Jobs' calls to Appleseed became more frequent in 1985 when his working relationship with Apple CEO John Sculley became a power struggle. "Steve was pretty paranoid back then," our source recalls. "John was one of the few people he knew who didn't have an agenda."
Jobs' career moves are well documented, but Appleseed's are more sketchy: his jobs were mainly temporary - moving from firm to firm in Silicon Valley, unconcerned with carving out a particular career. He never did get that Apple job, but in the late 80s he made a second Apple connection: he met and began to date Kate Shannon, who worked in Apple's accounting department. He and Kate were married in 1991 and they had a daughter, Jane, in 1993.
Jobs' phone calls were less frequent in the early 90s: Jobs had a family and two companies - NeXT and Pixar - to run, and that didn't leave much time for anything else. But by 1996 Jobs was back at Apple, and the phone calls resumed their previous frequency - and Appleseed would end up angry at Apple for a second time.
Take a look at the TextEdit icon in OS X. If you blow it up or zoom in on the graphic to read the writing on the pad, you'll see that it's a note to Kate from John Appleseed. "Here's to the crazy ones," it says. "The misfits. The rebels. The troublemakers."
"Everybody thinks Apple's ad agency came up with the 'crazy ones' spiel," an Apple insider told us. "But they didn't. It was Appleseed's idea, and Steve ran with it. The icon's a nod to Appleseed, an inside joke."
As our source tells it, the real story is this: Appleseed and Jobs were talking about Jobs' personal philosophy, and the philosophies of Apple's rivals. "You think different," Appleseed told him. "You're crazy enough to think you can change the world." Maybe Jobs felt guilty for taking the credit, but shortly after the "Think Different" campaign began he sought Appleseed's opinions more often, using him as a soundboard not just for Jobs' ideas, but for actual products too. Appleseed may not have been an Apple employee, but he was an Apple insider.
The seeds are sown
At first, Appleseed was delighted. He got sneak peeks of new products. Jobs asked his opinion on pre-production hardware. Appleseed was one of the first to see the iPod, and the iPhone, and the iPad, Jobs convinced that Appleseed would stay silent - something that worried other Apple executives.
"Steve wouldn't listen to them," our source says. "To him, Appleseed was some kind of mascot, a lucky penny or something." Our source compared him to the rapper, Flavor Flav. "You know how Flavor Flav doesn't really do anything, but Chuck D likes having him around? Appleseed was like that."
Appleseed wasn't just Steve Jobs' court jester, though. He became part of the marketing team - albeit without anybody telling him. Apple marketing materials don't just appear overnight: they're carefully planned and designed far in advance, and that means the marketing team needs photography and screenshots in advance, too. As far as Jobs was concerned, the fewer people who actually knew about unannounced products, the better - so why not get your real-world examples from someone that you already know and trust?
The first that Appleseed knew of his new role was at Macworld '07, when Steve Jobs introduced the iPhone. "John nearly jumped out of his seat when he saw his face on the screen," our source recalls. "Jobs hadn't mentioned it to him. He'd just assumed it would be okay." It wasn't, because as part of the keynote Apple showed a video of the iPhone being activated - and that video showed Appleseed's real mobile number (408-550-3542) and email address (firstname.lastname@example.org).