Big Failures and Sunken Cost Lessons

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

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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.

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