“It’s people trying to make sense of the world, trying to find some bearings in a confusing, overwhelming thing called human existence.”
Ryan Holiday is a best-selling author and a student of stoic philosophy. His latest book is Right Thing, Right Now: Good Values. Good Character. Good Deeds.
Motley Fool host Dylan Lewis caught up with Holiday for a conversation about:
- How investors can implement stoic philosophy.
- Why Holiday gave up on marketing spend for his business.
- The cost of getting outside of your comfort zone.
To catch full episodes of all The Motley Fool’s free podcasts, check out our podcast center. To get started investing, check out our quick-start guide to investing in stocks. A full transcript follows the video.
This video was recorded on July 14, 2024.
Ryan Holiday: I think one of the really exciting things about the world that we live in now is how accessible, basic entrepreneurial practices have become. Anyone could throw up a Shopify store and sell things. Anyone could build a platform and talk to an audience. Instead of it being this thing that the elites in Hollywood are doing or the business people in Wall Street are doing, it’s a thing you yourself are doing.
Mary Long: I’m Mary Long, and that’s Ryan Holiday, a best-selling author, business owner, and student of Stoic philosophy. His latest book is Right Thing, Right Now. Good Values. Good character. Good Deeds. My colleague, Dylan Lewis, caught up with Holiday for a conversation about how investors and entrepreneurs can use stoicism in everyday life, Holiday’s realization about advertising spend, and what he’s doing instead, plus why even retail investors should participate in proxy votes.
Dylan Lewis: I think I want to just start out with your overall journey with stoicism and what brought you to it and how you’ve gone through it over the last decade.
Ryan Holiday: I realize in retrospect, there’s a long tradition, this idea of somebody passing on this book and going this worked for me, it might work for you. Which is effectively how stoicism has spread for 2,000 plus years. There’s actually a little note in Marcus Aurelius’ Meditations, the emperor of Rome. He’s thanking his philosophy teacher for passing a loan to him the works of Epictetus. He says, “Thank you for loaning me the copy of Epictetus lectures out of your own library.” That’s what happened for me. I just got past Marcus Aurelius and Epictetus, and I read it, and I was like, where has this been my whole life? This is what philosophy is. We think of philosophy as these abstract questions. We think of philosophy as theoretical. But really, it was that. It’s people trying to make sense of the world, trying to find some bearings in a confusing, overwhelming thing called human existence. That was my interaction with it almost 20 years ago.I wouldn’t say I am a stoic. I would say I am a student of stoicism. I don’t think it’s a thing you arrive at so much as a thing you are trying to understand and to do your best to apply in your own life.
Dylan Lewis: You mentioned that there’s this sense of something that you’re working through, and in the book, you’re focused on justice in particular. That’s the topic that you’re working through in the book you break it down. You have the me, the we and the all with respect to justice. Can you walk me through that micro to macro view?
Ryan Holiday: I’ve been doing now for the last five years this series on the Cardinal virtues. The four virtues of stoicism are courage, self discipline, justice, wisdom, and I did courage, I did discipline, and then this one’s about justice. I think when people think of justice, they think, obviously the legal system, they think about whether something is against the law or not. Obviously, that’s a component of it, but really, justice is the standards we hold ourselves to, the way we treat other people, and then our sense of our obligations to the world, our interconnectedness between all people. The book is a journey through that. First off, what are some standards of behaviors, rules, a code of conduct? How does one think about getting involved, getting engaged? Then finally, what is our sense of the whole? Our connection, our oneness as a species, and then, of course, all living species interconnected in that way. That’s the journey of the book from this really simple, straightforward version of justice to a much more broader and all encompassing justice.
Dylan Lewis: Does that structure in that order reflect your own journey with it?
