From Desperation to Entrepreneurship

This chapter recounts a transformative journey from job rejections to discovering entrepreneurial spirit through gardening services. It highlights the critical importance of perseverance, the impact of that first customer, and the financial challenges faced in a high-cost city like Hong Kong. The narrative further explores the emotional complexities of building and eventually selling a successful business, emphasizing the personal connections and identity tied to entrepreneurial endeavors.

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In this raw and deeply emotional episode, Simon Squibb sits down with Chris Do to unpack the moment he won a $1 million prize—and why it brought him to tears. From sleeping on the streets at 15 to selling a company to PwC, Simon reveals the powerful story of loss, hustle, purpose, and rebuilding from nothing. He challenges what we think we know about money, success, and charity—and makes a compelling case for why anyone, anywhere, can start a business.

This isn’t just a business interview—it’s a masterclass in emotional resilience, reinvention, and the psychology behind purpose-driven work. Whether you're broke, burned out, or just looking for a reason to keep going, Simon’s story will make you believe in possibilities again.

Timestamps:

(00:00) - The dream spark: How Simon helps people start with nothing

(01:30) - The serendipitous $1M moment at the 1 Billion Followers Summit

(03:00) - Why Simon cried on stage (and what people misunderstood)

(06:30) - Childhood trauma: Being kicked out at 15 after his father's death

(09:00) - Billy Elliot, judgment, and the underdog narrative that made him weep

(12:00) - Small-town England to global entrepreneur: Breaking out of expectations

(14:30) - The family divide: estrangement, identity, and redefining connection

(16:00) - Why selling his business felt like another kind of loss

(20:00) - Dealing with hate: tribal psychology and toxic social media reactions

(23:30) - Purpose vs. profit: Why helping for free is Simon’s real power move

(25:00) - From homeless to hustler: how a messy garden became his first business