From Homeless Teen To Millionaire Founder: Simon Squibb Reveals How To Change Your Life Fast

0:00Today, we are joined by Simon Squibb. From a homeless teen to a multi-millionaire entrepreneur, best-selling author, and mentor to millions, Simon has truly lived every single part of the entrepreneurial journey. After selling his agency Fluid to PwC, he launched HelpBank and the hashtag GiveWithoutTakeMovement to help over 10 million people start businesses. Now one of the most followed voices in entrepreneurship, he's known for his viral street interview series and has over 17 million followers. Simon, welcome to The Burnouts. Hi, I am Simon Squibb and this is The Burnouts. Simon, welcome to The Burnouts.

0:36We're so happy to have you here. I'm so happy to be here. Thank you for having me, guys. Okay, I want to walk back for our audience who might not know you to, you know, growing up, 15 years old. What was that experience like and how do you think that formed you as such an incredible, you know, business icon and entrepreneur today? So my father passed away when I was 15 years old. He suddenly died of a heart attack. A very shocking moment. He died in front of me, which still blows my mind when I think about that, that moment in my life. I thought he was joking, you know, like he was having a heart attack.

1:05I thought he was joking. And so eight minutes later, he's dead. So he's gone forever out of my life. Crazy. And then my mum and I, we were having friction anyway. And then the pain of my father dying. After a couple of days of misery, of course, we just argued all the time. I was 15. I want to be out trying to like deal with it with my friends. And my mum wanted me home. And we just argued. And then, and at one point she snapped. I was like, get out of my house. And I left and never went back. I was homeless for eight weeks, but there's different types of homelessness, right? There's like institutionally homeless.

1:38You're, you know, you're on drugs or whatever. You've got a problem. You're in the street. You are homeless. That's one type. There's of course people that get kicked out of their house. Like they haven't paid their rent or their mortgage. House and they're kicked out. They've got debt. They get kicked out and they're forced into the street because they can't afford accommodation. And then there was this structure that I had, which is literally like an argument with my mum. And then I was stubborn. She was stubborn. I just, I left because she told me to, and then I couldn't go back. As I got older, I realised that, you know, she's a narcissist, but she's still alive today.

2:10She sees herself as a great mum. And she was for the first 15 years of my life. And then that moment, we just broke. Our relationship broke forever. I then experienced homelessness and a combination of like sleeping in the street and living at friends' houses for a while, sleeping on couches. I learned actually, like, for example, I slept in the street. I didn't have a blanket or anything. This homeless person gave me her blanket. You know, like someone who's got nothing will help me. You see what I mean? And I think for years as a kid, you walk past homeless people, you don't really register it.

2:44And parents try to protect you from it, right? It's like, don't worry, come here, it's fine. You know, it's human lying in the street. And then I found out what these people are really like and how kind, frankly, a lot of them are. And how drugs sometimes, I used to think homeless person was a drug addict and went into the street because they were a drug addict. It turns out sometimes they're in the street and it's so miserable, so hard. They take drugs to numb the pain. I learned a lot of the truth about how homelessness works. Now I was only homeless for eight weeks and I did eventually start a business, which allowed me to pay rent for a small crappy room.

3:15That experience changed me forever, as you'd expect. And that was the start of my life. First, I'm so sorry that happened. And that's incredible. To be honest, I'm now grateful for it. I know that sounds crazy, but bad luck can turn into good luck over time. That experience showed me the real world. Just the way that you talk about people, it's so clear. You always assume the best of people. And I think that's really beautiful. And your early experiences, obviously, being a young person really shape you. And that's why I'm curious, when did it change from you being angry and upset and having this falling out with your mom to actually starting your own entrepreneurial endeavors to start to pay your own rent?

3:53How did that happen along the way? By the way, angry didn't really happen to me until like 20 years later. Wow. So at 15, I just hit a fight or flight. I just hit survival mode. I didn't feel pain. It's a miserable story, but I actually had like an experience that sounds weird to people, but it It wasn't until 20 years later, like when I eventually had money and I was comfortable and I'm like, why am I like this? Why am I so driven? Like too driven. And then I went, got psychiatric help, which I think everyone should do, by the way, because it allowed me to understand how my brain had got rewired in that time.

