From Rags to Riches: A List of Successful Entrepreneurs who Overcame Adversity

For those that have tried to start their own business without any help or outside investment, you will know the amount of time and effort it takes to build a successful company from the ground up. Maintaining the unwavering dedication to succeed is a daily challenge—especially while managing other areas of your life.

We are very used to seeing and reading about famous entrepreneurs who consistently move on from one profitable business venture to another, almost as if it’s easy. But in reality business is hard, and the troubling times at the beginning of entrepreneurship are often overlooked.

Here are some success stories from business people who didn’t let utterly dismal circumstances or crushing failures derail their bumpy ride to success:

Sophia Amoruso: From dumpster diver to CEO of a million dollar company

Sohpia Amoruso
photo credit: Wikipedia

Dropping out of school, chasing a job simply because it provides free health care to cover medical bills for a hernia, and living off money earned from selling stolen goods via eBay—Sophia Amoruso’s path to success was anything but conventional (and it certainly wasn’t glamorous).

Amoruso admitted her items had been stolen and was fined by loss-prevention, but she continued selling through eBay until she was finally banned for breaching their policies. This prompted Amoruso to launch her own website “Nasty Gal,” named after a Betty Davis album, which soared to popularity at in incredible pace thanks to a strong following of young women on social media.

Nasty Gal has gone on to generate millions of dollars with its fashionable range of clothing and shoes enjoyed by 550,000 customers across 60 countries.

Jay Z: From the mean streets, to rap icon, and multiple business owner

Jay Z
photo credit: Flickr

You may not automatically think of Jay Z as a businessman, due to his high-profile celebrity status, but there is much more to Jay Z’s successes—being one of the best-selling artists of all time is just one of them. He is the owner of the 40/40 club, the founder of Roc Nation, a certified NBA and MLB sports agent, and if that wasn’t enough—he also owns Tidal, the online music streaming service.

However, Shawn Carter certainly didn’t have an easy start.

He was raised in a housing project in Brooklyn, New York, made his money by selling drugs, and claims he was shot at in his youth. Even during his worst moments, Jay Z kept following his passion for music, which eventually got him out of dire circumstances and propelled him forward to flex his entrepreneurial muscles, and to cement his place as one of the most influential rappers of all time.

Oprah Winfrey: From fired to inspired

Oprah Winfrey
photo credit: Flickr

Oprah Winfrey’s story is a heart-wrenching series of deeply traumatic events, including sexual abuse, running away from home aged 14, and a son born prematurely—who passed away shortly after birth. She was also fired from a news anchor position, ironically told that she “wasn’t fit for television.” Well… Oprah returned to the screen as the host of her own talk show, which ran from 1986 to 2011—making it one of the longest-running and most successful daytime television talk shows in history. She has also appeared in many films and co-authored five books.

Tony Robbins: From a broken home to sell-out shows across the globe

Anthony Robbins
photo credit: Flickr

This walking, talking beacon of positivity endured a rough childhood. His mother abused alcohol and prescription drugs and his father abandoned home entirely. Then, during high school, Robbins was deeply concerned about his health as he shot up in height from 5’1 to 5’11 in just one year. The alarming growth spurt was eventually explained as Robbins was diagnosed with acromegaly.

His difficult years were key ingredients to his success, and Robbins became a best-selling author, life performance coach, and a motivational speaker. A large part of Robbins’ message is to never let traumatic events define us. He’s used his story to help millions live a happier future, regardless of their past.

Henry Ford: From a failed automobile investment to revolutionizing the entire industry

Henry Ford

The world-renowned industrialist Henry Ford ate up his first investment without actually producing a vehicle. There were far more failures than successes in the earlier stages of his career. Ford also tried launching his career in politics—as it wasn’t happening for him in the automobile industry—but he failed at that, too.

He kept pushing through and eventually his efforts were rewarded in an astronomical fashion. He revolutionized transport for the 20th century by making cars affordable to families with average incomes. Ford died in 1947 but his legacy lives on, with Ford Motors still going strong to this day.


All of the above are super successful, each with their own unique route, and none of it came easy—to say the least! While the occasional pitfalls seem inevitable in business, there are plenty of great books written by people who’ve learned some lessons the hard way—so you can avoid making some of their mistakes.