Ryan Holiday: How Stoicism Transforms Leadership and Decision-Making in Business | Leadership | E347

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The Stokes would say that the greatest empire is command of yourself. It's not things that upset us.
It's our opinion about things. And realizing like as an entrepreneur, there's no such thing as a good market or a bad market.
There just is. Life is objective.
That's what the discipline of perception is about. What is the point of doing your own thing if you're not going to do it right? You're the boss.
You get to decide what you pay people, what materials you use. If you're not going to use that to make a positive difference in the world,

what are you doing?

There's so many ways you can make money.

And if money was all you cared about,

you should just go work in finance.

It's less risky and the upsides are probably higher.

How do you define a good life in Stoic terms?

The Stoics believed that life was... Yap gang, we are about to go super deep on the podcast today.
We're getting philosophical with today's guest and I can't wait. Ryan Holiday is joining us.
He's a philosopher, an entrepreneur, a marketer, and an author who has transformed ancient Stoic principles into actionable insights that we can use as modern entrepreneurs today. He's the host of the very popular Daily Stoic podcast and his latest book is called Right Thing Right Now.
Now for today today's conversation, I really want to spend some time on his come-up story. He was an apprentice for Robert Greene.
He was a marketing director for American Apparel at just 21 years old. He wrote a book about media manipulation.
I want to talk about that. And we're going to get into Stoicism and his new book about justice.
We've never covered Stoicism on the podcast, at least as deeply as we do in this conversation. So there's so much to unpack.
Let's dive right in. Here's my conversation with Ryan Holiday.
Ryan, welcome to Young and Profiting Podcast. Yeah, it's good to be here.
I'm so excited for this conversation. And when I was researching for today's episode, I found out that you started your career when you were 19.
You ended up dropping out of college at 19, which is the same thing that I did. I actually interned for Angie Martinez, who was like the biggest radio personality in the world at the time when I was in college for three years.
From the Breakfast Club, right? At 105.1 now, but she was at Hot 97. And so apprenticeships are so important.
You did it under Robert Green. I had him on the show, one of my favorite episodes of all time.
And so I want to start there. I want my listeners to get a really good understanding of your career journey because it's the first time on the show.
So what did you learn? How did it impact your future career? Well, I'd say two things about it. So one, these things become clear after the fact.
They start as a job. Somebody gives you a shot.
Somebody gives you something to work on. It only becomes a mentorship or an apprenticeship afterwards.
After a long time has passed, you can come to understand that's what it was. What really happened is I got a job as a research assistant for this writer that I really liked.
And in a world before AI, I transcribed interviews he was doing for a book that he was writing. And so it was just this kind of mundane task that I did well enough that it led to another one and another one and another one.
And all the while I was learning from him, I was able to ask questions, I was able to work on other projects. And it sort of developed into this relationship that continues to this day.
But Through it, I learned the art of writing, the art of researching, how to manage a brand, how to put out a book. I learned all the things that I do in my actual job now.
And I guess that's sort of the other thing, though, is that an apprenticeship or having a mentor, it sometimes can seem glamorous, but often a lot of it is just shit work. You're doing the things that they don't want to do, that their time is too valuable to do.
And you're glad to do it because their time is so valuable. You think about what an hour of this person's time would cost if it even could be purchased and you get access to that for free.
What I understood is that I was getting to work with Robert and occasionally I could ask him questions that could teach me things that I wanted to learn and that what he was paying me was extra on top of that. So when Robert came on the show, I remember he distinctly told me that he feels like young people don't spend enough time in the learning phase and he feels like it's so important for mastery.
So what do you have to say to all the young people tuning in about getting training, gaining skills before they go on and try to do the thing? There's a Zen story about this young student who wants to learn under this great master. I forget exactly what it was, but he says, you know, hey, how long is it going to take? And the master says, it'll take 10 years.
And he says, well, if I work really hard and I'm really focused, how long will it take? And he says, okay, 15 years. And he goes, no, no, no, I'm going to work really hard.
I'm going to be really focused. I'm going to do this faster than anyone.
How long is it going to take? And he says, 30 years. And the point is that what Robert is saying and what I think is a truism throughout

history is that this is the part of your life that you can't rush. I started working for Robert when I was 19, let's say.
And I would say I learned something from him a month ago when we were chatting. The process continues on to this day.
But my first book didn't come out until I was 25 or 26. So at a minimum, it was six plus years of working for him.
And I still felt like there was a lot left for me to learn and still think that there is. So these processes take time.
I wrote every day on my website for free for six, seven, eight years before I ever got a dollar for anything that I was paid to write. I'm thousands of episodes into the Daily Stoic podcast, thousands of emails into the Daily Stoic email.
I'm 12 or 13 books in as a professional author. And I feel like I'm just beginning to understand certain things.
I wouldn't say I'm just starting, but I would say that I'm just starting to hit my stride. And so one of the problems when you're young is you're impatient.
You want it now because you don't have it and you want to stop doing the shit work. You want to make your name.
You have things you want to say and you end up rushing that process. And as a result, you either don't learn things that you need to learn or you alienate people

or parts of the process that are really essential.

