15 Successful Entrepreneurs With Reasons To Fail

Entrepreneurs That Had a Reason To Fail But Succeeded

It’s funny how often you hear of new entrepreneurs that have become successful overnight, or how much an entrepreneur has made from being successful but what you don’t hear about very often is their failures along the way. Some of the greatest entrepreneurs of all-time have failed at least once on their rise to glory. Although some are very lucky and born into wealth, or perhaps inherit a large sum of money which they use to invest, the majority of us like to hear about people we can more closely relate to. People that had it bad, sometimes very bad in fact, it’s a way of keeping us motivated and inspired and we all need that little boost once in a while.

By looking at the success of others who failed their first, second or even third time around it not only gives us that inspiration I speak of, it also gives us a little extra hope. Now I’m not going to say that money is made by hopes and prayers it takes a lot of determination and guts as well as hard work and the odd dose of good luck. But hope can lift us up when we need it the most, perhaps your business hasn’t gone as well as you had hoped? Maybe you have a blog that you just can’t seem to monetize to any degree of success? Well, hopefully after reading this list you will be able to not only relate to the people on it, but maybe, just maybe you will see that you haven’t got it half as bad as some of these entrepreneurs.

So grab a cup of whatever it is you drink, tea, coffee maybe a latte, and just sit back, relax and soak in all of the information before you. I hope you enjoy reading it and I hope it inspires you to go even further with whatever it is you are doing.

On with the list…

#1 Sir Richard Branson

Age: 60yrs

Birth Place: Blackheath, London, UK

Industry: Entrepreneurial Industrialist

Biggest Hold Back: Dyslexia, High School Dropout

Net Worth: £2.97bn ($4bn USD)

Website: www.virgin.com


Why they made the list..

Richard Branson, a high-school dropout (college dropout for you UK readers) started his first business in 1966 aged 16yrs, a magazine called Student, however it wasn’t without hard work and lots of studying. Richard has Dyslexia, although at the time no one knew what Dyslexia was. He had to overcome his fears and his Dyslexia so that he could publish his magazine and sell it. There was no other choice for him, he was too highly motivated to give up and work a 9-5 job. However his battle with Dyslexia was overcome and he went on to make a great deal of revenue with his magazine.

Then in 1970 he decided to create a company, a mail order record retailer, the first of it’s kind in the UK. He named his business Virgin, due to him being very new to business. Shortly after starting his business, he opened a brick and mortar store in Oxford Street, London, with his business becoming a success, he built a recording studio with the profits he had made and signed his first “Virgin” musician, Mike Oldfield (of Tubular Bells fame). In 1977 the Sex Pistols joined Virgin Records. Richard went on to create a further 200 companies and today is one of the UK’s wealthiest entrepreneurs. So if you have Dyslexia, like myself, and you think that’s a hurdle, forget it. Richard managed to overcome it, and so have I, you can too. Believe.

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#2 Oprah Gail Winfrey

Age: 56yrs

Birth Place: Kosciusko, Mississippi, USA

Industry: Talk Show Host and Media Proprietor

Biggest Hold Back: Poverty, Abuse

Net worth: ($2.7 billion)

Website: www.oprah.com


Why they made the list..

Now, before you all start with the fire and pitchforks hear me out, Oprah really is a brilliant entrepreneur, and not just a talk-show host. Born into poverty in Kosciusko, Mississippi, Oprah was unaware of the great hardship that she was to face later in life, only to rise from the ashes and become the star we know her to be today. At the age of nine Oprah was the victim of a ferocious sexual attack, which she revealed to shocked viewers on her show in 1986. She was further distressed when aged 14yrs she became pregnant and later lost the child. In 1983 when she found fame with her talk-show she became a huge success, and her following rapidly grew.

However by 1988 although a huge national treasure with hundreds of thousands of fans and viewers, Oprah had become weary of “Just working for someone else”. That year she founded her very own production company that she named Harpo Studios (Oprah spelled backwards). The business snowballed, probably likely credited to her television career that earned her unfathomable advertisement day in, day out. The company now has over 250 employees and is growing each year. She also co-founded the company Oxygen Media, which operates a huge network for cable and attracts over 50 million viewers. Outstanding achievements by anyone’s standard.


