#110 Jim McKelvey, Cofounder of Square - Innovation When it's Your Only Choice, Overcoming Regulation, and Managing His Intern, Jack Dorsey [ENCORE]

24 Mar 2026 · 63 min
Episode

24 Mar 2026 · 63 min

0:00

In this interview Alisa Cohn talks with Jim McKelvey – glassblower, former St. Louis Federal Reserve chair, and co‑founder of Square (now Block) – about the unlikely path that led him from a struggling glass‑blowing studio to building a $10‑billion payments company. McKelvey recounts how a frustrated sale to a customer who only had an American Express card sparked the idea of turning an iPhone into a credit‑card reader, how he and a teenage intern (Jack Dorsey) built a prototype using the iPhone’s microphone jack, and how they navigated a maze of 17 illegal regulations before achieving compliance. He explains the core of his book The Innovation Stack: a mindset that treats innovation as a last‑resort survival tool, the importance of “being too early” (the herd‑animal intuition), and the role of timing learned from glass‑blowing. The conversation also covers culture at Square – embracing failure, hiring for mission, and the “warrior spirit” that helped them survive an Amazon price‑cut attack and a massive Google counter‑offer. McKelvey shares personal struggles, including panic attacks, imposter syndrome (especially as a minority and as a non‑economist Federal Reserve chair), and the realization that money didn’t change his core motivations. He reflects on the invisible line between copying and true innovation, the need to follow distinct rules for innovative teams, and offers candid leadership advice: solve problems that truly need new solutions, accept the rough ride, and avoid seeking guarantees. Anecdotes about his family’s pilot‑training prank, his love of cheap planes, and his current work on a micropayment venture called Invisibly round out the discussion. Throughout, he stresses that true entrepreneurs feel alone, must build their own solutions rather than copy experts, and that an “innovation stack” creates a protective moat against larger competitors and regulators.

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