Steve Jobs considered a free, ad-supported version of Mac OS 9

In his new book, Ken Segall says that Steve Jobs and his team at Apple explored the possibility of shipping a free, ad-supported version of Mac OS 9. Segall says Jobs was considering the option because of the profit potential inherent in selling software updates: “this is how Microsoft does it... it’s like printing money,” Jobs said. The plan was to give users a sixty-second commercial upon starting up the system that would be remotely updated by Apple, and to place ads elsewhere in the OS where they had the most relevance — like an Epson ad next to a system notice for low ink. He says that the team found the concept “financially sound,” and that Steve was intrigued by the idea, but later “it appeared that too many negatives had come up” and it was killed.