Simon Squibb | He Was Homeless at 15… Now He’s Worth Hundreds of Millions

Summary

School of Hard Knocks Podcast

Episode: Simon Squibb | He Was Homeless at 15… Now He’s Worth Hundreds of Millions

Date: April 8, 2026
Host(s): James, Jack, Josh
Guest: Simon Squibb

Episode Overview

This episode of the School of Hard Knocks Podcast features Simon Squibb—serial entrepreneur, investor in over 80 companies, and philanthropist—who went from being homeless at 15 to achieving massive financial and personal success. Simon discusses his journey, the flaws in traditional education, entrepreneurial mindsets, team building, the importance of purpose, and giving back. The conversation explores Simon’s failures, success habits, business philosophy, education reform, and advice for the next generation.

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Key Discussion Points & Insights

1. Simon’s Early Life and Wake-Up Call

• Tragedy & Homelessness: Simon’s father died suddenly when Simon was 15, leaving him homeless and totally unprepared by the education system for real life.
  • “I realized as soon as I hit the street that 13 years in school was a complete waste of time.” (01:30)
• No Safety Net: Social services failed to help; he learned quickly that “no one's coming to save you.” (01:30–02:35)
• First Business Out of Necessity: Knocked on doors offering to fix gardens; his first client paid £200.
  • “That’s how I started my first company, because I had no fucking choice. I didn’t want to be an entrepreneur. I needed to be an entrepreneur.” (02:45)

2. Lessons From Failure and Persistence

• Gardening Business Collapse: Built up 126 recurring customers, hired other homeless people, but failed to anticipate winter seasonality, leading to collapse.
  • “My first big lesson: I didn’t realize that when winter came, everyone stopped asking for their gardens to be taken care of.” (05:35)
• Financial Takeaway: Still managed to save from the initial success—“I had compound learning.” (06:00)
• Resilience & Learning: Every failure provided skills—client service, sales, hiring—that fueled his next ventures.

3. Critique of Traditional Education System

• Fundamental Problem: School teaches people to get a job, not to start a business or build wealth.
  • “Nothing you actually need in the real world had ever been taught to me.” (02:05)
• Systemic Issue: Schools condition people into following paths they may not want, creating a cycle of debt and disempowerment.
  • “The school system does it on purpose. It’s trapping young minds to work for someone else.” (30:53)

4. The Entrepreneurial Mindset & Action

• Action Over Excuses:
  • “Most people are telling me they need 50 grand, 100 grand to start a business. Bullshit... Go wash cars this weekend.” (03:59)
• Hard Work Never Stops:
  • “I’m worth hundreds of millions today, but I still have to do the work... There’s no such thing as passive income. That is one of the biggest lies I’ve seen.” (04:51)
• Failure as Growth:
  • “People just don’t want to follow through... You just gotta keep pushing, not give up.” (07:42)
• Teams Win:
  • “No one can do it on their own... everyone I know that’s successful has done it in teams.” (07:57)

5. Transitioning and Scaling Up

• First Jobs and New Ventures: After turning 16, got a job in hotel, but soon launched Accommodation Express—a pre-internet hotel booking business that capitalized on unsatisfied customer demand. (09:15–11:11)
• Big Break in Hong Kong: Moved to Hong Kong following a tip from a friend, which opened his mind to global opportunity.
  • “My brain just expanded sitting there in Hong Kong.” (12:07)
• Exposure Drives Growth:
  • “You can only grow to what you’re exposed to.” (12:30)

6. Insights from the Ultra-Wealthy & Cultural Differences

• Learning From Billionaires:
  • “They’re not separating work and life. There’s no work-life balance, there’s just life.” (14:14)
• Opportunity Mindset: Hong Kong billionaires imagine and create value, rather than being constrained by existing resources. (15:55)
• On Fear & Restlessness: Successful people always keep going; it’s about identity, not just money. (16:33)
• Cultural Approach to Business:
  • In Asia, deals follow years of relationship building; in the West, deals can be more transactional and fleeting. (23:37)

7. Selling, Retirement & Losing Identity

• Retirement is a Lie:
  • “Worst two years of my life from an emotional point of view.” (18:20)
  • “Retirement is bullshit. And I did retire.” (18:20)
• Need for Purpose:
  • “People need purpose. We need a reason to get up in the morning and do something.” (20:06)
• Emotional Toll:
  • “I had a mental health crisis during those two years.” (20:40)

8. Content Creation & Giving Back

• Started Creating Content to Solve a Painful Problem:
  • “All I wanted to do was provide knowledge to people for free that I didn’t have when I was 15 years old.” (26:08)
  • “If I got this knowledge to one person this week, I could change their life.” (27:30)
• The ‘What’s Your Dream?’ Project: Originated from a TikTok live where he gave away his accumulated tips to strangers by asking about their dreams—realizing showing action is more motivating than just telling people. (45:37)

9. Fixing the Education System

• Change the Question:
  • “We fix the traditional education system by changing the question we ask kids... Instead of ‘What do you want to do when you grow up?’ ask ‘What problem will you solve?’” (29:11)
• Education Traps:
  • “People are going to these four year degrees because they don’t know what else to do...you come out the other end, you’ll have a job. Not true.” (32:18)

10. On Courses and the “Wisdom Economy”

• Knowledge Should Be Accessible: Personal commitment to offering knowledge for free because not everyone can pay.
  • “Free can have value if you put value in free.” (33:51)
• Critique of Info-Scams:
  • “People that sell a course about selling a course. That pissed me off.” (36:00)

11. Investing and Startup Advice

• Solving a Painful Problem: Best founders build companies to solve their own problems, not just to sell. (38:20)
• Best Time to Sell: “The best time to sell your business is when you don’t need to sell it.” (41:21)
• Value-Add Investors: Only take money from people who can 10x your business. Otherwise, “you just got yourself a new boss.” (42:56)

12. Building Relationships, Collaboration & Gatekeepers

• Collaborate Relentlessly:
  • “Half the reason I’m successful today is I’ve collabed with people and cross connected.” (51:04)
• Persistence and Value: To work with ‘big names,’ keep pushing and come with value, not just requests. (50:52–52:06)
• Credibility Opens Doors: Leaning on recognizable credibility makes cold outreach more effective. (53:17)

13. Wealth, Giving Back, and True Happiness

• Giving Without Expectation:
  • “Give without take. I help you because I can.” (60:10)
• Purpose Over Happiness:
  • “Best thing you could chase is purpose.” (63:25)
• Freedom as Ultimate Wealth:
  • “The ultimate goal of money is not to just have a lot of money, but to actually have freedom to do what I want.” (66:53)
• Learning for Kids: Home education, nurturing curiosity and personalization over forcing standard curricula. (56:52)
  • “All I do is feed his interest. That leads to a whole slew of education.” (58:56)

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Notable Quotes & Memorable Moments

• On Schooling & Real Life:

  • “That 13 years in school was a complete waste of time. Nothing you actually need in the real world had ever been taught to me.” —Simon (01:30)

• On Action Over Excuses:

  • “Stop making excuses. And that’s what people are making all the time.” —Simon (03:59)

• On Teamwork:

  • “One plus one equals eleven is how I describe it. Nobody has done it on their own.” —Simon (07:42)

• On Retirement:

  • “Retirement is bullshit. And I did retire. Worst two years of my life… I had no reason to go up and hunt every day.” —Simon (18:20)

• On Purpose:

  • “The purpose of life is a life of purpose.” —Simon (69:14)

• On Free Knowledge:

  • “Free can have value if you put value in free.” —Simon (33:51)

• On Raising Kids:

  • “Kids don’t do what you say. They do what you do.” —Simon (69:30)

• On Wealth and Time:

  • “What they never own is their time. I remember thinking, thank fuck I started a business at 15 years old.” —Simon (66:53)

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Important Timestamps

• 00:12 – Simon’s story begins: father’s death and homelessness
• 02:45 – First business: cold-pitching gardening services for £200
• 04:51 – “I’m worth hundreds of millions, but I still have to do the work.”
• 05:35 – Gardening business failure: learning from seasonality and hiring other homeless youth
• 07:42 – Teamwork, learning to rely on others
• 09:15 – Starting Accommodation Express; innovation in the hotel industry
• 12:07 – Mind expansion in Hong Kong; exposure to global opportunity
• 14:14 – Lessons from billionaires; how the ultra-wealthy think about time and work
• 18:20 – Exit, retirement, and the emotional cost of losing purpose
• 26:08 – Starting content creation: mission to share what he wished he knew at 15
• 29:11 – Fixing education: changing the question for children
• 33:51 – Wisdom economy: making knowledge accessible for free
• 38:20 – Startup advice: solving your own problem, not building to sell, impact investing
• 41:21 – Best time to sell a business: when you don't need to
• 45:37 – ‘What’s your dream?’: using social to inspire action
• 51:04 – Collaborations; pushing past gatekeepers
• 56:52 – Home-educating his son: real-world, personalized learning
• 60:10 – “Give without take”—the real path to joy and fulfillment
• 69:14 – “The purpose of life is a life of purpose.”
• 69:30 – How Simon wants to be remembered: modeling true giving for his son

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Takeaways for Listeners

• Entrepreneurship is about necessity, resilience, and persistent action—even (especially) when no one comes to rescue you.
• Failures carry invaluable compound lessons; every failed venture builds your skillset for the next.
• Traditional education does not equip you for real-world success; real learning starts when you follow your curiosity and solve real problems.
• Wealth does not make you immune from struggle—purpose, not just money, is the crucial key to a fulfilled life.
• Collaborative mindsets, relentless value creation, and ‘give without take’ distinguish successful and truly impactful people.
• Owning your time and living intentionally with purpose is the ultimate measure of wealth and happiness.
• Changing the questions we ask young people—from “what will you do?” to “what problem will you solve?”—can transform lives.

