Empathy Is Not Weakness | Will Guidara

Empathy is not the opposite of Stoic strength. It’s part of what keeps that strength from becoming coldness. In today’s episode, Ryan talks with Will Guidara, author of Unreasonable Hospitality, about why empathy is one of the most powerful skills a leader can build. They discuss why hospitality is really about making people feel seen, the Stoic idea of slowing down to speed up, the importance of not wasting adversity, and why we should never let someone else’s bad behavior pull us away from the person we want to be. Will Guidara is a restaurateur, speaker, and the author of Unreasonable Hospitality: The Remarkable Power of Giving People More Than They Expect and the new Unreasonable Hospitality: The Field Guide. He is the former co-owner of Eleven Madison Park, which earned three Michelin stars and was named the number one restaurant in the world. Will’s work on hospitality has been featured in his TED Talk, The Secret Ingredients of Great Hospitality, and his book Unreasonable Hospitality was featured in the hit series The Bear.📚 Pick up signed copies of Unreasonable Hospitality and the new Unreasonable Hospitality: The Field Guide at The Painted Porch! 👉 You can follow Will on Instagram @wguidara Ryan Holiday is coming to a city near you! Grab tickets here | https://www.dailystoiclive.com/🇺🇸 USA dates:Portland, Oregon - June 8 San Francisco, California - June 11Minneapolis, Minnesota - August 18 Chicago, Illinois - August 19 Detroit, Michigan - August 20 🎥 VIDEO EPISODES| Watch the video episodes on The Daily Stoic YouTube channel: https://www.youtube.com/@DailyStoic/videos✉️ FREE STOIC WISDOM | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail

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

• 0:00Ryan Holiday?

  Welcome to the Daily Stoic Podcast, designed to help bring those four key Stoic virtues: courage, discipline, justice, and wisdom into the real world.

• 0:15Ryan Holiday?

  Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. It's funny, like, just a couple of years ago, there was this whole sort of resurgence and discussion about empathy, the power of empathy and vulnerability and connection. I think Brene Brown is obviously a big proponent of this, popularized it. And then naturally, there's going to be a backlash. There's always, always the swinging of the pendulum. But I think we're definitely going too far in the other direction these days, this backlash. Actually, when I was on The Daily Show, I was asked about this very idea. This is what I said.

• 0:47Speaker 01

  I think so many men in particular are drawn to daily Stoic. As a man myself, who really enjoys your books and your YouTube and your Instagram, I see men in leadership positions now, and I don't connect. I see our current administration. I see a lot of the podcasters. And I think it's hard for me to connect with them. I don't feel like those are the men I want to be. It doesn't seem like a healthy balance. Elon Musk, this brilliant, brilliant man, and now it seems like he's a cautionary tale to men. How do you feel that so many men are, you know, you are their Stoic? Or how would the Stoics advise you to be in this position?

• 1:26Ryan Holiday?

  Yeah, I feel like I'm one of the few male influencer types that did not become radicalized or red-pilled. So, like, Stoicism is not supposed to make you a better sociopath or a bigger asshole. That's not what this is.

• 1:47Ryan Holiday?

  That's, that's the ethical component, right? I think Elon Musk was on Joe Rogan, and he said, you know, empathy is going to cause the destruction of Western civilization. That is a profoundly stupid thing to say and think.

• 2:05Speaker 01

  Well, you talk about him a lot. You talk about him a lot in the book, and it seems like part of the point you're making is maybe here's a brilliant man who's done a lot of amazing things, but wasn't on this path to wisdom.

• 2:17Ryan Holiday?

  I mean, to say that Elon Musk is not smart is like saying he's not rich. He's clearly very smart. But that is what is so scary about it, that you could be so brilliant, so gifted, so informed, you could have been so successful, and then social media can still break your brain.

• 2:33Speaker 01

  Right.

• 2:34Ryan Holiday?

  And it did. It did. This is a guy who went from reading Soviet rocket manuals to figure out the aeronautics business, to following like Cat Turd 7 on Twitter. And Russian bots from whom he now gets his information and his worldview. And that is, I think, a tale as old as time. You become successful, you think that you're smart, and that is when you start to get real dumb. Because, as the Stoics say, it's impossible to learn that which you think you already know. I think you can make a very clear case for empathy in the sense that if you are making things for other people, which we all are, whether that thing is customer service,

• 3:15Ryan Holiday?

  or that thing is a book, or that thing is music, or that thing is food that people want to eat, we're doing a thing for other people, which means we have to understand other people. We have to understand those people's perspective. We have to be able to communicate and connect with those other people. And that's what we're going to talk about in today's episode. Will Guidara is a friend of mine. We had a lovely talk at Barnes & Noble when the last book came out. That was fun. And his book, Unreasonable Hospitality, has been a monster hit in the years since. He was the co-owner of Eleven Madison Park, which earned three Michelin stars and regularly rated the number one restaurant in the world.

• 3:58Ryan Holiday?