4:27Because I had to shut off emotions at 15. And I just had to like figure out a way to survive. I started a business because I couldn't get a job. I was too young. No one would give me a job. Social services, the benefit system in England, told me to go away because I was a man, a 15-year-old man. They didn't have accommodation for women with babies. They were like, you are like number 85 in the queue in this area. So you're very unlikely to get accommodation. But of course, as a 15-year-old, okay, I can't get that. As a child. Yeah, I didn't think I was a child. But I look back now, I've got a kid who's eight.

4:58I can't even imagine. He's nearly 15 in my head. I think it taught me the bad luck in your life turns into good luck. Sometimes your good luck in life can turn into bad luck. Like when I saw my company, the opposite, wow, I'm so lucky. I've made all this money. I built a business. I think for a week I was like, I was in, oh my God, this is it. I'm financially free forever. And then slowly I'm like, but what do I do? Where am I? I don't need money now. Why do I go to work? What's the point? You know, and suddenly all that excitement I've had in my life of building things and doing things was taken away from me.

5:32And that was a negative. I kind of look at my homelessness stage and that stage where I was in that difficult situation as the thing that's made me who I am today. And I don't want to change. I love it. I love what my life is. But making lots of money kind of destroyed me for a while. It took all the wind out of my sails. And my purpose was gone. My mission was gone. And I want to also better understand, you obviously took a really unfortunate situation and turned it into something incredible. You built all these businesses. But what was the first step? Were you mowing lawns? How did you make your first paycheck?

6:04So I think the thing I would say as a kind of quick headline is everyone should learn sales. And so at school, it's almost like a dirty word, like car salesman, right? Everyone sees sales as a negative thing. It's something every human can learn, introvert or extrovert. There's just different approaches, different tools, different ways to do it. But sales is like, you want to convince someone to fall in love with you. You want someone to join your company. You want to join someone's company. You need to learn to sell. I think the number one thing that I did was I knocked on someone's door and said, you've got a messy garden.

6:37I can tidy it up for you. And they said, yes, that's it. I didn't have any tools. I didn't have any gardening experience. I didn't have a website. I just tried my luck. Now I was scared and I was nervous, but I didn't just want to be successful. I needed to be successful. And that was the key. You'll push through fear if you need it. And needing it is just a mindset thing, right? If you need it, you will push yourself through pain. But if you can tell yourself you don't really need it, you'll default to human laziness, which is like, by the way, I see a lot of people in America trapped in this way.

7:10They kind of got an easy life. They're paying all the bills. They're off at the weekends. They're drifting. They're not fulfilling their potential because they don't need it. They're not fulfilling their potential because they don't need it. They just want it. Everybody wants it. It's those that need it that succeed. And I needed it because social services wouldn't give me anything and I couldn't get a job. So I didn't want to be an entrepreneur. I wanted a job. That's what school had taught me to do, ask for a job. But this thing woke up in my brain. I call it the entrepreneur muscle. It's a thing that makes you think about an idea and make it real and apply it.

7:41And they don't teach you it at school on purpose, in my opinion. Because if you understand how money works and you understand how to create something from your mind and make it real, you don't need to work for someone else. Bosses would have to beg you to work for them. They'd have to give equity. They'd have to give you upside in the business. They'd have to give you a percentage of the outcome, not ours. Most people are selling hours, right? Which is ridiculous. So this woke up in my brain and I realized, Hey, I don't need a job. I can create one for myself. I find that so interesting because still in the U S 2 % of VC funding goes towards women.

8:08And that to me is an absolute crime because we don't teach enough young women. Okay. You know, starting a business, having equity, you're not taxed the same. You're not getting, you know, 50, 50 % salary tax. If you're living in New York state or you're living in California, it's a completely different ballgame. And the worst thing that happens, Hey, you go start a company, you raise money, you fail. You can go get a job somewhere else because people are looking for people who've started companies before. And still we don't have enough, you know, women allocating capital to make those decisions to invest in other female businesses.

