A lawyer by trade, Herb Kelleher famously started Southwest Airlines in 1968. Serving as their in-house counsel and later, CEO, Herb oversaw Southwest’s growth from a small Texas-based carrier to a national carrier that shook up the airline industry!
Remaining involved with the company from then until his death 51 years later, Herb received almost every major aviation and business-related accolade imaginable during his life – and even had a street named after him!
Early Life
Herbert David Kelleher was born on March 12 1931 in Camden, New Jersey. The youngest of four children born to Harry Kelleher, a soup factory general manager and his wife, Ruth, Herb grew up in an incredibly close-knit family.
Raised in nearby Audubon, New Jersey, Herbert Kelleher attended the local Haddon Heights High School, where he got the nickname “Herb”, where he excelled at subjects like English.
As was common at the time, Herb worked to help support the family, finding employment at the Campbell’s Soup Factory, where his farther worked, rising up the ranks from soup chef, to warehouse foreman, to being a part-time analyst.
Though a close-knit family, the Kellehers split up at the outbreak of WWII.
Too young to enlist himself, a young Herb watched his two older brothers and father enlist in the military and be sent off to fight, where his oldest brother and father would die in 1942 and 1943 respectively.
As for Herb’s sister, Ruth, she left home and travelled to New York, where she found work and lived for the rest of her life. Now the only child left at home, Herb formed a special connection with his mother, with the two sharing many of the same interests.
Beyond being the president of his junior class and captain of the football team, Herb found work as a branch manager for his local newspaper, the Philadelphia Bulletin, and mowed several of his neighbors’ lawns.
Graduating high school, Herb enrolled at Wesleyan University as a Olin Scholar, majoring in English and minoring in Philosophy, where he earned a bachelor’s degree.
Attending the New York University School of Law as a Root-Tilden Scholar, Herb earned his Juris Doctor and graduated cum laude in 1956.
Legal Career
Now having a law degree, Herb began studying for the bar so he could be become a lawyer. Passing the bar exam in 1957, Herb Kelleher was officially admitted to the New Jersey bar and began seeking out employment.
Finding work as a law clerk to a New Jersey Supreme Court Justice, Herb worked there for two years before accepting a job at Newark, New Jersey-based law firm Lum, Biunno and Tompkins.
As an associate there, Herb earned enough money to regularly travel down to Texas to see his wife’s family who came from there.
Slowly falling in love with his wife’s home state, Herb Kelleher made the decision to move to San Antonio, Texas in 1961, with the intention of not only starting a new life there, but also a law firm or some other kind of business.
However, there was only one problem: he didn’t have the money to start his own law firm/business. So he endeavored to get it, by joining local law firm Matthews, Nowlin, Macfarlane & Barrett, as a partner.
It was through Matthews, Nowlin, Macfarlane & Barrett, that Herb Kelleher met local businessman Rollin King, becoming his attorney. Working together on several occasions, Herb revealed his desire to start his own business to King.
Air Southwest Co.
Later Life
Having been with Southwest since the beginning, and led the company for the better part of 20 years, a now 70 year old Herb Kelleher began thinking about passing on the torch.
Announcing it months before, Herb Kelleher officially stepped down as both President and CEO of Southwest Airlines in March 2001, being replaced by Colleen Barrett and James Parker as President and CEO respectively.
Despite his advancing age, Herb remained as the airline’s chairman for the next seven years, officially retiring from as chairman and resigning from the board of directors in May 2008.
Though many though it would be, this was not the end of Herb’s involvement with the company he founded. Given the title of Chairman Emeritus by his replacement, Gary C. Kelly, Herb maintained an office at Southwest’s Dallas HQ for the rest of his life.
Enjoying his retirement, Herb appeared at the company intermittently, usually appearing to help advise the Southwest board on how to proceed with a certain business move, or help them to fix an issue.
Beyond remaining involved with the company he helped found, Herb Kelleher was also appointed to chair the Federal Reserve Bank of Dallas’s board of directors in July 2010. Officially taking the position in 2011, Herb served until 2013, when his term was over.
Often quoted as saying he was “flunking” retirement as he maintained an office at his company’s HQ and served in an advisory role to several government agencies and non-profits, Herb relished the time he got with his family.
Death
Despite being larger than life in almost every regard, Herb was not immortal. On January 3 2019, Herbert David Kelleher, better known to the world as Herb Kelleher, passed away surrounded by his family.
He was survived by his wife, Joan Negley, who he’d been married to for the better part of six decades (64 years to be precise), three of their four children and their nine grandchildren, who affectionately called him “Poppair”.
Per Herb’s wishes, his death was announced by Southwest on all their flights and their social media. Obituaries were published in almost every major newspaper in the US, especially in and around Dallas, and his death was reported by several major news outlets.
His funeral took place in Dallas on January 9 2019, six days after his passing, and Southwest paid tribute to their founder through a series of memorials, many of which were attended by celebrities and business leaders alike.
At the time of his death, Forbes estimated Herb Kelleher’s net worth to be somewhere in the region of $2.5 billion. Adjusted for inflation, Herb’s net worth would be $2.67 billion.
Legacy
How Can I Replicate What Herb Kelleher Did?