  He's a very successful business person and entrepreneur and thinker. He was on The Bear, maybe you saw that. And he has a new book called Unreasonable Hospitality: The Field Guide, which is really cool. He spent his whole career thinking about service not as something transactional, but as something noble, something even moral. And so I wanted to talk to him about that in today's episode, how empathy informs that. I'll talk about a bunch of things in this episode, honestly. The standards we hold ourselves, the things we do for other people. I talked about adversity and generosity, the nobility of service. And then Will's idea of making a charitable assumption about other people. And look, whether you're running a restaurant, or leading a team, or building a business,

• 4:40Ryan Holiday?

  or just trying to be a decent person, hospitality is not like an afterthought. It is the main thing. I'll just get into it. I think this episode is great. And we ended up nerding out about some Stoic themes in here, too. So here's me talking to Will Guidara.

• 5:06Ryan Holiday?

  I wanted to start with this idea of empathy, because it seems like there's this kind of backlash against it. I don't know if you saw this interview where Elon Musk is saying that he thinks the downfall of Western civilization will be empathy. That's not something I had on my bingo card for where I thought things were going. I mean, it's certainly obvious with what's happening in the world that we're not being empathetic enough. But the sort of overt criticism of the idea of considering what other people think and caring what other people think is just not what I would have predicted.

• 5:37Speaker 02

  Yeah.

• 5:38Ryan Holiday?

  Particularly from a successful business person, because it's cool. Like, how can you sell things to people if you have no theory of mind of what's existing over there?

• 5:48Speaker 02

  It's interesting. I just saw a clip, it just came up on my feed, of you on The Daily Show.

• 5:54Ryan Holiday?

  Oh, yeah.

• 5:55Speaker 02

  And what you said, I 100% agree with. It is objectively true that he is smart.

• 6:00Ryan Holiday?

  Yeah.

• 6:01Speaker 02

  And yet.

• 6:03Ryan Holiday?

  It's a stupid thing to say.

• 6:04Speaker 02

  To hear someone say something that, it feels so beyond anything I can even conceive as being a smart thing to say.

• 6:11Ryan Holiday?

  On two levels, right? It's objectively stupid. And then even if it is your opinion.

• 6:16Speaker 02

  To say like, this is something I'm gonna say out loud.

• 6:18Ryan Holiday?

  Exactly. Like, that's kind of what, one of the things empathy prevents you from doing is voicing all your true thoughts.

• 6:25Speaker 02

  Yes.

• 6:26Ryan Holiday?

  Until you've either worked them out or like they're thinking about the context in which you're saying.

• 6:33Speaker 02

  Yeah. Although it's interesting to think of this idea that we probably need people who have no empathy in order to have some of the more remarkable innovations that happen in society, like those that care so little about others that they're focused entirely on the thing they're building. I mean, probably some of the greatest innovations have come from people who lack empathy entirely. That said,

• 6:57Ryan Holiday?

  Yes.

• 6:58Speaker 02

  As a culture.

• 6:59Ryan Holiday?

  Yeah.

• 7:00Speaker 02

  We need to celebrate the idea of empathy because absent it, I don't think we're ever going to be moving wholly in the right direction.

• 7:08Ryan Holiday?

  Yeah, although like.

• 7:10Speaker 02

  Do you know what I mean when I said that?

• 7:11Ryan Holiday?

  I mean, part of being a technologist, let's say, or an inventor is like, I'm fascinated with this. I'm going to make this. I'm not going to be thinking 15 steps ahead about what this means for three generations from now.

• 7:24Speaker 02

  Yes.

• 7:25Ryan Holiday?

  Or like, how can you invent, say, military technology if all you're thinking about is like the potential victims of said military? How can you send people into space?

• 7:33Speaker 02

  Yes.

• 7:34Ryan Holiday?

  If you're crippled by your sense of like, well, what about their families?

• 7:37Speaker 02

  Yeah, yeah.

• 7:38Ryan Holiday?

  Like, there are certain professions that require you turning off or turning down a little bit of your empathy. But I would argue, like, at a basic level, when you make things for other, like, sure, he is a technologist, but he also makes cars that people want.

• 7:54Speaker 02

  Yes.

• 7:55Ryan Holiday?

  And, and he has to sell them to them for like, it's one of the biggest purchases they'll make in their life. If you can't conceive of what people want, what people like, how they'll, they'll interpret certain things, you end up making massive strategic blunders, the Cybertruck being one.

• 8:10Speaker 02

  Yeah.

• 8:11Ryan Holiday?

  But you also, it's as if he didn't conceive of like politicizing himself, having a negative impact on the sort of like California liberals who buy his car.

• 8:24Speaker 02

  Yes.

• 8:24Ryan Holiday?

  Yes.

• 8:25Speaker 02

  No, no, no. Listen, my, everything I believe in is centered around the idea that empathy is the greatest superpower one can have.

• 8:31Ryan Holiday?

  Right.

• 8:32Speaker 02

  One of the things I think of, because hospitality is not just about how you serve, it's how you lead and. The idea of surrounding yourselves with people who are not all the same, but their respective superpowers complement one another's, right? And on my team, I always want to have someone who is a driver, who is so focused on excellence, they don't care about what they break along the way.

• 8:55Ryan Holiday?

  Right.

• 8:55Speaker 02

  I don't want that person to be in charge.

• 8:57Ryan Holiday?

  Yes.

