The First Jobs of Well-Known Billionaires

More than 2,000 billionaires live among us. Here’s how some of them started out.

The First Jobs of Well-Known Billionaires

jobs of billionaires — Oprah Winfrey, shown here in 1985, is among the cohort of billionaires who are completely self-made.

More than 2,000 billionaires now roam the earth, the largest amount ever according to Forbes. They’re richer than ever, too, with an estimated more than $9 trillion in combined worth.

Some inherited their wealth. Others started with nothing and created their own fortunes. Still others took more modest wealth and increased it many times over.

Some billionaires leaned on the knowledge they gained earning their college degree, while others dropped out of school altogether.

In short, there’s no magic formula to becoming a billionaire. But here’s one constant: Each had to start his or her working life somewhere. Here’s a look at some well-known billionaires and their earliest jobs.

Oprah Winfrey

Signature business achievement: Media mogul and entrepreneur

Early work: Oprah worked as a grocery store clerk in Nashville, then at 16 was hired to read the news on a local radio station, WVOL.

The Oprah Winfrey Show, a nationally syndicated talk show, propelled her into the limelight and she leveraged the show’s popularity to gain ownership of the program and start her own production company. She later moved into print media and formed her own network.

In her commencement address to the 2018 graduates of the University of Southern California, Annenberg School for Communication and Journalism, she said, “Every remedial chore, every boss who takes credit for your ideas — that is going to happen — look for the lessons because the lessons are always there. And the number one lesson I can offer you where your work is concerned is this: Become so skilled, so vigilant, so flat-out fantastic at what you do that your talent cannot be dismissed."

Richard Branson

Signature business achievements: Founder, the Voyager Group; Virgin Records; and Virgin Atlantic airlines

Early work: Branson showed an entrepreneurial spirit from a young age. When he was 11, he bred and sold birds and tried his hand at selling Christmas trees. While the bird business went well, rabbits ate the tree seedlings, cutting into his profits.

At 16 he started a student-run magazine focused on youth culture, called Student and sold $8,000 in advertising for the first issue. Within a few years, he began a mail-order record company, Virgin, which made him enough money to build a recording studio and his empire began.

Branson did not do well in school, likely in part due to his dyslexia. In a post on the company’s blog, he advises his teenage self: “You should never see being different as a flaw or think that something is wrong with you. Being different is your biggest asset and will help you succeed.”

Life taught him that frustrations can be turned to positives and that it is okay to not be good at some things. His recommendation: “Find things that interest you and pursue them doggedly. This passion is what will keep you going when things get tough — and life is always full of challenges.”

Li Ka-shing

Signature business achievement: Chairman, CK Hutchison Holdings and CK Asset Holdings

Early work: Li Ka-shing became an apprentice at a watch strap factory at age 13. He worked his way up and became general manager of the factory at 19. At 21, he went on to found Cheung Kong plastics and used the profits to investments in rental properties and factories, using those funds to invest in the market.

Li told Forbes, “The burden of poverty and this bitter taste of helplessness and isolation sort of branded on my heart forever the questions that still drive me. Is it possible to reshape one’s destiny? Is it possible to minimize challenges through lessening complexities? And is it possible to enhance chances for success through meticulous planning?”

Jeff Bezos

Signature business achievement: Founder, Amazon

Early work: Bezos spent summers growing up roaming his grandparents Texas ranch, where he learned to fix tractors, repair windmills and castrate bulls. His introduction to paid employment was much like that of many American teens, working a summer service job, in his case, at McDonald’s. He told Cody Teets, author of “Golden Opportunity: Remarkable Careers That Began at McDonald's,” “You can learn responsibility in any job, if you take it seriously. You learn a lot as a teenager working at McDonald's. It's different from what you learn in school. Don't underestimate the value of that!”

The following summer, he started his first business. The Dream Institute was an educational summer camp for grades 4 to 6 that blended science and literature. Of the six campers who signed up, two were his siblings. After college and several years in the workforce, Bezos decided to sell books online and he left a comfortable Wall Street VP position to move across the country and strike out on his own. Amazon was born.

Warren Buffett

Signature business achievement: Chairman and CEO, Berkshire Hathaway

Early work: Buffett’s childhood included a series of business ventures. At age 6, he sold packs of gum and Coca-Cola door-to-door. He made his first investment (in an oil services company) at age 11. The stock plummeted, but rebounded, enabling him to sell for a modest profit, before the stock then soared in value, teaching him the importance of timing in investing.

