In San Francisco in 1968, Donahue traded his hi-fi tape player to poet Charles Plymell to publish the first issue of Robert Crumb's Zap Comix on his printing press. Donahue later purchased the equipment and founded Apex Novelties, which published numerous influential comics from that movement, including work by S. Clay Wilson, Kim Deitch, Shary Flenniken, Justin Green, Bill Griffiths, Spain Rodriguez, Gilbert Shelton, Art Spiegelman. He was known for publishing material by radicals, including the Symbionese Liberation Army (best known for kidnapping Patty Hearst).