Metro and the BBI are teaming up to highlight the UK’s most talented Black businesspeople.

At 15, Simon Squibb’s dad died suddenly, leaving him homeless, out of school and unable to find work. Then, he had a brainwave that turned his life around.

‘I was so desperate to get out of this situation I was in,’ he tells Metro.

‘I walked past a big house that had a really messy garden, and thought maybe they’d pay me to tidy it a bit. So I knocked on the door saying I had a gardening company (which I didn’t) and amazingly, the guy who answered was like “alright, how much?”.

‘I just picked a number out of thin air – £200 pounds a month. Then he shook my hand and that was my first ever deal. Suddenly I was a gardener with a gardening contract.’

Fast forward three decades and that same entrepreneurial mindset has made him a millionaire, with 19 companies under his belt alongside a bestselling book, What’s Your Dream?

You may know Simon from social media, where his brand of gonzo-style angel investing has earned him an army of loyal fans (who he calls dreamers).

After selling his businesses and retiring at 40 in the midst of Covid, Simon noticed a growing desire for people to become their own bosses, and embarked on a mission to help wannabe entrepreneurs do exactly that.

He now spends his days asking strangers what they’d do if there was nothing standing in their way, and has invested in over 60 firms as a result of their answers, from fintech to food delivery.

But it’s not as simplistic as ‘if you can dream it, you can do it’. And while the 51-year-old argues that everyone – regardless of background or qualifications – has it in them to be successful, they need the right outlook and support to get there.

He explains: ‘I want people to know that it’s possible, if they have a purpose or a mission or a hobby, there is a way to put it into a business context and make money by doing what you love. I want education around that.

‘If I had my way. I’d change all the Job Centres to Dream Centres, and give people the entrepreneurial skills I’m talking about. Then you could get a job, but on top of that, start a company and be your own boss. And why shouldn’t we give people that power?’

In his view, one of the biggest obstacles is the idea that the business world is only for a select few. In a recent study, Shopify found that 61% of Brits want to start their own company, yet the majority are held back by a lack of confidence in their abilities.

However, Simon’s own experiences have led him to believe the opposite; that adversity actually helps people thrive.

‘The people that succeed don’t just want it, they need it,’ he says. ‘Personally, I’ve been most excited when I had no money; I was broke, I was homeless, I had nowhere stable to sleep, so if I knocked on a door and got told to f*** off, I had nothing to lose.’

You may be reading this thinking ‘my plate’s too full already’, either with family responsibilities, a job you can’t afford to leave, or a lack of connections. According to Simon though, you can still build a flourishing side hustle – one that may even become your main gig. You just need to keep these eight things in mind.

Follow your skillset

In terms of the idea itself, forget what’s lucrative or will make the most money. Instead, Simon recommends building on your own strengths

‘Whatever you’re really good at, get great at it.’ he says. ‘In school, they’ll tell you that if you get a D in biology, you need to do more biology. But I’m saying don’t do more biology if you’re brilliant at public speaking or sports.’

It has to be about passion too, with Simon advising ‘dreamers’ to ‘match [their] hobby to their income’ – like the one he helped who turned his love of supercars into a popular (and profitable) social media brand.

Solve a problem

Your route to the C-suite may also be through spotting a problem and solving it.

Aged 19 and working at a hotel after his landscaping venture shut up shop, Simon realised they were missing a trick by turning people away if they were full. Instead of hanging up when there was no room at the inn, he got nearby hotels to give them a commission for each customer they passed along – and from that germ of an idea came his second company, Accommodation Express.

If you aren’t sure what to do, think of the little issues you or your loved ones face day-to-day, and start from there.

Be patient

For those of us used to a standard 9-to-5, it can be difficult to self-motivate or be the sole decision maker – vital skills if you’re running a business.

‘Frankly, working for yourself is hard,’ says Simon. ‘And being an entrepreneur is especially hard at the beginning because it’s a huge learning curve.’

Over time, this new role will become natural to you. You just need to stay the course and keep your eyes on the prize.

Fake it ’til you make it

When Simon walked up to that door as a down on his luck teenager, he was fuelled by that aforementioned survival instinct. The fact he didn’t know anything about landscaping was an afterthought – something to be dealt with once he’d landed the client.

In that moment, he was terrified, but he sees fear as an ‘asset, not a liability’, explaining: ‘Fear was designed to help us: you prep more, you push more, you fight, and it’s actually a superpower.’

It may be easier said than done, but once you grip the nettle and step out of your comfort zone, you’ll start to enjoy the adrenaline rush. Just ensure you actually make good on your promises.

Embrace failure

‘The school system tells you if you get an answer wrong you’re a failure,’ says Simon. ‘But look at Edison’s lightbulb, it failed 99 times before it worked. So you need those 99 times.’

The entrepreneur recommends looking at failure as a chance to grow, while using your wins to galvanise you when times get hard.

He recalls: ‘The first person that opened the door that time I started the gardening firm said yes, then the second, third, fourth and fifth person all said no to me. But because I had one, I knew it could work – and sometimes we need to remember that.

‘Then that business failed. But here’s the thing: before it failed, I made loads of money, I learned how to sell, to do contract structures, to rent equipment and do lease agreements. That’s learning you couldn’t take away from me.’

Build it into your life

Even if you’ve got past these mental blocks, life can still get in the way of being an entrepreneur. So when time is your main constraint, Simon has one main piece of advice: prioritise work/life integration over work/life balance.

In his case, that means bringing his seven-year-old son along to help him shoot and edit content, but it could translate to a variety of other businesses.