I feel like that's so true.

I align with everything that you said.

So you often say that Robert Greene taught you how to think, taught you how to write,

but I haven't really heard you talk much about how much he influenced your persuasion skills, your influence skills, and how that impacted how you marketed later on. What I really admired about Robert and what I still think is impressive about him is here you have a guy who writes about these obscure stories from ancient history, these things that most people don't wake up and say, hey, I want to know about this 14th

century prince in Holland or France, or I want to know about some samurai whose name

I can't pronounce.

And Robert has managed to not only make those things really compelling and interesting,

but he's done it in these enormous books.

And they're extremely popular with people who don't read a lot.

His books are often the most checked out books at libraries. They're the most shoplifted books.
They are incredibly popular in the prison system. Robert has done a really good job of making these ideas, these things that are really interesting to him, interesting to people who don't think they would be interested in those things.
Anytime you see someone doing something that shouldn't be possible, I'm really impressed by that. If you see someone, hey, this person, they're not tall enough, and yet they're thriving in the NBA, or they're old and their career as a runner is still going on, or they don't have a traditional education, and yet they managed to do X, Y, or Z.

I think you want to look at those kind of exceptions because they clearly figured out what actually matters, or they figured out how to do something in a unique way. And so what struck me about Robert's books that I've taken in my own is that Robert doesn't tell the reader a lot.
He shows the reader. Robert's books are primarily stories that illustrate timeless things about human nature, about seduction, about power, about politics, about life.
And so when I sat down to write about what I wanted to write about, which was ancient philosophy, one of the things I looked at was, okay, I can describe this philosophy and tell people what it's about, or I can show them what it's about through stories.

And that's probably the way that Robert's work influenced me the most.

And then as his research assistant, I really learned how you do that well.

I totally agree.

I feel like when I read Robert's stuff, I feel like I'm figuring out a secret, this like secret of life and figuring it out on my own through all the stories that he tells. One of his books is basically like 500 books.
Like he read all this stuff and he's distilled it down into a single volume and I'm going, okay, that's the job of the author is to take all these different ideas, all these

different cultures, all these different lessons, and put it in one package, kind of condense it

down, boil it down to its essence. So someone who Robert wants to go read 500 books, I love reading

500 books, but your average person does not have time to do that. They're not a history nerd.

And so how do you take what's interesting to you and put it together in a format that can work for someone who's busier or not so inclined? So after Robert Greene and your work with him, you went on to become the marketing director at American Apparel, and you were known for these bold advertising campaigns, controversial, disruptive. So what was your marketing philosophy when you were leading those campaigns? And can you share some examples of how you got media attention? The biggest hustle that I pulled off is that I got paid to work for Robert Greene as he was actually teaching me.
And then I went on and I did digital marketing for American Apparel and then ran much of their traditional marketing as well. But all the while, I was learning from Dov Charney, who was at that time a marketing genius who'd sort of figured out how one generates earned media with sort of provocative advertising campaigns.
So I did a lot of campaigns, but I also learned from him. And that's kind of how I've gone through my career is like, who's someone who's doing something really interesting? Who's doing something that I don't know how to do? And how can I take something that I do know how to do, add value there, and then take value in terms of learning how to do it in a different or a better way? And basically, the philosophy at American Apparel was, if you're boring, you have to spend a lot of money to get people to see what you're doing.
If you play it safe, you have to spend a lot of money to catch people's attention. But if you do things that are provocative or transgressive or different or unusual or experimental, well, not only is that stuff often cheaper, but it breaks through the noise.
And so at American Apparel, they didn't use

professional models. They didn't use Photoshop.
They didn't use celebrities. They used regular

people, men and women. Then they took sort of risky and risque photos that we then put in

