You are probably one of the millions of people who have had a package delivered by FedEx. What you might not know is that Federal Express could have gone bankrupt if it weren’t for a desperate blackjack session. As hard as it might be to believe, the founder of FedEx used blackjack winnings in the early days of the company to keep it afloat. Fred Smith took a winning session at the blackjack tables of Las Vegas and turned FedEx into a multi-billion dollar company.

FedEx Almost Fails

March 29, 2026 · Counting Edge Editorial

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According to Business Insider, Fred Smith was a college student when he got the idea for FedEx. He wrote a paper for his economics class about automated shipping ventures. The paper only received a modest grade, but it birthed the idea for a worldwide shipping company. Smith used a mixture of inheritance money, loans, and investments to get Federal Express off the ground. The total was somewhere in the neighborhood of $84 million. Just two short years later the company was in dire straits.

At one point the company only had $5,000 in operating capital. That wasn’t even enough money to purchase fuel for the company’s planes. Some of the company’s pilots were even maxing out their personal credit cards for fuel, and others were holding their paychecks. This was when Smith made what many would call a rash decision. He took the remaining $5,000 and headed for the blackjack tables in Las Vegas. It was done on impulse.

Even the other company executives didn’t know what Smith was doing. There is no word on whether Smith was an experienced player. For all anyone knows he may have been a relative newcomer to the game. It didn’t matter. Just one week later Smith was back at FedEx headquarters with $27,000. Blackjack had saved FedEx for another week.

Of course, this temporary influx of operating capital courtesy of the blackjack tables in Vegas wasn’t enough to fix the company’s problems. Smith says that winning the money inspired him to renew his efforts to get more funding for the company. He went on to raise another $11 million and the rest, as they say, is history. So, every time that you see a FedEx truck rolling down the highway or a FedEx plane leaving the runway, remember that the game of blackjack helped to keep the company out of bankruptcy. You might not agree with Smith’s decision. His partners certainly did not when he told them about it.

But you must concede that Smith must have had nerves of steel during that week of blackjack in Las Vegas.

Using Blackjack to Raise Capital

This story seems unbelievable. Counting Edge would never advise someone to take the remaining funds needed to sustain their company to a blackjack table. Nor would we recommend an individual using bill money to gamble. Fred Smith’s story, though, is not that uncommon. Other successful businessmen have used blackjack and other forms of gambling to raise money. Bill Gross is the founder of PIMCO.

According to CNN, Gross funded many of his investments with blackjack and gambling. Gross was so talented at blackjack and card counting that he made a living from the game in Las Vegas before he became a big investor. Gross has even said that the lessons he learned playing blackjack have helped him pick stocks. There is no way to tell how many people have used blackjack to pay off debts, make investments, or fund companies.

There is also no way to tell how many people have attempted to do all of these things only to go broke. For every winning story there are probably a hundred losing ones. Yet, do the examples of Smith and Gross prove the point that it is possible to gamble successfully? Is it not foreordained that everyone must lose when playing blackjack? Their successes seem to invalidate the argument that gambling is bad on general principles. The stories at least make a case that a disciplined player can walk away with their winnings and do something good.

Doyle Brunson, the legendary World Series of Poker Champion, hasn’t worked a day of his life since he was very young. This is by his own admission. Brunson can regularly be seen in the biggest poker games in Vegas, sometimes betting into pots that exceed $1 million. He has a nice home in Vegas, paid for with poker money. His family has become wealthy. What did these men have in common that made them successful at gambling?

One answer is surely a large bankroll. Smith bought in with $5,000 when he made his trip to Vegas. Gross has bet thousands on a single hand. The difference between these men and others may be that they can win a substantial sum of money on just one hand. That could work to counteract variance and other factors that cause some players to lose in the long run.

You Don’t Need to Own FedEx to Play Blackjack Online

You don’t have to be rich like Fred Smith or own a big company like FedEx to enjoy blackjack. Just check out some of our recommended online casinos. You can play blackjack and many of its variations for just $1 per hand, and many online casinos will also give you a nice welcome bonus when you make your first deposit. Just remember us at Counting Edge when you win enough to open your own big company!

Variance, desperation, and why this story is not a blueprint

Smith’s $5,000 flyer worked once; repeating it would have been Russian roulette with payroll. Casinos price games so that repeated desperate doubling eventually meets a limit or a cold streak. If you are tempted to “win back” rent, tuition, or float cash, stop and read discipline for online blackjack instead—there is no corporate boardroom miracle tied to the next shoe.

What professional gamblers actually share with founders

Gross and Smith both understood risk budgeting: how much pain they could absorb before folding a venture. That maps to bankroll management and session caps more than to lucky hunches. Founders diversify; gamblers who survive diversify too—by game selection, bet spread, and knowing when to log off.

FAQs: FedEx and the blackjack legend

Did FedEx really survive because of blackjack?

Founder Fred Smith has described using a small remaining cash pool in Las Vegas as a short-term bridge while he secured more funding—think working capital gap, not a business model.

Should I try the same thing with my startup float?

No—treat the story as historical color, not advice; one survivorship tale hides countless busted bankrolls.

What blackjack lesson applies to ordinary players?

Keep gambling money segregated from obligations, size bets to cushion losing streaks, and never confuse a lucky week with skill edge.

Frequently asked questions

Is the FedEx blackjack story verified?

Fred Smith has publicly discussed using remaining cash in Las Vegas as a short-term bridge while raising additional funding; details vary by interview but the core anecdote is widely reported.

Should entrepreneurs gamble with payroll money?

No—Counting Edge treats the FedEx tale as a cautionary curiosity, not a template for financing a business.

What is the real takeaway for blackjack students?

Separate life-stakes money from gambling bankrolls and respect variance even when legends get lucky once.