Where Millionaires Like Oprah and Mark Cuban Were in Their 20s

©Roger Askew/The Oxford Union/REX/Shutterstock

©Roger Askew/The Oxford Union/REX/Shutterstock

Many wealthy people can trace their successful beginnings to their 20s. After all, your 20s are typically the time when you’ll experience exciting life changes, such as graduating from college, getting your first job and living on your own. But, it’s also the age where you’ll learn hard lessons, including how to deal with rejection or how to survive on a small paycheck.

If you’re a millennial, these success stories might inspire you. From Oprah Winfrey to Mark Cuban, these millionaires — and billionaires — weren’t quite as big and successful in their 20s. In fact, some of their early days are not what you’d expect.

Click through to get expert tips on how to manage your money better no matter your age.


Bill Gates: Cobbled Together Software for Hardware He’d Never Seen

Every young entrepreneur needs someone to take a chance on them, but that chance must be earned. Work hard to create something of value, so when an opportunity presents itself, you can bring something to the table that makes you indispensable. That’s one of the ways Bill Gates built his fortune.

In 1974, Harvard student Gates read an article in Popular Electronics about a new computer made by a company in New Mexico. Gates and fellow Microsoft co-founder Paul Allen contacted the company and claimed to have developed a BASIC language interpreter designed for the computer, reported BBC.

When the company agreed to take a look, Gates and Allen scrambled to get the program ready. When their version of BASIC was demonstrated for the first time in Albuquerque, it worked successfully. Soon after, both Allen and Gates were hired and headed to New Mexico.

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Mark Cuban: Got Fired and Inspired to Be His Own Boss

To be a successful billionaire entrepreneur like Mark Cuban, you might want to follow his example. Cuban learned a life lesson at 25 that made him fully commit to starting his own business.

When a boss told Cuban not to chase a sale, he did it anyway. The boss fired him on the spot for disobeying — even though Cuban would have earned the company $15,000.

“[B]eing fired from that job was the determining factor in my business life,” Cuban wrote in an article for Forbes in 2013. “I decided then and there to start my own company. I didn’t have that much to lose, and it was something that I knew I had to do.”

Ever since, Cuban has spent his life trying to do the opposite of everything that boss represented, making the boss a kind of reverse mentor. In fact, Cuban shuns the title of “CEO.”

Today, the millennials who follow their instincts, take chances and stick to their beliefs will likely be the ones who go the furthest.

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Richard Branson: Launched a Mail-Order Record Startup

Virgin Group founder and billionaire Sir Richard Branson struggled throughout his schooling and skipped college. Instead, Branson followed his entrepreneurial instinct and started selling records by mail order in 1970, reports the Independent. He started a mail-order business, and it soon parlayed into a record shop, then a studio and eventually a record label that signed acts like the Sex Pistols.

Virgin is now one of the most high-profile companies in the world, with dozens of branded companies. It all started because Branson identified a problem in the market — high record costs — and positioned himself as the solution.

The takeaway? Look for things that bug you about an industry you love, come up with a solution and work hard until the money rolls in.


Sam Walton: Worked as a Retail Management Trainee

When Walmart founder Sam Walton died in 1992, his namesake store was the giant of the American retail landscape. But Walton’s customer-first focus started early with his 1940 job at JCPenney as a 20-something management trainee.

“There is only one boss — the customer,” Walton reportedly said. “And he can fire everybody in the company from the chairman on down, simply by spending his money somewhere else.”

If you’re thinking about one day starting a business, always remain humble and take care of your customers and supporters — whether you’re a management trainee or the CEO. Without them, even the biggest and strongest companies can fall.

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Steve Jobs: Founded Apple Out of His Parents’ Garage

The late Steve Jobs was arguably the most important inventor and executive to emerge from the modern tech revolution — and certainly one of the most prominent. But in 1976, Jobs was just a young college dropout messing around with new technology in his family’s garage with Apple co-founder Steve Wozniak.

Today, Apple is one of the most valuable brands in the world and currently pacing to be the first U.S. company to hit $1 trillion in market value. And it all started with Jobs as a curious young man.

No one learns it all in college — or outside of college — and young people should consider themselves sponges who are just beginning their real education. Surround yourself with people who share your passions, and make sure those people are more experienced than you, more advanced than you and more knowledgeable than you. You can’t learn if you’re the smartest person in the room.


Oprah Winfrey: Got Demoted, but Stayed Open to New Opportunities

In her early 20s, Oprah Winfrey was hired to be a co-anchor at a Baltimore news station — a huge accomplishment for someone so young. But after several months, Winfrey was demoted.

“I shall never forget April 1, 1977,” Winfrey said in an interview with Baltimore magazine. “I got called out of the newsroom to meet with the general manager. … I was devastated. I knew it was a horrible demotion.”

Soon, another opportunity came up to co-host a talk show. Winfrey initially resisted the idea but decided to try it. “From that first day, I knew instantly this is what I was supposed to do,” she told the magazine. “I felt like I had come home to myself.”

Like Winfrey, 20-somethings shouldn’t give up if they encounter setbacks in their careers. Sometimes, what might seem like a failure is actually an opportunity to achieve greatness.

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Kanye West: Survived a Devastating Car Accident

In October 2002, rap superstar Kanye West sustained injuries from a car accident. After the accident, he told MTV, “My jaw was broken in three places. I had nasal fractures — I’d be talking to people and my nose would start bleeding.”

West recorded his song “Through the Wire” with his jaw wired shut, reports Rolling Stone.

Every 20-something should remember that the future belongs to them — but they need to give it their all in the here and now, too.


Eminem: Released an Unsuccessful Album Before Getting Picked Up by Dr. Dre

Marshall Mathers — also known by his stage name Eminem — came from a broken home and endured bullying. But, Mathers found a passion for words and rapping, and verbally sparred in the fiercely competitive Detroit rap battle scene. Even so, he failed to reach stardom with his first solo album, “Infinite.”

Eminem kept at it, though, and his “Slim Shady EP” landed with Dr. Dre, a rap legend and super producer. Dr. Dre listened to the EP, recognized Eminem’s impressive talent right away and signed him. Eminem went on to become one of the most critically acclaimed and commercially successful rappers of all time.

Through years of adversity, the only thing Eminem really had turned out to be the only thing he needed: persistence. When they’re ready to give up, millennials can look to Eminem as an example of what can be achieved if they keep at it.


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Madonna: Took Odd Jobs to Pursue Singing

Pop superstar Madonna moved to New York to become a “real artist,” she wrote in Harper’s Bazaar in 2013. But before she became known as a “Material Girl,” Madonna worked odd jobs in the city to support herself.

“Trying to be a professional dancer, paying my rent by posing nude for art classes, staring at people staring at me naked,” Madonna wrote in the piece for Harper’s Bazaar. “Daring them to think of me as anything but a form they were trying to capture with their pencils and charcoal. I was defiant. Hell-bent on surviving. On making it.”

But eventually, her hustling paid off. By the early ’80s, she recorded and released her self-titled debut album — and the rest is pop music history.

No matter what the industry or the circumstance, there will never be a substitute for hard work and discipline. These are the traits that are essential to succeeding in any pursuit.

Taylor Bell contributed to the reporting for this article.

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