What word would you use to describe an entrepreneur? Rebellious, maverick, eccentric or anarchistic? Damn right, we’d use all of them too. Over the last decade, we’ve seen innovators, rebels and creators reshape the professional landscape. Whether they’re disrupting an industry or marketing themselves in a new and unique way, today’s rebellious entrepreneurs are the definition of unconventional; they are challenging traditional wisdoms and succeeding through being different and original. If you want to learn from the most innovative and disruptive minds in business today, you must read and learn how the rebels challenging the status quo make their own rules:

  1. Sophia Amoruso – Founder and CEO of Nasty Gal1 Sophia

“It’s true: in about eight years, I went from a broke, anarchist “freegan” dead set on smashing the system, to a millionaire businesswoman…”

Since first setting up an eBay shop called Nasty Gal Vintage in 2006 after getting a hernia, Sophia Amoruso has, in the words of her book #GirlBoss, ‘gone from high-school dropout to founder and Executive Chairman of Nasty Gal, one of the fastest-growing retailers in the world.’

Starting out with a passion for vintage clothes, an eBay account and a MySpace profile, Sophia Amoruso is the embodiment of a rebellious entrepreneur. Named in Inc.com’s 2013 30 Under 30, in just the first five years, Nasty Gal had grown from a one-woman online shop, to an online retail powerhouse with a dedicated following and revenue upward of one hundred million dollars.

“A #GirlBoss is someone who’s in charge of her own life. She gets what she wants because she works for it… You’re a fighter – you know when to take the punches and when to roll with them. Sometimes you break the rules, sometimes you follow them, but always on your own terms… You’re going to take over the world, and change it in the process.”


2. Banksy – Artist, Activist, Director2 Banksy

“Think outside the box, collapse the box, and take a fucking sharp knife to it.”

How often do you come across an entrepreneur with a hidden identity who’s immediately familiar – other than maybe Bruce Wayne? Challenging the way we view and consider the world around us, Banksy is a graffiti artist, political activist and film director whose work is a rebellious social commentary on all angles – from its subject matter, to its message and even its physical format.

From street art to films, books, The Simpsons title credits and installments such as Dismaland, Banksy’s work draws a satirical focus to the state of current affairs. It often brings attention and new perspectives to difficult issues such as war, religion and recently and the refugee crisis in a rebellious, unignorable and instantly recognisable way.

“Imagine a city where graffiti wasn’t illegal, a city where everybody could draw whatever they liked. Where every street was awash with a million colours and little phrases. Where standing at a bus stop was never boring. A city that felt like a party where everyone was invited, not just the estate agents and barons of big business. Imagine a city like that and stop leaning against the wall – it’s wet.”


3. Jack White – Musician, Record Producer, Founder of Third Man Records3. Jack White

“There aren’t that many things left that haven’t already been done, especially with music. I’m interested in ideas that can shake us all up.”

Musician, singer, songwriter, producer, former upholsterer, founder of independent record label Third Man Records and co-owner of streaming service Tidal, Jack White famed as being one of the music industry’s busiest men.

Most people will be aware of Jack as half of the White Stripes, but in the midst of the band’s success, Jack was simultaneously founding Third Man Records, conducting projects with The Raconteurs, The Dead Weather and continuing his own solo career. Operating successfully outside of the ‘major label’ model, Jack White is a rebellious leader who makes the most of the ways the music and creative industries are evolving. This is especially well summarised on the Third Man ‘about’’ page, which reads: ‘Third Man is an innovator in the world of vinyl records and a boundary pusher in the world of recorded music, aiming to bring tangibility and spontaneity back into the record business.’

“I gave myself over to music and art a long time ago, so I don’t get to relax and I don’t get to sit still. The best I can do is constantly create my own environment so it benefits what I need to accomplish in the next step.”


