Simon Squibb on homelessness at 15, retirement at 40 and his post-Covid enlightenment

Simon Squibb on homelessness at 15, retirement at 40 and his post-Covid enlightenment

Posted: Thu 28th Oct 2021

Simon Squibb isn't your bog-standard entrepreneur. Going from sleeping on the streets to founding 19 of his own companies, Simon possesses the passionate view that anyone can be a successful entrepreneur, given the right tools.

As a result, he's set himself the ambitious target of helping 10 million people start and grow businesses of their own.

Here, Simon Squibb joins Enterprise Nation's Ryan Elliott to chat through his background, most recent business venture and what he hopes to achieve in the near future.

Let's start by rewinding 20 years. Give me a quick whistle-stop tour of how you got to where you are today.

I was kicked out of home at 15 years old. My father had just died, and my mother and I fell out and, yeah, she kicked me out of home, so I've gone from living in a secure, happy family environment to suddenly being on the street.

And at that time I didn't have access to a National Insurance card which is what you needed to get a job, so I had no choice but to start a company, and from that moment where I was forced to be an entrepreneur till today, I still fall in love with the magic of: you have an idea in your head, and you can make it real.

What then became clear in my career over the last 20 years is just how big your imagination is. What you can conjure up in your brain, and then turn into reality. The first thing I ever did was a gardening company – not that imaginative but it did alright. And then from that moment until now I've started 19 companies and invested in 73 start-ups.

Pivotal moment

And I guess quite a pivotal moment for me was moving to Hong Kong and starting a business, because I realised how big the world was. It wasn't just my imagination but realising what else was out there and when living on the doorstep to China when Hong Kong was just getting handed back to the Chinese really opened my mind and world again.

So those are pivotal moments that kind of forced me into entrepreneurship; learning it, loving it, and then going into a different market completely while working in, operating in China, and then I spent most of my career building businesses that are useful to people that want to start and grow a business.

Based on my own experience at 15 I found it really hard to start a company. I was quite lonely, I didn't know how to find a co-founder, I didn't know how to raise money. I didn't know how to hire or fire people, I didn't know any of those things.

So I taught myself, and I found that when I got to a point in life where I could give back and help others learn the skills that I'd picked up over the last 20 years, I would do it and now is that time.

You founded The Purposeful Project last October. Tell me a little bit more about why you started it and what sort of service it provides.

It really kicked off when COVID began, and I was reading an article about how hundreds of thousands of people were not going to be able to find a job or be fired. Due to COVID, a lot of university students, for example, that perhaps were previously expecting a job when they graduated, their sentiment changed.

Two things: firstly, a lot of those people didn't necessarily want a job anymore, they wanted to be freelance or social media influencers or whatever it is - the world’s changed and they didn't necessarily want to get a job.

And equally, due to COVID, there was a lack of opportunity at high-level jobs. There have been a lot of changes – no-one's going into the office and those sorts of things. So, I read an article and thought: wow, there are a lot of people who haven't been given the skills to start a business, hundreds of thousands of people that haven't been educated in school about how to start a business who could start a business.


I then turned the page to another article which was about how technology over the next 10 years is going to make nine million people definitely unemployed, from cars that drive themselves to jobs linked with driving the economy. And I thought to myself: wow, there are millions more people who don't have the tools right now to start a business but who should be given those tools.

So, I then thought to myself: what can I do to help those people? And that's how The Purposeful Project got born. I started building out scalable solutions to common questions in entrepreneurship, and we set ourselves a mission to help 10m people start and grow a business.

That's how it started; it was a COVID-born business trying to solve not just a COVID-born problem, but I think a long-term problem brought about by the very thing that's supposed to help us: technology.


In this webinar, Simon shares his motivational tips for getting started with launching a new business.


Sounds like COVID was a big turning point for a lot of people to say: "Right, that's it, I'm going solo." Was that part of your thinking?

I had actually sold my last company, a company called Fluid, to PwC, and I was enjoying life, pretty much! Retired at 40, playing golf, enjoying myself. And I think what COVID did for me personally was to wake me up.

I thought to myself: I'm not a doctor, so I can't go on the frontline and help in that way, but I can help people who were affected by COVID. And so, when I started The Purposeful Project, I realised there were a lot of people COVID had also woken up.

I was expecting initially for us to be helping a lot of students, for example, and I was really shocked to see I ended up talking to a lot of people in their 30s or even 40s, who were in jobs they didn't like – a 'great resignation'.

It woke me up in a way, COVID. It woke me up from my casual, easy life, and brought me back to the fold to give back and equally, I think it did the same to a lot of people – they reassessed their lives.

What were the biggest obstacles you faced when starting your own businesses?

Well, interestingly enough, with my previous enterprises (I had a company called Fluid, as I mentioned, and I've had a company called Nest), all of those businesses used to help entrepreneurs. But I guess I'm going back to that 15-year-old me and helping – every business I've created is trying to do that.

I always had a very strong commercial sense. So, with the agency business we charge a fee, and in the mid-investment model we charge equity. And the biggest challenge for me initially was that I wanted to help those who didn't have a company at all. If you have a company that's doing well, there are plenty of accelerators that you can get into to get help.

But it's the ones who don't have money for consultants, or equity to give you. Who's helping those people? So, I made a line in the sand that we, as a platform, would never charge for help. And that excited me and my team, but also it meant funding the business was quite a challenge at the beginning.

I think initially I got quite lucky – luck is a key part of being successful. It's a skill as well, but that's a different subject! We really worried about how we can make this scalable and sustainable if we're not going to charge people for help, which is our mission.

And then equally, we got lucky, where people I think resonated with what we're trying to do and swung behind us and supported us.

Do you have any particular examples of entrepreneurs or businesses you've helped that you're most proud of?

I think there are different levels of help I'm proud of within the platform. When we do weekly webinars, hundreds, sometimes thousands, of people join, and these days with digital you almost forget how big these numbers are if you have a room full of people.

We have 1,000 people in a room and you're giving them advice and they go away and have a better life. And the butterfly effect of that is tremendous – one of those people could go away and create a business that then ends up curing cancer. You just don't know!

But just today, for example, I met a founder of a company called TableYeti. And I introduced him to a new client, who he's now picked up – they signed this morning. And I helped him frame his hiring process, because he was looking to recruit a marketing person. But it turns out he actually needs a B2B salesperson.

And so, it's one-on-one help. It isn't the thousand people in a room but it still feels good. And I think this company TableYeti is going to do really well. I'm proud of the big scalable things that we do, but I'm equally proud of the individual, one-on-one stuff that helps only one person.

You could argue that one person could go on to hire a lot of people, or create a lot of opportunity. And in this particular business case, they built a POS system that ensures people get tips.

In my mind, if I was a waiter out there getting a good tip, that might give them enough money for a side hustle to start a business.


Get more expert insight from Simon Squibb

In this webinar from Enterprise Nation's StartUp Show 2023, Simon reveals how to generate a million-plus TikTok following and become a mission-led entrepreneur.

Enterprise Nation has helped thousands of people start and grow their businesses. Led by founder, Emma Jones CBE, Enterprise Nation connects you to the resources and expertise to help you succeed.

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