Why Southwest Airlines founder Herb Kelleher was one of the greatest CEOs ever

Andy Serwer
·Editor in Chief
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Southwest Airlines Chairman Emeritus Herb Kelleher prepares to blow a kiss to the audience at the company's annual shareholders meeting at their Dallas headquarters, Wednesday, May 20, 2009. (AP Photo/Mike Stone)
Southwest Airlines Chairman Emeritus Herb Kelleher prepares to blow a kiss to the audience at the company's annual shareholders meeting at their Dallas headquarters, Wednesday, May 20, 2009. (AP Photo/Mike Stone)

One time I went to interview Herb Kelleher in his office at Love Field in Dallas.

It was morning and I went in and sat down across his desk. I noticed a big bowl of candy bars on the desk right in front of him. A variety, but I distinctly remember a bunch of PayDay bars. I asked him why he had a bowl of candy bars on his desk.

“Oh I like to drink a lot,” he said. “And these babies help in the morning. Want one?” With that he grabbed a PayDay and tossed it to me, and he grabbed another one for himself.

That night I went to a bar with him along with Gordon Bethune, then CEO of Continental (UAL), another larger-than-life character. The three of us drank Wild Turkey 101 on the rocks (Herb’s favorite) until I couldn’t see. Herb and Gordo enjoyed that very much. I staggered out. They continued on.

Besides that, Herb was an incredible CEO. A visionary really. Southwest Airlines (LUV) was his brainchild. A company and a concept that revolutionized the airline business. Same aircraft. No reserved seats. Direct flights. All that.

At one point Southwest had all the profits in the airline business for more than an entire decade. All of it! Look it up.

Clad in jeans and a plaid shirt, Southwest Airlines chairman Herb Kelleher, attends a luncheon meeting with his employees at Dallas headquarters May 8, 1996 where every day is dress-down day. What began as a tiny commuter serving three Texas cities with four planes and 190 employees has grown to 224 planes and 21,000 employees. Now serving 23 states and serving 48 cities, the airline celebrates its 25th anniversary in June. (AP Photo/Tim Sharp)
Southwest Airlines' Herb Kelleher attends a luncheon meeting with his employees at Dallas headquarters May 8, 1996 where every day is dress-down day. (AP Photo/Tim Sharp)

Herb was also a great leader. People loved working for him. He wasn’t flashy or loud. He was just cool. And smart. Super smart. He seemed to me like a classic laconic shrewd Texan. I later found out he was from New Jersey. Oh well: a classic laconic shrewd New Jerseyan.

Herb was a straight shooter. There was no bull. Just results.

RIP Herb.

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Andy Serwer is editor-in-chief of Yahoo Finance. Follow him on Twitter @serwer.

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