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Perseverance: Why It Was Southwest Airlines' Herb Kelleher's Most Important Lesson for Entrepreneurs

Sadly, Kelleher died last month. But his legacy lives on: Ever hear of how he and his airline became Texas's largest bourbon distributor?
Perseverance: Why It Was Southwest Airlines' Herb Kelleher's Most Important Lesson for Entrepreneurs
Image credit: Mike Fuentes | Getty Images
Guest Writer
CMO of Myia Health
6 min read
Opinions expressed by Entrepreneur contributors are their own.

I was actually on a Southwest Airlines flight when I found out that the company’s legendary co-founder and chairman, Herb Kelleher, had passed away. Kelleher died on Jan. 3, but over the five decades before that, his vision revolutionized air travel. His creation, Southwest -- arguably the world’s first low-cost airline -- democratized flying for millions.

Related: How Southwest Airlines Created a Mass Market for Air Travel

The company's differential was that by competing more with bus services than legacy airlines, it could disrupt the market. This strategy was so successful that in 1993, the U.S. Department of Transportation coined the term “The Southwest Effect” to denote an increase in origination air travel and a corresponding drop in prices, in any market the company entered.

This achievement alone is sufficient fodder for any successful entrepreneur's legacy. But the fact that Kelleher achieved all of that in a company that was, and still is, ranked as the best place to work in America, with employees who would go without pay to work there, says even more.

And there’s yet another lesson stemming from Kelleher’s and Southwest’s story: perseverance. Kelleher’s life offers a unique guide as to how entrepreneurs can and should persevere through even some of the most daunting obstacles they encounter and still come out on top.

What, exactly, does "perseverance" mean?

The importance of perseverance in entrepreneurship cannot be overstated. Starting a new business may initially seem exciting but often, after a short time, the shock of reality sets in. Product, customer and regulatory problems hamper business growth, and many entrepreneurs end up playing an inevitable game of “whack-a-mole” just to solve their problems.  

Perseverance is the ability of entrepreneurs to see through these obstacles and still win them, regardless of how daunting any specific challenge may be. Perseverance, in fact, is often the “secret sauce” that sets the most successful entrepreneurs apart from mere entrants in their field.

Stand for something more.

When Southwest Airlines was founded in 1967, the airline had no employees and no jets; it had to gain an operating certificate just to fly. Given the company's innovative business model, incumbents like Braniff and Texas International (both of which no longer exist) attempted to block Southwest’s operating certificate through a series of historic court challenges.

Related: Southwest Airlines: A Case Study in Employee Engagement

Though his airline was effectively grounded for  four years, Kelleher hung in there; his persistence ensured Southwest would, and did, eventually fly.

To accomplish this feat, Kelleher first offered his time as a practicing lawyer for free. More importantly, when Southwest’s board of directors wanted to abandon the fight three years in, Kelleher shouldered all court costs himself to get the job done. It would take two Texas Supreme Court rulings and one U.S. Supreme Court ruling before the airline could actually fly.

Before he passed away, Kelleher remembered that during that tough time, he was fighting for something more: the right of free enterprise and the ability to open the skies to consumers who couldn’t afford to fly.

Of course there have been other entrepreneurs with the same kind of tenacity, founders who have carried out some mission of their own with the same motivational force Kelleher showed. Patrick Grove, the founder of iFlix, is an example: He persevered through multiple roadblocks to democratize access to media and information in Southeast Asia.

In the process, Grove created Netflix’s biggest competitor in the video-streaming market. Belief in something more powerful than just a new business or the profits it may bring -- meaning a belief in the business's mission itself -- will motivate you, your employees, stakeholders and customers. By turning your business into a cause, you will be able to persevere through some of the darkest days as an entrepreneur.

Think differently.

Shortly after Southwest launched, Braniff thought that by launching a fare class at half of what Southwest was offering, it could undercut the airline and put it out of business. Other airline executives and the consumer press promptly wrote Southwest’s obituary.

But not Kelleher. He understood that to persevere through this crisis, the airline had to think differently. Examining revenue streams, he discovered that most passengers were business travelers on expense accounts who cared little for cost savings and more for time and convenience. So, he made a unique proposition: Pay the full fare and get a free bottle of Wild Turkey bourbon!

This promotion was so successful that over the course of just over six months, Southwest became the largest liquor distributor in Texas.

Stories abound of entrepreneurs thinking “around corners” and not giving up; This category includes people like the founders of Airbnb and GoodRX for example. The real lesson here is to look at the challenge and the situation before you and improvise until you win.

Like Kelleher, you should assess the real drivers of your business and the levers or incentives needed to change course in your direction -- not to just react to the imminent threat. Often, creative solutions will materialize because by looking at a problem differently, you will come up with a divergent solution.

Perseverance matters.

Kelleher sits among a long line of great, and often colorful, entrepreneurs who disrupted and revolutionized their respective fields. The one thread nearly all of these leaders have and had in common, and which Keller possessed in spades, was the ability to persevere through the most challenging of circumstances.

Related: Southwest's Heroic Crew Shows How a Strong Leader and Preparation Create Good Teamwork

Kelleher’s legacy not only shows us the power of “thinking around” the corners of a problem, it shows us the extraordinarily motivating power of believing in something -- a mission -- greater than oneself. That’s advice every entrepreneur should heed.

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