The Successful Stoic: Ryan Holiday

A profile on the NYT bestselling author — from manipulating the media — to fighting their nihilism.

Tom Chanter
Oct 15 · 35 min read
Photo by Luiz Berengue [CC BY-SA 2.0]

The duality of Ryan Holiday is a riddle. But what stands in the way becomes the way. So let us ask…

Why do authors like John Grisham and behemoths like Google hire him? What drives the military to invite him to speak to their elite Special Operations fighters? And who are the people behind “the kid going places”?

Exploring Ryan Holiday’s story sees us meet refugees and prisoners. We will court beers and babes. President Trump will tempt us. We will meet “the girl”. There is Pride. There is Humility. And there is a letter from a stoic and a letter to his father.

As big things have small beginnings, behind the prodigy is the person.

Never having felt “seen” by his parents, when Ryan Holiday discovers his talent for manipulating media sites like Jezebel and Gawker, he drops out of college, is appointed Director of Marketing for American Apparel, and writes Trust Me, I’m Lying. It becomes a NYT bestseller.

But when the stoic philosophy of Marcus Aurelius and Seneca force him to confront the poison that is ego, Ryan Holiday must learn to integrate being both a creative individual and a professional son. He must learn to integrate his media power with his writing responsibility — before the Gawker media empire irreversibly corrupts the Fourth Amendment of the U.S. Constitution.

PART I: Pride

“Humility is not disgraceful, and carries no loss of true pride.” — Ernest Hemingway

Who Is Francisco d’Anconia?

Photo by Elijah O’Donnell on Unsplash

Ryan Holiday wrote in the New York Observer, “I heard scratching at the door. It’s usually the dog asking to go outside. But this was my goat, and she wanted to come inside.”

“No, Bucket,” I told her. “We can’t let livestock in the house.”

He continued, “Back in New York for meetings this week, I got a motion alert from my Dropcam, which monitors my living room and inside doorway. Usually the update is wind related, so I certainly wasn’t expecting to see the goat, the dog and Samantha all playing on the floor together. I guess that explains why Bucket always seems to expect me to open the door and let her in.”

Samantha continued letting their goat in the house, despite Ryan Holiday’s repeated objections. Yet he would later write, “This is, after all, what makes her special and attracts me to her, that she is so inexplicably different. That she defies and baffles the order, logic and seriousness with which I tend to treat the world.”

Ryan Holiday talked about his relationship with his parents on the You Made It Weird podcast, “I want to be seen, but I also want to be gotten. I want you to get me. So it takes me back to this 11, 12-year-old where my parents are like, Who is this kid living in our house? We know he’s our son, but what’s his deal?

At 19, he was reading Meditations by Marcus Aurelius. At 20, he would find himself writing, “My parents had disowned me, I needed to move to a new city, the girl whose job I stole hated me.”


“My parents were not big fans of me dropping out of college, but Samantha pushed me to do it, knowing it would be best for my career,” Mr. Holiday said.

Holiday’s first opportunity came from the NYT bestselling author Tucker Max. With ‘beer and babes’ books like Assholes Finish First and I Hope They Serve Beer In Hell, critics were joining the hoards of adoring young men and women obsessing over the perennial bad-boy Tucker Max. Ryan Holiday’s role was helping him manipulate the media.

Once he encouraged Tucker Max to donate $500k for Planned Parenthood to name a clinic after him. While Planned Parenthood aborted the donation, it birthed free PR.

Another time he ignited an actual protest movement against Tucker Max’s ‘sexism’ by anonymously sending bloggers photos of a vandalized movie poster of I Hope They Serve Beer In Hell. (Spoiler: Holiday was the vandal.)

Yet Holiday was not there for the beer (he doesn’t drink) or babes (he had a girlfriend). Where the moral crusaders saw voyeurism, he saw art. Tucker Max was following in the steps of the immortal Gonzo writer Hunter S. Thompson.

As Holiday put it, The Good Doctor wrote of, “Man’s descent into primal behavior as an escape from both internal pain and the crushing pressure of a mundane external world.” While one generation in pain followed Hunter S. Thompson to Las Vegas, another followed Tucker Max to Hell. Ryan sold the ticket, Tucker took the ride.

Tucker took the ride, but as Holiday later told The New York Times, “I was the kid who was going places.” As Tucker Max was being courted by college girls, Ryan Holiday was being courted by established authors. Holiday began working for Robert Greene.

If Tucker Max’s art echoes that of Hunter S. Thompson, then Robert Greene’s echoes’ that of the writer and political theorist Niccolò Machiavelli. One of Greene’s most infamous books, 33 Strategies Of War, is a bible of the C-suite and has been banned in prisons.

Yet Robert Greene is not ‘Machiavellian’ like sociopathic CEOs and criminals. Niccolò Machiavelli wrote about politics and power with the fervent detachment of an anthropologist. So too, Robert Greene. Greene’s books, The 48 Laws Of Power, The Art Of Seduction, Mastery, and The Laws Of Human Nature, expose the secrets of the rich and powerful. They reveal how human nature really works.

Soon Holiday became more than a researcher. More than a media-strategist. Ryan Holiday was more than working for Robert Greene. He became his apprentice in the truest sense of the word: a master craftsman passing down his attitude, his processes and his secrets to a protege.

One lesson was how to write books that last so long; “It starts by wanting to create a classic.” While the book would have to wait, the lessons were about to begin. Holiday went to work at American Apparel.

