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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