Jim McKelvey | Co-Founder of Square and Author of “The Innovation Stack”


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Jim McKelvey is the co-founder of Square, a financial technology company powering millions of small businesses that he launched in 2009 with Jack Dorsey, who’s also the founder and CEO of Twitter. The company debuted on the New York Stock Exchange in 2015 and is currently worth about $53 billion.

Jim is also the author of “The Innovation Stack: Building an Unbeatable Business One Crazy Idea at a Time,” where he breaks down what it truly means to be an entrepreneur and build a world-changing business. It’s one of our personal favorite books that we’ve read in a very long time and we wanted to dive deep into some of the concepts and stories Jim shares in the book, so we definitely recommend picking up a copy if you enjoy this conversation.

We talked about everything from Jim’s personal story and how being an outcast at a young age helped him as an entrepreneur, how he got into glass blowing and eventually opened up his own studio which he still runs today, hiring Jack Dorsey as an intern at his first company and how their relationship has evolved, how losing a sale at his studio gave him the idea for Square, the evolution of the word “entrepreneur” and what it truly means, experience vs. naïveté when it comes to innovation, how he literally built the Square reader and went against Apple’s rule and regulations, the meeting with Steve Jobs that never happened, how they went up against Amazon and won, managing fear and staying motivated, and what his definition of success is.

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163 episodes