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#3 Donald Trump

Age: 64yrs

Birth Place: New York City, New York, USA

Industry: Real Estate

Biggest Hold Back: Went Bankrupt Several Times

Net Worth: $2 billion

Website: www.trump.com


Why they made the list..

What do you think of when you hear the name Donald Trump? Fame, Fortune or his books? I’m betting the last thing you would think of is bankruptcy right? Donald began working for his fathers company in the late 1960’s, The Trump Organisation working in real estate from an early point in his life. He managed to completely revamp a huge complex with only a 44% occupancy rate into a thriving complex with 100% occupancy in only a year, making his father’s company a nice $6 million in profit. Trump rose yet again into glory when he took on a massive project that the City of New York had nowhere near completed after two years and after having spent a huge $12 million on it. Trump managed to complete the entire project after taking over and used less than a third of the remaining budget.

However it wasn’t always great news and success for Donald. In 1989 at the beginning of a recession Trump, was left helpless against huge debts which had piled up due to the building of his new casino, the Taj, Mahal. The Taj Mahal had cost $1 billion in junk bonds and his debts increased further than anyone could have imagined. Just three years later in 1992 Donald was forced to sign a bankruptcy protection plan because he was unable to make payments towards the huge accumulating debts. He was now in personal debt of $550 million as well as the $1 billion in junk bonds. By 1994 his personal debt had totalled a disastrous $900 million! He eventually managed to restructure his bankruptcy by reducing his shares from 56% to 27% meaning the bulk of the debt would all but disappear. With the changing hands of the company shares the business changed it’s name to the Trump Entertain Resorts Holdings. Trump is currently worth an estimate $2 billion.



#4 Alijan Ibragimov

Age: 56yrs

Birth Place: Kyrgyzstan

Industry: Oil and mining Industrialist

Biggest Hold Back: Government

Networth: $1.9b


Why they made the list..

Alijan Ibragimov was brought up in Kyrgyzstan, and was brought up in poverty for his early years. However his background did not stop him becoming a billionaire. Early in his career Alijan had decided he wanted to work for himself rather than work hard hours of manual labour, in the poverty stricken country. He and a number of his friends got together and formed aoligarchs, known as “The Trio”. The Trio includes Alijan himself, and business partners Alexander Mashkevich and Patokh Chodiev. Their business was within the oil and gas industry in which they mined for the resources.

The Trio then became major shareholders in the global group Eurasian National Resources Corporation (ENRC), which now resides in London and is in control of a plethora of assets within the Eastern hemisphere. ENRC went on to make over $1,400 million in profits, through sales of nearly $4 billion. However the government allegedly “forced” Alijan, into selling a quarter of his shares in ENRC to a fellow billionaire, named Kazakh. Alijan has been named in the Forbes list of top richest people in the world, and is still on the list to this day.


#5 Walter “Walt” Elias Disney


Age: 65yrs (Died December 15th 1966)

Birth Place: Chicago, Illinois, USA

Industry: Entertainment/animation

Biggest Hold Back: Bankruptcy & Told He Would Fail

Net worth: $1.1bn

Company Website: www.disney.go.com


Why they made the list..

I’m pretty certain almost everyone (if not everyone) will know who Walt Disney is, and he is a great example of a successful entrepreneur. After dropping out of school and being refused entry to the army due to his age, Walt went on to work for the Red Cross. Upon his return to Chicago he managed to gain employment through his brothers collegue as an artist for a local business, where he created adverts for newspapers and movie theatres. After leaving his job, he and fellow artist, Ubbe Iwerks, started the Iwers-Disney Comercial Artist Company, which fell after a very rocky start. He was then offered a job by the Kansas City film Ad Company, where he learned how to create animations from cut-outs. However after reading the book; Animated Cartoons: How They Are Made, by Edwin G. Lutz, Walt decided to leave the Kansas City Film Ad Company and try once more with his own business.

