Herb Kelleher will be remembered by many as a man who reshaped the airline industry. No doubt he was a big thinker on the U.S. and even the world stage. Herb was a bigger-than-life Texan and seemed to be a caricature of himself.
Others can write that story, but I would like to offer a personal view of Herb as a friend, mentor and someone from whom we should all learn. I first met Herb in the early 1980s. He was a director of a public company, and I became the largest shareholder and ultimately chairman of that company. We became friends, and Herb along with his fellow director and co-founder, David Florence, have both been instrumental in my life.
Over the years, Herb and I had shared running jokes that were perhaps examples of his wit and humor. Several years ago, Herb was receiving the Spirit of Entrepreneurship award from the Communities Foundation of Texas and asked me to join him in the green room for a drink before he accepted. He proceeded to pour each of us a very large glass of vodka with no mixers or even ice, for that matter. To those around us it looked like a tall glass of water, but I assure you it was not.
When it was time for Herb to go on stage and receive his award, I made my way to the front row to watch. I had previously received this award and from my recollection it was an informal, no-tie event. I found myself surrounded by a room of well-wishers for Herb all wearing ties except for me. When Herb started his speech, in a joking manner he immediately stated, “My friend Hall obviously can’t afford a tie.”
Shortly after the event, I received a handwritten note from Herb and one of the ugliest ties you could ever imagine. The note in part read, “The attached tie screamed ‘Craig Hall’ to me as I walked through the men’s department at Kmart. I know you will cherish it and care for it. Best, Herb.”
I have saved this and other Herb notes, as I call them, over the years.
In years since, Herb sent me another very ugly tie with another great note that included encouragement on a new Hall wine we were producing called Craig’s. In the letter, he talked about sharing the Craig’s wine with a drinking buddy from New York University law school, who he recalled as primarily having a love for drinking Annie Green Springs, a very cheap wine. His friend pronounced my wine as “very good.” Another time, he sent a note about how I should market our high-end Hall Arts condominiums to “Russian bureaucrats who have lots of offshore money to spend on lavish condos.”
While Herb’s wit and humor are legendary, that’s not the real Herb Kelleher, from my perspective. In 1986, a few short years after I met Herb, my life had been turned upside down by dramatic business reversals. My company was in deep trouble, and I was frequently in the news in a very negative light. Most of my friends had abandoned me, and frankly it was the loneliest, toughest time of my life. One of the few people who would call and take me out to dinner and encourage me to keep on fighting to survive was Herb Kelleher. I was not rich and famous, and he had no obligation to be kind to me except for the fact that he was a very genuine, kind and caring person.
Among many other lessons I take away from Herb Kelleher is that authenticity and being a caring, real person matters. Herb helped reshape the airline industry and created many jobs. He improved the lives of many people because he really cared. Herb wasn’t greedy or selfish; he was successful by being the opposite. His giving and love for others extended far and wide.
Let me take you back to the Spirit of Entrepreneurship event that I mentioned earlier when Herb was receiving an award. Herb was interrupted during his speech by an airline union group. In a typical situation when an executive is receiving an award and is interrupted by the union, it would be for the purpose of a complaint. In this case, the union brought out a $250,000 check that they had raised as a tribute to Herb from people who worked for Southwest Airlines and loved Herb. They wanted to give the money to the Ronald McDonald House in Herb’s honor, which was a charity near and dear to him.
Herb was an authentic, genuine, caring, and loving, wonderful human being. If we all lived our lives a little more like Herb Kelleher, the world would be a much better place.
This article was originally appeared on Dallas News.