• 8:57Speaker 02

  To be clear, but I want that person's influence in the room. And Elon's power is grown to the point where I actually would prefer he is empathetic. But my point is that it takes all types to move us in the right direction.

• 9:10Ryan Holiday?

  The idea of like, oh, to be great, you have to turn off empathy or you have to

• 9:15Speaker 02

  No.

• 9:16Ryan Holiday?

  Close down. And like, I mean, I think the restaurant industry is a fascinating example of like, some people who either make that bargain or buy into that assumption. But who's the chef that just?

• 9:26Speaker 02

  Rene Redzapi.

• 9:27Ryan Holiday?

  Yeah, at Noma, right? It's Noma?

• 9:30Speaker 02

  Yeah.

• 9:30Ryan Holiday?

  He probably thought that was necessary. And then you read about it and you're like, what are you talking about? This seems insane. What does this have to do with cooking food? Like taking someone out back and humiliating them. I think I was reading like physically abusing them on top of the humiliation. So what is that? Why do people think that that is part of succeeding in the industry? But it seems like food particularly.

• 9:52Speaker 02

  There's a chef named Sean Brock. Do you know that?

• 9:55Ryan Holiday?

  No.

• 9:55Speaker 02

  He is like the great, one of the great chefs of the South. So like really celebrating Appalachia and like the food and the ingredients and all this stuff. He had a restaurant in Charleston and now in Nashville. And he just opened a pizza place. He, that's not what he has been cooking for a long time. But during COVID, I think he started making pizza as a hobby and got obsessed with it and opened a pizza place in Nashville. And when he posted about it, the caption I loved, he says, obsession is a beautiful thing when you can grab it by the tail.

• 10:24Ryan Holiday?

  Like when you can control it?

• 10:25Speaker 02

  When you can like rein it in. And I think there are those that become so obsessed that they just lose control along the way. And I don't think it is. That they are bad people. I think that they just lost their way along the way.

• 10:45Ryan Holiday?

  Well, they stopped thinking of the people they're working with as people and they see them as tools or ingredients in the same way that they don't have a lot of thought about the knife they're using or the.

• 10:54Speaker 02

  Yeah, I think they just became so maniacally focused on achieving this goal that they stopped thinking about anything.

• 11:01Ryan Holiday?

  Yeah.

• 11:02Speaker 02

  Except for that, not realizing that if you don't genuinely care and invest.

• 11:09Ryan Holiday?

  Yeah.

• 11:10Speaker 02

  In the people that are helping you achieve it, you're never going to take it as far as you could.

• 11:13Ryan Holiday?

  And it seems like it's pretty hard to partially turn off your empathy. So you're like, hey, I exploit these people in the back of the house.

• 11:21Speaker 02

  Yeah.

• 11:22Ryan Holiday?

  But I actually genuinely deeply care about the people sitting in the front of house. Like, no, I think at some level, you start to see everyone as a tool, everyone as a means to an end, everyone as expendable, everyone as a commodity. And then ultimately it blows up.

• 11:38Speaker 02

  Well, that's why, I mean, and this is not just limited to restaurants. I think you see it in a lot of places, but the restaurant example is that this is kind of starting to go away a little bit. But there were restaurants where you'd go into and it was almost like you were there to like kneel down at the altar of the chef, right? Like there was a restaurant once I went to and on the menu it said, we don't change our dishes. If you have an allergy, don't bother telling us. Like it's one of the things like, I think there are restaurants that believe the customer is always right. I actually don't believe that to be true. And there are restaurants that would say the chef is always right. You are there to experience their genius. Each of those is a monologue.

• 12:20Speaker 02

  And I actually think hospitality, any meaningful relationship, it's a dialogue. It's somewhere in between those two.

• 12:26Ryan Holiday?

  Well, it's fundamentally not. Just about you, or you wouldn't have turned it into a restaurant. You see this with authors too, they're like, I'm making this just for me. I don't care what the audience thinks. It's like, so why'd you put it between two covers? You know, like, you did a lot of other stuff that had nothing to do with the project. That was hard and took longer and was a distraction. Like, if you really were the pure artist that you're saying, you'd put it in a drawer.

• 12:50Speaker 02

  Yeah.

• 12:50Ryan Holiday?

  Like, you do care.

• 12:51Speaker 02

  Just go to your living room and read it once in a while.

• 12:54Ryan Holiday?

  Or just think about it. Like, why even put it into, why even, why even write it? Just let it exist perfectly up here. So it's like, if you actually only cared about your, your, the genius of the food, like, you just cook for yourself or your family. Like, why, why did you put it in this high-traffic location in Manhattan?

• 13:10Speaker 02

  Yes.

• 13:11Ryan Holiday?

  Like, and why'd you open the doors and you let people in?

• 13:13Speaker 02

  Hire all the people and do all the stuff.

• 13:15Ryan Holiday?

  At some level, you do, you do understand. It's almost like this kind of like defense mechanism of like, but, but I'm not, I'm not gonna take you into account in any real way, because then there's like a vulnerability. And then you have some say over whether I did a good job or not.

• 13:29Speaker 02

  But I think that mounts over time. Like, you open whatever business, you write a book, you open a restaurant, you do it perhaps rooted in all of the right intentions, and then you start to succeed. And then people start telling you how amazing you are.

