Skin in the Game

From Jamie Dimon's $60M bet to Marie Curie's radioactive notebooks: The essential courage of commitment in a world that fears risk.

In 1998, Jamie Dimon was unceremoniously fired from Citigroup. He was the heir apparent, but a power struggle with his mentor, Sandy Weill, left him ousted and publicly humiliated.

He was disappointed. He was also rich. He could have retired.

Instead, two years later, he took the CEO job at Bank One, a troubled regional bank in Chicago. Then he did something truly bold. He took $60 million of his own money—a massive chunk of his net worth—and bought 5.7 million shares of the bank he had just been hired to fix.

This wasn’t just an investment. It was a statement. It was Dimon, fresh off his biggest failure, putting his entire reputation and fortune on the table. He was signaling to every employee, every investor, and every analyst that his fate was now welded to theirs.

He had skin in the game. We know how that story ended: Bank One turned around, merged with JPMorgan, and Dimon became one of the most formidable bankers of his generation.

The Currency of Focus

We tend to think “skin in the game” just means money. It’s the easiest thing to measure. But real skin in the game is often paid in currencies that are far more valuable: time and focus.

When Steve Jobs returned to a dying Apple in 1997, the company was making dozens of beige boxes. They had a sprawling, unfocused product line and were 90 days from bankruptcy.

Jobs didn’t just invest money. He put his entire legacy—the one he had already built at Apple, NeXT, and Pixar—on the line. His first move was an act of brutal, sacrificial focus.

He famously walked to a whiteboard and drew a 2x2 grid: “Consumer” and “Pro” on one axis, “Desktop” and “Portable” on the other. “This is our product line,” he declared, slashing everything else. He said “no” to good ideas so he could say “yes” to four great ones.

That was his skin in the game. He staked his reputation on the belief that focus, not diversification, was the only way to win.

If that’s not enough, consider Marie Curie. She didn’t just invest time in her research on radioactivity; she invested her life. She and her husband, Pierre, worked for years in a drafty shed, painstakingly isolating radium from tons of pitchblende. They suffered from radiation burns and chronic illness.

Today, more than 100 years after her death, her notebooks are still so radioactive they have to be stored in lead-lined boxes. That is existential skin in the game. She paid for her discoveries with her own health, betting her one life on the pursuit of knowledge.

The Dilemma of the Open Door

These stories feel epic, almost foreign. Because today, we are taught the exact opposite lesson.

The modern dilemma, especially for young people, is a world that preaches “structured aimlessness.” We’re told to keep our options open. Build a portfolio of side hustles. Job-hop to climb the ladder. Quiet quit to protect your energy.

The narrative is: Don’t commit.

This is a culture that fears risk. It’s an endless buffet of options, gig economy projects, and half-interests that prevents us from ever having to choose one thing and go all in. We hedge. We diversify our time, our focus, and our identities.

But this “safety” is an illusion. It’s a strategy that protects you from a big, spectacular failure, but it guarantees a thousand tiny ones. It’s a recipe for mediocrity.

You can’t hedge your way to an outlier outcome. You can’t get a 100x return on a 1% investment of your focus.

The only way to make something out of life, to build something that lasts, to truly master a craft, is to put your skin in the game. It demands courage in the face of uncertainty. It requires you to “burn the ships,” leaving no path for retreat.

Boldness rules.

My Fourth Rodeo

This isn’t just theory for me. It’s the only way I’ve ever known how to operate.

I’ve always wanted to build an enduring company. Since leaving college at 19, I’ve built three companies, all with varying levels of failure and success. Each one taught me something. Each one demanded a piece of me.

Now, I’m on my fourth rodeo.

I recently quit my safe, comfortable job to jump back into the ring. To focus. To build again, from the ground up.

Am I certain of a glorious outcome? Not at all. But I am more equipped than ever before. Time will tell the rest.

What I am certain of is that this is the only path. You can’t phone it in. You can’t do it as a side project. It requires your full attention. It requires courage.

Whatever is worth doing is worth doing well. And to get outlier outcomes, you have to take outlier risks. You have to be willing to fail.

You have to put your skin in the game!!.