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25 Unusual Business Ventures These Millionaires Tried Before They Hit It Big

It’s fair to assume that most people grow up dreaming of making it big. This means different things to different people. For a lot of people, the motivation is earning money. People aspire to become celebrities because of the money factor. They embark on business ventures because of money. After all, money is what makes the world go around.

Self-starters often set themselves targets. The whole point of starting a business and having a successful business is making a profit. That million-dollar mark is often imprinted in a lot of people’s minds. It’s what they aspire to achieve.

A lot of people dream about starting their own businesses. But starting your own business is no duck walk. You’ve got to be made of stern stuff. It’s not going to become a success overnight – unless you’re incredibly lucky, that is. Most people have to encounter some tough times before seeing success. That’s certainly what happened to these 25 businesspeople.

These 25 may live the high life now, but it hasn’t always been plain sailing. A lot of their initial business ventures never got off the ground. If they did, they didn’t make it big. Rather than get disheartened, these individuals got back on the horse, so to speak. They all found success – big time. These are 25 millionaires who, before acquiring their millions, had rather unusual business ventures, some of which did not go according to plan.

25 WORKING AS A SALESMAN

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Alan Sugar’s famed for starring in the UK version of The Apprentice. The business magnate founded the electronics company, Amstrad. Alan has also become something of a legend.

Those who are familiar with Alan will know a little something about how Alan used to make his money. One thing that Alan did was sell. After leaving school, he got a job as a statistician. Then he got himself a van and started selling electrical goods such as radio aerials for cars. He was always a self-starter.

24 MAKING A LIVING AS AN ICE CREAM SELLER

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Duncan Bannatyne may not be known to a worldwide audience. But he’s big in the UK. He’s famed for starring in Dragon’s Den.

Duncan made his fortune owning health clubs and spas. But up until the age of 30, he was lost. He was broke and was moving from job to job, not knowing what he wanted to do with his life. His first foray into the world of business was when he purchased an ice cream van. He ended up buying several before selling the business for £28,000. It didn’t make him millions, but it was a decent start.

23 STARTING A HOUSEKEEPING BUSINESS

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There are some millionaires that just like to go about their business and fly under the radar. Alice Alonzo is one of them. She made her millions by manufacturing and selling candles. Her ingenuity meant she used recycled machinery to make the candles. She now produces around 3000 a day. She started this business using the money she saved from her housekeeping business. She worked hard, scrimped and saved, and eventually got enough capital together to start out on her own.

22 BLOGGING

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Jenna Marbles is part of this new wave of millionaires. She’s used social media to make her millions. Jenna is famed for her YouTube channel. She once had the accolade of having the second most popular YouTube channel in the world operated by a woman. But before becoming a social media star, Jenna tried her hand at this and that. She worked odd jobs, including working as a bartender and dancer. One of her initial business ventures was as a blogger.

21 WORKING AS A STAND-UP COMEDIAN

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Sarah Blakely is a name that probably rings a bell. Forbes have rated her as being one of the most powerful women in the world. She made her millions – billions, in fact – by founding an intimate apparel company.

Before making it big, Sarah had aspirations to become an attorney. But instead of going to law school, she decided to get into the world of work. One of many ways she made money was putting gags together and performing as a stand-up comedian.

20 STARTING SEVERAL UNSUCCESSFUL CANDY COMPANIES

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Hear the name Milton Hershey, and you should instantly know who I’m talking about – unless you’re not into chocolate, that is! Hershey is known as the chocolate king.

A young Hershey worked on a farm, was an apprentice to a printer, and then got into the candy business. His mom wanted him to learn the candy trade, so sent him to be apprenticed by a confectioner. He started his first confectionary business in 1876. Things didn’t go according to plan. Neither did his second attempt.

19 STARTING A FETA CHEESE IMPORT BUSINESS

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Hamdi Ulukaya hails from Turkey. He’s founder and CEO of the number one strained yogurt brand in the U.S.

Hamdi comes from a dairy farming village. Hamdi moved to the U.S. to further his studies and became interested in starting his own business. He took courses and eventually took the plunge. Hamdi imported feta cheese from his dad’s farm. He eventually opened his own plant in the U.S. It was modestly successful but only lasted two years. As Hamdi recalls, "It was two years of the most challenging days of my life."