unique placements. So billboards, which I think were often underrated at that time.
We bought on websites that people weren't buying on. We bought on social media when that was new.
We bought on the back page of sort of weekly newspapers that your traditional brands didn't think were big enough, didn't think were shiny or fancy enough. We were trying to look for the underexploited opportunities.
And when you take risks and when you push the envelope, you often get what is called earned media, which is really the only media that matters. If you're paying to put your boring television commercial in front of people over and over and over again, you have to spend a lot of money and your impact ceases the second it goes away.
But if you can do something that's interesting and provocative that crosses over and becomes a news story, or it gets banned, or it gets graffitied, or somebody rips it out of the magazine and puts it on their wall because they think it looks so cool, that's what we were trying to do. And so I just try to think about how am I going to stand out? And I just always remember that being boring is really expensive.
And that was like 2007. So that was before like social media was even that huge.
Do you think all this stuff really works now? It works because of social media, right? So if you buy a billboard and people pass by it on the way to work, you're going to reach however many people pass by that freeway or that street corner. What we figured out at American Apparel and what I think about and have thought about for campaigns in the years since is like, if I can make a billboard that's so interesting or so provocative that people take a picture of it and post it on Twitter or on Instagram, or they make a YouTube video about it, or it gets banned and then a news story writes about it.
Now people who will never drive in that side of town or don't even live in your country, now they're hearing and talking about it. And so what social media does is it makes things shareable.
So if you can create things that are shareable and interesting and provocative, then you can tap into that energy and force. Did you ever feel like you went too far with the stuff at American Apparel? Of course, American Apparel went way too far, way too many times.
And one of the problems with courting controversy is that sometimes you get it for things that you don't deserve. I remember one of the things that was sort of an eye-opener for me is this sort of activist or artist or whatever, they started making fake American apparel ads.
And they would Photoshop this like onto billboards and street corners, onto pictures of them. And then they would send those pictures to websites and then people would get mad about American apparel ads that didn't exist.
And then you go, okay, well, on the one hand, it's cool that we've created something that's so provocative and newsworthy that people are willing to talk about it. But here we are getting in trouble for something that not only we didn't do, but is fake.
And so I talk about this in my first book, which is about media manipulation. You can feed a monster and it starts off really small and friendly, but then it becomes this big, scary, dangerous thing.
And then maybe it eats you. And I think that definitely happened at American Apparel.
So you just mentioned this book that you put out. So you went from like media manipulator to media whistleblower in this book.
And you were just talking about how you can basically manipulate the media. And now everything's gotten so much worse.
That was 2012 when you put out that book. Now we have AI.
Social media is way bigger than it was. And people not only can manipulate what clothes you buy, but also politics, the economy, all these things.
So talk to us about how things have gotten worse since then or some of the concerns that you may have? Yeah, I remember when Elon Musk took over Twitter and he eliminated the verified checkmark. That day, a sort of a prankster created a fake account for Eli Lilly, the drug company, and he put out a tweet that said, insulin will now be free.
And their market cap dropped billions of dollars in an instant. And so what I was talking about in that book is the way that on the one hand, the sort of exciting and unregulated world of social media and new media and all these tools, it makes it really easy to break through the noise and to stand out and to create a brand for nothing.
It also creates a lot of vulnerabilities if you have a big and valuable brand to be attacked, to screw up, to have things that are not true get spread about you. And so what I was trying to do in that book is kind of tear back the curtain and go like, look, this is how it really works.
And this is probably not an ideal system for anyone. And my goal in writing that book was really like, I just didn't, that's not what I wanted to do with my life.
And so I took all the things that I knew that I'd seen that I'd sort of read about and I sort of put it all in. I just said, look, this is it.
And that was part of it for me. That was my first step towards becoming a professional writer, which is what I'd always wanted to do.
And is there any way to use like these concepts that you use to infiltrate the media for good? Of course. A tool is a tool.
You can use an ax to chop down a tree or you can use it to murder someone, right? Or you can accidentally cut off your hand. But the tool is not good or bad.
It simply is. And if you're trying to change public opinion, you have to understand how public opinion is formed.
If you don't understand the sort of levers of power, if you don't understand the logic of where people get their information, you're going to be doing what I think a lot of good people who are trying to do good, unfortunately, find themselves struggling with, which is they go, my work is so important. It matters so much to me.
It's going to make a positive difference in the world, but nobody cares. I can't get anyone to write about me.
I can't get anyone to talk about me. I can't get anyone to try what I'm doing.
If you don't have a good eye for marketing and the ability to break through and communicate what you're doing, it doesn't matter how great your product is. Let's hold that thought and take a quick break with our sponsors.
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So you went to writing about the media to then stoicism and personal growth so what was the turning point there how did you find out about that philosophy and what made you kind of switch to talking about personal growth well i always wanted to write about ancient philosophy that was what i was fascinated with that's what i loved that's what something robert and I connected over is sort of, we just love ancient history. But I understood that publishers weren't exactly lining up to give book deals to kids in their 20s who had dropped out of college to write about an obscure school of ancient philosophy.
And so I went and I had a career where I made money. I developed a bunch of relationships.
I developed a platform. I published a book about a different topic.
All of this was setting up getting in a position where I could have a little bit of power and say about what I did next. And that's what that transition was designed to do.
So I think some people go, how'd you go from writing about public relations and

marketing to ancient philosophy? Well, it wasn't like I just woke up one day and said, hey, I want to do the opposite of this. It was a plan.
I was working towards having the freedom and leverage to control my own destiny and to talk and write and, you know, make content about the stuff that I wanted to make content about. So we've never covered stoicism on the show, and I know very little about it.
Just researching for this interview is when I learned about it. So we're going to go deep on this.
I want you to tell us about all the different principles. So first of all, how do you define a good life in stoic terms? The Stoics believed that life was unpredictable.
Life would be full of adversity and challenges and difficulties. And that one had to cultivate kind of an inner strength, an inner sense of purpose and values that could guide you through the inevitable ups and downs of existence.
And so Stoicism, to me, my definition as I've tried to introduce people to it over the years is this idea that, look, we don't control what happens, but we control how we respond to what happens. And so I actually do think it's a philosophy, it's an approach to living that works well as an entrepreneur, as an artist, as a creator, as a small business owner.
What I've tried to do is take these ideas from the Greeks and Romans, you know, going back 23 or 24 centuries and make them applicable and accessible to the kinds of things I was going through as an executive, the things you might be going through running your own show, or that, you know, somebody who's just trying to figure out their way in the world is going to need, but not think, hey, what

can ancient philosophy teach me about this?

