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Metro
4 days ago
- Business
- Metro
I went from homeless to entrepreneur — these are my key tips for success
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. To view this video please enable JavaScript, and consider upgrading to a web browser that supports HTML5 video 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. View More » '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? Do you have a story to share? Get in touch by emailing MetroLifestyleTeam@ MORE: 'If I didn't want to work, I wouldn't have gone to a thousand interviews' MORE: I built a fashion business from the ground up — you don't need entrepreneur family to succeed MORE: Porn sites to make major change to who can watch x-rated videos Your free newsletter guide to the best London has on offer, from drinks deals to restaurant reviews.
Metro
22-05-2025
- Business
- Metro
Ignore the CEO influencers — not everybody's cut out to run a business
Jacqueline took over her the family business aged 19 (Picture: Supplied) Listen to article Listen to article Your browser does not support the audio element. From Steven Barlett's Diary of a CEO to Simon Squibb's What's Your Dream?, the UK laps up advice on how to become a business mogul. And after years of wage stagnation and a cost of living crisis, that's no major surprise. After all, who wouldn't want to ditch the 9-to-5 and make millions doing something they love? According to Jacqueline O'Donovan OBE however, looking up to influencers can set regular people up to fail. 'There really are leaders and followers,' the 57-year-old tells Metro. 'If you're an entrepreneur, you're born an entrepreneur — there is no making you into one. So starting up a business isn't everybody's cup of tea.' Her own entry into the world of business came at 19. When her father Joe died aged 51, the family waste management company was left in the hands of Jacqueline and her three older siblings. She claims entrepreneurs are born, not trained (Picture: Supplied) A lifelong Londoner and second-generation Irish immigrant, she slept in a cot in the family's one-bedroom flat until she was five, and was picked on because of her weight throughout her childhood. 'I didn't get on very well at school,' Jacqueline recalls. 'It was the era where, if you didn't get something, you got left behind. And I basically ran out of there at 16, sticking my two fingers up and saying, 'I don't need you'.' Her plans to work in childcare came to an end when she got the call her dad had died of a heart attack. And while her eldest brother was initially expected to take on his business, Jacqueline's knack for problem-solving saw her naturally falling into the role. She says: 'There was never a conversation, sitting around the table going 'you're gonna do this, you're gonna do that'. We just went into autopilot. We need to make sure mum's okay. And we need to get on with it.' Success takes hard graft and natural talent Once she realised where her talents could be best put to use, Jacqueline worked tirelessly on gaining qualifications and certifications that would set the firm apart. She also brought about numerous changes, from upgrading the company's lorries so they were safer for cyclists to ending its use of landfills and fossil fuels. Within the three decades she was at the helm, O'Donovan Waste went from a small firm worth £175,000 to an empire boasting a £22 million annual turnover. In 2023, she was made an OBE for services to Recycling, Safety and Industry (Picture: Supplied) But despite her success, being taken seriously in such a male dominated industry wasn't always plain sailing. The mum-of-one says: 'I'd walk into rooms with 20 fellas in there, and it's like Moses parting the Red Sea… 'In the early days, they used to insist on talking to a man, so I'd put them through to my brother Brendan – but little did they know I taught him everything.' Following the birth of her son in 2005, she also dealt with postnatal depression, which took more than three years to overcome, largely due to the support of her loved ones. While in many ways, Jacqueline believes these struggles have made her a better leader and parent, there's a high level of resilience required to be the boss — and it's not a lifestyle everyone can handle. Recent data shows that as many as one in seven new businesses fail within the first three years: 20% because they were outcompeted, 14% because of not having the right team, 7% because of disharmony among team or investors and 5% because of burning out or lack of passion (5%). 'There is a massive skill set to being a business owner,' Jacqueline says. 'You've got to be a therapist, you've got to know your numbers, you've got to be able to sell, you've got to be able to buy. There are so many hats — and you can't just go to the shop and buy them, I'm afraid.' She believes women need to quit apologising and back themselves more (Picture: Supplied) The cult of personality In her view, social media stars who pivot into business – such as Mr Beast, whose chocolate brand Feastables generated $251 million in sales in 2024 alone, or KSI, whose Prime energy drink (founded alongside fellow YouTuber Logan Paul) became an instant sell-out and hit $1.2 billion revenue within two years of launching – are wrongly held up as role models for would-be owners. The latter has been the subject of numerous business profiles, with one article describing him as an 'all-round entrepreneur', while reality stars including Molly Mae Hague, Alex George and Jack Maynard have all been featured on Diary of a CEO to share their advice on making it big. However, Jacqueline says many of these people 'got lucky' due to their personalities, and that 'doesn't make someone an expert in how to run a business'. 