At the time, they were one of the largest apparel companies in North America. Ryan Holiday was appointed Director of Marketing. He reported to CEO and founder Dov Charney.

Like many CEOs, Charney applied the teachings of Robert Greene’s book The 48 Laws Of Power. Yet unlike most CEOs, Charney also employed the lessons of The Art of Seduction.

Along with routine Director of Marketing tasks like buying ad space, Holiday was engineering unpaid publicity. He published risque ads that were sure to be banned (and blogged about). He leaked fake Halloween outfit ideas to the gossip-blogs Gawker and Jezebel (to avoid copyright claims). He even had the famous mattress-actress Sasha Grey pose provocatively for a campaign.

American Apparel was famous for the seductive photos they used in their marketing. Many of those photos were taken by the CEO himself, Dov Charney. In fact, part of the reason they looked so seductive, is because Charney was seducing the models.

In the end, Dov Charney was fired for misconduct, including sexual harassment. Dov Charney fell to a baser pleasure. Yet Ryan Holiday would rise to a higher purpose — inspired by Upton Sinclair,.

Upton Sinclair became a Pulitzer Prize winning writer in 1943. But his book that influenced Holiday was published in 1919. It’s titled Brass Check. ‘Brass check’ refers to money given somewhat secretly to a journalist for services rendered. The book exposed the pay-for-play corruption of the media system in the early 1900s.

Sinclair called it “the most important and most dangerous book I have ever written.” Indeed, it was so damning of the fourth estate that even the New York Times refused to run advertisements for the book.

As Holiday wrote, “Sinclair deeply understood the economic incentives of early 20th century journalism and thus could predict and analyze the manipulative effect it had on The Truth. I used that book as a model for my expose of the media system, Trust Me, I’m Lying.

Ryan Holiday used his experiences manipulating the media to write a modern expose of today’s corrupt media system. “I was disgusted with how it all worked,” he said. “The idea of the book was, I’m going to put all these things in a giant pile and light them on fire.” “I’m pulling back the curtain because it’s time the public understands how things really work. What you choose to do with this information is up to you.”

First-time author Ryan Holiday received a $250,000 advance for the book. Somehow the gossip-blogs reported that figure as $500,000.

To Be Or To Do?

Photo by Chandler Cruttenden on Unsplash

In the spirit of Upton Sinclair and Hunter Thompson, Trust Me, I’m Lying was a gonzo exposé.

“The true voice of Thompson is revealed to be that of American moralist… one who often makes himself ugly to expose the ugliness he sees around him,” wrote novelist and journalist Hari Kunzru. The New York Times didn’t hesitate to point out when one reader called Holiday a “Scumbag.” Mission accomplished.

It was time for a new mission. In Robert Greene’s The 48 Laws Of Power he writes, “Do not accept the roles that society foists on you. … Be the master of your own image rather than letting others define it for you.” That’s Law 25: Re-create yourself.

Ryan Holiday was re-creating his image from a media manipulator to a growth hacker. In 2013, Holiday released his second book Growth Hacker Marketing. It explains how companies like Snapchat, Dropbox and Airbnb are trading traditional marketing tactics for testable, trackable, and scalable tools.

Still, for someone who saw the art in ‘beer and babes’ stories, and for someone who not only read history’s forgotten Upton Sinclair but followed in his footsteps, a transformation from media-manipulator to growth hacker probably didn’t go far enough. But what stands in the way becomes the way.

Like Upton Sinclair, Colonel John Boyd is a man who history has largely forgotten. Yet he is the greatest military strategist, theorist and innovator since Sun Tzu. He gave a speech that Ryan Holiday has referred to…

“You’re going to have to make a decision about which direction you want to go.” He raised his hand and pointed. “If you go that way you can be somebody. You will have to make compromises and you will have to turn your back on your friends. But you will be a member of the club and you will get promoted and you will get good assignments.” Then Boyd raised his other hand and pointed another direction. “Or you can go that way and you can do something — something for your country and for your Air Force and for yourself. If you decide you want to do something, you may not get promoted and you may not get the good assignments and you certainly will not be a favorite of your superiors. But you won’t have to compromise yourself. You will be true to your friends and to yourself. And your work might make a difference. To be somebody or to do something. In life there is often a roll call. That’s when you will have to make a decision. To be or to do? Which way will you go?”

PART II: Breaking Vs Breaking Through

“The world breaks everyone and afterward many are strong at the broken places. But those that will not break it kills.” — Ernest Hemingway

Letters From A Stoic

Photo by Jack Sloop on Unsplash

“I was 27 at the time. There’s not a lot of 27-year-olds in Workaholics Anonymous,” said Holiday.

“I’d come home and I had written all these emails on the plane and I was waiting to get to my house so they would all send when I got WiFi. I got home and the internet was down. … It wasn’t working and I was freaking out. I had a legitimate panic attack that I couldn’t send these totally meaningless emails at 11:00 p.m. on a Friday. This is deadly serious to me.”

“I’m behaving like an obscene monster, basically.”

“I’ve told myself that my job is to manage this crisis that I didn’t create; that it’s impossible for me to actually solve; to make other people lots of money. Is this what I was put on this earth to do? To be a bundle of stress and angry nerves? Of course not.”

Beyond reassessing his work addiction, Ryan Holiday moved from an apartment in Los Angeles to New York, and ultimately to a ranch in Austin, Texas.

Many wouldn’t have expected this emerging media-mogul to move to a Texan ranch. Yet it was even more surprising to see him at Stoicon.

