They Just Don’t Make ‘em Like that Anymore

Originally published on January 9, 2019 by the Montrose Daily Press.

My phone is constantly buzzing with various notifications, to which I typically pay little, if any, attention. However, early last week I happened to see a news notification with “Herb Kelleher” in the same headline as “dies.” My heart immediately dropped. Kelleher founded Southwest Airlines in 1971. Lawyer turned airline boss, Kelleher put more than a “mark” on the airline industry and American business practices. I nearly wrote, “Herb was the Steve Jobs of the airline industry,” but honestly, Herb was Herb Kelleher, a standalone icon and idol to many, present company included.

Kelleher, his rogue approach to leadership, and his Herb-flavored company culture will be missed. As a tribute, here are the top five reasons Kelleher’s legacy shall live on:

1. He believed that if you take care of your people, they will take care of your customers, which will in turn take care of your shareholders (or your bottom line). He hired people intentionally for their ability to do this for customers and teammates alike — pilots who were just as content loading luggage as they were flying the plane. He paid people well, threw them extravagant parties,and devoted himself to simply making them happy.

2. He was never afraid to be David in a fight with Goliath.

“Southwest Airlines would not be in existence today had not the other carriers been so rotten, trying to sabotage us getting into business, and then trying to put us out of business once we got started,” Kelleher said in 1985. “They made me angry. That’s why Southwest is still alive. I’m not going to get beaten, and I’m not going to let anyone take advantage.”

In one such battle, legally trained Kelleher single-handedly fought for Southwest all the way to the Texas Supreme Court. His antics also included responding to the big airlines with cheeky TV ads that called out the airline giants’ shady practices right on the public carpet.

3. Kelleher gave zero craps about being anyone but Kelleher. In an interview with Guy Raz on NPR’s “How I built This,” Kelleher mused about being a lifetime smoker, enjoyer of Wild Turkey whiskey and eater of cheese crackers for breakfast. How can you not smile just a little about that? They don’t really make ‘em like that anymore.

4.He knew absolutely nothing about the airline industry when he founded Southwest. He told people that made him perfect for the job because he went about things as they made sense to him, not because that is how the industry had always done it. In fact, he did (and Southwest continues to do) things that had his competitors squirming in their ivory towers.

Every Southwest plane is exactly the same, and every seat is created equal making for efficiencies previously unheard of. There are no seat assignments. Fares are actually affordable, and Southwest broke the “hub and spoke” model traditionally used by the airline industry. Got baggage? No problem. Two bags fly for free on Southwest. For free. In flight snacks are simple, but they’re free too. Southwest was the first to dump the in-flight meals and extravagant drink service. Kelleher drove the company to continually keep costs down and authentic customer experience up.

5. He had fun, and he shared it with his staff and customers. According to an article recently published in the Dallas Morning News, “He dressed up as Elvis Presley, performed rap songs on training tapes and starred in self-deprecating TV commercials in which he missed his plane, tried to use an expired credit card and claimed credit for the company’s success to employees’ eye rolls. A chainsmoker with a penchant for Wild Turkey bourbon, he also joined employees in passing out peanuts or loading bags on flights.”

Southwest company culture prescribed fun to its employees by encouraging them to crack jokes, sing songs over the speakers, and genuinely surprise and delight people with their unique personalities. If you want your day made, search YouTube for “Hilarious Southwest Flight Attendant” for one such example.

As an aside, that video has had over 24 million unpaid views on YouTube. Pure marketing genius. I guess that whole “having fun at work” thing must be working for Southwest.

“His vision for making air travel affordable for all revolutionized the industry, and you can still see that transformation taking place today,” Southwest CEO Gary Kelly said in a statement, “His legacy extends far beyond our industry and far beyond the world of entrepreneurship. He inspired people; he motivated people; he challenged people — and, he kept us laughing all the way.”

Rest in peace Mr. Kelleher. Say hi to Steve for me.

Chelsea Rosty is the director of business innovation for The City of Montrose. She can be reached at