Young and Profiting (YAP) with Hala Taha
Ryan Holiday: How Stoicism Transforms Leadership and Decision-Making in Business | Leadership | E347
Tue, 22 Apr 2025
Ryan Holiday dropped out of college to apprentice under Robert Greene, gaining invaluable insights on writing, entrepreneurship, leadership, and human nature. This mentorship laid the foundation for his bold marketing campaigns at American Apparel and his rise as a bestselling author and entrepreneur. In this episode, Ryan reveals how stoic principles can sharpen leadership skills, improve decision-making, enhance problem-solving, and empower entrepreneurs to overcome challenges for sustainable growth. In this episode, Hala and Ryan will discuss: (00:00) Introduction (01:44) Robert Greene's Influence on His Career (09:04) Leveraging Controversy for Marketing Success (14:18) Media Manipulation and Its Impact (18:30) The Stoic Approach to Life and Business (26:39) The Four Stoic Virtues for Personal Development (28:01) Embracing the Realities of Entrepreneurship (30:29) Mastering Clear Decision-Making (36:07) The Dangers of Ego in Leadership (38:31) How Stoicism Drives Productivity (42:59) Building Ethical Habits and Leadership Skills (47:50) The Power of Effective Time Management Ryan Holiday is a bestselling author, entrepreneur, and media strategist known for popularizing Stoic philosophy in modern culture. He served as Director of Marketing at American Apparel before founding his creative agency, Brass Check. Ryan’s books, including The Obstacle Is the Way and The Daily Stoic, have sold over 2 million copies in 30 languages. His work helps leaders and creatives apply Stoic principles to overcome challenges. Sponsored By: Shopify - Sign up for a one-dollar-per-month trial period at youngandprofiting.co/shopify Airbnb - Find yourself a co-host at airbnb.com/host Indeed - Get a $75 sponsored job credit at indeed.com/profiting Microsoft Teams - Stop paying for tools. Get everything you need, for free at aka.ms/profiting LinkedIn Marketing Solutions - Get a $100 credit on your next campaign at linkedin.com/profiting Bilt - Start paying rent through Bilt and take advantage of your Neighborhood Benefits™ by going to joinbilt.com/PROFITING. Mercury - Streamline your banking and finances in one place. Learn more at mercury.com/profiting Resources Mentioned: Ryan’s Book, Trust Me, I'm Lying: bit.ly/TrustMeLying Ryan’s Book, Right Thing, Right Now: bit.ly/RightThingNow Ryan’s Podcast, The Daily Stoic: bit.ly/DailyStoicPod Active Deals - youngandprofiting.com/deals Key YAP Links Reviews - ratethispodcast.com/yap Youtube - youtube.com/c/YoungandProfiting LinkedIn - linkedin.com/in/htaha/ Instagram - instagram.com/yapwithhala/ Social + Podcast Services: yapmedia.com Transcripts - youngandprofiting.com/episodes-new Entrepreneurship, Entrepreneurship Podcast, Business, Business Podcast, Self Improvement, Self-Improvement, Personal Development, Starting a Business, Strategy, Investing, Sales, Selling, Psychology, Productivity, Entrepreneurs, AI, Artificial Intelligence, Technology, Marketing, Negotiation, Money, Finance, Side Hustle, Mental Health, Career, Leadership, Mindset, Health, Growth Mindset, Networking, Goal Setting, Strategic Planning, Mindset, Team Building.
Chapter 1: Who is Ryan Holiday and what is his career background?
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'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 Greene. 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
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Chapter 2: How did Robert Greene influence Ryan Holiday's career and writing?
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, like 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, you know, 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 have to say, 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.
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Chapter 3: What was Ryan Holiday's marketing philosophy 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, this 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. 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.
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Chapter 4: How has media manipulation evolved and what concerns does Ryan Holiday have?
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 quick fire 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 Marx'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.
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Chapter 5: What is Stoicism and why is it relevant for modern entrepreneurs?
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. Like 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 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, you know, 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, you know, where are you going? And he says, I'm off to see Sextus 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.
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Chapter 6: What are the three main disciplines of Stoicism and how do they apply to challenges?
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Head over to aka.ms slash profiting today to sign up for free. That's aka.ms slash profiting to sign up today for free. 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, like, 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.
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Chapter 7: How does Stoicism teach us to perceive obstacles and control our emotions?
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 him 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 way, you know, there's other topics that are more straight down the middle. Like 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.
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