• 13:43Ryan Holiday?

  Yeah.

• 13:43Speaker 02

  And then one day, you start to believe them to the point that it actually changes the very foundation of, of what you're doing.

• 13:51Ryan Holiday?

  Well, you get away with it.

• 13:52Speaker 02

  Yeah.

• 13:52Ryan Holiday?

  That's the cra- the, the Noma thing was crazy, because he was obviously so famous and so well-liked. And then, like, lots of people experience, whatever that, like, sort of firing line scene that's in that New York Times piece, where he took the guy outside and then everyone took turns screaming at him or hitting him, I forget what it was exactly, but you're just like, first off, like, you thought this was okay. And then everyone else at some level thought it was okay, because it, it didn't, it's not like this New York Times piece is coming out the day after it happened. Like, there's a world in which everyone's like, I guess this is just how it is. And like, it's insane when you see it written down. And yet, all these different people at different levels were participating in a culture that said like, this is okay, this is normal.

• 14:35Speaker 02

  Which exists in so many places.

• 14:37Ryan Holiday?

  Of course.

• 14:37Speaker 02

  I mean, one of the things that I, I so firmly believe is that if you don't have at least one, hopefully many more people on your team who you have gotten to know so well, that they trust you enough to tell you. When you are losing yourself in pursuit of something.

• 14:55Ryan Holiday?

  Yeah.

• 14:55Speaker 02

  You will lose yourself.

• 14:56Ryan Holiday?

  Mm hmm.

• 14:57Speaker 02

  Like, you, you need the people on your team that are like, hey, bud, you're not, you're not being awesome right now.

• 15:03Ryan Holiday?

  Yeah.

• 15:03Speaker 02

  They need to trust you enough to say it, and you need to trust them enough to believe it when they say it.

• 15:07Ryan Holiday?

  Or at least to hear them. This sucks.

• 15:09Speaker 02

  Yeah.

• 15:10Ryan Holiday?

  Or this is a ripoff, or this is unethical.

• 15:12Speaker 02

  Yeah.

• 15:13Ryan Holiday?

  Or any, any number of the.

• 15:15Speaker 02

  And you can look across pretty much every part of our society right now. And the people that don't have anyone in their lives telling them that they are not being their best selves are the ones that are doing the most damage.

• 15:28Ryan Holiday?

  Yes. Yeah. You think you don't want, you don't want an adversarial, you know, investor, or you want your hand, you think you want your handpicked board of directors, or Secretary of Defense fires all the JAG officers and calls them JAG-offs. It's like, no, they're there so you don't fuck up. Like, they're annoying and obnoxious at some level, I'm sure, because you have a divergence of interests, just like, I mean, anyone that talks to a lawyer understands how frustrating, like, their job is not to tell you.

• 15:58Speaker 02

  Yes.

• 15:59Ryan Holiday?

  How to get away with what you want to get away with. Their job is to tell you what you might not get away with.

• 16:03Speaker 02

  Yes.

• 16:04Ryan Holiday?

  That check against check is a really important way that you don't spin off the planet.

• 16:09Speaker 02

  It's like a red team in the news, right? You need a red team on your team. So, and it was like, I just don't like this idea for this rea- and by the way, you may still decide you want to do it.

• 16:18Ryan Holiday?

  Yeah.

• 16:18Speaker 02

  But you need to at least be open to the conversation about why you could potentially be wrong.

• 16:23Ryan Holiday?

  So I think the problem with empathy is we think it's like, you have it or you don't, it's necessary, it's not. I don't think we think about it as a skill. Talk to me about empathy as like, a skill that you cultivate.

• 16:35Speaker 02

  I mean, empathy is in many ways synonymous with hospitality, right? Not entirely, but in, in many ways. And it's one of the things that I'm kind of screaming from the mountaintops right now is that hospitality empathy is a craft.

• 16:49Ryan Holiday?

  Yeah.

• 16:49Speaker 02

  It is a muscle you can strengthen, a practice you can pursue in the same way that writing, or a sport, or cooking is a craft. And it's one thing I think we have not understood for a long time. Even when I was coming up, some of the people that I respected the most would say, hire for hospitality, train for excellence. As I have to say, there are those that are hospitable.

• 17:07Ryan Holiday?

  Yeah.

• 17:08Speaker 02

  And there are those that aren't. Hire the ones that are and teach them how to be great.

• 17:12Ryan Holiday?

  So how do you train for hospitality or train for empathy?

• 17:16Speaker 02

  Well, I think it's about training even more so. I think it's about inspiring. I look at a lot of companies who have such unbelievably great, robust training programs. And yet, training in the absence of inspiration is insufficient. Because it doesn't matter how well you know how to do something. If you're not inspired to want to do it.

• 17:35Ryan Holiday?

  If you don't see it embodied in the people around. It's like, it's more of a cultural value than an individual skill.

• 17:43Speaker 02

  And so I think you inspire it in a bunch of different ways. One, just through words. But I talk so often about the power of a daily huddle with your team and how that is not a time to talk about operational logistics, but rather just to like a locker room speech from a coach, just to get people fired up about an idea. Because passion is contagious. So words, I think, are so meaningful. Showing people what it feels like on the receiving end.

