Entrepreneurs Who Failed on Their Road to Success

  1. Soichiro Honda
  2. Milton Hershey
  3. Ikutaro Kakehashi
  4. Brian Chesky
  5. David Barnett
  6. Elon Musk
  7. James Dyson
  8. J.K. Rowling

Let’s face it, mistakes happen. When they do occur, it’s important to learn from them. I know that sounds cliché, but there’s some truth behind this statement. In fact, studies continually show making mistakes is essential in the learning process. It helps you notice common errors, how to avoid them, and how to succeed.

Almost every successful entrepreneur has failed at least once. Whether it’s being rejected by an established business, messing up prototypes, dropping out of school, being fired from a job, or going bankrupt, they have stumbled on their way to success.

Michael Jordan became one of the greatest basketball players after being cut from his high school basketball team. Walt Disney lost rights to his first successful cartoon, Oswald the Rabbit, because of a faulty contract. Some of the most amazing entrepreneurs out there have hit road bumps on their path, but they ultimately succeed with grit and perseverance.

1. Soichiro Honda

Source: https://www.rafaeldaluz.com

From the moment Honda saw his first vehicle, he knew he wanted nothing more than to work in the automotive industry. At 15, he left school to become an apprentice at Art Shokai, an auto repair shop in Tokyo. He went on to open his own branch of Art Shokai in Hamamatsu 8 years later. While working at Art Shokai, Soichiro Honda created automotive parts in 1936 for Toyota, but they were rejected.

However, Honda didn’t let Toyota’s rejection get the best of him. When gasoline became scarce shortly after World War II, Honda offered a solution. He created a small 2-stroke motor that needed very little gas to operate and was designed for people to attach to their bicycles. The Honda Motor Company was founded shortly after and released its first motorized bike in 1949. Twenty years later, they began manufacturing cars and have since won countless awards for Best Car of the Year, Top Safety Pick, and Best Value.

Approximate Net Worth of Honda: $58.9 Billion

“Success is 99% failure.” – Soichiro Honda

2. Milton Hershey

Hershey Chocolate

Milton Hershey could never stay in one place for very long because his father was constantly starting new jobs. He had attended 6 different schools by the time he was 13 and dropped out to learn a trade. Two years later he accepted an apprenticeship with a candy maker. This sparked his love for making candy and led him to open a candy shop in the heart of Philadelphia, which never profited. Years later he tried again, in New York City, but it also failed due to lack of finances.

Rather than give up on his dreams, Hershey tried once again to start a candy business, except this time he would only sell caramels. His caramel shop was a huge success! After opening shops all over the country, Hershey sold his caramel business for $1 million in 1900. 5 years later, the first Hershey Company factory opened for business. Since the factory was in the middle of nowhere, Hershey bought the land and built an entire community around his factory, now known as Hershey, Pennsylvania. This tourist destination includes a Hershey theme park, Founder’s Hall at the Milton Hershey School, Hershey Theatre, and so much more.

Today, you enjoy the delicious chocolate produced by Hershey like their chocolate bars and iconic Hershey Kisses. The brand also produces other favorite treats like Almond Joy, Cadbury, Reese, and Twizzlers.

Approximate Net Worth of The Hershey Company: $18.8 Billion

“Give them quality. That’s the best kind of advertising.” – Milton Hershey

3. Ikutaro Kakehashi


During World War II, many people tuned in to their radios to hear the news. Kakehashi preferred to listen to music and grew fascinated with how radios worked. He decided to open a clock repair store where he eventually started working on radios. Unfortunately, Kakehashi faced a devastating hardship when he contracted tuberculosis. This forced him to give up on his business, so he could seek out treatment. Although this was completely out of his control, he was quarantined for a couple years.

Despite being so close to dying, Kakehashi prevailed and reopened his shop, now named Kakehashi Radio. His love for music inspired him to create a series of organs, electronic drums, and rhythm machines until he opened Roland Corporation in 1972.

Music is often associated with the musical success of stars on stage. Many people don’t know the vocals and backups you hear in the audience are controlled through a synthesizer, Kakehashi’s most famous invention. Artists such as Marvin Gaye, Whitney Houston, Lady Gaga, and many more have used the synthesizer and other inventions made by the Roland Corporation at concerts and in music videos. Before his death in 2017, Kakehashi received the honor of placing his handprint and signature on the Hollywood RockWalk in 2000 and earned a Technical Grammy Award in 2013.

Approximate Net Worth of Roland Corporation: $850 Million

“It’s easier to play when you have a rhythm.” – Ikutaro Kakehashi

4. Brian Chesky


Brian Chesky grew up in New York loving art, design, hockey, and bodybuilding. He received his degree in industrial design and moved to Los Angeles with future co-founder of Airbnb, Joe Gebbia. The two best friends were low on money, racking up debt, and unable to make their rent payment, so they had the crazy idea to rent out space in their apartment. They decided to go a step further and teamed up with Nathan Blecharczyk, another future co-founder of Airbnb, and went hunting for investors. After emailing 7 major investment companies in 2008, 2 never replied and 5 responded declining any involvement.

