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After his musical career peaked, he taught and was vice-principal at the Maryknoll School, a parochial school in Honolulu, Hawaii, and as a Professor at Chaminade University, a private Marianist University which shares grounds with Saint Louis School. On July 1, 2015, Medeiros became the Head of School/Principal of Saint Louis School in Honolulu and in 2017 its President/CEO.

On July 1, 2015, Medeiros was appointed Head of School/Principal of St. Louis School, an all boys Catholic (Marianist Order) school (K-12) in Honolulu Oahu, where he is now its President/CEO since 2017.

In 2014, Medeiros received a doctorate degree in Educational Leadership from the University of Southern California.

He attended Leeward Community College and transferred to University of Hawaii–West Oahu, where he received his bachelor's degree. He graduated from The University of Phoenix-Hawaii with an MA in Elementary Education.

Medeiros is of Portuguese ancestry. He and his wife, Tammy, have been married since 1996. They have a son, Chord, and a daughter, Lyric.

In 1988, he recorded the single "Un roman d'amitié (Friend You Give Me a Reason)", a duet in French with Elsa Lunghini that reached #1 in France for three weeks. He also achieved a 1990 United States #1 hit duet with Bobby Brown titled "She Ain't Worth It". The same track peaked at #12 in the UK Singles Chart. He had another hit duet with Ray Parker, Jr. titled "All I'm Missing Is You" which peaked at #32 in the US. In 1989, Medeiros recorded "Under Any Moon" with The Jets, which was included on the soundtrack of The Karate Kid Part III in which he made an appearance in the movie singing. In 1992 Medeiros recorded a duet with Thomas Anders (of Modern Talking fame) titled "Standing Alone" and shot a video.

In 1986, at the age of 16, Medeiros won Brown Bags to Stardom, a local radio talent contest in Hawaii, when he performed a cover version of George Benson's "Nothing's Gonna Change My Love for You" which was subsequently produced into an album by a small local independent label. A visiting radio executive, Guy Zapoleon, from KZZP in Phoenix, Arizona heard the song and took the record back to Phoenix, where, through word of mouth, it became a national hit. Later, a worldwide hit, it reached #12 on the Billboard Hot 100 and spent four weeks at number one on the UK Singles Chart in July 1988. It reached #3 on Billboard's Adult Contemporary chart.

Glenn Alan Medeiros (born June 24, 1970) is an American educator and a former singer and songwriter of Portuguese descent who achieved chart success in the late 1980s and early 1990s. He is best known on the national and international music scene for his 1987 global smash, "Nothing's Gonna Change My Love for You", and "She Ain't Worth It", a US chart-topper in 1990. He has remained regularly involved in the music industry in his home state of Hawaii (including several headliner and related musical variety shows in Waikiki) long after achieving global success decades ago.