As the New York Times reported, “Stoicon, [is] an annual conference for academics and practitioners of Stoicism, the ancient Greek and Roman philosophy that counsels self-effacement and detachment from the vicissitudes of success and failure.”

What was Holiday doing there? Remember, this guy is the same guy who faked vandalism to help sell a movie called I Hope They Serve Beer In Hell. But Holiday wasn’t just attending, he was presenting.

“I will start with the question many of you are probably asking, which is, ‘Who the hell is this guy?’” said Holiday, as reported by the New York Times. “Some of them looked at Ryan as a keynote speaker and said, ‘Wait a minute, that’s not Stoicism,’” said Massimo Pigliucci, a philosophy professor at the City College of New York.

The NYT noted, “During a question-and-answer session, one audience member faulted Mr. Holiday for holding up flawed historical figures like John D. Rockefeller, a rapacious capitalist, as a model of Stoicism. Another questioned whether Mr. Holiday’s pursuit of success as a marketer and author was consistent with the Stoic emphasis on detachment from material gain.”

Indeed, shouldn’t the practitioners step aside for the academics when it’s time to speak on virtue? Nassim Taleb knows better.

While Nassim Taleb now publishes academic papers on risk and writes bestselling books, he was a trader first. He learned and earned his lessons losing and making money in the financial markets. Here’s what Taleb wrote;

“For studying courage in textbooks doesn’t make you any more courageous than eating cow meat makes you bovine. By some mysterious mental mechanism, people fail to realize that the principal thing you can learn from a professor is how to be a professor — and the chief thing you can learn from, say, a life coach or inspirational speaker is how to become a life coach or inspirational speaker. So remember that the heroes of history were not classicists and library rats, those people who live vicariously in their texts. They were people of deeds and had to be endowed with the spirit of risk taking.”

Indeed, it’s the men of action that make the best philosophers.

In fact, stoicism was founded by men of action. Stoicism’s three most influential books are Meditations by Marcus Aurelius, Discourses by Epictetus and Letters From A Stoic by Seneca. All three were men of action before they were men of philosophy. Marcus Aurelius was emperor. Epictetus was a slave. Seneca was Rome’s most successful businessmen.

They learnt how to live, not from textbooks, but from life. The best philosophers aren’t the men in the bleachers, they’re the men with skin in the game. They’re getting mud in their eyes, fear in their hearts, and at times, blood on their hands.

Ryan Holiday isn’t the perfect person. But he may be the perfect person to translate the ancient philosophy of stoicism to a new generation. Not only does he read stoicism with a fervor young men usually reserve for chasing girls, he’s a man of action. His tribulations and triumphs seared the stoic philosophy into his marrow, in a way that reading books cannot.

That’s why his next book was championed by Olympians, Silicon Valley entrepreneurs, NFL coaches and special forces operatives. He had learnt and shared the first key lesson. As Marcus Aurelius put it, “The impediment to action advances action. What stands in the way becomes the way.” As Ryan Holiday put it, The Obstacle Is The Way.

Letter To His Father

Photo by William Isted on Unsplash

In a piece titled; Dear Dad, Please Don’t Vote For Donald Trump, Ryan Holiday wrote,

“When I was in Austria a few years ago, I called Mom and had her do some research to find the location of the refugee camp that Grandpa was sent to when he was just a little younger than I am now. It’s an apartment complex now, which I guess goes to show how quickly we can forget the kind of thinking that creates such horrors.”

He shared many personal stories in that piece written to his father, including this one; “I told you that a few weeks ago we had someone out at the house to repair some damage from the floods. As I was walking the property with the guy, he asked me if I owned a gun. I said that I did — this is Texas after all. ‘Good,’ he said, ‘You’ll need to have something when them sand niggers come and try to take this country from us.’”

Obviously, racism is repulsive. Especially that particular xenophobic repair man. Yet today, many city slickers feel a similar repulsion to all gun-owners. But not in Texas.

As the New York Times reported, “Their modest two-story house has a walk-in gun closet, where Mr. [Ryan] Holiday stows a .22 hunting rifle, a 12-gauge shotgun, and a bow and arrow. He keeps a .243 next to the bed, to chase off coyotes and foxes. He shot a jack rabbit from his front porch, and skinned and ate it, and has taken up hog hunting.”

While racists with guns are repulsive, guardians with guns are redemptive. Holiday wrote to his father, “As a police officer, you worked for a time in the hate crimes division. You’ve seen the horrible things that prejudice and ignorance can do. I remember you once told me that the way the Ku Klux Klan recruited people in our hometown was by convincing white people that they were being attacked and that their way of life was under siege.”

Our family teaches us important lessons, even when we don’t hear them right away. Ryan wrote more of his Grandpa. “Before he died, Grandad gave me his copy of John McCain’s memoir Faith of My Fathers and said that I might like to read it. It wasn’t until years later that I got around to it. Did you know that when John McCain was trapped in that horrible North Vietnamese prison, his captors offered to let him go several times? McCain’s father was the commander of all US forces in the Vietnam theater and the Vietcong thought by giving his son an easy way out, they could show that Americans were cowards. Despite the repeated torture that he’d already undergone, despite the fact that McCain ached to go home, he refused. He stayed because he refused to embarrass his country or abandon his comrades — death was better than dishonor. I think that’s the kind of lesson that Grandad was trying to pass along to me.”

“And yet here we are discussing a Republican candidate who insulted John McCain in front of the entire world — claiming that John McCain isn’t a hero because he was captured and spent time in a POW camp.”

