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Herbert G. Chambers is owner and CEO of Herb Chambers Companies, a group of 50  car dealerships in the greater Boston, Massachusetts, area. A directory of Herb Chambers Car Dealerships lists their OEM brand portfolio in Massachusetts and New England.
After the Navy, Chambers began working as a copy machine repairman in Cambridge, Massachusetts. By the time he was 22, he had started his own copier distribution company with money borrowed from his parents. He fixed copy machines door-to-door. He eventually sold the business for $80 million.
Chambers started his automotive business after purchasing a Cadillac dealership in New London, Connecticut, in 1985. His decision to purchase the business was based on his own poor buying experience at the dealership. As Chambers improved the operations of this first car dealership, he started the Herb Chambers Companies.
In 2007, The Boston Globe carried an article and photo gallery highlighting Chambers' car collection. His collection of rare automobiles includes the McLaren F1, Mercedes-Benz SLR McLaren, Ferrari Daytona Spyder, Ferrari Daytona Coupe, 2006 Ford GT, Porsche 959 Supercar, 2006 Porsche Carrera GT, Cadillac Eldorado Biarritz Convertible, Ford Model B (1932) and a 1955 Mercedes-Benz 300SL that was raced in the 1983 Cannonball Run.