At 13, while his father was a Nebraska Congressman, he was a paperboy, for The Washington Post. He also sold magazine subscriptions and calendars, netting $2,000 in two years. He invested some of it in a Nebraska farm. He also started several of his own businesses: selling used golf balls, collectible stamp sales and Buffett’s Showroom Shine (a short-lived car-shining business) and a pinball business. After college, Buffett worked as a stockbroker before starting his own company.

Kevin Plank

Signature business achievement: Founder, Under Armour

Early work: At age ten, Plank mowed lawns and shoveled snow. At age 14, he sold knit bracelets at Grateful Dead concerts. At 19, he moved on to T-shirt sales. He created Under Armour to solve what he perceived as a problem. Believing that sweat-wicking undergarments would improve athlete performance and comfort, he designed a shirt and starting selling them from his grandmother’s basement.

He told CNBC: “There’s the old slogan from salespeople where they say, salesmen are not made, they’re born. I’m not sure that entrepreneurs are much different. It’s a fire that you have when school gets canceled and you're a ten year old kid, you're jumping up and down because you say I got to wake up at 6:30 and go shovel snow all morning and make a pocket full of cash. That’s the attitude I think all of us should have. Is that I’m not a big believer in sleep. I believe in energy, I believe in getting out, waking up, attacking the day. And I think that comes through with the culture of our business and our company as well.”

Michael Dell

Signature business achievement: Founder, Dell Technologies

Early work: At age 12, Dell ran a successful mail-order business selling baseball cards and stamps. In high school he got a job as a paperboy for the Houston Post, where he brainstormed new ideas to get sales. He compiled mailing lists of newlyweds and families new to the neighborhood and offered them special deals. One year these methods earned him $18,000.

Though he started college as a pre-med student (as his parents wanted him to), he spent his spare time buying, upgrading and re-selling old PCs. After brokering a deal with his parents to return to school if his new business plan failed, he started a business and sold $180,000 during his first month. Perfecting his “direct model of selling,” he brought in $6 million his first year. His hands-on approach has kept Dell Computer competitive in the PC market.

Charles Schwab

Signature business achievement: Founder, Charles Schwab & Co.

Early work: Charles Schwab grew up in post World War II farmland in California and made money selling magazine subscriptions, bagging walnuts, caddying and doing other assorted jobs. At age 12, he got into the chicken business. According to CNN Money, he’s joked that “the chicken business was my first fully integrated venture. Obviously, selling the eggs was very important. I also realized that a lot of women back then — this was 1949, 1950 — needed fertilizer for their gardens. The chicken droppings were very well received for that, and of course at the end of the poor chicken's life cycle, you could sell it as a nice fryer. So I just put it all together, selling everything except the feathers.”

The money he earned, he told CNN Money, went to family expenses, teaching him “you have to save the money before you have it to invest. I learned the first part of economic principles: Saving has to come before investing.” He added that his dyslexia was “fuel for motivation. It’s helped me accomplish some things that I wouldn't have believed possible for me to do.”

Schwab started as a securities analyst before starting his own investment advisory company. Seeing an untapped market, Schwab targeted small investors, offering basic service and discounts as low as half that of his competitors. He was among the first to automate order processing, thereby cutting his costs. He also branched out to other investment services. Only 10 years after opening his first office he had branches in 40 cities.

Elon Musk

Signature business achievements: Co-founder, PayPal; founder, Tesla Motors and SpaceX

Early work: At age 10, Musk taught himself to code on a Commodore VIC-20. When he was 12, he created a Space Invaders-style game called Blastar and sold the code to PC and Office Technology for $500.

He abandoned thoughts of earning a PhD to start his first company, Zip2 Corporation, which he sold to Compaq Computers. He then co-founded an online financial services company, X.com, (this became PayPal) and sold that to eBay. Not done innovating, he also formed the spacecraft company SpaceX, co-found Tesla Motors and acquired SolarCity, all while working on other projects in transportation and artificial intelligence.

Bruce Nordstrom

Signature business achievement: Chairman, Nordstrom

Early work: Nordstrom’s dad gave him his first job — at the bottom of the family business. At 9, he was a shoe stockroom clerk; by age 14 he had worked his way up to shoe salesman. Sixteen years later, he was president of the company and his decisions led the retailer to become a top U.S. retailer.

