Though Ackerman had played guitar since the age of 12, when he dropped out of college it was to become a carpenter, and his first company was called Windham Hill Builders. The Palo Alto native composed guitar music for Stanford University theater productions, and the encouragement of friends led him to record an album of his tunes, In Search of the Turtle's Navel, in 1976. The first release on his newly minted independent record label, Windham Hill, the album was surprisingly successful, and Ackerman soon found himself in the music business.
Since then, Ackerman has continued to record his own albums, to produce Windham Hill albums for such influential artists as George Winston, Shadowfax, Michael Hedges, Alex de Grassi, and Liz Story, and to serve in various capacities in the record company.
After selling Windham Hill in 1992, Ackerman relocated to Vermont and built his own studio, Imaginary Road, where he has continued to both produce and to record and release his own music. In 2018 he released the mid- to late-career retrospective Was It This Lifetime: Pieces for Guitar 1995-2011. ~ James Christopher Monger & William Ruhlmann, Rovi