Shopify CEO Tobias Lütke on Building a Better Future

Ryan talks to Shopify CEO and founder Tobias Lütke about his introduction to Stoic philosophy, how Stoicism can be a guide to wealth and power, the importance of builders and entrepreneurs in society, and more. Tobias Lütke is the founder of Shopify, a Canadian e-commerce firm that helps companies set up and run online stores. Lutke grew up in Germany and moved to Canada in 2002. Shopify had 1,000,000 businesses in approximately 175 countries using its platform as of January 2021. This episode is brought to you by LMNT, the maker of electrolyte drink mixes that help you stay active at home, work, the gym, or anywhere else. Electrolytes are a key part of a happy, healthy body. Right now you can receive a free LMNT Sample Pack for only $5 for shipping. To claim this exclusive deal you must go to drinkLMNT.com/dailystoic. Get your FREE Sample Pack now. If you don’t love it, they will refund your $5 no questions asked. This episode is also brought to you by stamps.com, a secure Internet mailing solution to print postage using your computer. Stamps.com allows you to mail and ship anytime, anywhere right from your computer. Use the promo code, STOIC, to get a special offer that includes a 4-week trial PLUS free postage and a digital scale. No long-term commitments or contracts. Just go to Stamps.com, click on the Microphone at the TOP of the homepage and type in STOIC. This episode is also brought to you by FitTrack, the best way to calculate your body’s composition accurately, reliably, and consistently. The Dara Smart Scale syncs with the free FitTrack App so all of your health insights are saved in one place. Go to fittrack.com/stoic to take 50% off your order, plus get an additional 30% off your order with code BUILD30 at checkout. This episode is also brought to you by Scribd, the e-book and audiobook subscription service that includes one million titles. Scribd uses the latest technology with the smartest people to recommend you content that you’re going to love. We’re offering listeners of The Daily Stoic a free 60 day trial. Go to try.scribd.com/stoic for your free trial. That’s try.scribd.com/stoic to get 60 days of Scribd for free.***If you enjoyed this week’s podcast, we’d love for you to leave a review on Apple Podcasts. It helps with our visibility, and the more people listen to the podcast, the more we can invest into it and make it even better. Sign up for the Daily Stoic email: http://DailyStoic.com/signupFollow @DailyStoic:Twitter: https://twitter.com/dailystoicInstagram: https://www.instagram.com/dailystoic/Facebook: http://facebook.com/dailystoicYouTube: https://www.youtube.com/dailystoicFollow Tobias Lutke:Homepage: https://tobi.lutke.com/ Twitter: https://twitter.com/tobi Instagram: https://www.instagram.com/tobi/ See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. 📢 Share | ⚙️ Manage Subscription

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:02Ryan Holiday?

  Welcome to the weekend edition of the Daily Stoic. Each weekday, we bring you a meditation inspired by the ancient Stoics, something that can help you live up to those four Stoic virtues of courage, justice, wisdom, and temperance. And here on the weekend, we take a deeper dive into those same topics. We interview Stoic philosophers. We reflect, we prepare, we think deeply about the challenging issues of our time, and we work through this philosophy in a way that's more possible here when we're not rushing to work or to get the kids to school, when we have the time to think, to go for a walk,

• 0:44Ryan Holiday?

  to sit with our journals, and to prepare for what the future will bring.

• 0:52Ryan Holiday?

  I wanted to talk to you today. Hey, it's Ryan Holiday. Welcome to another episode of the Daily Stoic Podcast. I'm so excited about today's guest because, as I tell him in the interview, I'm not sure I would be doing this show without him. My guest today is not so much an intellectual influence on the show, although he's a brilliant man, and I've been aware of his work for a long time. His influence is much more practical because my guest today, Toby Lutka, is the founder of Shopify. Shopify is sort of the backend of almost all e-commerce on the internet these days. And it is like so many great products or inventions, something that allows people to unleash their creativity and productivity.

• 1:35Ryan Holiday?

  It powers the backend of the Daily Stoic store, for example, and countless other retailers and craftspeople and artists and authors, who, again, you probably weren't even aware you were checking out through Shopify, but you were. Toby, as it happens, is a lifelong student of the Stoics, super familiar with them, and we go way in-depth together about the Stoics, about how to remain Stoic inside success, how to operate by a moral code, if you will, how to deal with the obligation, in his case, of wealth and...

• 2:10Ryan Holiday?

  And influence and how to live a philosophical life. And so I'm really happy with this interview. We also talk about something, we talk about commerce. I don't think it's a coincidence that that Zeno founds the stoic in the Athenian agora. The Stoics were business people. Zeno himself was a business person. Seneca was an artist. The Stoics were not sort of removed from the realities of economics. They were familiar with them. They were aware of them and they believed, well, whatever you do, you should do right. You should do ethically. You should also do the best of your abilities. And that's why I know this intro is probably sounding a little bit like an ad, but Shopify really has helped me do that. And it's been a great platform for us here at Daily Stoic.

• 2:54Ryan Holiday?

  And I'm just fascinated with anyone who builds something that is then used by millions and millions, not just of people, but millions and millions of businesses. It has enormous reach. And again, it's powering the backend of the internet in a lot of ways. And that's another thing that Toby and I talk about. We talk about what it means to build something, to make something. And to make something that ideally makes the world a better place. That's what we're trying to do as Stoics. That's what we're trying to do as human beings. So I think you're really going to like this interview. It's one of my favorites. You could check out Shopify if you like, if you are thinking about opening a business, retail or online, Shopify might be for you. You can also follow Toby at at T O B I on Twitter.

• 3:37Ryan Holiday?

  He's got some great stuff there and enjoy this interview. And I hope you go out and build something.

• 3:46Ryan Holiday?

  I suggested we do the podcast just because sometimes when you, when you meet someone, you hop on the phone, you get like 10 minutes. But a podcast seems to be a level of, of depth that we don't get in most ordinary conversations these days.

• 4:00Speaker 01

  It's true, isn't it? I love a podcast format. It's funny because I. I grew up in Germany, like a little town. And I was like, I mean, I'm an engineer, I was really into computers, but didn't know how many people were into computers. So I

• 4:18Speaker 01

  I ended up like building like an entire skill set for almost like figuring out how I can be a fly on a wall in conversations that like experts had amongst each other about topics I care about. You know what I mean? Like so I remember vividly, like I was subscribed to like the Linux kernel maintenance. I didn't, I didn't understand a word they were saying, but I was looking up like all the terms and eventually built up and not much understanding what they were talking about to sort of understand how they're thinking of the problems. That was hugely impactful. And I always felt that

• 4:53Speaker 01

  being a fly on a wall is like, it like this somehow stuck with me and I wanted to build this as a skill. But now, you know, podcasts are bad, right? Like it's the best thing. I honestly think if I would time travel back to my teenage years and explain sort of the incredible environment of technology and all the things we have and like phones would look like magical devices, but I think podcasts would be most impressive to my teenage year.

• 5:23Ryan Holiday?

  Yeah, no, it's incredible that you can get like, if you think about like, and we'll nerd out about philosophy, you think about someone like Socrates, right? We have these dialogues that survive to us, these like little snippets of conversations. And we were clearly so starved for that kind of conversation for thousands of years that they survived. And now there's like hundreds or millions of hours of podcasts recorded every day and of sometimes of the smartest or most successful people in the world, just, just talking about stuff.

• 5:52Speaker 01

  Yeah. And I, you're exactly right. It's like, it's almost like as if everyone kind of missed why

• 6:01Speaker 01

  you know, Plato's writings were so meaningful and you know, also of course Aurelius's diary, because they're, they're kind of

• 6:12Speaker 01

  They give him insight into something that you, like even if you would know the people, you could actually not have gotten this because this is like, if they're private to the, like in our case, in these conversations, I think that's, that's actually profound. Like it's, and I think we now only observe how valuable this was through the medium of podcasts. Because I can tell you, the moment like COVID started, like almost a year ago, the first thing I did is I went finding podcasts where experts on virology and epidemiology talk amongst each other to figure out how to, how they're thinking about this. And that ended up being very, very meaningful.

• 6:55Ryan Holiday?

  Well, as someone who's, who's obviously built what you've built, I imagine you, you spend a lot of time sort of thinking about the economics or the, the sort of the incentives of the medium. I think the other thing podcasts have going for them is that they're the least viral of all the, all the forms of social media. And so there's, there's less clickbait in them and they're not like, you know, Twitter is great, but there's the, the constraint that it can only be 280 characters obviously selects out a lot of nuance. And I think, you know, an hour conversation or a two hour conversation, some of these three hour podcasts, you get into a level of granularity and you're not thinking about, will this spread well? You're just thinking about like, is this interesting or not?

• 7:37Speaker 01

  Exactly. And it's, it's, but like, and another thing is like, like a conversation is also like, again, it's really something that's been created by two, two people. The follow up on questions that the person you're, you're observing or listening to will ask are very different from the questions you would have asked. And sometimes there's actually significant learning in that. Like, because if then the conversation goes into an interesting space, you realize I wouldn't have steered it there, but I appreciate that it did go there. And I think that's just so much circumstantial learning around this, which is all really, really, really important.

