The Million Dollar Moment That Changed Everything - With Simon Squibb (Part 1) | Episode 348

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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

(29:00) - Scaling with no resources—and becoming the first customer himself

(34:00) - Selling his agency to PwC and losing his “fluid” identity

(40:00) - Depression post-success: What happens when you no longer “need”

(44:30) - Purpose as survival: Why not needing money can leave you lost

(49:00) - Giving without expectation—Simon’s philosophy on modern generosity

(52:00) - Why building a business to help others is the future of entrepreneurship

Check out today's guest, Simon Squibb:

Simon's LinkedIn: https://uk.linkedin.com/in/simonsquibb

Simon's Instagram: https://www.instagram.com/simonsquibb/?hl=en

Simon's Website: https://simonsquibb.com/

Check out The Futur:

Website: https://www.thefutur.com/

Courses: https://www.thefutur.com/shop

Linkedin: https://www.linkedin.com/company/the-futur/

Podcasts: https://thefutur.com/podcast

Instagram: https://www.instagram.com/thefuturishere/

Facebook: https://www.facebook.com/theFuturisHere/

Twitter: https://x.com/thefuturishere

TikTok: https://www.tiktok.com/@thefuturishere

Youtube:https://www.youtube.com/thefuturishere

Check out Chris Do:

Website: https://zaap.bio/thechrisdo

LinkedIn:https://www.linkedin.com/in/thechrisdo/

Facebook:https://www.facebook.com/BizOfDesign

Instagram:https://www.instagram.com/thechrisdo/

Twitter:https://x.com/thechrisdo

TikTok:https://www.tiktok.com/@thechrisdo

Threads:https://www.threads.net/@thechrisdo

Zaap: https://zaap.bio/thechrisdo

Clubhouse:https://www.clubhouse.com/@thechrisdo

Behance: https://www.behance.net/chrisdo