Chapter 143 - King of the Cowboys: The Life and Times of Jerry Jones
Today’s Chapter is based on the book “King of the Cowboys: The Life and Times of Jerry Jones” by Jim Dent.
Jerry Jones is an American billionaire businessman and the owner, president, and general manager of the NFL’s Dallas Cowboys since 1989. Under his leadership, the team won three Super Bowls in the 1990s and became one of the most valuable sports franchises in the world.
Here’s what I learned:
Unyielding Work Ethic
“I never dreamt of success. I worked for it.”
— Estée Lauder
Jerry Jones’s journey from a small-town Arkansas kid to the owner of the Dallas Cowboys, one of the most valuable sports franchises in the world is a great example of the timeless value of a relentless work ethic. Shaped by his father’s lessons during the Great Depression, Jones understood that hard work isn’t just a means to an end but a core part of one’s identity. This mindset propelled him through early failures and into massive successes, showing that consistent effort can turn ordinary opportunities into extraordinary outcomes.
Jones explains that “It was that mentality from that era that drove him [his father]. When I was a kid, it was all he could talk about—the Depression. It scared the hell out of the people who grew up then, especially the ones on the farms. My dad passed that fear along to me. That’s why I always worked when I was a kid.“
As such, Jones first started working in his father’s business called Pat’s Supermarket, where he wasn’t just helping out but mastering every aspect of the business. Hard work wasn’t optional; it was ingrained. Jones mentions that “if I wasn’t down there working at the store every day, I was found guilty of something. I knew that my butt was going to be in trouble.” As a matter of fact, Jones’ father once told him, “I’m going to teach you to work so that you won’t mind working and it’ll be a part of your personality when you grow up.”
“I worked everything. I learned to do everything in the store. I was up at the crack of dawn, or I’d be working until midnight on something. My dad was a driver. But he was also a teacher. He just somehow knew where he was going.”
— Jerry Jones
This work ethic that Jones built through his father’s vigorous training at the family’s business paid off, not only in business but also on the football field. In fact, Jones was an undersized football player in college, but he led Arkansas to a national championship through sheer determination, not superior talent.
One of his head coach, Jimmy Albright, mentions that “Jerry didn’t have a lot of speed. In fact, he didn’t have a whole lot of anything as an athlete. But when he started something, he didn’t quit. Even at that early age, we were starting to see that work ethic that would carry him to his great success. It was already starting to show. This kid just worked his ass off night and day.” His story reminds us that in any field, whether business, sports, or personal growth, showing up every day with grit separates the achievers from the dreamers.
“Believe me, there were times when I failed. There were times when I was down on one knee, so to speak. But I was able to draw upon those times. One of the hardest things, I would learn, would be keeping my head together during those tough times. You just have to buck up and go on to the next decision. If you don’t move with enthusiasm to the next deal, you lose.”
— Jerry Jones
This reminds me of Chung Ju-Yung’s concept of “Do it until nothing more can be done. Give it your all ‘til the very end.” , which can be defined as his essence as a person and his fundamental principle of life. As Chung, the founder of Hyundai, once said, time is a form capital that should be used well. Chung explains that even for the most simple and most mundane tasks in life, it is important to put your best effort to achieve the best result possible.
“I realized that even simple tasks require practice. With the skills I acquired during those three nights, I soon became one of the best delivery boys in the city. Now, I was able to deliver two big bags of rice at a time. (…) My monthly pay increased to two bags and then to three. No matter how small the task, such as delivering rice on a bicycle, I pour all my energy into achieving the best possible result. Half measures, compromises, cutting corners, or “being realistic” do not exist in my world.”
— Chung Ju-Yung
This motto of his to “Do your best till there is nothing more to do” comes from his observation of bedbugs. In fact, he explains that “Even bedbugs think long and hard, and use every bit of energy they have to achieve their goal, and ultimately they succeed. I’m no bedbug, I’m a man. These bedbugs can surely teach a man a few lessons. If these bedbugs can do it, why can’t we men do it? We just need to stick to it and not quit. We need to emulate these bedbugs.”
Chung Ju-Yung believes that giving it your all and working diligently can make up for any shortfalls you may have. For example, while Chung Ju-Yung stopped his formal education after the sixth grade, he more than made up for it by reading books diligently. In fact, he once said that “if my first mentors were my parents, then my second mentors were books.”
“The story of my life demonstrates that one does not need great wealth and education to become successful. Even though I was poor and had little education, I am running one of the world’s most successful businesses. For those people who are in a difficult situation but continue to have big dreams, I hope my life can be an example that inspires them to push forward toward a better life through honest, hard work.”
