9 Incredibly Successful Entrepreneurs Who All Failed Big Before Winning Big
Failure: a hallmark of all great entrepreneurs.
If you’re an entrepreneur, you’ve no doubt had to experience your own fair share of failure. Maybe you’ve even questioned your path or ability to be successful.
That’s when the stories of incredibly successful entrepreneurs, and their equally incredible failures, can be a welcomed reminder that you’re not so far off; that you’re on the right track and have the potential to make your dreams happen.
I have not failed. I've just found 10,000 ways that won't work.
But failure isn't easy. If you’ve experienced it, you know how quickly it can turn you away from your dream, causing you to cower in fear and settle for less.
But you’re not that kind of person, are you? You’re an entrepreneur. And entrepreneurship is also synonymous with another word: fighter.
I hope these stories of incredibly successful business leaders who all failed big before winning big inspire you to pursue your dream harder than ever:
1. Mark Cuban
Mark Cuban is easily one of the most well-known entrepreneurs of the 21st century. He became a household name for owning the NBA’s Dallas Mavericks and being one of the original sharks on the hit show Shark Tank.
Mark’s wealth is estimated to be $3.3 billion, but it took him a lot of trial and error to become the outspoken, wealthy tech investor he is now. His first failed business venture? Powdered milk. And, despite his belief that the business would be a hit, his parents were his only customers.
2. James Dyson
James Dyson (yes, as in the Dyson vacuum cleaner), wasn’t always known as the inventor of a wildly successful home product.
Before Dyson became a household name, it took him fifteen years and over five thousand (yes, five thousand) failed prototypes to create the world’s first bagless vacuum.
Now, Dyson creates everything from vacuums to hand dryers (their units occupy many public restrooms), heaters, and those trippy fans that look like big spheres with nothing inside. His company is now working on an electric car prototype, but that never would have been possible without those first five thousand failures.
3. Vera Wang
Vera Wang is one of the most famous fashion designers on the planet -- but it wasn’t always that way.
Wang actually started her professional career as a figure skater hoping to make it to the Olympics. However, she failed to make team USA and her professional skating aspirations were crushed.
Having moved on from figure skating, she worked at Vogue. But she was turned down for the position of editor-in-chief, as she wasn't believed to be a good fit for the role. That didn't stop her either.
Wang stayed in the fashion industry, but she went on to create one of the most well-known bridal brands in history.
4. Milton Hershey
Recognize the last name? Who doesn’t know Hershey’s chocolate? Now found on the shelves of virtually every major grocery store and market in the U.S., Hershey’s wasn't always a beloved American brand.
Before Hershey founded Lancaster Caramel and Hershey's, he tried to start three separate candy companies, all of which failed horribly. Let that sit in the next time you eat a chocolate bar.
5. Arianna Huffington
Arianna Huffington's success story is a bit more recent than the ones mentioned above, but her name is as powerful. The media mogul founded one of the largest digital news outlet of our times, The Huffington Post, and revolutionized the media landscape and the journalistic business model in the process.
That successful venture brought Huffington roughly three-hundred million dollars when The Huffington Post was sold to AOL in 2011. However, before creating The Huffington Post, her second book was rejected by thirty-six publishers. Seeing a pattern yet?
6. Peter Thiel
Peter Thiel, billionaire investor and venture capitalist, was one of the founders of PayPal before becoming the first outside investor of a little company called Facebook -- he acquired a 10.2% stake in the company, which he later sold for more than one billion dollars. Thiel has gone on to co-found several other startups, including Valar Ventures and Mithril Capital.
But Thiel failed about as big as anyone could ever fail. Clarium Capital, an early hedge fund he co-founded, lost ninety percent of its $7 billion dollars in assets.
7. Walt Disney
The name Walt Disney conjures more than just ideas of a successful entrepreneur, it brings countless images of stories and beloved characters who are deeply connected to American culture -- and even the world.
