How FedEx’s Founder Gambled It All—and Won

In honor of Frederick W. Smith

At some point, every entrepreneur hits a wall. For Frederick W. Smith, the founder of FedEx, that wall wasn’t theoretical—it was financial, absolute, and looming.

It was 1973. The idea was revolutionary: create an overnight delivery system that operated independently from the U.S. Postal Service. Smith had written about it in a term paper at Yale, and now he was trying to turn it into reality. But his startup, then called Federal Express, was burning through cash. Planes needed fuel. Employees needed paychecks. And the dream? The dream needed belief.

But belief doesn’t buy jet fuel.

Down to his last $5,000, Smith did what no MBA program would ever recommend—he flew to Las Vegas and gambled the company’s remaining funds at the blackjack table.

It wasn’t a strategy. It was survival.

He walked away with $27,000. Enough to refuel the planes and keep the business alive—at least for another week. That single act didn’t make FedEx profitable overnight, but it bought them just enough time to turn things around.

And that’s the lesson: when most people would’ve folded, Smith figured it out.

Today, FedEx is one of the largest logistics companies in the world. But it started with one man, one vision, and one desperate night in Vegas.

At FigureItOutNation, we celebrate the stories that define grit. We believe in honoring the individuals who didn’t quit, who didn’t ask for permission, who didn’t wait for someone else to save them.

Frederick W. Smith didn’t just build a shipping empire.He showed the world what it looks like when someone truly figures it out.

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