From Homeless Teen to Serial Entrepreneur | Simon Squibb - Founder & Investor

Here are the top 10 key takeaways from Simon Squibb's conversation with Scott D. Clary on entrepreneurship, success, and finding purpose in both business and life.

1. Entrepreneurship is born from necessity

Simon Squibb's journey into entrepreneurship began after becoming homeless at 15 following his father's sudden death. Unable to get a job due to his age and lack of address, he was forced to become self-sufficient. He describes this moment as when "the entrepreneur muscle woke up" in his brain, teaching him how to make money and survive.

This challenging experience demonstrated how adversity can spark innovation and self-reliance. Simon views this difficult period as transformative rather than purely negative, showing how "bad luck" can become a catalyst for developing crucial life skills and a resourceful mindset.

2. Give without expectation of return

Simon advocates for a "give without take" philosophy rather than the traditional transactional "give and take" mindset. He believes helping others without expecting anything in return eliminates resentment and creates more authentic relationships. This approach has proven successful in his business ventures, where providing free work early in his career led to valuable relationships and opportunities.

This philosophy extends beyond business to his broader worldview about how society should function. He suggests that if everyone helped just one person daily without expectation, we could transform lives and society. This perspective challenges the predominant transactional view that dominates much of modern life and business culture.

3. Education system needs fundamental reform

Simon strongly believes our current education system was designed to produce workers rather than creators or entrepreneurs. He points to historical figures like Henry Ford and Carnegie who wanted people educated enough to participate in the economy but compliant enough to work in factories. This system hasn't been significantly updated in a century despite massive economic changes.

He advocates teaching financial literacy, sales skills, and entrepreneurship in schools rather than focusing only on traditional subjects. Simon suggests asking children "what problem will you solve?" instead of "what will you do?" to foster a mindset of contribution rather than merely occupation. This shift would help students think beyond just getting a job to how they might create value in the world.

4. Success means time freedom, not just money

Simon redefines success away from financial accumulation toward having freedom over your time. Though he achieved financial success through his agency which he eventually sold to PricewaterhouseCoopers, he measures true success by autonomy and life satisfaction rather than wealth alone.

He contrasts entrepreneurship with traditional employment, noting that many professionals like lawyers find themselves working increasingly longer hours to maintain expanding lifestyles as they age. Meanwhile, entrepreneurs who build successful businesses can potentially work themselves "out of a job" by creating systems that generate income without requiring their constant presence.

5. Entrepreneurship is accessible to everyone

Simon firmly believes anyone can become an entrepreneur, regardless of background or personality type. He challenges the notion that entrepreneurship requires special talents or circumstances. Instead, he sees it as simply a framework to monetize what you love doing, applicable to artists, athletes, actors, or anyone with skills to offer.

The key difference between entrepreneurs and non-entrepreneurs isn't innate ability but understanding business structures. Simon argues that the education system deliberately withholds this knowledge, creating artificial barriers to entrepreneurship. His organization Help Bank aims to make entrepreneurship accessible to everyone by providing the missing knowledge and support.

6. Property ownership is often a poor investment

Simon takes a controversial stance on property ownership, arguing that homes people live in are liabilities, not assets, since they cost money monthly without generating income. He challenges the conventional wisdom that property is always a good investment, pointing out hidden costs like maintenance, mortgage interest that can triple the actual price paid, and restrictions on mobility.

He further argues that treating housing as a business creates social problems when essential workers like nurses and firefighters can't afford to live where they work. Simon sees real estate investment as an inefficient way to build wealth compared to creating or investing in businesses that generate real economic activity, create jobs, and develop valuable skills.

7. Hack your luck through deliberate actions

While Simon acknowledges some luck comes from circumstances of birth, he believes 98% of luck can be "hacked" through three key elements. First, take more risks, as each risk increases your chances of lucky outcomes. Second, embrace fear as an asset that helps you perform better rather than something to avoid. Third, know your destination clearly, as having direction makes you more likely to recognize and capitalize on opportunities.

This perspective empowers people to create their own luck rather than viewing it as something random or outside their control. It transforms luck from a passive force to something you can actively influence through your mindset and choices.

8. Tribalism versus individualism shapes society

Simon believes excessive individualism has created societal problems that could be addressed by returning to more communal values. His experiences living in different cultures, particularly moving to Hong Kong and experiencing China, helped him realize people across cultures share fundamental desires for family wellbeing and security despite political differences.

He observes that many forces in society artificially divide people - politics, sports teams, and other affiliations - when we would benefit more from collaboration. Simon's Help Bank platform aims to rebuild this sense of community by facilitating people helping each other without transactional expectations.

9. Pain and adversity can become superpowers

Simon views adversity as potentially beneficial when properly framed. His own experience of homelessness at 15, while traumatic, gave him resilience and skills he might not otherwise have developed. He suggests "good luck and bad luck are both luck" - either can transform into its opposite depending on how you respond.

This perspective doesn't minimize suffering but recognizes its potential transformative value. Simon points to lottery winners who often end up unhappy despite their "good luck" as evidence that circumstances alone don't determine outcomes. Instead, our response to circumstances shapes whether they ultimately benefit or harm us.

10. The purpose of life is a life with purpose

Simon's ultimate philosophy centers on finding meaningful purpose rather than pursuing wealth or status for their own sake. His work with Help Bank aims to help 10 million people start their own businesses, driven by a desire to give everyone access to opportunities for autonomy and fulfillment regardless of background.

His approach to purpose extends beyond personal achievement to creating positive change in the world. After achieving financial freedom, Simon realized the importance of helping others and challenging divisive narratives. This shift from pursuing personal gain to facilitating others' success represents his mature understanding of a purposeful life.