4. James Watt – Co-Founder of BrewDog4. James Watt

“I just wanted to outline our off-the-wall, slightly anarchic approach to business so other people could see what we’ve done and realise that you don’t have to do what you’re supposed to do, you don’t have to follow the status quo, and you can do things on your own terms,”

Fed up with industrially brewed lager dominating the UK beer market in 2007, James Watt co-founded craft beer company BrewDog aged 24, alongside Martin Dickie and their dog. BrewDog has combined a passion for great craft beer with a punk attitude from day 1. Both founders have driven a tank through Camden and projected nude images of themselves on the Houses of Parliament. In only their second year of operation, BrewDog became the second largest independent brewery in Scotland. By 2009 it was the UK’s fastest growing alternative beer brand.

Turning conventional business models upside down, BrewDog is owned by thousands of shareholders – who can apply to support the brand through their Equity for Punks programme. As of 2015, this rebellious model is the largest equity crowdfunding scheme in history – with over 32,000 shareholders.

“Before I set up the business I was captain of a fishing boat. I’d never done a business before, I’d never been involved in business. We didn’t know how things were meant to be done so we went ahead and did things on our own terms, in our own way, and almost inadvertently created a whole new approach to business along the way.”


5. Oliver Sykes – Bring Me the Horizon Lead Vocalist, Founder of Drop Dead Clothing5. Olly Sykes

“I really wanted to do something for myself and that was when I started the band and Drop Dead. I was always drawing and scribbling, and even before I dropped out [of school] I wanted to just get a job. But my mum said, ‘Why don’t you try doing something for yourself? I don’t mind lending you a bit of money, and I’d rather see you doing what you want to do instead of what everyone else does.’ I was trying to think of more regular ideas that might make a business work, something mundane, and there were no underground clothing labels back then in England. I wanted to just try something.”

Forming Bring Me the Horizon in 2003 while he was still in school and apparel company Drop Dead Clothing in 2005, Oliver ‘Oli’ Sykes shows how creativity is a true entrepreneurial asset.

Oli balances an ongoing career with Bring Me the Horizon alongside Drop Dead. Whether he’s breaking away from traditional approaches, selling live or mail-order merchandising or leading the band’s controversial image, rebellion and difference are found throughout Sykes’ career. Most recently he smashed Chris Martin’s table at the 2016 NME’s and we know it won’t stop there! He’s worth over £3m.

“It was like a blur. As soon as [Drop Dead] started it did well in my eyes… and at some point it just jumped up for some reason. When it started spreading out with other bands I couldn’t control it, so I handed it over to my mum… she took hold of it while we were touring. Every day I used to go back to the post office with 30 packages and it got to the point where I couldn’t fit it into a bag.”


6. Travis Kalanick – CEO and Co-Founder of Uber6. Travis

“Stand by your principles and be comfortable with confrontation. So few people are, so when the people with the red tape come, it becomes a negotiation.”

Previously founding peer-to-peer file sharing companies Scour and Red Swoosh, Travis Kalanick founded the online transportation network Uber alongside Garrett Camp in 2009. Today Uber operates across c.58 countries and upward of 300 cities globally. In 2014, Travis Kalanick was listed on Forbes ‘400 Richest Americans’ with an estimated net worth of $6 billion. Business Insider attributes his success to his “relentlessness, competitive spirit, and unwillingness to negotiate”.

Neither Uber or Kalanick are strangers to controversy. Relentless and competitive, Kalanick has faced challenges such as bankruptcy and lawsuits in his previous businesses whilst Uber faces ongoing disputes globally, often from government, over regulation, safety and legality.

“I’m a passionate entrepreneur. I’m like fire and brimstone sometimes. And so there are times when I’ll go—I’ll get too into the weeds and too into the debate, because I’m so passionate about it.”


7. Steve Bartlett – CEO of Social Chain7. Steve Bartlett

“There’s a pivotal point where sane people will give up because it makes sense to. I had no money, I had no food and nothing was going right… I had a meeting in London that cost me £8 to get there and at this point I had scraped together £8 but no more.  I arrived, had the meeting (which went well) and had no way of getting home – my phone had been cut off so I couldn’t even call anyone. I slept on a bench, woke up and walked to Kingston to my sister’s house who gave me money to get home.”