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Transcript

[James]

A legend in the UK. Mr. Simon Squid, you have built multimillion dollar businesses. You've invested in how many companies?

[Simon Squid]

81 companies now.

[James]

Before investing in millions of people's dreams. Take us back to when you had nothing.

[Simon Squid]

My father died suddenly of a heart attack. Not long after I found myself homeless.

[Jack]

You were at a position in your life where you realized no one's coming to save you.

[Simon Squid]

I realized as soon as I hit the street that. That 13 years in school was a complete waste of time. In England today, right now, There are over 700,000 kids just in England, come out of university, cannot find a job.

[Jack]

It's really on you to, like, go out and make it happen.

[Simon Squid]

£200. That's how I started my first company, because I had no choice.

[Josh]

We've built Hard Knocks now to over 21 million followers. But it didn't start off with this nice camera, all the mics, all the equipment. It started off with an iPhone.

[Simon Squid]

I'm worth hundreds of millions today, but I still have to do the work.

[James]

Simon, if me and you died tomorrow and you had one last message that you could leave with the younger generation, what would that mean? What's going on, everyone? Welcome back to the School of Hard Knocks podcast. I'm James, I'm here with Jack and Josh, and we are sitting down with a legend in the UK, Mr. Simon Squid. Simon, you have built multi million dollar businesses. You've invested in how many companies?

[Simon Squid]

81 companies now.

[James]

81 companies. And you're doing something that's fascinating, but where I want to get things started off today is take us back before the businesses, you know, before investing in millions of people's dreams. Take us back to when you had nothing, you know, what was starting a business actually like, before the money, before the connections and before the certainty.

[Simon Squid]

Well, I started off as a pissed off 15 year old, to be honest. My father died suddenly of a heart attack. And not long after, I found myself homeless. And I went from having a safe home, a safe life. I thought I was going to be a lawyer. That's what. If you asked me, what am I going to do when I was 15 years old, I would have said a lawyer. And so my life was kind of mapped out for me by my family. And then suddenly I'm in the street. And the crazy thing is I realized as soon as I hit the street that that 13 years in school was a complete waste of time.

[James]

How old were you?

[Simon Squid]

I was 15. So I'd been in school 13 years. I didn't know how money worked I didn't know how to communicate properly, I didn't know how to pitch, how to sell, how to hire people. Nothing, nothing you actually need in the real world had ever been taught to me. The only thing I knew was how to get a job. That was the only thing school taught me. You one day gonna want to get a job. You fill in the application, you tell them your qualifications and you'll get a job. But here's the thing, I didn't have any qualifications. So I tried to get a job, the only thing school taught me to do, and I couldn't get a job. So what then? If you can't get a job and that's the only thing you've been taught to do, what do you do? Well, I went to social services. They're supposed to help you, right? That's the other thing you're taught. We have a social benefit system. They'll look after you. They told me to fuck off. Literally told me to fuck off. And that I just have to figure it out myself. And so I had no choice, frankly, in this moment. I wallowed in it for about a week, sleeping rough. And then I thought, I can't live this way. I've got to find a way out. And I described the moment that everything changed when the entrepreneur muscle woke up in my brain. School had never activated it, I think on purpose. And suddenly I realized you can take an idea in your head and you can make it real. I walked past this massive house in Cambridge, here in England, and I saw this really messy garden. And my brain spoke to me for the first time and it said, they've got a nice big house, they'll probably pay you to clean up that garden because if it's messy, that means they haven't got time. So that's what I did. I knocked on the door of that house and I said, hey, excuse me, I wonder if you'd let me be your gardener and sort out your garden. And to my shock, the guy who answered the door said, sure. Alright, give it a go. How much you gonna charge me? And I made a number up at the time, £200. I said, sure, let's try. That's how I started my first company, because I had no fucking choice. I didn't want to be an entrepreneur. I needed to be an entrepreneur. And that's what changed everything for me. Needing it, not just wanting it.

[James]

Hey, his first business down there was what?

[Josh]

Josh Landscaping.

[Simon Squid]

It's good, good place to start. I just did a five hour livestream before coming here and Honestly, most people are telling me they need 50 grand, 100 grand to start a business. Bullshit. I tell them one person needed money to buy a camera. I'm like, go wash cars this weekend. Go wash cars in the expensive part of London. They've got big houses and no garages. Go wash cars for 35 quid a car. Wash 10 cars, you got the 350 quid you need for a camera. Stop making excuses. And that's what people are making all the time.

[Josh]

One of the things I love about that too, is people look at where we are today and especially where, you know, we've built Hard Knocks now to over 21 million followers. But it didn't start off with this nice camera, all the mics, all the equipment. It started off with an iPhone. It just. It just started off with an iPhone. And then I look at that first business that I started. How did I get customers? I knocked on doors, I left flyers that I printed out and I just made it happen. There was no. It was just you had to go out and do the thing.

[Simon Squid]

This is the thing. I'm worth hundreds of millions today, but I still have to do the work. I'm building a new platform. There's no getting around it. I can't pay someone to be me doing stuff. You have to do the work, which is why I think you need a mission. I think you need a purpose, a focus, but you have to do the work. Too many people think that money means you don't have to do the work. It's the opposite. If you've got money, it doesn't mean the work doesn't get done. It means you still got to work. But people are too busy thinking, I'd love to outsource it. I don't want to do anything. I want a passive income. There's no such thing. That is one of the biggest lies I've seen. There's no such thing as passive income.

[James]

So you started to do some landscaping for a little bit. You found wealthy people with big houses and you set your rate when you were going out to them. How long were you doing that? And kind of, what did that pioneer into next?

[Simon Squid]

So the gardening company was my first big failure. So I actually managed to build the company up. I had 126 clients paying me a monthly fee to take care of their gardens. And I hired other people that were homeless to help me do the gardens because I'm shit at gardening. I didn't know that. I was desperate to make money. So when I started taking care of the first garden, I realized I'm not very good at this. So I brought people in that were good at it. So that's when I realized I know what my skill is. I found out for the first time what my skill is. And it turns out my skill at that time was knocking on doors and begging people to let me take care of their gardens. So I specialized and did that. I got really good at it. But then the business collapsed. And all because I didn't realize England has a winter. So the winter came and I didn't think ahead. My first big failure was me not thinking ahead. My first big lesson. I didn't realize when winter came, everyone stopped asking for their gardens to be taken care of. So I built this thing up. But here's the thing a lot of people don't realize about failure. Of course we all hear you learn from failure. That, that's true. But also like a bit, a bit weak of a reason to fail is not just for a learn lesson learned, right? The other thing, I made a lot of money before it failed. So luckily I built up a massive bank of money. So although it failed, I still made money. And on top of that, I had compound learning. Now, I knew how to hire people. I knew how to get people on board as clients. I knew how to service a client and make them happy and get them to recommend me. These were things I took into the next venture.

[Jack]

See, the two things that a lot of people that are watching this podcast could take away from that, right? There is one, you were at a position in your life where you realize no one's coming to save you. And there's a lot of people now that are out there that are just kind of like, oh man. Like, you know, the job markets, really tough, the economy, like, like it's just, it's tough for me to get a job or. But at the end of the day, like, it's really on you to like go out and make it happen. But then two, you can't be afraid to fail. Because even you said in the moments of you starting that first company, even if it didn't work out, like you learned so much along the way. Like, I know the three of us in starting, you know, we had entrepreneurial ventures before we started school, hard knocks. And I look back, if I had that conversation with my 18 year old self, I was like, man, I wouldn't change a damn thing. Because of all the lessons that we

[Simon Squid]

learned along the way, the biggest thing is follow through. People just don't want to follow through. And Then they wonder why they don't make it. You just got to keep pushing, not give up. By the way, you guys are three way partners on this, right? Which I think that's another interesting thing as well. Like you need one plus one equals eleven is how I describe it. A lot of people think that someone's making it on their own, but no, everybody I've ever known that's successful has done it in teams. No one can do it on your own. That's the thing. You know, in school they teach you, sit down, do an exam. If you get an A, you are success. If you're a D, you're a failure. That teaches you the wrong thing. Not, no one's sitting down doing the business on their own and successful. Nobody, everybody I know has so in the school system teaches you to that exam on your own. That's dangerous because that teaches you. I've got to be good at this. If we all did an exam now together, we'd all get an A. And that's what people need to learn. They need to learn to build a team. Like you guys have done. Like, I got 48 people full time on my team. This is, this is not me on my own. It's impossible. It was at first, me and the phone. That was at the very beginning. And then I had to bring in help. It's just impossible to do on my own.

[Josh]

Well, no, I was just gonna say that's what I love about the channel. And honestly, what was the inception behind the name the School of Hard Knocks? And I feel like really resonates with your story is the sense of we had peers who didn't have the same mentors that we had to show them, hey, these are the right ways to do things. This is the right ways you should approach career. And you kind of woke up one day and you said, hey, I learned nothing through the education system and I had to find out a way to make it on my own. So I know you started with gardening and winter came. What ended up being that next venture.

