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

De: Guy Raz | Wondery

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 purposeHow a simple hack can solve a seemingly complex problemHow candor can sway investors more than confidenceHow Square survived by building something Amazon couldn’t copyTimestamps:00:10:01 – Engineering and art: Balancing an IBM job with glassblowing00:13:21 – The family trauma that rewired Jim00:34:01 – Losing a $2,000 sale — the moment Square was born00:38:26 – Breaking into the credit card club: “We were violating 17 rules”00:43:51 – The headphone jack hack that sidestepped Apple’s control00:53:23 – The “140 reasons we might fail” pitch that won over investors01:00:16 – The taxi ride that convinced Jim he had product-market fit01:03:18 – Amazon attacks, and why copying doesn’t always work01:07:08 – The founder’s job after success: choosing hard problems*** Hey—want to be a guest on HIBT? If you’re building a business, why not get advice from some of the greatest entrepreneurs on Earth? Every Thursday on the HIBT Advice Line, a previous HIBT guest helps new entrepreneurs work through the challenges they’re facing right now. Advice that’s smart, actionable, and absolutely free. Just call 1-800-433-1298, leave a message, and you may soon get guidance from someone who started where you did, and went on to build something massive. So—give us a call. We can’t wait to hear what you’re working on. *** 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.©2026 Guy Raz | Wondery (P)2026 Guy Raz | Wondery