Although surfing was consuming more of his life as he grew older, Kekai managed to concentrate on his school work and excelled academically.

He was offered athletic scholarships to attend college, but chose to enter the workforce after high school, and earned a living on and off the beach through numerous odd jobs.

Like most young American men of the time, Kekai served in the military during World War II, and was fortunate to be stationed in Haleiwa on the North Shore for part of his service.

He worked on the Underwater Demolition Teams, or UDTs, that operated in the Pacific Theatre deploying depth charges to destroy Japanese ships and clear the way for American troops to capture the Federated States of Micronesia from Japan.

By the 1950s, Kekai made a point of passing on the surfing techniques he had acquired over the years to a younger generation, including Joey Cabell, Donald Takayama, Harold Iggy and many others.