Laugh-O-Grams his second business went out of business due to bankruptcy, mainly because he had studio costs, far too many staff and not enough revenue to pay everything, disaster. Walt had failed not once but twice, but he didn’t know how to give up. Having learnt very really lessons in how to fail, Walt and his brother Roy went to Hollywood in search of glory. Whilst there he managed to secure a distributor to help with his business. Things went from strength to strength, it started with his live action Alice in Wonderland stories, and then continued with his own unique characters such as Julius the cat and Oswald the Lucky Rabbit. His real success came with Mickey Mouse when he made a series of animated shorts such as “Silly Symphonies” and “The Skeleton Dance”. In 1932 after popular demand for the character Mickey Mouse by all of his new found fans, Walt received an Academy Award. He had made it, thanks to help of a little fictional mouse called Mickey. Walt continued his success for a further 34yrs before his death, leaving behind his legacy which we all now know as the Walt Disney Company, which is worth somewhere in the region of $35 billion today.



#6 Henry Ford

Age: 83yrs (Died April 7th 1947)

Birth Place: Greenfield Township, Dearborn, Michighan, USA

Industry: Auto-motive manufacturer

Net Worth: $1.1 billion

Biggest Hold Back: Bankruptcy, Dyslexic

Company Website: www.ford.com


Why they made the list..

Henry Ford, we all know of him don’t we? One of the few men that made the car become a reality. He was born into a family of farmers who originated from England and Ireland. Not the wealthiest of families but certainly not poverty stricken. In his teenage years, his father had given him a timepiece, which he later took to pieces just to see if he could piece it together again successfully, which he did. He then started to do the same with other peoples timepieces and eventually he started to repair them too. He quickly became know as the young watch repair man. How ever clocks, and watches were not what he wanted to be involved in as a career. After his mother died in 1876 he was left distraught and told his father he did not want to be part of the family business.

He went on to complete an apprenticeship with James F. Flower & Bros, and also with the Detroit Dry Dock Company. In 1891 he met with Thomas Edison who liked his concept of an auto-mobile, so he allowed him to use his warehouses to manufacturer two vehicles. Ford was grateful but later went on to build his own company so he could build the cars on his own terms backed by William H. Murphy he founded the Detroit Automobile Company (1899). This was short lived however not only because the vehicles produced lacked the quality and precision Ford wanted as well as being horribly expensive, but they were so expensive that the company went bankrupt! The business went under but it didn’t stop him. Ford went on to build the Cadillac Automobile company. After almost failing a second time due to lack of sales and high debts more partners came into the business and the name was changed to the Ford Motor Company. Current sales for the Ford group are now a massive $190 billion. Wow! The rest as they say, is history.


#7 Dame Anita Roddick

Age: 64yrs (Died 10th September 2007)

Birth Place: Littlehampton, UK

Industry: Cosmetics

Biggest Hold Back: Lack of time (motherhood)

Networth: £652.3 million ($1.03 billion)

Website: www.anitaroddick.com


Why they made the list..

Dame Anita Roddick, may not have had a poverty stricken lifestyle, but she was a mother who at the same time as caring for her family, was able to create a thriving business. Anita’s story is about motivation and passion and one I hope you all can relate to. Starting back in 1970 Anita and her husband Gordon opened up a restaurant business, however Anita wasn’t happy with this and wanted something more suited to her personality. She created The Body Shop in 1976 with just 15 products that she had sourced herself from around the world. Anita had traveled extensively before opening up her business and with her husband and two girls in tow she set off to create something special.

Faced with a massive task of getting the shoppers in the UK to part with their money for “Greener” products, but with a motivation, a dollop of passion and a pinch of luck Anita managed to succeed. Luckily for Anita just as she was halfway through her first year the UK shoppers had a change of heart and started shopping for these “Green” products she was selling. She opened another store and another, and another, they just seemed to grow and grow. Anita had managed to build her empire to a whopping 1,980 The Body Shop stores, totaling in more than 75 million customers worldwide in 50 different countries by 2003 and was then bought out in a very controversial deal with L’Oreal it was controversial due to The Body Shop not using ANY products tested on animals, as opposed to L’Oreals company that did. The deal made her £652.3 million ($1.03 billion) better off which was more than well deserved for her fierce years of service. I hope Dame Anita managed to enjoy that money for the remainder of her life.



#8 Ray Kroc

Age: 81yrs (January 14th 1984)

Birth Place: Oak Park, Illinois, USA

Industry: Fast Food

Biggest Hold Back: Confidence

Net worth: $500 million

Company Website: www.mcdonalds.com


Why they made the list..

