Persons experiencing homelessness and chronic homelessness often cycle through public systems such as hospitals, behavioral health facilities, justice and law enforcement systems, in addition to accessing outreach and shelter services. This case study examines the Denver Social Impact Bond Initiative launched in 2016, a form of performance based contracting used for supportive services necessary for supportive housing for frequent users. This brief will outline how this form on investing works to create innovative housing and service solutions for frequent users of emergency systems and how potential partners can learn more for application in their own communities.