Reading about the incredible life of Herb Kelleher, chances are that you’re trying to figure out how to replicate what he did, and similarly become the head of a large airline (and maybe even a billionaire like Herb!)
Usually, this is the part where I explain that whilst you could use what I wrote above as a “how to” guide and similar
What Can we Learn From Herb Kelleher?
Though he may have founded his airline over 50 years ago, the life of Herb Kelleher can still teach you quite a bit, not just about starting/running your own business but also about life in general!
Your Employees Come First
All too often, businessmen and entrepreneurs alike are so customer-focused, that they often lose sight of what makes their company great: its people.
Whilst many of them will say things like “our people are what make us so good at X”, they often don’t appear to mean it, often sacrificing employee morale for the bottom line. Yet, Herb didn’t do that, he genuinely cared for his employees.
To Herb, there was nothing more important than Southwest employee functions. As the founder, and later chairman and CEO of the airline, Herb was almost always a keynote speaker or had at least promised to attend.
And nothing (and I mean nothing) would stop him from going. A multibillion dollar business deal? Not a chance. The SEC? We’ll have to reschedule. A competitor? Sorry, my employees are more important.
But when he went to these events, he didn’t just make a speech with a few cheesy jokes in them and call it a day. He was the first one to arrive and the last to leave, and tried to meet as many of his employees as possible.
No matter what, he would learn your name and never forget it.
A few years before his death, Herb was quoted with saying:
Your employees come first. And if you treat your employees right, guess what? Your customers come back, and that makes your shareholders happy. Start with employees and the rest follows from that.
And he meant it!
Set Reasonable Targets
Beyond endeavoring to attend every Southwest employee function and learn the names of every employee he met, Herb also ensured that his employees didn’t feel pressured by pencil-pushers back at corporate to deliver miracles.
From the get-go, Herb always set his employees relatively low targets compared to what employees at Southwest’s competitors would get.
For example, a pilot at Southwest would have a target of say, 20 smooth landings in a month, whilst one at United, or Delta, or American, would get a target of, say 25, even though they fly fewer times per month.
But this wasn’t just because Herb didn’t know how to set proper targets for his employees, but rather the opposite. He knew that if he pressured his employees, many of whom are relatively new to the job, with high targets, they’d buckle and miss their targets.
Without that pressure, they were able to easily meet, and ultimately surpass, their targets, which Herb Kelleher and Southwest as a whole expected them to do!
Interestingly, though Herb Kelleher is no longer a part of the company, and the industry has changed quite a bit since he left, Southwest still sets lower targets for its employees than United, Delta and American do for their employees.
Don’t Take Yourself Too Seriously
All too often, we as entrepreneurs spend so much time trying to innovate and disrupt our industry that we can sometimes come across as, perhaps a bit bland. Or at least, rather serious (all the time).
Indeed, whilst there are certain moments where you do need to take yourself seriously, such as launching a takeover, or trying to raise finance for your endeavor, it’s unnecessary most of the rest of the time.
Though Herb could’ve been like every other CEO and been 100% serious, 100% of the time, he chose to be a little more light-hearted about everything. And there are literally hundreds of stories going back decades documenting this.
Diagnosed with prostate cancer in 1999, Herb underwent several months of radiotherapy to rid himself of the disease, but not before he could have some fun.
A lifelong smoker, Herb thought it would be funny to arrive to his radiotherapy appointment puffing away on a cigarette. When the doctors told him to put it out, he told them that “If you want a smoker to put out cigarettes, you ought to have ashtrays.”
He then proceeded to make sure that they knew it was a joke by asking “You want me to put it out on the floor?” and motioning his cigarette to the floor. Realizing he was making a joke, the doctors reportedly told him to “Get out of here!”
And this isn’t an isolated incident, there are many more of him using Southwest employee events to make sure his employees know he didn’t take himself too seriously, usually involving a cigarette or alcohol… or both.
Be Humble
From how they’re portrayed in movies and TV shows, you’d expect a billionaire businessman like Herb Kelleher to be one of the most arrogant people on the planet. After all, he’s a part of the so-called “three comma club” and you are not.
Yet, Herb was nothing like that. In fact, it was the complete opposite according to pretty much everyone who met him.
Though Herb did have a company-provided Learjet for all Southwest-related travel, which he flew on occasion, Herb was famous for flying on one of his airline’s aircraft on a regular flight.
He wouldn’t even warn the crew in advance. He’d just turn up to the airport, board the flight and depart at the end. But he didn’t do this because he wanted special treatment, but rather the opposite: he did it to blend in.
Indeed, there are several instances of times when Herb did an entire transcontinental flight onboard one of his aircraft with no one the wiser.
It was only after they landed that he’d approach the crew, tell them what a great job they did, and introduce himself, much to the crew’s embarrassment!
Another example of his humility was his insistence on having an office without windows. Despite Southwest’s Dallas HQ having hundreds of offices with great views that employees would kill to have, Herb didn’t want them.
He knew that for him, an office with a view was irrelevant, and even a little distracting, so he had an office without a view. That office with a great view that would’ve been his, instead went to one of the employees he cared so dearly about.
Has the story of Herb Kelleher inspired you? Tell me in the comments!