And it is ancient, right?

It's 2,000 years old.

So what makes this stand the test of time?

How is this still relevant 2,000 years later?

I think sometimes we think that the ancient world was this thing that happened for like a brief period. But the ancient world was thousands of years old.
So Marcus Aurelius, the emperor of Rome, one of the most well-known Stoics, he comes to Stoicism like 500 years after it was started. So it was ancient philosophy to him, a man whom to us is an ancient philosopher.
So for hundreds of years

and now thousands of years, the Stoics were entrepreneurs and athletes and actors and soldiers and politicians and husbands and wives and sons and daughters, human beings trying to make their way through an unpredictable, random, frustrating world. And these lessons survived to us.
They weren't just speculating about stuff. They learned it running the Roman Empire.
They learned it leading troops into battle. They learned it recovering from a shipwreck or being sent into exile.
So what the Stoics teach us is not like abstract ideas, but really sort of hard won practical wisdom about how you deal with the hand that life deals you. So I thought a way that we could kind of break down some of these complex ideas is to do it quickfire style.
All right. So you have three main disciplines and then you have four cardinal virtues.
So I thought we could kind of go through each one. You could tell me what is the key takeaway, the key learning for each one.
Does that sound good? Let's do it. Okay.
Let's start with the three main disciplines. Discipline number one, perception.
So in The Obstacle is the Way, I sort of break this art of turning difficulty or problems

into an advantage or into an opportunity.

And it's built around these three stoic disciplines, which is first the discipline of perception.

That's how we see things.

That's our judgment about things.

Then there's action.

What are you going to do about it?

And then will is like, how do you

endure? How do you survive? How do you get through tough stuff? So a quote from Mark's realist, it sort of encapsulates this. He says, objective judgment now at this very moment.
Then he says, unselfish action now at this very moment. Then he says, willing acceptance now at this very moment.
that's all you need. That's a stoic formula for taking something that is challenging or heartbreaking or painful or discouraging and flipping it upside down and turning it into something that, you know, in retrospect, you're like, I'm glad this happened.
I was able to do X, Y, or Z because of that thing happening. Can you go deeper on just how to turn obstacles into opportunities? Because I know that you talk a lot about that.
Okay. Look, there are always things that we can do in response to a situation.
Is every obstacle a chance to succeed professionally and increase our profit margins? No, sometimes. But every situation is a chance to learn.
It's a chance to grow. It's a chance to change.
It's a chance to connect with people. It's a chance to be a good person.
And so what the Stokes are saying is that every situation in life is an opportunity to practice virtue. It's an opportunity to be excellent, not always in the way that you want.
A business partner robs you blind. Is that a chance to grow your business? No, your business is going to be negatively affected by this.
But is it a chance for you to practice standing up for yourself? Is it a chance for you to practice forgiveness at some point? Is it a chance for you to practice determination and creativity as you dig yourself out of this hole? Yes, you can do all of that. So when we say the obstacle is the way, what we mean is this situation is going to present you opportunities to do things that you wouldn't have done ordinarily.
And in that, you can be made better. Can you talk about related to perception, how it it shapes our reality? The Stoics have this great line.
They say, you know, it's not things that upset us. It's our opinion about things.
And realizing, like, as an entrepreneur, there's no such thing as a good market or a bad market. There's no such thing as a good call or a bad call.
There just is. Life is objective.
And then we have opinions about things. We put things into categories.
We say, oh, what they said was rude, right? Or a reporter writes an article about you. And you go, was it a good article or a bad article? No, it's just words on a page, right? And then we decide that we've been helped by it or hurt by it.
And understanding that you have the power to define things and to decide what they mean to you, that's what the discipline of perception is about. And I know emotions is core to all this and figuring out how to deal with our emotions.
What do we need to know about that? When people hear the word stoic, they often think emotionlessness. I don't think that's what it is.
Were the stoics trying to be less emotional? Yes. Because we very rarely make good decisions out of emotion.
Our emotions can blind us. So the stoics were trying to put those emotions to the side for a second and see what we're really dealing with, to see it as clearly and as objectively as possible.
But they still love, they still get excited, they still get afraid, They still have the full spectrum of human emotions. They just try not to be blinded by those emotions, particularly when we're making tough decisions.
When I was learning about stoicism, and I know a lot about Robert Greene's stuff, there was parallels, but stoicism is kind of like manipulating yourself, and Robert's stuff is kind of like manipulating other people's perception to persuade them

or influence them.

That's interesting.

One of the things the Stoics say is that the greatest empire, right?

Like Robert's books are like how to build an empire.

That's what he's talking about.

But the Stoics would say that the greatest empire is command of yourself.

How many people are extremely powerful, extremely wealthy, extremely famous, but they're not

in control of their own lives?