• 8:20Speaker 01

  On this other side of Twitter, it's like there's a lot more. It's very, very hard to communicate anything that's beyond any kind of nuance, of course. Well, I mean, I think a lot of people are sharing this opinion. Additionally, the media almost encourages that if you attempt to communicate anything that requires more than 240 characters, that every particular instance in tweet ends up getting individually judged through the media of retweets. And so you have to make very sure that there's no bad faith arc that someone can construct with 18 posts in a series of them. And I don't tend to think that's terribly good for psyche.

• 9:04Ryan Holiday?

  Well, speaking of follow-ups, what small town are you from in Germany?

• 9:08Speaker 01

  So a town called Koblenz. It's actually, like, it's no town. It's right there, two rivers in Germany get together, the Mosel and the Rhine. And it's, I mean, it's about, I think, 80,000 people live there, so it's not that small. And Germany's fairly dense in general.

• 9:29Speaker 01

  But one thing that I remember well was, growing up, it was celebrating its 2,000 anniversary because it was a Roman fort.

• 9:38Ryan Holiday?

  Wow.

• 9:39Speaker 01

  And during Caesar's campaigns. And so that's kind of cool. Like, I immigrated to Canada later, and one of the adjustments I had to go through was that I saw these businesses, or like, I think, cars drive around, but they're advertising some businesses, and it said things like, "Since some date within the last, like, 15 years ago or so."

• 10:05Ryan Holiday?

  Yeah.

• 10:06Speaker 01

  And you come from a city that is 2,000 years old, and the place I ordered my pizza from was like 300 years old. So it's like, you may didn't even put "since" that because that's too recent.

• 10:18Ryan Holiday?

  Yeah, my office was built in 1880, and that's like really old by American standards.

• 10:23Speaker 01

  Yeah, exactly, exactly. So the standards are different. So Europeans tend to think that 100 kilometers is far, and North Americans think that 100 years is old.

• 10:32Ryan Holiday?

  Right.

• 10:33Speaker 01

  And so the cultural differences are a fun tool, so.

• 10:37Ryan Holiday?

  My grandmother's from Rehensberg. She came here when she was 16 or 17.

• 10:42Speaker 01

  All right, cool.

• 10:43Ryan Holiday?

  So what, so talk to me about your introduction to Stoicism. When, when does that happen? Was it, was it because you grew up in a town that was a Roman fort? Or does it come later?

• 10:53Speaker 01

  I don't, no, I don't. It's a good question. I, um, I mean, again, culture does something, um, and usually more than people imagine, um, to, to, to, to places. Um, uh, like I, I went to a school that, um, uh, like it's called a classical language school. What that means is, um, you're done with elementary school. You go fourth grade. I, I guess you're done with fourth grade, so you're fifth grade. And then, uh, the first additional language that you're introduced to is Latin. Um, and, uh, I, I, I'd say that this, this sort of bent sort of sideways for me. I, I, I didn't terribly appreciate this because I was fairly eager to get, to get to learn English. Um, uh, just for computing purposes. Uh, most of the things that I care about are fully translated.

• 11:39Speaker 01

  Um, uh, however, um, the nice thing is you end up like, there's not that much content. Like they, they start you on like Latin translated Asterix Nobelix. But, um, you get very quickly, you run out of things and, uh, then you end up reading Cicero. Um, and, uh, you know, some, some of the good parts and fun parts of, of, of his particular operations. And, um, that wasn't, ended up being too memorable, but like he ended up speaking quite a bit about Cato. So this is, um, uh, like, uh, you, you, you can absolutely see that Cicero had significant, um, reverence for, for, for, for Cato, even though they ended up as rivals, um, relatively often. And, um, so, so it was a way of a general, uh, like idea.

• 12:21Speaker 01

  Then, um, uh, I, the, the, the next thing then you, you get English, uh, seventh grade. You get, uh, uh, third language afterwards, but you get to choose either French or, um, uh, ancient Greek. Um, I was trying to figure out which one to pick, uh, on, uh, like of those things. And talked with a friend of mine who was a couple of classes ahead of me. And he said, the real advantage about ancient Greek is that you actually get to read the stuff that Romans actually like meant, instead of just sort of what they recorded. And he pointed me at Marcus Aurelius. I ended up like, there was a lot of quotes from him, like sort of a part of a textbook. So I was aware.

• 13:06Speaker 01

  And then later in life, I got a copy of Meditations and it's probably my most read book. So I find it profound.

• 13:18Ryan Holiday?

  Yeah, it's strange. Like when you learn Spanish in the U S, it's like dande estala biblioteca, right? It's like all these sort of nonsense, sort of pedantic sentences. And then when people learn Latin, which I was not taught, you know, you're like reciting the orations of Cicero or the epigrams of Seneca. There's this, there's this weight to what you're learning. So you're learning a language, but you're also learning the sort of common language of Western philosophy at the same time.

• 13:46Speaker 01

  Yeah, so goes with theory. I think the thing of Latin is, Latin is one of us. I think like teaching Latin first is an idea that makes a lot of sense to parents. And like it's sort of in theory, the theory is just like praxis. And praxis, praxis is nothing like theory, right? So I don't think it's a particularly good idea to do this, especially in this day and age where English is such a tendency for also reasons. But yeah, it is a root. It's a root language and it is neat at times to be able to like spot commonalities. And there's an advantage to like, creativity always comes from constraints, like Latin is constrained language. People are sort of attempting to figure out how to say words like airplane in Latin,

• 14:31Speaker 01

  but there's not really no way to talk about airplanes in Latin. So the constraint itself means you better talk about things that happened during, you know, let's be, let's be honest, probably one of the top three most interesting periods in at least Western human history, that's the time of a Roman Republic, end of Roman Republic, which just politically it's fascinating.

• 15:00Speaker 01

  Yeah, and I mean, which is sort of lost, unfortunately, on like seven years.

• 15:06Ryan Holiday?

  But do you think about that with with your kids? Like, to me, it's like, yeah, it's probably ridiculous or sort of antiquated fantasy to teach your kids Latin. But the idea of like, using language to teach them things that really matter is something I'm thinking about. So it's like, instead of reading these silly stories about pizza, or, you know, whatever, whatever most kids books are, we've tried to focus on sort of some of the Roman and Greek myths, whether it's Cincinnatus, or, or the 300 Spartans. These are stories that are still really interesting, but inside the simplicity, there's also actually some sort of cultural significance or moral weight to what you're talking about.

• 15:47Speaker 01

  And I think that's the role of these stories to begin, right? Like, they, they, they, they meant, like, they, they're sort of,

• 15:56Speaker 01

  they, they, they survived through time on merit of them playing multiple roles, like entertainment, but also,

• 16:07Speaker 01

  you know, every story you will ever encounter changes you in some significant way, if it's any good, right? And these are the stories that are carried by successful cultures. And so I totally agree. I talk a lot with my kids about

• 16:26Speaker 01

  the lives of philosophers, as I understand them, and try to paint the context of the worlds they lived in, which I think going through the avenue of language is, is a valid way, but I don't think it's the optimal way. I, I, I think it's, you, you, I think you end up doing too many things at the same time. You're trying to like, learn what an uplet is, and, and, and, and while also trying to sort of then get into like some kind of appreciation for, for, for, for really remarkable time.

• 16:59Speaker 01

  And a lot of names that you have to remember. That's all hard things to do. So, so I tend to think it's better to just concentrate on one subject. But it's, it's, it's something I, like, these are some of the best stories. I mean, one thing I certainly reoccur in my life is like, whenever I think I encounter a really, really good idea, I realize clearly that some, some, some Greek philosopher two or three years ago already had it.

• 17:20Ryan Holiday?

  Sure.

• 17:22Ryan Holiday?

  Got a quick message from one of our sponsors, and then we'll get right back to the show. Stay tuned.

• 17:28Ryan Holiday?

  Yeah. So how do you think about Marcus Aurelius as a CEO? I mean, I think what's so fascinating about Meditations is that you have the private thoughts of like, almost every other text from every other leader that survives to us in history comes through what you were talking about earlier, which is the sort of the view towards publication. Right? So you have the sort of leader performing when they put out their memoirs or they give their speech or whatever. What's so fascinating to me about Meditations is that it's really the most powerful man in the world writing to himself about how to be better. And he probably, he'd probably be mortified that we're reading it.

• 18:09Speaker 01

  Yes, especially because he basically, when he talks to himself in his Meditations, he's very clear about not being, like, he's selling himself on not being relevant, but that's okay.

• 18:25Ryan Holiday?

  Yes, right.

• 18:26Speaker 01

  After he's dead, which, you know, failed spectacularly.

• 18:31Speaker 01

  And I, yeah, I mean,

• 18:36Speaker 01

  I think the document is incredible in its intimacy, but like, it doesn't live outside of the context it was created in. The point is that I don't think at any other period of history, like, we have never had, again, anyone as powerful as a Roman Empire was. Like, it just, it's

• 18:57Ryan Holiday?

