5 Unlikely Entrepreneurs and What You Can Learn From Them

Want a heads up when a new story drops? Subscribe here

Quite often, when you are first discovering an entrepreneur’s back-story, you realize they have been hustling since they were a child. Perhaps he started a lemonade stand when he was just five years old, and he never looked back. Maybe she was a child prodigy in science or mathematics, who everyone simply knew would be successful. These are the natural-born entrepreneurs, the types that were seemingly born to make it big in the world of business.

But once in a while, along comes an “unlikely” or surprising entrepreneur. These are the entrepreneurs nobody saw coming, yet they appear on the scene with the charm, instincts, wit and smarts to take the business world by storm.

Does this sound like you? Here is what you can learn from the “unlikely” entrepreneurs.

Sophia Amoruso

Sophia Amoruso is the 30-year-old founder of Nasty Gal, a California-based, (mostly) online retailer that sells clothes to “fashion-forward, free-thinking girls.”

Sophia AmorusoNow, if you haven’t heard of Nasty Gal, you are probably conjuring up images of young women in flirty dresses and killer heels, and you’re not far off the mark. But what you might not realize is that within eight years of its launch in 2006, Nasty Gal was, according to Amoruso’s first book #GIRLBOSS, a “$100-million-plus business with a fifty-thousand-square-foot office in Los Angeles, a distribution and fulfillment center in Kentucky, and three hundred and fifty employees.”

These are impressive numbers, right?

Here’s the kicker: When Amoruso launched Nasty Gal in 2006 it was essentially on a whim.

To cut a long story very short, Amoruso was recouping from a minor health issue when she discovered a number of eBay sellers who were hawking vintage clothing. As she writes in #GIRLBOSS, she thought: “Hell, I can do that! I had the photography experience. I had cute friends to model. I wore exclusively vintage and knew the ropes. And I was an expert scavenger.”

Soon after, Nasty Gal launched.

So, why is Amoruso an “unlikely” entrepreneur? Put it this way: How often does a company skyrocket to a top 20 spot on the Inc. 500 list with a CEO at the helm that has just a few minimum wage jobs under her belt, and absolutely no business experience to speak of? Answer: almost never. Here’s how Amoruso made it happen.

She took pride in her work: In #GIRLBOSS, Amoruso discusses the one-woman assembly line she set up when Nasty Gal was still a fledgling store, and Amoruso was everything: stylist, photographer, copywriter, marketer, mail clerk. While others might have cut corners, sacrificing aesthetics for the sake of efficiency, Amoruso’s pride would not allow her to do so. She recalls carefully affixing shipping labels to packages, prudently inspecting each product before shipping it out, and ensuring each model is styled to perfection. These seemingly small details certainly took extra time out of Amoruso’s already hectic schedule, but when you compound small wins, you get big results. The upshot? Amoruso’s customers could clearly see she cared about her business, her product and her customers.

She hustled: A few years after launching Nasty Gal, Amoruso wanted to start selling modern clothing alongside her vintage wares. She headed to a trade show, approached a brand she knew she wanted to work with and was told no. Reeling from the rejection and refusing to take no for an answer, Amoruso showed the designer her website. He signed up, and others soon followed. The lesson learned? As an entrepreneur, you have to believe truly that “no” isn’t an option. If Amoruso had walked away, Nasty Gal most likely wouldn’t be where it is today.

She understood her strengths: Recently, Amoruso stepped down as the CEO of Nasty Gal and appointed someone who could take Nasty Gal to the next level while Amoruso spends time in her new role as executive chairman connecting with the company’s customers. Only a wise entrepreneur knows when to stay and when to step aside, but Amoruso knows her strengths and weaknesses, and how to use them to her company’s advantage.

Pete Cashmore

Pete Cashmore is the 29-year-old founder of Mashable, a news and information website primarily aimed at the “connected generation.”

Pete CashmoreSince its inception in 2005, Mashable has been at the forefront of social media and technology news, although it has extended its coverage to include other topics including business, entertainment, world news and lifestyle. With more than 42 million unique visitors and 7.5 million shares a month, not to mention more than 20 million combined followers on social media, there is no doubt Mashable is a beast in the tech world.