Stay tuned. greatest empire is command of yourself.
How many people are extremely powerful, extremely wealthy, extremely famous, but they're not in control of their own lives? They're not in control of their moods. They're not in control of their desires.
They're not in control of themselves, period. And so for the Stoics, sure, they wanted to be important and significant and achieve things, but they tried to conquer themselves first.
I think that's a really important part of the philosophy that you notice there for sure. So you also talk about these cardinal virtues of Stoicism.
There's four of them. Do you want to tell us about that? The Stoics are saying that everything is an opportunity to practice virtue.
What do we mean by virtue? The Stoic virtues are really simple. They're courage, self-discipline, justice, and wisdom.
So when we say that everything's an opportunity, that's what we mean, that a business setback is a chance to practice self-discipline. Now you really gotta run this operation lean.
Somebody just stole money from you. This is a chance to practice justice, either holding them accountable or forgiving them.
Courage, this is the chance to stand up, to keep going, to put ourselves out there. And then wisdom always allows us to turn obstacles into opportunities because we can use them as a chance to learn, if only about ourselves.
That's what the Stoics mean when they talk about how we always have the chance to practice virtue. Everything is going to demand from us or has a chance for us to demonstrate courage, discipline, justice, and wisdom.
Like you just mentioned, these philosophies are really great for entrepreneurs because we have uncertain environments. We've got to keep our cool in the highs and the lows.
So I want to ask you some follow-up questions related to entrepreneurship in particular.

So you talk about Amor Fati.

Tell us about that and why entrepreneurs can use that as they come across failures and setbacks.

Acceptance, which is what Amor Fati is about.

Amor Fati means a love of fate.

Acceptance can be a hard sell to entrepreneurs because they're sort of like, well, I didn't get here by just accepting things. And so it feels passive or it feels weak.
But actually, you did get here because of acceptance. You accepted that it's raining outside.
You accepted that you're going to need to raise money to start your business. You accepted that most people are busy and don't care about what you're doing.
And that's why you designed a marketing plan. That's why you designed a fundraising plan.
That's why you got an umbrella, right? You have to accept reality before you can set about changing it or you can set about succeeding despite it. And so Amor Fati is this idea that instead of resenting things, instead of dreading them, instead of wishing they were otherwise, you accept them for what they are, you embrace them, and you're excited about it.
It's like turning the have to into get tos. It's deciding to embrace it and love it and to love the challenge of it.
To me, that's what it's about anyway. So it's love of fate is the translation, right? So basically it's saying it's going to happen no matter what and you should just be okay with it.
Like why be upset about it? I think that's part of it too. Like, look, did you think you could start a business and never have a down quarter? Did you think you'd never have to fire anyone? Did you think you'd never be criticized? Did you think you'd never make any mistakes? That's preposterous.
This is part of it. This is what you signed up for.
This is how it goes. You should love that.
If you really love this, if this is really what you're meant to do, you love that shit too. And you love that it's all part of it.
And you're excited about the no's and you're excited about the setbacks and you're excited about the problems that you get to solve because that's part of it. It's hard when you're like, I'm an entrepreneur, I have a business, I have a social agency, I have a podcast network.
And in the beginning, it really is hard. You feel like, oh no, I lost a client.
The first time is always hard. And then after a while, you're just like, it doesn't matter.
Like, this is just the ebbs and flows of a business. You know, nobody's going to stay forever.
No employee is going to stay forever. And that's just how it goes.
Yeah, that's life. So decision making is something that stoicism can really help us and especially making clear headed choices.
To me, a key part of stoicism, like when you hear someone is philosophical, you don't mean that they know a lot of ancient philosophy. Like when we say, oh, that guy's really philosophical or she's really philosophical, what we mean is like, oh, she sees the big picture.
She's calm. She's not easily rattled.
And that's what Stoicism is really helping us get towards the ability to see the forest for the trees, to see what's really going on, to sense what's actually important, what's actually true in a given situation, as opposed to what a lot of people are, which is blinded by what's happening around them right now, distracted by noise, blinded by their emotions, and they're not philosophical. They are only seeing part of what's in front of them.
And so, yeah, I think stoicism is about making good choices, seeing things clearly. That's what the discipline of perception is really supposed to help us do.
So I know you tell a story in your new book, which we're going to get into later on, but I think it's relevant right now about Truman making a really hard decision. How is this related to being clearheaded, justice, all the things that we talked about? I mean, that's what leaders do.
That's when Truman has that sign on his desk that says the buck stops here. That's what he's talking about.
When you're low up in the organization, you can kick the decisions up or down. You can make it your employee's problem.

You can make it your boss's problem.

But ultimately, the boss is the decider.

The boss has to choose.

And if you don't have a strong set of values, if you don't have good judgment, if you don't

have the ability to see things clearly, what they actually represent, what they mean, you're

going to not make good decisions.