• 18:12Ryan Holiday?

  Yeah.

• 18:13Speaker 02

  I don't think it's possible to know how to be empathetic or to know how good it feels to express hospitality if you first don't understand how good it feels to be on the receiving side of it. I have this belief system that if there was a law passed tomorrow where every one of us was required by law to be remarkably kind to the people that worked at the DMV.

• 18:33Ryan Holiday?

  Yeah.

• 18:33Speaker 02

  That the DMV would now be one of the happiest places in the world to get it. But like, if you're never on the receiving end of something, how could you ever be expected to give it?

• 18:41Ryan Holiday?

  Sure.

• 18:42Speaker 02

  I think feedback, like creating a culture of feedback is so important. And I'm talking about praise, obviously. Celebrating the moments where people do what right looks like.

• 18:53Ryan Holiday?

  Yeah.

• 18:54Speaker 02

  So that they now know what right looks like. Doing that in public so that everyone knows. Because also praise is pretty addictive. The more you get, the more you want to receive. But I'm also talking about criticism. So I think if praise is affirmation, criticism is an investment. And I don't think there are very many things someone can do that are more powerful than stepping outside of their comfort zone for long enough to actually invest in someone else's growth.

• 19:19Ryan Holiday?

  Right.

• 19:20Speaker 02

  Now, that needs to be done thoughtfully. And I, it's actually one of the things I like talking about the most is like the rules of criticism, how to express it in a way that makes it constructive, but.

• 19:30Ryan Holiday?

  Right. It's not screaming at someone how much they suck, or how did you screw this up?

• 19:34Speaker 02

  No, criticism should never be emotional. It should be done in private. You should be sure you are criticizing the behavior, not the individual.

• 19:42Ryan Holiday?

  Yeah.

• 19:43Speaker 02

  You better be willing to receive it as well.

• 19:45Ryan Holiday?

  Sure.

• 19:46Speaker 02

  But all of these things, like it's about inspiring people to believe in something, showing them what right looks like, being there to celebrate them when they do it well, to hold them accountable when they don't. Like, I don't think I could give you like a training manual on empathy.

• 19:59Ryan Holiday?

  Right.

• 19:59Speaker 02

  And also just to lead by example, you know?

• 20:02Ryan Holiday?

  It feels like one of those virtues that's contagious.

• 20:05Speaker 02

  Mm hmm.

• 20:06Ryan Holiday?

  Like, it is easy to be empathetic. It's easy to be hospitable when you see it surrounding you. And then it almost becomes something that you're kind of, not just that you instinctively do, but almost something you're like competitive about, right? Like, in the sense of like, hey, if they did this and that was okay, they didn't get in trouble. In fact, they got praised for going above and beyond. Well, then people are going to take more risks and do more, make an extra effort because they, they understand that that's, that's what we do here.

• 20:34Speaker 02

  I also think like when you've done it a couple of times and you are on the receiving end of what happens when you do.

• 20:40Ryan Holiday?

  Yes.

• 20:40Speaker 02

  Like, this is a, a story that I think validates this. And in 2023, I spoke at the Sundance Film Festival. I don't know if you remember, like, the delays when you traveled that year. We were coming out of COVID. It was pretty bad. That flight was really bad. I think my flight was delayed like seven hours. I didn't get to the hotel until like four in the morning. And I'm pulling up to the hotel like desperate to go to sleep, but gearing up for the whole lengthy check-in process, it's become my biggest pet peeve when I travel. Now is how long it takes to check into a hotel, which I think is well intentioned. Oftentimes they're like, hey, we want to show you around the hotel. We want to give you a map. It's hospitality that's just happening to you, not for you.

• 21:21Ryan Holiday?

  Yes.

• 21:22Speaker 02

  But when I walk in, there's just one guy in the lobby. His name is Oscar. He's the overnight manager. And he's standing there, arm outstretched, holding my room key. And he goes, Mr. Guidara, you must be exhausted. Here's your key. Just go get some sleep. We'll check you in in the morning.

• 21:35Ryan Holiday?

  Wow.

• 21:36Speaker 02

  Small gesture.

• 21:37Ryan Holiday?

  Sure.

• 21:37Speaker 02

  Unbelievably.

• 21:38Ryan Holiday?

  He actually thought about what it was like to be you?

• 21:41Speaker 02

  Well, hold on, hold on, hold on a second. So I go upstairs, fall right asleep. The next morning, I've never been more excited to check into a hotel. And I run downstairs, check in. I find the general manager. I was like, dude, Oscar is unbelievable. You're never going to guess we didn't. Oscar's great. That had nothing to do with Oscar. So what are you talking about? He goes, the delays here have been bad. Couple of months ago, we got together as a team. We said, how can we systemize some graciousness into that moment for people? That's what they came up with. If you got there after two in the morning, they gave you the key. They leave, check in the following day. He goes on to say, Oscar is actually not very hospitable. And I was like, I was like, wait, what are you talking about? He goes, sorry, Oscar was not very hospitable when we started it.

• 22:21Ryan Holiday?

  Yeah.