You can read Ryan Holiday’s full letter to his father here. But there are a few lines towards the end that capture its spirit; “That’s not what you taught me. That’s not how this country is supposed to work. Mom and half our relatives wouldn’t be here if it was.”

While Donald Trump is a Christian, Ryan Holiday is a stoic. Jesus and Seneca were born in the same year. The year zero.

“In A.D. 49, the well-known writer and Stoic philosopher [Seneca] was recalled from exile to tutor the successor of the emperor Claudius, a promising teenager named Nero,” wrote Holiday.

“Though Nero had good qualities, he was obsessed with fame and had an endless need for validation. He was also unstable and paranoid, and began to eliminate his rivals — including murdering his own mother.”

By 65 A.D., Seneca had finally seen enough. When conspirators began plotting against Nero’s life, Seneca joined them. Or at the least, he covered for them.

When Nero discovered Seneca’s betrayal, he returned it in kind. As Holiday wrote, “His [Seneca’s] life up to that point had contradicted many of his own teachings, but now when Nero’s guards came and demanded his life, he would be brave and wise. The man who had written much about learning how to die and facing the end without fear would comfort his friends, finish an essay he was writing and distribute some finished pieces for safekeeping. Then, he slit his veins, took hemlock and succumbed to the suffocating steam of a bath.”

We don’t get to choose how or when we die, but we can always choose death before dishonour.

“My own early career involved some questionable service to business people. Employed and paid by them, I planned and carried out controversial publicity stunts, and used dishonest tactics with the public and the media. When I finally left those roles, I found a knowledge of Stoic philosophy integral to my ability to assess my past actions, and set a more honorable course going forward,” Holiday later wrote in the New York Times.

But what is the honourable course? “You can’t learn if you think you already know,” writes Holiday. As a child we know our father has all the answers. Half of the USA believe Donald Trump has the answers to their problems. These are illusions. The death of Seneca reminds us nobody has all the answers. This is the essence of Socrates wisdom; “I know that I know nothing.”

Like Seneca, Socrates was ordered to die. When the time came, he drank his poison, walked until his legs felt numb, lay down, and waited for the poison to touch his heart.

It was Socrates, too, who said, “All of philosophy is training for death.” But we don’t need to wait for a poison to touch our heart. We die only once, but we live ten thousand times each day. We can use their honourable deaths as training for our lives. This is why we remember the death of Seneca; not so we know how to die, but so we know how to live.

“What are you going to do with this pain or suffering or difficulty? Is it going to make you closer with your brother? Is it going to make you a better father?” said Holiday.

There is no honour without suffering. John McCain suffered torture and incapacitation so as not to dishonour his country. Ryan Holiday’s Grandpa suffered the indignity of a refugee camp so he could survive and give his family a future.

We all have the opportunity to live honourably each day. We can all choose stoicism before epicurism. But too often pride is the obstacle in our way.

Ego is a poison spreading through our bodies. When we cannot control our own ego, it is useless to try controlling ego-maniacs. We cannot stand up to the tyrannical father when we are in our own way. We cannot stand against the chaos of life until we have put our own ego in order. We must take an antidote before it reaches our heart.

Ryan Holiday’s fourth book is titled Ego Is The Enemy. It shows how ego death gives birth to an honourable life. His book is an antidote to our ego.

Remember Holiday talking on the You Made It Weird podcast? “I want to be seen, but I also want to be gotten. I want you to get me. So it takes me back to this 11, 12-year-old where my parents are like, “Who is this kid living in our house?” “We know he’s our son, but what’s his deal?”

He continued, “I wasn’t a black sheep because I wasn’t getting in trouble. But it was like this kid is not meshing with everyone else in the family. … I have one younger sister and she’s great. But there’s the concept of parent-child fit and she fits with them perfectly. They are much closer. … I probably became a writer because I was like, “You guys don’t get it. I’m going to go in my room and I’m going to type this out. And then everyone will understand.”

Early in his career, Holiday succumbed to money and fame. Sometimes it’s easier to descend into primal behavior rather than facing our internal pain. But what stands in the way becomes the way.

“The professional son understands what every father wants — a progeny worth his time, someone to invest in, someone who can further his legacy. The professional father wants to see his greatness given a second body — a younger one, with more energy, with the benefit of his hard-won experiences,” wrote Holiday.

“I started as this research assistant for this author named Robert Greene and he’s been like a surrogate father to me and he taught me how to be a writer. And he really did see me.”

Robert Greene the master, helped his apprentice, Ryan Holiday, become a bestselling author. Holiday was more than seen. He achieved some fame. Or at the least, notoriety. Still, he hadn’t written it for the fame. He’d written in the spirit of the Gonzo’s, and even moreso, in the spirit of Upton Sinclair.

Yet, “Sinclair’s The Brass Check, has been almost entirely forgotten by history,” Holiday wrote. Similarly, while Holiday’s own book was a success, the media-manipulation, pay-for-play, and fake news continued. He’d exposed an ugly culture, but it was still ugly. He had critiqued culture, but hadn’t changed it. He was seen, but what had he done? What will he do?

We return to Colonel John Boyd’s call; “To be, or to do?” This is a question that has echoed through the ages. As Shakespeare wrote, “To be, or not to be?” It’s a call we all must answer, one way or another. It’s a call that comes from the depths of our soul. Or perhaps, our psyche.

