In 1970, Stinson first worked professionally in Dottie West's band the Heartaches, touring with Red Sovine and Don Gibson, and appearing on the Grand Ole Opry.
[1][2] Then Stinson moved to California, where he joined the band Silver with John Batdorf, Tom Leadon, Brent Mydland, and Greg Collier.
[6][7] In the mid-nineties, Stinson founded Dead Reckoning Records with Kieran Kane, Kevin Welch, Tammy Rogers, and Mike Henderson.
[15] Stinson has worked with Jimmy Buffett, Jay Ferguson, Al Stewart, Etta James, Peter Frampton, Juice Newton, Elton John, Bob Seger, Leon Russell, Corb Lund, Lyle Lovett, Steve Earle, Bette Midler, Faith Hill, Patty Loveless, George Jones, Nicolette Larson,[16] Neil Diamond, Lyle Lovett, and Earl Scruggs.
[17] Stinson was a member of TNN’s American Music Shop house band, with Mark O'Connor, Jerry Douglas, Brent Mason, Glenn Worf, John Jarvis, and Matt Rollings.