• 22:22Speaker 02

  Here's the thing, when Oscar did that for me, he wasn't going above and beyond for me.

• 22:26Ryan Holiday?

  That was this, he was falling to the basic level of the process.

• 22:30Speaker 02

  He's following the system that they designed.

• 22:31Ryan Holiday?

  Right.

• 22:32Speaker 02

  But every time he did it, he bore witness to appreciation from people. He got addicted to how that made him feel.

• 22:40Ryan Holiday?

  Right.

• 22:40Speaker 02

  And started finding more and more ways to feel it again.

• 22:44Ryan Holiday?

  Right, the empathy is there in the process of thinking what it is like to be the traveler.

• 22:48Speaker 02

  Yes.

• 22:48Ryan Holiday?

  At that time, they do not want to hear about the, the resort features.

• 22:53Speaker 02

  No, they want to go to bed.

• 22:55Ryan Holiday?

  Yes, exactly.

• 22:56Speaker 02

  But I think my, my point in sharing that is the GM thought he was not hospitable. They did this program. Oscar loved how it made him feel so much. He started finding more creative ways to feel it again. I think everybody has this in them. They just need someone who's willing to do something to inspire it out of them.

• 23:14Ryan Holiday?

  Well, it's also, what is your process? What's your system optimizing for?

• 23:18Speaker 02

  And I think a system can inspire someone.

• 23:20Ryan Holiday?

  You can optimize for thinking about what is actually happening with the person. And then try to set basic procedures that meet that as opposed to retaining systems or processes that are effectively in opposition to that.

• 23:37Speaker 02

  Yeah, it's actually something I was thinking about leading up to this. I was listening to, to some of your stuff over the last week. And here's my question. One of the things I say often, and it has the added benefit of being true, is that there are a few things more energizing for me than when I see the look on someone else's face when they've received a gift I've just given them. Like, I love giving gifts, and most of that is just because I love the act of giving.

• 24:03Ryan Holiday?

  Yeah.

• 24:04Speaker 02

  But I'd be lying if the reaction, like, doesn't fill me up.

• 24:08Ryan Holiday?

  Yeah.

• 24:09Speaker 02

  How does that square with your work?

• 24:12Ryan Holiday?

  How so? What do you think the conflict is?

• 24:14Speaker 02

  The reaction contributing to my contentment.

• 24:20Ryan Holiday?

  Well, it's interesting. I'll have to, let's see if we have a copy, but Seneca wrote this whole essay on, on, sometimes it's translated on giving, sometimes it's translated on benefits.

• 24:28Speaker 02

  Okay.

• 24:29Ryan Holiday?

  I think the Stoics would say it's actually not selfish to do, think about it your way. Like, you're saying like, hey, I, I'm doing this because I want to do it for you.

• 24:38Speaker 02

  Yes.

• 24:39Ryan Holiday?

  Whether you fall down in gratitude to me, or acknowledge it, or whatever.

• 24:43Speaker 02

  Yes.

• 24:43Ryan Holiday?

  Is like, that's on you, but like, I like being this person. And it's good for me to be this generous, kind, empathetic, service-oriented person. The problem is, the vulnerability is if you do it to be liked.

• 24:58Speaker 02

  Yes.

• 24:58Ryan Holiday?

  Or to be celebrated or appreciated. The, the point is to do it because it's good for you and because you like doing it.

• 25:06Speaker 02

  But the question is this, you do it because it's good for you. You like doing it. It is your passion.

• 25:10Ryan Holiday?

  Yeah.

• 25:11Speaker 02

  In allowing the reaction to energize you, in allowing the reaction to bring you joy.

• 25:17Ryan Holiday?

  I don't think there's any problem with that. I think the, I, I say this all the time. This is, this is one of my, I think, few additions to Stoicism, is in, in New Orleans, they have this word, lanyap. You know that word?

• 25:27Speaker 02

  Yes.

• 25:28Ryan Holiday?

  Like, it basically means, like, the 13th donut. It's like, you're, the baker makes the, the 12 donuts, and then they're like, shit, what do I do with this one? And you throw it in the box. I think about it this way, when it's like, you order a smoothie, and the person miscalculates, you either watch them throw the rest of it away.

• 25:44Speaker 02

  Yeah.

• 25:44Ryan Holiday?

  Or they give you a little extra cup, or they give you a larger one, right? What do you do with the extra, that act of generosity or benefit? I think about what you get back from other people or the recognition or the celebration as the lanyap, as the extra. Do I love hearing that my books have changed people's lives? Do I love hearing the sales figures? Do I cash the royalty checks? Of course, all of the above, right? But is that what my sense of success was dependent on? Is that what I was motivated by? If I didn't get it, would I be crushed or resentful? Like, so I think if you're thinking about it as extra,

• 26:21Speaker 02

  Yeah.

• 26:21Ryan Holiday?

  that's great. If it's energizing, great. If it's your fuel, that's a problem.

• 26:27Speaker 02

  Yeah, if I did something for someone else and I didn't get the reaction I expected to or hoped to, I would still be happy that I'd done it.

• 26:37Ryan Holiday?

