Date: 2002

While other music powerhouses like Universal and Warner were quick to license its catalogs to Apple, Sony wasn’t rushing to drink the Kool-Aid. Former CEO Andy Lack knew Jobs initial purpose was to mainly sell hardware and nothing more. So he argued that Apple should pay royalties to the music companies for every iPod sold. Jobs disagreement obviously led to the foreseen rejection from Lack: a move the tech giant took extremely personal as indicated in his biography. “With Andy, it was mostly about his big ego. He never really understood the music business, and could never really deliver. I thought he was sometimes a dick,” Jobs told biographer Walter Isaacson.