— Chung Ju-Yung
Furthermore, Chung believes that one must work diligently every day in order to have steady improvement in life which can lead to success. In fact, he once said that “unless your life goal is wasting time, then the first thing I recommend is to be diligent. Being diligent forces you to move a lot, think a lot, and work a lot. Diligence mirrors your sincerity about living a full life. So I don’t trust anyone who is lazy. If you are diligent in attending to your daily needs, then over time you will become credible and reap the benefits of your diligence.”
“If you are diligent for a day, you will sleep comfortably for a night. If you are diligent for a month, the quality of your life will noticeably improve. If you are diligent for a year, two years, 10 years, your whole life... your accomplishments will be recognized by all. The diligent lead lives a 100 times more productive than the lazy. Their lives are thus more fulfilling. If you work 10 times more than a lazy person, then you are in fact shouldering the lives of hundreds.”
— Chung Ju-Yung
Embrace Risk
“No man is worth his salt who is not ready at all times to risk his well-being, to risk his body, to risk his life in a great cause.”
– Theodore Roosevelt
One of the most striking lessons from Jerry Jones is the power of calculated risk-taking, drawn from his experience in the oil industry. In fact, he treats business like wildcatting—drilling in unproven spots, defying conventions, and betting big on hunches. Jones operated on what Dent describes as an “oil patch mentality.” This philosophy, honed in the unpredictable world of oil wildcatting, is built on a simple premise: roll the dice aggressively, accept that some ventures will fail, and trust that the big wins will more than cover the losses. For Jones, safety and tradition are often the enemy of progress and profit. This approach turned dry holes into gushers in oil and transformed a losing NFL team into a powerful. It shows that playing it safe often leads to stagnation, while bold risks, when informed by instinct and preparation, can yield outsized rewards.
When Jones was into the oil business, he was an independent, searching for oil without any powerful financial support from companies like Shell or Exxon. As such, he “operated without a team of engineers and without their sophisticated computers and tracking devices.” But that did not bother Jones, he was always determined to succeed on his own terms and in his own way. Jim Dent mentions that Jones and his partner Bill Sparks’ plan “was to drill between the dry holes. It’s hardly surprising that other oil men thought they were crazy. In this case, though, Jones’s faith in Bill Sparks paid off. The group hit their first well, which was worth more than $4 million.” This first success led to more funding that would be used to drill more oil. As Bill Sparks once said, “Hitting that first one meant that we could go to the bank and borrow money and keep drilling. It meant everything in the world to us.”
“Some of your risks are bound to be busts. The more risks you take, the better the chance of one of them hitting.”
— Jerry Jones
This unorthodox way of drilling oils was similar to the way he ran his NFL team. He would defy all norms in order to succeed in his own terms, even if it meant firing two of the most popular and successful coaches in the history of the National Football League (Tom Landry and later Jimmy Johnson). Dent writes that “In the next century, NFL historians will review Jones’s blueprint for reconstructing the Cowboys and shake their heads. His plan was a total departure from all of the formulas NFL teams had tried in the past. Granted, teams had tried to improve themselves through trades throughout the seventy-odd years of the league’s history. But Jones and Johnson went at the trading process like kids in a candy store. The NFL had never seen anything like it.”
“I made the decision to run this football team without NFL football experience. I didn’t know that some of the things we would try couldn’t be done. No one sat down with me and told me, ‘There’s no way you can have this organization put together the way you want it if you don’t get some longtime NFL experience.’ I thought the way we were doing it was the only way we could do it.”
— Jerry Jones
To conclude, risk isn’t reckless for Jones; it’s about volume and recovery. He takes multiple shots, knowing some fail, but the wins compound. This mindset encourages us to challenge status quos in our careers or investments, calculating odds but acting decisively.
This reminds me of what we have learned from Donald Keough who served as president and COO of Coca-Cola. In his book, Keough offers profound insights into what makes a company thrive in a competitive landscape. One of the most critical lessons from his tenure is the necessity of embracing risk rather than shying away from it. Keough’s experiences highlight how stagnation can lead to downfall, and how calculated risks propelled Coca-Cola to global dominance.
As a matter of fact, Keough recognized that success often makes companies complacent, causing them to shy away from new challenges and innovations, a posture that inevitably leads to decline. He explains that “It’s reasonable to think that because when you achieve something, even very little, there is the great temptation to quit taking risks. It’s human nature. I’ve got something. Why risk it? Who knows what’s on the other side of the mountain? Don’t go there!”
