Remembering the Legendary Herb Kelleker

Today we are taking a moment to remember Herb Kelleher, the legendary co-founder of Southwest Airlines, who passed away yesterday. Kelleher practically invented low-fare air travel and revolutionized the airline industry. According to legendary Texas businessman T. Boone Pickens “Herb Kelleher is arguably the most transformative figure and character in the history of modern aviation. He is the epitome of the can-do entrepreneurial spirit.”

Herb was a lawyer by training. In 1967, his client, Rollin King, suggested the idea of a low-cost airline between San Antonio, Houston, and Dallas. Herb loved the idea. For four years, he overcame the legal obstacles imposed by established airlines allowing Southwest to launch its first flight in 1971. Southwest flew from less congested airports to avoid costly delays. It kept maintenance costs low by flying just one plane – the Boeing 737. It has no assigned seats and doesn’t serve any meals – unless you count peanuts and pretzels. By 1973, Southwest was in the black and hasn’t suffered a loss since — a streak that no other U.S. airline can match.  According to Herb, his proudest achievement was that Southwest Airlines never laid off workers, when the airline industry cut tens of thousands of jobs in the decade after 2001.

But that’s not my favorite thing about Herb Kelleher. What I love is the culture he created. As a customer, you could tell Southwest was different from the moment you stepped on one of their planes (in my case this included the flight attendant sensing I might benefit from a pre-flight relaxant and in the form of a cold beer) to the surprising way the flight attendants applauded when the plane finally touched down in the destination city. Southwest was also the first airline to bring a little life to the typically serious (and largely ignored) FAA warnings and instructions. (Check that out here.)

And that awesome Southwest culture came from the top – right from Herb. How many CEOs can you think of who would settle a business dispute with an arm-wrestling contest or go on TV wearing a paper bag over their head? Not many. But Herb did.

Herb loved a chance to engage in creative and hilarious marketing antics. When Braniff tried to drive Southwest out of business by cutting its fares below actual costs, Kelleher offered a bottle of liquor to anyone who bought a full-fare Southwest ticket. Kelleher joked that Braniff made Southwest the biggest liquor distributor in Texas at the time.

When Southwest and Kurt Herwald, the chairman of Stevens Aviation (a tiny aircraft sales company) both claimed the same advertising slogan – “Just Plane Smart,” Stevens’ CEO proposed to settle the dispute by arm-wrestling Kelleher rather than suing Southwest. Herb accepted. In response to weight-training videos circulated by Stevens’ CEO, Herb claimed that, like a true Texan, he would defeat his opponent with brute strength relying only on pulls from a bottle of Wild Turkey bourbon to train for the match. On March 20th, 1992, Herb and Kurt arm-wrestled in front of a crowd at the Dallas Sportatorium in what was called the “Malice in Dallas.” Clenching a lit cigarette between his teeth, Herb lost the match. Stevens’ CEO (secretly a huge fan of Herb and Southwest and impressed by the publicity the stunt generated) agreed to let Southwest keep using the slogan. 

As Southwest grew, executives at Southwest’s competition derided Southwest as a cattle-car operation. Kelleher responded with a TV commercial wearing a paper bag over his head and promised to give the bag to any customer who was too embarrassed to be seen flying on Southwest.

What is it about Kelleher that made him such a great leader? Passion and productivity for sure. But it was his playfulness that made him unique. Southwest became the great airline it is because of the tone set by this unconventional and unapologetically authentic man.

Even though wildly successful, Herb never took himself too seriously. In Herb’s honor, we can vow to be a bit more playful in our lives and in our work. And, we can think of Herb when we see the heart on the side of America’s favorite airline. Herb, you will be missed. RIP.

***Standard disclaimer: Written on the fly. Please excuse spelling and grammatical errors as well as partial thoughts, generalizations, and unintended whiplash.


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