[Simon Squid]

Well, interestingly enough, I turned 16 by that point. So in England, you get a national insurance number when you turn 16. And by that time I got. I only was homeless for eight weeks. So I managed to have an address and a national insurance number for your US listeners. You need this number to get a job in England. So now I could get a job, which in a way was also a weakness. So I got a job in a hotel. The thing is, for the first, like eight months of doing that job, I actually Enjoyed it. Suddenly I had money coming in. I was working with people like I was part of a company. And I almost got addicted quite quickly to the job thing. And something just kind of re. Awoken in me, if that's the right. If that's even a word. Like, I just thought, hold on a minute, I'm falling into this trap. I know I can take an idea and make it real. So why would I work in someone else's business? Building them value? And so that's when I started something called Accommodation Express. I started another business, which, again, for your listeners listening to this, they're going to think, I sound like I'm 100, I'm only 50. But I basically was working in a hotel. And people were ringing up the hotel and they were saying, can I please book a room? And then the receptionist was really happily saying, sorry, we're full, because I've done a really good job marketing this hotel. So they put the phone down all happy, right? And I'm like, no, no, we just. We pay for that lead. And now we've lost that lead. We don't even know who that was. So I said, next time that happens, tell them we'll find them an alternative hotel nearby. This is before the Internet, right? So then I would then get them to give me their details and then we'd ring around all the hotels that were half empty because they hadn't done as good job as us. And we placed that booking in that hotel, make 15% commission. So it's called Accommodation Express. So I was kind of hotels.com before hotels.com so basically you couldn't take the entrepreneur muscle awakened in my brain off me. I after that. And so I basically started another business while I was working for someone else. And thank God I didn't fall into the trap of working for someone else.

[James]

I love that. And then the next venture was that,

[Simon Squid]

well, I sold that company and I got a little payout and then I got advice from, like, what should I do next? And then at the same time as I sold that company, my friend was living in Hong Kong and he said, hey, come to Hong Kong. It's like Hong Kong. It says, In 1997, when Hong Kong's about to be handed back to the Chinese, he's like, come and stay with me. Come and check it out. So I thought, okay, I've got this money and why don't I just go do a bit of traveling and have this experience of going to see a city like Hong Kong? So I literally flew to Hong Kong Only one friend there. As soon as I landed, my mind exploded. I sometimes describe it as like waking up, because I woke up first time at 15. I realized I could take an idea and make it real. And then when I went to Hong Kong, I woke up again because I sat on the harbor and you guys have been to Hong Kong. Anyone that's listening, you should go sit in the harbor front. You realize again that whole city was once in someone's head and they made it real. It doesn't have any natural resources like oil. It's literally someone's imagination and they made it happen. The whole city is created from someone's mind. And I sat there at a harbor front. I thought, holy shit, I'm so. I was so protected in a little bubble in England. I didn't realize how big the world was, how much opportunity there is. And literally my brain just expanded sitting there in Hong Kong. And I just was determined to start a business in Hong Kong and make it big.

[James]

I love it. It's like when you interviewed me, one of the things I talked about was when I went to 20 countries because our dad was in the military. Our dad ran the largest overseas military base in the world. So that took us around the world. But one of my favorite sayings is you can only grow to what you're exposed to, which is very true. Which is what happened to you and Robert Herjavec we were talking about before. He's got a saying where he didn't realize that you could own a private jet until he was 27 years old.

[Jack]

And.

[James]

And once your mind is fully contracted and expanded, it can't go back to its original size.

[Simon Squid]

I wish sometimes my brain could go smaller just because sometimes when you know too much, it can also. It's very hard to accept a normal life. And sometimes that can be, you know, I've got an eight year old son. Do you guys have kids? Any of you guys have kids? So that changed me chemically having a kid. And so like today, he asked me this morning to stay with him and play. And I said, I can't. I promise to go on a podcast. I've made commitment, but it's damn hard when you've got a kid to like, go ahead and still do these ambitious things. Which is why I say to young people, when you don't have kids, do it. Do it when you don't have kids. But when you have a kid, it's really hard to like, follow through, because I want to. My natural instinct is be with my kid now, protect Him. Right. But you have to take risk when you're young and you have to take risk when you haven't got kids, if you can, because it's a lot easier. But it's hard once you know the world, it's hard to. I have to build something big with my time to justify being away from him, but also to justify like the whole existence. But it's hard to explain to an eight year old that I'm picking this over him today. That's how he sees it. So yeah, it's a difficult one.

[James]

I wanted to ask, Right. You know, you mentioned that some of the skills that you adopted early on from the initial businesses was the ability to follow through. You were extremely persistent with your customers and the ability to hire. Were there any skills that you began to pick up when you moved to Hong Kong that you started to apply to some of those companies that you began to build?

[Simon Squid]

I think Hong Kong, it chemically changed me. So I remember I was there about a week and a son of a billionaire invited me on their family boat on a Sunday. And I remember thinking, I'm a stranger. Why? They invited me on their boat on a Sunday. In England, Sunday is the day you hang out with your family. And you're certainly not inviting people over. Right. And I was like, that's so weird. I went. And what I realized very quickly, the way a billionaire thinks, is that a Sunday is a day to socialize and make more business things happen. They're not separating work and life. There's no work life balance, there's just life. And so on that boat, I watched this billionaire and his son like, work and socialize at the same time. Now I got invited back, which was probably also like a good thing in the sense that I think they probably got a gatekeeping system. So they let you in and if you are someone of value, they'll let you come back. Right? So you've got to bring value. But my point is like, it changed me. I was like, normally for me, like, Sunday's the day I don't work. But even, even as an entrepreneur in England, Sunday's the day you got to have a day off. Why? If you're loving what you do and you're surrounding yourself with people you like doing business with, you like working with, why do you need a day off? And I didn't really figure that out until I moved to Hong Kong. I think the other side of it as well is like, your opportunities are as, as limited as your imagination. So on that boat, I remember them talking about building a building called the IFC hadn't been built yet. They're just like, okay, buy the land, we sketch out the project, we raise money and we build it. All right? Building a building 88 stories high isn't that complicated.

[James]

The International Finance Center.

[Simon Squid]

Right. But everything's simple. Like, there's no. Like when I speak to people in the street and I asked in the dream, the first thing people tell me when they can't do it is they don't have money. These guys imagine money, and that's what I learned from them in the first, like three weeks of being in Hong Kong.

[Josh]

Do you. Do you think part of it is an aspect of fear? Because I think one of the things that the three of us experience a lot is the fear of even though we're doing very well for ourselves financially, it's the fear of missing out what could be next. Or I still feel broke. Even though objectively I'm doing very well for myself, I still feel broke. But when you look at a man like that who's a billionaire, do you feel like they still have that fear of just missing out on opportunity if they're not working on that day?

[Simon Squid]

I think everybody is different, so it's hard to generalize, but I know exactly what you're talking about. And I think if all the successful people that I've interviewed, and you guys know because you've interviewed successful people as well, is like, it's not a one off. They're not just doing it for now. It's just who they've become. So it's like an athlete who just wants to keep playing football. Entrepreneurs, we don't have to stop because fitness itself, although it's an important part of probably being a successful entrepreneur, it's not key. Being an athlete, you have a certain age where you won't be able to play anymore. Not of entrepreneurship. Why would I not use this compound knowledge I have gained over the last 35 years? Why would I not use it? It's almost a waste of 35 years of work if I don't use it. Right.

[Jack]

To compound, it becomes part of your identity.

[Simon Squid]

Exactly. I don't subscribe to this like 5am Club. I think what I do subscribe to is I know my own rhythm. You cannot stop me. I will work all day Sunday if I have to, but if I'm tired on a Monday, I'll stop. Because I think the most valuable thing about being an entrepreneur is owning your time. And I never want anyone else to own my time. That's what drives me, I never and I still feel it today. Although there's very unlikely anyone will ever be able to owe my time, I never want anyone else to own my time. That is the most important thing to me.

[Jack]

I want to get into the, you know, the company that obviously you started in Hong Kong. But it kind of goes back to a point about like, hey, as an entrepreneur, you know, you almost get obsessed. Like I'd say like we've lost our mind to our business in a way. Like we're thinking about it all day long. And you know, for a lot of founders that end up going on to sell their company once it's sold, they kind of like lose themselves in a way. They're like, I don't know what to do and they almost kind of fall into a depression. Well, I know that you ended up exiting your company and I want to talk about that company for a bit. If you could explain what that was. But what was that kind of process like and what did you feel afterwards?

[Simon Squid]

Well, you have to understand for me at 15 years old being like desperate and then slowly building myself up when I got to 40 years old, I'd been working non stop for 25 years at a very hardcore pace. And so anyone that's lived in Hong Kong, it is another pace. You're working seven days a week non stop because you love it hopefully. But I basically got to 40. PwC offered to buy my company and I thought, yeah, great, this is the dream, right exit and now I don't have to work ever again. So my mindset was totally wrong. By the way, I had forgotten that retirement is a lie. And in my mind I want to retire. At the same time, my wife and I decided to have a baby. Perfect, I'll sell my company. I sold it for so much money, I never need to work again in my life as long as I don't live past 104. So very unlikely I was going to live past 104. That's it. I don't ever have to work again. And what I discovered is something that perhaps only getting a lot of money will ever teach you, but I wish I could pass it on to people. You sound like you've got it, which I'm kind of surprised by. Retirement is bullshit. And I did retire. Worst two years of my life from an emotional point of view. I had my son. It was incredibly beautiful. We had a beautiful baby. I love being a full time father, but I had no purpose other than my family. I had no reason to go up and Hunt every day.

