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.

Ted’s Song

Southwest Airlines has been in business since 1967 and has recorded 43 consecutive years of profitability. The company flies 707 Boeing 737 aircraft with 278 more on order. Southwest pioneered low-cost air travel and has grown to be one of the largest airlines in the world. United Airlines launched Ted, its low-cost brand in 2004 with 56 Airbus 320 aircraft. It folded operations in 2008. Delta Airlines launched Song, its low-cost brand in 2003 with 47 Boeing 757 aircraft. It folded operations in 2006.

How is it that two enormous legacy air carriers failed to challenge Southwest with similar low-cost service? Just like Southwest, they flew point-to-point routes. They used a single type of aircraft, just like Southwest. And they charged low fares, just like Southwest. What’s more, they had massive financial backing from well-established parent companies. All three companies were playing a commodity game. So why did Southwest win the game?

There was one aspect that neither Ted nor Song could replicate. Southwest had developed a unique culture that was friendly, whimsical and borderline radical at times. Customers were attracted to this culture. Southwest passengers enjoyed corny songs sung by flight attendants and the overall attitude of the Southwest team. Ted and Song were simply offshoots of United and Delta and reflected their respective cultures. It’s true that there are other low-cost airlines that are profitable today, but they haven’t made serious inroads into Southwest’s market share or customer base.

What’s fascinating about all of this is how a Winning Culture can be so elusive. I’ve said many times that I’m not particularly concerned about sharing my playbook with my competitors. It’s not the design of the plays that necessarily wins the game. It’s how well those plays are executed that makes the difference. There are a multitude of sports metaphors in this respect. Think of all the professional football teams that are stocked with amazing athletes possessing world-class talent. And every single team has a playbook full of intricately designed plays for the offense and the defense. Yet, a dropped pass here and a missed block there can be the difference in whether a team wins the Super Bowl or watches it at home on TV.

What exactly is a Winning Culture? As entrepreneurs, it is something we may not think much about, but it can be the difference between success and failure. Far too often, entrepreneurs may not pay enough attention to creating and nurturing a Winning Culture, opting instead to focus more exclusively on operations and metrics. Southwest infuses the following into every employee it hires:

  • A warrior spirit
  • A servant’s heart
  • A fun-luving attitude (Southwest’s stock ticker symbol is LUV)

At Southwest, the warrior spirit is “being fearless in terms of delivering the product,” according to Ginger Hardage, the now-retired chief communications officer. The servant’s heart is based upon the Golden Rule and the need to treat everyone with respect. It’s pretty obvious what the “fun-luving attitude” is all about. Southwest looks to hire people who don’t take themselves too seriously and always have a smile on their face. There’s no question that Southwest pays a great deal of attention to operations and metrics, but its cultural foundation is rooted in these three values.

When a company stops winning and starts losing, the first place to look is to see if it has strayed from its Winning Culture. If the culture’s not right, the operations may be off kilter and the metrics will look bad. I believe that we must fix the culture first and then make the technical adjustments from there. And one more cogent point needs to be made. A Winning Culture is different than just plain culture. An organization may have a culture that has been intentionally cultivated, but doesn’t necessarily lead to winning. To win, we must be extraordinarily positive about it. Our entire team must be convinced that we are going to win and they must completely embrace the notion.

A Winning Culture is not replicable. It is unique to each company or organization and must be developed organically. It enables us to execute our playbook effectively in ways that our competition can’t.

You can also listen to a weekly audio podcast of my blog. What you hear will be different than what you read in this blog. Subscribe on iTunes or wherever you get your podcasts. You can also click on this link – Click here to listen to Audio Episode 31 – Balls in the Air.

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.

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