  Sure.

• 18:58Speaker 01

  Like, may, like, people may go to Genghis Khan, but like, it's, it's, it's, it's even that's very different against very different context.

• 19:06Ryan Holiday?

  There wasn't the same centralized power there.

• 19:08Speaker 01

  Right, exactly. And so, so you really, it's, it's hard for us to fathom just how absolutely total the power of a Roman Empire appears were.

• 19:23Speaker 01

  For him having left his life the way he did, it's just, it's, it's a proof point that,

• 19:32Speaker 01

  you know, while directionally important, there's a lot of sentences, like, there's actually a lot of cultural goods that are around that power crops and so on. I don't believe so. I think it reveals. And Aurelius is like, probably the best person to point at again, because he didn't like mean to be published or get anyone to change their opinion about him. It's just plain, like, that he managed to resist all, like, he had all the demons. He just managed to control them and therefore

• 20:12Speaker 01

  that creates a watermark, a high watermark, I think, which just like tells me that like, whenever I worry about these things, like, I know it's possible. And if it's possible, I can do it. I can hold myself to.

• 20:26Ryan Holiday?

  Which he says in Meditations. He says, if it's humanly possible, let yourself know that you're capable of doing it. And you're right, that you have someone who had way more power than any of us could fathom. It should make it clear to us that you can become powerful in your own way and not be corrupted by it.

• 20:45Speaker 01

  Yeah, there would have been zero consequences for him of acting out anything. And

• 20:53Speaker 01

  if that's like this, a lot of

• 20:58Speaker 01

  moral philosophy is based on, or at least a lot of people would subscribe to the view that under such circumstances, it is not possible to live a fully vicious life. And, you know, okay, so like, it's hard to talk in absolutes. I'm sure he didn't live up to his own standards

• 21:16Speaker 01

  permanently. But the fact that he.

• 21:20Speaker 01

  Of what we know, he performed incredibly well there. And so, to me, this is extremely meaningful. I love just opening the book and just going a couple of points forward. And in it, I always find something that somehow like magically ends up being relevant in some way for something I'm wrestling with. And so it's a great comfort to me.

• 21:43Ryan Holiday?

  Yeah, right, right before the pandemic, I gave a talk in Budapest. And so, and, and, and so I went to Aquinum, which is the Roman camp where Marcus spent some time, they think he wrote a decent chunk of meditations there. And I was walking through this sort of museum, there's no one there. And they had this large statue and it's, it's your typical sort of Roman sort of chest to neck bust, but there was no head on it. And at first, they thought that it had just been the statue of an emperor, then the head had fallen off. Then they were looking at the neck and they realized that actually, there was no head on purpose, that, that the Roman emperor was worshipped as a god in his own time.

• 22:26Ryan Holiday?

  And so they made, this is what they had there, it was a, a statue at, for the cult of the emperor. So what I, I was fascinated in this in two ways. So on the one hand, okay, so Marcus is literally being worshipped as a god in his own life. On the other hand, he must have known that as soon as he died, they would remove his head and put the head of the next emperor. So it was, it was designed to have a replaceable head, this statue. And, and to me, that sort of perfectly captures Marcus and Stoicism and, and the things that he's talking about in meditations, which is like, sure, you're very powerful right now, and you can't let that corrupt you and you have to be good.

• 23:08Ryan Holiday?

  And you also have to understand that soon enough, you will be dead and none of this will matter and no one will remember you and they'll move right on to the next guy.

• 23:17Speaker 01

  You know what, I just, obviously, I don't know Marcus. I, I am just trying to, I have a mental, I, I tried to build a mental model about him and I had better consolidate considerations. It would tell me, he would probably love that. Like, he would, he would love the fact that, of course, interchangeable heads, but, and, and because that, to him, it would be in perfect harmony of the way he likes to structure his thoughts and his value system. Now Nero, we're probably not okay with that. So.

• 23:48Ryan Holiday?

  Well, to go to your point about power revealing, I think it's actually Marcus and Nero illustrate that well. So, you know, Marcus is, his father's not emperor. Nero, actually, his father is not emperor, right? They're both adopted. They both are introduced to philosophy in their late teens, early twenties. They both have the best philosophy teachers in the world. Nero gets, Nero actually has an advantage, right? Nero has Seneca as his teacher. Marcus has Junius Rusticus and Fronto and a few others. But that they would go in such radically different directions with essentially the same job and the same inputs and the same advantages, I think makes you realize that it's,

• 24:32Ryan Holiday?

  it's, we almost have a fatalism about the idea that power corrupts. It's like, we refuse to accept that that people have any agency, that you can choose to be good.

• 24:44Speaker 01

  Yeah, absolutely. I, I, I think character is incredibly power dependent, though. And I think situations like this illustrate it. Now, corruption through power like might have a higher batting average. I think that's, it's easier to come by examples like of this, but I, yeah, again, I think it's, I think it's profound what he's, what he represents. I mean, I don't, I can't think of another philosopher king in sort of a platonic ideal. I mean, obviously, he didn't wholly adhere to this, but I don't know. Can you think of other people who would, who might take this title?

• 25:29Ryan Holiday?

  So, so the only one that comes close is Cyrus the Great. And obviously, you know, that's in the Eastern model, not in the Western model. But Cyrus, and Xenophon writes about Cyrus almost as admirably as he writes about Socrates. So there's something in Cyrus, I think. But the other thing that's interesting to me is both Cyrus and Marcus end up having terrible children, which has always been an interesting historical puzzle to me.

• 25:59Speaker 01

  I mean, Marcus, I had a lot of his children died, right? Which is also again, adds to the story. I don't know how many it was, but he went clearly through enormous hardships along.

• 26:08Ryan Holiday?

  Well, one would be too many, right? Imagine that we're like, we're not even sure how many children he lost. It's but it's it's more than five. And you're just like, I think that's also interesting to me. And that's been more my reading of Marcus lately is, you know, I understood it as power. I understood it as difficulty, understood as stress. And then in the last year, it's like, now that I have kids and then also living through a pandemic, you're just like, wow, he was writing this during the Antonine Plague. He was writing this in the aftermath of burying a child and then another child and another child. Just the sheer inhuman stress that this this person must have been under. It's almost incomprehensible.

• 26:51Speaker 01

  Yeah, it's true. I mean, it really does. I mean, the current times are nothing like those times, but the parallels are like they're there. And as I relate to like people's psychology, I think you can you can sort of find yourself in the people who live through these tough times. It's certainly been a very challenging time psychologically. We all know this, like, I think I think this is what I love so much about. Actually, I really appreciate your work because I think you're making a lot of this world a lot more accessible, which is important.

• 27:27Speaker 01

  And I, what I personally love so much is like thinking back into Roman, like Greek times around this, this sort of five year stretch, like the incompleteness of their religion and the benefits of that, you know, in a really roundabout way, right? Like the, you know, obviously Zeus and Apollo and everyone, they didn't, I mean, they sort of cared. I think people sort of cared if I cared, but no one really really thought they cared. And if they, depending on how they, in what way they believed in them. So they also, they're terrible role models and everyone got that.

• 28:07Speaker 01

  So like people had to kind of build their own life philosophy in a very meaningful way. And there was actually a catalog of life loss to choose from, Stoicism being one of them. And I think, I think a lot, like, we don't quite acknowledge it, but we really are feel like a little bit back in such times, aren't we? And, and, but we don't have the culture of open dialogue around that people need to find themselves a life philosophy, kind of, find themselves.

• 28:38Ryan Holiday?

  I, I totally agree. There's a, there's a Flaubert quote, which the timeline is totally wrong. Like, it's, it's like one of those quotes where it's like, every part of the quote is incorrect, but it's still true. He says, "Between Cicero and Marcus Aurelius," he said, "when the gods had ceased to be and Christ had not yet come," he said, "man stood alone in the universe." And there is kind of this period where the old, the old Roman sort of polytheistic system had lost all but its most symbolic meaning, and Christianity wasn't ascendant, that, yeah, you have Cicero and Cato and Marcus Aurelius and Seneca, and, and, and they're just, they're

• 29:20Ryan Holiday?

  trying to figure out, what do you live by, what's important, what are the rules, what, how do you find the meaning in life? And they choose to do it philosophically, which is so interesting. And I, I do think we're in an analogous time where, you know, religious faith is plummeting, faith in institutions, faith in, in, even, even in, in countries, or, you know, GMOs, NGOs, all these things are sort of falling away, and people are sort of going, well, what do I live by? And that, that, that question is relevant again.

• 29:54Speaker 01

  Yeah, absolutely. I, I, I think the, and, and it's, it's a vacuum that wants to be filled. It's very meaningful. And it's, it's not quite apparent that we're doing a good job, like, making, like, making the teachers available once the students are ready. And the world sort of at, at large right now, there's, in fact, I think, there's a lot of people misdirecting these desires into, into some zero-sum pursuits and other, and other games at times.