[Jack]

Someone can fact check this, but I think that like the average age after someone retires is like five years before they start developing like health problems and pass away because they lose their purpose. Like, you know, our parents are in their 60s and I told my dad before he retires, I'm like, you gotta find a hobby. You gotta find something that is like. Because once you retire from the workforce, it's not just going to like going to play golf on the golf course. Like, you got to find something that drives.

[Simon Squid]

The truth is people know this already. If you think about, I can't say it anymore, BLEEP that out probably you think how many people were sat at home living the dream, doing nothing during the mental health crisis went through the roof. We're meant to do something, by the way. This is actually what scares me about AI. It's not that it's going to take away people's jobs. Some of these jobs are shit. I'm glad they're going. What I worry about is people need purpose. We need a reason to get up in the morning and do something. And what we don't want to happen is for people to be plugged into a meta device and sucked into a crappy universe and not do something with your life. We need to help people find purpose. That's going to be the problem in the future. Not right now. I think right now it's helped people find something to do that they love. But in the future, AI is going to take away people's purpose and that is really needed. And I, and I did have a mental health crisis during those two years. I sold my company. First six months was actually kind of amazing because I've got all this cash

[James]

in the bank for people that don't know what business was that.

[Simon Squid]

It was a combination of like a creative agency and a branding company. So we help people like CNN expand around the world. Outside of the us we helped Estee Lauder get into China with some of their products. So it was basically a strategy and branding company. And it did incredibly well and better than I ever would have imagined at the time when I launched it in 2000. But was my identity as well. That's the other thing. I was this guy that built this company called Fluid out of Hong Kong. Everybody in Asia knew me and that my, my whole life was tied to it. And then when I sold it, it was all in the news. It was very exciting. And I suddenly had this pile of cash in the bank, but I lost my identity. So when I would see people Be like, what do you do? I'm like, I'm a full time father. Which in itself was special. But then I felt like I wasn't learning anymore, I wasn't growing anymore. I wasn't taking all this knowledge I had and applying it. And I felt like I became a bit of a shell for a while. You know, it was nice at first to spend the money, but then slowly I realized, no, no, no, this is, this is not, this is not a good life.

[James]

When, when you set up shop in Hong Kong, were you there pretty permanently or were you bouncing back and forth between London and Hong Kong full time

[Simon Squid]

committed to Hong Kong?

[James]

Why is that?

[Simon Squid]

I met a girl. That helps. And I think I fell in love with the city. And then I, I also just enjoyed the cultural nuance of it. Because living in England, I'm sure people in the US as well, we have this. Sometimes we don't really leave our ecosystem. I think a huge amount, 70% of people in America have never left America. So I just think when I moved to Hong Kong, I had all these stories told to me about what Asia was like, like a backwards place. That's how it was portrayed to me. It was the opposite. It's like when you go to China now, people in America still think China's copying. I'm like, no, no, no, no. Elon Musk is copying the apps in China. Let's be clear. Elon Musk is copying China. Let's be very clear, right? And he should, because they're way ahead. But that's what I realized when I went to Asia. And so I just couldn't leave Asia. I was obsessed. I went all around the region just wanting to learn from what was actually the future. But I was told it was the past. You know, I was told it was the ex colony of Britain. It was a kind of has been part of the world. It was emerging, but not doing very well.

[Josh]

Completely opposite was was there things that you learned about business that was different over there? Because you look at America, people say America and how we do business is quite transactional. But when you spend time in the Middle east, they want to get to know you, break bread with you before they actually even talk about business. Is how they go about conducting business in Hong Kong different than how they did it in the uk?

[Simon Squid]

It's a fascinating question, that question. So how they do business in Asia is very different to how you do business in the West. So for example, the best way to describe it would be like if you read a book in China, you Read it backwards. It's still a book. So business is still business, it's still a book, but how you go about it is just the opposite. So in Hong Kong, for example, that billionaire I mentioned, we actually didn't do a big business deal for many years. And I spent many years supporting them, getting to know them, giving advice. There was no actual transaction financial, big financial transaction for many, many years. You build up trust and respect and then one day the floodgates open. Whereas I feel like in America, someone will do a deal with you quick, but they'll dump you just as quick. And so everyone's different. One thing though, I say, although there was business cultural differences, in the end what I realized is that we're all the same. They love their kids in Asia. My wife's Asian, she's from, from China. We, we love our kid, right? We love to eat food, we want safety, security, we want the best for humans. And what I realized slowly as I did more and more business out there, in the end it's actually the same. There are people in America that was when spend years getting to know you before they do business. I just think that in say Hong Kong, because there's more high net worth individuals, they're a little bit more discerning earlier on. So in the end what I realized, there wasn't that much difference. It's just because there's such a high concentrated level of wealth in somewhere like Hong Kong, you're dealing with much higher level people very quickly. So in America, again, I've tried to do business in America. If you go and deal with the high level people, it'll be exactly as I just described it. But I didn't know that when I first went to Hong Kong. I thought this was a unique thing for Hong Kong, but it wasn't. It's a unique thing for high net worth individuals.

[James]

I want to go back and touch on, you know, you mentioned selling your company, retired for two years and you struggled with some mental health for a little bit. I think that this is applicable to not just entrepreneurs, but also athletes and people that dedicate a lot of their life to something and then they have to kind of move on abruptly or completely. Whether that's retirement from something where sometimes they don't even have a decision. How did you end up finding fulfillment afterwards? Because I mean, we look at you now, I mean you're incredibly full of energy, you're bright, you're helping change lives. I mean, I would imagine it wasn't just getting into content right afterwards because that was quite some time ago when you had ended up selling the company. How did you kind of get your mindset out of that hole? If you can remember any advice to people that may be, you know, struggling with some of that identity crisis right now?

[Simon Squid]

It's a really good question and it's a complicated answer. I think we've got so fixated on money, we've forgotten what actually drives wealth. Often the main indicator of making money is you are solving a problem in the world. That's often you're bringing value to the world. That's often how people who make a lot of money, that's how they do it. And I think value comes often from a selfish problem you're solving or selfish need. So I started making content. I never thought it would be this big. By the way, weirdly, we also. 21 million followers. Really weird. I never thought I'd have 21 million followers. I'm the most followed business influencer in the UK on Instagram and TikTok. I never thought that would happen. That was not my plan by the way either. All I wanted to do very simply was provide knowledge to people for free that I didn't have when I was 15 years old. That's it. That knowledge I was not given. I asked someone for it When I was 15, I asked a business influencer for help. They said only if you pay me. And I didn't have any money to pay them. And I remember that pain. It took me four or five years to learn on my own when that person could have given me one week's worth of knowledge. No YouTube fairness could have been one week of knowledge. It would have saved me years of pain trying to build up businesses, right? But they didn't give it to me. And that when I, when I had that time to really reset myself, which so many people don't get, this chance I got to reset myself and say, what problem bothers me in the world and how can I solve it? And I remembered the pain of a 15 year old me. Why the hell, even today is the education system not teaching people about money, not teaching people how to communicate, how to sell? You can be an introvert and you can sell. You can be an extrovert and you can sell. It's teachable. Why are we not teaching it to kids? And that's when I went, no, this is not right. And all I did at the beginning, and I've never deleted a video, so you can go right back to the beginning. You can see I just started showing people what I know And I suddenly felt useful and I felt heard, very selfish at the beginning. And then I knew if I got this knowledge to one person this week, I could change their life. So that's all I was thinking about, helping one person each week. And sometimes the views were 1, 10, 50, 0. All right, but it didn't matter as long as I helped one person a week. I think too many people do think, how can I help 21 million, right? They look at us and they think that's what they want to do. That's beautiful. But don't beat yourself up when it's only 10 or five or six people this month because that still makes a difference.

[Jack]

That's a, that's a big problem with our generation that we see is that everybody wants the house on the hill tomorrow. They want the big following, they want the nice car. But they don't understand that for most entrepreneurs and people that actually or just anybody that achieves success, it really takes subscribing to macro patients micro urgency. It's going to take a long time. But if you do the things every single day with your head down in the sand like you're going to get there faster than you ever expected. But Simon, my question for you is how do you think we actually fix the traditional education system?

[Simon Squid]

I think we fix the traditional education system by changing the question we ask kids. So right now every kid in the world, because the education system is exactly the same everywhere we stop asking kids, what will you do when you grow up? It's a thing that traps a mind. It makes you. My 4 year old was asked this on his first day at nursery and he looked at me like what should I say to make the adults happy, make the teacher happy, make you happy? Daddy, what do I have to say? What shall I say? Should I say doctor? Should I say lawyer? What is it you want me to say to make you happy? He has no idea for what he's going to be when he grows up. I mean frankly, he's eight now. I think if he said a doctor, I think it's gone. I don't think there's even going to be doctors in 15 years time. There's going to be AI doctors 100%. People don't like to hear it. They get really upset with me when I say this fact. I'd rather have an AI give me a diagnosis because I know it's 100% accurate than a human that a bad night's sleep argue with their partner last night and today got it wrong, right? I want AI to give me the answer. And that's what's going to happen. And I think the thing is the question we should ask kids is not what will you do when you grow up? But what problem will you solve that opens up minds? I've written a kid's book and that is the opening statement in the kids book.

