Today Southwest is the eleventh-largest airline in the country and one of the strongest carriers in the nation. In salary alone he makes almost $400,000 a year, and he is Southwest’s largest individual shareholder, owning 441,465 shares worth roughly $5 million. Herb Needs the Money.” It worked Southwest has made Kelleher-who is the president, the chairman of the board, and the chief financial officer-a rich man. Years ago Southwest issued bumper stickers that said: “Fly Southwest. Kelleher is living proof that the airline has made commuter marriages possible: he lives in Dallas, his wife, Joan, lives in San Antonio, and they see each other on weekends via Southwest. You can leave Harlingen or Dallas on a morning flight and do a deal in Houston over breakfast. The distance between any two of the ten major cities in Texas linked by Southwest is roughly 55 minutes. Southwest has radically altered our psychic landscape. Its virtual monopoly of the Texas commuter market has made it a modern-day cattle drive, the primary means of getting our goods-that is, ourselves-to market. By making flying around Texas easier than driving, Southwest immediately achieved the impossible-it separated Texans from their cars. Since June 18, 1971, when Southwest made its first flight from Dallas to San Antonio with ten paying customers, Texas has never been the same. There may be no food, no closets, no leg space, but at seven-thirty in the morning, you’re belted in your seat, laughing like a perfect fool. “As soon as y’all set both cheeks on your seats, we can get this old bird moving,” comes the microphonic twang from the front of the airplane. They give you safety information in rap, sing Christmas carols, or tell you the wrong time on purpose. They are dressed in everything from baggy shorts and wild-print shirts to reindeer outfits. The big-haired flight attendants all look like they went to the same West Texas high school. Then it starts: the Southwest Experience. You just want to drink your coffee, read your memos, and get to your meeting. To understand that the man and his airline are one, all you need to do is get aboard one of his planes. In an industry beset by turmoil and takeovers, Southwest thrives by making its own rules. The airline he helped found and now runs is a direct extension of that personality-Kelleher himself often stars in the company’s offbeat commercials. The meeting epitomizes the Kelleher personality: his irreverence, his spontaneity, his zaniness, and, most of all, his competitiveness. “Why not make United the official airline of Popeyes fried chicken?” he suggests. Kelleher suggests taking a poke at United, which not only does not have an affiliation but also just lost its place as the largest airline. Kelleher’s own Southwest Airlines could be creative fodder for this one in 1988 it became the official airline of Sea World. Someone suggests a musical parody: “The Lady is a Trump.” Then Kelleher lights on the battle for the entertainment-park business. The focus shifts to New York deal-maker Donald Trump and his attempt to purchase the Eastern Airlines Shuttle, which runs between Boston, New York, and Washington. Bob,” Kelleher says, mimicking the tiny sex doctor, “size isn’t everything.” Ruth would be on the telephone talking to Robert Crandall, the abrasive head of Dallas-based American Airlines, which has just become the largest domestic carrier. The task at hand is to come up with skit ideas for an airline-industry conference. Kelleher is brainstorming with three of his top managers in his cluttered Southwest Airlines office near Dallas’ Love Field. Ruth spoof,” says Herb Kelleher, jumping to his feet in a spasm of creativity.
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