In this interview I speak to Simon Squibb, a remarkable entrepreneur whose journey embodies resilience and purpose. He was made homeless at fifteen years old after the untimely death of his father, and set up his first business when unable to get a job at such a young age. Three decades later, he is now a self-made multimillionaire, having launched over 19 companies and invested in more than 70 start-ups. From sleeping rough to selling his agency Fluid to PwC, Simon’s story is one of grit and reinvention. He is also a No.1 Sunday Times bestseller for his first book What’s Your Dream which has been in the Sunday Times bestseller list and shares lessons on how to identify what your dream business might be, how to get started, how to move away from limiting beliefs that might be holding you back, how to find your first customers and build on small successes. Today, as the founder of HelpBnk, he’s on a mission to empower 10 million people to start their own businesses, challenging the narrative that entrepreneurship is impossibly tough. In our conversation, Simon shares profound insights on purpose, risk, and redefining success—offering a fresh perspective rooted in his extraordinary life.
Q: What is the relationship of purpose to success?
[Simon Squibb]: Many people can make money building a business without a purpose—that much is clear. Plenty have done it before, and many probably will in the future. There will always be market gaps and opportunities to generate profit without any deeper purpose.
My point, however, is that if you want to truly enjoy building your business, have a purpose. If you want to feel genuinely motivated each day, have a clear purpose. If you want to savour the journey itself, bring purpose along for the ride so you can actually enjoy yourself along the way.
If you build a business solely to fill a market gap and earn some money, there’s a strong chance you’ll eventually give up. There’s an even higher chance you simply won’t enjoy the ride. That doesn’t mean you can’t succeed or build a business without purpose—there are plenty of companies out there doing exactly that.
But having a purpose is the ultimate hack for making the entrepreneurial process enjoyable. It lets you move beyond endless discussions about work-life balance and the overused narrative that entrepreneurship is “so hard.” The truth is, you’ve only made it difficult because it lacks personal meaning.
Q: What’s your mission now with society and entrepreneurship?
[Simon Squibb]: I’m simply trying to encourage people to get started. Often, the system is structured so that those who already own businesses prefer others to work for them. Their motivation isn’t to inspire entrepreneurship; rather, they want you as their employee. As a result, entrepreneurship is portrayed as extremely difficult and daunting.
Don’t get me wrong—doing anything worthwhile is tough. Hiking a mountain is tough. Everything has its challenging aspects. But consider the alternative: working for someone else, being told precisely what to do every day. Waking up each morning to follow someone else’s orders can be a miserable existence. Many entrepreneurs conveniently forget this reality and fall into believing their own exaggerated narrative about how incredibly difficult and special their journey is. They may not want their employees to realize that owning equity and building something scalable is actually quite smart.
I’d say to entrepreneurs who claim it’s impossibly tough: if it’s so awful, give your equity to your team and step aside—but they never do. Meanwhile, employees typically surround themselves with others who are also employees, creating a self-reinforcing bubble that insists entrepreneurship is unbearably challenging. But it’s not. Being an entrepreneur is no harder than working for someone else; it’s simply a different experience.
I completely agree that the whole narrative of entrepreneurship being excessively hard is exaggerated and fundamentally untrue.
Q: How should we be thinking about risk in entrepreneurship?
[Simon Squibb]: I discuss this in my book: risk is actually an asset. The fundamental basis of risk is fear—fear is what signals risk to us. Originally, fear was designed to help us respond to immediate danger, like encountering a lion. This fear creates a powerful, heightened state within us, enabling survival. Despite a lion being stronger and faster, our fear-driven response allows us to outthink it and survive.
In modern society, however, we mistakenly think that by saying ‘no’ to fear, we eliminate the feeling. But fear isn’t meant to be dismissed; it’s intended to be embraced. You’re meant to acknowledge fear and learn how to “beat the lion.” This is the superpower fear provides.
I actively seek out fear, engaging in activities that awaken this powerful state. I believe people should lean into fear, using it as a superpower rather than avoiding it. Fear sharpens your focus, enhances your performance, and boosts your resilience. This is something many haven’t realised—fear is a superpower meant to be embraced, not avoided.
Q: Do we need to rethink the metrics of success?
[Simon Squibb]: I completely agree with you, 100%. Success should simply mean enjoying what you do and feeling purposeful. When someone tells me they genuinely enjoy their daily life, I never think to ask how much money they have—I already see them as successful. If you have all the money in the world but spend every day miserably staring at a computer screen, feeling bored, uninspired, not learning or contributing meaningfully, then no amount of money makes you successful. In my view, that’s actually failure.
People definitely need to rethink their definition of success. For me, success is helping 10 million people start their own businesses. For someone else, it might mean being able to garden every single day because that brings them joy. If that’s your passion and you’re able to do it, then that’s success.
I think we’ve become too caught up in society’s hype around success. Honestly, ask yourself—do you really want to live Elon Musk’s life? He deals with tremendous stress, multiple marriages, and immense responsibilities. While having vast wealth and power might define success for him, for most people, it would be a nightmare. Each person needs to clearly define what success truly means to them. If that high-stress lifestyle appeals to you, that’s fine—embrace it. Personally, that isn’t my idea of success. Success should always be redefined according to your own personal values and happiness.
Q: What does wealth mean to you?
[Simon Squibb]: The journey itself is truly the enjoyable part. Reaching the destination is always somewhat disappointing because expectations rarely match reality. I completely agree with you on this. However, discussing this can be delicate, as some of your audience likely have money, while others might not.
