Simon Squibb
Key Takeaways
- Simon Squibb was homeless at 15, but by the age of 40 he had made enough money to never work again.
- He enjoyed retirement for precisely six months, then realized: “I didn’t have a purpose.”
- By helping others become entrepreneurs Squibb is now a global influencer with more than 18 million followers.
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When Simon Squibb was kicked out of his family home aged 15, he quickly built up the first of many businesses that helped him transform his name into a global brand. A gardening venture born of teenage survival kick-started the journey that would lead to the creation of YouTube’s most-watched business video: “30 years of business knowledge in 2hr 26mins.” (15M views to date)
More than 18 million social media followers now watch Squibb hand cash to strangers in the street if he likes their business idea. He also bought a staircase in London with a doorbell for people to “pitch their dreams,” and now has a similar doorbell in New York, which he runs with Sir Richard Branson.
Here, Squibb reveals to Big Think how he became a “professional talker” and how other leaders can explain ideas more clearly; why he’s opposed to traditional school education; and why he wants to give all his money away rather than leave it to his son.
Big Think: You’ve built 19 businesses, and invested in more than 80. Do you think entrepreneurs are made — or born?
Simon Squibb: Anyone can start a business. Anyone can make money by doing what they love. My entrepreneurial muscle was activated by circumstance. My father died when I was 15: a sudden heart attack. One second he was there, the next he was gone. Then my mum and I argued — she said, “Get out of my house,” and I took her at her word. I never went back.
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I was homeless for eight weeks; on the streets, friends’ sofas, in a stairwell. Without a National Insurance [UK Government ID card], I couldn’t get a job. I realized my only option was to create my own. I saw a big house with a messy garden, and knocked on the door. I had no equipment and had never done gardening, but quoted them £200 a month [about $400 USD back then] to do it up, and they agreed. I knocked on more doors, found more customers, and convinced the original household to let me borrow their lawnmower and tools. It was a bit awkward, because I’d positioned myself as having a gardening company, but I think they just saw a young kid trying to do something and helped me out.
Big Think: You went from being homeless at 15 to selling marketing business Fluid for multi-millions. What did that journey look like?
Simon Squibb: With more gardening clients, I could rent a room in a house. With an address, I could get a National Insurance number and find a job in customer services, then in a shop. Looking back, I was just fighting to survive. But weirdly, I now think of it as a positive experience.
I dabbled with employment for a while. It was quite nice not to have to worry about bringing in a set amount of money, just getting a monthly payment from the boss. But I didn’t last long: my brain was too busy thinking about business ideas. Working for someone else made me weak. I wasn’t creating anything.
With social media, you’ve got to have something that makes people stop and watch. It’s a combination of a hook and helping people think differently as quickly as possible.
So I started one of my early businesses, Accommodation Express. It was a bit like Hotels.com, before the internet. I built a referral system so when people called a full hotel, my company would help them find another room. I went on to build 19 businesses, but when Fluid was bought by PWC, I turned 40 and retired. I thought it was a dream come true: never having to work again. For six months, it was great. But I was basically a money manager: it was boring. I didn’t have a purpose. I needed to use my brain, and felt quite desperate to find something new to do.
Big Think: Money motivates most of us. Without that requirement, what drove you?
Simon Squibb: Yeah, money was not my motivation, which was quite nice. I could think: What do I like to do? I remembered how painful it was at 15, trying to build a business without any help, or access to capital. I could see all these people selling courses that most couldn’t afford. So I thought, why don’t I just start sharing the knowledge that I’d got for free?
That’s what I started doing: going on YouTube and TikTok and sharing business knowledge for free. There are loads of people doing it now, but I was the only one back then who wasn’t selling a course.
Big Think: You’re known for taking a contrarian stance — “You don’t need money”; “Getting ahead of 99.9% of people is easy” etc. What fueled this sideways approach to teaching?
Simon Squibb: It’s a hook model. People think, “You can’t start a business with no money.” Yes, 100%, you can. Most of the best businesses have been started with no money. But with social media, you’ve got to have something that makes people stop and watch. It’s a combination of a hook and helping people think differently as quickly as possible.
