10 Legendary Mistakes Made By Successful Entrepreneurs

This post is not about pointing out the mistakes of others.

I’m not really a fan of that and that’s kind of the point of this post.

This is about seeing how even the most successful entrepreneurs in history have made mistakes. If you’re not making at least a few mistakes it’s usually a sign that you’re playing things too safe.

Being an entrepreneur is about taking risks. It’s just the nature of life. I’m not saying that successful entrepreneurs foolishly try anything. They calculate. They make decisions as best they can, but they still fail…but they also succeed.

So let’s look at some of the biggest mistakes entrepreneurs have made that haven’t held them back from being successful.

1. Sam Walton Lost His Ben Franklin Store

When I was a kid my grandparents lived in a small town in Western Wisconsin. I remember in the ’80s and ’90s that there was a small general or retail store called Ben Franklin in the downtown of the town.

Later I read Sam Walton’s autobiography and learned that he got his start owning a Ben Franklin. He ran it very successfully for a few years, but was swindled out of his lease for the building.

So Sam was very successful, but his failure, with hindsight, could have been that he didn’t look closely enough at his contract.

Now, I’m a believer in thinking the best of people. His landlord actually wanted to take back the store after it became successful and gave it to his son or something.

Sam was out on the street, but the situation led him to start his first Walton’s Five & Dime. We all know the success story that followed…

2. Jame Dyson’s Inability To Sell His New Vacuum

James Dyson had a great idea for a new vacuum cleaner in the late ’70s. His first failure could be seen in the many variations he created in designing what we now know as perhaps the best vacuum cleaner on the market.

However, I think a failure of his was his inability to sell his invention to big companies. Nobody wanted to take his idea and bring it to market.

Selling is obviously a big part of business and Dyson was failing in that area.

But his resilience eventually won out when he started his own company in the early ’90s and went on to become a billionaire.

Sometimes it’s the deals that don’t happen that turn out to be the best in the end.

3. Milton Hershey’s First Two Companies

One failed business venture would be enough to make most of us stop trying and look for something new to do…like getting a real job.

But one failure didn’t stop Milton Hershey. In fact, two failures didn’t stop Milton. After his first business went bankrupt he later started another company. That second company had some initial success, but then also suffered from cash flow issues.

Milton would stick with it, though, and he later helped a caramel company reach great heights and he turned his earnings into an investment into the Hershey’s company we know today.

4. Ray Kroc’s Plummeting Shake Machine Sales

Ray Kroc didn’t invent or own the Prince Castle Multi-Mixer shake machine, but he was a salesman for the company. However, sales eventually began to lag big time as the company was going out of business.

Ray Kroc knew he needed to make a change and he looked for opportunity.

He realized that a couple brothers had purchased some mixers from him. He connected with them and brought some ideas to the table for their restaurant. Eventually, Ray helped the brothers franchise out their company and Ray became head of the company.

That company is McDonald’s.

5. George Lucas Sold Pixar

In the mid ’80s, George Lucas was having some cash flow issues. That’s hard to believe since he was coming off three successful Star Wars movies plus his involvement in the Indiana Jones films.

However, Lucas was going through a divorce. He was investing heavily in new technology and his returns from Star Wars were beginning to fall off after peaking.

So he looked internally and decided to sell Pixar to Steve Jobs for $5 million in cash.

Pixar wasn’t an immediate success, but Jobs stuck with the company and the tides turned with the 1995 release of Toy Story and the rest is history.

Lucas has done just fine, too. He released another triology of Star Wars films along with many other successful projects before selling his empire to Disney. 

6. Sakichi Toyoda Suffered Many Failures

The founder of the company we know today as Toyota, invented many loom machines in his early days and many of them failed, but he did find success.

Toyoda apparently also had many struggles in his personal life, but his struggles and resilience led to the culture at Toyota and that culture has driven Toyota to success in numerous fields today even when they suffer setbacks.

7. Soichiro Honda’s Flaming Race Car

Honda built the company we know today around mistakes. He was famous for accepting mistakes, but not accepting repeated mistakes. He always wanted the company to be moving forward.

Move forward. Make mistakes. But learn from them, Improve.

An early race car from Honda went up in flames. It was embarrassing for the company that believed that building a race car was the best way to showcase the brand’s ability in the automotive field.

It could have derailed a lesser company, but that hasn’t happened to Honda.

8. Walt Disney’s Fantasia

Surprisingly, a number of classic Disney movies were not initially financial success stories. One of the know well known films from Walt’s early days was Fantasia.

The production and release of the film almost bankrupted the company. Walt kept pumping money into the film so he could see his vision through. The initial release did not go well.

But after many years and re-releases the film became a classic (finally seeing a profit in 1969) and is now one of the most appreciated Disney films.

And obviously even though the film almost bankrupted the company, Disney went on to continued success in numerous areas of commerce.

9. Henry Ford II’s Edsel

The automobile industry in the US has quite the history. Throughout that history you’ll find instances of failures. It just kind of comes with the territory of big innovation. Along the way there will be failure.

The Edsel came out in 1958 and was canceled a couple years later. This was when Henry Ford II was running the company. I’m not sure that he was in charge of the Edsel project, but since he was running the company at the time he ultimately was in charge.

There are many theories about the Edsel, but no matter what way you look at it, there was a big investment, a lack of sales and eventually scuttling of the project.

It’s a failure, but I admire the Ford company. They have been innovators throughout their history. They have had downs, but always seem to come back strong.

10. Masaru Ibuka’s Rice Cooker

Masaru Ibuka was one of the co-founders of Sony. Obviously we know Sony as one of the biggest companies in the world today. They make electronics. They’re huge in the music industry. We all know their incredible success.

But one of their first products was a rice cooker. Ibuka especially seemed to really key in on the idea of this rice cooker. There was a need with the population in Japan. It all made sense.

Except they could never figure out a way to make the rice cooker actually work and it bombed.

A failure like that would cripple most companies, but Ibuka and others at Sony kept on working to find something that would work and they became one of the most successful companies in history.

Conclusion

Any entrepreneur will tell you that they’ve made mistakes. Even the entrepreneurs I meet today are quick to remember their mistakes. It seems they remember the mistakes more than the successes.

But through all those mistakes are wins. Honda, for example, is quoted as saying that success is 99% failure. What a great quote.

If you’ve made a mistake or two in business don’t let it get you down. It happens to even the best. In fact, it probably happens to the best more often.

Dayne Shuda
Dayne Shuda
Dad, husband, golfer, and bow hunter. Owner of Ghost Blog Writers.

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