Roy and Estelle Kelley were married in 1929 and, that same year, moved to Hawaiʻi where Roy went to work for the noted Hawaiʻi architect C.W. Dickey. With the stock market in shambles, 1929 was not an auspicious year to begin a career or settle into a faraway chain of islands. After working on several architectural assignments (including the main building of the Halekūlani hotel), Roy struck out on his own in the late 1930s, building residential buildings. Following the war, Roy and Estelle saw a very bright future in tourism – and ended up being the pioneers helping to make that vision a reality. The Kelleys began their hotel operations in 1947, opening The Islander, a four story walk-up Waikīkī hotel with 33 rooms.
A true team, the Kelleys made their operations a family affair, getting everyone involved in the business of satisfying guests at what became known as Outrigger Hotels. Roy managed the operations and Estelle managed the reservation system, which became a key to the growth of the business. Ever the innovators, they had the first hotel in Waikīkī with an automatic elevator or a swimming pool.