Was it always this way? Short answer: no.

When a website is putting up numbers like these, it is easy to imagine it had not-so-humble beginnings. Say, a team of Silicon Valley tech giants coming together with a vision of creating a juggernaut website. Instead, Cashmore was the sole founder of Mashable, and he launched the website from his bedroom in his parents’ house in Aberdeenshire, Scotland. That fact alone makes Cashmore an “unlikely” entrepreneur, but here is how he made it work.

He faked it until he made it: In Mashable’s early days, Cashmore realized that in order to play with the big boys, he had to act like one of them. The problem was, as he once told Entrepreneur.com, “Not only did I not have connections, I wasn’t in [Silicon] Valley.” So, Cashmore used the fact he could hide behind his computer screen to his advantage. He began keeping American working hours, sleeping during the day so that he could be at his computer when America kicked into gear each day. Further, he cranked out the same amount of content a small team could produce, at times penning more than ten articles a day. If you didn’t know Pete Cashmore was a 19-year-old blogger in Scotland, you wouldn’t know.

He educated himself: Much of Cashmore’s teenage years were spent in and out of hospital after appendectomy surgery left him with complications. To keep occupied, Cashmore turned to the Internet, and he soon became intrigued by the number of blogs and social networking sites popping up. Interestingly, instead of just jumping in and getting involved, Cashmore decided to read up on the industry, subscribing to business blogs and tech blogs, and reading books of the same nature. These resources became the foundation of his knowledge and gave him the necessary preparedness to enter the tech world.

Oprah Winfrey

Oprah Winfrey needs no introduction.

Oprah WinfreyIn 1984, Winfrey moved to Chicago to host the morning talk show A.M. Chicago. Within a month, the show had skyrocketed in the ratings to become the number one local talk show. Less than a year after she began, the show was renamed The Oprah Winfrey Show, and in 1986, the show entered national syndication, quickly becoming the highest rated talk show in history.

Outlining the full extent of Winfrey’s accolades goes far beyond the scope of this article, but here’s a quick summary: Winfrey’s 1993 interview with Michael Jackson is said to be the most watched television interview in history; her magazine, O, the Oprah Magazine, was named by Fortune as the most successful start-up ever in the industry; and she has won seven Daytime Emmy awards, as well as been nominated for Oscars, Tonys, Primetime Emmys and more.

On a personal level, Winfrey is the first black female billionaire in history.

To say Winfrey is successful is an understatement, but when you factor in the formidable odds Winfrey overcame, her story is all the more inspiring. Winfrey was born to an unwed teenage housemaid and spent several of her childhood years being shuffled between her mother, her grandmother and her father. She was sexually molested as a child and ran away from home as a teenager. Soon after, she fell pregnant; the child died shortly after birth. Eventually, she moved to Tennessee to live with her father, and she became an honors student.

To prosper after overcoming a tragic past is one thing; to become one of the most successful and richest people in the world is quite another, which is why Winfrey is an “unlikely” entrepreneur. Here’s how Winfrey made it happen.

She knew no boundaries: Winfrey’s popularity as a talk-show host was thanks in part to her friendly approach to her viewers. There was no disconnect between the audience and Winfrey; instead, The Oprah Winfrey Show often felt like a living room full of friends talking through their issues. Winfrey spoke from the heart, revealing her personal anecdotes when necessary. Additionally, Winfrey regularly discussed formerly taboo subjects and is credited with bringing certain discussions into the mainstream.

She never stops: Suffice to say that when you reach Winfrey’s level of wealth, you no longer need to work. But Winfrey, despite being one of the world’s richest women, has never stopped and believes her ultimate purpose in life is to teach. In a 2011 issue of O, Winfrey wrote: “Do what you’ve always wanted to do. Stop pretending you’re anything other than what you are. As Maya Angelou says, ‘When you learn, teach.’ ” Winfrey’s belief that we should all have a purpose in life is powerful, and is no doubt part of what has driven her ambition, and in turn her career.

Richard Branson

Richard Branson is certainly a household name. The 64-year-old is the charming, iconic founder of the Virgin Group, not to mention one of the world’s richest citizens.

Richard BransonBranson grew up in Blackheath, London.