You're going to get in trouble. And so the Stoics weren't these sort of academic philosophers who just read books.
They were leaders. They ran organizations.
They ran empires. They led troops into battle.
They were making real decisions in the real world. And they understood that this was a skill you develop the only really way you can, which is by experience.
I love our listeners to hear stories. And you talk about Roman Emperor Marcus Aurelius.
So he was an emperor, which kind of is like being a CEO running a company. So share the story about him in general.
Like what leadership principles can we take from him? What can we learn from him? Well, I mean, look, he's the chief executive of the largest empire in the history of the world. He oversaw something like 50 million people, thousands, tens of thousands of square miles.
It was enormous. He was the most powerful, important person in the world.
And he struggled, as I think we all do. I mean, his reign was an unending series of troubles.
There was floods. There was a plague.
There were natural disasters. There were wars.
He had health issues. He was also a father and a husband.
And he had to deal with Murphy's law, what can go wrong will. But he tried to see this as an opportunity.
He said, good fortune is what you make for yourself. It's one of my favorite quotes from him.
He's like, by doing good things, by thinking good things, by treating people well. And so what we see in Marcus is one of the few examples.
There's that expression about how absolute power corrupts absolutely. It's one of the few examples where that doesn't happen.
And it doesn't happen because of his grounding in Stoic philosophy. He would journal every day.
He was still reading. There's a famous story about Marcus Aurelius.
Towards the end of his life, he's seen leaving his palace in Rome. And a friend stops him and he says, where are you going? And he says, I'm off to see Sext the philosopher, to learn that which I do not yet know.
Even as an old man, he still saw himself as someone who was learning on the job, who had room for improvement, that he was a work in progress. And in this way, he's one of the greatest human beings who ever lived.
That makes me feel like, man, like I wish like Trump would get into stoicism or something. We need that in our leadership.
I'd be happy if he read one book ever. I don't think that's going to happen.
Look, there's a great stoic line that I think applies not just to him, but to so many leaders. Epictetus, who wasn't the emperor of Rome.
Epictetus was a slave whose philosophical writings would influence Marcus Aurelius. But Epictetus would say that it's impossible to learn that which you think you already know.
So if you're someone who is humble, who is hungry and trying to learn, you will continue to learn. If you are someone who thinks that you're just naturally brilliant, if you think you're better than everyone else, if you think you're perfect, you can't learn.
You become frozen in place. And I think that's a trait that defines a lot of really mediocre to outright bad leaders, which is they're so egotistical that they can't get any better.
I was just going to say, it sounds like you're talking about ego. And I feel like entrepreneurs have a lot of problems with ego.
A lot of the times it's what got us to where we are now, but it's not going to help us get to where we want to go. So talk to us about how ego can be our enemy as entrepreneurs.
I think it's important we make a distinction between confidence and ego. I think confidence is something you learn.
Confidence is something you develop. And ego is like is stolen or ego is is on much shakier ground.
So again, look, Socrates is considered wise because he knows what he doesn't know. Egotistical people think they know everything.
They think that everything is about them. They think they're better than everyone else.
They think the rules don't apply. And this is why they end up almost always overreaching, causing drama, getting sucked into conflicts, missing warnings.
And it's also, I think this is a big thing, egotistical people are very easy to manipulate because you can flatter them. You can deceive them.
You can tell them what they want to hear. A humble person, a confident person, they don't mind being disagreed with.
They seek out divergent opinions. They're not threatened by talented people.
Look, that was one of the problems at American Apparel. Dove, who was brilliant and very successful, was reluctant to hire other competent people around him because he thought they would constrain him.
He thought they would challenge him.

Like, look, on one level, it was absurd that I was the director of marketing at a publicly traded company at 21. It worked out okay in my case, but there were just a lot of people there, again, myself included at times, who were just unqualified to be there.
But because we were less threatening, that's why we were there. And that is a recipe for building a dysfunctional organization and team.
It's so true. You really got to make sure you've got smart people around you that know more than you.
But to your point, if you're too egotistical, you end up with people, knuckleheads that don't know what they're doing so that you can just tell everybody what to do. Okay.
So we're entrepreneurs. A lot of the times we don't have a boss and it's sometimes hard to have any sort of accountability.
We got to just wake up and decide we're going to do this, have our own motivation. Can stoicism help us with that? Yeah, look, that's what this virtue of self-discipline is all about.
And I do find people struggle with that. I think a lot of people experienced that during the pandemic.
Suddenly they were working from home. Suddenly there wasn't a boss looking over their shoulders.
And then they realized, oh, I have to be the boss. No one can make me do any of this.
No one's going to remind me about any of this. I get to choose what order I do things or what I do and don't do.
And there's a part of me that doesn't want to make the right choices. And stoicism is about holding yourself accountable.
It's about doing the hard thing. It's about pushing yourself.
It's about growing. And so, yeah, that requires that willpower.
One of Seneca's lines, which I think about a lot, he says, we treat the body rigorously so that it's not disobedient to the mind. One of the reasons I have a physical practice, I run or bike or swim every day or I lift weights, I do hard stuff because I don't want to do hard stuff.
What you learn in the gym, what you learn on the road is that there's the part of you that doesn't want to do it, that wants to huddle under the covers, and the part of you that's glad afterwards that you did it. And you have to fight to get from here to there, right? The part of you that doesn't want to make one more call, that doesn't want to do one more draft, that doesn't want to have interview one more candidate.
That's the part that you have to conquer, you have to get over to get to the other side, to get to that next level of performance or success. Okay, so last question on stoicism, then I want to get into your new book for a little bit before we close.
Is there one principle that you wish that you'd known in your 20s or 30s during your career? I know you're still in your 30s, but. I would say that my 20s were very intense and my 30s have been very intense.
But the more I slow things down, the more deliberate I am, the more intentional I am, the better I seem to do and then also the happier I am. And I just look back and I go, why was I freaking out about that? Why was I in such a rush back then? Why did I think this was such a huge deal? And it's only with time and experience that you are able to slow down a little bit and get that perspective.
If I could give myself the ability to relax a little bit, I don't mean relax my standards. I just mean to not be so high strung.
I think I would have done better and I would have enjoyed it more. I remember when I was 25, I used to feel like I was so old and I'd be like, oh, I'm too old to do that.
I feel so old. I'm too old to do this.
And then looking back, I'm like, what was I thinking? You know, I wasn't too old to do anything. And I feel like young people feel older than they are all the time.
And it's not till you're in your 30s when you're like, what was I thinking? Yeah, look, especially if you're ahead of the curve, right? Like, especially if you're a driven,

