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The Most Gangster Story in Silicon Valley: Steve Jobs Cutting Personal Checks to Keep Pixar Alive

By Steve Jobs · Investing · 2 min read

Jobs bought Pixar for $5M. Invested $50M. Lost money for a decade. Then turned it into $7.4 billion.

Key Points

Steve Jobs ran two failing companies for 10 years after being fired from Apple.
He invested $50M+ of his own money into Pixar while it generated no revenue.
NeXT's operating system ended up saving Apple by becoming macOS.
Going the distance is the most underrated advantage for entrepreneurs.

He kept going for 10 years. How do you do that?

Ten Years in the Desert

People think of Steve Jobs as the iPhone guy. The iPad guy. The keynote guy. Amjad Masad from Replit thinks about a different Steve Jobs. The one who wandered the desert for a decade.

After Apple fired him, Jobs started two companies. NeXT Computing and Pixar. Both were failing. For years. Neither made money. He just kept investing his own cash.

Most people remember Jobs for the iPhone. The real story is the 10 years of failure before it.

Personal Checks for Payroll

Pixar was bleeding money. No revenue. No path to revenue. Jobs was writing personal checks to make payroll. He was going broke keeping a dream alive.

Then Pixar made Toy Story. The company went from nothing to billions in public value. All because one man refused to quit for ten years.

Jobs was cutting personal checks to keep Pixar's lights on. That's conviction.

The NeXT Surprise

Everyone thought NeXT was a total failure. Masad himself assumed Apple just bought Steve back as an acqui-hire. Wrong.

Apple needed a new operating system. Intel was the future. Their internal OS couldn't compete. NeXT had built a great one. Objective-C. Unix-based with serious innovations. NeXT's OS became macOS. The 'failure' saved Apple.

NeXT wasn't a failure. Its operating system became the foundation of modern macOS.

Going the Distance

Masad's takeaway is simple. Going the distance is an advantage. Most people quit when things stop working. Jobs kept going for a decade with two companies that weren't selling anything.

That persistence isn't stubbornness. It's conviction backed by personal sacrifice. He wasn't spending other people's money. He was spending his own.

Jobs didn't invest other people's money. He invested his own. For a decade.

The Gangster Move

Buy Pixar for $5 million. Invest $50 million more. Operate at a loss for ten years. Cut personal checks for payroll. Nearly go broke. Turn it into a $7.4 billion exit.

That's the most gangster story in Silicon Valley. Not because of the money. Because of the will.

$5M purchase. $50M investment. 10 years of loss. $7.4B exit. That's gangster.