• 30:28Speaker 01

  And I, I think that, I mean, I think that's sad. I, I, I mean, it's, it's, like, again, has to be a little bit fatalistic about it, but like, some of this just exists because, I, I think, modern philosophy, although I don't know a lot about modern philosophy, and if I try to find an avenue into it for any meaningful way. I I I just I just find it's like it's it's so metaphysical and so irrelevant um that I I just like the entire concept of philosophy, it's actually it's actually very hard. If you go, if you we don't have parties anymore these times, but once we will have them, and you go around saying, hey, I'm really interested in philosophy. I don't like, you may wind up having a really good conversation with someone in a corner,

• 31:12Speaker 01

  but you're not going to be part of a main discourse of a party, no matter what. Maybe that's something about the party cycle too.

• 31:20Ryan Holiday?

  No, no, I think-

• 31:20Speaker 01

  Understanding of parties, for that matter, but I I just, I think that's sad, because this philosophy is kind of, it's such a big part of uh uh.

• 31:29Ryan Holiday?

  Like- What's the whole thing? I mean, you know, Cicero says to philosophize is to learn how to die. This is how you find meaning. I I think it's your your your point is well made about it being a vacuum, because it it is a vacuum that wants to be filled, but the sort of weird irony is a lot of people fill it with cynicism or nihilism. And I think that that explains a lot of what's happening in the world. It's like, sure, you you absolutely do have to to to question the past and you have to tear down a lot of these broken systems. But if you replace it with nothing, where does that, where does that leave you? Not sure it's better.

• 32:06Speaker 01

  Yeah, this is like for for destroying things or criticizing things, you don't, you like, it's easy to create a coalition of people and point at something and saying this is imperfect. The the like, I um um from a personal philosophical perspective, I I I really, really value building. I I know it sounds extremely basic, but it's actually probably a much more complex and interesting topic than most people realize, like uh building and creating things or helping other people build things. It's it's kind of and ever humanity has its really high moments, like whenever we get to the moon or like we

• 32:43Speaker 01

  created vaccine uh in the nick of time, or the uh there's incredible infrastructure that makes the water good.

• 32:51Speaker 01

  Always to great sites. That was when people were building. They had the critics too, and the critics might have caused them to build even greater. But like, there's supremacy to creating things. And I think modernity has lost this a little bit. I don't, I don't think we put the cynics and the critics sometimes on higher, in higher regard, but in higher regard than the people who are actually out in the arena and build things. And I think that's, I, I, I think we lose a little bit if this keeps going. And my, my hope is that one of the rebounds of COVID, and I'm being intentionally optimistic here,

• 33:33Speaker 01

  might be that people will understand that, yes, we built the Golden Gate Bridge in what, four years? And then we made it to moment ten. And this, this all sounds like things that happened very long ago. But we also built up a stack of technology to the point that when we needed to be ready, we could, Moderna could create a vaccine in two days.

• 33:57Ryan Holiday?

  Yeah.

• 33:58Speaker 01

  Even probably three years earlier, we couldn't have. Five years, definitely, just because it didn't have the DNA sequencing capabilities. So it's, it's, it's like, like, we still can build really fast when we apply our cells.

• 34:13Ryan Holiday?

  I'm glad you bring this up because there's sort of this stereotype of the Stoic. And Marcus talks a lot about the perils of ambition. And there's sort of a passivity to Stoicism. Epictetus talks about the art of acquiescence. And I think this is all, this all actually is essential because anyone who has ambitious, has ambition, knows that it's a double edged sword. But I always sort of point people to, people who think the Stoics were passive. I go, but sure, look at the list of accomplishments of the Stoics. I mean, Seneca, in his spare time, became one of the greatest playwrights of all, in, in all of human history.

• 34:52Ryan Holiday?

  You know, Marcus Aurelius, you know, when he, he, he leads the Roman army, he, the, the, the Stoics did things.

• 35:00Speaker 01

  Yeah.

• 35:00Ryan Holiday?

  And and they and and I mean, even, you know, the founding fathers of America were inspired by Stoicism. There is a long history of Stoics going out and building things, starting new things. It's not just about sort of passively or or deterministically defending what already exists. But but there is an element of, you know, this Stoic virtue of courage. It takes courage to go out and build and make new things. And I, to me, that's an integral part of the philosophy.

• 35:26Speaker 01

  And I think part of the philosophy is extremely beneficial to the builder mindset. Like, I mean, um, to me, one of the most core concepts of, I think, but all the stories that I have seen circle around and and some of them go more in depth is is, um, I find Alfred Adler puts it the best in in in like the separation of tasks, which is clearly sort of a revision of this. And they're just like, what is like, what I'm there for? I think I think Aurelius writes about, you know, victory is for making things.

• 36:06Ryan Holiday?

  Yeah.

• 36:07Speaker 01

  And what that means to him is like, he happens to be the Roman emperor. And and that is the the task. And he has to like do it better than anyone, like he or not even he does not even better than anyone. He does it to the best of his abilities and nothing less should be acceptable because he is like a victory of of of of of emperors. And so there's a grounding that you get by by just accepting the task that that that life has assigned to you at this point of time. That I think reorients you to be sit in comfort with your own standards, which is, I think, super important.

• 36:48Speaker 01

  So much, I think, of the value system that we inherit through, like, in, you know, in in the West, where we have a very Christian culture. And that generally modernity encourages is to give enormous amount of weight to what other people think.

• 37:09Speaker 01

  And and I. Like, obviously, this is one of us kind of things like, like, humans would not have evolved to, to what they did if they wouldn't care what other people think. Like, there is, like, social cohesion, tribalism, like, all these things couldn't have emerged. If, um, we wouldn't give some kind of primacy to, um, not displeasing everyone else in the, in, in the group and whatnot. Um, so, so I, I, I know it's, it's fairly innate, but like, being able to, to, to, to, to not just have that particular sort of, uh, energy center in the brain directly connected to the way we behave, but rather have it run through some kind of, uh, transform pipeline where you can check, uh, is this actually valuable right now?

• 37:53Speaker 01

  Uh, is, is what I think stories doesn't teach us. And I, I think it allows you to go and create things. Um, because again, um, you, like, people will build now they are builders. People will make now they, they have to make. Um, the people will make know that they will find criticism and that a lot of people salary in the world are, are paid by, um, uh, them criticizing the works of the people who built, uh, and where we are right now. Um, and that does require courage, right? And it does require, um, um,

• 38:26Speaker 01

  like, it, it's, it's, this is something so simple. It's, it's the simplest thing in the world, but it's actually, I, I, I, I find it profound and tend to, uh, mention it a lot. Um, if you want to do something that's better than what exists, it's axiomatic that you have to make something different. Like, and, and obviously this is true, because if you make the same, you get the same. Right. But the implication of this is massive, because if, if you're trying to create something that is, like, you probably want to improve things. So you can't, like, they will, they will, in, in a moment, you decide to create something that should be better. You have two choices. Um, lean into the, the fear of creating something that will be ridiculed, or you create the same thing. And, and it just, um, that's.

• 39:11Speaker 01

  Not everyone wants to embark on this. I see this like every day because Shopify enables so much entrepreneurship and that's ultimatum of like putting yourself out there. So it's hugely inspiring to see people do this all the time. But I can tell you, everyone, like there's a demon of you're not good enough in the back of everyone's minds.

• 39:32Ryan Holiday?

  Yeah, Marcus says, you know, we value ourselves more than other people. And yet, for some strange reason, we value their opinions more than our own. And so you have to have this sort of courage of like, I think this is a good idea. I'm going to go do it. And I'm going to proceed even if other people are saying there's no value in it. Maybe the way to think about the sort of Stoicism and the builder mindset is like, if you're not a builder, Stoicism probably won't make you a builder. But if you are a builder, Stoicism is a really good tool to have in your toolkit, because I think the other side of ambition can be ego, or selfishness,

• 40:16Ryan Holiday?

  or arrogance, or delusions. And I think like Marcus Aurelius, you know, wanted to do great things, Seneca wanted to do great things. And you almost need Stoicism as the counterbalance, or the principle, the core first principles that help you sort of stay sane and rational as you're trying to go do an irrational thing, because building is irrational.

• 40:43Speaker 01

  Right. And it's, building is a roller coaster. And you're often going to be, you know, you build books, you know this very, very well. And you will sometimes think this book you're writing is going to be your best. And then like potentially 20 minutes later, it's the project is doomed and it's going nowhere, right? Like, and against this sort of oscillation,

• 41:13Speaker 01

  the concept of setbacks, criticism, dislike, all these things, they will hit you at different parts of this particular roller coaster. And it's not like...

• 41:23Speaker 01

  It's your ability to resist giving primacy to this at your lowest points that really determines if you can participate to create this. And so, again, what I really, really love about the philosophy and the conception is so much about,

• 41:43Speaker 01

  there are so many tools that clearly, like Aurelius has, and the office described, epic data specifically, where it's just, your job is to just be a builder. Like, you should make yourself worthy of support by other people in your end of a building. And ideally, you should live a life in such a way that you're worthy of people, you know, liking you, and you're pleasant and hopefully good for, all these things are desirable things. And it's your job to adhere to your own standards. It's not your job to get someone else to like you.

