From an early age it seemed that Weldon took a keen interest in music. His natural musical abilities were quite evident even while in elementary school where he certainly stood out amongst his classmates. In 1973, his mother took him to audition for the Honolulu Boy Choir where his singing talents were quickly recognized by director Roy Hallman. As a member of the choir, Weldon participated in performances through out Hawai‘i and extensively toured the continental US, Mexico and Canada.
The Kekauoha house hold was always filled with music. Weldon grew up listening to old recordings from the 1950s & 60s of his uncle ʻLittle-Joe’ Kekauoha and his renditions of ʻNo Huhu’ and “The Cockeyed Mayor of Kaunakakai”. During the late 1970ʻs Weldon often looked forward to accompanying his grandmother to some of Honoluluʻs favorite watering holes like ʻHankʻs Place’ in Ka‘imuki, ʻWatertown’ near the `Ilikai, and the old ʻRanch House’ in ‘Ainahaina. Together they sought performances by Darrell Lupenui, The Makaha Sonʻs of Ni‘ihau, Kekua Fernandez, Genoa Keawe and especially his uncle Kawai Cockett. Despite the fact that many of these performers have since passed, they certainly left an indelible mark on the shaping of Weldonʻs musical career.