A lot of people have beliefs that aren’t true. That’s the thing about the hook — you have to challenge them, fast. People think, for example, that it’s safer to work for someone else. But the real safety is in owning your own destiny. If you’re working for someone else, they might lay off 10,000 people, like Meta just has.
My dream right now is to fix the education system and to fund people’s dreams.
Because I left school and home at 15, I’ve never been on a normal path. If you ask someone if a 15-year-old should leave school to start a business, of course, they’ll say no. But because I’ve lived an unconventional life, I see that way is often the best. I now know things that you’re told at school aren’t always true.
Big Think: You homeschool your son — why do you think that the education system doesn’t help entrepreneurs?
Simon Squibb: At school, you’re ranked based on exams you have to do on your own. An A is success; a D is failure. But in the real world, I would never do an exam on my own. I’d get help; ten people to do the exam together, and we’d all get an A. I’ve never sat at a desk and built a company on my own: I work with teams. In the real world, teamwork is what leads to success. The ones who try alone often fail. But in school, the focus is all about teaching individual achievement.
Big Think: On social media, your success is rooted in your ability to make complicated things simple. Where did your gift for explaining come from?
Simon Squibb: I practiced. Like anything, you get better with repetition. I made videos every day for six years, which sharpened my content-making. Just because one video works, it doesn’t mean the next will. Two days ago, I posted a video interviewing someone on the street and asking, “What’s your dream?” and it got 30 million views. The next day, a video with the same opening only had 500,000 views. So, you iterate, experiment, and innovate.
When CEOs or founders need to explain things in an interesting way, sincerity always wins. Openness, honesty, and authenticity. CEOs can’t hide behind a corporate brand anymore: People want to know who’s behind the company, what are they’re going to do with my data, and are they ethical? What are they doing with the profit? I think “for profit, for good” companies are the future. People want to connect to the business purpose and the owner. And if you’re a CEO of a company and you don’t have a social media presence, you’re going to find it harder to get a job.
Big Think: Talking of finding it harder to get a job, graduates are leaving universities and struggling to find work as AI wipes out thousands of roles. What AI businesses most interest you now?
Simon Squibb: Every business has AI in it now. Years ago, people would ask if companies were online or had a website. Now, of course, everyone does. History is repeating itself. AI is becoming prevalent in every business. The mistake people are making is investing in “AI businesses” — it’s companies that have a purpose and that invoke AI that will boom. I’ve invested in Lovable [the Swedish vibe-coding startup]: you can voice clip the app you want it to build, and it will build it for you. Coding and the technical product-build side used to be a major barrier to building a business. It’s not anymore. Now you’re only limited by your imagination. That’s exciting.
A lot of people have beliefs that aren’t true. That’s the thing about the hook — you have to challenge them, fast.
But yes, a lot of the traditional jobs are going to be lost. Graduates are struggling to get jobs. But that means entrepreneurship is about to explode. If people can’t get a job — just like me at 15 — then they will have no choice but to create one.
Big Think: You have a positive mindset. You think education doesn’t work, so teach in your own way. You think AI will kill swathes of jobs, but bring in more entrepreneurial opportunities. Do you have an upbeat mantra by which you live your life?
Simon Squibb: The purpose of life is living with purpose. When I retired at 40, I realized money alone doesn’t provide meaning. Financial advisors flocked to me, talking about putting the money into trusts and avoiding tax. But I look at it like: where can the money go that’s useful?
I could give it to my son, but my job as a parent is to give him a fishing rod, not give him a fish. If I’m a good parent, he should be able to make his own money. If I just give him a load of money — and I‘ve seen people do that — the outcome is not positive. People lose their drive and lean into drugs, alcohol. It’s not healthy to give any one person — even my son — a load of money.
So my dream right now is to fix the education system and to fund people’s dreams. I think if I do that, the world will become a better place for my son to live in. That’s a better legacy than a lump of money for the sake of it. And it gives me a purpose every day too.
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