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After graduating with a degree in business, Ueberroth was turned down for jobs by several large companies, and the rejections deflated him. He decided to drift back to Hawaii, confident he could get work. That September he married the daughter of a Long Beach baker, Ginny Nicolaus, whom he had known for a couple of years at San Jose. Together they lived in a one-room Oahu apartment, so small, remembers Ginny, that they could almost reach out and touch all four walls from the center of the room. Ueberroth, now 22, became operations manager for a small nonscheduled airline owned by Kirk Kerkorian, the adventurous entrepreneur who later took over MGM. The service, Trans International Airlines, had been set up to bring passengers from California to Hawaii and back. Ueberroth created a market, overlooked by the big jet lines: luring new customers out of the scattered islands and sending them to the mainland. A year later when Kerkorian offered to bring him to Los Angeles to run the whole airline at double his $1,000-a-month salary, the young man showed he could drive a hard bargain. He held out for part ownership and got 3%.
Shortly thereafter, Ueberroth left and started his own air service between L.A. and Seattle. Hotel rates suddenly shot up, travel dropped, and he found himself $100,000 in debt. It was one of the few times he was truly scared. But he had another idea. It had seemed to him that small airlines, small hotels, steamships and others that could not afford representatives in several cities could use a reservation service. He set up a phone bank in Los Angeles for a few dozen customers, each dutifully listed in local directories. If someone telephoned Alaska Airlines, or Aloha Airlines, or Ethiopian Air Lines, Ueberroth would answer just as though a local office existed. Soon he had a dozen such operations around the country. By 1965 the company, Transportation Consultants, was rolling up big revenues. Ueberroth was invited to join the Young Presidents' Organization, one of its youngest members ever. He was 28.
Next he took his company public and with the cash began buying up small travel agencies, then expanded into hotel management and eventually purchased several 50-room hotels. Soon the company had ten, generating lots of revenue, and in 1972 when a large old travel agency called Ask Mr. Foster came up for sale, Ueberroth grabbed it, putting up nearly $1 million in cash. By 1978, carried along by the boom in the travel and leisure market, his parent company, now called First Travel, had 1,500 employees in 200 offices worldwide and gross revenues in excess of $300 million, making it the largest U.S. travel company after American Express.
Along the way Ueberroth developed a disciplined, fastidious style.