• 42:25Ryan Holiday?

  That's sure.

• 42:25Speaker 01

  It's actually their job. And it's their job to like you because you are likeable person. I find that, like, I need, this is the thing I keep needing to remind myself at the low points, when like, something hits from someone I, who somehow managed to get past my auto defenses, and I have to try to reclassify the bit of feedback into the context it was given in and whatnot.

• 42:53Speaker 01

  And I just, again, I find, I keep coming back to these concepts.

• 43:00Ryan Holiday?

  Got a quick message from one of our sponsors, and then we'll get right back to the show. Stay tuned.

• 43:06Ryan Holiday?

  When I've been signing books lately, the quote I've been doing is from loosely adapted from Marcus Aurelius, he says, "Fight to be the person that philosophy wants you to be." And I was curious, like, so Marcus is interesting because there's lots of bad emperors, and then he's one of the few examples of a good emperor. When I, when I look at the club you're a member of, the sort of billionaire founder club, there's, there's a lot of them that, you know, built amazing things and contributed very positively to society. And then sort of undoubtedly, there's some not so good ones, certainly historically so, right? The, the sort of captains of industry haven't always been the best people. And I wonder how much of that is, you know, who they were, and then how much of that

• 43:50Ryan Holiday?

  was a sort of corruption of power and wealth? How, as you've gone and become successful, have you thought about sort of staying true to what you believe and the kind of person you want to be when, when you have unlimited temptation or opportunities and are probably somewhat immune to a lot of consequences?

• 44:10Speaker 01

  Yeah, I mean, my, I'm, I mean, my, my, my book's still being written. So, so, I, again, I, I, I love, you know, what I love about the quote you choose there is because it shows, this is basically philosophy, so it should be even on topic. Have you read, like, or some of the other, David, James Castle's book, Finite and Infinite Games?

• 44:36Ryan Holiday?

  Yes, yes.

• 44:37Speaker 01

  Yeah. I, I find that a profound contribution of an almost elementary concept to, to, to, to, to sort of the toolset of philosophy that I, I, I like to invoke when I'm trying to solve problems. Maybe it's because where I came, like, I came in his book, I came across the concept the first time, but, and, and I'm sure someone in Athens probably thought of some language related to this two or three years ago.

• 45:04Ryan Holiday?

  Yeah.

• 45:05Speaker 01

  But, but, but the, the basic concept there is like, what a, the quote you mentioned, live a life that philosophy wants you to live, or is, is an infinite game, right? It's, it's, it's, this is not, like, it's not winnable. Like, for something to be a winnable game, there needs to be a goal, and a, a, a final game, there needs to be a goal and rules and boundaries, like tennis is a finite game. Internet games have no goals and their journeys, they, they, you can't, you can't even know how to continue. It's just, you, you need to build a, like, like some kind of guide stone, north star for yourself and, and, and just see where it goes. Like, but there's never a goal to reach your horizon.

• 45:45Speaker 01

  The, the, the, the only potential step you can take is to reach your horizon just to gain more vision towards the, the, the infinite games that you actually play. And so like, obviously startups are a fantastic example of internet games and, and almost all instances.

• 46:03Speaker 01

  I think what helps a lot is to understand the internet games that you wanna play. Like, and, and, and then choose the finite games that you are willing to join based only on the ones which amount to some kind of advance in the internet games. And so, um, because there is a lot of distractions, there's a lot of things, there's a lot of, I mean, there's a lot of finite games you can play that, that are really, really, really bad for you, uh, drinking. And, uh, um, uh, but it's amazing how often people play by games that, that actually don't level up to their own sort of moral, uh, uh, north star compasses. One thing I did is, uh, I, I, I mean, I, I really, really like, obviously, reading.

• 46:42Speaker 01

  I, I, I, um, I did read, uh, maybe not in super in-depth, but I, I, I tried to understand the stories of, um, the, uh, the rubber barons, the, the captains of industry, I think you're referencing.

• 46:55Speaker 02

  Yeah.

• 46:56Speaker 01

  Especially from previous times where the sort of the books open and close, at least, uh, in, in how people perceive them and, and thinking about them. I just kind of tried to figure out what, like, what were their motivations and why, like, what, what, what did they do? I find, like, I, I, I really, really doubt any of them, they're actually evil. I, I, I actually wonder if anyone, like, I, I, I mean, I'm sure it exists, but like, I think it's much rarer than people imagine that anyone says, okay, I'm, I'm going to exploit the system. Uh, I, I think everyone was sort of booking on, um, A infinite game that was actually important and got accomplished and therefore kind of faded into history and and and what people ended up spending a lot of time discussing ended up sort of the

• 47:40Speaker 01

  negative uncaptured and unacknowledged externalities of this success and progress of these periods, right? And so I so this is something I want to be really, really careful of this. I actually tried in my company to like, I tried to design a company that is aware of all the externalities that causes to to to the best degree that's possible, because sometimes you can only really figure this like, we did not know that putting carbon into the air is as bad as it was when we started figuring out the steam issues, right? Like, so at some point, we need to understand it and then we adjust. So that is there's some some of that that's going to be part of everyone's infinite journey.

• 48:21Speaker 01

  But just awareness of the externalities, like what actually happens? Like, is again, if if if if if a negative externality of of of of your work ends up being that, I don't know, like, attention is captured towards a a a means of finite sort of like pleasure of status games away from where it could be invested into internet games such as relationships of people around you. Then that's an externality that we have to talk about and kind of figure design around. I mean, I like the chief externality that I'm the Shopify is that there's more entrepreneurship,

• 49:05Speaker 01

  which is really, really good. So because there are positive externalities to success as well. And so I think at least the awareness of this, and these are things that we discuss in our company a lot. And I think that helps.

• 49:18Ryan Holiday?

  No, that's a that's a great it's sort of a corollary to the golden rule, which is like, what are the negative externalities of the things that I'm doing? How are although this is good for me, and I think the pandemic has really forced people to struggle with that and made us realize how bad we are at it. You know, even it's like, okay, I don't I'm not going to go to the grocery store because I'm going to socially distance, but somebody still has to bring me my groceries, right? And so really thinking about how your actions affect other people, to me, connects to another under discussed virtue in Stoicism, which is the virtue of justice. How do your actions affect other people? Although the Romans certainly weren't perfect at this, at least they were putting down

• 50:02Ryan Holiday?

  an operating system that we're continuing to tweak and refine that's reminding us of what those obligations to other people are.

• 50:10Speaker 01

  That's right. Again, I think the important thing is to be engaged in the infinite game. I mean, progress is never going to be as fast as everyone wants it to be, although we all agree that it should be instant. The important thing is the slow. And not just the first order effects matter. Again, it's really, really... The world has gotten... I mean, the world is really in a time where the primacy of all of our language is the finite games. And I personally think this is just reductionist.

• 50:51Speaker 01

  And because, I mean, it makes sense how we get there. Obviously, we explain the infinite game of gaining knowledge and education to our children by sending them to the finite game of succeeding in grade one, right? We're really, really good at puzzling out finite games underneath infinite games, and we forget to actually explain the infinite game. So I mean, this happens at companies all the time. They're like extremely successful people who come right off university, and the first day is, okay, well, what's the rules and how do I succeed? I write down this letter. And of course, we explain the

• 51:32Speaker 01

  entire life to you this way. But there's something much more important. Like, you played all these games and succeeded in them, not for the benefit of succeeding and being good in these games, but rather to get to the permanent benefits in your quest of to be of value to communities like the company you might want to join.

• 51:50Ryan Holiday?

  I had Steven Pressfield on not that long ago. I love Steven Pressfield. He's one of my favorite writers of all time. His sort of definition is that in the sort of archetypes of stories, heroes are villains are zero sum and heroes are non villain, are non zero sum. And I think that's a good sort of asking yourself like, is your company, is your business? Is your occupation, are you being zero sum about this? Or are you being non zero sum? And that to be zero sum means that other, somebody else has to lose for you to win. And not only is that like not correct, but it's just a crappy way to go through life also.

• 52:29Speaker 02

  Yeah, no, but the belief there is everywhere, right? Like, and it's, again, I find that really, really sad that this is one of our stories which gets airtime. Again, I understand it because it's simple. And again, because we spend so much time formulating everything valuable to do as finite games. It seems like it ought to be true because again, finite against R C or some, but like, obviously when someone's like, when, when, when, when a musician spends the evening like writing a hit song.

• 53:01Ryan Holiday?

  Yeah.

• 53:02Speaker 02

  Instead of doing something else, like they're not taking anything away from Planet Earth. Like it's purely additive. They will make a lot of money because not because they're capturing it from anywhere else. They actually created the entirety of the value of this song, the benefit that like, and they capture a tiny amount of the value they created. Like tiny, tiny compared to all the, the, the, the pleasure they caused and entertainment that was had. And I think this, this, this just seems like such a very basic story, but again, is, again, is actually one of the best stories in the world and is.