Nordstrom claims that at Nordstrom’s Department Stores, the employees’ original training came from their parents, not the Nordstrom’s sales training program. He is known for saying: ‘‘We can hire nice people and teach them to sell, but we can’t hire salespeople and teach them to be nice.’’

Leonardo Del Vecchio

Signature business achievement: Founder, Luxottica (parent company of Sunglass Hut, LensCrafters, Ray-Ban and Oakley, and supplier to other eyewear companies)

Early work: After the death of his father, Del Vecchio’s mother was unable to support the family so he grew up in an orphanage. When he was 14, he apprenticed at a tool factory that made auto and eyewear parts, where he learned skills that would seal his fortune.

In his early 20s, he opened his own workshop to manufacture tools and eyewear parts in Milan. Within a decade, had moved the factory to Agordo, Italy, and was making his own brand of eyeglass frames. The company further expanded through acquisition and now has six factories and makes 65,000 pairs of glasses a day.

Steve Cohen

Signature business achievement: Wall Street hedge fund manager

Early work: As a teen, Cohen worked in the produce section of Bohack supermarket, but quit when he realized he was making more money playing poker. Aside from the financial benefit, he was drawn by the game itself, which required him to weigh the risks and probabilities.

“I’ve always been de-sensitized to money,” he told Vanity Fair. “It was just always there. I didn’t think about it.” He told an audience at an investment conference that his love of trading started in high school. Even then, he said, he was reading stock tables in the newspaper and watching the stock ticker scroll by at a local brokerage firm.

“It’s the same with trading,” he said to Vanity Fair. “I think about the risk. I think about the trade. I don’t think about the money.” In college, he got the attention of brokers while standing outside a Merrill Lynch office in Philadelphia, watching the New York Stock Exchange data scroll by. He started investing his poker winnings, using his intuition as a guide. He worked as a trader for about a decade before starting his own successful trading company.

Sheldon Adelson

Signature business achievement: CEO and chairman, Las Vegas Sands

Early work: At age 12, Adelson sold newspapers and toiletries. At 16, he owned 125 candy vending machines. He joined the Army and worked as a court stenographer on Wall Street, then made his fortune as a mortgage broker and investment adviser.

After buying a computer magazine, he decided to start a trade show for the industry. The initial Computer Dealers Expo (COMDEX) coincided with the rise of the computer industry and quickly became the largest trade show in Las Vegas before expanding to other countries. A decade later, Adelson purchased the Sands Casino.

Bill Gates

Signature business achievement: Founder, Microsoft

Early work: Gates’s first job was as a page in Congress (which he says “isn’t a real job”). When he was a senior in high school, he worked as a programmer for Bonneville Power Administration.

At 15, he and another student, Paul Allen created Traf-O-Data, a program that measured traffic flow in the Seattle area. From there, Gates and Allen started Microsoft and made their name developing OS-DOS, which they licensed to IBM. The decision to license rather than sell helped to make Microsoft a household name.

Evan Spiegel

Signature business achievement: Founder, Snapchat

Early work: Spiegel story isn’t a rags-to-riches one. "I am a young, white, educated male," he once said at a Stanford business conference. "I got really, really lucky. And life isn't fair." In high school, he had a marketing internship with Red Bull which entailed planning promotional parties. In college, Spiegel studied product design and worked on several software projects before a casual conversation prompted him and his partners to create Picaboo, the app that would ultimately become Snapchat.

Mark Cuban

Signature business achievements: Founder, Broadcast.com; owner Dallas Mavericks; and “Shark Tank” investor

Early work: At age 12, Cuban’s father wouldn’t give him money for a pair of shoes he wanted, so he became a door-to-door garbage bag salesman to raise the money he needed. In high school, he sold stamps and coins.

After a difference of opinion with an employer, he set out on his own, creating a computer consulting service that he later sold to CompuServe. Five years later, he co-founded a company to stream audio, selling that after four years for $5.6 billion. Today, the Dallas Mavericks basketball team is only one of many businesses in his portfolio.

“Starting a business as a child can impact the rest of your life,” Cuban told HuffPost. “It teaches them how business works. It teaches them that they can accomplish goals they set for themselves. All of which will benefit them later on.”

For more about Mark Cuban, check out our View From the Top career deep dive.