Young and Profiting with Hala Taha (Entrepreneurship, Sales, Marketing)
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 skills?
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, 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.
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Chapter 3: What was Ryan Holiday's marketing philosophy at American Apparel?
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 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.
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Chapter 4: What are the risks and impacts of media manipulation in marketing?
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Chapter 5: How has media manipulation evolved with social media and AI?
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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 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. Like I 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?
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Chapter 6: What is Stoicism and how does it apply to leadership and entrepreneurship?
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? 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 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.
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Chapter 7: What are the three main disciplines in Stoicism and how can obstacles become opportunities?
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? Like 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 like excited about it. You love it's like turning the have to into get to deciding to 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? Like 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.
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Chapter 8: How does perception shape reality and decision-making in Stoicism?
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.
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 stolen or ego 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.
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