• 53:44Speaker 02

  Like not told enough, I find. Again, I keep coming back. This is why I'm so in love with entrepreneurship. My infinite games are about just making sure that entrepreneurship stays participatory and stays available as a thing to as many people as possible, because I think it's actually a fairly fragile institution and can go away for very, like as an externality to other things that are succeeding. And so this comes up as a concept for me a lot as you here and talk about building. I want to preserve this. Everyone who's entrepreneur gets this. It's not about taking something away. Like you sometimes hear about market share,

• 54:29Speaker 02

  but it's usually the capital side talking about market share. Sometimes entrepreneurs translate their infinite pursuits into finite language just to make it like easier to appreciate to the people who need to very much quantify everything. But I don't know a lot of entrepreneurs who actually think about things like this.

• 54:47Ryan Holiday?

  Well, that was something I was going to talk to you about because in a way that's where our two worlds intersect a little bit. What I love about Shopify is that it does. It empowers people to do things, to take ideas and get them to people who want to buy them, whether they're digital or physical. It's been interesting as my books have succeeded and then we built this thing, Daily Stoic, this platform. Sort of one option is you monetize with advertising and people seem to accept that this is a reasonable way to monetize intellectual property. And I do some advertising on the podcast and stuff, but then at some point I said, well, why, if advertising is effective, right, you're taking this spot

• 55:28Ryan Holiday?

  and you're selling it to someone who is only buying it because the revenue it generates for them is greater than the expense. I was like, well, why don't I just make my own stuff, right? So I started making these sort of philosophically inspired products. We make this Memento Mori coin. I commissioned this great artist to do this statue of Seneca.

• 55:49Speaker 02

  No, I know. You're just not shipping to Canada.

• 55:52Ryan Holiday?

  We are shipping to Canada.

• 55:54Speaker 02

  When you started recently, because when I tried, I couldn't get it.

• 55:58Ryan Holiday?

  Okay, well, let's talk about that in a second. But I started making this stuff and it's been funny. People, so the vast majority of people either don't care or if they're interested in it, they buy it, right? And then so doing support the stuff for everyone else. But there's also a percentage of people who get really upset and they go, oh, you're you're monetizing philosophy or you're commercializing it. And I've always had an interesting relationship this with because on the one hand, they'll go like, what would Seneca think? And I go, well, Seneca lived on an estate tended by slaves. So let's let's put his thoughts about commerce out of the question. But the other part of it is like, to me, I think an honest dollar is an honest dollar.

• 56:42Ryan Holiday?

  But but there are lots of ways to monetize philosophy. A college professor is monetizing philosophy, but actually in a in a much more zero sum way, because there's only one, you know, chair of ancient Greek philosophy at this university. It comes at the expense of other people. I actually like, and I think the Stoics, I don't think it's a coincidence that the Stoic was in the Agora. I think the the exchange of ideas and the the exchange of the marketplace is the most honest way to for for things to battle each other out. And if people want it, they buy it. And if they don't, they don't buy it.

• 57:19Speaker 02

  Exactly. And and here's a here's a wonderful thing is, I mean, obviously, this is not going to be a surprise. I'm extremely poor transactions as a form of relationship because it's pure, right?

• 57:33Ryan Holiday?

  Yeah.

• 57:33Speaker 02

  It's advertising is, again, it's a good business model. It's brought us a lot of great things. However, it is you interrupting someone, you you then direct them at something that might not be worth their time. And there's a lot of assumptions in it and it it's it's a different relationship. The wonderful thing, so the big success stories on Shopify are always like, like stories very similar to yours. The wonderful thing is, I mean, I mean, like, think of back, back, I think we are roughly similar age, like, like in the

• 58:12Speaker 02

  Early nineties anyways, when I went to school, uh, I, uh, late eighties. Sorry, I'm not making an assumption on your age. Yeah. But like, I, I was, I was in school at the end of eighties. Okay, um, so then, um, uh, although there was lots of staying power to what I'm invoking, like, everyone needed Air Jordans. Right? And, and partly because, like, Michael MJ was just, he was such a role model. He, he was like, like, you just appreciated what he was doing. He was driving to, like, to a standard that no one really had to drive him to. And, and now, we know for, for wonderful documentaries, that he actually, like, he, he, he needed, he, he actually had to manufacture motivation for himself, like, he created myths. Yeah.

• 58:57Speaker 02

  That, that, that he probably, um, like, used just to tap into deeper, because he was not interested in, um, uh, like, I think, winning basketball. He wa, he, he wanted, like, I mean, obviously, he wanted to do that, but like, he wanted to, he, he was on a journey figuring out how good people can become at basketball. Sure. And he, him specifically, and, um, but I think the, and the titles were, the externalities, obviously, we wouldn't understand all this as children. We know this now, um, but, uh, um, we knew that something was going on that was meaningful and different. And, and I think, um, like, I think getting the Air Jordan sneakers just got you closer to Michael. Like, there was, there was something of him in this.

• 59:40Speaker 02

  This is a pure relationship than if Michael, like, I mean, on the other side, I also grew up again in Germany during this time, was Michael Schumacher, um, uh, on, um, uh, in Formula One, um, like, also extremely dominate, dominating. Funny thing, I, I'm actually a big Formula One fan, but Formula One's a literally, uh, um, billboards going around the track at 300 kilometers an hour. Yeah. So, um, if you think about what the actual business model behind Formula One is, so, um, uh, but Michael, uh, like, Schumacher ended up on television all the time in advertising, selling toothpaste. Right. Um, and then selling. Like ridiculous cars by manufacturers, but you just know Michael is not going to drive this car.

• 1:00:22Speaker 02

  So you actually ended up, like, if you have a choice where you say, hey, um, this relationship I have has an audience for which I create value. Um, I could, I could now get, tell them about toothpaste or, or things like toothpaste, or I could create a product that is in keeping with the thing that people appreciate about what I'm doing, my work, and, and, and, and, and putting this ends up being a, um, it ends up deepening of a relationship. Like, you're not actually exchanging a little, like, a little bit of, uh, people's appreciation for, for, for your work, for the benefits of toothpaste, and then are compensated for it. You're actually deepening a relationship. And I think, um, the

• 1:01:04Speaker 02

  Western internet has not built enough of its foundation on top of transactions, because they're just, they're just a more pure relationship than advertising is. And it's interesting, Eastern internet, like specifically China, has actually not done this. Like, uh, like Eastern internet is a lot more transaction and a lot more e-commerce based. So there's an interesting, uh, like, um, sort of, like, path versions.

• 1:01:27Ryan Holiday?

  Yeah, it's like, I think people don't quite understand. So it's like, if you, like, if, if I sell my book, no one's like, oh, you can't sell a book, right? We understand books are transactions. But it's like, I sold that book to a multi-billion dollar corporation, who sold that book to another multi-billion dollar corporation, who may either be distributing it to, uh, independent bookstores, or, uh, you know, or it's going directly on Amazon. So millions and millions of dollars are being created, but the actual creator is getting a fraction of a fraction of a fraction of that. And, and then when you make something and you sell it directly, you, you not only, uh, are the margins better, but you don't have to reach nearly as many people. You can have a much, it goes to

• 1:02:08Ryan Holiday?

  that sort of idea of the thousand true fans, which I think is a, is a much purer relationship with the, the consumer or the customer. And, and it, it cuts, it cuts out all these, these middlemen that are, that, that sort of pretend like they're these noble figures, but are really, you know, uh, they're really just doing what all corporations have done for all time.

• 1:02:31Speaker 02

  That's right. And I think not only is this meaningful if what you want to do is increase the likelihood of makers and builders and people creating notable things, having, being able to do more of that, because every time we consume something, we are voting, not just for the thing that got created by an inventor, but actually for the entire supply chain that brought it to you. So like, if you have a dollar to spend and you spend it with, you know, like, to a random example, like a local cobbler making like boots, if

• 1:03:11Speaker 02

  you're too lucky to have something like this, you probably do in Austin. But then, or you buy a potentially like equivalent or worse or better boot through something like Walmart. I have nothing against Walmart, it's just that from your perspective, you've got a boot on either side. From the perspective of everything else that happens in the world, the entire world actually rearranged itself, like one dollar in the direction of whatever you voted for here. And so that, like, again, if you do the local person, they might end

• 1:03:51Speaker 02

  up, you know, making more, they might end up employing staff, they might end up, again, potentially getting themselves integrated in the global world of commerce. And there will be more of that, like your voting, actually. It's, we shape our world we live in significantly more by the dollar voting than actually the political voting, at least in the medium term.

• 1:04:18Ryan Holiday?

  Got a quick message from one of our sponsors, and then we'll get right back to the show. Stay tuned.

• 1:04:25Ryan Holiday?

