E15 - #14 How Herb Kelleher Built Southwest Airlines with Heart

In a world where most CEOs wore suits and spoke in corporate jargon, Herb Kelleher showed up in a t-shirt, laughed loudly, and built one of the most successful airlines in history by doing everything the “experts” said was crazy.

This episode explores the remarkable story of Herb Kelleher, the legendary co-founder and longtime CEO of Southwest Airlines, and how his unconventional leadership reshaped the airline industry—and American business itself.

When Kelleher and his small team set out to launch Southwest in the early 1970s, they didn’t have the money, planes, or political backing...