However, would you believe that Disney was fired by his newspaper editor for apparently “not having good ideas or any imagination?" That’s right, his newspaper editor didn’t even believe he had enough imagination to be a local writer.
Walt Disney Co. is currently valued at about $160 billion dollars. How's that for proving people wrong?
8. Thomas Edison
The classic example of reaching success after going through failure, Thomas Edison tried to invent the light bulb more than ten-thousand timesbefore succeeding.
Edison would go on to nab contracts to power electricity through many of the largest counties of the United States, becoming one of the most successful entrepreneurs of his time.
9. Steve Jobs
This list would not be complete without Steve Jobs.
Given his success during the latter part of his life, it's easy to forget he was actually fired from Apple in 1985.
Ironically enough, he credited some of his biggest wins to that experience:
“I didn’t see it then, but it turned out that getting fired from Apple was the best thing that could have ever happened to me. The heaviness of being successful was replaced by the lightness of being a beginner again, less sure about everything. It freed me to enter one of the most creative periods of my life.”
Military Dad Defends His 4 Little Daughters When Strangers Make This Rude Remark
Military Dad of 4 Daughters Defends His Girls When Strangers Make This Rude Remark
Austin von Letkemann is the military officer strangers feel "sorry" for — and the reason is infuriating.
Whenever the devoted father leaves the house with his four children, strangers can't help but notice the officer in uniform is holding hands with 4 adorable little girls. They will tell the traditionally "masculine" and "all American" dad they feel sorry for him, because he has no sons. This dad makes one thing very clear: They are his daughters, they aren't a burden.
In a passionate video, von Letkemann took to Instagram to share with his followers that the only thing that's "difficult" about being a girl dad — is clapping back to these sexist remarks over and over again.
They Mock His Daughters To Their Face
When strangers approach Austin von Letkemann and his four daughters, they don't always realize that their comments are being overheard. They seem oblivious to the fact that his girls understand every word. Von Letkemann describes how people will approach him and, without thinking, make remarks like "I'm sorry" or even joke about his lack of sons. What they don't realize is that these comments, intended to be light-hearted or humorous, can be deeply hurtful to his daughters. These strangers are not just disrespecting von Letkemann's choices as a father; they're also sending a message to his daughters that their presence is something to be pitied. It’s a message that von Letkemann won't stand for, and he's speaking out to defend his girls from these insensitive remarksSaying "Get Your Shotgun" Isn't Funny — It's Sexist
Another common comment that Austin von Letkemann encounters is the old "better get your shotgun ready" trope, often delivered with a smirk or a wink. This line is typically intended to suggest that a father with daughters should be on high alert to protect them from potential "suitors," implying that they are objects to be guarded rather than individuals with agency.
Von Letkemann finds this line of thinking outdated and sexist. In his viral Instagram video, he points out that these jokes are not just stale — they're damaging.
By suggesting that his daughters require armed protection, the joke reinforces the idea that women are inherently vulnerable and need to be shielded from men. Von Letkemann argues that instead of promoting this narrative, society should focus on teaching respect and consent, challenging these sexist tropes at their source.
Watch Austin von Letkemann's Video:
"If I Had A Fifth Child, I'd HOPE It Was A Girl" — One Dad's Message For Other Parents
Despite the constant remarks about his lack of sons, Austin von Letkemann is clear: He wouldn't trade his daughters for anything.
In fact, he told his Instagram followers that if he were to have a fifth child, he would hope for another girl. This declaration isn't just about doubling down on his pride in his family — it's a pointed response to those who see fathering daughters as a misfortune.
Von Letkemann's stance is a powerful one, rejecting the notion that a family is incomplete without sons. He encourages others to question the assumptions behind these comments and to appreciate the joy and fulfillment that his daughters bring. By sharing his story, von Letkemann hopes to create a more inclusive perspective on fatherhood, one that values daughters just as much as sons.