Hollendoner is Director of the Broadway Youth Center for Howard Brown Health Center and a youth activist. He oversees the daily operation of Chicago’s most comprehensive center for at-risk youth; programs include: drop-in services, case management, therapy, medical care, HIV testing and prevention services, mentor programming, GED classes, support & social groups, basic need services, and youth development programming.

Hollendoner's activist started in his teens as a South Suburban youth activist. From 1997-2001 he was involved with Aunt Martha’s Youth Service Center including as HIV Prevention Program Coordinator. From 1997-2003 with the Gay, Lesbian and Straight Education Network of Chicago ( GLSEN ) , he was a Program Coordinator, Strategic Planning Chair, Youth Committee Chair, and a Scholarship Recipient.

His other activities include About Face Youth Theatre ( he received the Michael Leppen Community Leader Award in 2005 ) ; Chicago Metropolitan Sports Association softball; the Chicago HIV Prevention Planning Group; and the Illinois Safe Schools Alliance.