By his own admission, Stewart Crawford’s early academic career at MIT was undistinguished. “A combination of immaturity, too many frat parties, several part-time jobs at a time, and I guess, a rebellion against authority led to my academic suspension,” he says. However, he reapplied and graduated on time with a degree in management.

Crawford got his favorite part-time gig—chauffeuring for philanthropist Claire Morton Prince Hanks—when he responded to a notice at the Student Aid office. He picked her up at the Ritz-Carlton and ferried her all over town in her big Buick. “She knew everybody,” Crawford says. One day—“This is how gauche I was,” he says—he asked Mrs. Hanks her age. “She said, ‘Stewart, a woman who would tell her age would tell anything.’”

Crawford’s own vehicle at the time, a 1933 Packard, was the first of many classic cars he owned over the years, including a Pierce Arrow and five other Packards. “I’m not interested in anything past 1950,” he says. He has judged at classic-car concours and written for car collector magazines.

After MIT, Crawford worked in the corporate world in Puerto Rico, Chile, and Mexico before landing in Los Angeles as a management consultant for companies in financial difficulty. He headed his own firm for 15 years before needing a change himself. “I got sick of working with people who’d dug their own financial graves,” he says. One day while reading the paper, Crawford saw an ad for a “unique publishing company.” He bought U.S. Traffic Service (USTS), one of about 20 ocean-shipping tariff publishers that maintain databases of shipping rates. USTS’s clients pay a wholesale rate to vessel owners for the use of their shipping containers and then sell the space in the containers at retail rates to companies with cargo to ship.

A glee clubber at MIT, Crawford recalls performing at Jordan Hall at New England Conservatory of Music. He has sung in and directed church choirs for years. “I sometimes still solo,” he says. He also provides churches with free financial consulting.

Crawford married his first wife, Doris Young, the day after graduation. They were together for 36 years and raised three children before she died. Crawford is now married to Nelva McGee-Crawford, a real-estate broker. They have homes in Murrieta, California, as well as Nelva’s native Panama and his hometown of Keene Valley, New York—where he keeps his 1940 Cadillac.