Working Hard with Grace Beverley
A step-by-step guide to finding your dream and actually making it happen
08 Jun 2026
Transcript generated automatically by AI and may contain errors.
Chapter 1: What is the main topic discussed in this episode?
What is up? I'm Grace Beverley and welcome back to Working Hard, the podcast-shaped guidebook on how to improve your own life and achieve what you actually dreamed of doing, because life's too short for boring podcasts and bad advice. What is up and welcome back to Working Hard. Guys, I'm so excited for you to listen to this episode.
I want to start with something that I think a lot of people will relate to. There's that feeling of knowing that there's something you want to build or create or do, but constantly finding reasons why now isn't the right time. And the person I'm speaking to today has spent his entire career trying to prove that wrong.
Simon Squibb went from sleeping rough at 15, starting a small gardening business and step by step building business by business, and eventually experiencing a life-changing business sale. Since then, he's dedicated his life to funding strangers' dreams on the street and built a global movement around the idea that everyone deserves a shot.
If you're confused about your path or you've got an idea that you just can't shake, this episode is a proper step-by-step guide to building your dream. We get into what freedom actually means, how to figure out what you actually want, how to start without quitting your whole life and what failure really teaches you.
But before we get into the episode, please make sure you're following the podcast on whatever you're listening to it on right now. It means a lot to us, but it also means that you get a new episode in your feed every single Monday completely for free with no paywall and means that we can keep it that way. Simon Squibb, are you currently more working hard or hardly working?
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Chapter 2: How did Simon Squibb's early life experiences shape his entrepreneurial journey?
I'm doing both, I think. It doesn't feel like work, so I feel like I'm hardly working, but I'm actually working hard. But I think that's why purpose helps you work without feeling it.
Yeah, and I want to dive into that because your story is incredible. Even just like going through the bullet points of where you've been and everything. I want to go right back to the beginning because I feel like that context around your relationship with work is so important.
And you've spoken about being 15 and having the harrowing experience of watching your father have a heart attack and becoming homeless and unable to find a job.
Can you tell me a little bit about how that shaped your relationship with what I guess was then you just being thrust into this idea of work as an essential way of keeping you alive rather than maybe leaving school and being able to dawdle around a bit and work out what worked for you?
When I think back to my early days, I would probably describe myself as having an unlucky start to life. But I think luck is a strange thing. Sometimes luck can be perspective. But my father died and I found myself three weeks later homeless. And I did what the system told me to do. The system tells you, go get a job. You can get a job.
Or the system tells you if you can't, and I couldn't get a job, by the way, because I don't have a national insurance number and I didn't have an address. So no one will give me a job. And so then the system tells you go to social benefit, go get social security money and they'll give you a home and it will be fine. So I went to the social benefit system and they just basically said no.
In fact, they said, I think, which is kind of worse than no. They're like, no, because... there are six other people in front of you that all have kids and they need housing first. And in my head, as a 15-year-old, I thought I was a fully grown man and I totally understood. I didn't get angry. No, you've got to give me a place to stay. I'm a kid. I didn't think that.
I was like, oh, right, absolutely. People who have kids need somewhere to stay. I will be all right.
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Chapter 3: What does freedom mean in the context of following your dreams?
I can sleep outside. So it didn't even occur to me that the fact the social system didn't and couldn't help me It didn't occur to me that that was wrong. And so then I just moved into this third area, which is like an area that I'd never really been taught, which is why I'm so angry today. I wasn't taught that I can have an idea in my head and make it real.
And the only reason I discovered this was a possible thing for humans is because I had no choice. And so I had no job. I had no social benefit underpinning me. And one day, I'm walking past a big house. And for the first time in my whole life, my entrepreneur muscle woke up in my brain. And it spoke to me for the first time. We all have it.
Everybody, every single one of your listeners has this entrepreneur muscle. If they don't know it, they have it. You just need it to be activated. And sometimes having a really difficult thing happen to you can activate it. So you don't just want it, you need it. And I needed it to wake up. And it did. And it told me the garden was messy in this big house.
Surely they've got the money to pay me to tidy up their garden. That's it. And then through sheer having no choice, I walked up to the front door of that house. I knocked on that door and I asked the person that answered it, would you let me take care of your garden and would you pay me to do it? And they said yes. And that was it.
That was the first gardening company business that I ever started. And so, yeah, I think that I look back at my childhood, that kind of stage in my life in a weird way. I spent a long time feeling really sad about it and often feeling my dad was gone. My life was awful.
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Chapter 4: How can someone identify what they truly want in life?