The notion that money doesn’t buy happiness is nuanced. Money certainly helps when you’re already happy and fulfilled. I’ve built businesses, enjoyed the process immensely, and made millions, reinvesting that money into the projects I loved. But if you’re already unhappy, making millions will only amplify your misery. People need to rethink what amount of money genuinely leads to happiness, returning to our conversation about defining success.
Yet, discussing possessions is difficult when addressing people who might not have much. It’s crucial to understand that if you’re not careful, possessions can end up owning you. When I bought a brand-new Porsche from Mayfair, it felt incredible at first. But soon after, it got scratched, needed constant maintenance, and it began controlling my life. Eventually, the car became part of my identity; it represented who I was, which isn’t healthy.
Honestly, I want everyone to become wealthy and experience this firsthand because once they do, they’ll realize material possessions aren’t fulfilling. Yesterday, someone approached me wearing a £1,000 designer top, complaining they couldn’t afford to launch their clothing brand—ironic. Instead of pretending to be rich, they could sell that top, produce 30 new tops, and grow from there. Spending money just to appear wealthy doesn’t fool anyone. When I see someone flaunting expensive clothes, I immediately think they’re broke, not rich.
Honestly, I wish I could give everyone £1 million just so they could realize that buying things doesn’t actually bring lasting happiness. Then they’d naturally refocus on what truly makes their work enjoyable each day. Unfortunately, society is so deeply structured around materialistic ownership that it becomes incredibly challenging to convey this understanding to those who haven’t experienced it directly like you and I have.
Q: How do you approach your philanthropy, and giving back?
[Simon Squibb]: I consciously avoid using the word ‘philanthropy’ because it suggests charity, which isn’t quite what I’m describing. Initially, my motivations were selfish. After retiring at 40, I spent two years without direction and became restless. With all my knowledge and energy and nowhere meaningful to channel it, I felt lost. So I asked myself: what do I genuinely enjoy, and how can I contribute positively to the world?
Reflecting on my younger self—15 years old, let down by the education system that never taught me about money or real-world skills—I realised I wanted to fill that gap. Schools still don’t teach essential skills like selling, even though everyone is capable of learning this. This gap frustrated me deeply. Researching the history of education revealed that industrialists like Henry Ford and Carnegie deliberately structured schools to create obedient factory workers, which angered me even more.
Initially, my actions were driven by selfishness—I enjoyed meeting interesting people, gaining knowledge, and sharing insights that schools failed to offer. It was my own need for purpose that led me to interview fascinating individuals and share their wisdom.
Over time, my approach evolved. Initially, I’d decide what content people needed, such as videos on raising money. But after interacting directly with the community, I realized they actually needed practical advice on selling their products, not fundraising. Most importantly, I discovered people primarily need someone to believe in them, along with basic marketing skills and some initial funding.
Recently, we shared a video featuring Daisy, who works on minimum wage but dreams of launching her own business. The impact was immediate—orders began coming in, illustrating the power of business to create positive change. It’s crucial to me that this initiative remains a business rather than a charity because I believe in fairly compensating my team and attracting great talent.
Building this platform taught me something valuable: society operates predominantly on a transactional, give-and-take model. But the reality is, humans naturally thrive when we give without expecting something in return. Historically, communities provided support freely, without tracking every transaction. If someone needed help, it was given without hesitation.
Yet, today we’ve lost this natural inclination. Society and media foster fear and mistrust, convincing us it’s dangerous or foolish to help freely. We’re trapped in a cycle of fear and transactional expectations—loaning money with resentment if it isn’t repaid, or performing kindness expecting reciprocation.
We must return to our natural state of giving without expectations. If everyone committed just four minutes a day to help someone unconditionally, we’d see this generosity reciprocated naturally. Helping without expecting returns is liberating—it reconnects us with true happiness, purpose, and community.
Q: People need to ask for help more!
[Simon Squibb]: People often assume others aren’t willing to help, but that’s simply not true—people genuinely want to help. In fact, there’s more kindness around us than we usually recognise. It’s crucial to remember this.
The real problem arises when people are too embarrassed or hesitant to ask for help. I’ve known individuals who nearly took their own lives because they were too ashamed to reach out. Yet I’m certain we’d all prefer they asked for help so we could support them and make their lives better.
Asking for help shouldn’t be seen as weakness—it’s strength. If you find it difficult, just remind yourself that most people would gladly step in and help if they knew you needed it. Keeping that perspective can be lifesaving. We’d always prefer someone to seek help rather than struggle alone. Life becomes better when we openly support one another.
Q: How do we stay resilient, when entrepreneurship is so hard?
[Simon Squibb]: Ironically, we’ve come full circle because I don’t believe entrepreneurship is inherently difficult. It has challenging moments, sure, but it’s similar to raising children—there’s always love, and there are inevitably difficult moments, too. Just like parenting, the hard moments amplify the joy. I believe the more pain you experience, the more joy you ultimately find. It’s like working out at the gym; the greater your muscle soreness, the bigger your gains.
Pain itself creates purpose. People often say, “no pain, no gain,” and it’s true in business and life. Pain leads to meaningful achievements. Right now, I could be relaxing—enjoying my hot tub or playing golf—but instead, I choose to help others because I know someone will suffer if I don’t share my knowledge today. This urgency drives me to act.
If more people adopted this mindset—that someone else might suffer without their help—they’d push through the pain, doubt, and fear. Leveraging fear rather than avoiding it allows you to do something meaningful with your life before it’s too late.