[James]

What's the name of it?

[Simon Squid]

It's called what's yous Dream? The workbook. People have to stop asking their kids and asking other people's kids. Even worse. What are you gonna do when you grow up? It traps kids, it traps them into this. Like go to university, do this, do this. I know people that are 8 years old will ask that question by the time they're 28 they've come out of university. It's not what they wanted. They're a lawyer now and they hate it. Right. Why the hell are we doing that to people? I reckon they're which we Del. I think the school system does it on purpose. I think it's trapping young minds to work for someone else.

[James]

You know what's so crazy too is that I've, I've. What's the statistic? I think it's like 70 or 80% of people, whatever, they get the degree and they, they end up doing nothing with that thing. Doing like do you think about how the endowment on these universities, billions of dollars that some of these universities have and they have that research but yet still nothing changes.

[Simon Squid]

They're going to come after us. I'm not joking.

[Jack]

You got to be careful.

[Simon Squid]

I'm telling you it's a big big business. The university system is a big big business. Hidden is like some in England today. Right now There are over 700,000 kids just in England come out of university to come out of university cannot find a job.

[James]

And I'm not cutting you off either, you know. So a lot of our content that we do is just like you cold going up to people and you know we knew a couple people coming out to London that we were setting some stuff up with but a lot of the time you know, we spent just going up to people cold out in Mayfair trying to find some heavy hitters out there, you know and for our audience that may be American, Mayfair is like the Beverly Hills of London. Well anyways I went up to a gentleman and he was a investment banker, now owns a hedge fund, very successful 58 year old gentleman. And he, and I was kind of poking at the question about like what do you think is more important today? What you know or who you Know, and he was saying that it's, it's, it's what, you know, I think it like one of the queens or princess, somebody's like daughter of like the royal family, can't even get a job. And he was saying how like back then it was, you know, so it just, it's fascinating.

[Simon Squid]

Well, these kids have come out of university here. I mean, I know America's university system, you can get all sorts of ways of paying for it, but all of those kids are in huge debt, so. So you can get US$100,000 worth of debt to go and do a four year degree. That is fucking useless when you come out the other end. But if you want $100,000 to start a business, fuck all out there, right? We're funding people's businesses right now. Like independent businesses like mine are funding people's dreams because there's no money for them. Only if you go to university and get into debt will they give you all this money. And you don't, at 19 years old, you don't know because you've never been taught about money, what you're signing up to. It's actually criminal. And I think people are going to these four year degrees because they don't know what else to do because they're told when they were eight, you want to be a lawyer, this is the university you need to go to. And then you come out the other end, you'll have a job.

[James]

Which I think brings us to a really interesting next question. Because you're somebody who's amassed well over 20 million followers, hundreds of million, billions of views across social media. You understand the Internet business game as well. And there's also a massive debate and discrepancy about people that are selling education online. I want to get your take on the whole, what we like to call is kind of like the wisdom economy, where there's people that are selling information, whether it be through courses or masterminds. How do you feel about that as an external piece of education for people as opposed to going to university? I want to get your take on the people that sell courses or coaching your information. Give us.

[Simon Squid]

So I got, I got a lot of hate, I got a lot of hate online about this one. So I'll be a bit careful with this because I think it's very important. You know, sometimes when we clip things up, people misunderstand what you're saying. So, okay, my personal story of not getting help when I was 15 years old because I couldn't afford it, the line you hear A lot is if you don't pay, you don't pay attention, right? This is not true. What makes people pay attention is pain. Okay? So, you know, we all know people that are paying for the gym, but they're not going. Why? Because it's not enough money for them to go to the gym and. Or probably they go to the gym if they had a mate they were meeting in the morning to go to the gym, right? The pain is letting your mate down, not losing 50 quid a month or 100 US a month for your gym membership, whatever it is, right? So why remember that feeling so badly of not being able to afford it, desperately needing it, but that person telling me, well, if you don't pay, you won't pay attention. Like, you won't appreciate it. So my take is like, free has a huge amount of value, if you put value in free. And so my personal mission is to provide huge amounts of knowledge to people for free. So I have the most popular business video, YouTuber told me on YouTube about business. 2 hours and 26 minutes, 16 million organic views. And so that whole video was originally, I did it to answer my DMs. Of all the questions I get. Someone said to me, you can make £20 million by cutting this up into a course. 4,000 people paying $4,000 and everyone will do it. I've got 21 million followers. I can get 4,000 people paying $4000, right? But I thought to myself, yeah, but what about all those people that can't afford it, that won't have the knowledge and they'll struggle today? So I put it up on social media and it's made, I think we're coming up to $850,000 off that video. So it's not 20 million, but if you go look at the comments, we've changed lives releasing that information for free. And then we created a trend. People copied our video and everyone started doing all their knowledge in X amount of minutes. I don't know if you guys saw this, but we created a trend where people just released all their knowledge. And the truth is, by just releasing all your knowledge, you also get more followers in the end. Like the book, right? You don't make money out of a book. You make money out of the fact you've got a book. And I think that a lot of people, if you look at Facebook, for example, imagine if they charged a fee to sign up on Facebook. How big would it be? It would be limited Instagram, if you charged for people to sign up to Instagram. How big would it be? I actually think there's a business case that free, in the end has more value. Now, there are people friends of mine that sell courses. They bring value. I have no problem with it. Like a friend of mine called Ali Abdaal, he makes content that helps people. He sometimes charges for, like YouTube training. Everyone that goes through those things comes out the other end saying, that was worth my money. I got no problem with that. The people I have problem with is like the HS tiki toky this shit that these people sell where they promise get rich quick and join my trading this and join my crypto that, and it's all fucking bollocks that. I have an issue with people that sell property courses that apparently so rich from property, they're selling some course to some kid about how to get rich through property. I'm like, no, no, no. You make money selling courses on property. You're not rich, otherwise you wouldn't sell the course to these kids. You give back and help them. Right. So it's those that lie about their success sell a course about selling a course. That pissed me off.

[James]

Yeah. It's the person that built the E commerce store to, you know, $100,000 in revenue, but no profit. But yet they're saying how to make a hundred thousand dollars.

[Simon Squid]

Yeah. And that's actually making all their money from selling some bullshit how to get rich doing E commerce. Right. I think courses can have value. I always say to people who sell courses, I'm not your enemy just because I believe in free. It's my personal backstory, that's why. But I think that free can have value if you put value in free. But a lot of people who give free and say, oh, no one turned up or no one took value. No, you didn't put value in that. I have not had anyone not turn up to my free webinars because I bring value in them.

[James]

Right.

[Simon Squid]

But some people deliberately don't put value in free. And then they reinforce this lie in their head. Oh, free people don't value it. No, you didn't put value in free. That's the truth. So they reinforce their own bullshit.

[James]

But this is a business where you've invested in 81 companies.

[Simon Squid]

Yeah.

[James]

I want to just kind of ask you, among all the companies that you've invested in, what would you say are the most common patterns that you've seen across not just the businesses you've invested in, but also your own, that have really led to a ton of success for those business businesses?

[Simon Squid]

So every business that I've invested in the 1. When I analyze what succeeded and what's failed, the common thread which has made me a better investor in businesses now is the person who's put the business together and is pushing it. Number one, they never want to sell it. They're not building it to sell it, because if they get stuck with it, and I've been involved with people that want to sell it, they get stuck with it, it dies. So you want to build something you're never going to sell. Now, you might sell it because the offer is too good to say no to, but you're not building it to sell it. The second thing is they've solved a problem that bothered them. So, for example, I recently invested in a business called Lovable and we got in early, it's now worth 6.6 billion. And this company's fastest growing revenue business ever in history. And the people behind Anton, who runs that company, he wanted to help a friend of his. He kept asking him, I need a cto, but I've got an idea, I need a cto. And he is a technical person, but he didn't have time to help his mate, so he built a product that was basically a CTO in your pocket. So you don't need a cto. So his mate would stop bothering him. I need a cto. And of course, if you can make a technology product replace the cto, how big is that business? And now you can voice click what you want and the app builds it for you. An app that builds apps, I mean, it's mind blowing, isn't it? But he didn't build it thinking, I'm gonna build a billion dollar company. He built it to solve a problem that he was having. And most people I see that are successful like my business, it will be incredibly valuable if it's not already because I'm solving a problem that bothers me. The education system is letting people down. It's not giving people freedom to follow their dreams and follow what they love. It's hurting people and I will not stop until it's fixed. And how big is it? If you fix the education system, what do you think that business is worth?

[James]

Billions. Billions.

[Simon Squid]

Yeah.

[James]

So you mentioned that you look for people that don't, don't start businesses to sell them. Did you have that mindset with your businesses that you founded or did that just kind of come over time?

