One of his brothers, John Montgomery, also worked in the music industry before becoming an entrepreneur in the Metro Detroit area.

His younger brother, Jeffrey Montgomery, was an LGBT activist, primarily known for being the founding executive director of Triangle Foundation (today Equality Michigan).

[3] During his junior year, he was hired by the Colwell-Winfield Blues Band to play harmonica and tour with Janis Joplin.

By the time he graduated from college his band was on the cover of the Boston Phoenix, heralded along with J. Geils and Aerosmith as the city's great contributions to the music world.

King, Muddy Waters, Buddy Guy, John Lee Hooker, Junior Wells, James Cotton, Bonnie Raitt, Steven Tyler, Brad Whitford, Charlie Daniels, Gregg Allman, LaVern Baker, Patti LaBelle, Jonathan Edwards, Jerome Geils, Peter Wolf, Magic Dick, Danny Klein, Huey Lewis, Kim Wilson, Elliot Easton, Johnny A., Rick Derringer, Ricky Byrd, Rob Kogut, Barry Goudreau, Fran Sheehan, Sib Hashian, Chad Smith, Billy Squier, Michael Carabello, Jon Butcher, Bruce Marshall, Dennis "Fly" Amero, Duke Robillard, Jon Pousette-Dart, Kate Taylor, Christine Ohlman, Mike Finnigan, Grace Kelly, The Uptown Horns, James Brown, The Rolling Stones, and Joe Cocker.

Montgomery recalls the night he played with Muddy Waters at Paul's Mall in Boston, Massachusetts.