'These influencers are telling everybody that they can be an entrepreneur, and it's ruining youngsters today, because they all want to be like KSI or go on The Apprentice,' she adds. Signs you're not ready to commit full-time to your business You're clueless about business basics From balance sheets to marketing, Serge Santos – who quit his job as a physicist to start his own business – argues 'one of the most important steps on this journey is developing core hard skills.' If you don't have a grasp of how companies operate day-to-day, you're throwing yourself in at the deep in. You don't have the funds Entrepreneur, investor and business mentor Martin Warner writes in Startups Magazine: 'Without at least six months of expenses covered, entrepreneurs in the early cash-strapped stages of their startups make poor decisions that contribute to the failure of the business.' You don't know your market Before you leave your job, you should be confident your business has legs – either through extensive research or the fact you've already made it a success on the side. Martin claims those that fail to do this 'almost always fail, because they are unable fully to define their business or answer the key questions any investors will inevitably ask.' You don't have a strong enough support system Alongside family and friends to stand by your side through the inevitable ups and downs, Amy Porterfield, author of Two Weeks Notice: Find the Courage to Quit Your Job, Make More Money, Work Where You Want, and Change the World, says 'you'll need emotional support through a therapist, business coach, co-founder, or all three.' 'The life of entrepreneurship is intertwined personally and professionally,' she explains. 'You can't blame a boss or company for failures. This time it's on you.' You're in it for the wrong reasons 'Desperation to leave a job shouldn't be your motivation for creating your own business,' Amy adds. This sentiment is echoed by Matthew Capala, founder of Alphametic, who tells Forbes: 'If you are just wanting to call the shots because you do not like the leadership style of your boss, or the corporate culture is toxic, consider another job… Being an entrepreneur is not about calling the shots. Building a culture is exhausting if you are not 100% invested. Know your 'why'.' You aren't willing to consistently put the time in Givelle Lamano, owner of Lamano Law Office, recommends asking yourself whether you 'have the time and dedication to make this work—especially if it's your first business, you have little or no experience or you have a family to support.' Consider too, whether you can keep this up on a consistent basis, as founder Richard Fong notes: 'Early sales can deliver a huge confidence boost when starting a new venture, but it's crucial to ensure that success can be reproduced month-in and month-out.' You need stability According to Skye Robertson, Head of The Escape School, successful entrepreneurs 'accept uncertainty, act on what information they have access to today and trust their ability to create whilst reacting to unfolding events.' So if you want a stable routine and a regular paycheck, the business world probably isn't for you. Your people skills aren't up to scratch 'Networking and marketing are key,' says Stephie Althouse of Top-Notch CEO. 'For example, if you are an engineer and you want to open an engineering firm, of course, you need to be great at engineering. However, you need to be or get good at marketing and client acquisition — or hire someone who is. [Otherwise] your business endeavour will not be successful.' You're afraid to make mistakes Peter Shallard, the 'Shrink for Entrepreneurs', highlights that bad decisions are a necessary part of business ownership. But if you're too scared of getting it wrong, you won't learn how to get it right. 'The wannabes become real entrepreneurs when they realise the only 'secret' they're missing is the courage to act,' he says. She recommends people do their research and seek the advice of industry professionals before giving up the day-job. For many though, it's simply a bad idea altogether. Instead, Jacqueline proposes getting 'hold of the financial reins' in traditional employment by finding what you're good at and making yourself indispensable. 'Know your worth,' she adds. 'Because bosses know their staff's worth. We've had some who just used to clock in and think that they that's why they they should get paid, and it's obvious.' When asking for a promotion or pay rise, leave what you want at the door and state your case solely on the basis of what you bring to the company. 'What really annoys me is when people say 'I want to eat fillet steak instead of burgers, or I want to eat lobster instead of cod, because that'snothing to do with me,' she adds. 'You get it because you've earned it, because you've gone above and beyond in your role.' Women in particular are already at a disadvantage here though, with the ONS Human Capital Estimates report finding women are paid an average of £260,000 less than men over the course of their careers. In Jacqueline's experience, many women 'hide behind the word sorry' and end up being overlooked — often passing up opportunities because they've not got every single skill listed on a description, while 'a man that's got only three of them will go for (and get) the job.' Don't be afraid to shout about your successes to keep up, but bear in mind that although 'there's no such thing as a quiet leader' there's also 'a fine line between being confident and arrogant.' Jacqueline says: 'Treat people well on the way up, because you'll meet them on the way back down. I'm a firm believer in that one. And remember, it's nice to be important, but it's more important to be nice.' As advice goes, it may not be as rousing as 'if you dream it, you can do it,' but it's probably a more realistic route to success for the majority of us. Do you have a story to share? Get in touch by emailing MetroLifestyleTeam@ Arrow MORE: I started my period at 11 – heavy bleeding cost me months of school Arrow MORE: Four UK companies that offer 'life leave' – a perk employees actually want Arrow MORE: 'Knee knockers' are clogging the London Tube network and commuters are furious
