Episode 18

Follow Your Frustration: Jim McKelvey on Originality and Innovation

March 31st, 2026

47 mins

Season 3

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About this Episode

Today on The Owner’s Box, we are joined by Jim McKelvey. Jim is probably best known as the co-founder of Square, the payment technology company he built alongside Jack Dorsey that went on to reshape how small businesses accept payments. You may not know that Square is in a very small cadre of companies that Amazon tried to copy and couldn't, which Jim illuminates in his recent book, The Innovation Stack.  On today’s episode, Originality and Impact with Jim McKelvey.