I went from homeless to entrepreneur — these are my key tips for success

Metro

a day ago

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.
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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.
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.
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.
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.
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.
'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.'
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.'
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. More Trending
'Figure it out,' says Simon. 'Some doors you pull, some you push – don't make it more complicated than it needs to be.'
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.
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'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.'
The fact is, not everybody can – or even really wants to – own their own company.
But Simon believes that shouldn't stop you applying the 'entrepreneurial muscle' to your working life – and that this starts with asking your boss for equity in the business.
Pitch an idea that'll save them time or cash, show them the value you add and how having a stake in their success will motivate you to do even more. The worst they can say is no, right?
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