8:41We don't have enough women, you know, starting companies, even as you know, the number of women in CS and hard sciences, like chemistry and biology are going up. We still don't have enough women that are starting companies. And I think a huge chunk of that is due to education. First of all, when I hear that stat, it's a business opportunity for someone listening, right? If only 2 % goes to women, then does that mean that there should be more capital going to women or more women starting businesses? There's a business opportunity in both, right? So the way I look at it, honestly, as an investor, I've invested in 81 companies.

9:12As an investor, I'm looking for great people and great ideas. I'm genuinely not looking for only men or only women. What I see in the market now is funds starting with only women. I kind of think that's a mistake. You just want best in class. And you want to say, I promise you, if you are a woman with a good idea, we will invest. I agree. But the funny thing is now even as, so graduating classes now are like 50, 50 in terms of gender split of graduating with computer science or graduating with like chemistry degrees, et cetera, the gender split has gotten way, way better. And those are mostly, we see people, you know, the, the companies that truly raise, you know, giant amounts of venture capital funding are typically tech, you know, there's exceptions or like a science business, but we're still not seeing the uptick in women starting businesses the same way that we're seeing, okay, the uptick in those, you know, classes being equal gender split.

10:03And so I do think that there's an issue of, I think it is some bias. I don't think we're teaching enough young women this hack about the difference of what equity looks like over time versus what a salary looks like over time. I don't think that's being taught in general. The education system is broken. In general, men too, by the way, you know, I know men are working in companies and building brands and they don't own that company. They're giving up their life, their time, the most valuable thing they've got, and they don't own equity. It's insane. Now, even when I suggest that, like, oh, I don't think my boss will give that.

10:29Have you asked? Like, why wouldn't you have equity? Everybody who's made lots of money had equity in a business. Everybody who's successful owns equity in a company. Fact. I think everybody that works somewhere should either get equity where they work. And then if you can't get that, go start your own business and have equity. Now, starting your own business is hard at the beginning. I think it gets easier over time. Working for someone else is easy at the beginning. It's It's harder over time. But I know people at Facebook work there 10 years, recently got laid off. They don't own equity in the business.

10:55They don't even have shares. Like, it's insane to me. Why would you build a company up, make it worth trillions and not have a piece of your work? That's crazy to me. Insane. And they get fired. They're like, AI's replaced you. 10 years you built that company up. Thank you. You've given us so much money meta now. We can just employ AI to remove you. Thank you. Goodbye. Well, there's a lot of things that, to your point, really just aren't taught in school And what I would be really curious about is to understand, let's say a typical venture capital fund, I would be curious how many people pitching them are actually women.

11:28I think the biggest issue. Good to know. That would be great to know. Yeah. Is it that you have an equal amount of men and women who are pitching, but then the majority of capital is going to men? That's something to look into. I would be really curious to understand, is it just that over 90 % of the people who are creating the companies and pitching, are they men? then you can peel that back another layer and understand how can we get more women to feel confident and also to understand the resources available to them so that they feel empowered to start a business and then go and raise money for that business.

11:59That's definitely not taught in school at all. I mean, until we decided to go and start our company, it was the first time I had ever even understood what venture capital was, understood how to set up a business. And to your point. And I really want to talk about this for, for me, I would say the number one best skill I have ever learned in my life is sales, being able to pitch yourself, understanding how to sell yourself. Like that is just an invaluable thing. Everyone needs to know for whatever you do. And it's shocking to me that that, that is not taught in school because that's, that's how you get money.

12:33That's how you get a job is by being able to properly articulate your value. And I want to ask you, cause you're so good at this. What advice would you give to people? Just like sales fundamentals, one-on-one, what is the best way to present yourself? Be authentic.

