Steve Jobs left behind a reputation for being a creative genius who could do no wrong.
In fact, he was only human; like anyone else, he had brilliant moments, but he also made mistakes. Insanely Simple, a new book by Ken Segall, a creative advertising director worked with Jobs at various ad firms including the TBWA\Chiat\Day, lays out both.
The book's title lays out what Segall thought of as Jobs' key strength. He talks about  Jobs wielding (metaphorically) the "simple stick":
The Simple Stick symbolizes a core value within Apple. Sometimes it's held up as inspiration; other times it's wielded like a caveman's club. In all cases, it's a reminder of what sets Apple apart from other technology companies and what makes Apple stand out in a complicated world: a deep, almost religious belief in the power of Simplicity.
As for the mistakes ...
Steve's idea was to do a Willy Wonka. . . Just as Wonka did in the movie, Steve wanted to put a golden certificate representing the millionth iMac inside the box of one iMac, and publicize that fact. Whoever opened the lucky iMac box would be refunded the purchase price and be flown to Cupertino, where he or she (and, presumably, the accompanying family) would be taken on a tour of the Apple campus.
Steve had already instructed his internal creative group to design a prototype golden certificate, which he shared with us. But the killer was that Steve wanted to go all out on this. He wanted to meet the lucky winner in full Willy Wonka garb. Yes, complete with top hat and tails.
Due to the intricacies of California sweepstakes regulations, the giveaway never happened, and Jobs instead developed a reputation for never wearing anything but his trademark jeans, trainers and turtleneck sweater. Which, it has to be said, is probably for the best.