Success stories are wonderful, but failure stories that turn into empires? They’re the stuff of legend. While the glamorous aspect of entrepreneurship gets press—unicorn status, billion-dollar valuations, global reach—the road that gets you there is generally paved with setbacks, rejection, and costly missteps.
What sets successful entrepreneurs apart from everyone else is not an infallible start, but the ability to stand up again after falling down. Here are some of the most motivating stories of entrepreneurs who failed at first—and then went on to build the world’s biggest brands and companies.
1. Steve Jobs: From Apple Outcast to Industry Icon
Steve Jobs is a name that is forever synonymous with innovation, but even fewer remember that he himself was once fired from Apple, the company he co-founded. Internal strife and disagreements with the board led to his dismissal in 1985. It was a public and humiliating loss.
Instead of taking a step back, Jobs founded NeXT, a computer platform company, and purchased what would be Pixar. Apple acquired NeXT in 1997 in a surprise move, and Jobs re-joined the company. He went on to unveil revolutionary products like the iMac, iPod, iPhone, and iPad. Apple became the first trillion-dollar company, and a lot of that transformation can be traced to Jobs’ return.
I didn’t realize at the time, but being fired from Apple was the best thing that could have happened to me.” — Steve Jobs
2. Oprah Winfrey: Fired for Being Too Emotionally Expressive
Before she was one of the most influential media moguls in history, Oprah Winfrey was fired from her job as a news anchor for Baltimore. She was considered too emotional and not appropriate for TV reporting.
But what others perceived as her weakness, Oprah converted into strength. Her innate empathy, accessibility, and her deep understanding of people were the foundation of The Oprah Winfrey Show, which was on air for 25 years. She established Harpo Productions, started OWN (Oprah Winfrey Network), and became the first Black female billionaire in America.
Her failure wasn’t a defect—it was an indication that she was destined for something other, and something greater.
3. Elon Musk: On the Brink of Bankruptcy
We now link the name Elon Musk with Tesla, SpaceX, and Neuralink. Tesla and SpaceX were on the brink of bankruptcy in the early 2000s, though. Musk supported his ventures with his own money even when they went bankrupt one by one.
SpaceX’s first three rocket launches spectacularly failed, and the fourth was do-or-die. Fortunately, it succeeded, and it won them a contract with NASA. Tesla also teetered on the edge of bankruptcy until it finally took off in the electric car market.
Despite ridicule and financial devastation, Musk persevered and transformed near-failure into market supremacy.
4. Walt Disney: Informed He “Lacked Imagination”
It is hard to imagine today’s entertainment industry without Disney, but Walt Disney’s business career began with disappointments. He was actually once fired from a job at a newspaper company for not being “imaginative and for having no good ideas.” His first animation company, Laugh-O-Gram, went out of business.
But Disney did not give up. He simply kept making things, and eventually, he created Mickey Mouse. Folks said a talking cartoon character would never catch on—yet today, Mickey is a global icon. Disney kept building an entertainment empire of movies, merchandise, TV stations, and theme parks all over the globe.
5. Colonel Harland Sanders: 1,000 Times Rejected
Colonel Harland Sanders is arguably one of the most well-known stories of achievement that occurred late in life. He was 65 years old and had been rejected over 1,000 times for allowing restaurants to use his fried chicken recipe when he finally received a “yes.”.
With that one chance, he began franchising Kentucky Fried Chicken. He had sold the business for $2 million (over $17 million in today’s money) when he was 73 years old, and KFC was a worldwide brand with thousands of restaurants across the globe.
His youth and initial failures did not discourage him—rather, they fueled him.
6. Arianna Huffington: Dozens of Rejections to Media Success
Arianna Huffington herself was turned down prior to beginning The Huffington Post. She had her second book turned down by 36 publishers, and when she began her media business, it was turned down as merely a blog.
But she didn’t give up. The Huffington Post became a top news and opinion site, with Thompson eventually selling it for over $300 million to AOL. She then founded Thrive Global, which focuses on workplace culture and well-being.
“Failure is not the opposite of success; it’s a stepping stone to success.” — Arianna Huffington
What Can We Learn from Their Failures?
The setbacks these entrepreneurs faced were not trivial—those setbacks were public, embarrassing, and in some instances, financially crippling. Instead of quitting, however, what they did was different: they reflected, they learned, and they progressed.
The following are important takeaways:
Failure is a lesson and not a sentence. Every rejection, every error, had information that informed the development of wiser strategies and greater determination.
Timing is not everything—stick-to-it-ness is. Some achieved in their 20s, others in their 60s. What it boiled down to was that they didn’t give up. The power lies in your response. Whether it is a job loss or a failed product, the response to failure will write the next chapter. Conclusion: Embrace the Fall, Build the Rise. Success is not a straight line—it zigzags through failure, self-doubt, and setbacks. Jobs, Oprah, Musk, Disney, and other stories remind us that failure is not the end but a detour—a tough but necessary part of the path to greatness. So if you’re at the moment in your own failure, keep hope alive. You may be laying the first bricks of your empire.