Simon Squibb Images © BROOD Magazine Limited

If you’re an entrepreneur, or have aspirations to start your own business, and you have a TikTok or Instagram account then you are sure to have heard the words, ‘’What’s your dream?” words that have become synonyms with renowned entrepreneur, Simon Squibb.

Simon’s story is one of grit, talent and an unbelievable determination to build a life for himself that was very different from the one he had as a homeless 15 years old who started a business, in order to eat and earn enough money to get somewhere to sleep. Simon is very vocal about his passion to shake up the school system and to empower everyone to have the knowledge and confidence to start their own business. To live a life with purpose and doing something that they love. Simon wants to break down the barriers that people list as reasons not to live out their dreams. Simon’s story of going from a 15 year old boy who was homeless, to founding 19 different companies, to selling his agency Fluid to PwC for more money than he’ll ever need, has left him inspiring the masses and he wants to use his platform to help people. Simon went viral when he bought a derelict staircase in London, and put a doorbell on it where people now come from far and wide to pitch their dreams, which Simon and his team then endeavour to help make these dreams happen with the help of his company, Helpbnk. Helpbnk was created to build a community where people can #givewithouttake and help their fellow entrepreneurs to build their businesses. Simon has amassed an impressive 2.2 million followers on Instagram and over 5.3million followers on TikTok over the past couple of years, becoming a recognisable face for many dreamers throughout the UK and Internationally. In November 2024 Simon was chosen by the Great British Entrepreneur Awards to be inducted into the Hall of Fame, and in the same month, he was presented with his Gold YouTube Plaque for reaching 1,000,000 subscribers. Simon’s book – What’s Your Dream, is released on 16th January, 2025. The book has been hailed by #1 New York Times Bestseller Jay Shetty, ‘Simon loves dreams and he wants you to live yours. This book will stop you from giving up on your goals and start building the life you want’ and Dad of 5 and Chef, Jamie Oliver ‘Inspiring stuff…Simon empowers you to follow your dreams without fear’ 

We were honoured to have been invited to Simon’s family home for a couple of hours despite his busy schedule. Naturally, he streamed our photoshoot and interview on TikTok, as always sharing his life behind the scenes with his followers, as we chatted through his incredible business journey and how he wants to shake up the system to empower more and more people to live out their dreams.

What inspired you to enter the world of business? 

“Well, I had no choice but to enter the world of business. I couldn’t get a job and I had tried begging on the streets and I couldn’t make any money, so at 15 years old the only option I had was to start a business.”

When did you find that first piece of success in business, that made you stay on that path of being self-employed and believe that it was a road worth staying on? 

“Well, I had a very small measure of what success was back in those days. If I can make enough money to eat and maybe get a roof over my head and have somewhere to sleep then that was success to me. I actually think it’s a really good yardstick for making sure that you treat success with little milestones, not big ones. A lot of people say, I want a million pounds and that will mean I’m successful, when actually you might then spend a lot of your time disappointed so it’s better to give yourself small targets. That’s why I bought the staircase in Twickenham, to illustrate the little step-by-step process. Like for me back then you know the day I got 1 garden contract, one person saying I could take care of their garden, that was a success. That paid for food and accommodation for the week.”

“ I think having ownership over what you do every day is the most valuable thing you could possibly have, owning your own time.”

That’s a really important point and it’s actually something we’ve talked a lot about, as it’s so easy it is to get caught up in that end goal and miss the opportunity to celebrate all those little wins. 

Absolutely, and especially when you’re comparing yourself to other people and their businesses and it deflates your enthusiasm for what you’re working on if you don’t measure it by those little steps instead of these big massive ones. 

Do you think your journey to success is what led you to start the purposeful project which is now HelpBnk? Tell us a bit more about your journey to get there. 

Yeah, I actually changed the name from Purposeful Project to Help Bank. So my focus now is on the Help Bank brand, but originally it was a purposeful project for me and it was really helping the 15 year old boy who struggled. I didn’t know anything about business. I’d been in school for 12 years at this point as well and I knew nothing about how money works. I knew nothing about the world of business. I knew nothing about how to sell myself or the services I would eventually sell, so I think that’s where that passion came from, I just wanted to help the 15 year old me. As soon as I got to a point where I was no longer worrying about money, when I had filled my own bucket, then I thought right, how can I help other people climb up the ladder? It’s that whole analogy of don’t pull the ladder up behind you. Put the ladder down and help people up. I want everyone to know how to make money. I want everyone to know how to start a business, I call it informed consent, to start a business if they want, they don’t have to, but at least let them have the option. And so my mission is to help that 15 year old who didn’t know how to do it and didn’t have any help at the beginning. When I asked for help, from people that would have been able to help me, they would only help me if I had money, but of course I had no money to pay them. They used to say something that I never forgot, which is – if you don’t pay, you don’t pay attention. And I thought that was not true. I know that is not true because I’m so desperate for knowledge. Of course, I’m going to pay attention. The problem was that I couldn’t afford to pay them for that knowledge. So from that moment onwards I logged that and I thought one day I am going to give the knowledge to people for free and I’m never going to use that bull**** line – if you don’t pay, you don’t pay attention, because that’s just used so that people can justify charging people for help.”

