Deeply Driven: Business History Insights from Entrepreneurs

Discover how John D. Rockefeller's hardscrabble childhood—caught between a devout Baptist mother and a con artist father—forged the relentless drive and strategic cunning that built Standard Oil into the largest monopoly in American history.

Jim Casey became his family's sole breadwinner at age 11, and through 76 years of relentless work, built UPS into a global delivery empire by focusing on one simple principle: exceptional service compounds over time. Starting from a basement office below a Seattle saloon in 1907, Casey's unwavering commitment to "the sum of many little things done well" created a company culture so powerful it took 68 years to achieve his vision of nationwide delivery—and continues to thrive today.

Samuel Cunard didn’t set out to dazzle; he set out to be on time. This episode shows how a quiet operator from Halifax built an “ocean railway” of steamers, turned reliability into an unbeatable moat, and shrank the Atlantic for commerce, family, and nations alike.

This episode explores how Herb Kelleher, the maverick founder of Southwest Airlines, built a legendary people-first culture that makes him a business history Legend. Drawing upon lessons from the book Nuts, it shows us how passion, humor, and servant leadership can turn our visions into lasting success.

From a five-and-dime store in rural Arkansas to the largest retailer in the world, Sam Walton’s journey is a masterclass in purpose-driven entrepreneurship. His life’s work proves that the most powerful lessons in business history are often simple and deep.