Here's What It Was Like Pitching To Steve Jobs
So it comes as no surprise that pitching Jobs on basically anything would be an uphill battle.
A few people have chimed in on this topic on Quora.
"[It was] scary, but also kind of cool," said Paul Weinstein. "I was an outsider pitching a product (there were 3 of us) and he just savaged his own team in front of me."
Jobs spared Weinstein any personal disparagement, but didn't fail to leave an impression.
"At one point in the meeting he asked me what my name was and then when I told him, he said 'Paul Weinstein is the only guy here who knows what the fuck he is talking about' and then left," said Weinstein.
Others characterized Jobs as nicer, but nevertheless a perfectionist:
"He had come to see a new version of some software we were working on at Apple (he had been really happy with the previous version), and we were showing him early mockups," said Mike Kobb. "Although I didn't agree with some of the stuff he wanted to do, you could definitely tell that this was a really smart and passionate guy, really engaged with the discussion."
Apple's CEO was more than able to intimidate outsiders, wrote Kat Makinney:
"He had that presence that said, 'I'm smarter than you, I'm better than you and we both know it,'" she said. "I tried to ignore it but it was intimidating. Which was his goal. He leaned back and listened, asked a few questions and then got to it - he wanted it for nothing. Then the negotiations began."
Jobs used his intimidating presence to drive some of Apple's biggest deals, like getting record labels to sell their music on iTunes.
But if those who dealt with Jobs found him taxing or intimidating, they also tended to respect him as well.
That combination of qualities is how Jobs developed a reputation as an innovator.