Ryan Holiday: I think so. I came to stoicism, originally, like, a lot of people thinking about what it could do for me. How it could help me. You could think about it as an investor. At first, it’s how do you become more rational? How do you become more self controlled? Then as you master these basic inward things, then you can take that back out in the world and choose how you’re going to apply that. If you think about these other virtues. Courage and self discipline, of course, these are essential virtues in success in life. But ultimately, to what end is one applying them, to what cause is one applying them. This is where the virtue of justice comes in.
Dylan Lewis: A lot of the examples that you work through in the book are these historical figures that we have the benefit of history playing out and seeing that path that they’ve forged forward. I know, also, though on the micro level, people can read something and say, this is speaking to me into my ideology. What happens when the individual ideology rubber meets the road and interacts with society where other people may say on the other side of something, yes, I also feel like I am on the right path here. I also feel like I’m doing the right thing.
Ryan Holiday: That’s the interesting thing. People have been courageously fighting for causes that we now regard as morally bankrupt for as long as there have been causes, as long as there’s been history. This is the tension, of course, very rarely, as the philosopher say is anyone wrong on purpose. In fact, most of the time, we think we’re doing the right thing. This is where the virtue of wisdom comes in retrospect, sometimes those causes seem like we can empathize, we can see how it made sense. Then in other cases, you’re talking about slavery, something. You can see the profound self serving logic and the leaps that the people had to go through in order to justify or rationalize something to oneself. It’s tricky and what I didn’t set out to do is write a book about a bunch of specific policies per se. But I think this idea of what’s right, this idea of our obligations to each other, this idea of integrity. These are pretty universal ideas that I think we probably agree with more than we disagree with each other. That’s an interesting tendency that we have. When we talk about doing what’s right or doing the right thing, or talk about justice, there is this part of us that I think immediately goes to these exceptions or these really morally complex edge cases, and that’s almost a way of letting ourselves off the hook. Of, like, the pretty basic decisions we can all make day to day that we’re largely in agreement about. But we also make excuses for we let ourselves get away with.
Dylan Lewis: One of the throw lines I notice with a lot of the figures that you profile is this willingness, and sometimes it’s an accident, sometimes it’s very intentional to get outside of their own comfort zone, get outside their own bubble, and having that be something that helps with that internal development, it’s a tough time for that for a lot of people. What’s your advice for someone looking to do that more?
Ryan Holiday: I think how the other half lives, what other people’s experiences are life. What the consequences of this thing that you believe in or that you’ve accepted actually are for other people is such a destabilizing experiences in many ways. This is probably partly why we don’t want to know. If we know, if we see it up close, we don’t have to think about it. One of the an off handed comment in the book that I was blown away by, but I was reading that Steve Jobs actually never visited any of the Apple‘s factories in China. Here you have a guy who’s a notorious micro manager, incredibly detailed oriented, has every opinion you could imagine on how things should be done, where efficiencies could be found, probably not a coincidence that he never hops on a plane and checks it out. Because if he sees it, maybe it’s harder to sleep at night. If he sees it, it’s harder to justify. I think I don’t mean to say this to judge him specifically because here I am holding an iPhone. But we don’t want to know, because we don’t want to have to do what knowing demands of us and what our conscience demands of us once we know.
Dylan Lewis: Yeah, we can’t plead ignorance anymore.
Ryan Holiday: Yes. There’s a reason we try to make it illegal to, for instance, film what happens inside factory farms. It’s the people covering the thing up. In cahoots with us who don’t want to know. We don’t want to know, because if we know, it doesn’t taste so good anymore.
Dylan Lewis: That reminds me a bit of something that comes up in the book, and you talk about this idea that it is not a real principle, a principle that you have not a real principle, unless it costs you money. Unless you have some skin in the game and you begin to feel the impact of a decision that you’ve made, our audience is overwhelmingly an investing audience. We are folks who are thinking about companies and thinking about the ways that we put our money to work. It can mean a bunch of different things. What do you think that looks like as a decision making tenant for investing?
