04-07-2025
The Accidental Entrepreneur
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When Simon Squibb knocked on a stranger's front door at age 15 and asked if he could tidy their garden, he wasn't chasing a dream. He wasn't pitching a side hustle or escaping a corporate grind. He was homeless, grieving, and desperate. That unplanned knock would become the start of a long entrepreneurial career - not driven by strategy, but survival.
"I started a gardening company with no website, no brochure, no sales experience, having never started a business before in my life," he recalls. "And the reason that I started that business isn't because I wanted to be an entrepreneur, or I even knew what it was… I just had no choice."
Squibb, the founder and CEO of HelpBnk, a community-powered start-up support platform with over 250,000 members, is now widely recognised as an entrepreneur, investor, author, and energetic advocate for founders who don't fit the typical mould. His TikTok-style videos giving away mentorship, equipment and cash to aspiring business owners rack up millions of views monthly. But the roots of Squibb's mission lie far from the glow of internet virality. They're grounded in loss, instability, and a deep sense that the UK system isn't built to help the people who need it most.
A system not built for survival
When Squibb was a teenager, life unravelled quickly. "My father died suddenly when I was 15 years old. And not long after that, my mum and I had an argument. And my mum kicked me out of home, which meant I suddenly had to fend for myself and figure out how to make it in the world." Despite spending 12 years in school, Squibb felt wildly unprepared. "It had never been mentioned to me what an entrepreneur was, or how I could become one… I didn't know how money worked. I didn't know how anything worked. The only thing the school system had taught me was that one day I'd get a job."
But that wasn't even an option. With no national insurance number and no fixed address, job applications were impossible. "I tried. And I just couldn't get a job. So then I went to social services. And they told me just to go back home, which I couldn't do either. So I was stuck, really." That's when something shifted. "I call this moment the moment the entrepreneur muscle woke up in my brain. For the first time, I had to use it. We all have it. But I had to use it for the first time."
He spotted a large house with an unkempt garden. "Maybe the people with the nice big house will pay you to tidy up their garden," he thought. "And so I, through needing it, not just wanting it, found the courage to walk up the path." The owner said yes. And a business - albeit short-lived - was born. "It went on to fail. But I had an amazing experience the next eight months trying to make a gardening company work. And that was my first experience as an entrepreneur."
From survival to significance
That early necessity-led venture eventually evolved into a more deliberate path. Squibb would go on to launch and sell multiple companies, including Fluid, a creative agency in Hong Kong that saw significant success. But it wasn't until later that he found what he now sees as the real engine of long-term motivation: purpose.
"When I was younger, I didn't really have one belief. I just needed to survive… I think as I've gotten older, I've come to realise that the businesses that drive me the most are ones that have purpose, ones that matter more than me." It was at Fluid, a company based in Hong Kong, that this lesson crystallised. "It was going really well, but people were leaving and I wondered why. And then I realised that it was because the company was just there to make money." So he made a change. "I wanted to make it about the thinkers and the creatives and not just about making money… giving them the time to be creative and making sure they're paid well." For Squibb, the best businesses now aren't necessarily the biggest - they're the most meaningful. "I think the purpose of life is a life of purpose."
Purpose vs. cynicism
Of course, preaching purpose in a world obsessed with monetisation doesn't come easy. "Even now with what I'm doing, a lot of people judge me. It's like, 'Oh, you're just doing it for views, you're just doing it for likes.' And I'm permanently defending myself saying I'm doing it to help people enjoy their work and give people more options than just getting a job."
That's one of Squibb's loudest critiques of the UK system: it pushes everyone toward a narrow version of success. School. University. Job. Stability. But there are so many more possibilities. His book, What's Your Dream?, is a manifesto for this mindset - an invitation to dream first, strategise later. He says, "People only regret what they don't do, not what they do do… If you don't try something, you'll have a regret. And if you do try and it fails, you'll have a good story."
Advice to young founders: take risks early
Squibb's advice to UK entrepreneurs varies depending on life stage, but the message is clear: if you're young, take the leap now. "If you're single, and you've got a job, the likelihood is if you quit that job, you could get another job… you don't realise how much time you've got, how much freedom you've got. So when you're young, I think you should really just take every bit of risk you can."
Cost is the killer, so he recommends keeping living expenses low. "Live at home if you can while you get your dream off the ground. Give yourself a solid runway - six to twelve months - with low living costs and some savings to support the journey."
For those with more responsibilities? It is harder but this is no excuse. "Kids don't do what you say, they do what you do," he says. "If you want them to dream, you have to dream."
Asked what he would do if he had £500 and no contacts in the UK today, his answer is unequivocal: social media. "It's the new TV. My channel gets half a billion views a month. We haven't ever paid for a post, sponsored a post. Everything's organic." He advises putting that £500 into making one great piece of content - something that informs, entertains or sells. "I'd sell something in that video to generate the money back… with AI, it's getting cheaper."
The future start-up map: offline and online
While London remains the gravity centre of UK entrepreneurship, Squibb thinks smaller towns like Tunbridge Wells are quietly generating the next wave. "It's one of the few towns where the old high street is doing better than the new high street."
He recently helped restore a historic water fountain in the area - not just as a civic act, but as a bet on localism. "I believe we're returning to a time when we value genuine connections with people and communities. I have quite a few friends now in Tunbridge Wells who are building businesses." But the real start-up hub? "These days the best hub is online. I have a platform called with 252,000 entrepreneurs on it… you have to go where the community is."
Ask Squibb what he'd redesign in the UK's start-up ecosystem and his answer is blunt: "I'd love to make job centres into dream centres." He believes these spaces have become lifeless and bureaucratic - not built to inspire, but to contain. "I'd love to redesign them and make them places where people can go and learn how to do what they love… give them the tools, the funding and network to make that happen." This vision - of accessible, empowering spaces for anyone with an idea - sits at the heart of his platform HelpBnk. It's designed for the people the ecosystem usually ignores: the non-technical, non-venture-backed majority.
"There's 60–70% of the population that would love to start their own business but don't have any funding. They can't afford a course. And they don't have a business that necessarily people want equity in."
Whether it's a dog-walking venture, a bakery, or a flower business, he believes these "bottom of the pyramid" start-ups deserve support. "No one's really servicing that part of the ecosystem because there's no money in that ecosystem… so I'm helping that sector for free." Everyone wants to see unicorns and more successful businesses in the UK, but that means we have to encourage more people, particularly the younger generation, give them the tools, the capital and the support to start something. "This could create a huge difference in the UK long term, creating an additional sloth of businesses that are investable for the VC market. The unicorns of the future."
Winning $1m at the One Billion Summit supercharged Squibb's ambitions - especially around education. The entrepreneur challenges the idea that entrepreneurship is only for the privileged, has built multi million pound businesses and asked thousands of people to name their dream. His own? "My big dream is to fix the education system, so that schools include business education and financial literacy for students as young as 4 or 5 years old. I want to power that up, investing further in investing in education-related platforms and businesses."
If he gets his way, future generations won't need to stumble into entrepreneurship by accident - they'll be taught to dream, build, and believe from the start. And if you're young right now? You're luckier than you know. Because if Squibb realises even half of his vision, the world you'll be starting up in will be fairer, freer, and finally built with you in mind. Now that's what I call dreamy.
