Steve Jobs got rich the Silicon Valley way: buy low, sell high, repeat. He bought Pixar for $10M in 1986 when it was a bleeding-edge graphics division spun out of Lucasfilm, then sold it to Disney for $7.4B in 2006 after proving computer animation could print money. That single deal—a 740x return—bankrolled most of his $10.2B net worth. Meanwhile, 83% of his Apple wealth came from stock he held at death, not from salary. Jobs played the arbitrage game masterfully: identify undervalued assets, prove their worth, cash out. The man was a venture capitalist wrapped in a turtleneck.

Walt Disney, by contrast, was a builder, not a trader. He died in 1966 holding significant Disney stock, but here's the brutal math: he cashed out or gifted shares throughout his life, and his personal estate topped out at roughly $5B in today's dollars. He wasn't playing the long game with equity; he was reinvesting everything back into the studio. If Walt had been a passive investor in his own company—if he'd simply held and done nothing—his heirs would own a $200B+ stake today. He built the machine but never monetized it the way Jobs did with Pixar.

The real lesson isn't that Jobs was greedier; it's that timing and exit strategy matter more than empire size. Disney created the bigger, more durable business—it's literally a $200B company now. But Jobs recognized that the real wealth wasn't in running Apple forever; it was in spotting Pixar's potential before the world did, then letting Disney's balance sheet do the heavy lifting. Walt built a legacy. Steve Jobs built a payday. Both died rich, but only one understood the assignment.