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The surprising attributes shared by the world’s top entrepreneurs

The world’s most successful startup entrepreneurs and corporate disrupters share some surprising attributes that help to explain why their seemingly crazy ideas found traction.

Qualities of an entrepreneur

When Manyasiri ‘Pear’ Chotbunwong reached 15, her periods suddenly stopped. Confused and increasingly worried, the Thai schoolgirl was too ashamed to confide in her parents or a trusted teacher as deep-seated cultural taboos meant the subject of menstruation was strictly off-limits.

Instead, she suffered silently for months, becoming more and more terrified that something was seriously wrong. Eventually, she summoned the courage to talk to her mother, and, soon afterward, was diagnosed with polycystic ovary syndrome, a treatable condition that affects around 10 percent of young women.

When Chotbunwong realized that many of her friends had also been too embarrassed to seek help, she vowed to do something about it.

Her extraordinary achievements over the last three years have done more to transform attitudes and encourage debate than any public information campaign could ever have achieved. Not only that, her actions form a textbook guide to the skills and attributes needed to be a successful disruptive startup entrepreneur.

“I had no idea what to do, but I felt raw human emotion setting a fire. It’s possible to create change, even if you have no experience.” – Manyasiri ‘Pear’ Chotbunwong

In fact, any business looking to scale up, pivot or innovate can learn valuable lessons from the Bangkok crusader, who’s still only 18 and has won major international awards for her work.

“What motivated me was my passion about destigmatizing menstruation,” she tells The CEO Magazine. “It was very personal to me as I’d experienced the isolation firsthand.

“I had no idea what to do, but I felt raw human emotion setting a fire. It’s possible to create change, even if you have no experience.”

Before we get to Chotbunwong’s groundbreaking work, it’s worth considering the five characteristics shared by the most impressive disruptive startups, according to Faster Capital:

  1. Their new idea is better than anything currently available.
  2. Their business strategy is unique.
  3. Innovative technology gives them a competitive edge.
  4. The market they target has potential for growth.
  5. They’re led by passionate and determined individuals.

A revolutionary HERstory

Qualities of an entrepreneur

Chotbunwong’s first step was forming an organization called HER to openly discuss periods and challenge cultural disinformation.

The topic was considered so distasteful that many teenagers were too afraid to ask for sanitary products, while female prisoners were denied them completely, often forced to mop up their own blood.

During weeks spent researching, she discovered that reusable pads could be manufactured from a sugarcane byproduct. She had her revolutionary idea, but it needed to be affordable.

Her solution was to pay those humiliated former prisoners, themselves shunned by Thai society after their release, to manufacture them at scale. Innovative technology and a unique strategy.

“As a disrupter, I have to instill my own inner strength in others to give them the courage to stand up for something bigger than any individual.” – Manyasiri ‘Pear’ Chotbunwong

Soon her student network exceeded 12,000, including many in the United States, and was distributing them not only across Thailand but to five other countries. The potential for growth appeared unlimited.

“There’s a risk in challenging mainstream views, and no safety net to fall back on,” she reflects. “But when I face harsh criticism, what keeps me going is the belief that my voice will be loud enough to shift mindsets and amplify the voices of others.

“As a disrupter, I have to instill my own inner strength in others to give them the courage to stand up for something bigger than any individual.”

Risky business

Qualities of an entrepreneur

Such courage and determination were also evident in the most successful industry disrupters of the last decade, according to award-winning author Pascal Dennis, Founder of Lean Pathways, a leading business consultancy.

He argues that each displayed an inherently high tolerance for risk and abnormally strong self-belief.

“Most innovations fail, no matter how well planned, but the entrepreneur doesn’t see blockers, only countermeasures,” he tells The CEO Magazine.

Before he launched his business 23 years ago, he was a well-paid senior engineer, but such a leap of faith didn’t faze him.

“Everybody tried to talk me out of it, but I didn’t see risk, only opportunity. And when I got some traction, people said, ‘Well, of course,’” he explains.

“In hindsight, it all made sense, but in the first few years, all the signs were negative. Had I felt risk as intently as ‘normal’ people, could I have stuck with it through all the failure?”