Erich Neumann was a PhD, psychologist, philosopher, and student of Carl Jung. He wrote the perennial tome, The Origins and History of Consciousness. He states;

“In normal times, when culture is stable and the paternal canon remains in force for generations, the father-son relationship consists in handing down these values to the son and impressing upon him, after he has passed the tests of initiation in puberty. Such times, and the psychology that goes with them, are distinguished by the fact that there is no father-son problem, or only by the suggestion of one. We must not be deceived by the different experience of our own “extraordinary” age. The monotonous sameness of fathers and sons is the rule in a stable culture. The sameness only means that the paternal canon of rites and institutions which make the youth an adult and the father an elder holds undisputed sway, so that the young man undergoes his prescribed transition to adulthood just as naturally as the father undergoes his to old age.”

Neumann continues,

“There is, however, one exception to this, and the exception is the creative individual — the hero. As Barlach says, the hero has to “awaken the sleeping images of the future which can and must come forth from the night, in order to give the world a new and better face.” This necessarily makes him a breaker of the old law. He is the enemy of the old ruling system, of the old cultural values and the existing court of consciousness, and so he necessarily comes into conflict with the fathers and their spokesman, the personal father.”

So when should we follow our fathers and when should we forge our own path? Is Ryan Holiday destined to be a son or a hero? Or both? How could a boy know?

One Person Is Really Two

Photo by Jeremy Bishop on Unsplash

“I met a girl. Or rather, I met the girl,” Holiday wrote.

As the New York Times reported, “Ms. Hoover and Mr. Holiday met at a mutual friend’s party in January 2007 in Riverside, Calif., where they were 19-year-old sophomores at the University of California. “She was sitting in a large cardboard box, just messing around,” Mr. Holiday said, laughing. They began chatting. “I immediately saw her as this amazingly unique, beautiful and free-spirited woman.”

“Deciding to ask Sam to marry me was a process many years in the making, one that, honestly, I didn’t totally understand but knew was time for me to get on with. I found what I thought was the perfect ring while in New York on business: a 115-year-old Victorian piece that I put a better diamond in,” wrote Holiday. “I put that little ring in that little safe and forgot about it.”

“Samantha took a phone call: Your house has been broken into. Everything was stolen. Everything ransacked and destroyed. That safe? Yeah it was broken into as well–busted completely open and cleaned out,” wrote Holiday.

Before we see what happened with their relationship, let’s take a step back. Remember Tucker Max? He no longer writes about beers and babes. He has moved to Austin and lives with his wife and two kids. And Dov Charney? He’s single. But he has started another fashion company; Los Angeles Apparel.

As Holiday has noted, “We’re supposed to believe that relationships tie people down, that they are the death knell for creativity and ambition.” Despite settling down with his family, Tucker Max has written and sold numerous TV shows and screenplays along with co-founding a new company.

Most ambitious people struggle to achieve in a lifetime what Holiday has in a decade. Why? The duality of attack and surrender, to overcome both external obstacles and our internal ego, takes a lifetime to build within ourselves.

“It’s as if we don’t want to admit that we can’t do this alone, or that success may require dealing with the soft parts of ourselves, the uncomfortable, sticky parts we’d rather pretend weren’t there,” Holiday wrote.

He continued, “The myth is of the lone creative entrepreneur battling the world without an ally in sight. A defiant combination of Atlas and Sisyphus and David, wrestling a Goliath-sized mass of doubters and demons. In reality, I’ve found that nearly every person I admire — every person I’ve met who strikes me as being someone who I would like to one day be like — lives a quiet life at home with a person who they’ve teamed up with…for life. The reason this one person strikes us as special, I find, is because they’re really two people.”

Here’s Ryan explaining what happened after the ring was stolen, “I broke down and told her, though she’d clearly deduced it already. I showed her the ring I’d bought and she cried. It was exactly what she wanted, yet by definition irreplaceable.”

They looked at new rings together. “I bought the ring I knew she liked but was too shy to demand, but I said nothing, I said we’d find something later. They’d had it at the place the first time, but I’d ignored it because it wasn’t my taste. White gold, 1920’s vintage Art Deco, with blue sapphires around the diamond.”

“Would you believe I refused to put it in the new safe? I hid it instead, in a hollowed out book.”

On the Tim Ferriss podcast, Ryan Holiday said, “I was looking at my goats one day. … They weren’t eating, they weren’t head-butting each other, they weren’t jumping on something; they were just standing there. And I remember thinking “They’re just being goats.”

“With all this chaos, I’d actually started attending Workaholics Anonymous meetings when I was in Los Angeles.” He continued, “They say this thing in the meetings that it’s human being, not human doing.”

“When Cyril Connolly said that there was ‘no more somber enemy of good art than the pram in the hall,’ he was voicing, in appalling clarity, the selfishness and self-absorption that draws many people away from love and happiness,” wrote Holiday. “Maybe I worried about it when I was young and ignorant, but today, I don’t feel any shame in saying that I would have spun off the planet a long time ago if it wasn’t for [Sam] her.”

Ryan described a day he had with Sam in February of 2014; “We went to the Hamilton Pools in Texas, undoubtedly one of the wonders of the world. … For a twenty minute window there wasn’t a soul in the place and I asked. Total surprise. And she said yes for real and that was that.”

Ryan Holiday wrote about Samantha Holiday’s marriage vows; “She stated she would continue to manipulate me as long as she could, into whatever other ridiculous schemes and larks she’s decided upon. That she would be both my biggest supporter and even bigger distraction.”

