The first jobs of 11 famous CEOs (that may surprise you)

It’s easy to assume that the billionaire business owners of today have always had a comfortable lifestyle. On the contrary, ascending to such great heights usually doesn’t come without its fair share of hard work—even when said hard work means schlepping newspapers to save for college or working as a dishwasher to fund a startup.

Interestingly enough, the first jobs of some of the most famous CEOs and thought leaders sound pretty similar to our first places of employment—you might be surprised to see that most multi-billionaire business men and women actually started out with very similar humble beginnings.

From Oprah Winfrey’s time as a grocery store clerk to Warren Buffett making his first dollar on the back of his bicycle, here’s what these famous CEOs and founders were up to before they got their big break.

Oprah Winfrey worked at a grocery store

Oprah Winfrey might have a glamorous lifestyle now—but her first job as a teenager was working at her local grocery store.

She didn’t stay there long, though, as at the age of 17 she won the Miss Black Tennessee beauty pageant and was eventually invited to do radio news part time.

Jack Dorsey was a software engineer

Twitter and Square Founder Jack Dorsey quite literally hacked his way into his first job as a software engineer.

According to VentureBeat, Dorsey “really wanted to go into the dispatch industry” so he found a hole in the company’s website, alerted the chairman about it, and subsequently landed his first job as a software engineer back in 1991.

Travis Kalanick sold knives door-to-door

The founder and former CEO of Uber, Travis Kalanick, got his start in the working world as a door-to-door salesman when he was just a teenager.

He peddled knives for Cutco in the nineties—but only until he turned 18. By then, he had already started his first company—an SAT-prep course called New Way Academy.

Steve Jobs developed video games for Atari

It should come as no surprise that Steve Jobs has always had a passion for technology and invention.

In fact, the late founder of Apple was so keen to learn the ins and outs of modern technology that he dropped out of college and became a video game developer at Atari.

He didn’t last too long, though, as he and Steve Wozniak founded Apple Computers a few years later when he was just 21 years old.

Tim Cook delivered newspapers in his hometown

Apple’s current CEO Tim Cook had a slightly more humble beginning to his career—he delivered newspapers in his Alabama hometown, worked at a paper mill in Alabama, and at an aluminum plant in Virginia, all before finally making the move into the technology world in the early eighties.

Elon Musk wrote video game code

Tesla Founder Elon Musk didn’t spend his time flipping burgers or delivering newspapers as some of his contemporaries did as children—instead, he wrote video game code when he was just 12 years of age.

The tech wunderkin was always fascinated by technology and his early obsession earned him $500 for coding a space-themed video game back in 1983.

Jeff Bezos worked as a camp leader

It might be hard to imagine Amazon CEO Jeff Bezos working as a camp leader—but that’s exactly where he got his start. The billionaire entrepreneur created his first job with his former girlfriend while they were in high school.

The “Dream Institute,” according to the Miami Herald, was an educational summer camp for fourth, fifth, and sixth graders. The camp was designed to teach campers all types of tech-adjacent and scientific discoveries, including black holes in space, nuclear war, and more.

Warren Buffett delivered the Omaha World-Herald newspaper

Multi-entrepreneur and investor Warren Buffett has very humble beginnings when it comes to his start in the working world.

The billionaire businessman started out delivering the Omaha World-Heritage newspaper on his bicycle at the tender age of 13. In fact, according to, he had even claimed his bicycle as a deduction on his first tax return.

Michael Dell was a dishwasher

According to, Michael Dell, CEO of Dell Technologies, was an avid stamp collector as a child—and as such needed to pick up a job to fund his growing collection.

When Dell was just 12 years old, he began washing dishes at a local Chinese restaurant and was so good that he was later promoted to busboy!

Doug McMillon was a warehouse worker

Doug McMillon, chief executive officer of Walmart, actually landed his first job at the very company he now oversees—Walmart. McMillon started out working at the Walmart warehouse in Arkansas and never left.

He credits his hard work for what helped him move up such significant ranks.  “If you don’t take care of the basics like showing up on time and striving to exceed the expectations of your leadership, your career doesn’t move,” he once told CNBC in a statement.

Terry Lundgren started out shucking oysters

Terry Lundgren, the CEO of Macy’s, had originally wanted to be a veterinarian but his grades were not up to par with his peers and he ended up switching his major to business.

This didn’t make sense to his father, who ended up cutting him off financially.

Lundgren then got a job at a local restaurant shucking oysters to put himself through college—and eventually became the manager of the restaurant before graduating into retail.