You didn’t think I was going to leave Ray out did you ? What’s that, you don’t know who Ray is? Sure you do, you visit his restaurants at least once a month (Unless you’re a vegetarian, in which case I apologize). Ray Kroc is best known as the man behind McDonald’s. Ray, was an unsuccessful entrepreneur, and was also good friends with Walt Disney I might add. After the war ended Ray went on to try unsuccessfully a number of different career paths, a jazz musician, a pianist, he even tried to sell paper cups, but his confidence just wasn’t there anymore, he’d lost a little faith. After leaving the cups behind, he went on to sell milkshake machines, and found that he was pretty good at it. His confidence rose and he was selling them by the dozen.

Convinced with his new found confidence he sell a machine to every restaurant he partnered up with a couple of brothers by the name of McDonald. They were starting to franchise their own business, a fast food restaurant. The McDonalds brothers went on to build a fair amount of stores and were raking in the money, but Ray wasn’t happy, he was hungry, hungrier than ever now he’d tasted success. So he used all the money he had made ($2.7 million) to buy out the two brothers in a bid to franchise the business everywhere he could. Ray discovered that the way his business should work, should be almost like a production line, that way he could work quicker and serve more customers. He was right. His technique meant no customer would go from being served to having their order in their mouth in more than five minutes, hence the coined phrase of “Fast Food”. By the time of his death Ray Kroc had built an empire of over 10,000 restaurants globally and that has grown to a massive 31,000 today! McDonald’s currently makes $23 billion each year. What an achievement.

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#9 Duncan Bannatyne


Age: 61yrs

Birth Place: Clydebank, Edinburgh, Scotland

Industry: Health and Beauty

Biggest Hold Back: Lack of Start-up Funds and Community

Net worth: £320 million ($450.7 million)

Website: www.bannatyne.co.uk


Why they made the list..

Duncan Bannatyne is a well known entrepreneur in the UK, known famously for his role in the television series Dragon’s Den (BBC). In his early life he was poverty stricken like a lot of families that grew up in the 1950’s in Scotland. Aged 15yrs he wanted a bicycle but was denied one due to lack of money within the family funds. To remedy the lack of having a bicycle, he decided to find some sort of work, asking one of the newsagents for a job, they told him “You can have you can get a list of one hundred interested people”, to cut a long story short, he knocked on hundreds of doors until he made the list, and got a job. Aged 20yrs, after years of loyal service in the Navy, Duncan was dishonorably discharged for attempting to throw an officer off a jetty, due in part to the officers abusive behavior.

Duncan spent his twenties going from one pointless job to the next, in search of something more, he craved his own business and wanted to succeed without being told what to do by others. He moved to Jersey where he met his wife. Through countless failures due to the Jersey community not welcoming business from outsiders, Duncan and his wife Joanne left the island. With only enough money to get by with, Duncan risked it all and bought an ice cream van for £450 ($714), within 2yrs he had managed to build such a successful business from it that he had bought several other vans, with employees to work them for him. He eventually left the ice cream business £28,000 ($44,430) better off which prompted him to invest the money into a nursing home, the nursing home was expanded upon and he eventually sold it for a cool £26 million ($41.2 million) and a childrens nursing chain he’d bought along the way for a further £22 million ($34 million). Since then Duncan has gone on to make £320 million ($507.77 million) through building an empire of luxury spa’s and health centers.


#10 Ruth Ann Udstad Fertel

Age: 75yrs (Died April 16th 2002)

Birth Place: New Orleans, Louisiana, USA

Industry: Restaurant

Biggest Hold Back: Fire destroyed her first restaurant

Networth: $235 million

Company: Ruth’s Chris Steak House


Why they made the list..

Ruth Fertel, became the first female horse trainer in Louisiana aged just 24yrs old, whilst owning a racing stable with her Husband Rodney, who she later divorced in 1958. After realising she could not raise her two son’s on the alimony she was given. Ruth then tried a few jobs until in 1965 she saw an advert in a newspaper advertising a local restaurant that was up for sale, named Chris’s Steakhouse in. She immediately re-mortgaged her house in order to buy the restaurant in a bid to work for herself. Shortly after purchasing the Steakhouse there was a huge hurricane that left the building without power, instead of letting the food in the freezer go to waste, she managed to cook it all elsewhere and took it to her local Parish to help those in need. Chris’s Steakhouse is back up and running in no time and the business was doing well, until a fire which broke out destroyed the restaurant.