12:59That is, you wouldn't normally think that in sales. It's like, you know, you've got to fake it. You've got to sell something that people don't need and make them buy it. No, the opposite. it. Identify your person that's going to buy it and then explain the product to them. That's it. You don't have to be faking it, lying, doing tricks. I see a lot of people teaching sales online and they'll be like, you know, create FOMO. Or if you don't buy it now, it's going to be gone. You know, no, you don't need to do that. So this is what's available. And you make a relationship with people. Sales is actually just another form of relationships.

13:3020 years ago, I sold to a guy, a partnership. And 20 years later, he's a billionaire now. And he invested in HelpBank. You know, like this relationship is 20 years old. And I didn't go to him, hey, would you want to buy my digital product? It's going to make your life so much better. I'm going to save your business. And then he signs and I don't do any of those things. And I get the money. Too many people are thinking of sales that way. No, I over delivered. And then he was like, my God, you said, were you going to do something? And then you did it. Let's do more stuff together, assignment. And then for the next 20 years, we were working together every chance we got, you know, like it's relationship, but there's three steps to sales that everyone needs to know.

14:07I think this is it. You don't need to go on a course. Don't need to pay for a course. You don't need to go to university. You learn by doing right. And sales is very simple. The first principle is know the person you're selling to like the company and their mission and the purpose of that person's job role. Right. So if you're trying to sell them a pen, they don't need a pen. You're wasting your time. No salesperson in the world, no matter how good you are, is going to be able to force that person to buy a pen unless you trick them. And that's not a relationship build. The second part is, do they need what you're selling?

14:36I've done a deal with every Fortune 500 company at least once in my career. And what I discovered is if you like the person you're selling to and they like you and you trust each other and you understand, second, they need you and you need them. Then the third one, finances, has always worked out. I've never had a problem figuring out the economics because we need each other and we like each other. I did a deal with the Wall Street Journal. I remember it so clearly, because I spent maybe four months getting to know the person at the Wall Street Journal. And they said, Simon, we've got this tender to build a new digital product for the Wall Street Journal.

15:05So I submitted my tender for it. Right. And he came back and he said to me, Simon, double it. He said, you're undercharging for this. You know, you deserve to earn more from it. I want you to be well paid because I want a good supplier. You know, I want you to make money so that you are a good, solid company to service this need. Whereas most people's experience is, well, Can you get the price down? Can you make it a bit cheaper? Because they didn't do the groundwork and build in the relationships with people. And then they didn't over deliver. And that's what sales is. Sales is, you know, initially an intro, build a relationship, provide what you promised, deliver what you said.

15:40And then over time, it's actually about relationships, right? That's the key that people forget. And that's it, sales, whole thing you need to know. Don't pay for a course because now it's go out there and apply that knowledge, right? And you'll be brilliant at sales. And if you're an introvert, use email marketing, for example, right? There's use social media. If you're, if you're an extra foot, go knock on doors, you know? Well, have you heard the saying? It's like, ask for money and you'll get advice. Ask for advice and you'll get money. 100%. Again, why is that saying so prevalent? If you're looking to raise money, that is such a relevant saying.

16:12I'll tell you why. If you ask someone for money, of course, their instant reaction is to just wait. And then they want to find out more about you, right? They want to know, will my money be wasted? There's a relationship dynamic that they have the power now and they're going to wait and find out about you. But if you ask someone a question, not for money, you're doing due diligence on them. This is why, by the way, I hate Shark Tank and I hate Dragon's Den, right? Because as much as I like them and shows, at least there's some business education going out in the world, it's made people, everybody think that you've got to go beg someone for money to start a business because you don't need money to start a business.

16:44You do not need any money. But those programs have taught you, hi shark, here's my business. Do you mind the face. Money has no value, right? Unless it's applied in the world. And I want to talk about when you moved to Hong Kong at 22, what did you learn? Now, when I went to Hong Kong, it was when Hong Kong was about to be handed back to the Chinese by the British, which is a really fascinating piece of history. But it's a really profitable place, huge wealth, and Britain peacefully handed it back to China, right? So as I'm going there, everybody in England, I'm saying, I'm going to go try out Hong Kong, they're like, oh, it's going to turn communism.

