School of Hard Knocks Podcast

Simon Squibb is a self-made entrepreneur worth hundreds of millions who has invested in over 80 companies. After becoming homeless at 15, he built his first business with just £200 and no formal education in business. In this episode, he shares the raw truth about failure, survival, and building from nothing. He breaks down why traditional education fails, why purpose matters more than money, and what it really takes to succeed. This is a conversation about ownership, resilience, and creating your own path.

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Alison and Stephen Ellsworth, founders of Poppi, share how they went from early-stage struggles and personal health challenges to building and exiting a $2 billion beverage company. They discuss risking financial stability, validating their product through real customers, leveraging viral content for growth, and navigating the realities of scaling a business as a married couple. This episode explores entrepreneurship, brand building, leadership, and the mindset required to sustain long-term success.

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Bill Gurley, legendary venture capitalist and early investor in Uber and Zillow, shares the principles behind identifying billion-dollar companies. He reflects on missing the Google opportunity, lessons from evaluating thousands of founders, and why execution consistently beats ideas. The conversation explores network effects, founder psychology, venture capital decision-making, and how young investors can build an edge in emerging industries.

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John Caudwell, founder of Phones 4u, built a billion-pound empire from scratch and exited for £1.5 billion after two decades of relentless growth. Starting with monthly losses and facing near collapse after losing 95% of his supply, he rebuilt through sharp commercial instincts and strategic hiring.
In this episode, he shares lessons on scaling to 10,000 employees, hiring elite talent, navigating ruthless suppliers, and building wealth on thin margins. He also discusses philanthropy, legacy, and why success ultimately goes beyond money.

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Robert Croak is the founder of Sillybandz, the global toy brand that exploded into one of the biggest product crazes of the 2010s, selling billions of units worldwide. In this episode he shares the story behind discovering the idea in China, scaling from 17 to over 3,000 employees, and building a brand that reached hundreds of thousands of retail stores. Croak also breaks down lessons on entrepreneurship, venture investing, product-market fit, and the wealth habits that separate successful founders from the rest. This conversation dives deep into execution, failure, and building businesses that scale globally.

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