  That's actually been my favorite part. You know, so put aside like, hey, is it better for me financially or not? Not as good for me financially. It's okay. So now I'm a manufacturer of stuff. And so I, as the creator, like, I don't decide where Penguin Random House prints my books. I don't decide what trucking company they use to deliver it from here to here. I don't even get to decide the price. But when I decide to make the Memento Mori coin, I got to choose to use like the oldest mint in the United States. And, and then when they're, when, when they got shut down from the pandemic, I got to decide like, hey, I'm going to preorder a large amount of coins from these people to, you know, to maybe help keep them in business.

• 1:05:09Ryan Holiday?

  I even, I like, there was a decision we made at one point, you know, like, so you do it and then they would ship it to the warehouse, you know, again, deciding to use a warehouse in the US. But, but, and if you're a Canadian, if I was Canadian, I'd be using Canadian. But, you know, it was like they were coming in these little plastic bags. They would, they would shrink wrap the coins in these plastic bags. And, and I remember I called the, the, the mint and I said, you know, do they have to be in these plastic bags? Like, is the plastic bag like protecting the product in any way? And they were like, no, just people tend to like them in the, you know, our, our customers tend to like them in the plastic bag. Well, I was like, don't, don't put them in plastic bags anymore. And, you know, tens of that, my choice as the individual creating the thing on my own

• 1:05:53Ryan Holiday?

  small scale gets to eliminate tens of thousands of little plastic bags from the supply chain in the way that you would never, you'd never have the power to do. And to me, that's a very stoic idea, which is, although sure, collectively, we can come together to change the world. Also, we need to do a really good job at just having as much control over our own stuff as possible and trying to do that according to our own standards.

• 1:06:18Speaker 02

  I love this. Thank you so much for like digging this deep into like the making of something like this because I think both unfortunately, we are not good at telling the stories, right? Like it's, it's, it's very, very few businesses actually take anyone on the journey of decisions like this. But it's, it matters because again, if, if, if that particular copilot I talked about ends up closing doors. All like no like you it's it impoverishes the community because it no longer can vote. It's like as if as if elections are canceled to a meaningful degree like I want to support all the what you just talked about because that is the degree by which I

• 1:07:01Speaker 02

  I I I mean I love the topic I love like I love the concept of taking something that has some heritage like a mint and and and and helping them create products that are of relevancy to in in in their digital times because I mean let's be honest like mints don't have that much to do anymore. Right. And but they are incredible and there's a history to them and they need to be preserved and so again people can now vote for in the particular case that they would like to acquire this to for for an entire system that that that made it I think that's important. I think this is the thing that people miss especially when

• 1:07:40Speaker 02

  they come in for zero sum mindset where like how good and how important commerce and actually is I think there's like this is unfortunately the bad stories end up just getting more airtime than the good ones which is also generally true. People talk about consumerism. Consumerism is such a misdirection like consumerism doesn't exist because people love the products love product. People consumerism exists because people hate the products they end up getting like it's the solution to this is connect them directly to people who actually care about the products all the way instead like getting rid of like the five procurement manager middlemen who are

• 1:08:25Speaker 02

  really their job is to put something into eye height and they need a very specific product based on the orthodoxy of thinking for the last 50 years about what should be at eye height in the shelves and therefore your product was would potentially never have made it or would have had to be significantly altered to adhere to some price points that other people thought and again yes for 1000 true fans but often it's not 1000 like it's actually this this compression of the process of what can be created is actually the thing that I think caused consumerism to to to to to even appear to the degree it did like if you look at like we have millions of businesses on Shopify now which are incredible but like this business like Albert's like Albert's is such a good

• 1:09:10Speaker 02

  company like on like. It's again so much philosophy behind it. And yes, it's a sneaker. It's an amazing sneaker. It's honestly kind of the best, like for, depending on what that means to you. It might not be true, but like to a lot of use cases, they are just incredible. But they also have like, they are designed with all the externalities in mind. They are incredibly sustainable to a degree that probably no one else has reached outside of them. If they would have had to sell for Foot Locker or any of the channels, they would just wouldn't have been, they would say, let's make, the bill of materials can be $10 lower by not doing all this. So let's do that because we want to hit a price point. And this product would have never existed so that people could vote for it.

• 1:09:54Ryan Holiday?

  Yes.

• 1:09:55Speaker 02

  And now that people can vote for it, they vote a lot for all those. And they have like places all over the cities and it's a thriving business that now is available to everyone to say, hey, actually, we would like our sneakers to conform to ideals that we hold ourselves. And therefore, you know what has to happen? The rest of the industry has to kind of say, you know what, we probably have to look for supply chains to get to some kind of redundancy and think about just how powerful this all is. And without the ability for the makers to go direct, this just doesn't, this goes away.

• 1:10:31Ryan Holiday?

  Well, that was something I learned at American Apparel, which was a flawed company in a lot of ways. And I would never pretend Dove was a philosopher, but I remember him breaking it down for me. He was like, okay, Gap or one of these main chains, H and M, he's like, they pay a sweatshop wage at some factory in Bangladesh or Taiwan or Guatemala. And he's like, they can make this T-shirt for 42 cents. And he's like, I can make it here in the U.S. for $2. So he's like, on the one hand, it's like eight or nine times more expensive for me to make it at the level that they're making it.

• 1:11:12Ryan Holiday?

  If I'm selling the T-shirt directly to my customer for $25, trying to get the marginal cost of the goods from $2 to 40 cents is not even remotely the most efficient place for me to focus my energies. Like, I'd rather just try to make a cool story and to have a cool product that people actually want and be able to sell it for $27 instead of $25. And I think that's been interesting for me, too. Like, we're doing this self-published book, which I'll tell you about offline. Actually, you know what? No, this episode will run. I don't know. But I decided to do a self-published book. I'm doing a kid's book.

• 1:11:55Ryan Holiday?

  And the decision, you know, it was, you know, let's say, a dollar a copy to print it in China, and then you have to ship it over on boat. So there's a whole environmental part to it. And then there are a long delay. So I could do it in China for a dollar, or I could do it in America for $3. So again, it's 300% more expensive to do it in the US. But my royalty selling it through a publisher would be like $3 total. If I'm self-publishing it, my royalty is so much greater that I can be generous and say, "I'm not going to try to squeeze some US factory worker out of the opportunity to print something."

• 1:12:37Ryan Holiday?

  So I think the real good that Shopify creates and going direct is that it creates room for people to be less ruthless with each other. And then it gives the individual... Look, are there plenty of people who are using the efficiencies of Shopify to just be ruthless on their own individual scale, of course? But I think it also gives the individual the chance to be as good as they are willing to be.

• 1:13:05Speaker 02

  Yeah, you're 100% right. You know, it's a big platform. Everything goes on. And the good thing as well about...

• 1:13:17Speaker 02

  You know, it creates, it makes it so that there's a kind of an equality of opportunity. And I think this is like, this is the one thing I, whenever I end up talking to politicians, we spend a lot of time talking about entrepreneurship, but really largely create policies against them, sadly, usually not for their own, not directly, but indirectly against, or to their effects.

• 1:13:45Speaker 02

  Which is so important, like, like the, the, the minimum thing we have to do is a preservation of equality of opportunities, so, and which is, by the way, is even that is an infinite journey and it's nowhere near there, right? Like, there's a lot, like, a lot of things have to happen before people even are aware of opportunities in front of them. Like, I, my, my grandmother had a print shop, a wonderful letter presses and like big noisy machines growing up, which she loved spending time in, and she, she, she wasn't an entrepreneur. So just, I feel like through, like an accident, like entrepreneurship, I think was something that was in my toolbox, which I could bring out when I had an entrepreneurship sized problem in my life.

• 1:14:29Speaker 02

  But there's, like, many, many people just don't have role models there. And, and I think this is sort of, I mean, we, we came at the same point when we talked about stoicism or life philosophies as well. I think it's a noisy world and, and, and we have, we have, the stories that move are the stories that have virality in them, and they really are those the most valuable stories to write about. And so, I mean, it's funny because I was actually thinking before our call is like, I, I was gonna quiz you if you were thinking about doing a children's book on, on, on philosophy and stories. And I love that you already, I mean, they don't know what it's about, but the fact

• 1:15:11Speaker 02

  that you mentioned and invoking that is music to my ears because again, it's, it's a wonderful concept to get, gets to, to introduce early. It happened to me again, by completely freak accident with quotes in the end of my Latin textbook, right? Right.

• 1:15:25Speaker 02

  If I go back and connect the dots of things that are really meaningful to me

• 1:15:30Speaker 02

  in my life, it's extremely fragile, the kind of on-ramps that I've found. And any like, any different decisions on a particular day thirty-five years ago might have sent me in a completely different direction. And I think I would be upset by that.

• 1:15:51Ryan Holiday?

  No, I think about it the same way. I was at a conference and I asked someone for a book recommendation and they recommended the Stoics. And it's only because Amazon sent me that translation of Marcus Aurelius that, you know, they could have sent me another one or I could have read the Project Gutenberg version and it would have turned me off. And I think even, you know, to go way back, Marcus Aurelius is given a copy of Epictetus by Rusticus. And imagine if, I don't know if he'd spilled water on it or something or if he'd gotten distracted and he lost it. Like, all of history might have turned out differently. Like, it really can pivot about your access to something.

