From Homeless Teen To Millionaire Founder: Simon Squibb Reveals How To Change Your Life Fast

From homeless teen to multi-millionaire entrepreneur, investor, and mentor to millions, Simon Squibb has lived one of the most extraordinary entrepreneurial journeys of our time. In this episode of The Burnouts, Simon Squibb sits down with Phoebe Gates and Sophia Kianni to unpack how losing his father at 15 and spending weeks homeless reshaped his view on success, purpose, and money. He opens up about sleeping on the streets, starting his first business out of survival, and building a creative empire that led to financial freedom, and a mission to help 10 million people start businesses through his “Give Without Take” movement. Simon reveals the mindset shifts that turned trauma into drive, why he believes happiness is a trap, and the three sales principles that made him a millionaire. He also shares what most entrepreneurs get wrong about mentorship, why purpose matters more than profit, and how “bad luck” can be your greatest advantage. Whether you’re just starting out, stuck in a 9-to-5, or dreaming of building something that actually matters, this conversation is packed with raw honesty, purpose-driven wisdom, and actionable lessons from one of the internet’s most followed business voices. Chapters 00:00 – From homeless teen to entrepreneur 03:00 – Losing his father at 15 and becoming homeless 06:00 – The first business that changed everything 10:00 – Learning to sell (and why school failed him) 15:00 – The truth about happiness and purpose 19:00 – How Hong Kong taught him work-life integration 25:00 – Building and losing companies (and learning from failure) 30:00 – Mentorship myths & why advisors matter more 35:00 – The 3 sales principles that made him a millionaire 40:00 – Why purpose > happiness 44:00 – The one question everyone in their 20s should ask 🔗 FOLLOW US Phoebe Gates Sophia Kianni Simon Squibb 🔥 FOLLOW THE BURNOUTS Instagram TikTok LinkedIn 📲 Support What We’re Building Phoebe and Sophia aren’t just your hosts—they’re the founders of Phia, a new fashion-tech app helping shoppers find the best prices across retail and resale. Download the app , try it out, and help us grow this community About the Burnouts The Burnouts brings you raw, unfiltered conversations with today’s top founders, creators, and culture-shaping entrepreneurs. Hosted by Stanford roommates turned startup co-founders Phoebe Gates and Sophia Kianni, the show goes beyond the headlines to share the real stories, lessons, and mindsets that define your 20s. Past guests include Kris Jenner, Paris Hilton, Chelsea Handler, Karlie Kloss, and other visionaries redefining what success looks like. Subscribe now for the insider playbook to build your dream career. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.