  The vulnerability the Stoics are trying to avoid is needing the thing that's not in your control. So like, does not getting it deplete you, right? Does, does not getting the Michelin star or the celebration or being included in this list, does that aggrieve you? Does it make you want to throw in the towel? All that is in a world where we don't control what happens and also where things are unfair and often rigged. And there's a delay between recognizing greatness. All of those things, that is, that's a tough way to go through life because you are setting yourself up to be disappointed and frustrated a lot. That's kind of how I think about it.

• 27:17Speaker 02

  One of my dad's quotes that I, has been a very big part of my life is adversity is a terrible thing to waste.

• 27:23Ryan Holiday?

  That's like the definition of stoic philosophy. That's what the obstacle is the way means.

• 27:27Speaker 02

  Yeah.

• 27:27Ryan Holiday?

  Right? Is like, what do you, you didn't control that it happened. It did happen. What are you going to do about it? How are you going to use it?

• 27:34Speaker 02

  The one thing though, like as a leader, if you get to the point where you have really like mastered these ideas, the likelihood is that the people on your team all have not.

• 27:46Ryan Holiday?

  Sure.

• 27:46Speaker 02

  When I talk about adversity as a terrible thing to waste, I realized like a year and a half after the book came out. That I was perhaps leading people in the wrong direction because I wasn't including one important piece. I'd always say like, you cannot control what life throws at you. You can control how you react to those moments, how you, what you learn from them, how you allow them to fuel your competitiveness, all this stuff. And then I heard a couple of stories where a leader of a team, they had a big goal or something and they failed.

• 28:19Ryan Holiday?

  Yeah.

• 28:20Speaker 02

  And the leader went right into cheerleader mode, like, guys, let's not waste this. Da, da, da, da, da, da, da, da. And I think they were missing a crucial step and in doing so, losing the trust of their people, which I believe, you need to give yourself a measure of time to sit in the disappointment with the people that are following you.

• 28:37Ryan Holiday?

  Yeah.

• 28:37Speaker 02

  Because they feel it and they want to know that you feel what they feel in those moments.

• 28:42Ryan Holiday?

  There's actually a story I added to the 10 year anniversary edition of The Obstacle is the Way. Hemingway, his wife is traveling to meet him. Her job was to grab all of his writings.

• 28:52Speaker 02

  Yes.

• 28:52Ryan Holiday?

  And bring it, he was going to show it to this editor in France. She packs up all the stuff, you know, his whole career up until this point, puts it in this briefcase, gets on a train, gets off the train to grab something at a station, forgets.

• 29:04Speaker 02

  Oh.

• 29:05Ryan Holiday?

  She loses everything he's ever written. And there's a famous letter where-

• 29:09Speaker 02

  It just makes my heart hurt.

• 29:11Ryan Holiday?

  There's a famous letter where he's writing to Ezra Pound and he's like, don't tell me this is all for the best. And then I think the operative line is he says, I'm not there yet.

• 29:20Speaker 02

  Yes.

• 29:21Ryan Holiday?

  But within a few months, he's writing again.

• 29:23Speaker 02

  Yeah.

• 29:23Ryan Holiday?

  And he, he looks back, he also, he ends up writing a story about a writer who loses all their writing. And the, the sort of Hemingway style comes, incidentally, from like burning the boats behind him. Not intentionally, but, but I do think it's important that we, that we appreciate that transitional space.

• 29:42Speaker 02

  Yeah.

• 29:43Ryan Holiday?

  The idea of like, your friend comes to you and you have cancer and then you go like, I'm more fat, you love this. Like, I would just never fucking do that.

• 29:51Speaker 02

  Yes.

• 29:52Ryan Holiday?

  And, and in fact, like, one of the weird things about writing about Stoick Velasquez is I end up hearing from people who've just been through unimaginable things or are going through unimaginable things. And they sort of come to me to ask for like thought and I'm like, I'm just not who you're stuck to like I I am not going to pretend that I know anything about this.

• 30:11Speaker 02

  Yes.

• 30:12Ryan Holiday?

  It's easy to just go, yeah, what are you going to do about it? Or, you know, at some level, they're kind of like empty platitudes. And in fact, really dismissive of the reality of what that person is going through. And that doesn't mean this stuff on the other side of it isn't true.

• 30:26Speaker 02

  No, it is.

• 30:27Ryan Holiday?

  They can't work themselves there, but it here, hearing the bumper sticker from you is not going to get them there. It takes some time.

• 30:35Speaker 02

  But and I think it's I think it's not only healthy, but appropriate to just give yourself the grace to fully feel the weight of whatever disappointment you've just experienced. And then say, okay.

• 30:49Ryan Holiday?

  Grief is a great example of this, right? Like if I died, I would feel weird if my family was not sad. Right? Like, like, like, like, I would, I would hope that I had a big enough presence and I was loved enough that they were sad about this.

• 31:03Speaker 02

  Yeah.

• 31:04Ryan Holiday?

  If they were still devastated a year later or two years later, if the mere thought of my name brought them to tears. I'd be like, guys, you're thinking about this all wrong. This isn't what I want. This is like, this is actually saying the opposite of what I think you think it's saying. And so it's like, when you lose someone, it should make you sad. It should be devastating. There should be a giant hole in your heart. But at some point, you transition from that to appreciation and gratitude. And I interviewed this guy. Do you know who David Kessler is?