Ryan Holiday: I think one of the really exciting things about the world that we live in now is how accessible basic entrepreneurial practices have become. Anyone could throw up a Shopify store and sell things. Anyone could build a platform and talk to an audience. Instead of it being this thing that the elites in Hollywood are doing or the business people in Wall Street are doing, it’s a thing you yourself are doing. This question of whether Nike should use sweatshops in China, suddenly is a real decision that you have to make when you’re deciding where you’re going to get your T-shirts made that you’re printing on. What I hope from this is not suddenly, you have a bunch of empathy for these CEOs and you go, I see why they do it. What we should take from this is, now my ethics are bumping up into my business decisions. How am I going to square those two? How am I going to get those to fit together? If I’m just an author who sends a digital manuscript to my publisher, and then they send me royalty checks, that’s one version where I don’t have to think about any of this, but I self published a two children’s books a couple of years ago. Then suddenly, I’m going,I can print it in China, and it costs $8 a copy sorry, it costs $3 a copy, or I can print it at this printer in the US. It’s been here for 100 years, and it’s $5 a copy.
Now I have to make that decision. I have to decide whether it’s worth $2 less per unit to me to do something that I wish these other people would do. That’s the question that we all face. We talk about these ideas I wish investors would hold these companies accountable. You are now said investor. You don’t own 20% of the company, but you do have proxy votes. Do you throw that mailer in the trash when it shows up in the post office or from the post office or when you get the email from your brokerage, or do you actually say, I know this probably isn’t going to make a difference, but the principle of it counts, and I’m going to do it or do you say, I don’t like the leadership of this company anymore. I don’t like the direction they’re taking the company both as an investor and as a human being. I’m going to divest myself. I’m actually going to do it. Again, instead of petitioning your university to divest from this or that, what are you doing with your portfolio? This idea that your decisions matter, that your votes matter is a really critical part of this virtue of justice. It’s ceasing to pretend that this is somebody else’s problem.
Dylan Lewis: I want to ask you about one of those as it relates to your own business. I had read a little while back that you’d made the decision to essentially stop advertising.
Ryan Holiday: Yes.
Dylan Lewis: That you had basically taken what was your marketing budget and put it elsewhere. Was that something that was a principle based decision for you?
Ryan Holiday: Yeah. I like a lot of online businesses. You can very effectively and cheaply target people on Facebook and Instagram and all these social platforms. You’re spending money and your primary judgment of whether this is effective or not is whether you’re earning an ROI on SD dollars. You spend $5. Did you make $6 back? This is how you’re thinking about it. One of the things that struck me as the amount of advertising spend was going up every month. Sure, the ROI was going up. But it just hit me. I was like, if I ceased to do this, would anyone notice. I’m spending tens of thousands of dollar a month, and the only difference it’s making is whether it’s directly driving conversions to my business or not. Then I thought, but if I started to spend tens of thousands of dollar a month making stuff. Making articles, making videos, hosting a podcast, etc. If I were to cease at some point, the things that I made would still exist. Even if people and I also thought, if 100 people see this ad, and one person buys it, I’m saying that was an effective ad. Even though 99 people said, this is worthless to me. But what if I write an article and 100 people read it, and then one person becomes a customer as a result? It was still valuable to the 99 people. They just didn’t purchase anything from me. It still had a positive contribution. We could argue how much or how little, but it still was a delivering a value that wasn’t justified or unjustified based on the conversions it generated. We pivoted the business, and I spend basically all the money that I used to spend on advertising, making stuff. I give away so much content, so much stuff. It converts at roughly the same amount, but I’m happy with it. I feel like it’s a service. I know it’s having actual impact on people. It doesn’t just disappear when I stopped doing it.
Dylan Lewis: It sounds like you’ve maybe gone one for one on that decision, or maybe it’s even been a successful shift and you’re seeing more on that spend back, but also that it’s something you would’ve been comfortable doing, maybe even taking a small haircut on because it was more fulfilling.
