I can offer no personal testimonial for Jobs, as I didn’t know the man. But I can speak to his generation.
Page through Jobs’ history and it’s clear that he strongly felt the influence of his time. Like his pop-idols, he grew out his hair, dropped acid, traveled to India, and worked with the naive confidence—so common in those days—that anything was possible. However, unlike nearly everyone who followed this well-worn path, he didn’t crash and burn or descend into cynicism when life inevitably crushed the fragile fantasies that made up much of ’60s culture.
Rather than dismiss the experiences of his youth, he synthesized and prioritized them. It was cool to be an artist. It was cool to be a non-conformist. It was cool to believe that nothing was impossible. Similarly, it was uncool to be a Suit. It was uncool to sell or be plastic. It was uncool to be afraid.
It was uncool to be uncool.
Jobs brought this experience and attitude to Apple. It was omnipresent in Apple’s early days—the and commercials, the pirate flag that floated over Apple’s campus, the “How many times have you dropped acid?” interview questions, and just about everything about the Mac’s design and interface.