Homelessness can happen faster than most people realise.
I was sitting in the front row of an entrepreneurs conference in Bucharest when Simon Squibb began talking about the night his dad died. I live far from my family. I only get to see them occasionally, and that distance sits with me every day. Hearing that someone lost their father at fifteen – I felt it somewhere deep. I was grateful and heartbroken at the same time, for a man I’d never met.
Simon’s dad died suddenly when he was just fifteen. In the grief and chaos that followed, after one too many arguments, his mum told him to leave. As Simon tells it, they were both stubborn – so he left, and he never went back. He became homeless. He dropped out of school. He slept rough in a London stairwell. And because he was only fifteen, without a National Insurance number, nobody would legally hire him. At an age when most of us were worrying about exams, he was hitting rock bottom with no floor underneath him.
Simon is a perfect example of human potential.
He talks about the moment his entrepreneurial instinct woke up – spotting an overgrown garden and thinking: I can solve this problem. That single thought led to his first business. Then another. And now, decades later, he has built over 80 companies, donated close to half a million pounds to aspiring entrepreneurs through his famous stairwell pitch sessions, and inspired millions of people to believe their dreams are worth chasing. He is one of the most generous entrepreneurs I’ve ever come across.
What moves me most about Simon isn’t just what he built for himself – it’s what he built for others. Help Bank exists because he believes that access to opportunity shouldn’t be a matter of luck. He encourages his whole community to help one another, not just to look to him. I remember watching one of his Instagram Lives where he admitted he felt like he wasn’t good enough – because he couldn’t help everyone who was reaching out to him. Here is a man who has achieved so much, and that’s what keeps him up at night. That kind of person is rare.
Simon is not alone in having lived through homelessness before finding his way. There are many well-known figures like Jim Carrey, Ed Sheeran, Pete Mullan – whose stories follow a similar arc. But their success, as uplifting as it is, always leaves me with a quieter question underneath it.
What made them the ones who found a way through? And how much human potential is out there right now, living in survival mode on the streets, not because it lacks talent or heart or dreams, but because nobody showed up at the right moment?
It’s a question I’ve sat with since getting involved with The Ootsider. And the closer you get to the reality of homelessness, the more urgent it becomes.
Every time we visit organisations like the Simon Community in Edinburgh and walk into their support hub – it is always full, always intense. It is very easy to be disconnected from homelessness when you don’t see it up close. When you do, you realise the scale of it is worse than most people imagine. And beneath it, almost always, are mental health challenges that went unaddressed for too long. The distance between struggling and homeless is shorter than most of us want to admit.
I believe everyone deserves endless chances to start again. To rebuild. To pivot. Not once – but as many times as it takes.
That belief is the whole heart of The Ootsider.
When we lose hope and feel invisible, a small act of kindness can bring light back into our lives. That’s what we’re trying to do – by providing warmth, keeping people dry, showing someone that they are not forgotten. Something as simple as a Changing Robe can be the spark that gives a person the courage to seek further help. And that help can lead to the next step. And the step after that.
One step at a time is how anyone climbs out of anything.
When I think about Simon asking strangers “What’s your dream?” – I think about the people who have forgotten they’re even allowed to have one. Dreams make us human. They move us to act, to build, to reach for something better. No dream is too small to matter.
Simon Squibb built an empire from a messy garden and a single moment of belief in himself.
Imagine what becomes possible when we give someone their first reason to believe again.
