Born in 1956 on a farm in Bloomington, Illinois, he studied American history at Yale University and Gandhi's independence movement at Andhra University in India.

Ashbrook worked in Alaska as a surveyor and dynamiter of oil fields before leaving for Asia, where he spent a decade as a foreign correspondent in India, Hong Kong, and Tokyo. His first newspaper job was at the South China Morning Post. During the late 1980s, Ashbrook became foreign editor for The Boston Globe.

Ashbrook was a Nieman Fellow at Harvard University during which time he decided to leave the Globe in 1996 and create an internet startup with college friend Rolly Rouse. This company eventually became http://www.homeportfolio.com/. Ashbrook wrote a book called The Leap about his experience in Internet entrepreneurship, and currently hosts the National Public Radio show On Point. Ashbrook underwent heart bypass surgery in November 2007 and was off air until January 2, 2008, when he discussed his medical journey in a show with his doctors and nurses.

Tom Ashbrook has a wife, a daughter, and two sons. He lives in Newton, Massachusetts.