In his book, Keough illustrates various examples of companies that succumbed to “the major diseases of success”: complacency, arrogance, and the paralysis that comes from avoiding risk. Notably, he talks about the story of Xerox who “had a least a five-year head start over its future rivals. But the box guys at headquarters failed to take a risk. That, as I said, is one of the major diseases of success. Two others are complacency and arrogance.“
“Over time, many, many successful companies have failed to take important risks at critical points, and they have paid a price. Some have merely stumbled and found later redemption, but quite a few have not only fallen but disappeared. In the 1980s alone, 230 companies disappeared from the Fortune 500. In fact, only 16 of the 100 largest companies that were around in the early 1900s are still with us. Who knows how many of the tombstones in the graveyard of capitalism should bear the epitaph “Here lies a company that died risk free.””
— Donald R. Keough
At Coca‑Cola, Keough cultivated the sense that success didn’t mean safety but instead required vigilance and a willingness to explore new things. He accepted mistakes and failures as part of the innovation process, arguing that the capacity to try, while knowing that many experiments will fail, is critical to long‑term vitality.
He points to creative environments like Apple’s where ambitious efforts produced both high‑profile missteps and transformative innovations; the failures were the price of continued relevance. In fact, he explains that “In business, you can make a good argument for mistakes like Steve Jobs’s Lisa or Power MacCube because the highly creative Apple environment that spawned them also produced big winners like iPod and iPhone. You can even justify those mistakes that have become the folkloric case studies in how-not-to-do-it courses in business schools all over the country, such as the Edsel or 45 rpm records or even New Coke. These failures, for all the valuable lessons that they teach us in hindsight about management blunders, are simply risks that just didn’t work out. Such miscalculations, costly though they might be at the time, are part of the price of staying in business.”
“In fact, if a company never has a failure, I submit that their management is probably not discontented enough to justify their salaries.”
— Donald R. Keough
Sports Management
“To me sports is a rental business and it’s an entertainment business.”
— Wayne Huizenga
Jerry Jones is, above all else, a businessman. While he loves football, his primary metric for success for the Dallas Cowboys is unequivocally financial. This singular focus on the bottom line has been the driving force behind his decisions as the owner of the team. He sees every asset, from players to a stadium seat, as a potential revenue stream, and, more importantly, he possesses a genius for unlocking value where others do not.
“From the first day he walked into the Cowboys complex, Jones has proven that he can sell, sell, sell. Of course, his selling skills and his deal-making abilities shouldn’t be surprising, given his background.”
— Jim Dent
When Jones purchased the Cowboys, the team was losing millions. He immediately set to transform it into a “lean, mean money machine”. His schemes were as innovative as they were bold. One of the first thing he did as the owner was to recall thousand of season tickets from former players and associates to resell them at a premium. In fact, Dent explains that “To obtain these tickets, the new purchasers also had to put money down for “seat options.” The options alone cost from $1,500 to $15,000 per seat, depending on their location, even though they don’t include the actual price of the tickets—they just give the option-holder the right to buy the tickets for that seat.“
Furthermore, he started to find innovative ways to add additional seats in the stadium in order to increase ticket revenues. In fact, while he was evaluating the stadium’s potential for generating revenue, Jones asked himself, “Where did the previous owners go wrong? Why did they lose so much money?”
His monetisation strategies seemed endless. He broke tradition by selling advertising signage inside Texas Stadium. He lobbied the city council to allow beer and wine sales, wining and dining officials to get his way. In fact, Dent explains that he set out to “convince the Irving City Council to grant the stadium a license to sell beer and wine. Like a good politician, Jones began wining and dining members of the council. He gave them free seats in the luxury suites. He brought some of them into the locker room after games. When the Cowboys reached the Super Bowl in 1993, five council members flew to Pasadena free on one of Jones’s chartered jets—and received free tickets to the game.“ He even moved the team’s training camp to save money and gain control over merchandise sales. Every decision was filtered through a lens of profitability.
“I’m not worried about the Super Bowl as I am about getting the damn luxury boxes sold.”
— Jerry Jones
His priority to focus on increasing revenues paid off spectacularly. Under Jones’ ownership, the Cowboys’ value skyrocketed from $60 million to over $200 million, and the franchise has became the most profitable in all of sports.
The lesson here is the power of an uncompromising focus on value creation. Jones teaches us to constantly question existing revenue models, to look for untapped opportunities, and to understand that sentimentality can be the enemy of solvency. For him, money is the scoreboard: “Money is how businessmen measure success. In a way, accumulating money is a way of keeping score.”
Beyond the Book
Read "Talent Is Persistence" by Farnam Street
Read "The Psychology of Risk and Reward" by Farnam Street
Watch "America's Team: The Gambler and His Cowboys" on Netflix
Read "Taking Risks" by Farnam Street
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