How small companies will always challenge big (the main idea behind The Innovators Dilemma).
How difficult starting a business is (success or failure being mostly down to perseverance).
How San Francisco became such a hotbed of invention (his answer: music, hippies, LSD and exceptional colleges).
I've been reading Jobs' biography which is long but pretty good. What really struck me was his complete respect for artists. He understood the hard work behind great art and creativity ("Genius: one percent inspiration and 99 percent persperation" as Edison and Michaelangelo are both meant to have said).
He often talked about Apple existing at the intersection of art and technology. As Andy Hertzfeld (who was on the original Mac team but is now at Google) says 'Jobs thought of himself as an artist, and he encouraged the design team to think of ourselves that way too. The goal was never to beat the competition, or to make lots of money. It was to do the greatest thing possible, or even a little greater.'
He was a terrible manager, awful to work for in traditional ways (rare praise, inability to delegate, used lies and manipulation excessively) but he knew all of this. The reason he was such 'an asshole' (his words) was because he honestly believed he was facilitating people to create the best work of their lives (they almost universally agree with this).
"He would shout at a meeting, 'You asshole, you never do anything right," Debi Coleman recalled. "It was like an hourly occurrence. Yet I consider myself the absolute luckiest person in the world to have worked with him."