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    Artwork for How I Built This with Guy Raz
    Episode

    Square: Jim McKelvey. He Lost a $2,000 Sale, Then Built a $10 Billion Company

    How I Built This with Guy Raz · Feb 16, 2026 · 1 h 16 min

    Most entrepreneurs think the hardest part of building a company is the product. For Jim McKelvey — co-founder of Square — the hardest part was the system around the product. Because Square wasn’t just competing with other startups … It was competing with regulations, middlemen, entrenched networks, and monopolies designed to keep outsiders out. In this episode, Jim shares the mindset and tactics…

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