“Most innovations fail, no matter how well planned, but the entrepreneur doesn’t see blockers, only countermeasures.” – Pascal Dennis

But having the guts to bet the farm on a crazy, left-field whim is only the beginning of the journey to riches. To stay the course, you need two further and very rare qualities, says Charlene Li, author of The Disruption Mindset, who has advised half the Dow Jones Industrial 30 companies on rule-breaking, transformational leadership.

“The first is realizing that no idea is ever complete at the outset,” she tells The CEO Magazine.

“It requires refinement, adaption and constant revamping. What’s unique about disruptive leaders is they look to future customers for insight, not current ones. And the further out they look, the more disruptive they are.”

The second attribute corporate iconoclasts have in common is juggling raw ambition with stark reality.

“They don’t settle for merely being good enough, but nor do they aim for perfection,” she says. “Balancing a push for change and respect for the established order can be difficult.”

Li cites Paul LeBlanc, President of Southern New Hampshire University (SNHU), as the best example of a disrupter.

When he was appointed in 2003 it was a small, private university with 2,800 students. Today, there are more than 160,000 online learners and it’s the largest not-for-profit, accredited online education provider in the world.

“What right does a tiny university have to do this, versus a Harvard or MIT? Paul made the student experience the centerpiece of SNHU’s strategy, and disrupted how universities think about higher education at scale.”

Li also cautions against the dangers of unbridled self-belief. “Your top priority should be investing in your people and creating a great culture. If you don’t, you’re counting on your personal brilliance, which is miniscule compared to the power of an entire team.”

Succeeding in failure

Qualities of an entrepreneur

Business failure, however, isn’t always such a bad thing for a wannabe disrupter, even when it is caused by an overinflated ego.

In some ways, a startup needs to nearly go kaput to find its true path. Defying convention requires some major leaps of faith, and more lessons can be learnt from an unseemly flop than a modest victory.

It’s why venture capitalists look for the hockey stick revenue graph, as early struggles are a sign of a robust launch strategy.

And there’s nothing new about early stumbles being a prerequisite for success. Among the startup entrepreneurs who recovered from bankruptcy are Walt Disney, Henry Ford, Henry Heinz, PT Barnum and, er, Donald Trump.

Elon Musk said as much about Tesla’s troubled beginnings.

“I thought we’d most likely fail,” he recalled, but this didn’t stop him. “If something is important enough, you should try – even if the probable outcome is failure.”

Airbnb is the poster child for subversive insurgency, but it too faced oblivion in 2009, with revenue stuck at US$200 per week and the credit cards of both founders maxed out.

The eureka moment was realizing that the grainy, dimly lit photos of the accommodations on its site weren’t exactly inviting. Once that was addressed, they proceeded to change the world, one hotel room at a time.

Even when confronted with ridiculously daunting odds, they believed in their big idea and chipped away until it worked.

“Your top priority should be investing in your people and creating a great culture. If you don’t, you’re counting on your personal brilliance, which is miniscule compared to the power of an entire team.” – Charlene Li

“Those people who are crazy enough to think they can change the world are the ones who actually do,” Steve Jobs once said.

When he returned to Apple in 1997, having been ousted 12 years earlier, the company’s annual loss was US$1 billion and it was 90 days from oblivion. Dwarfed by HP and Dell, it had the feel of a startup with Jobs in full cornered renegade mode.

Few thought it could survive, but the mercurial maverick in chief turned it around by asking a key question: “Who is Apple and where do we fit in this world?”

Soon ‘think different’ had been born, and Jobs kept his foot firmly on the innovation throttle, practically writing the disrupter playbook along the way.

Key to his philosophy was that invention always trumps improvement, a theme articulated by Paypal Co-Founder Peter Thiel in his influential book Zero to One.

Each business revolution, he claims, only happens once –  the next Mark Zuckerberg won’t start a social network and the next Larry Page won’t develop a search engine. So it’s OK for a startup leader to mimic their mindsets and exploratory flair, but attempting to copy them will end in tears.

Give ’em what they don’t want!

Attributes of an entrepreneur

It follows, therefore, that global domination is far more likely if you have a product that no-one wants. Or rather, one that no-one realizes they want.

Before Uber, everyone was pretty happy with taxis, and no-one was protesting in the streets demanding a social network until Zuckerberg rocked up.

