Starcast Join the waitlist
How I Built This with Guy Raz

How I Built This with Guy Raz

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

Feb 16, 2026 · 1h 16m

Coming soon to iPhone. Already have it? “Listen in Starcast” takes you straight there.

On this episode

About this episode

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 company—now known as Block— that generates over $10 billion in gross profit. What You’ll Learn: Why the market is often “locked” on purpose How a simple hack can solve a seemingly complex problem How candor can…