How I Built This
Square: Jim McKelvey. He Lost a $2,000 Sale, Then Built a $10 Billion Company
Feb 23, 2026
· 1h 11m
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 that helped Square go from a tiny card reader that processed credit card payments … to a …
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