Square: Jim McKelvey. He Lost a $2,000 Sale, Then Built a $10 Billion Company

Jim McKelvey, co-founder of Square, recounts the company's origins and the challenges it overcame. McKelvey details how a personal frustration—being unable to accept American Express for his glass art—led to the idea of a mobile credit card reader. He describes Square's early days, including hiring Jack Dorsey as an intern and navigating the complex regulatory landscape of credit card processing. McKelvey also discusses the near-fatal threat posed by Amazon's entry into the market and how Square's unique "innovation stack" allowed it to survive. A personal tragedy, his mother's suicide, shaped his relentless drive to address problems and his approach to business.