I had such bad luck. And now later in life, I look back at that moment and think, wow, I was kind of lucky. I was lucky to break free of the system, the treadmill system, and I was lucky to wake this part of my brain up that everybody has and realise that anyone can if they want, not they should, anyone can if they want be an entrepreneur.
Yeah, and I think that's really powerful and I think it reflects why so many entrepreneurs came from a place where actually if you ask them, you know,
what made you start it yes so many entrepreneurs have a very specific origin story and it was this idea and it led to this and they decided to quit this and whatever I think so many entrepreneurs come from a position of need where the maybe not the same kind of existential need that you were facing at that time but that need of kind of actually the risk of not doing this feels bigger
because I don't know how I'm gonna get to where I want to in my life if I don't start taking some big moves. And I think that that actually is exactly in parallel with what you've just said in that, When you create a life in which taking risks is the only option, then you start making those moves at a much higher rate and with much more enthusiasm because it is your kind of one option.
So I'd love to hear from that point, how did that turn into your entrepreneurial journey? Because I can imagine at the same time that turning into anything else would have still been a leap.
Well, I think what happened to me, you can fabricate this, by the way. You can fabricate. Most people want to be successful, all your listeners, by asking to put up their hands and say, who wants to be successful? Everyone's listening right now because they do. They want to make their lives better in all sorts of ways.
The truth is the only way you make your life better is needing it, but you can fabricate it. So what happened to me next? Okay, so I started this gardening company. I asked someone for help because I didn't know what I was doing. And they said they would only help me if I paid them. And that was my first experience with a course selling model. And they said to me something I'll never forget.
They said, if you don't pay, you don't pay attention. And I remember thinking with all my might, like, listen, I'm desperate for knowledge. I don't know what I'm doing. I will pay attention. This pay to pay attention is not true. It's pain that makes people pay attention is what I discover later. If you give people pain. then they pay attention.
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Chapter 5: What practical steps can you take to start pursuing your dreams?
Sometimes money can be a little bit of pain, but the truth is I had pain. I needed that knowledge and it wouldn't help me unless I paid them. And it just stuck with me, which is why I'll never charge anyone for help. I will not charge people to get help because you can't leave people behind. I was left behind because I didn't know what I was doing. So my first business failed.
So gardening company didn't work. In the end, it didn't go as the way I'd like it to go. So what happened next? Well, I turned 16. I had a national insurance number. I was only homeless for eight weeks because this gardening company worked at the beginning and made money. I got myself a place to stay. I had an address. Now I had a national insurance number. I could get a job.
And that's what I did. I got a job. But it was too late for me to enter the working world in that way. And the system, I'd woken up. my brain would no longer accept the way the world as it was.
So I got a job in a hotel and in the first two weeks of being at that hotel, the phone would ring and the receptionist would pick it up and be like, hello, I'm sorry, we're full in the hotel today and put the phone down. So they were so proud to tell the guest who was calling for a room, this is before the internet, your listeners might not remember this, people used to ring hotels.
So this is a long time ago. Put the phone down. And then I said, why did we just hang up on that customer? We could have got their details. Maybe next time we can tell them if we've got a promotion. And the receptionist was, well, you know, this is what we just would fill up. We haven't got time to deal with it.
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Chapter 6: How does failure contribute to personal growth and entrepreneurship?
We've got guests checking in. So I came up with an idea of something called Accommodation Express. where people could ring up the hotel that was full and we divert them to a telephone number that would find them a hotel in the nearby facility. And we get 15% commission for booking that room. So it was the inquiry wouldn't be wasted. And I started my second business, Accommodation Express.
But basically once that entrepreneur muscle had been woken up in my brain, I found it very hard to accept a salary and be told what to do. And so I started a second business called Accommodation Express and this did work. This made me, in my mind at that time, proper money. I made £80,000, which at the time was a huge, huge sum of money for me. And I managed to make a business work.
And so I actually had the early days of hotel.com. I actually sold that business too early. Another mistake. You do make so many mistakes in the process. But I went from, okay, I can get a job now to realizing that, no, why would I get a job? Why would I sell time? It doesn't make any sense. I want to build a brand, not just work for someone else's brand.
I want to build something where eventually I own my time.
And what were the main emotions that made you kind of feel that? Because I totally understand the experience of, I guess, a certain element more freedom when starting your own thing or freedom to think and solve problems the way you want to. But I also think that given how you were at the time, I can imagine that... there also would have been a huge call internally to security.