With her support and despite her distractions, Holiday published his fifth book. It’s filled with wisdom for the struggles of everyday life: The Daily Stoic.

In an article for The Observer, Holiday wrote “Two moments now stand out at me in my life. Driving home, by myself, after my high school graduation, thinking: I am finally free. And now, driving with my father, on the way to my wedding.”

“Such different feelings toward two similar life events, almost exactly a decade between them. One, excited to get away — anywhere, anything. Now, excited to be here — to be at peace, like heading home.”


Photo by Brandon Morgan on Unsplash

The New York Times notes that Sam and Ryan Holiday have a small herd of 10 cattle, three goats, two donkeys, and chickens, ducks, geese and a guinea hen. “We don’t know that much about raising cows,’ Ryan Holiday said. “We’re learning.”

Learning is for life. Remember Robert Greene’s lesson? “It starts with wanting to create a classic.” Holiday’s sixth book is Perennial Seller: The Art of Making and Marketing Work that Lasts.

The whole of life is creation and destruction. Destruction and re-creation. A classic rises above that cycle. Like Meditations, Discourses, and Letter From A Stoic, a classic lasts generations. It’s perennial. Yet while classics can last, men cannot. Letters from a Stoic survives today, Seneca doesn’t. While Holiday may write a classic, he won’t be alive to see if his books last generations. But his lineage might.

In the You Made It Weird podcast, Holiday talked about Franz Kafka’s famous Letter to his Father, “Kafka wrote this long letter to his father. He had this very domineering father… and he never felt like he got him. And he suffered from this imposter syndrome his whole life.”

Kafka wrote, “Marrying, founding a family, accepting all the children that come, supporting them in this insecure world and perhaps even guiding them a little, is, I am convinced, the utmost a human being can succeed in doing at all.”

In The Origins and History of Consciousness Erich Neumann wrote,

“The reverse side of this father complex — which by no means implies liberation from it — is to be found in the “eternal son,” the permanent revolutionary. He identifies himself with the dragon-slaying hero, but is totally unconscious of his divine sonship. The absence of father identification prevents the eternal youth from ever obtaining his kingdom. His refusal to become a father and to assume power seems to him a guarantee of perpetual youth, for to assume power is to accept the fact that it must be passed on to a future son and ruler. The individualist is essentially non archetypal — that is to say, the eternal revolutionary, as he grows older, turns out to be a neurotic who is not prepared to “be his age” and accept his limitations. To negate the Isaac complex is not to get beyond it.”

Remember the letter Holiday wrote to his own father? Here’s how it finished;

“I was so happy to be able to tell you a few weeks ago that you have your first grandchild on the way and that he’s expected to arrive just three days before the election. I think that’s why I am writing this letter too, as my way of asking myself what am I going to do to make sure the world he enters is just a little bit better than the one I came into thirty years ago. I guess I am writing this letter to ask that you, as his grandfather, do what you can to ensure the same.

Dad, please don’t vote for Donald Trump. Everything you’ve taught me about what is wrong in the world is everything that man represents. And if you won’t do it for me, do it for your grandchild. Give him something to be proud of — and thankful for.

Your Loving Son,


In the You Made It Weird podcast, Holiday said, “What are you going to do with this pain or suffering or difficulty? Is it going to make you closer with your brother? Is it going to make you a better father?”

“For most people, what they went through is the excuse for why they suck. The Buddhists have this idea of samsarathe unbroken chain of pain. So how do you break that? … Maybe one way to find meaning in what we both struggle with is; I’m not going to pass this version of that on to this innocent child.”

As Holiday’s own letter makes it clear, he believes a father has a moral responsibility to do the right thing. In an ironic twist of fate, Ryan Holiday would now be put to test.

In an article for the New York Times he wrote, “In January 2017, I was offered a potential position inside the newly forming Trump administration: a job as communications director for a cabinet member. I had not supported Mr. Trump and so the offer was a surprise, and I surprised myself by even considering it.”

Considering working for Trump after asking his father not to vote for him?

To be fair, since ancient times the great philosophers have been called upon to serve their state. As Holiday pointed out in his NYT article, Socrates was a soldier in the Peloponnesian War and Aristotle worked for the “murderous warmonger”, Alexander the Great.

Still, “I didn’t pursue the opportunity very seriously and it did not come to pass,” wrote Holiday. He passed on the opportunity to ‘be somebody’. But soon, with Peter Thiel, he would have the opportunity to do something. He’d have the opportunity to give his own son, “something to be proud of — and thankful for.” But first…

PART III: Humility

“There is nothing noble in being superior to your fellow men. True nobility lies in being superior to your former self.” — Ernest Hemingway

Stoicism Before Success

Photo by guille pozzi on Unsplash

Ryan Holiday started with the right answer. He read Marcus Aurelius’s Meditations at 19. Yet he had asked, ‘How do I succeed?’, before asking, ‘How do I live?’ He started with the wrong question. But what stands in the way…

As Peter Thiel said to Holiday, talking about the alt-right leaders supporting the Trump presidency, “They are the most like Gawker. It’s not that they are willing to do anything in the name of the ideology, that’s the ends justifying the means. . . . The similarity is the nihilism: a mask for no ideology at all.”

Success has become modernity’s defacto ideology. We idolise the rich and famous. The successful. What happened to religion? Well, God is dead and we have killed him. Man’s search for meaning has become his own, alone.

