Running a business, regardless of size, is a demanding endeavour. And with the UK’s economic industry teetering on shaky ground, paired with the massive disruptions brought on by AI technologies, entrepreneurs will need grit and motivation more than ever.
If you’re a small business owner and are starting to feel like you’re fighting an uphill battle, here are 8 entrepreneurs you should look to for inspiration.
Sir Richard Branson (Virgin Group)
Any list of inspirational entrepreneurs won’t be complete without Sir Richard Branson. Unlike what some would believe, the London-born business magnate didn’t come from money. His mother was an air hostess, while his father was a barrister.
At 16, after dropping out of high school, Branson founded a magazine, Student. While their sales were modest, Branson still needed to cover a substantial portion of the production cost to get his business off the ground.
As a way to fund his magazine, Branson started a record shop, Virgin, in Oxford Street in 1971. Virgin’s success became his ticket to building Virgin Records one year later. Branson’s recording studio went on to become an enormous independent record label, signing famous bands and artists, including Mike Oldfield, Janet Jackson, The Sex Pistols, Spice Girls, and the Rolling Stones.
He has subsequently gone on to grow his Virgin empire with a conglomerate of businesses beating the ‘Virgin’ brand name in a diverse range of sectors from travel to telecommunications, health to banking and leisure.
Lord Alan Sugar (Amstrad)
While primarily recognised as the host of the BBC competition show, The Apprentice, any budding entrepreneur would know of Alan Sugar’s remarkable success story, founding Amstrad, the electronics company.
The Hackney-born businessman was the youngest of four children born to a humble tailor and clothing factory worker. He grew up in a council flat and worked at a grocery shop when he was a student. He even collected used bottles for money.
In 1986, Sugar founded Amstrad while working multiple jobs to support himself. He started selling electronic accessories, such as affordable hi-fi systems and stereo cassette players, out of the back of a cheap van.
From there, Sugar grew Amstrad to become one of the UK’s most recognisable electronics companies. The company was sold for £125 million in 2007, but Sugar, with his grandson, plans to revive it.
Oprah Winfrey (The Oprah Winfrey Show)
You likely heard of Winfrey’s story already. But for those who didn’t, you may just earn a lesson or two from hearing the Emmy Award-winning talk show host’s humble beginnings.
Before the billionaire and celebrated media personality we know and love, Oprah Gail Winfrey was born in an outlying town called Kosciusko in Mississippi. She was the daughter of a barber and a housekeeper.
In 1975, Winfrey dropped out of university and began her career as a local news anchor at a minor station in Nashville.
Her fearless choices, paired with her charisma on-screen, led to her founding her own production company, Harpo Productions, which produced the award-winning The Oprah Winfrey Show.
Remaining true to her roots, Winfrey kept a family-friendly approach even as most talk shows underwent a massive shift toward a harsher tone. The audience loved her for it, and Winfrey found remarkable success in the industry.
Mark Cuban (Dallas Mavericks)
Looking at the owner of the NBA’s Dallas Mavericks now, you wouldn’t believe that Mark Cuban once worked at a computer retail store and, surprisingly, for all his charisma on screen, was canned for being late.
But that’s not the only regular and random job Cuban took on before his billions rolled in.
He sold bin bags, baseball cards, stamps, and coins as a teen, just to support his hobbies. Later, Cuban worked at a deli, hosted parties, and gave dance lessons to pay for his university fees.
Seeing his friends settling in dead-end jobs, Cuban, wanting to be “more entrepreneurial,” took the initiative and founded Microsolutions. He then sold the company for $6 million (£4.45 million).
However, it wasn’t until Cuban was 40 that he would reach billionaire status. He became a billionaire by co-founding Audionet (later Broadcast.com), a company Yahoo would acquire for $5.7 billion (£4.2 billion).
Sarah Blakely (Spanx)
American inventor and philanthropist Sarah Blakely is a household name in the clothing department as the founder of Spanx. But the billion-dollar company’s success story wasn’t as smooth as Blakeley’s silhouette-smoothing garments.
Interestingly, Blakely, who was born in Clearwater, Florida, had no experience in fashion, retail, or business when she began her journey. Her education and training were in communications.
What inspired her to invent Spanx was her frustration with tights, which were tremendously popular in the ‘80s. Recognising a critical flaw in its design and a great business potential, Blakely invested her £5,000 savings to secure a patent.
Despite the rejections she received at first, Blakely’s smart decision to protect her idea made Spanx a worldwide success, turning the Florida-born innovator into a billionaire.
She’s now one of the youngest self-made billionaire females, alongside Lucy Guo, Daniela Amodei, and Shuo Wang.
Sir Philip Green (Arcadia Group)
Sir Philip Green has recently made several headlines involving the British retailer, BHS. But despite his slip-ups, there’s no question that the man is responsible for building a retail empire from the ground up.
Green was born in Croydon, a borough in South London. At 15, he had to quit school to work for a family friend in the shoe importing industry. This experience allowed Green to travel across Europe, the US, and the Far East.
To start his business selling and importing jeans, the young Green has to borrow £20,000. He also acquired leftover stock from various label brands and sold them for profit. He set up discount shops in Mayfair to do this.
With his buying and selling idea, Green slowly established his retail empire. In 2000, Green bought the BHS department store chain for £200 million. Two years later, he purchased the Arcadia Group for £770 million. In 2025, Sir Philip Green’s net worth stands at a little over £1 billion.
James Dyson (Dyson Company)
Yes, this is the same person behind the popular bagless vacuum cleaners. Inventor and industrial designer James Dyson initially studied interior design and furniture at the Royal College of Art.
Inspired by Buckminster Fuller, Dyson later moved to engineering and invented his first successful design, an easier wheelbarrow. But while a commercial hit, he lost control of his business and was forced to sell.
His motivation to build the Dyson vacuum cleaner was rather amusing: he was frustrated with his Hoover and wished it worked better.
Around the 1980s, Dyson made a working prototype for his bagless vacuum cleaner. However, it would take another decade and over a million pounds of debt before he got to release it in 1993.
Dyson was this close to bankruptcy. But he managed to turn it around, solidifying his company’s name as one of the most recognisable home appliances brands on the planet.
Deni Darenberg (Dog Advisor)
Nothing gives a weary sail fresh wind better than a story of young entrepreneurs succeeding, and Deni Darenberg’s story is quite inspirational indeed.
While certainly young at 16, Darenberg’s passion as a young entrepreneur showcases that success in business knows no age.
He’s the founder of Dog Advisor, a website and app that provides expert canine support for dog owners. They’ve since published over a hundred well-informed blog articles addressing common fur-parent issues.
Beyond helpful doggy content, the company also launched an AI chatbot called Max, designed to support pet parents in emergencies. Darenberg’s Dog Advisor won a UK Business Awards in 2024.
Bottom Line
Many of the world’s largest businesses didn’t start big, with high-rise offices and multi-million dollar investments. Some began as a side hustle, in a garage, with a small reserve of funds, often from the founders’ own pockets.
These eight brilliant entrepreneurs started modestly and have proven it’s possible. Now it’s your turn.
