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

We want to hear from you. If you're open to a quick chat with our producer or any of the other options, it only takes a few seconds to sign up: https://forms.gle/Enzzpq5FCVQKbHV9A 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 Learn more about your ad choices. Visit megaphone.fm/adchoices