For many chasing the great American dream, success is enough. Many, like Trump, crave excess. Perhaps, success and excess as an ideology, is really a “mask for no ideology at all.”

When we realise this, the real search for an ideology begins. The thing is, by nature, only the successful yet discontent ever begin the search. They’re searching for an answer to philosophies one real question; how to live? If they were already happy and content with their success, they would never ask the question. Most people don’t.

Ryan Holiday was the marketing director of a public company in his early twenties and had written multiple NYT bestsellers. He was living the American dream. Yet, he was still drawn to philosophy.

Before Holiday begins Ego Is The Enemy, he quotes Rainer Maria Rilke;

“Do not believe that he who seeks to comfort you lives untroubled among the simple and quiet words that sometimes do you good. His life has much difficulty and sadness and remains far behind yours. Were it otherwise he would never have been able to find the words.”

“In Workaholics Anonymous, one of the exercises involves a simple reminder. We must, they say, ‘catch ourselves before we relapse into ego and self-will,’” wrote Holiday. “Ego tells us that meaning comes from activity, that being the center of attention is the only way to matter.”

In the You Made It Weird podcast, Holiday shared, “Stillness to me isn’t this thing you go get. … it’s there already. You just have to figure out how to access it. You don’t get it by being rich; you don’t get it by getting famous; you don’t get it by doing this retreat; you have it already and it’s about unlocking it.”

Perhaps, Stillness Is The Key.

In his letter to his father, Franz Kafka wrote, “It is, after all, not necessary to fly right into the middle of the sun, but it is necessary to crawl to a clean little spot on Earth where the sun sometimes shines and one can warm oneself a little.”

Like Icarus, Ryan Holiday flew too close to the sun. And that’s exactly what makes him a great stoic philosopher. Like Aurelius, Seneca and Epictetus, Ryan Holiday has lived. He got dirt in his eye and perhaps a little blood on his hands.

The pain of life, of success and failure, has seared the stoic philosophy into his marrow in a way books alone couldn’t. He broke through to the other side. He found his own “little spot on Earth where the sun sometimes shines and one can warm oneself a little.” We can see him in the morning, on his ranch in Austin, writing his daily journal with his son on his lap.

So it must be, he was a man of action before a philosopher.

That is why we cannot read Holiday’s work and call ourselves a stoic. Or Senecas. Or Epictetus’s. Or Aurelius’s. Their books are only our beginning. We must rise from the cavea and enter the arena. As Marcus Aurelius wrote to himself, “fight to be the person philosophy tried to make you.”

Still, we must not confuse the “fight to be the person philosophy tried to make you,” with fighting. We cannot do ‘whatever it takes’ to succeed now, expecting stoicism to be there to rationalize away our sins later. Morality isn’t only for old men. And Stoicism has no confessional.

Before we get the right answers in life, before we fight, we must ask ourselves the right question. It’s not, ‘How do I succeed?’ It’s, ‘How do I live?

When we ask the right question, the answers become clear: Sinclair before Gawker, Tucker before Dov, Thiel before Trump.

In life, we must put things in the right order to deal with the chaos of life. What matters more than how others see us, is how we see ourselves. This is how we know what to fight for…

Truth before facts; Product before promotion; Suffering before wisdom; Virtue before fame; Sacrifice before love; Strength before muscles; Justice before nihilism; and Stoicism before success.

Nemo Me Impune Lacessit

Photo by Ricardo Cruz on Unsplash

When Ryan Holiday decided to do something and expose the corrupt media system in Trust Me, I’m Lying, he may have hoped it would change the corrupt media system.

Still, as Holiday reported, Gawker posted stolen nude photographs of female celebrities, sheltered millions in offshore tax havens and outed a gay man with a wife and children. And as sites like Gawker continued publishing unverified, manipulative, and salacious articles, fake news became harder to distinguish from true news.

After Upton Sinclair, after Hunter Thompson, after Ryan Holiday; what would it take for us to finally be able to say; “Something surprising happened: Media actually did change.”

Ryan Holiday wrote that Brass Check was “almost entirely forgotten by history.” Almost, but not entirely. For one thing, it inspired Ryan Holiday. Not only did Holiday write his Trust Me, I’m Lying in the spirit of Brass Check, the media advisory firm he built is named Brass Check.

We saw that the phrase brass check’ refers to “money given somewhat secretly to a journalist for services rendered to or expected by a financial interest.” But it has another meaning.

A ‘brass check’ confirms that a semi-automatic pistol has a bullet in its chamber, and is ready to be fired. The user pulls the slide back slightly, looks through the ejection port, and sees the brass of the cartridge. If the brass can be seen, the gun is ready to be fired.

While I don’t know if Trust Me, I’m Lying helped inspire the following conspiracy, it’s most fitting that Holiday was the one to write it. During his research, Holiday wrote, “Peter would, at one point, pass me a copy of The Fifteen Decisive Battles of the World…”

Our conspiracy begins with Peter Thiel, who — like Holiday’s father — supported Donald Trump. Yet while Holiday’s father became an enforcer of the law, Peter Thiel had planned to be the one writing it.

Peter Thiel went from Stanford to Stanford Law. With ambitions of serving in the Supreme Court, he knew the right clerkship would liberate him from needing to get a mundane corporate-law job. An opportunity for a Supreme Court clerkship arose. But alas, he was passed over.

“I was devastated,” wrote Peter Thiel in his book Zero To One.