talented young person, you feel old already because you're doing stuff when your friends

are out partying or whatever. But yeah, you have so much time and you are still so early in the game.

But it's only with the passage of time that you can understand the passage of time, right? And so that perspective that I have now, I wish I could give to myself a little bit more earlier. We'll be right back after a quick break from our sponsors.
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Okay, so you have a new book. It's called Right Thing Right Now.
What was the aim in writing this book? What was the new information that you wanted to share with everyone? Well, I've been working on this series about the cardinal virtues now for almost six years. So I did one on courage.
I did one on discipline. And then this was the one about justice.
And I think when people think of justice, they tend to think of the legal system. They think of whether something is against the law or not.
But justice is how you treat people, the standards you hold yourself to, the morals you adhere to. I guess I would ask every entrepreneur on this call here, what is the point of doing your own thing if you're not going to do it well and if you're not going to do it right? You're the decider.
You're the boss. You get to decide what you pay people, what materials you use, the quality control that you insist on.
If you're not going to try to use that to make a positive difference in the world, what are you doing? There's so many ways you can make money. And if money was all you cared about, you should just go work in finance.
It's less risky and the upsides are probably higher. If you've decided to make something, it's because you want to make something that doesn't exist.
You want to do something the right way and you should let that guide you. I know in the book that you argue that doing the right thing is the hardest path.
So why do you think that leaders, entrepreneurs struggle with making the most ethical decisions? Well, because we also have a bottom line, right? We're also trying to be profitable. You're deciding between using this supplier, which is made in a sweatshop in some foreign country, and then this one, which makes a higher quality product, but pays its workers a living wage, that suddenly is not simply an ethical issue, but it's also a P&L issue.
And I actually remember at American Apparel one time, someone was suggesting that Dove move the factories overseas. And he looked at them and he said, if all I cared about was making money, I'd have become a drug dealer.
And I think about that all the time. It's like, oh yeah, I chose not to, by definition, you've already chosen not to do a bunch of super unethical, but potentially profitable things.
So here, as you're making a decision, don't let profit be the only thing you're thinking about because you have other values. And as an entrepreneur and as a leader, I think you have an obligation to try to make the world a better place.
Do you feel like there's a difference between doing the right thing and doing the smart thing? Yeah, sure. Look, if all I was thinking about was selling books, would I have written a book about justice? No, there's other topics that are more straight down the middle.
My book on discipline, a lot of people want to learn about discipline. A lot of people need discipline.
A lot of people are trying to overcome obstacles. There are other topics that I can write about that I know will do better.
But this is the one that I felt called to do. This is the one that was important to me.
This is the one that was creatively fulfilling. This is the one that I think no one else has done.
So it's weighing those other concerns. So is it the smartest thing to do? No.
But is it the right thing to do? Is it what I want to do? Yes. So that's why I'm doing it.
So back to stories. Harry Truman, he ended up dropping two atomic bombs on Japan and he became a very hated president.
Talk to us about that decision making and how it's related to justice. Well, Truman is a character in the book for precisely this reason.
He's in some ways one of the most ethical and least corrupt of the American presidents, one of the most thoughtful, in some ways one of the most progressive. He desegregates the armed forces.
He challenges the Southern Democrats in his own party as he begins to tackle race, and one of the only presidents not to make himself very rich while holding the office. In fact, the reason there is a presidential commission is that Harry Truman was so principled out of office and refused to cash in on having been the president that they thought he might end up bankrupt.
And so Congress allocated a pension for him. On the other hand, as president, he had to make a lot of difficult decisions.
That's what being the president is. And the decision to drop the atomic bomb is one of the obviously most morally consequential choices of the 20th century.
One of the flaws for Truman is that I don't think he ever really thought of not doing it. It was a project he inherited from his predecessor.
The military was united in its recommendations that they drop it. And so he sort of, I wouldn't say went along with it, but never really contemplated the idea that there might be another way to end the war.
On the other hand, he would say, if you asked him, he would go, look, my obligation is to the mothers and fathers of American soldiers who, as per the current estimation, several hundred thousand of them would die in a potential invasion of Japan. And so as the American president, who is my obligation

