized organizations. To do so, we gathered data regarding boundary spanners (vendors) of homeless-advocate newspapers from three different sources (boundary spanners, customers, and trained observers) and conducted multilevel path-analytic hypothesis tests, empirically linking key factors involved in stigmatized business exchanges.