The same is true of Amazon, Netflix, SpaceX, Spotify, TikTok, Alibaba and plenty more. Before 2021, no-one had heard of Wordle, but the following year it became the planet’s top Google search term.

Selling mattresses online was the unlikely business idea that propelled Casper from a debt-ridden startup in 2014 into a billion dollar business within five years. Until they arrived, mattresses were sold from warehouses and strapped to the roofs of cars to get them home.

No wonder its early investors weren’t exactly in bed with the idea of squashing a foam mattress into a three-foot tall cardboard box and shipping it interstate from Georgia.

“At the beginning, we met with dozens of investors who all said: ‘No-one is ever going to buy a mattress online – it’s a dumb idea, do not do it!’,” Co-Founder Neil Parikh told CNBC.

“We may never know when the ‘right time’ is, or when a life-changing opportunity will come our way.” – Manyasiri ‘Pear’ Chotbunwong

What sent their business into dreamland was Kylie Jenner raving about her purchase on Instagram, garnering an astonishing 870,000 likes. It was a very lucky break, given that the reality colossus pockets an estimated US$1.8 million for such posts today.

Venture capitalists also thought financial trading app Robinhood was a spectacularly dumb idea when it set out its stall in 2013; its only unique selling point the fact it wouldn’t make as much money as its rivals.

Founders and Stanford University buddies Vlad Tenev and Baiju Bhatt had a vision of opening up stock markets to the masses by hosting them on a mobile platform and waiving brokerage commissions, begging the question of how they’d ever turn a profit.

Quite easily, as it turned out. Through margin lending, receiving payments for order flow and the interest on its mostly-Millennial clients’ deposits, it took Robinhood less than a decade to amass US$78 billion in managed assets and more than US$1 billion in annual income from its 23 million customers.

Reliance on order flow, often described as ‘kickbacks’, arguably makes the firm less altruistic than its medieval folklore namesake, but it did revolutionize access to share markets, and herald a new era of feeless trading.

Other people’s money

Attributes of an entrepreneur

Of course, taking a risk with you own money – or even that of a private equity backer – is very different to risking your company’s money. Just ask Nick Leeson, whose disruptive entrepreneurism effortlessly navigated the ‘failure’ stage by bringing down Barings Bank, but didn’t quite manage the scaling up bit.

What should a middle manager with a crazy idea to shatter the status quo do if his boss isn’t keen on risking his pension plan?

“Employers want you to conform, but your role models are rule breakers,” says Andy Binns, author of Corporate Explorer: How Corporations Beat Startups at the Innovation Game. “What should you do – play it safe? Nobody wants an employee who’s reckless or unethical.”

He outlines six steps workplace rebel rousers can take to launch a startup from within.

  • Focus on customers: Corporations are far more likely to take a punt on a radical new venture if they can see it working in the real world.
  • Set your sights high: Small ideas may be less risky, but they’re insignificant. Aim to solve a problem that’ll make a huge difference.
  • Inspire people: It’s not enough that you know it’s a brilliant idea, you have to passionately articulate your vision to the people that matter.
  • Build momentum: The powers that be are more likely to greenlight a project that has the backing of key people within the organization, not just a hair-brained loner.
  • Don’t make it about you: Yes, Jobs, Musk, Bezos et al. unleashed their mighty egos, but blatant attention seeking isn’t an attractive trait and won’t help your case.
  • Don’t politely wait: Effective outliers proactively agitate for change and push hard to get their ideas accepted. If they didn’t, no-one else would.

“Rebels shouldn’t expect to be popular with everyone,” Binns told Fast Company. “What matters is the quality of your commitment to your purpose and willingness to stand out from the crowd.”

When Chotbunwong decided to try and ease the trauma associated with menstruation for young girls at her school, she wasn’t setting out to make seismic changes to Thai culture.

That she did so was down to the basics of disruptive entrepreneurism – passion, originality, innovation and sheer single-minded determination. And the courage of her convictions.

“We may never know when the ‘right time’ is, or when a life-changing opportunity will come our way,” she says. “The only thing we can do is put our best foot forward and make the change we want to see happen.

“We won’t know how far our message will go, or what our impact will be, but as long as we never forget why we started out, I truly believe people will recognize what’s in our heart and we’ll be able to make our mark in the world.”

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