1. In 1986, at the age of 16, Glenn Medeiros won Brown Bags to Stardom, a local radio talent contest at KIKI radio in his hometown of Honolulu, when he performed a cover version of George Benson's "Nothing's Gonna Change My Love for You" which was produced into an album by a small local independent label.
In 1989, Glenn Medeiros recorded "Under Any Moon" with The Jets, which was included on the soundtrack of The Karate Kid Part III in which he made a cameo appearance.
In 1991, Glenn Medeiros produced "If Looks Could Kill " for the comedy film If Looks Could Kill starring Richard Grieco.
In 1992, Glenn Medeiros recorded a duet with Thomas Anders titled "Standing Alone".
Glenn Medeiros graduated from the University of Phoenix with a master's degree in elementary education in 2003.
In 2014, Glenn Medeiros received a doctorate degree in educational leadership from the University of Southern California.
Glenn Medeiros was the vice principal of Maryknoll Grade School and then its high school.
Glenn Medeiros taught at various schools throughout Oahu, including Mililani Middle School, St Joseph School in Waipahu, and Island Pacific Academy in Kapolei.
On July 1,2015, Glenn Medeiros was appointed Principal of St Louis School, an all-boys Catholic school in Honolulu, where he has been its CEO since 2017.
In 2022, Honolulu Civil Beat published an article questioning Glenn Medeiros' leadership, including mismanagement and retaliation against staff.
However, two members of the school's board of trustees denied that Glenn Medeiros ran a toxic workplace.