James Mckelvey on entrepreneurship
From 013: Solving Billion-Dollar Problems – Jim McKelvey · · Tony Maree Torrey
“the definition that i needed to write the book so first of all i didn't even want to write a book i generally don't like business books and i didn't want to write another one but i found this thing that i thought was just super super powerful and then i basically got a homework assignment from herb keller who was one of the people i interviewed for the book herb said look you got to write this and so out of respect for herb i wrote it but in order to write the book what i realized was that i needed to have a word to describe a business person who was not copying what everybody else was doing”
On , James Mckelvey, Co-Founder & Director at Square, spoke about entrepreneurship during 013: Solving Billion-Dollar Problems – Jim McKelvey on Tony Maree Torrey.
About James Mckelvey
Jim McKelvey, co-founder of Square (now Block, Inc.), has been speaking publicly about his concept of the "Innovation Stack" and the early challenges of building Square. In a March 2026 podcast, he recounted that Square started after he lost a sale at his glass studio because he could not accept an American Express card, and that in the first week of operation he found 17 laws or rules Square was violating. He described Amazon's later attempt to copy Square with Amazon Register and said the threat led him to write a book about how innovation forces a company to invent rather than copy. McKelvey also discussed the emotional difficulty of innovation, noting that "the first time any human does anything, that person is unqualified" and that meaningful innovation is rarely comfortable or cool. In April and May 2026 appearances, McKelvey reflected on his personal history, including his mother's suicide and his experience as an outsider. He said that being unpopular as a child gave him an advantage in not caring what others think, and that he has "been kicked out of everything I've started" because he gets bored once a venture is built. He also described his approach to layoffs at Square, stating that the company avoided small, repeated cuts and instead conducted a single org-wide reduction with six months' severance plus a week per year of service. McKelvey continues to promote the idea that true innovation arises when copying is impossible, and that entrepreneurs should embrace the demoralizing, failure-laden process that comes with building something new.