[1] Living in New York, Freeman avidly collected recordings from Southern musicians including old-time, bluegrass, country and blues artists.

His new label's first release was a reissue of old-time music drawn from his personal collection of 78 rpm recordings from the 1920s and 1930s by Charlie Poole, the Leake County Revelers, Crockett's Mountaineers and similar string bands.

[citation needed] Around the same time, Freeman met Charles Faurot, an old-time banjo player from Chicago who was also living in New York.

[3] County Records also expanded into the bluegrass music genre, although Freeman preferred those artists who stayed the closest to their old-time roots.

In 1977, he started a regional wholesale distribution business for old-time and bluegrass music, Record Depot, in Roanoke, Virginia.

In 1978, Freeman helped his graphic artist Barry Poss start a new label in Durham, North Carolina called Sugar Hill Records.