The idea, never implemented, would give customers a free version of the Mac operating system in exchange for occasional advertisements that users would be forced to watch.
Mr. Segall explains that customers would still have the option to purchase the standard version of OS 9, but those without the desire to pay could upgrade to the latest version if they were willing to endure mandatory advertising:
Rather than charge the normal upgrade price, which in those days was $99, he was thinking of shipping a second version of Mac OS 9 that would be given away for free – but would be supported instead by advertising. The theory was that this would pull in a ton of people who didn’t normally upgrade because of the price, but Apple would still generate income through the advertising. And any time an owner of the free version wanted to get rid of the advertising, he or she could simply pay for the ad-free version. Steve’s team had worked out the preliminary numbers the concept seemed financially sound.
Foreshadowing the success that companies like Google would later have with contextual advertising, Mr. Jobs reportedly envisioned the OS ads as being relevant to the user, with new content being delivered on demand over the internet. Ads for printer ink would display when the computer reported that the printer was low on ink, for example.
Thankfully for users averse to obtrusive advertising, Apple never implemented the idea and, with iOS and OS X now generating revenue through app sales, it is unlikely that they ever will.
Insanely Simple is available on iBooks for US$12.99.