School of Hard Knocks Podcast

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RJ Jain is the founder of Price.com, an AI-powered shopping platform valued at around $200 million, and previously sold his last startup to Google for nine figures. In this episode, he shares his journey from growing up in India and studying in Michigan to building and exiting a company, then starting again as a solo founder. He breaks down the reality of startup risk, fundraising, distribution, consumer tech, and how AI is changing execution. This conversation is a sharp look at resilience, ambition, and what it takes to build at scale.

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Richard built HomeServe into a £4.1 billion global company operating in 10 countries, starting with just £50,000 and multiple early failures.
In this episode, he breaks down the near-collapse moments, the pivot that changed everything, and the exact business model that scaled globally.
He also shares his 9-step framework for building a billion-pound company, insights on bootstrapping vs. raising capital, and why copying proven ideas beats chasing originality.
A masterclass in scaling, resilience, and strategic execution.

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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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