“when you’re comparing yourself to other people and their businesses, it deflates your enthusiasm for what you’re working on.”

Between schools not teaching us the skills to start our own businesses and it being so hard to get grants, loans etc to start a business, making it seem something that’s so out of reach for so many people, how important is it to you to break down those barriers and help people to see that it is something that is possible for them? And what changes do you think need to be made to show people that. 

There’s a lot we need to change, but I think on a basic level, a simple example is when I first went to school, I remember at only five years old being asked by my teacher on the first day of school, what will you be when you grow up? What that does is instantly trap your mind into thinking about one particular thing, Doctor, Lawyer, Teacher, whatever it is you can think of at that age and with that literally from a young age you’re on a path to university out and the other end to work for someone else. I think we should open up the question people when they arrive at school and it should be ‘what problems do you want to solve’. Because now if we’re going to live to 100 which is predicted for our young people, they could live until your 100. You can do 5, or 6, or 7 different things in your lifetime. You do all of these different things at some point in your life and so you shouldn’t be pigeonholed into one particular thing. Of course, if you want to be a Lawyer or a Doctor that’s fine, but I also think we need to start being honest and saying if you want to be a doctor, it’s probably gonna get done by AI in the future. So if you want to be a doctor, just bear that in mind. So, I think we need to be honest and say this is the future as well. I think we should be taught financial literacy and how the world works and give people the ability to educate themselves so that in the future they feel like they’ve got a purpose in this world. It is that simple on a basic level? The whole long list of how it could be done would take up hours of our day, but you only need to look at the stats that 80% of A Graded students work for D Graded students. Why is that? Because the school system is actually training people to work for someone else – Sit down, do an exam. Don’t stand out. Don’t say what you think. Shut up, and do what you’re told. If you conform in the school system to do that then you’re much easier to control when you go into the workforce. It’s like if people turn up to work five minutes late, does it really matter? But, people love that control and the school system makes the A students controllable and those students are smart people. That needs to change. And this isn’t just me saying this, Carnegie and Henry Ford admitted that they invested in the education system to do just that – they said it out loud. But we’ve decided not to recognise it and do nothing about it, even though it’s now a 100 year experiment. If you look at 5 year olds, 95% of them if you test them are considered geniuses but then they hit 12 or 13, it drops down to less than 2%. From this magical education system – it actually dumbs people down. It makes people fearful. It doesn’t allow people to use their IQ. It only focuses on a weird grade system that is mass produced and not tailored to individual needs. I was told I was stupid at school. I’m not stupid, but if you’d have asked a nine year old me I would say I’m a little bit stupid ’cause I was dyslexic as well and that was drummed into me at school.”

You now have a son, how do you approach learning with him? 

“I homeschool my son. He’s not in public education, and I ask him what he wants to do today. So it’s child-led learning. It’s fascinating running my own theory with my own son. I ask him what he’s interested in, for example, you just mentioned your daughter’s interest in makeup so if she’s interested in makeup, she would probably learn about the things she maybe doesn’t even really, like accounts, and stuff like that, because she’s gotten an interest in the subject. My son was obsessed with road maps for a while. Anything to do with the road system – A1, the M25 motorway. He wanted to know where they led, how they’re connected, where they’re connected, what they were called and how they got built. And so we go into the details of how the M25 got built. And it’s a political story, how the political system didn’t want it to happen, what happened and didn’t happen. How much it costs, where the money came from, the economics, politics, he learnt it all through his interest of roads. So letting people follow their passions, follow their dreams, letting people do what is natural to them, then all the things they need to learn to do it, they will learn naturally and enjoy learning. As opposed to sitting down to learn biology or something you’re not very good at, it puts people off. It’s just a joke that subjects like Art for example are still seen as being a bit whimsical. I think as parents you are almost trained to think that you should encourage your child to go to university. But in England, you end up in debt by going to university and an education that stops you taking risks, because you feel like you have to get a job as soon as you leave.” 

As running a business can be hard at times, how important do you think it is that you build a business centred around something that you’re passionate about?

