Steve Jobs

The biggest misconception about Steve Jobs is that Apple made him rich. When Disney acquired Pixar in 2006 for $7.4 billion, Jobs walked away with $7.4 billion in Disney stock, instantly becoming Disney's largest individual shareholder. Meanwhile, his Apple stake was worth 'only' around $2 billion at his death in 2011. This wasn't an accident—Jobs had been systematically diversifying away from Apple since the late 1990s, understanding that no matter how successful the company became, concentration risk was still risk.

Jobs' genius wasn't just in product design but in deal structure. When he bought Pixar from George Lucas in 1986 for $10 million, he negotiated unusual creative control and profit participation that most Hollywood studios would never accept today. Each Pixar film generated hundreds of millions in revenue, but the real wealth came from merchandising and licensing deals. By 2006, Pixar had produced seven consecutive hits, and Disney was desperate enough to pay premium prices to avoid losing their golden goose to competitors.

What's fascinating is how little Jobs actually spent relative to his wealth. His Palo Alto mansion cost just $2.3 million in 1991, and while he owned a $138 million yacht and collected rare art, his lifestyle was remarkably modest for a billionaire. He famously drove without license plates and wore the same black turtleneck daily—not just for brand reasons, but because decision fatigue was inefficient. This frugality meant more capital stayed invested and compounding, turning his Pixar windfall into an even larger Disney position that continued growing after his death.