[Simon Squid]

I never really thought that any of my businesses were sellable. Every time I got my first business, which was Accommodation Express that I sold, I wasn't Looking to sell it. Someone just said to me, I really like this idea, I'll buy it off you. I was like, okay, I'll have that experience. It wasn't a lot of money at the time. I saw the selling of it as an experience, but I didn't build it to sell it. And then fluid the business I built out of Hong Kong. This business was throwing back cash to me and I was actually using the business to make investments in businesses. So I didn't need to sell it. But that's the best place to sell a company. You get the highest value out of a business when you don't need to sell it. The best time to sell your business is when you don't need to sell it. The best time to sell your business is when it's really growing and doing really well. Most businesses that raise money and most businesses that sell for a lot of money aren't looking to raise money and aren't looking to sell because you're in a sales position. I'll give you a load of money for you. Mark Zuckerberg, right, had someone go to him from Yahoo saying, we'll give you a billion dollars for your business. He said, no, I don't need it. What would I spend the money on? Oh, we'll give you 2 billion. No, I don't need it. 3 billion, that's okay, I'm alright. 4 billion. You say like it's because you don't need to sell it and you don't want to sell it.

[James]

So you can't be in a place of desperation ever.

[Simon Squid]

100% you don't want to be there. That's why I say build a business that you love and that you enjoy doing the work like you love what you do. I can see it. So if someone bought your business and told you you couldn't do it anymore, ever, would you sell? See what I mean? Like that's if it's a bit cliche. I hear a lot of people say, you know, and billionaires, by the way, who don't agree with me, My fellow colleagues who don't agree with me, they don't say this. They say, find a niche, build a business in that niche and you'll make lots of money. I think that's the old way. I think now, thanks to social media, you can do something you love and eventually it will make money. More importantly, you'll enjoy it, right? What's the point of having a horrible 10 years of life not enjoying what you do, just in the hope that your business will Be worth money. Enjoy the process. If you love fishing, go live fishing every day.

[Josh]

We sat down recently with a gentleman named Richard Harpin. He sold his business for over $4

[James]

billion, which was, by the way, he went £4 billion.

[Josh]

And he talked about selling your business, getting investors. And he said that when, like you said, when the business is struggling, that's the worst time to ask for money. Because people can get a much higher value, like a much lower valuation to get more equity in the company. And for someone who has a company that's doing well, it's spitting off cash. And maybe they've been bootstrapped. If now they want to take investors money, is there things that they should look for in a potential investor that would be like, okay, I don't want to just take anyone's money, but I want to take the right person's money. What are some of the things that they should look for in that strategic partner?

[Simon Squid]

So I'm going on Shark Tank soon, and I've warned the producers that I might be a bit different to the other sharks, okay? Because I think people are pretty dumb to take investment from people, just money. Because money is in so much abundance most of the time. If you want more money, just get more sales. And the truth is, most of these TV shows are bullshit. People go on those shows really for the marketing. That's what people watching it don't realize. If you get more sales, you make more profit. You don't need an investor. If you sell more of what's profitable, you win. So why would you give 20% of your company away to some twat who's got money? The only time I think you should ever sell equity in your business is if the person coming in can 10x your business. It's the same reason I invest in businesses and not in the stock market. I buy equity in businesses because I can add 10x to the value of that company, because I can apply my skills to that business. Whereas if I buy tester stock, can I really move the needle on Tesla stock? What can I do? Buy Tesla, Post it on my social media? Maybe not really. Elon Musk can move the needle of Tesla. That's why he's invested in Tesla. He's not the founder, he's an investor in Tesla. Right, Same. I think you should invest in things where you can move the needle, not buy stocks and shares because you can't move the needle. Why would you waste your time putting your capital into something you can't affect the outcome? In fact, bigger risk of it just Going to zero because you can't affect the outcome. So I think that a lot of the time that's the thing people need to realize you want an investor who can move the needle. So in my company, there's only 10 people in the whole world that I would let invest in my business because they can bring something I don't have, which frankly at this stage isn't many people. Right. I can bring the media myself. I can Collab with you, Mr. Beast, I don't need anybody else's media. So Rupert Murdoch, I don't need him. I just don't need him. And my media is bigger than his media from a reach point of view. So the only people that can bring value, perhaps expertise. For example, I'm now doing a coffee brand. It's coming out of a global distribution system. So there are a couple of people in the world that know that really well, used to work at Starbucks. Those are the sort of people I would let in because they can bring value. That is supply chain that I don't have. But I don't need their money. I'll take their money as commitment to the process, but I don't need their money. And I think that's where you want to go with your mind. If you think you're bringing an investor in and it's just for money, good luck, you just got yourself a new boss. But if you bring someone in who brings money and then they build a skill set you don't have into the company now you have scale.

[Jack]

Simon, when you were going through that two years of, after you sold your company, going through that reset, when did you get the idea to start asking people what's their dream?

[Simon Squid]

Basically it was a process and I don't know what it was like for you guys with your, I guess, hook, but originally I was making talk to camera content and after about six months of telling the camera and therefore the audience what I knew, I kind of ran out of things to say now, you know, you. I told people how to raise money, how to build a brand, how to hire people. Yeah, I was talking heads. Exactly. Yeah, yeah, yeah. Which is why I think we all start a little bit. I don't know, like that's.

[Jack]

We started doing that too. The three of us were making videos, talking about business as some young guys in our 20s.

[James]

And then we were like, nobody wants to get business advice from three young 20 year old boys.

[Jack]

Yeah. We quickly realized that it was like, hey, like, you know, we went out and tried doing an interview and it got way more views than our other content. And so we were like, guys, I think people want to hear other, you know, us channel the business advice from others and not ourselves. But yeah, that's.

[Simon Squid]

So that requires you to swallow your ego. I hope people pick up on that.

[Jack]

It does.

[Simon Squid]

Because sometimes, like, no, no, no, we know what we're talking about. But now they want to listen to you because you built something on top of that. You've got the knowledge of the people in your network. That's perfect. I guess with my Talking Heads content. I found myself bored of my own content after about six months. And I one day I went live on TikTok and they just launched a new feature on TikTok where they could people tip you so they give you gifts. And it was the first day that TikTok gave money. The gifting system came on and when I closed the live, I made 150 US dollars. Now, remember, I promised not to charge people for help. And in my mind, and this is a mistake, actually, but in my mind I was helping someone on the Live, and then I just got paid for it. Now, it wasn't paid by the person I was helping, but somehow I made money from helping someone and I felt guilty about it. I've changed my mindset around this now because we make a lot of money from the social media. I just use that money to help people now. But my point at the time was like, I got to go give this money to someone. I shouldn't have this money. I'm supposed to be helping people without a catch. Now I'm making money from the social. So I went out into the street with the idea of giving that money away. And I actually went to get some lunch. It's a long story, but I went to get some lunch from a local supermarket and as I was looking for the sandwiches, there was a lady filling up the counter. And so I just turned her and I just said off camera. I didn't have a camera with me. I'm just like, what's your dream? You know, what would you love to do in life? And she told me this incredible story about how she'd like to open up a care home because her mother died alone at home and they didn't know for a week. I was like, wow, this is such an interesting story. And I was like, shit, I wish I recorded that. But I basically gave her the money there. And then, like, I want to. I want to go to your care home later in life, you know, like, I'm putting a deposit down. And I thought Shit, I should have recorded that, you know, like, that was incredible. So then I went and to another place right after, but this time I held my phone to my chest.

[James]

What year was this?

[Simon Squid]

This is maybe I'm losing track of time now. I want to say three years, Three years ago, maybe, maybe four. Four years ago. It's gotta be at least four years, isn't it? I'm losing track at least four years ago. And I just asked the person as I walked into this place, you know, what would you like to do? You know, what would your dream be? Sort of thing, what business would you start? Sort of thing. And they started telling me this idea they had and I gave them some money and this video got so many views, I was like, hold on a minute, this is the next step. Because what I found is I can give people all the knowledge in the world, but they don't take action. Whereas if I show them someone just like them that's just hasn't got a lot of money, is working somewhere, they don't want to be working, but they then make it happen. It's not me telling them how to do it, it's me showing them how to do it. And that's when I thought, shit, this is a winning formula. And then the rest is history.

[James]

Simon, I'm curious because I want to get your perspective on this. When you were coming up on through content, and let's maybe go back to when you were millions of followers less, and, and now, right, obviously we've seen you collaborate with some of the biggest celebrities in the world, billionaires, amazing people, and obviously the organic, I don't know about you, but the organic content's the best. When you go up to people, like the stuff that's not set up, that's always the best content right there. But, but anyways, I want to get your thoughts on. Were there some people that you had maybe wanted to collaborate with and they

[Simon Squid]

didn't want to do it or that well, Mr. Beast, I, I, I wanted to collaborate with Mr. Beast three, four years ago because I, I saw what he was doing on the philanthropy side and I felt that stuff was always a little bit overlooked because of the, you know, hold the car, last person to take their hand off the car wins the Lamborghini. That stuff got all the, all the praise back then, but I could see the philanthropy stuff, which was very aligned with me. And I tried for years to get through to him. I think eventually I did. And now we're doing a collaboration, which is, which is amazing. But I felt like, how, how do I work with someone who's got 400 million followers? And I think that's the thing. If someone's listening to us, we've got 21 million followers and they want to collab with us. Just don't give up and keep, keep pushing through. I swallowed my own ego as well, by the way, because last time I saw Mr. Beast was in Dubai and I went up to him and said, what's your dream? And his security guards pushed me out the way and told me to piss off. But I didn't stop pushing until I got through to him. And then when I actually met him, like we're talking now, it's like, yeah, let's do something, let's do it. So a lot of people are gatekept. You have to push through that pain and get through. Right?