Ryan Holiday: Yeah, totally. I don’t actually know exactly. The tricky part is it is much harder to measure. It’s harder to measure, but it also it lasts longer. I think in the end, it works out better. But, you’re making a short term trade off. You just think about, you go, the advertising budget of Budweiser is how many billions of dollar a year. What is the lasting significance of said contribution, it’s nothing space. You have all these brilliant minds spending so much time trying to make these things that are, by definitions, interruptions and often misleading or whatever. Again, this isn’t a decision everyone has to make. I’m not saying advertising is immoral. It’s just the decision to say, what is the output of my efforts? How can I best direct those efforts to have ideally additional impact or how can I think about making this as positive of an interaction as everyone involved? I was talking to John Mackey, the founder of Whole Foods once, and he was saying that he just had this decision, this insight one day that his vendors matter too. It wasn’t just like how much money is he making and how much is he saving the customer. But like how is he treating everyone from the animal or the plant that ultimately becomes a product to the supplier to the shipper, and just thinking about, who is involved in this process from having an idea to selling the thing to a customer? Now, obviously, we’re in business to make money. I’m not saying this is a charity. But what are decisions you can make along the way? Some of these decisions are going to cost you money, but oftentimes they’re going to make you money, and maybe it evens out. But how do you make decisions so you can have as much positive impact as possible? How can you also make decisions to minimize negative impact when it’s preventable? That’s just something we all have the power to think about.
Dylan Lewis: I’m curious what your take is on so much of the development and investment we’ve seen in artificial intelligence, particularly because so much of the conversation is around content, and that is where you and your business spend so much time.
Ryan Holiday: It’s interesting watching these companies train themselves on things that I’ve done. Inside all these AI networks is millions of words of writing from people like me, and then spitting it back out at you is a strange surreal experience. Then at the same time this goes to the point, then it’s like, why do you need a drawing made, and I don’t want to pay someone for it. I’ll just use ChatGPT. I’m not immune from this. I think we all understand there are these things that have ethical implications, and then we make short term financial decisions based on what’s easier for us. I don’t know. Right now, when I look at AI, I see it replacing a lot of stuff that wasn’t super good. I think it’ll probably do worse. It’ll be a harder slog to be able to do things at an elite level. But, the law of nature is that eventually everyone and everything becomes replaceable or disrupt it. I guess how one prepares for that is maybe more the virtue of wisdom.
Dylan Lewis: I’m curious how you personally have processed and maybe changed how you process some of these things as the layers of complexity get added on, and you’re trying to maintain the stoic mindset, where you’re going from it’s not just me. It’s, these people I work with, it’s this company that I own and these people whose livelihoods depend on me. What has that looked like for you?
Ryan Holiday: I think this is a reason it’s good to be involved. If you think of philosophy as this thing you do in a classroom or that it’s what tenured academics get to do. Well, then it’s going to be divorced from reality. Do I love that the world seems like it’s falling to pieces? Do I love that there’s these disruptive technological changes that are happening? These macro environmental things happening? No, but I also understanding what the stock say this is an opportunity to actually have the rubber meet the road. The Chinese expression, may you live in interesting times. We live in interesting times. Then it is an opportunity to practice and wrestle with these things. I would love for everything to be easy and for everyone to get along. That’s not the world we live in. Having to deal with that complexity, I think it’s an ongoing challenge. I don’t think I always get it right. But I do try to take a beat and go, I wouldn’t have chosen for it to be this hard, but that it is this hard is an opportunity to apply these things and to really think about them.
Dylan Lewis: I know you’re a pretty big runner. Is that part of the philosophical processing? Is that part of the habit based way of giving yourself that space?
Ryan Holiday: Yeah, definitely. I’m not a big meditator, but I like to get outside, I like to get active, and that’s where I tend to do a good chunk of my thinking. I also think being active, wrestling with the part of you that wants to not do it, and then the part of you that knows it’s good for you to do it. This is also not just philosophical, but it’s practice, the ability to will yourself to do things that are hard. That are expensive in all senses of that word that get you out of your comfort zone? That’s a really important skill to build.