About a year later, the investment company Y Combinator took a leap of faith and provided Chesky with a much-needed loan. Airbnb started out by targeting locations that held big conventions because hotels nearby would quickly sell out of rooms. People were ecstatic to have alternative places to stay that were still conveniently nearby. Airbnb has reached over 34,000 cities and has had more than 60 million guests since they opened for business in 2008.

Approximate Net Worth of Airbnb: $31 Billion

“Never assume you can’t do something. Push yourself to redefine the boundaries.” – Brian Chesky

5. David Barnett


Originally a college professor with a PhD in Philosophy, David Barnett is nothing short of a genius. This didn’t stop him from failing a few times in his pursuit to become an entrepreneur.

Barnett grew frustrated with his headphones always getting tangled in his pocket on his way to work. He had an innovative idea to buy buttons and glue them on to the back of his cell phone. This allowed him to wrap his headphones tightly around the buttons and prevent a tangled mess. Determined to find a better solution, he spent 15 months making 60 different prototypes to make the first PopSockets. His invention never took off because cell phones are constantly changing.

Instead of giving up, Barnett went back to the drawing board and removed the case altogether and replaced it with adhesive backs. This meant PopSockets could be used on any mobile device, including cell phones, tablets, and music players. Barnett’s company took off without a hitch and has sold over 35 million PopSockets in over 40 countries around the globe.

Approximate Net Worth of PopSockets: $500 Million

“We want to build a brand, and we want people to understand that PopSockets is not just a product; it’s a real brand with real values.” – David Barnett

6. Elon Musk

SpaceX and Tesla

Elon Musk seemed destined to become an entrepreneur at the age of 12 when he programed, created, and sold his own video game. After graduating college with a degree in physics, he created and sold his first company Zip2 Corporation for $307 million. While this was a success, his other companies had epic failures. This includes PayPal being bought out by eBay and losing all his money for SpaceX from multiple rocket explosions.

Musk made history by creating the first privately-funded, liquid-fueled rocket to put a satellite into Earth’s orbit in 2012. SpaceX even teamed up with NASA to develop launch vehicles. Another one of Musk’s success stories is his company, Tesla, Inc. This car manufacturer changed the car industry by dedicating its efforts to making energy-efficient cars that run on electricity and solar power. Tesla’s Model S sedan has won many awards for the best car ever tested and high performance.

Musk’s determination has sent rockets into outer space and created fast, energy-efficient electric cars. He never gives up or accepts failure and you shouldn’t either.

Approximate Net Worth of Tesla: $45.6 Billion

“When something is important enough, you do it even if the odds are not in your favor.” – Elon Musk

7. James Dyson

Dyson Vacuum

James Dyson’s biggest interest was furniture and interior design. In college, a teacher introduced him to the possibilities of using his love of drawing with engineering new inventions. His first invention was called a ballbarrow, and it looked just like a wheelbarrow with a giant plastic ball instead of a wheel. He also created bagless vacuums. It took 5,127 different prototypes over 15 years before Dyson had a vacuum he could pitch to British retailers, which was rejected.

Despite being denied, Dyson believed in his product and launched it through catalogs in Japan. It became a huge hit and gave Dyson enough money to open up his own facility. Since launching, Dyson’s company has created not just vacuums, but also hair dryers, purifiers, bladeless fans, lights, and hand dryers. The company strives on innovation, and Dyson believes a lot of his success came from all his failed attempts.

Fast forward to 2020, and James Dyson has designed a new ventilator to fight COVID-19, even donating 5,000 of them out of his own pocket. It’s safe to say that his perseverance provided not only novelty products that are fun to use, but critical life-saving devices as well.

Approximate Net Worth of Dyson: $5.2 Billion

“Enjoy failure and learn from it. You can never learn from success.” – James Dyson

8. J.K. Rowling


J.K. Rowling began writing Harry Potter in the early 1990s after thinking up the idea during a train delay on her way home. However, every time the author was able to write more of Harry’s story, her attention was pulled away. By 1993 she had lost her mother, married, divorced, and was left to raise a newborn child on her own. This lead her down a dark road where she struggled with depression. She found solace in something she had previously given up on – writing. A few years later, she submitted a sample of her book to 12 major publishing firms. Almost all of them told her nobody would be interested in wizards and witches.

Although feeling defeated, Rowling kept submitting her book to publishers. About a year later, the 8-year-old daughter of an editor at Bloomsbury Publishing company read Rowling’s manuscript and loved it so much, the publishing company decided to publish the novel. Since the publication of Harry Potter and the Sorcerer’s Stone, Rowling has published 11 novels, 3 volumes, 2 screenplays, and produced 10 movies. She has won countless awards for her books and films and is one of very few authors to ever reach billionaire status.

Approximate Net Worth of J.K. Rowling: $25 Billion

“It’s impossible to live without failing at something.” -J.K. Rowling

Final Thoughts

The next time you’re feeling discouraged, don’t give up! You can do anything as long as you have the right mindset. Instead of thinking, “I can’t believe I failed again,” think, “Okay, that’s one more step towards success.” After all, you will never learn and figure out what works without first stumbling and doing something wrong.

The entrepreneurs featured above found success even when it seemed impossible. Let that be a lesson that anything is possible!

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