[James]

I'll tell you what, man, a lot of these people have gatekeepers, man. It's crazy. Like, I think about when we did the interview with Tom Brady. You know, it took us a long time to do that one. But it's because these people, man, they've got. The gatekeepers are real.

[Simon Squid]

Yeah. Often the gatekeepers, their job is to keep you away. But once if your purpose is pure, you will get through. And I think the thing is, like, when I finally got through to Mr. Beast and he knew what we were doing, it's like, it's so aligned with what I'm doing. Let's do it like there's no competition. This is one of the things I love about making content. Like, if all my followers follow you, it doesn't hurt me. It's good. And in fact, I'd love that everyone following me go follow these guys. It doesn't hurt me. I love the content business because of this. Collaboration is how we all grow. A lot of people don't realize this. I met someone earlier who wants to be a content creator. Been doing it for a year. They're not getting any traction. I'm like, you've never done a collaboration with anyone else. Half the reason I'm successful today is because I've collabed with people and cross connected.

[James]

You want to know something that he just said right there though, that I want to point out? Because we talk about this all the time. You said something beautiful. That is a valuable lesson. You did not stop until you got straight to Mr. Beast. You have to go to the. You have to go to the decision maker. You have to go to the.

[Simon Squid]

You know, we might be breeding a bunch of stalkers here just to Say, one thing I would say though is you have to come, but you have to come to the table with value. So sometimes people get frustrated. Like people will DM me and I don't get back to them. First of all, I don't know about you, but I'm getting about 5,000 DMs a week at least. It'll be a full time job. Just go back to my DMs. Right, but people have to understand, bringing value to the people you want to work with, don't just go to them and say, help me. That's fine. You might get away, might get lucky. But the reality is if you can bring value to people, then they will respond. And it's commercial. But it's true. If you go to someone and say, Look, I've got 21 million followers, I'll promote you and support you. That's value. Right now, earlier on, maybe you can just help them with their social media, for example. There's a lot of very successful people that need help with their social media. And if you just go there and bring that value to them at one point, you can ask them for something back. Yeah, but a lot of people chase you, expecting you to provide value to them, but not understanding that you have to provide value to the person you're chasing.

[James]

Tony Robbins said it best in the interview we did that. We're all equal as souls, but we're not equal in the marketplace. Your job is to become more valuable and add as much value you can as other people.

[Jack]

And I'd be interested to get your take on this, Simon, but one piece of this that we've kind of added into the equation that we actually mastered in, in a way early on and getting people to talk to us, to open up and do the interviews when we were doing it on the street. But we kind of have a, we have a saying that, you know, James has mentioned in our interview sometimes that credibility kills all bad attitudes. And so when we would go up to people even early on where we didn't have like a ton of followers or credibility, we just, when we would give our pitch to people, we would try to lean on. What is the, like the number one thing that we could lean on that people would recognize us for instead of thinking that we're just some kids doing something for TikTok, trying to get interviews? Well, we had been going to the University of Texas at the time, and so we'd be like, hey, my brother and I, we started a channel at the University of Texas and we've interviewed Mark Cuban. And so and so. And like those sort of things at the beginning are. Even though it's just like, hey, like this, this is my purpose and mission. But just attaching yourself and some credibility to something that the other person, it is valuable to them to speak with somebody that has maybe interviewed Mark Cuban or is going to somewhere that they know they recognize. So I don't know if that came across with yourself doing the interviews.

[Simon Squid]

I think you're touching on something here. It's also very interesting what you do in your content. And I also do it that people don't quite understand is why do billionaires talk to you and why do billionaires talk to me? One thing a lot of people misunderstand rich people. A lot of rich people want to give back. A lot of rich people want to help. And I don't think enough people champion this within, like the community. Rich is very vilified, especially in England right now. I know it's the same in America. It's almost like some people that are rich are somehow evil. Not be my experience, my experience has been that. And so what I've seen with very, very wealthy people that I'm also working with is that I want to fix the education system. So do they. Now, not everyone wants to fix the education system, so they're less inclined to work with me. But those that do will support you. You do it in your content. You're like, we're helping young people, you know, entrepreneur channel, helping young their dreams. Right. That is going to excite though the rich people because they want to put the ladder down. Now, some of the rich people have no time and they would love to work with you to do it because they don't want to do the work or they're busy doing something else. But that's the thing as well. If you figure out what someone who's wealthy is trying to do and if it aligns with you, if you can get through to them, they'll definitely support you. It's not just about what value you can bring them, it's also what value can bring their mission. So again, if anyone can fix the education system, I'm investing businesses that fix the education system. So once you understand who I am and you pitch to me something that I'm trying to do, I'm likely to invest in it. But if you pitch me something that has no relevance to my mission, I'm likely to just have to ignore your dm.

[Josh]

I think that's so interesting as well as to how people with money get villainized in the sense of a lot of the times the people who are ultra successful are self made. They are people who have actually created the wealth, the wealth themselves. And I look at it like growing up I would drive down neighborhoods and I'd go to look at all the nice houses. I'd always wonder myself what do they do for a living? And now thanks to social media, you can start to find out through channels like ours what these people actually do and what advice they have. And when you talk like about changing the education system, you said that you didn't learn anything during your 15 years or your 13 years at school. You have an 8 year old now. What are some of the things that you're teaching your son that you weren't taught in this school? Excuse me, what are some of the things that you're teaching your son that you didn't learn in school?

[Simon Squid]

Everybody needs to understand home education. I home educate my son. I cannot be a hypocrite and say the school system is broken and put my own child through it. And what I have discovered, home educating, is that it's actually how we used to educate. Right? Think about it. We used to live in tribes on average size 500 kids weren't put in a classroom. 30 kids in a classroom, all the same age, all learning something whether they like it or not. If I pitch the modern day education system to anybody listening, you guys will be like what? That's crap. They're all going to have to learn what we teach them, not what they're interested in. And they're all going to be the same age but probably at different stages of development. But they're going to have no choice but to learn what the teacher or whatever the school systems told you you've got to learn or what a joke. I don't know about you, I'm an extrovert, but I do not want to be in a classroom all day long with screaming kids all day. Right. I don't want it as an adult, I don't want it as a kid. I think personalized education, this is what I've learned with my son. My son has certain interests, right? Right now he's really weirdly interested in sword fighting. He loves to get a sword. He's watched a bit of Star wars, he loves to do a sword fight. Now when we're talking about sword fighting, it might not seem it's linked to anything, but suddenly he's interested in how did Henry VIII get his sword. How much did Henry VIII's sword cost? Where did it come from. Suddenly he's into engineering, how the sword was made, economics, how he paid for the sword. He's into war because Henry VIII invaded a few places. You know, like suddenly we're discovering all these things that if I told him, I'm going to teach you history today. Shut up, sit down, I'm going to teach you history, he wouldn't be interested. But because I've come from the source of what he's interested in and then we follow where that path takes us. He loves learning. He knows more about history than I would say any like 18 year old to study history for the last four years because he's following his interests. It's so obvious when you hear it, isn't it? All I do is feed his interest. That leads to a whole slew of education. And you cannot force people to learn stuff like entrepreneurship to me is a way out of working for someone else. I wanted to learn it. Right? And I think that's the thing. I didn't, I didn't, I didn't just, I didn't just get it forced upon me. And I think that's the problem with the school system. Sit down. Today you're gonna learn biology if you like it or not. Right. It's no relation to actual real life or what I'm interested in. And that's, that's gotta change.

[Jack]

Just remember the mitochondria is the powerhouse of the cell. Just, you know, just, just in case you need to remember that today. Yeah, it's like a common, like when you're growing up in biology in the US that it's always like the, the mitochondria. First fact. Mitochondria is the power.

[James]

It's like biology, you know. Thing I wanted to ask real quick about, you know, what we were talking about prior to this about wealthy people and just them being willing. Right. And you mentioned your experiences. I would say 95 plus percent of our experiences is the exact same way. Oftentimes the richest people that I know are the most willing to help people. Especially because they also recognize that they were a lot of people. I 100% like. You're a self made man. All of us are self made. But there were definitely people along the way, mentors, people that we met that helped expose us to things, helped consult us on things that we're able to help significantly.

[Simon Squid]

Right.

[James]

And I feel like a lot of people that get to the highest level of success in their industry, whether it's social media, business, they realize that. Do you think that there's kind of like an obligation that we have as people to give back to other people.