to when I make this decision? Is it to the men and women who voted me into office, whose children I

am sending into battle? Or is it to the people of Japan? And we would say that there's a tension between these two choices. And ultimately, he makes the decision.
I don't say in the book whether I think it was the right or wrong one, but without a moral compass, without a sense of our obligations and our duties and responsibilities, a country, a nation, the world is in very rough shape. And I think we're seeing now what happens when you put someone in the Oval Office whose primary obligation seems to be to themselves and doesn't see themselves as really having any ethical constraints in any way and actually has kind of a penchant for revenge as a list of enemies they want to punish, that's where you really get yourself into trouble.
Well, let's end this interview on a high note. So what is one daily habit or mindset shift that we can do to do the right thing, even when it's difficult? The most basic practice in Stoic philosophy is journaling.
The Stoics spend time every day thinking about things, talking to themselves, talking to Paige about what they're struggling with, about what their values are, about what's important, about what their options are. And I think adding a journaling practice into your life as an entrepreneur is not only going to help you slow things down, not only help you get perspective, but it's going to root you in your values, in your principles, in what's important in a way that basically nothing else can.
If I could leave everyone here with something, it would be this idea of a journaling, a philosophical journaling habit. So philosophical journaling habit, like what questions would we ask ourselves? Like what's, how does that differ from regular journaling? Just because I never heard of that.
I'm not talking about here's what I had for breakfast. Here's what so-and-so said to me yesterday.
Here's what my goals are. It's more like, how can I be better? Where am I falling short? What's my duty here? How can I resist this or that? How can I do more of this or that? To me, it's kind of having a dialogue with the self where we're trying, as we said earlier, to fight from where we are to where we want to be.
That's what we're trying to journal about and ask ourselves about. Okay, so I end my show with two questions that I ask all of my guests.
This has been an awesome conversation. What is one actionable thing our young and profiters can do today to become more profitable tomorrow? Is profit simply making more money or is profit also getting more efficient? And so I would ask myself, Hey, where am I wasting a lot of time? Like where, what are biggest time sucks in my life? And this is a very key Stoic practice.
The Stoics talk about how we never let someone steal money or property from us, but we let people steal our time. And so how can we be more protective of our time, which is our most precious of resources? I try to do an audit of my schedule and my time and get more effective and efficient with my time because that creates the ultimate form of profit.
And so true. Time is the most valuable asset that we have.
What is your secret to profiting in life? And this can go beyond financial. I don't know if I have a secret, but I try to do what I'm supposed to do every day.
I try to show up, try to work hard. I try to give my best.
And then I don't think that much about the outcomes. I just focus on what I control, which is what I'm putting out there, what I'm putting in there.
And I let the rest take care of itself. It's obviously working for you, Ryan.
Where can everybody learn more about you and everything that you do? Yeah, I send out a Stoic-inspired email every day at Daily Stoic.

There's a podcast version of it also.

And then I do a parenting one as well.

It's called Daily Dad, which you can check out at dailydad.com or Daily Dad on wherever

you get your podcasts.

Amazing.

I'll stick all those links in the show notes, Ryan.

Thank you so much for your time.

Oh, my pleasure.

It was so awesome to speak with Ryan Holiday today and learn more about his Stoic philosophy. I think it's an approach to living that just has so much to offer, especially for us entrepreneurs.
The ancient Stoics looked around at our world that was just as unpredictable as our own today, one that's filled with challenges

and difficulties. And they figured out a way to craft inner strengths and a sense of purpose that could transcend the chaos of daily life.
And just like a good entrepreneur, they figured this out through experience, hardship, and trial and error through actually running things and managing other people. Here are some of my favorite pieces of stoic wisdom

that Ryan shared.

First, meet every moment with a willing acceptance.

If something is painful or discouraging,

figure out a way to find the silver lining.

Every situation is an opportunity to be excellent,

to learn, grow, change,

even if it seems like a disaster at the time. Remember, the obstacle is the way.
Next, love of fate. Instead of resenting where life has placed you, embrace it.
Move with it, not against it. It took Ryan years to hit his stride, to be in a position where he could make the type of content he was born to create.
Finally, good leaders are confident, but not arrogant. Let's face it, ego is a problem for a lot of us entrepreneurs.
In part, that's because you need a healthy amount of self-confidence and motivation just to survive and persevere out there. But remember, like Ryan said, egotistical people think that they know everything.
A good entrepreneur, on the other hand, like a wise philosopher, knows how much, in fact, they do not know. They seek out the truth and what works, and they don't mind being disagreed with.
They know they can get better, and they're on a constant quest to do so. All right, ready to embrace your fate and accept this moment? If you listened, learned, and profited from this episode of Young and Profiting, then please share it with somebody else.
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This is your host, Hala Taha, aka the Podcast Princess, signing off.