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From a Night in Jail to A Galactic Empire: How Richard Branson Grew His Career as a Serial Entrepreneur

Anisha Sagar

When Richard Branson dropped out of school aged 16, the then headteacher of Stowe School, Bob Drayson, told him, “I predict you will either go to prison or become a millionaire.” Bob was half right, right. Richard managed both.

In 1971, after getting caught evading purchase tax on vinyl records (falsely declared as export stock), 20-year-old record store owner Richard Branson spent a life-changing night in jail. Fifty years later, the 71-year-old billionaire travelled to space in a suborbital test flight for his company Virgin Galactic.


Reaching For The Stars (And Falling Short)

It’s a story to inspire anyone with an entrepreneurial spirit who’s getting a steer on their very own business journey. But it’s not a story of rags to riches: Stowe is an English (fee-paying) public school, and Branson certainly didn’t grow up in a posh neighbourhood. No, this is the story of how you can overcome business failures through driving, daring, and empowering others, which lead to astronomical success (and wealth).

And Branson didn’t just fail once. It’s arguably the accumulation of multiple Virgin-branded business failures that made Branson the iconic and inspiring entrepreneur he is today. His track record is a testament to the adage that people fail most succeed. In his daughter Holly’s words, “The earlier we learn to embrace failure as a positive rather than a negative, the healthier and happier we’ll be.”

Trained actors learn to fall safely. Successful entrepreneurs learn to fail. It’s from taking those wrong turns and having to get back on track where the greatest lessons can be learned. In Branson’s case, he learned to pivot. Prior to setting up his ill-fated discount record business, he’d left school to start his first business: ‘Student’ magazine. While it secured high-profile interviews, it struggled with cash flow, causing Branson to pivot to selling records.

Of course, selling records was just the start. Later, in the 1970s, he pivoted to recording and releasing music through Virgin Records. Building a successful back catalogue of releases – from Mike Oldfield to the Sex Pistols – the company eventually sold for a billion dollars in 1992.

So, while Branson’s businesses have come and gone, one thing has remained the same: his drive to keep going. With the simple philosophy of starting small and thinking big, anything is possible – if you’re always thinking about what might be next, how you can expand, and how to take your idea to the world. And if it’s not working out. Pivot.

Daring To Do Things Differently

Branson has always dared to be different, from his record-breaking hot air balloon crossing of the Pacific to his fastest ever crossing from Dover to Calais in an aquatic vehicle. He’s not afraid to be different. He prides himself on it. And Branson’s notoriety as a record-breaking daredevil feed into public perceptions of the Virgin empire.

Launched in 1994, the Virgin Cola brand was initially available on Virgin planes and in Virgin cinemas but was later released to the broader world. Initially successful in Europe, when the brand took on Coke and Pepsi in their home territory in the US, the company quickly went out of business.

Announcing Virgin Cola’s arrival in the US by driving a Sherman tank through a wall of their rivals’ cans in Times Square was an audacious marketing move. And while Virgin Cola won that battle, it lost out in the retail war, with rivals undercutting its prices and squeezing it out of the market.

It was a failure with a valuable lesson about branding your business. Whatever business you’re getting into, you need to be tangibly better than your competition. Your product needs to be unique. If it’s not, there’s no reason for a client or customer to choose you over a rival.

But being different doesn’t have to involve undertaking an elaborate world-record breaking challenge, or a promotional stunt like shaving off your beard, and dressing up in a bridal gown for your latest venture into bridal wear stores.

Being different means setting your brand apart from your competitors. In the Internet age, that can be done cost-effectively through informed brand design, a professional website, and the right marketing communication via your social media channels.


Find Out How To Sell On Social Media In The UAE

Empowering Others Around You

The Virgin Group has a people-first approach to its workforce. Rather than expecting new employees to fit into a predetermined type, they look for people who will add to their culture. Promoting itself as an inclusive workplace, the Virgin Group’s philosophy is simple yet effective: if you take care of your employees, they’ll take care of your business.

Employee well-being sits right at the heart of the best companies and organisations. Leaders who look for the best in others create a culture of positive feedback. And by building confidence in others, they feel empowered to suggest improvements, which drives better services and employee satisfaction. Additionally, involvement in running the organisation generates a feeling of collective ownership.

Branson also gives back to the local business community with the likes of the Virgin Startup organisation, which provides British entrepreneurs with loans, mentoring programs, and support systems. This dramatically affects his reputation and the loyalty of those around him.

Whether you’re a single-person start-up or an established business looking to expand, positioning yourself as a company that cares can have significant benefits down the line. Because one day, the people you interact with could be future business partners, competitors, or customers.

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No Reward Without Risk

Ultimately, as typified by Branson, commercial success is a heady mix of taking risks and knowing when to walk away, celebrating wins, and not being afraid of failure.

At the end of the day, one takeaway is clear in analysing the business greats of our time: They were all bold – and we know that fortune favours the bold. So, if you’re looking for significant results, you will have to go all in.

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