Difference and perseverance define Steve Bartlett, CEO of Europe’s largest influencer marketing agency, Social Chain. After dropping out of university to create student community Wallpark, Steve came across Dominic McGregor who at the time owned the popular Twitter page ‘Student Problems’. Together the two founded Social Chain.

With an average age of 21 across the company, Social Chain doesn’t follow traditional marketing rules. It’s disruptive and different, with success based on owning hundreds of popular social accounts, and promoting brands through them. As BuzzFeed explored; “It only takes 26 minutes for the staff of Social Chain to push #YouKnowYoureBritishWhen to the top of Twitter’s UK-wide trending list. By the time the hashtag dies down a few hours later, it will have appeared in nearly 40,000 tweets.”


8. Casey Neistat – Director, Vlogger, Co-Founder of Beme8. Casey

“More often than not, I’ll find myself in situations where I have no idea what I’m doing, and I feel no shame in revealing that.”

From his YouTube videos and daily vlogs, to his HBO series ‘The Neistat Brothers’, director and filmmaker Casey Neistat has made the most of this decade’s shifts in technology to access and build his audience and find success.

Neistat has been making short films since the early 2000’s; originally gaining exposure for his three-minute film about the iPod’s lack of a battery replacement programme; ‘iPod’s Dirty Secret’. Since opening his YouTube account in February 2010, Casey has created over 740 videos, daily vlogs and has 2.5 million channel subscribers. Casey is also co-founder of video sharing app Beme, which launched in July 2015. In the first eight days after Beme’s release alone, users had shared over 1.1 million videos using the app.

“If you’re doing what everyone else if doing, you’re doing it wrong.”


9. Sarah Wood – Co-founder and Co-CEO of Unruly Media9. Sarah Wood

“If you’re working in a high-growth tech company, with new products, features and markets constantly coming on stream, there’ll be plenty of moments when you feel out of your depth. That’s not a problem – as long as you’re prepared to ask questions and seek the help you need.”

Over the last decade, Sarah Wood has grown her tech company from a three-person start-up, into a $43m business, which was acquired by News Corp in 2015. Sarah has been voted UK Female Entrepreneur of the Year at the Growing Business Awards, one of 15 Women to Watch in Tech by Inc.com and one of 10 London-Based Entrepreneurs to Watch by Forbes. Her mission with Unruly is to ‘deliver the most awesome social video campaigns on the planet’. To date, Unruly work with with 84% of Ad Age 100 brands and share video content to 1.27 billion users.

“My tip would be to do what’s right for you, and make sure you have a support network in place. That’s really crucial.”


10. Alexander (Solly) Solomou – CEO of the Lad Bible Group10. Solly

24 year old Alexander (Solly) Solomou is the man behind the growth of controversial brand ‘The Lad Bible’. In 2012 Solly transformed the company into a multifaceted media supergiant comprised of The Lad Bible Ltd, The Sport Bible Ltd and The Sport Bible.

With the company making more than £100,000 revenue in a typical month and upward of £1 million a year from advertising, Solly has moved The Lad Bible’s image away from the controversial ‘lad culture’ image gained in its early years. With aspirations to become “the next IPC Media” with parent company 65twenty, Solly first got the idea for a digital media business while studying business management at Leeds University.


About The Author

Lucy Jones

Lucy Jones is a contributor for Rebelhead Entrepreneurs. Building a world out of written word, Lucy is a poet, artist, writer, and Head of Content at a UK based Digital Marketing Agency. She writes about entrepreneurial mindsets, philosophies, productivity and creative business observations. Admiring the disruptive mindset of America’s beat poets, literary rebels, and Gonzo journalists, Lucy has studied in America, travelled alone, written for Gap Year companies, and believes plans are guidelines to exactly what won’t happen - but that going off-route opens the door to the best opportunities. “When the going gets weird, the weird turn professional.” - Hunter S. Thompson

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