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

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 sway investors more than confidence
• How Square survived by building something Amazon couldn’t copy

Timestamps:

• 00:12:26 – Engineering and art: Balancing an IBM job with glassblowing
• 00:15:46 – The family trauma that rewired Jim
• 00:36:26 – Losing a $2,000 sale — the moment Square was born
• 00:43:06 – Breaking into the credit card club: “We were violating 17 rules”
• 00:48:31 – The headphone jack hack that sidestepped Apple’s control
• 00:58:03 – The “140 reasons we might fail” pitch that won over investors
• 01:06:26 – The taxi ride that convinced Jim he had product-market fit
• 01:09:28 – Amazon attacks, and why copying doesn’t always work
• 01:13:18 – The founder’s job after success: choosing hard problems

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This episode was produced by Alex Cheng with music composed by Ramtin Arablouei. It was edited by Neva Grant with research help from Katherine Sypher. Our engineers were Patrick Murray and Robert Rodriguez.

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