17:22It's about to become a communist country. I'm like, okay, what does that mean? Oh, you know, I just don't want wealthy people. They don't, they don't want you to be independently wealthy. I'm like, okay, all right. But all this preconception and I went there and I sat on the skyline of Hong Kong and watched this city skyline and I realised this city, Hong Kong in particular, there's no natural resources in Hong Kong. It's all based on brain power. If you have an idea in your head, you can make it real. woke me up to also what hard work looks like. I was there a week and I met a billionaire. And he said, oh, come on my dad's yacht on Sunday.

17:58I'm like, okay, it's a Sunday. You sure your dad wants me there? It's like, we just met. It's like, yeah, come on, be fun. So I went on this yacht and I was like, why is a billionaire on a Sunday, like not just with his family, it's kind of the England mindset, right? With his family. And he said, I realised there's no work-life balance. He doesn't need work-life balance. He loves his work. You see? So it's work-life integration. And that was a revelation to me. Because I'd always been taught, like, again, the school system, Monday to Friday, I go to school, Saturday, Sunday, I can have some fun.

18:27And I was so trained by the school system to think that way, Hong Kong woke me up to a different way of thinking. And I was like, actually, yeah, why am I separating my work and life? Now I integrate it. My wife was my business partner. My son's involved in my content. The people I work with are my friends. And fuck it, I don't care if it's un-PC. I don't care. They're my friends. I care about the people I work with. I haven't tried to separate the two things. I want to better understand, I love this concept of work-life integration. And it's something a lot of people who've come on the podcast have said to us.

18:55And I really think it disputes this notion of the traditional nine to five that people are really accustomed to believing is how you should live your life. Really, you can live a life where work is a huge part of your life and you really enjoy it and it folds into your life. How do you think people can build a career where they're able to live in that way, where they actually feel fulfilled and excited to go to work? I just think people need to realise, don't see this as a privileged thing. Don't make yourself a victim. Make yourself realise that if you apply yourself to something you love, work can be fun, and it should be.

19:27Now, maybe you have to do that job that's crap for now, work on the thing you're good at, get so good at it that eventually it makes money and you can flip it. And you can get rid of the crap job and make money from something you enjoy doing. 85 % of people in America don't enjoy their work. And I would argue that 85 % are therefore caught in fight or flight, which basically means you don't have your creative brain switched on. You're so focused on survival, your creative brain isn't coming on and you're running so fast that brain doesn't let you stop and have a dream. Right? So people need to come out of fight or flight and they can do it by just imagining for one second, they've got all the money they need.

20:02It's the abundance thing, right? It's like, just imagine you've got it all just, just to get yourself out of fight or flight for five minutes and then try to tomorrow to get yourself out of flight for 10 minutes. And slowly your imagination will kick in and you'll start to realize what your skills are and how you can apply them. And then you can enjoy your work. So I would warn people not to be victims because if you have a victim mentality, you instantly default to, well, it's all right for them. They've got money and you don't realize it's a mindset thing that ultimately leads to you having money.

20:28I was poor when I had this mindset. Now I'm rich with this mindset. So I want to touch on the topic though of happiness. You were broke when you had this mindset. You've been rich and you've had this mindset. How do you think that your experiences through your career have also influenced your personal happiness? Do you think there's a correlation with money? Yeah. So money only brings you happiness if you're already happy. So I know a lot of people that made money and they're miserable. It's extended their misery. So, but money is important. We all know the stats around like, if you need a base, I think it's a hundred thousand us a year to cover all your bills because, and they haven't said business, that's why I know this is true.

21:11That can take you out of fight or flight because of basic human needs like accommodation and food are not easily available. If you're worrying about eating today, of course you're going to be miserable, but the happiness is a dangerous pursuit. I don't think people should pursue happiness because happiness is fleeting. And so there's a thing called submersion, right? I remember the first time I went on a plane, I was so happy. I was in economy. It was awesome. The plane's taking off. I'm seeing the sky. Oh my God, it's amazing. About two years later, I'm sitting on the plane like, oh, I've got to see an economy.