• 1:16:30Speaker 02

  I'm curious about, like, so like, let's play this counterfactual. Because I agree, just like from his writing, it just really seems like, I mean, we don't know exactly what book he got there, but Epictetus, I don't think they met and it seems like it had a very significant influence.

• 1:16:47Ryan Holiday?

  Yeah.

• 1:16:48Speaker 02

  Like Aurelius is very sort of Epictetus flavored.

• 1:16:52Ryan Holiday?

  Yes.

• 1:16:52Speaker 02

  And so in a counterfactual case, do you think it like could have turned out Nero?

• 1:17:01Ryan Holiday?

  Well, I think we all have that. I think we all have a dark side that could get, you know, could become unlocked by, you know, sequences of events. I guess the Stoics would sort of say it's all faded. So maybe they didn't believe in it. But to me, if it couldn't have turned out differently, it's not very impressive.

• 1:17:22Ryan Holiday?

  You know, like, it's only that it was a conscious choice. Like, are you familiar with the choice of Hercules? Do you know this myth?

• 1:17:30Speaker 02

  Uh, no.

• 1:17:31Ryan Holiday?

  So Hercules, as a young man, is a myth, but he comes to a crossroads. And this is the famous temptation of Hercules, where on the one hand, there's the goddess of vice and the other, the goddess of virtue. And the goddess of vice makes all these, you know, tempting offers and, you know, promises in the world and virtue promises him nothing and says that it's going to be hard work. And so without that choice, if it's faded, you know, is it, is it, is the, is the outcome impressive? Like, if Shopify couldn't have failed, is the, is the success of it as much of a credit to you? Probably not.

• 1:18:08Speaker 02

  Right, exactly. Now, that, that particular subplot would have been okay. It doesn't need to be credit to me, but like, I don't, I don't think that, um, um, yeah, I, I mean, I certainly believe in path dependence. I, that's where the stoics tend to lose me around lagos and fate. But, um, I don't know, it's also like a, it's, it's, it's a construct of the times. I'm just trying to figure out, like, again, you're, like, you're right, I didn't know it's called the temptation of Hercules. But like, having such a story, I imagine during certain times, this was a story, like, just the fact that it survived means that it was sort of a superbowl of its time.

• 1:18:48Speaker 02

  And, um, uh, what does society would look like when that is part of a origin story, right? Like, that is something that everyone can be assumed to have an understanding. And I mean, how often the Greek, let's get back to this, like, it's the sirens and everything. It's, um, the temptation of the easy path, the thankless road to virtue.

• 1:19:14Speaker 01

  I mean, it's just demonstrably true, right? And so, but like, it doesn't play a contemporary role that much outside, like, that I can observe.

• 1:19:25Ryan Holiday?

  A really funny sort of historical what if is that John Adams proposed that the choice of Hercules be what's on the seal of the newly founded United States. Instead, we went to an eagle, which is cool for different, but he wanted the choice of Hercules to be the sort of the story of the United States, which I think would have been much, much better.

• 1:19:49Speaker 01

  I think that would have been a good idea.

• 1:19:51Ryan Holiday?

  I had one last question for you, and I'll let you go. But I feel like being, having you on is an opportunity to ask a philosophical question that the Stoics talk about. I think readers think about it in theory, but maybe, you know, or few of us would ever really experience. You know, Seneca has this strange relationship with money, right? He's the austere Stoic, but he's also one of the richest men in Rome. Marcus really is obviously quite wealthy. A lot of the Stoics were, how, I'm just fascinated, like, what is it like to suddenly have more money than a human being could ever possibly need? Or, or not, maybe not cash, but have access to, you know, more than a person could ever need?

• 1:20:33Ryan Holiday?

  How have you wrestled with that or thought about that philosophically?

• 1:20:38Speaker 01

  Yeah, it's, again, I think I'm pretty, I hope I'm reasonably early in my book, and I don't think I've written the chapters on this yet. It's, it all happened very suddenly. And I'm like, actually, like, I have pretty, like, all my hobbies are fairly cheap, you know, so honestly, I, I, the moment I can have a reasonably recent Apple laptop, I'm rather happy. So it's, maybe I haven't adjusted to this. It just, you know what, I just never cared about money. It's really, it's been, I just never spend a lot of time thinking about it. Now, I did grow up, again, with significant technical skills in the probably most valuable time to build them.

• 1:21:22Speaker 01

  And so, I probably, it's probably a privilege that I never had to think a lot about money because I just had such an enormous, like, I just had a set confidence that I can make as much money as I needed through my technical skills. So I think it faded fairly early. And then, you know, now it's like, but...

• 1:21:43Speaker 01

  I think more about energy. I think it's actually energy is a better proxy. So like I think money is a form of energy that can be directed into causes and creating things that you really want to exist. I actually, I think my company itself, for the things that I would like to put energy into is a significantly larger input than all my money could be. Like again, in the sort of porting and preservation of entrepreneurship to the internet, to the digital times, and creating some equality for charity there is what I spent a lot of time thinking about. And not even having an entire company like this is not even remotely equivalent to like attention.

• 1:22:24Speaker 01

  I think attention is the hundred or thousand X version of energy. So whatever you end up spending your attention on is the things that are moving forward the most. And when money, money as a strong discount can be used now at the degree that like I now have been insanely lucky, I see it a lot as an obligation. Like I want to learn how to give it like, how to use it well for the benefits to, to, to level up into, I think what both of us would agree to be virtue. I, I don't, one takeaway from the studying of the early success story with Rockefeller's and Carnegie's and so on, is I think it shouldn't happen like, like I, I think it's a bad idea

• 1:23:09Speaker 01

  to run like some operating system of pure capitalism, acquire as much and then try to make amends afterwards for library building. But like, we should also acknowledge the incredible benefit that had, that had had.

• 1:23:26Speaker 01

  I try to like just keep everything in harmony as much as I can. So this is how I'm thinking about it, but it's, it's, it's interesting. It's, it's. I don't end up spending too much time on it yet, partly because I also fire almost unshared attention, but it's certainly not something I was looking to get into or in need for any particular reason.

• 1:23:49Ryan Holiday?

  Yeah, the Stoics talk about money and fame and things as a preferred indifferent, like nice to have but not necessary, and that sort of sounds like what you're saying.

• 1:23:58Speaker 01

  Yeah, I think so. I mean, I'm not surprised by Stoics, but I have a very good relationship to this. Again, it's totally okay to enjoy things that sort of nature or just sort of happened to you, I think. So you don't wanna like, because people have weird conceptions about what Stoicism means. But yeah, I think it's, yeah, it's a complex topic. It's, you know, the reason why it's complex is also, again, because of culture, right? Like, again, we're running some like firmware that's fairly significantly related

• 1:24:36Speaker 01

  to Christianity over here. And so, you know, there's, there's a lot of language around money in there that sort of codes us into the zero-sum belief of money and the fact that money is gained from conflict. I mean, it can, it can be gained in a lot of different ways, but I think money is also extremely path-dependent itself. Like, how did money, how was money created matters, right? Like, if the money was created by, like, creating some, like, high-frequency trading algorithm that was a millisecond faster than everyone else, then, you know, like, I mean, even that is probably a value for some weird sense of liquidity in a market, maybe, but like, it should be held as a discount to the enablement

• 1:25:20Speaker 01

  of significantly, like, capturing a tiny percentage of creating significantly more actual value in the world. And I think that's, so I think as long as it's tech money that comes for process building, I think it's also, there's some, somewhere at least, I think it's better this way.

• 1:25:40Ryan Holiday?

  You know, it goes to your point about negative externalities, and Seneca says, you know, "A philosopher can be rich, but a philosopher's money should not be stained with blood." Ironically, in Seneca's case, it certainly was, but I would say, I would say generally, the Stoic view should be, money is great, provided it's not dirty money.

• 1:26:01Speaker 01

  Yeah, I agree. I think that's a good way for it. That's a good, that's a significant simplification of a monologue I went on, but like, as we say, like, people had all the good thoughts 2,000 years ago.

• 1:26:11Ryan Holiday?

  Yes, they certainly did. No, this was so great. I'm so glad we connected. And seriously, thank you for everything you've done with Shopify, because I don't know if we'd be doing this show if it didn't exist. It's helped my life immensely. Not only not a negative externality, you have created more value from me than the tiny little Shopify fees have captured back. So I appreciate.

• 1:26:35Speaker 01

  Awesome. This is great fun. Thank you so much for having me on.

• 1:26:38Ryan Holiday?

  No, thank you.

• 1:26:41Ryan Holiday?

  Thanks for listening to another episode of The Daily Stoic. It's mind blowing to me now that we are well over 30 million downloads of this show. It means so much to me to have all of you listen. If you want to help spread the word about the show, please leave a review on iTunes or whatever your favorite podcasting platform is. It helps a lot. And then, of course, click subscribe. That's how we know how many people are listening and that makes sure you get the episodes as they come in. So thanks again for listening to the Daily Stoic Podcast.