Like, I think that the way you say it, it feels very, oh, yeah, of course this is the case. Like, of course I exercised that entrepreneurial muscle once and then I thought, well, now I'm an entrepreneur, I have to do things that way. I can imagine someone in the exact same situation thinking the opposite and going, oh, well, that didn't work after, you know, that winter because...
people didn't need gardeners. So I need to find something where even if the business struggles a bit more, I'm still being paid. What do you think it was that made you think of entrepreneurship as the only solution for you, rather than one of two solutions where one actually maybe is a little bit more security for what had been quite an insecure situation for yourself?
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Chapter 7: What mindset shifts are necessary to embrace entrepreneurship?
Yeah, I'm thinking back. It's a really interesting point. I think there was lots of factors. First of all, I think once you've experienced entrepreneurship, one, you realize how hard it is. But kind of like exercise or anything, something hard makes you stronger if you complete it. So I got a bit addicted to the building concept and I enjoy it.
I enjoy taking something from nothing and making it real. And I got a bit addicted to that. So when I was in the job, what was security, I guess, which was the salary bit, wasn't enough. to take away that I would pitch an idea to my boss and they would say, no, no, Simon, that's not what we do here. We're not going to take the inquiries and turn it into a business. We're a hotel.
We just take bookings. Sell the conference room, please. That type of thing. So I'd woken up. That's the only way I can describe it. My ability to accept commands that didn't make sense or opportunities that were being missed, my brain just wouldn't accept it anymore. If I hadn't started something that failed, I wouldn't have felt that feeling I'm talking about.
It's so funny because when you say that, that really makes me think of what I felt originally when... Because I only did 13 months in corporate before I guess I became an entrepreneur. And the only reason that happened, I think I would have done well more had I started in that corporate world after university. But because I did that...
before university when I was 18 and I had the one main thing I had issues with in the corporate world I didn't mind the hours I didn't mind having a boss I didn't mind or I found it very glamorous I thought it was great I loved tottering around I thought it was you know I thought it was what I wanted to do the thing that frustrated me the most was when things were being done slowly inefficiently or in a way that didn't make sense to the business and
And there was no way to change it because it was just the way things were done. I think had I not got so frustrated with that, I would have gone to university, started the businesses as I did and still gone back into corporate because I would have thought just as I haven't tried entrepreneurship, I haven't tried my corporate dream yet.
So I need to also see that through to see if that's the right thing for me. And it's so funny. I always wonder about whether that is something that everyone has.
has or whether it's like I see it as almost a, I think it can be a negative trait in some ways, like the inability to put up with things being done badly and just want to, even if it takes double the amount of time to actually fix the process, just to not see things being done in a stupid way.
I totally agree.
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Chapter 8: How can you balance security with the desire to follow your dreams?
once you get that itch it means that like anytime I talk to a business owner now anytime I'm speaking about a specific problem even if it's not one I've got a business in that area I'm like I could probably spend an hour talking to you extremely passionately about why something doesn't make sense and that is the essence of entrepreneurship
I completely agree. I think people listening, there's something about this that's quite important, I think, to dig into. You kind of, again, I believe everyone can be an entrepreneur. Not everyone agrees with me on this. But I think the thing that we're talking about here, it's not a skill set thing. It's a realization that you are in control of things thing.
And once you have control over your life, it's very hard to give it back. So it's like, I've never been to prison, but I don't know what it's like. Imagine being released and you have to follow the rules when you're out of prison still again. But being in prison was the reason you're not going to commit a crime again. I think people don't understand that they can control their own destiny.
And that includes frustrations in your life. So for example, I only work with people I like. I don't have to work with people that I don't have fun with, right? I don't have to. Whereas in corporate, you have to do that. Why would you? There's little things, right? If there's an opportunity in the business to make your customers happier by investing a bit more, you can just do it.
Whereas a finance department would say, well, you know, cost covering, we're not sure we want to do that. It's just you can do things. And I think it's something everyone can do. And once you experience it, you won't want to go back. It's a bit like being a parent. On paper, being a parent makes no sense.
Yeah, zero sense.
So I've got an eight-year-old, right? And when you look at it, you're going to lose time. It's going to cost you money. You could argue it's stressful. That's why a lot of young people aren't having kids now. Because on paper, it doesn't make sense. But when you have a kid, you have unconditional love. You never experience it until you have a kid.
I don't have unconditional love for my parents or my family or my friends. You have conditional love. But when you have a kid of your own, it's unconditional love. And having your own business is a similar kind of thing. You just have control and you have unconditional love for it. And that can't be had via logic. Salary makes sense logically, but the upside is capped. That's obvious.
But the control is the most beautiful thing. Own your hours. You and I can stop this podcast right now and just go for lunch if we want. Right? We have that power. Why would you not want that? That's total freedom. That's totally out of the prison. Freedom, right?
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