Years later, Thiel would reflect, “winning that ultimate competition [for the clerkship] would have changed my life for the worse.” After working a mundane corporate-law job at Sullivan & Cromwell for seven months and three days, he walked out the front door and didn’t go back.

Peter Thiel went on to found and build PayPal, before selling it to eBay for $1.5 billion. He took part of his proceeds and founded a hedge fund. He also founded a company, Palantir, that analyses data to provide military insights, predict crime and fight terrorism. Their clients include the CIA and other three-lettered agencies.

Thiel became a powerful man. Who in their right mind would mess with him?

At 7:05 p.m. on December 19, 2007, Valleywag, a site that was part of the Gawker empire published the article: Peter Thiel Is Totally Gay, People.

To be fair to Gawker, Peter Thiel had somewhat of a media profile, and is, in fact, gay. Yet while his parents, friends, and colleagues knew, it wasn’t publicly known. Or something Thiel advertised. With ambitions of becoming the best technology investor in the world, he felt the identity of being ‘gay’ could interfere with or detract from his achievements.

In 2019, that may seem like an overreaction. But 2007 was a different era. As Holiday pointed out, “The Democrat who would be elected president in less than a year’s time was still five years away from announcing his support for same-sex marriage.” And “Thiel was then, barely notable. And he was, above all, a quiet, private person.”

While it comes across as a superficial-outing to many, Peter Thiel is a deep thinker.

In 1890, future Supreme Court justice Louis Brandeis wrote a piece in the Harvard Law Review that Peter Thiel and his Stanford cohort would read. As Holiday noted, “Most regard it as another piece of the puzzle that makes up American constitutional legal theory. But Peter believed it.”

That piece was the basis for what we now regard in many western-countries as our “right to privacy.” To paraphrase Justice Brandeis, “When personal gossip attains the dignity of print it destroys the robustness of thought and delicacy of feeling. No enthusiasm can flourish, no generous impulse can survive under its blighting influence.”

Thiel was just one of many who suffered the blighting influence of Gawker Media’s gossip. Yet Gawker thought they had impunity. Why?

Holiday explained Gawker’s perspective, “most people did not have the stomach — or the cash — to actually take it very far against a media outlet.”

“How do you respond to petulant blogs implying there is something wrong with you for being a gay person who isn’t public about his sexuality? Well, that’s the question now, isn’t it?” asked Holiday.

Thiel is not like most people. Holiday captured Thiel’s spirit with an old Scottish motto: Nemo me impune lacessit / No one attacks me with impunity.

After the following conspiracy was revealed, many in the high-media-towers felt that if Thiel really wanted to fight back against Gawker, he should have done so in print. He should have written an article. He should have started a rival publication. He should have fought fire with fire. But those Intellectual Yet Idiots don’t understand the most important thing in life. As the wise-owl Nassim Taleb writes, “You do not want to win an argument. You want to win.”

“Champerty — the funding of lawsuits you have no direct interest in — dates back to at least medieval times,” writes Holiday.

Peter Thiel didn’t sue Gawker for outing him. Instead, he hired a Los Angeles law firm and began searching for a champerty case. When Gawker published a private sex tape of wrestler and American icon Hulk Hogan, they had their man. Thiel secretly funded Hogan’s lawsuit. The lawsuit won and the settlement bankrupted the Gawker empire. Gawker slipped, Thiel made sure they fell.

Ryan Holiday’s seventh book tells the entire story of Thiel’s fight against Gawker, and the lessons we can learn from it. It’s called Conspiracy.

“William James [the Father of American psychology] knew that every man is ‘ready to be savage in some cause.’ The distinction, he said, between good people and bad people is ‘the choice of the cause,’” writes Holiday.

“For all the claims that what Peter had done was personal and unethical and wrong, that he had made the world a worse place and horribly wronged a group of journalists, something surprising happened: Media actually did change. Because they knew they needed to.”

In Trust Me I’m Lying, Ryan Holiday exposed the media’s corruption. In Conspiracy, he showed us what we need to do.

“From time to time in life, we might have to take someone out behind the woodshed. How we have lost this. How squeamish we have become,” writes the successful stoic Ryan Holiday.

And finally, who is Francisco d’Anconia? Francisco d’Anconia is a character in Ayn Rand’s infamous novel Atlas Shrugged. Francisco was a child prodigy who, while still in school, proved he could have made a fortune without inheriting his family’s copper mining operation. Still, he inherited the family company. He then purposefully bankrupted the company so it would not become part of a corrupt fascist system. He sacrificed wealth and status to pursue a higher purpose. He did what needed to be done.

Francisco d’Anconia… Tucker Max… Robert Green… Peter Thiel… Ryan Holiday. They’ve all played the ‘bad guy’. And they’ve been condemned, misunderstood, crucified. And that’s okay.

Because it’s okay to be misunderstood, when you understand yourself. It’s okay to be crucified, when you have an inner citadel. It’s okay for others to see you as ‘bad’, when the man in the mirror never blinks.

And it leaves you free. Free to forgo the person the world wants you to be. Free to leave that person out behind the woodshed.

Then you’re truly free. Free to do what the world actually needs.

Peter Thiel was born to be a titan of industry. Marcus Aurelius, Seneca, Ayn Rand, Ernest Hemingway, Nassim Taleb, Hunter S. Thompson, Tucker Max, Robert Green, and Ryan Holiday?

They were born to expose the ugliness around them, to reveal how human nature really works, and to help others become their own successful stoic. They were born to write. But because they chose to live first, their philosophies are destined to last.

Tom Chanter

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