18 STARTING A TRASH SORTING BUSINESS

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Trining Climaco’s story is one of rags to riches. When she was younger, she was really poor. She had aspirations to become a lawyer. But schooling wasn’t an option for her. At the age of 11, Trining worked in her uncle’s junk shop in San Juan. She grew up and got married. Her husband was also in the business. Trining eventually started her own trash sorting business. Things progressed and she opened her own junk shop. Believe it or not, that’s how she became a millionaire.

17 SELLING SHAWLS

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Raj Kundra is a massive name in India. He’s revered like an A-list celeb. Now he has his hands in many pies, so to speak. He’s involved in many ventures and is sitting comfortably on top of a vast business empire alongside his wife, actress Shilpa Shetty.

Raj was born in London. He held numerous jobs after leaving school. One of his ventures was travelling around Asia, making contacts, buying shawls and selling them to people in the UK. It was a simple business but one that brought him a decent amount of success.

16 STARTING THE BRAND DEWAS DEWAN

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Johnny Earle is better known as Johnny Cupcakes. He’s made his millions by selling t-shirts. Cupcakes are a prominent design of his merchandise. It sounds like a relatively simple concept. But it’s one that’s taken off.

Initially, Johnny started off in fashion with the brand "dewas Dewan." This wasn’t the almighty success he hoped it to be. But things soon changed. He created another brand. He now has his own store in Boston and a very successful online store. It’s certainly a worldwide brand.

15 STARTING A WEB HOSTING COMPANY

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Nowadays, if you’re tech-savvy, there’s a plethora of opportunities open to you. Hiten Shah used the world wide web to earn his millions. He’s created a million dollar per year start-up. Those of you who are in the know will appreciate that that’s pretty rare. He now runs three successful online companies. But even with his know-how, he couldn’t envision how his entrepreneurial journey would begin. Before all the success, Hiten had his own web hosting company. Although it wasn’t a total loss, its numbers were pretty low compared to what he’s earning now.

14 CREATING SITE PYP MEDIA

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At the age of 32, Kathryn Minshew is one of the youngest people on this list. She’s co-founder of The Muse and has developed into something of an all-round media personality. She’s won plenty of awards and accolades over the years, such as Entrepreneur of the Year, Game Changer awards, and one to look out for. It hasn’t all been plain sailing. Kathryn built on her success after learning from mistakes. She was the co-founder of PYP Media. But as she describes it, she was stabbed in the back by the other co-founders. She certainly showed them.

13 WORKING AS A STRUGGLING WRITER

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You don’t have to be a fashionista to have heard the name Vera Wang. She’s a massive name in the fashion industry. Her designs are frequently shown in all the top magazines. They’re worn by A-list celebs.

Vera built her name in fashion and will always be in that industry. But not a lot of people know that she actually did some writing. Sure, now she’s the figure she is, she does a lot. But back in the day it was how she was earning her corn – and not a lot of it, let me tell you.

12 WORKING AS A STRUGGLING WRITER (AGAIN)

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Ariana Huffington is another name that should ring some bells. Although it might surprise a lot of you that Ariana’s on this list as a struggling writer. She’s the co-founder and editor-in-chief of The Huffington Post. She’s also ventured into politics. Forbes labelled her as being one of the most influential and powerful women in the world.

Ariana was writing books in the 1970s. Those initial works of writing didn’t prove to be the successes she’d have hoped them to be.

11 CO-FOUNDING TRAF-O-DATA

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Bill Gates is probably one of the most famous rich men in the world. He’s a business magnate and the principal founder of the Microsoft Corporation. He’s not just rich, he’s seriously rich. According to Forbes, he is the second richest person in the world.

In the 1970s, Bill co-founded Traf-O-Data. It was geared towards getting traffic information to engineers. It achieved a moderate amount of success. But it actually proved to be the stepping stone onto something bigger for Bill.

10 CREATING UNSUCCESSFUL VACUUM PROTOTYPES

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When inventing something you want to bring to market, you’ve got to create prototypes of the product. You’re not going to get the product right at the first time of asking. There’s going to be constant tweaking and adjusting before you have the perfect product. For James Dyson there was a lot of tweaking and adjusting. He created a staggering 5127 vacuum prototypes before he had a product he was happy bringing to market. That’s the sign of a perfectionist right there.

