Kanae Kobayashi was born into the family hotel business, founded when his father and uncle opened the 10-room Kobayashi Hotel in 1892 to accommodate Japanese immigrants. Although the hotel was accidentally destroyed in the 1900 Chinatown fire, the Kobayashi family started over.
At the age of 10, Kanae was sent to Japan to study, eventually earning a business degree from the University of Waseda. During the war he served as an interpreter for the army until 1946 when he rejoined the family business. In post-war Hawaiʻi, Kanae and his brothers, Hichiro and Tatsukichi, built the business from a single hotel into an enterprise that included three retail travel agencies, a wholesale outbound tour operation, ground handling, an inbound tour option operation, and ground transportation on Oʻahu , Hawaiʻi, and Maui. As Hawaiʻi tourism grew and evolved, so did the company.