“She will be remembered as a truly remarkable woman, who had a profound effect on the course of events, both at home and abroad.. Throughout the last half of the 20th century, she used her intelligence, her courage, and her wit to transform the landscape of American journalism.” — New York Times
There is perhaps no female who made a greater impact on entrepreneurship and business in the 20th century than that of the late Katharine Graham. She served as the head of the Washington Post from 1963–1991. She took over a newspaper empire when it was generally thought that women weren’t fit for such roles of leadership and she proved what we now are more willing to admit: women run the world.
She led her company through one of the most tumultuous and difficult seasons any business will ever go through. She faced opposition from every side, from employees, board members, and even from the President of the United States of America.
She made billions of dollars. She led her company through a risky IPO in 1971 that over the remainder of the 20th century became one of the most successful public offerings of any business. She outpaced, outranked, and outperformed her competition in nearly every category over her years of leadership. As Ryan Holiday writes in his book Ego Is The Enemy, “If you’d invested $1 in the Post’s IPO in 1971, it would be worth $89 by the time Graham stepped down in 1993 — compared to $14 for her industry and $5 for the S&P 500.”
She was called reckless, crazy, dramatic, out-of-touch, and unprofessional. She succeeded anyway. She refused to play by the rules of a broken system and chose instead to let her moral compass and high business acumen guide her to continued progress and achievement. Her core beliefs defined her leadership and helped her not only reshape journalism but go on to reshape American History as well.
Her methods weren’t magic, but they were costly. In order to become one of if not the most influential female CEO of the 20th century, she had to take the hard path, letting go of her fears and doubts and choosing instead to stand solid and unshakeable on her beliefs.
These beliefs got her where she needed to go, just as they can help you lead and last in your entrepreneurial venture.
#1 — If you can endure, you can excel
“What did Graham need through all of this (hardship)? Not swagger. Not bluster. She needed to be strong. She needed confidence and a willingness to endure. A sense of right and wrong. Purpose. It wasn’t about her. It was about preserving her family’s legacy. Protecting the paper. Doing her job.” — Ryan Holiday, Ego Is The Enemy
If you go back and look at the history, it’s no secret that Katharine Graham was born well off. She was privileged. Her father was very financially savvy, accruing great wealth. In many ways, she grew up in luxury. Her story is not one you’d associate with the rags-to-riches narrative.
However, that doesn’t mean everything was easy or seamless. In 1963, Graham’s husband committed suicide, thrusting her into a leadership position at the Washington Post. The all-male conservative board didn’t recognize her authority, even after she became the first female Fortune 500 CEO in American History.
Throughout the 60s and early 70s, the newspaper was on the verge of collapse. Labor strikes from within and intimidation tactics from outside agencies threatened to sink the paper on countless occasions. At one point, the unhappy labor union “sabotaged company machinery, beat up an innocent staffer, and then set one of the printing presses on fire.” 
During her time as CEO, Katharine Graham became intimately familiar with adversity and hardship. But through it all she held on to this core belief:
If you can endure, you can excel.
Legendary football coach Bill Walsh once said, “almost always, your road to victory goes through a place called ‘failure’.” Katharine understood this more than most, and as a result, she stayed steady no matter what came her way.
#2 — Bet on yourself (with good guidance)
“Too often, dishonest or egotistical CEOs buy back company stock because they’re delusional…Conversely, timid or week CEOs wouldn’t even consider betting on themselves. In Graham’s case, she made a value judgment; with (Warren) Buffet’s help, she could see objectively that the market didn’t appreciate the true worth of the company’s assets.” — Ryan Holiday, Ego Is The Enemy
Betting on yourself is crucial for long-term entrepreneurial success. If you don’t believe in your venture, why should anyone else?
However, sometimes even the most well-intentioned entrepreneur can become blinded to the reality at hand. That’s why Katharine Graham understood that betting on yourself, while crucial, is often only as effective as the quality of the guidance that supports that wager.
We often romanticize the idea of the lone-wolf or the pull-yourself-up-by-your-bootstraps kind of entrepreneurship. But when it comes to good business, what is much more common, and much more effective, is the practice of betting on yourself in line with good advice.
Why is this so effective? Because it demonstrates the inner workings of the entrepreneur, highlighting two of the most essential ingredients to success and leadership: great courage and great humility.
For Katharine, she listened to the advice of a young Warren Buffett, who we all know has gone on to be one of the savviest investors of all-time. For you, if you want to be successful, you have to be willing to bet on yourself. But before you push all the chips in, ask yourself: who else are you listening to?
#3 —Proceed and publish
“Just as the company was filing to go public, the Post received a collection of stolen government documents the editors asked Graham if they could run, despite the court order preventing their publication. She consulted the company’s lawyers. She consulted the board. All advised against it… Torn, she decided to proceed and publish them – a decision with essentially no precedent.” — Ryan Holiday, Ego Is The Enemy
If you’re unfamiliar with the story, the stolen government documents referenced above would go on to become known as The Pentagon Papers. In 1971, The Washington Post partnered with the New York Times and decided to run one of the most explosive journalistic reports of the century concerning the war in Vietnam.
That decision was the catalyst for the even more controversial publishing of the Watergate Scandal in 1972, effectively aiding to end President Nixon’s time in office and re-shaping the American political horizon. Katharine Graham was able to lead through these various crisis points because she understood and fundamentally believed that:
Even when the going gets tough, proceed and publish.
She took considerable heat from many of the most powerful organizations in the country. From Congress. From the CIA and FBI. From the White House and the office of the President himself. But knowing endurance was part of the plan and understanding her value, she bet on herself and decided to publish anyways.
It was this boldness in the face of adversity that cemented her legacy and gave her the strength to lead her company as few business leaders have done before or since.
Influence is earned
Katharine Graham may have grown up accustomed to luxuries that you and I will never experience, but that doesn’t mean that we can’t aim to replicate her entrepreneurial success.
She may have been given a silver spoon to start, but she earned her metal over time, emerging from the crucible refined and remarkable.
Entrepreneurism can be daunting, but it doesn’t have to be dismal or destructive. You can succeed if you’re willing to endure, bet on yourself (with good advice), and proceed and publish. You’ll face failure along the way, but when that comes, know that you’re in good company.
Who knows? You might end up becoming the most influential CEO of the 21st century.
 Ego Is the Enemy — Ryan Holiday
This article first appeared on Medium.