Dylan Lewis: I have the benefit now of talking to you after the book surge and the initial launch. I hope you’re caught up on sleep. I know you’re doing a lot of traveling. But I was following along with some of the book launch fogs. I think early on, you talked about how I think an early reviewer or someone who read the book or something like that had maybe missed the mark on something or felt had maybe misinterpreted some of the points of the book. What do you find that people tend to miss when it comes to the philosophy?
Ryan Holiday: I think stoicism is really easy to stereotype. This has no emotions. This stuffs it all down. This is invulnerable. Then I think sometimes people take my work, and they’ll call it Boicism or something. It’s easy to mock people who are interested in improving themselves. It earnestness is the easiest thing to make fun of. I’ve just learned over the years that’s just going to be a certain percentage of people, and you got to be prepared for, you got to accept it. You got to deal with it. I try to go, was it possible to get nothing but glowing reviews? Of course not. Citizen Kayne doesn’t even have a perfect score on rotten tomatoes. There’s going to be a certain percentage of people that don’t like what you do. This is an idea that Marcus Aurelius actually talks about in Meditations. He goes, like so you met one of those people. You knew there was a percentage of people that were going to be in that camp. Well, this is one of them. Why are you surprised. But there is this part of us that intellectually goes, I’m not for everyone and then we meet someone who’s not for us, and we’re like, what is this? I can’t let this stand. I think I’ve gotten better at just accepting, I’m not for everyone. I know who I’m for. I’m going to do my thing, and I’m going to let the chips fall where they may.
Dylan Lewis: An idea that comes up in the book that I really loved was that you’re better off in a lot of ways, starting out by giving, rather than asking for something. On that note, I’m delighted to be talking to you about your book, but I’m curious, maybe over the last month or two, a book that you’ve really enjoyed that you’ve read.
Ryan Holiday: Great question. I just read this book called the Art Thief. I read it last night. I read it in less than 24 hours. It was so good. It’s about this guy who was basically the greatest art thief of all time. He was basically addicted. He had this almost mystical magical reaction when he would fall in love with a piece of art, and he just, like, had to have it. Almost all art thieves are stealing so they can resell it on the Black Market. He just stole all this art and put it in his bedroom, which was in his mother’s house in his attic.
Dylan Lewis: Is this a true story?
Ryan Holiday: It’s a true story. It’s incredible. It’s one of the best books I’ve read in quite some time. I just thought it was absolutely amazing.
Dylan Lewis: That’s fantastic. There’s the summer reading recommendation, right there. To close us out. This is the third book in a series of four. You mentioned courage, self control. This is justice. Wisdom is next. Can you give us a little preview?
Ryan Holiday: Yeah, wisdom is the one I saved the last because it’s in a way, the hardest one to have any justification for writing. You know what I mean? The last thing you want to do is call yourself wise. I was really thinking about how I was going to write this book. I’ve been working on it now for about a year, about 2/3 of the way done. But I don’t even have a title for it yet. I’m still trying to crack that part of the puzzle. It is the virtue that tells you where all the other virtues are. What’s the right amount of something? What are the causes worth putting yourself out there for? How much courage is too much? How much is not enough. There’s a great working definition of wisdom. Wisdom is knowing what’s what. That’s been the working definition of the book. How do you get a sense of life, get a sense of what to do in every situation? That’s hopefully what the book will help people do.
Dylan Lewis: The book is Right Thing, Right Now. Ryan Holiday, thank you so much for joining us.
Ryan Holiday: Thanks for having me.
Mary Long: As always, people on the program may have interest in the stocks they talk about, and the Motley Fool may have formal recommendations for or against, so don’t buy yourself stocks based solely on what you hear. I’m Mary Long. Thanks for listening. We’ll see you tomorrow.