Maile is co-founder of Ka Hale Hoaka, a school of Hawaiian Learning based out of her off-grid home in Honouliwai Valley where she creates cross-disciplinary courses and learning resources taught through a Hawaiian lens. Her teachings are grounded in Indigenous philosophies and practices such as mo’olelo, ʻōlelo Hawai’i, hula, and oli. She is also the director of the Molokaʻinuiahina project, a multi-generational community art project founded on traditional storytelling. Maile is the director of Hoʻokupu - A Hip Hop Anthology of Hawaiian History which includes an album and textbook resource used in schools throughout Hawaiʻi. In 2023 she was awarded a Na Hōkū Hanohano award for best Hip-Hop album of the year for the Hoʻokupu project. By teaching via various art mediums through the vessel of moʻolelo she emphasizes the great importance of building communication skills, self-confidence, and a new generation of storytellers. It is based on the belief that the ancient wisdom of our ancestors is the answer to our modern-day problems.