At 16 years of age, Branson dropped out of school to found a student magazine, funnily enough. It was immediately a success, complete with corporate advertisers and interviews with celebrities – Mick Jagger was an early interviewee – intellectuals and politicians alike. On the back of his magazine’s success, Branson began trading records and eventually started his own record store in London. Despite a few legal glitches along the way, Branson continued on with his entrepreneurial endeavors, including founding his record label Virgin Records in 1972.

The rest, as they say, is history. Virgin Atlantic Airways followed in the early 1980s; Virgin Mobile in the late 1990s; and in the early 2000s, Branson announced a new space tourism company Virgin Galactic. These endeavors alone would be inspiring, but along the way Branson has also acquired, launched, sold and shut down hundreds of companies and ventures.
When you add up success after success, it seems unreasonable to suggest Branson is an “unlikely” entrepreneur. But here’s the catch: While his childhood could be considered uneventful compared to, say, Oprah Winfrey’s, Branson did struggle with dyslexia and a poor academic record. In fact, the headmaster of his school sent him off with parting words for the ages, telling him he would either end up in prison or a millionaire. So, how did he do it?

He is loved: Branson has charisma in spades, but it is his leadership skills that have people talking. Branson has always made it a point to treat his employees – and there are thousands of them –just as he would family members. In an article Branson wrote for Entrepreneur.com, he says: “People flourish if they’re praised. Usually they don’t need to be told when they’ve done wrong because most of the time they know it. If somebody is not working out, don’t automatically throw him or her out of the company. A company should genuinely be a family. So see if there’s another job within the company that suits them better. On most occasions you’ll find something for every single kind of personality.”

He takes risks: Branson has often said he will try anything once. This credo has served him well and aligns perfectly with another oft-repeated entrepreneurial motto: fail fast. Granted, Branson’s willingness to take risks might seem flippant to the untrained eye, given he has billions to fall back on, but Branson has been taking risks from the get-go. Case in point: In the early 1990s when he needed to keep his airline afloat, he sold his record company, his original moneymaker. Throwing caution to the wind might not come naturally to everyone, but as Branson says: “If a businessperson sets out to make a real difference to other people’s lives, and achieves that, he or she will be able to pay the bills and have a successful business to boot.”

J.K. Rowling

While the name J.K. Rowling might not ring a bell with everyone, her creation – Harry Potter – no doubt will. Yes, Rowling is the author of the super-successful Harry Potter series of books.

J.K. RowlingAs the story goes, Rowling conceived the idea for the Harry Potter series way back in 1990. The first book wouldn’t be published for another seven years, but it was a quick success. Five months after publication, the book won its first award. In the ten years that followed, Rowling released six more Harry Potter books, won numerous awards, and became one of the richest people in the world, not to mention the second-richest female entertainer in the world.

Of course, the road to success – especially success of this kind – isn’t typically paved in gold. On the contrary; in the seven years between conceiving of the Harry Potter story and publishing the first book, Rowling’s mother died after a long battle with multiple sclerosis, she got married, she gave birth to her first daughter, and she subsequently found herself a single mother when she and her husband divorced. These years were spent in “abject poverty,” with Rowling once stating that at times she was “literally choosing between food and a typewriter ribbon.”

So, how did Rowling turn her fortunes around and consequently become one of the most successful entrepreneurs of all time, despite the troubles that had befallen her?

She embraced her failures: Rather than drown her sorrows or dwell on her troubles, Rowling embraced them. After all, she had already hit rock bottom in her mind, so there was no other way but up. With that mindset, she set out to write her book. When she spoke to Harvard’s graduating class in 2008, she had this to say about the importance of failure: “It is impossible to live without failing at something, unless you live so cautiously that you might as well have not lived at all, in which case you fail by default.”

She never gave up: Despite being diagnosed with clinical depression and contemplating suicide, Rowling used her writing to struggle through. She signed up for welfare benefits and spent her days writing Harry Potter in cafés around Edinburgh while her daughter Jessica slept beside her. Life as a single mother on welfare could not have been easy, but Rowling clearly had the drive and determination an entrepreneur needs to be successful. Without it, one can only imagine the next turns Rowling’s life would have taken.


Don’t miss a beat.

Subscribe now