9 STARTING A TEXTILES COMPANY

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In all likelihood, Momofuko Ando is a name you haven’t heard of. But you’ve probably had his product. He’s famed and earned his millions for inventing the instant noodle, instant ramen and cup noodles.

From a young age, Momofuko was into business. He started a textiles company after gaining experience in that industry from his grandparents. Whilst studying at university, he also established a clothing company. That’s a far cry from instant noodles, which started after he lost his clothing business due to bankruptcy.

8 CREATING A SOCIAL MEDIA NETWORK

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Reid Hoffman always wanted to do something big. While at college he decided he wanted to influence the world in some way or other. In a way, he managed to do that with LinkedIn. That’s what’s earned him his millions. But before that, Reid tried his luck making it big with other online ventures. He worked on creating eWorld, which was an attempted at an online dating and social media network. It didn’t work but was an idea before its time.

7 OFFERING DISCO LESSONS

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American businessman and invested Mark Cuban is someone who loves life in the limelight. He’s written books, has invested in TV shows, and owns the NBA team, Dallas Mavericks. Basically, you get the idea that Mark would do anything to make money. Look through his job history, and yes, that’s pretty much the case. Mark’s held a ton of jobs over the years. One of the most unusual was him working as a dance instructor when he set up a disco lesson business while at university.

6 STARTING A FASHION BOUTIQUE

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James Caan – not the actor – is a big deal in the UK. He’s famed for starring in Dragon’s Den. James earned his millions in the recruitment industry. He’s also an investor. But he’s done a number of things along the way.

As a young man in his early 20s, James worked for several recruitment companies. He didn’t have any work experience, so just fell into that line of work. It was at this time that he started a fashion boutique with his wife.

5 CREATING ZUCKNET

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This just goes to show that even the world’s most well-known wealthiest people have to start somewhere. The tech entrepreneur and co-founder of Facebook, started off creating programs way back in the 90s. He created programs to find solutions to problems. Zucknet was one of his early creations. Mark formed it as a means of helping his dad, so that the house and dental office computers – his dad owned a dental practice – could be synced and communicate with each other.

4 STARTING A GLASS AND CERAMICS EXPORT AGENCY

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Deborah Meaden is another well-known name in the UK. She’s famed for being one of the dragons on Dragon’s Den. How did she earn her millions? She ran a caravan park. Yes, that really is as random as it sounds. It was a very good caravan park. It made her plenty of cash. She’s had what others would deem to be pretty unusual business ventures too. As a teenager Deborah set up a glass and ceramics export agency in Italy. It went under after just over a year in operation.

3 STARTING A SPORTS AGENCY

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Noel Biderman is an internet entrepreneur. He’s also a business and marketing specialist. Incorporate those two professions and you’ve got one hell of a combination. Noel may be famed for his association with the Ashley Madison Agency. Many consider it to be quite a sleazy company. But Noel knows what works. He’s a very intelligent man. Noel’s a qualified and practiced lawyer. One of his previous ventures was also as a sports agent. He’s got the gift of gab, and knows how to turn a success out of anything he tries his hand at.

2 WORKING AS AN ELECTRONIC GOODS SALESMAN

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American businessman Nick Woodman is the founder of GoPro. It’s a tech company that essentially manufactures action cameras.

After completing his university education, Nick Woodman thrust himself straight into the world of business. He founded two startups. Both didn’t go as planned. In fact, his website, which sold electronic goods, never really made it off the ground. Neither did his gaming and marketing website. The platform remained stagnant. Luckily for Nick, he had the backing of some influential people. He made GoPro happen.

1 CREATING A MAGAZINE

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Nowadays, Richard Branson seems to be doing anything and everything. He can afford to. He’s sitting pretty with a ton of cash in the bank. Richard really has tried his hand at a ton of ventures. Most have been successful. One that was moderately successful was when he created a magazine. It was a student magazine. When he advertised records in the magazine, it became even more of a success. Richard even managed to interview a few prominent personalities of the time.

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