“I don’t think business is so hard. I mean of course, it is at times, but so is the other option of working for someone else. There’s still a lot of ups and downs when you work for someone else. For instance, two people have reached out in my DM’s this morning as they had been made redundant – that’s a down. I think as entrepreneurs we’ve gotta be careful how we talk. because we’re setting a narrative that isn’t entirely true. Of course, every journey is hard, but would you want to go and work for someone else now? [We agree, that we wouldn’t want to] You see what I mean? If you talk to someone who’s run their own business for more than a year and who has had some model of success, they will generally always say that they wouldn’t go back to working for someone else. And I think if we went into the town now, I think that nearly everybody who’s got a job would say they don’t really like it. In fact I haven’t met many people that like their job. I think having ownership over what you do every day is the most valuable thing you could possibly have, owning your own time. I think that people forget that running your own business although like everything else it may have its challenges, it gives you choices each day that a lot of people who work for someone else don’t have. 

But again, we have this narrative that being an entrepreneur is so hard, and of course when you’re trying to achieve anything it’s hard… climbing up a mountain is hard, but you don’t expect to achieve climbing Mount Everest and it not be hard. That is the point, that you learn, you grow, you push yourself, and you can achieve more than you thought possible. That’s the whole point of life.”

I think it can be hard for people to leave behind the structure of knowing when you will get your wages and exactly how much that you will get, as opposed to waiting on invoices for example… 

“Yes, it’s like a salary drug and the system is designed to keep people addicted to that. 

It wants you to get used to that predictability, but life just isn’t meant to be like that, it’s much more enjoyable when there are highs and lows, and you’re in charge of the hunt.”

Do you think it’s harder to make that change from having a job into starting a business once you become a parent and the responsibilities that come with that? And what advice would you give to them? 

“I think kids don’t do what you say, they do what you do. So, if you are not enjoying your work and you’re sacrificing for the kids, then they will end up doing the same and they’re not gonna be inspired. Kids don’t care how big your house is, they don’t care how many toys you get them, they just want your time and they want to learn from you. So if you want to inspire them, let them watch you follow your dreams. I’ve got a 7 year old, I totally understand the difference between when I wasn’t a parent, to now when I am a parent. There is definitely an argument to take more risk when you’re younger for sure, but there is also the argument for owning your own time once you become a parent because the most important thing you can give your kids time. I think time is the problem, not money. I do understand that everybody reading this might be like, well, you don’t know what it’s like, Simon, I’m struggling to make ends meet. But, I do understand, I’ve been there myself. I do know what it’s like. I would argue though, that if you enjoy what you do, you do make more money in the long run and you can sustain it, and you’ll stay healthier because you’re enjoying your work. If you’re not enjoying it, if you don’t have any equity where you work, it’s not scalable – you’re selling time. Most people, most parents, are selling 40 hours a week. You are selling the only thing your kids actually want, so why not build something up which means you’re no longer selling your time and eventually, if you do it right, you give yourself more time and freedom. It is harder running a business in the beginning, but only because of the learning curve. It’s because there’s so much to learn, it’s exciting and you need to be really focused, but it gets easier over time. I built 19 companies up and then brought someone else in to run them. I give them equity and someone else runs it. Now I’ve got businesses generating income and I’m putting no time into it. I think it’s easier to work for someone in the beginning, but it’s harder over time. I think if you think working for someone else is easier than working for yourself, you have been brainwashed. You’ve been brainwashed by your employer and you’ve been brainwashed by the system, it’s not true. If you work for yourself you’re in control of your destiny.” 

Obviously, when you are juggling being a parent and running a business, inevitably there will be occasions where you can’t be in two places at once. How do you navigate those times? 

“There’s always going to be times like that, that’s the struggle of life. There are three pillars to what we need as humans; attention for ourselves, looking after ourselves and our relationships we need to give attention to. It is actually very hard to do all three at once. So people talk about work life balance all the time and I’d say the answer is to combine the three wherever possible. So I go on long walks with my colleagues, or I’m running at the moment with my colleagues, so I do work and exercise at the same time. That way I’m looking after myself and I’m working well. I’m bringing my wife and my son on business trips with me, so I get to be with my family whilst I’m working. But you can’t do all three in separation. Something will suffer. Yesterday, my son asked me not to go out, he asked me to stay with him and I explained that I’m helping three people, that I promised to help, so as much as I want to be with him, and I would actually rather be with him I had committed to something. I had promised to do something, I’ve got to do it and that’s important for him to know. I’m showing him that helping people requires sacrifice sometimes for our own joy, but if it has a purpose it’s worth it. So I’m educating him even just by not being with him. I think a life with purpose is a purposeful life, so at least when I tell my son I’m leaving him to do something purposeful, it’s not just about making money.

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