In 2015, frustrated by the explosion of homelessness in Hawaii and dwindling compassion for those on the street, James pitched a tent in a large urban encampment and sought to understand homelessness from the "ground up." Through friends me met on the street, he was introduced to and became a core supporter of Puuhonua O Waianae, a self-organized village of more than 250 people living unhoused at the Waianae Boat Harbor. These experiences helped him understand homelessness as a problem of severed connections with place and community. He co-founded Hui Aloha, to demonstrate how building community with those who are marginalized is key to solving homelessness. He was born and raised on Oahu, and earned degrees from Brown University and the Harvard Kennedy School of Government. His work is inspired by ancestors who immigrated to Hawaii and survived thanks to the Aloha of Hawaii's native people. In January 2023, he was appointed by Gov. Josh Green as the Governor's Homeless Coordinator.