With her entrepreneurial streak not willing to give up, Ruth bought another property just a few blocks from the original restaurant, but found complications with the naming of her new business. A legally binding document stated that the name Chris’s Steakhouse could not be used or replicated anywhere other than on the plot of the original building. She renamed the business Ruth’s Chris Steakhouse. Then in 1976 after several failures a local customer convinced Ruth to open up his own franchise on a very busy highway in Baton Rouge, Louisiana. The success of this franchise was immediate and other friends, family members and associates tried to convince her to let them open their own franchise too. Her success was huge and by 1985 she had over 15 other franchises, by 1992 she was awarded the Regional Entrepreneur of the year, by 1995 she was awarded the National Entrepreneur of the year and in 2001 she won the Ella Brennan Savoir Faire Award. A very clever lady indeed.


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#11 Deborah Meaden

Age: 51yrs

Birth Place: Somerset, Devonshire, UK

Industry: Investor

Biggest Hold Back: Legal disputes

Networth: £100 million ($158.6 million)

Website: www.deborahmeaden.com


Why they made the list..

Another Dragon from the den here, and although not as wealthy as our other entrepreneurs she has made a success of herself through hard work and determination. Aged 19yrs Deborah was enthusiastic about business and wanted to make something of herself, she did this by creating her own company selling ceramic and glass goods to stores such as Harvey-Nichols. However when her competitors saw how well she was doing they “upped” their game and tried to push her out of business, selling much of the same products as she was at a slightly lower price. Of course the stores went with the lower price and with Deborah just starting out, she had no legal understanding of what to do, and had no money to pump into a solicitor to fight the battle for her.

After getting out of the ceramics industry she went on to start a franchise with a friend in the retail industry, but it just wasn’t enough for her, she craved something larger, more satisfying. With that in mind she set up a prize concession at a Butlin’s. This taught her a lot about business and she went on to create several highly successful businesses across a couple of different sectors. Deborah has recently sold her shares in the holiday park business after it was sold on to Parkdean Holidays making a cool £83 million on top of the £33 million she previously made by selling 23% of her shares some time earlier.



#12 Martin Goodman

Age: 84yrs (Died June 6th 1992)

Birth Place: Brooklyn, New York, USA

Industry: Publishing

Biggest Hold Back: Finances and Homelessness

Net Worth: $125 million

Company Website: www.marvel.com


Why they made the list..

During the 1920s Martin Goodman, was homeless, walking around New York City, without money or shelter, he would often stay in “hobo camps”. His luck changed when he managed to convince/land a job with a publishing company as a salesperson. He enjoyed his work but wanted more, he wanted to be a publisher not a pen pusher. He and his new found friends Louis Silberkleit and Maurice Coyne, started the Columbia Publications Company. Goodman decided to leave in 1932 as he wanted to work truly for himself with no one to push him around. Then in the same year, after borrowing some money for capital, he started the company Western Fiction Publishing. His very first publication was the Western Supernovel Magazine, which was published in 1933. However after the first copy had gone out he decided to change the name to the Complete Western Book Magazine, hoping to attract more buyers.

Goodman decided to try and use a strategy to gain more customers, he did this by using various corporate names to brand his publications one of them being the Marvel Science Stories. In 1939 after many failed attempts at gaining the following he desired he created a comic book in a bid to jump on the new trend of publications. He named the test book Marvel Comics. The first ever copy featured the human torch and the Sub-Mariner. He quickly sold 80,000 copies his largest quantity to date. He was amazed by the sudden rush just for a comic book, he created more characters and with his second serving of the comic, he sold over 800,000 copies! Goodman carried on creating comic book hearos and characters for another 40yrs. At the time of his death in 1992 he was worth an estimated $125 million.

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#13 Milton Hershey

Age: 88yrs (Died October 13th 1945)

Birth Place: Derry Church, Pennsylvannia

Industry: Confectionery

Biggest Hold Back: Bankruptcy and a Failed Apprenticeship

Net Worth: $100+ million

Company Website: www.hersheys.com


Why they made the list..

