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5 Unconventional Entrepreneurs Who Found Success Out of Box

If you can dream it, you can do it! 

Yet so many of us can’t find the inspiration to keep our dreams afloat and have to trade them for the harsh realities of ‘making a living’.

While life will keep on giving you lemons, there are also a few unconventional entrepreneurs that will make you want to do more, catalyze your life’s potential and create something new.

Here are 5 of our fav unorthodox entrepreneurs that will definitely want you to change the world !

#1. Blake Mycoskie

The philanthropist guy who built a $625 million for-profit on karmic capital

unconventional entrepreneurs

A serial entrepreneur, @BlakeMycoskie was already running his fourth entrepreneurial startup when he took time off from work to visit Argentina. What he found there changed his as well as the life of more than 60 million children – the beginning of his one for one venture, TOMS.

TOMS (stands for “Tomorrow’s Shoes”), a for-profit shoe manufacturing company, was born after Mycoskie saw a children’s shoe charity struggling to meet the ends. He knew he had to help and came up with a company with an unconventional concept – Sell a pair of shoes today, gives a pair of shoes to a child in need tomorrow. And the rest is history.

Inspirational Takeaway from Blake:
“The most important step of all is to take the first step – start something.”

#2. Michael Dubin

The serious guy who turned a funny video into a $1 billion business

unconventional entrepreneurs

The Dollar Shave Club CEO @Michael Dubin might seem like quite the comedian in the brand’s  subscription video, but his success is anything but funny.

The taciturn entrepreneur introduced his company to the world with a slapstick youtube gig, showcasing “Why our blades are f***king awesome”, fetching them 5000 subscribers on the first day alone. Today, Dollar Shave Club is the second-largest men’s razor brand in America — succeeded only by Gillette.

Inspirational Takeaway from Michael:
“If you can create content that goes viral it’s going to be cheaper for you to build your business.”

#3. Andrew Warner

The 21-year-old guy who created a $38.5 million business by returning his clothes

unconventional entrepreneurs

Not to be the one born with a silver spoon, @AndrewWarner still managed to become one of the pioneers of internet startup scene. His first venture started with Andrew returning his J.Crew clothes for funds and ended up becoming a $38 million plus per year internet business.

The 90’s wonder now runs a motivational interview website, Mixergy where he invites successful startup owners to inspire budding entrepreneurs. On Mixergy, he has had the founders of Wikipedia, Groupon, LivingSocial, LinkedIn, and over a thousand other fascinating start-ups.

Inspirational Takeaway from Andrew:
“I hate the pansies who whine that “it takes money to make money.” No it doesn’t! It takes a sense of mission. If you’re on a mission, you’ll find a way”

#4. Jason Zook (Formerly Jason Sadler)

The bored guy who got paid $500,000 a year to wear T-shirts

unconventional entrepreneurs

Wearing a T-shirt might not be the most unique thing in the history of the world. But what if you could convert wearing one into a profitable, buzz worthy, growing business? @JasonZook somehow did it.

Started on a whim, Sandler’s bright idea of selling ad space on his chest gave birth to IWearYourShirt which managed to bring him $500,000 per year and a famous client list that includes big guns like Arizona Tea, Starbucks, Pizza Hut, Nissan, and Lucky Brand.

Inspirational Takeaway from Jason:
“There is no greater satisfaction than going to sleep at night, knowing that I work for myself and waking up every morning to continue to bring life to an idea that few people thought would succeed. And that feeling is far more valuable than any paycheck.”

#6. Matthew Inman

The creative guy who twirled a snarky bowl of breakfast into a $500,000 annual paycheck

unconventional entrepreneurs

After selling his hugely successful dating website, @Matthew started a comic blog out of passion. When one of his comics, How to tell if your cat is plotting to kill you blew up big, he came up with TheOatmeal. The blog received 5 million visits per month within a year after its launch, making Inman internet’s most beloved viral marketer.

Inspirational Takeaway from Matthew:
“A lot of people say: ‘How do you do it?’ I just make things that people like. SEO has no bearing on the Oatmeal — I did SEO in my old job [so I know] — but social media has played a gigantic part in what I do.”

How these Entrepreneurs Inspire Us

The most important takeaway we get from all these inspirational figures is to follow your own calling – your very own dreams. Do something daring and courageous that makes you feel alive and enables you to be who you want to be. Who knows, along with the way you might become an inspiration for someone else too!

Whose entrepreneurial story inspired you the most? Let us know in the comments below!


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