At the age of 16, Gwaai was mentored by Bill Reid. At 18, he worked on his first totem pole project under his father, Guujaaw. This 40-foot totem now stands in Indonesia. Since then they have completed more then 3 more poles together, and he has also worked on a few totem pole projects with his brother, Jaalen. In 2001, Gwaai assisted Michael Nicoll Yahgulanaas with his graphic novel 'A Tale of Two Shamans'. This collaboration has encouraged his interest in experimenting with Haida themes. Gwaai has since gone on to complete the Jewellery Art and Design program at the Vancouver Community Collage where he learned about the process of casting. As well, he is one of the founding members of the Q'altsi'da Kaa players, who are developing their first play to be performed entirely in the Haida language. Gwaai launched his unique line of jewellery, Regalia, in 2009, which features cropped bentwood box designs from the Raven creation story. In 2012, he added additional designs to his Regalia line featuring Naxiin (Chilkat) imagery in this signature style. In 2010, Gwaai was involved in the Vancouver Playhouse Theatre's production of Bruce Ruddell's 'Beyond Eden' play. He participated in many aspects of the production, for which he received a Jesse nomination. Gwaai currently spends his time between making jewellery and sculpture. He has been carving for almost 20 years.