[Simon Squid]

I guess there's no obligation. But what I have discovered, sometimes when I talk about this, people might say, well, he's rich, so he can talk this way. But I discovered something, getting rich that I wish I'd known when I was poor, which is you get so much joy out of helping someone else. And so anyone that's ever given someone a present, for example, you just think, you go out, you find it, you wrap it, you give it to them. That whole experience of, like bringing joy to someone else, it's actually really special. Now, getting a present is nice, but sometimes it can be awkward. Giving a present is what. That's actually what makes us happy. So I would say, like, we. We've kind of got taught the last 100 years and this happened, by the way, when the tax system came in. Give and take. I'll help you if you help me. This is the tax system was. This was brought around when the tax system came into place because they wanted to track everything to make sure you were taxed. So if I help you and then you help me, there's a tax tax event. But if I help you for free, there's no tax revenue. So give and take was designed to make everything a transaction. I'll help you if you help me. But the truth is, what actually makes us happy, our factory settings is give without take. I help you because I can. And this comes from tribalism again. 500 people in a tribe, someone's tent falls over, right? I will go and help them with that tent because if my tribe's happy, I'm happy. It's not because I'm going to get money out of fixing your tent. People have got confused. I help you with your tent, then you don't have no home, Then my tribe is happy. And then when I need help in the future, there's someone there to help me. This give and take mindset has become normal for us. It's not normal. What's normal is give without take. And I learned this when I had so much money that I could help someone and didn't need anything in return. But I have helped people understand. If you help someone for five minutes today for free, you just help them share their business on your stories and tag them. Just do one kind gesture. I promise you you'll sleep better. Because it's actually what we're meant to do. A natural thing is help someone and not expect anything back. I don't know about you, but I made a Mistake. When I was younger, I lent money to my brother and then he didn't pay me back and I fell out with him. 15 years. What I should have done is given them the money and not expected it back. So I didn't give without take. I gave and had an expectation back. And that's when you get upset in life. Most of my moments in life that haven't been good is because I had expectation when I helped someone. The most freeing thing that I've ever learned in the last six years, if I give one thing to people in this podcast, is like, we're not meant to have a transaction every time. We are just meant to help someone today and not get anything back. And if you do it, you will be happier.

[Jack]

Simon and all, all the people that you've, you know, asked what's their dream? Are there some commonalities across people that you've talked to as far as just like for them, what feels like the, you know, I know I'm sure money is probably the big one, but are there any commonalities maybe from their, from a mental thing or like a mental block or something that you see across all the people that you've asked what their dream is that is stopping them from achieving that?

[Simon Squid]

A lot of people that ask, what is their dream? One of the worst answers is to be happy. Because I think happy is a fleeting thing. Like, I was happy this morning when I hugged my kid goodbye, but I was unhappy when my public transport was a bit late. You know, like, if I want to be happy all the time, I'm likely to be miserable all the time. I think what I tell people when they say they want to be happy is doing something you love will both be make you unhappy and happy sometimes simultaneously. The best thing you could chase is purpose giving you a reason to get up every day and do something that's meaningful, something you enjoy that is going to. I owned a really successful business, right Fluid, in Hong Kong. And then one day the cleaner didn't turn up, but we had a really important client coming, so I went and cleaned the toilets. I wasn't happy that day. The client came in, we won the work, we made a million pounds profit from the work. I was happy because my business was successful. You see, I was unhappy because I was cleaning the toilets and I was happy because I won the business. But I was measuring my life on happiness. I would be average unhappy.

[Jack]

I had somebody had asked me one time, it was just like, well, what else would you be doing if you weren't building School of Hard Knocks And I said, you know what, it's fascinating that you said purpose because I even said like I would rather have, and this is kind of going to sound crazy to some people, but I would rather have a like what you would call a bad day working on School of Hard Knocks, which is, you know, the purpose versus like a good day or like a great day on average, maybe working a job for like a corporate job that like I didn't want to do every day.

[Simon Squid]

But anyone that's actually gone and followed their purpose knows this. The problem is telling people that don't know it yet. How you get that knowledge to someone, what you're talking about there, Because I meet people and we all have. I also meet a lot of very rich people that are very unhappy because money in itself doesn't make you happy. I know it's a cliche. I think doing something, I actually think how you make your money matters more than how much money you make. So for people that make money, but they do it the bad way, like these negative influences, I think they end up, you know, under house arrest, know, likely in jail. They don't have a good life because I think if you, if you make money the bad way, it comes back at you. So I think doing what you love, sometimes you're gonna be unhappy doing what you love because someone might be earning more money than you. For the longest period of time in my early years, all my friends went to university, all my friends were earning more money and I didn't have a big fancy car or a big fancy home. They were buying these things. But now those same people are trapped in a job they hate and they have possessions that own them, whereas I own my possessions and more importantly, I own my time. But when I was younger, I didn't see that. I was jealous. They've got a nice new car, they got a nice new house. I can't get these things, I'm self employed. But I didn't realize how much value I had because I own my time.

[Josh]

Is that a flip that you had as you continued to grow up? In the beginning especially, I feel like at our age right now, as you see these people have these nice new car, the new watch, the new house, whatever it may be. And you're like, I want, want those same things as well. But then you look at it is if I make that money work for me, whether it's put it back in the business, invest in something, but I can own my time ten years from now, is that something that flipped for you is like, hey, the ultimate goal of money is not to just have a lot of money, but it's to actually have freedom to do what I want.

[Simon Squid]

When I sold my company and I sold everything and I left Hong Kong and I moved back to England and I bought a really nice house in Hampstead, North London, by the way, it's better than Mayfair. You should probably go up there. It's where Ricky Gervais lives and all the, all the celebs lives. I moved next door to Ricky Gervais. And what I realized when I moved up to North London and started living like this, kind of like, let's call it retirement life. I'm 40 years old, I don't have to work ever again in my life. I bought my house cash outright, so I've got no mortgage. The guy we can, Gervais, one side, this other guy, the other side, this other guy, the other side. He was basically a banker. He's up at 6 and he doesn't come back till midnight every day. Also in his 40s. And I thought to myself, when I was younger, everyone was telling me, be a banker, right? You can be in finance, you'll make so much money from salary. But what he'd done is he got a salary and every time he got a salary he bought a bigger house and this and that. And basically he's got so much debt that he has to go to work and sell hours to make money. So he's not seeing his family in his 40s, but in his 20s. I didn't know this guy in his 20s, but I spoke to him, pretty sure, you know, he basically showed off his car on finance, he showed his fancy flat on finance. But the salary pay for these things because debt traps people. I actually don't think there is good debt. My father had good debt and it killed him, right? It's not. There's no such thing. I think debt traps people. And what I notice when people have a job, they can borrow money and they borrow beyond what they can really afford. And they buy these things as they think that's going to make them happy. What they never own is their time. I remember thinking, thank fuck I started a business at 15 years old because I wouldn't be 40 having to go do a job I hate from 6 in the morning till midnight every day and be away from my family at 40. Because I think if you do the hard thing now, life's easier later. You do the easier thing now, like get a job with a salary. Life's harder later. So do the fucking hard knocks thing now.

[James]

I love it. Simon. We like to end these podcasts off with two questions for our guests. I'm gonna start, and then Jack will finish things off for us. So, Simon, if me and you died tomorrow and you had one last message that you could leave with the younger generation, what would that be?

[Simon Squid]

The purpose of life is a life of purpose.

[James]

I love it.

[Simon Squid]

Yeah.

[Jack]

That's beautiful.

[James]

The purpose of life is a life of purpose.

[Jack]

And, Simon, it's been incredible going through, you know, your journey on. On this podcast today and us kind of getting to share some insights. But for you, how do you want to be remembered?

[Simon Squid]

I want my son to know that there's no one more important to me than him and that kids don't do what you say. They do what you do. So I left him this morning because today on my live Stream, we help 24 people follow their dream. It's worth it. So I'm making the world better for him later. And just as important, I want him to help people as he gets older and not do give and take, do give without take. And the only way he's going to do that is not by me telling him to do it, but it's by me showing him how to do it.

[James]

Simon, this was incredible, my friend. It was a masterclass. I love you guys on many fronts, man.

[Simon Squid]

One day we should just merge the businesses.

[James]

Let's go. Hey, hey, hey.

[Simon Squid]

School of hard knocks dreamers. We'll come up with a better name. Hey, hey, hey.

[James]

We'll go out and buy DreamWorks, right?

[Simon Squid]

Yeah. All right.

[James]

Do it.

[Simon Squid]

DreamWorks.

[James]

Everybody watch.

[Simon Squid]

We're not associated with DreamWorks at all, everybody.

[James]

Right now, guys, be sure to like and subscribe for amazing content, amazing episodes coming every single week to the school of hard Knocks podcast. We. We're going to put the links down regardless, even though you all know where to find Simon across social medias. And you've also got a couple books that you've written in what's your dream? Incredible book telling all the lessons that you've learned and helping people achieve their dreams as well as what's your dream? And this is what was the second one that you wrote?

[Simon Squid]

What's your dream? The workbook.

[James]

Kids book the workbook, my friend. So. And we got to be on the lookout for you this summer, man. You're coming to a show for everybody to watch.

[Simon Squid]

Yeah, yeah, I'll be in America very soon.

[James]

Any. Any last announcements or things that people.

[Simon Squid]

We're launching a new drinks brand called Dream Brew. And we're using 10% of the profits to fund people's dreams and we're putting people's dreams on the cans so you can buy it basically everywhere online. And it's better than Starbucks. Starbucks is shit.

[James]

Let's make it happen, guys. Lastly, we're gonna put the link down in the description to join the school of mentors which is a private entrepreneur community that we built at the school of hard knocks where every single week we host live calls with 8, 9 and 10 figure entrepreneurs where you can get access to ask your questions directly to them to download the consciousness of their minds on how they think and how they built their multi million dollar and billion dollar companies. So we can't wait to see you on the inside. With that being said, we'll see you in the next episode.

[Jack]

And real quick, shout out to our community member Kezzo for coming out and being with us here on the podcast today. Watch behind the scenes. So he's part of the school mentors. Got to come and sit in on the chat with us here today. So thanks for being here with us, brother.

[James]

Let's go. We'll see you in the next episode.