People were allowed, even encouraged, to challenge him, and sometimes he would respect them for it. But you had to be prepared for him to attack you, even bite your head off, as he processed your ideas. “You never win an argument with him at the time, but sometimes you eventually win,” said James Vincent, the creative young adman who worked with Lee Clow. “You propose something and he declares, ‘That’s a stupid idea,’ and later he comes back and says, ‘Here’s what we’re going to do.’ And you want to say, ‘That’s what I told you two weeks ago and you said that’s a stupid idea.’ But you can’t do that. Instead you say, ‘That’s a great idea, let’s do that.’”
People also had to put up with Jobs’s occasional irrational or incorrect assertions. To both family and colleagues, he was apt to declare, with great conviction, some scientific or historical fact that had scant relationship to reality. “There can be something he knows absolutely nothing about, and because of his crazy style and utter conviction, he can convince people that he knows what he’s talking about,” said Ive, who described the trait as weirdly endearing. Yet with his eye for detail, Jobs sometimes correctly pounced on tiny things others had missed. Lee Clow recalled showing Jobs a cut of a commercial, making some minor changes he requested, and then being assaulted with a tirade about how the ad had been completely destroyed. “He discovered we had cut two extra frames, something so fleeting it was nearly impossible to notice,” said Clow. “But he wanted to be sure that an image hit at the exact moment as a beat of the music, and he was totally right.”
Ed Woolard, his mentor on the Apple board, pressed Jobs for more than two years to drop the
The main reason he clung to his
Woolard was thrilled, and he suggested that the board was willing to give him a massive stock grant. “Let me be straight with you,” Jobs replied. “What I’d rather have is an airplane. We just had a third kid. I don’t like flying commercial. I like to take my family to Hawaii. When I go east, I’d like to have pilots I know.” He was never the type of person who could display grace and patience in a commercial airplane or terminal, even before the days of the TSA. Board member Larry Ellison, whose plane Jobs sometimes used (Apple paid $102,000 to Ellison in 1999 for Jobs’s use of it), had no qualms. “Given what he’s accomplished, we should give him five airplanes!” Ellison argued. He later said, “It was the perfect thank-you gift for Steve, who had saved Apple and gotten nothing in return.”
So Woolard happily granted Jobs’s wish, with a Gulfstream V, and also offered him fourteen million stock options. Jobs gave an unexpected response. He wanted more: twenty million options. Woolard was baffled and upset. The board had authority from the stockholders to give out only fourteen million. “You said you didn’t want any, and we gave you a plane, which you did want,” Woolard said.
“I hadn’t been insisting on options before,” Jobs replied, “but you suggested it could be up to 5% of the company in options, and that’s what I now want.” It was an awkward tiff in what should have been a celebratory period. In the end, a complex solution was worked out that granted him ten million shares in January 2000 that were valued at the current price but timed to vest as if granted in 1997, plus another grant due in 2001. Making matters worse, the stock fell with the burst of the Internet bubble. Jobs never exercised the options, and at the end of 2001 he asked that they be replaced by a new grant with a lower strike price. The wrestling over options would come back to haunt the company.