Intro

This chapter explores the theme of pursuing one's dreams and the pivotal moments that can spark motivation. It features a personal story of an unexpected windfall that highlights the intersection of ambition and destiny.

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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