Crazy Herb at Southwest Airlines

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Herb Kelleher, the founder and chairman emeritus of Southwest Airlines, is at his desk wearing a white Stetson and pouring a shot of Wild Turkey. He’s got that friendly Texas why-don’t-you-join-me shine in his eyes. Business can wait.

That image of Herb is the photo in a recent issue of Fortune. The headline reads “still crazy after all those years.” Crazy old Herb, a crazy-like-a-fox lawyer who took a start-up airline some four decades ago and turned it into the largest carrier of domestic passengers in the U.S. with 3,400 flights a day using the largest fleet of 737s in the world (575 and counting).

Southwest is arguably the greatest business aviation success over the last 40 years. The history includes a laundry list of airlines that were hostile to frivolity and fun and then sunk without bubbles.

25_Gumwrappers1In the beginning, 1967, Herb tried to shortcut federal aviation regulators by staying within Texas airspace. There was a lengthy legal battle with Continental, Braniff and Tran-Texas airlines trying to keep Air Southwest Co. (changed to Southwest in 1971) on the tarmac. Herb won and the fight resulted in a neat children’s book called Gumwrappers and Goggles. (Big planes try to keep little plane from hanger.)

With old-school sensibilities, Herb hired attractive flight attendants and dressed them in hot pants and underwired bras. Flights were like a night at the Chicken Ranch. (But he also selected the first African-America chief pilot in 1980). Love Field was home base and they had to stay within Texas before opening a non-stop route from Love Field to Birmingham, Ala. Today they service 78 (and counting) destinations.

Along the way, Southwest acquired Muse Air, Morris Air and most recently AirTran. He wisely hedged fuel costs and remained at Love Field. (To drive there today you travel Herb Kelleher Way.)

Here’s a revealing story about Herb. In 2008, Dallas-based American Airlines and Southwest held their annual stockholder’s meeting on the same day. Both airlines were in contract negotiations. AA flight attendants and pilots picketed the meeting. Southwest pilots took out a full-page ad in USA Today: The pilots of Southwest Airlines want to express our sentiment to Herb that it has been an honor and a privilege to be a part of his legacy. What a concept. They stung him with kindness.

Therein, perhaps, is Herb’s real skill – he knows he’s in the people business. He likes to say he treats his employees as customers. He knows the names of employees and even their pet’s names. Some of the losing airlines were veterans of dipstick etiquette and do your homework, make your bed reasoning.

Herb has a lot of Will Rogers-witticisms and wise insights on the airline industry. You can’t help but like the guy. Any sports writer will tell you the best stories are in the loser’s locker room, but the soft-profiled Fortune piece is a good read.

Herb, my dog’s name is Bella.

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