By Dennis Culloton

Herb Kelleher once drank a plastic cocktail glass of soda after he extinguished his cigarette in it on a dare—well, actually a warning—from me. 

So I hope he will appreciate that I grinned when I read of his passing at age 87 yesterday. 

At a time when it is trendy in business to be considered an innovator and an entrepreneur, Mr. Kelleher, the co-founder of Southwest Airlines was both of those things and more long before it was cool. In fact, trained as a lawyer, his early years were spent fighting the establishment and the big airlines in court as he helped found the original low-fare airline. 

The brilliance of his vision was that it was so simple and clear. Keep costs low so that your customers can afford you. Southwest, to this day, has a fleet comprised only of Boeing 737s to keep parts, service and training streamlined; flies point-to-point to keep the planes in air and tries to fly into lower-cost airports. 

As reported in the Dallas Morning News: “When Southwest started, very few Americans had ever been on an airplane. Today, almost every American has, and it’s no exaggeration to say that’s because of Southwest,” said Seth Kaplan, editor of the industry publication Airline Weekly. “Other airlines mimicked and in some ways took the model even further. But it started there.”

Herb and his fiercely loyal Southwest Airlines associates made air travel available so that more people can see our country—and now some international destinations. To do so while creating an airline that has had more than four straight decades of profitability; tremendous employee loyalty; and an outstanding safety record is even more fantastic.

Today’s business leaders should note he accomplished all of this in a self-deprecating way. Herb never took himself very seriously, which is why he mocked himself as a bed-wetter in a joint press conference with Mayor Richard M. Daley that day in the late 90s. I was the communications director for the Chicago Airport System and we were at Midway Airport where the Mayor unveiled the latest design plans for the new Midway Airport in Chicago. At a reception in the old terminal building which followed, he extinguished his cigarette in a half-drunk beverage. I called out to him: “Don’t accidentally drink that one Mr. Kelleher.”

He looked at me with those wild eyes he displayed in many a Southwest TV commercial and with perfect comic timing, took the glass and and downed it.

No one else saw it. His message seemed to be: “Don’t dare Herb Kelleher, I’m crazy enough to do anything.”

Indeed he was. And we can all learn from him.