The fun-loving CEO who shook up air travel

Herb Kelleher was not your typical CEO. The Southwest Airlines co-founder and longtime leader would roar into company gatherings on a Harley Davidson or strut in dressed as Elvis Presley. He’d help haul baggage during the Thanksgiving rush, once arm-wrestled another airline boss to settle a legal dispute (he lost), and was often seen with a Kool cigarette in mouth and a glass of bourbon in hand. But behind that hard-living, fun-loving persona was a serious business mind. During his three decades at Southwest, he transformed the company from a low-fare, no-frills upstart serving three Texas cities into the nation’s most popular and profitable domestic carrier, flying more than 120 million passengers a year. In the process, he brought air travel to the masses. “I really don’t believe,” Kelleher said, “that you have to be boring to be successful.” Born in Camden, N.J., Kelleher began his career as a lawyer in his home state before moving to

San Antonio “to start his own firm,” said The New York Times. In 1967, one of Kelleher’s clients, businessman Rollin King, asked if he wanted to help launch “an airline that could fly cheaply within Texas.” Kelleher signed on, and the pair sketched out their idea on a cocktail napkin. Competitors such as Texas International, Braniff, and Continental tried to ground the new carrier, arguing in court that Texas wasn’t big enough to support another airline. But Southwest prevailed, making its first flight in 1971. The carrier kept fares low—$15 for a flight from Dallas to San Antonio, compared with Braniff’s $62— by breaking industry convention, said the Associated Press. “It flew just one kind of plane, the Boeing 737, to make maintenance simpler and cheaper.” There were no assigned seats and no meals. And planes were emptied, loaded, and pushed off the gate in a speedy 20 minutes.

After the federal government began deregulating the airline industry in 1978, “Southwest steadily expanded from Texas to Louisiana, Arizona, California, and, ultimately, nationwide,” said The Washington Post. Other airlines lowered their prices to compete with Southwest, but the carrier retained an edge through its deeply loyal and productive workforce. Southwest has never had layoffs or pay cuts; Kelleher, who retired as CEO in 2001 and as chairman in 2008, said it was good business to “treat your employees like customers.” Because “when you treat them right,” he said, “they will treat your outside customers right.”