John was born in California and spent his childhood in the Boston area. He began his career in the entertainment industry while attending Brown University in the 1970s, where he was cast in the sequel to Jaws, Jaws 2.
John continued to work as an actor for the next six years, landing substantial roles in films such as Making Love, Delusion, and Split Image, as well as television shows like Family Ties, Little House on the Prairie, and Taxi. He also appeared in the Jim Jones docudrama, Guyana Tragedy: The Story of Jim Jones.
After retiring from acting, John moved to Washington, D.C. to work as a legislative assistant to U.S. Sen. John Kerry. In 1987, his father, then-Gov. Michael Dukakis, announced his intention to run for President, and John left Washington to help with the campaign.
John's work with the Dukakis campaign led to a job as the National Political Director, and he spent the months leading up to the 1988 presidential election campaigning across the country. After the election, John began working with an attorney in Boston named Bob Woolf, who represented professional athletes.
John ran the music business management department for Woolf's company and helped develop a local act, New Kids on the Block. Within a few years, the company grew, and John was sent to Los Angeles to open an office and work with established and developing acts.
When John left Woolf's company in 1992, he went on to become the general manager of Paisley Park Records, a joint venture between Prince and Warner Bros. Records. During his tenure, the company released projects from Prince, George Clinton, and Mavis Staples.
In 1994, John formed a new venture, Southpaw Entertainment, with his partner, Qadree El-Amin. The company primarily focused on managing Boyz II Men, but after the group's success, it took on new clients, including Janet Jackson, Vanessa Williams, Brownstone, and Blackstreet.
In early 2002, John left Southpaw to become an Executive Vice President of Overbrook Music, a music label and management company owned by Will Smith and James Lassiter. The company released soundtracks for films like Wild Wild West and Love and Basketball, as well as managed artists like Christina Vidal, Jordan Knight, and Samantha Mumba.
John retired from the music industry in 2008 and has been living and working in Boston since then.