Milton Hershey was brought up on a farm, and was the only surviving child of the Hershey family. Milton left school aged 14yrs mainly due to the amount of times his family had moved over the years. Without any qualifications he went on to start an apprenticeship as a junior printer. However this failed when he got frustrated with working as a junior printer and he threw his hat into the rollers, destroying the print that was currently being made. He then went on to complete a four year apprenticeship with a candy manufacturer (Joseph Royer) and in 1876 he built his first business, a candy manufacturing company. This didn’t work though and he found himself without a job or a business when he couldn’t get any sales.

Later in 1883, he built a new business the Lancaster Caramel Company, this swiftly became the leading manufacturer of candy-goods. With a special caramel recipe which he had discovered whilst travelling, Milton’s business soon became the king of the candy world. A decade later he became amazed by the way in which the German’s machinery made chocolate at an event, he quickly purchased some of the machines and headed back to his company. Enthralled to be able to create the luxurious milk chocolate, Milton started manufacturing thousands of tonnes of the candies. His sales soared higher than he ever thought possible, and to this day, although Milton passed 65yrs ago, his business is still going strong, with over $5.3 billion in revenue a year, not to mention much of the traditional recipes Milton used back at the beginning. Goes to show, remember where your roots are!



#14 Robert Kiyosaki

Age: 63yrs

Birth Place: Hilo, Hawaii, USA

Industry: Investments

Biggest Hold Back: Bankrupt several times

Net Worth: $80 million

Website: www.richdadcoaching.com


Why they made the list..

Robert Kiyosaki is a Hawaiian businessman who made his name after building a company that sold velcro wallets. Although this was a great success to begin with the sales numbers dwindled as more and more stores started to import them. The company later went bankrupt and Kiyosaki was left in debt. His second business was a T-shirt company, which was very short lived, even more so than his wallet business. For the second time in his career he became bankrupt. Robert had no idea what to do about his failures as a businessman. One thing was certain he did not want to work for anyone but himself. This got him thinking and he started to realise that he could become a guru, a public speaker, someone who can teach others how to make money. He decided to set up a seminar, they quickly gained influence and popularity and were an instant success.

He became business partners with a man called Marshall Thurber, but he retired not long into their partnership, Robert decided to buy Marshall out and became partners with Marshall’s business associate D. C. Cordova. Within their first year together the pair were once again bankrupted. That wasn’t the end though, determined to get rich or at least never give up trying, Robert and Cordova battled on over the next decade until eventually took off and Robert began travelling the world speaking to people from all walks of life about money. Robert retired aged 47yrs old, but it wasn’t enough he had the hunger, so he came out of early retirement in a bid to feed his passion. He created a new company called Cashflow Technologies Inc and he created a boardgame called Cashflow 101, but it had varied success, his main moment of glory came when he wrote his book, “Rich Dad, Poor Dad” it was a best seller in 90 countries and in 18 languages, you can even buy the book still now if you haven’t already read it?



#15 Thomas Alva Edison

Age: 84yrs

Birth Place: Milan, Ohio, USA

Industry: Science

Biggest Hold Back: Science

Net worth: $12,000,000

Biography Website: www.thomasedison.com


Why they made the list..

That’s right we’re going old school, very old school. Thomas Alva Edison one of the greatest inventors and entrepreneurs in history. Now although Thomas didn’t have a terrible upbringing in terms of the money sense, he was a very poorly child. Ill a lot of his early life, he suffered from a severe ear infection that rendered him deaf in one of his ears although it has been said he was deaf in both. He also developed scarlet fever as a boy nearly dying because of it, but it didn’t stop him. After becoming a minor celebrity for saving a toddler from being hit by a train, Thomas was offered a job as telegraph operator. Some say this is where his career began, after he was fired after he spilled sulphuric acid onto the desk of his manager who was sitting at his desk below Thomas.

Thomas went on to create thousands of inventions and patents, failing a lot more times than succeeding. However his first taste of glory came when he developed the tin foil phonograph, after working as a telegraph operator he wanted to create a way of making a telegraph transmitter to work in a more efficient way. He did this by realizing that it sounded very similar to spoken words when the tape from the machine was played at a fast pace. Developing his idea further he went on to record a message through this means creating his first successful invention that lead the way for many more. Thomas Edison was a very patient and passionate man, motivated by success he went on to try and fail thousands of times before getting some of his inventions to work. Some of his inventions we still use today, and most of them are historical for changing the world.

Now What’s Your Reason To Not Succeed?


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