Chambers was born in
Dorchester,
Massachusetts and was the son of a commercial artist and a homemaker. He grew up in a two-family home owned by his maternal grandmother. At the age of 13, Chambers' mother started charging him $15 per week rent and this was when he started working at the
Stop & Shop supermarket in the neighborhood. He did very well at the market, earning promotions and raises, but his school work at
English High School of Boston suffered. He ended up dropping out of high school in his senior year. In 1983, Chambers sold the A-Copy business to Alco Standard Corporation for a reported $80 million and he continued to work with the company for another two years. As Chambers improved the operations of this first car dealership, he started the Herb Chambers Companies. In May 2017, Chambers was awarded the New England Motor Press Association Executive of the Year Award for his outstanding contributions to the automotive industry. == Exotic car collector ==