‘If you’re making candles or whatever, get your kids involved in the business,’ continues Simon. ‘When you’re doing something that’s important to you, you find the time.’

Keep it simple

While many of the people Simon chats to worry about the logistical side of business ownership, he subscribes to the ‘keep it simple’ way of thinking.

In one example of a mum whose journalling company he invested in: she had a great idea but logistical knowledge around manufacturing, so she checked major retailers’ websites to find out their suppliers, then called them and went from there.

‘Figure it out,’ says Simon. ‘Some doors you pull, some you push – don’t make it more complicated than it needs to be.’

Make yourself futureproof

Sustainability should be the goal of any business owner, so you need to plan ahead. If you don’t, you may find it’s still a slog even years down the line.

Simon explains: ‘It could be that you’re doing it all yourself and you should have brought someone in to help, like a good partner. I see people make that mistake all the time.

‘Others get too greedy, and when they make money they put it straight in their pocket. It’s vital to invest in a good team.’

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Get in touch by emailing MetroLifestyleTeam@Metro.co.uk.

Isabelle Pennington-Edmead, 28, runs her own ethical slow-fashion business with
a collection also stocked online at ASOS.

Orders from her website are made on demand to prevent wastage and aim to reflect childhood memories and femininity as well as inspiration drawn from her mixed Caribbean and British heritage.

Here, she explains how she’s made her journey from textiles-obsessed teen to successful entrepreneur, with the help of mentors and a lot of learning along the way.

What got you into the clothes design business?

It is quite a cliché, but clothes design and running my own business has always been something I wanted to do.

I’ve got sketchbooks from when I was younger where I designed what I wanted my brand to be, with logo designs and stuff. But I don’t come from a family of entrepreneurs. Everyone in my family works in the public sector, like teachers, doctors or the NHS.

That makes it hard. When you go to state school, you don’t have the connections you might at other places, or the advice. So when I’m struggling with something, I might go to a family member and say, ‘I don’t know what to do about this’, but they don’t understand.

How did you get started?

I did textiles at school and then studied fashion design at university, and then did a master’s in textiles for fashion.

After my master’s, I applied for a grad scheme with Yoox Net-A-Porter – a cooperation with the King’s Foundation educational charity. I was working on creating a sustainable collection for their private label.

I’m from Manchester, and when I finished at Yoox, I decided I wanted to move back to the north-west, but a lot of the clothes industry there was fast fashion.

So I decided to just start my own brand, because I’d learned quite a lot about small-batch production. That’s when I thought I could give it a go, starting my own slow-fashion label that reflects my mixed Caribbean, Kittitian, and British heritage.

How’s the journey going?

I’d say the challenge has been scaling. I’ve had to deal with things like Brexit. I didn’t know about importing and exporting. That was a big hurdle – navigating the production and pricing and logistics, and having to negotiate with factories.

I think it can be quite difficult, especially as a young woman, to make sure that you’re getting the right prices and being taken seriously.

You now have a collection for sale at ASOS. Did that feel like a milestone?

ASOS was a big, brilliant experience. It started in March 24 and there was a lot to learn with scaling up to that size. Everything that’s available 
to buy on ASOS from my brand is made in factories in the UK. I’m using a factory in London that’s Drapers Award-winning, so I know it’s a sustainable factory.

I’ve also got orders being stocked in small boutiques, I’ve got an order going to Bermuda at the moment, and I’ve got other collections to pitch to other sources, hopefully.

My next goal is to make the
business even more sustainable. I don’t think any fashion business can be 100 per cent sustainable, so it’s just about trying your best and putting the effort in.

A big goal for me would be to become a B Corp, which shows my business is meeting high standards.

How did you get involved with the Black British Initiative (BBI) and how has it helped you?

I met BBI CEO Darren Miller at a Windrush anniversary event. I got chatting to him and told him about my business, and he told me about the initiative.

I really liked the look of what they were doing, because coming from a creative background I don’t have any formal education in business. So even though I wanted to have a business, sometimes I felt an imposter syndrome around it, with not actually having formal education in it.

Darren has put me in touch with some great people, such as Andrew Xeni from resposible fashion brand Nobody’s Child. Having mentors has been a game-changer for me, so these connections have been so important.

What have you learned that you’d like to pass on to others if they’d also like to make a business a success?

I’d say, define your brand and do the market research. That’s very important – writing out a business plan and covering every aspect. Customers like it when there’s a story behind the product, and they can really be involved in that.

Also, try to stand your ground when you are negotiating. I sometimes deal with people on email a bit before first, just so they don’t make assumptions when speaking on the phone – if they hear my age or that I’m a young woman.

Just don’t take the first answer. I think it’s a given that they’re going to expect you to go back with different prices or suggestions. So, if you just take the first offer, obviously
they’ll go with it, but I don’t think they mind you suggesting cheaper pricing or negotiating.

And when you have bad days, you just have to ride it. You’re going to have them. And even though you can see on LinkedIn people’s highlight reels, it’s not like that every day for them either.

When things are going well, make the most of it. I try and post a lot on social media. I try and hype up
the brand.

I don’t have a massive marketing budget, so a lot of it is done myself. I try not to get complacent and take my foot off the accelerator.

Business breakfast or business lunch – which appeals?

Lunch. I’m not mad on buying breakfast out – I just think I could have made this myself, and now it’s cost me £12 or something.

Do you have a story to share?

Get in touch by emailing MetroLifestyleTeam@Metro.co.uk.

‘There are systemic structural and institutional barriers.’

‘There are systemic structural and institutional barriers.’

‘If you’re an entrepreneur, you’re born an entrepreneur.’