Jim McKelvey did the impossible. He beat Amazon. The tech giant launched a product similar to Square’s, undercut their pricing, and leveraged its massive brand. Everyone thought Square was doomed. But a year later, Amazon quit and even mailed Square readers to their customers. That left Jim with a bigger question: “How did we survive when no one else ever has?” The search for that answer inspired his book The Innovation Stack, a blueprint for building a business that cannot be copied. In this episode, Jim joins Ilana to reveal the secret to creating an unbeatable business, why ignorance can be a superpower, and how to survive the impossible as an entrepreneur.

Jim McKelvey is the co-founder of Square (now Block), a billionaire entrepreneur, and author of The Innovation Stack. He also founded LaunchCode, a nonprofit providing free tech education and job placement.

In this episode, Ilana and Jim will discuss:

(00:00) Introduction 

(02:04) Growing Up as an ‘Uncool’ Kid in St. Louis

(04:01) The Early Hustle That Jumpstarted His Career

(07:47) Launching a Business with 15-Year-Old Jack Dorsey

(13:50) The Birth of Square: From Glass Blowing to FinTech

(20:09) The Art of Selling and Capturing Attention

(26:48) How a Single Demo Won Over MasterCard

(31:04) Amazon's Failed Attempt to Crush Square

(32:17) The Innovation Stack: Building an Unbeatable Business

(35:55) Why Most Entrepreneurs Give Up Too Soon

(41:32) Why the Best Innovators Are Always “Unqualified”

Jim McKelvey is a serial entrepreneur, inventor, and philanthropist best known as the co-founder of Square (now Block), the fintech company that redefined digital payments. He is the author of The Innovation Stack, which explores how companies can survive by creating solutions that can’t be copied. Jim also founded LaunchCode, a nonprofit that provides free tech education and job placement for aspiring coders. 

Connect with Jim

Jim’s LinkedIn: linkedin.com/in/mckelveyjim

Resources Mentioned

Jim’s Book, The Innovation Stack: Building an Unbeatable Business One Crazy Idea at a Time: https://www.amazon.com/Innovation-Stack-Building-Unbeatable-Business/dp/0593086732