Keola cites his kupuna as the core of his education, inspiration and growth, especially his own Kūkū Julia Waineʻe, Kumu Keola Lake (oli/hula), Aunty Margaret ʻAipoalani (mele/moʻolelo), ‘Anakala Eddie Ka’anana (loʻi), Kumu Alvah (lomilomi), Kanalu Young and Captain Clay Bertelmann. Other sources of learning, grounding, and inspiration include various lo’i (taro farms), loko i’a (traditional fishponds), waʻa (surfing and sailing canoes), heʻenalu (surfing) and weekly kanipila sessions held at his hale for over a decade.
His formal education includes public schools on West Oʻahu, Kamehameha Schools, a B.A. Degree in Economics at Occidental College, and an M.A. in Pacific Islands Studies at the University of Hawai`iat Mānoa, with an emphasis in Education and Hawaiian Studies.
Keola is the founder/Executive Director of Mana Maoli (MM), and founder/former Principal of Hālau Kū Māna Public Charter school (HKM). MM started off doing monthly events, then weekly classes for its host communities, Papakolea and Maunalaha Valley Homesteads, before formalizing its 501(c)(3) status and starting HKM, the first school on O‘ahu to receive its charter, opening its doors in 2001, with community, culture and environment-based curriculum. A few years later, Keola was recognized nationally for his efforts with MM and HKM as one of the ‘Top 20 Leaders Under 30’.
Keola continued to serve as both Principal of HKM and ED of MM until his daughter Kui was born in 2007, upon which he focused only on his kuleana with MM. From this point, he was able to focus more on fundraising and growth for MMʻs sailing canoe program, Kānehūnāmoku Voyaging Academy, until this program grew in scope to warrant forming their own nonprofit in 2012. This in turn paved the way to focus on growing MMʻs music programs, which in 2013 became the ʻMana Mele Projectʻ, consisting of a Music & Multimedia Academy, a solar-powered mobile studio, and a collective of over 200 Creative Industriesʻ Professionals. Today, Mana Mele serves thousands of youth across 20 partner schools on 3 islands.