As a teenager, Simon Squibb lost everything. He was homeless, grieving and isolated. His world was in ruins following the sudden death of his dad.
“I was 15 when my dad died of a heart attack in front of me. Eight minutes after saying he didn’t feel well, he was gone,” Squibb recalled.
What followed was eight weeks of homelessness where he was left sleeping in phone boxes, stairwells and on park benches in London.
But it was in that dark period that the entrepreneurial “muscle” in his brain kicked in.
“I walked past a big house one day, the garden was messy, and my brain said: ‘maybe they’ll pay you to clean it.’ I’d never thought like that before,” he said.
“I didn’t want to knock on the door, I was terrified, but I did. And they said yes.”
That moment didn’t just earn him his first dollar. It planted a seed that would shape the rest of his life.
“I realized I didn’t need someone to give me a fish. I could build my own pond.”
Now a multi-millionaire entrepreneur with a string of flashy accolades to his name, Squibb spends his days encouraging others to do the same, to “build their own pond,” whatever that may look like.
He has built 19 companies in his lifetime, including creative agency Fluid, which he sold to PwC in a rumored six-figure deal.
He’s invested in more than 80 start-ups, authored a best-selling book called “What’s Your Dream?” and recently launched an app of the same name where users can get free advice from an AI version of him.
But ask him what drives him now, and it’s not money.
“I plan to give it all away before I die,” he said. “I don’t want to leave behind wealth. I want to leave behind people who believe in themselves.”
Later this year, he’s bringing that message to Australia as part of his “What’s Your Dream?” tour, which he hopes will ignite something in those feeling stuck.
“We’ve been sold a lie,” he argued. “The university, the job, the retirement plan … it’s all part of a packaged narrative that keeps you trapped.”
“People end up following a life path they didn’t even choose. They just went along with what they were told was ‘safe’ or ‘smart.’”
It’s a sobering statement given the current economic climate, where even highly skilled Aussies and educated university graduates are battling to get ahead financially.
“University teaches us to conform. They sell us a degree, a job, a life plan. But universities are a business. Of course they’ll market themselves as the path to happiness, that’s how they survive,” he said.
Which is exactly why, according to Squibb, young people should feel empowered to walk away from unfulfilling jobs.
“Quit your job? Maybe. But do it with purpose,” he said. “If they’re in jobs that don’t align with their values or dreams, absolutely.”
“But I’m not romanticizing it. It’s not easy. You’ll face rejection, failure. That’s the point. You grow through the challenge.”
He added that anyone “with a phone in their hand can build a new life.”
It might not happen overnight, and it might not look like what their parents envisioned, but it’s possible.
“We live in a time where opportunity is more accessible than ever. You can start a business on your phone. You can find an audience online. You can monetize your skills without needing permission,” he said.
He’s not suggesting everyone throws in the towel immediately, but he is calling for a mindset shift. A move away from doing what’s expected, and toward doing what feels meaningful.
“Being rich isn’t a dream, it’s the by-product of one,” he said.
“Your purpose is usually buried under pain you’ve lived through. People wait until they’re in crisis before they change direction. I want to get to them earlier, before the burnout and breakdown.”
For many in their twenties and thirties, his message is sobering.
Skyrocketing living costs, stagnant wages, and a spiraling housing market have forced younger generations to question what exactly they’re working towards.
“The purpose of life is not to retire with a pile of money. It’s to wake up excited about what you get to do that day,” he said.
“If you don’t have that, it’s time to start dreaming again.”
Squibb said clarity often came from action.
“Take a small step. Knock on a door. Try something that scares you. That’s where confidence comes from, not from reading books or watching TED Talks, but from doing,” he said.
And if there’s one message he hoped people would walk away with from his tour, it’s that, you don’t have to wait for permission to change your life.
“You don’t need to be the smartest, the richest, or the best connected,” he said. “You just need to be brave enough to begin.”
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