Farewell to an Iconic Entrepreneur

On January 3, 2019, one of the legendary icons of entrepreneurship stepped on a rainbow. Herb Kelleher died at age 87 after living a storied life. Kelleher famously co-founded Southwest Airlines in the late 1960s. He was practicing law in San Antonio when a client brought him an idea to launch a new airline in 1967. Competing airlines did everything they could to prevent the new airline, originally incorporated as Air Southwest Company, from getting off the ground. Lawsuits were the only thing flying for several years, and at one point the board told Kelleher that the venture needed to be shut down. Kelleher offered to fight the lawsuits and pay the court costs out of his own pocket at which point the board agreed to stay in business. It took four years and victories at both the Texas and the U.S. Supreme Courts – twice – before Southwest Airlines flew for the first time on June 18, 1971. His resilience and tenaciousness are credited for enabling Southwest to persevere and become the major airline that it is today.

Kelleher was general counsel and served on the board of directors, becoming chairman in 1978. In 1981 he became the full-time CEO and built the airline into a powerhouse as a result of his vision. At the time, the airline industry was highly regulated and when an airline started losing money, it would petition the Civil Aeronautics Board (CAB) to allow for a fare increase. As a result, it became exceedingly expensive for the public to fly – something that Kelleher saw as the opportunity of a lifetime. Initially Southwest was an intrastate carrier flying within Texas, making flying between Dallas, San Antonio and Houston affordable through ultra-low fares. Over the years the airline started flying outside the state of Texas but was hamstrung by the Wright Amendment – legislation designed to help the legacy carriers and hurt Southwest. The law required that Southwest could not fly from another state directly into Dallas’ Love Field without first stopping in an immediately adjacent state including Arkansas, Louisiana, Oklahoma and New Mexico. I can remember flying from Kansas City to Dallas and having to stop in Oklahoma City to change planes because of this requirement. Eventually the Wright Amendment was defeated in Congress and Southwest was able to operate like any other airline in the country.

Kelleher was a marketing genius and employed numerous outrageous stunts that endeared Southwest to its employees and to the public. He never took himself too seriously and is well known for his love of Wild Turkey bourbon and a daily dose of five packs of Marlboro cigarettes. When it came to compensation, Kelleher chose to take less in cash salary and more stock options. This approach helped considerably with the Southwest labor force (where the CEO was not receiving an exorbitant level of pay) and made him a billionaire two-and-a-half times over. He claims to have been a “flamboyant marketer but was fiscally conservative.” His shrewd financial prowess put Southwest on a path to profitability that is unmatched by any other airline – and few public companies in any industry. Since 1973, the company has been profitable every single year.

For decades, the culture at Southwest Airlines has been studied under a microscope by business schools and business leaders. It’s safe to say that Kelleher defined and sustained that culture for the 20 years he was the CEO and even after he retired in 2001 (he remained chairman of the board until 2008). He spent an enormous amount of time talking to employees and gaining understanding for what was working and what needed to be fixed. He loaded baggage onto planes every Thanksgiving Day; met technicians at 2:00 AM in a maintenance hangar; visited operators at reservation centers and spent time as a gate agent. According to Terry Maxon, in a 2015 article for the Dallas News, Kelleher dressed up like Elvis Presley, a woman, the Easter bunny, a leprechaun and a flight attendant to promote Southwest. Maxon went on to explain the corporate culture was that of a 1) scrappy underdog to the public; 2) fierce warrior to its competitors, and 3) warm, supportive and protective atmosphere for the employees.

Herb Kelleher was a larger-than-life model for us as entrepreneurs to emulate. He had all the requisite entrepreneurial traits – vision, tenacity, resilience, marketing skills, financial acumen, a cultural leader and a genuine love for people. Above all he had a passion for life. They broke the mold when Herb Kelleher left this planet. R.I.P.

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This blog is being written in tandem with my book, “An Entrepreneur’s Words to Live By,” available on Amazon.com in paperback and Kindle (My Book), as well as being available in all of the other major eBook formats.