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StartUp 2022: Simon Squibb on homelessness at 15, retirement at 40 and his post-Covid enlightenment

StartUp 2022: Simon Squibb on homelessness at 15, retirement at 40 and his post-Covid enlightenment
Ryan Elliott
Ryan Elliott
Content Manager
Enterprise Nation

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 10m people start and grow businesses of their own.

Ahead of his speaking appearance at StartUp 2022 on Friday 21 January, Simon joins Enterprise Nation’s Ryan Elliott to chat through his background, most recent business venture and what he hopes to achieve during the upcoming event.

Be sure to secure your StartUp 2022 tickets today to hear from Simon and a whole host of other expert speakers.

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.

“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 self-taught myself those things, 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's a lot of people that 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 9m 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.”

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 personally did for me was it woke me up, actually. 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 that were affected by Covid, and so, when I started The Purposeful Project, I realised there were a lot of people Covid also woke 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’, I saw it coming, because I was talking to these people that were like: “you know, well-paid jobs and on paper, good roles, but this isn't me, I don't want to work in this company, I've woken up.”

“So, a large proportion of the people we were helping on our platform ended up being in their 40s – part of the ‘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 reassess 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'm 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 so, the biggest challenge for me initially was like, I wanted to help those that didn't have a company at all. If you've got a company that's doing well, there's 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 caused both excitement in me and my team, but also it meant the funding of it was quite a challenge at the beginning.

“I think initially I got quite lucky - I think luck is a key part of being successful. Luck is a skill as well, but that’s a different subject! The point I'm trying to make is that I’ve got plans like TikTok teaming up with us and they fell in love with our mission, so we had a combination of initially having to really worry about how can we make this scalable and sustainable if we're not going to charge people for help, which is our mission, and then equally, we then 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 case studies 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, and one of those people could go away and create a business that then ends up curing cancer - you just don't know!

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

“And so, it's one-on-one help, it's not the thousand people in a room but it still feels good, and I think this company TableYeti are 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, that one person can go on to 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.”

Let’s move on to StartUp 2022. You’re very much one of the most anticipated speakers at the event in January – what do you hope to achieve there?

“Ultimately, I'm excited about this whole programme because I love the idea that you can inspire and empower people, and personally, I believe that anyone can be an entrepreneur. Sometimes it's just a question of what type of entrepreneur you are, and maybe deleting the programming that you've been given about what an entrepreneur is or what constitutes an entrepreneur.

“Maybe you've seen Elon Musk so you assume you have to be like him, or you've seen Steve Jobs and you think you have to be like him and then you think maybe these are outliers, and they are.

“I love the idea of helping millions of people start a business, that anyone can if they want - it’s not some mystical thing that only a magical few can do. It is a process just like any other discipline, and you have to know your skills, and then hire or bring in people with the skills that you don't have.

I've seen businesses started by accountants - you wouldn't see accountants as traditional entrepreneurs, but actually they are, and then they often have to bring in marketing people because that's not their skill, and equally, I myself am a marketing person but I definitely need a good accountant any time I start a business. I know my weaknesses, and so I just love the idea that you can give people hope, and you can give people what they need to go and help themselves and not wait for a job, but create one for themselves.”

StartUp 2022 kicks-off on Friday 21 January. Grab your tickets to hear a swathe of expert speakers, including Simon, right now.

startup 2022 tickets

Ryan Elliott
Ryan Elliott
Content Manager
Enterprise Nation
I'm Enterprise Nation's content manager! If you're an adviser who would like to write a blog post and feature on our website, please get in touch.

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