• 31:32Speaker 02

  No.

• 31:32Ryan Holiday?

  He worked with Kubla Ross on like the five stages of.

• 31:35Speaker 02

  Oh, yeah, yeah, yeah.

• 31:36Ryan Holiday?

  And he, he added a sixth stage and the sixth stage is meaning. Like, how do you have, and this came out of the loss of his son overdosed. And it's like, he.

• 31:46Speaker 02

  After acceptance.

• 31:48Ryan Holiday?

  Yeah, he, he basically had this sort of like exercise, mental exercise. It was thinking about his son is like, his son. Is saying to him, this is what I remember, like, did me dying ruin your life? You know, like, I wouldn't want that. But he's like, did me dying help you help other people? So what do you take?

• 32:07Speaker 02

  Yes.

• 32:07Ryan Holiday?

  But, but like, the idea of saying that to the person at the funeral is obscene.

• 32:12Speaker 02

  Yes.

• 32:12Ryan Holiday?

  So it's that transitionary space. So yeah, you can be the, the leader who encourages and inspires and channels people towards productive uses of this. But you also have to go like, dude, we just got our asses kicked in the Super Bowl. I'll talk to you guys in two weeks.

• 32:29Speaker 02

  Yeah.

• 32:29Ryan Holiday?

  You know, like, I don't.

• 32:31Speaker 02

  By the way, all of that circles back to empathy.

• 32:33Ryan Holiday?

  Sure.

• 32:34Speaker 02

  It's actually knowing what people are feeling, more likely than not, just giving yourself the grace to feel it yourself.

• 32:41Ryan Holiday?

  Yeah. And just because you have decided not to feel it, doesn't mean.

• 32:45Speaker 02

  Or just because you're ready to start responding to it, that doesn't mean everyone else is. And like reading the room, giving yourself time and then making that choice.

• 32:52Ryan Holiday?

  You had some other mottos that I like, I like, of course, you sent like an amazing package with the new book. But I thought there's, this one also very, if, if the one from your father's stoicism, did you know that this was basically the, the favorite motto of the first emperor of Rome?

• 33:08Speaker 02

  No way.

• 33:09Ryan Holiday?

  Yeah. Slow down to speed up. So the motto of Octavian, who becomes Augustus, is a fastina lente, which means make haste slowly.

• 33:18Speaker 02

  Whoa, I love that.

• 33:20Ryan Holiday?

  Yes.

• 33:21Speaker 02

  When I talk about slow down to speed up, there's kind of a couple of different ways it could be interpreted. One, just in the busyness of life, we always used to say, whatever, measure twice, cut once in the kitchen, right? Like that kind of, just like slow down a little bit. But more importantly, one of the things at the core of unreasonable hospitality is just being present.

• 33:43Ryan Holiday?

  Yeah.

• 33:43Speaker 02

  Actually, like focusing so much on the one person in front of you, right now, for me, it is you. That for the next however many minutes we're together, I'm not caring about anyone else in the world and I'm not thinking about anything else I need to do. And these days, I think that's becoming hard even for the best of us to do consistently well.

• 34:02Ryan Holiday?

  Do you know the military version of this one?

• 34:04Speaker 02

  No.

• 34:04Ryan Holiday?

  Slow is smooth and smooth is fast. So it's like, if you've ever hunted, you've ever done anything where like, speed is of the, you're like, it's when you're rushing, your movements aren't smooth, you catch on things, you, you screw up. And so it is this idea of like, slow it down and do it well.

• 34:20Speaker 02

  Yeah.

• 34:20Ryan Holiday?

  And doing it well is fast.

• 34:22Speaker 02

  Yes, and that I think is how it applies to excellence or like achieving the desired result. I think when I talk about just like presence, about just like letting, putting the world on pause.

• 34:33Ryan Holiday?

  Yeah.

• 34:34Speaker 02

  For long enough, you can actually see the person across the table from you. Right? Like, I could still have a good interview with you and be a little distracted, but like, I'm not going to feel as connected to you at the end of it, or I'm probably not going to hear everything you're saying. And I think in hospitality, in relationships and with people, being present and slowing down is one of the best ways to accelerate connection.

• 35:00Ryan Holiday?

  There's a line in Meditations, or Mark's, where it's just saying, concentrate like a Roman and do this thing in front of you as if it is the last thing you are doing in your life. And like, so doing this thing as if it's the last email you send, the last morning meeting, the last time you cook this thing, the last time you carry the plates up, the last time you do the dishes, you know, whatever, big or small, like doing it as if it matters.

• 35:22Speaker 02

  The last conversation you're ever gonna have.

• 35:24Ryan Holiday?

  Yeah, like savor it and then also don't half ass it. Like, you don't get to do another thing. So like, take your time.

• 35:30Speaker 02

  Yeah.

• 35:30Ryan Holiday?

  You know?

• 35:31Speaker 02

  This is it.

• 35:32Ryan Holiday?

  Yes.

• 35:34Ryan Holiday?

  Is a good way to actually do things well. And, and ironically, you end up doing them pretty quickly too.

• 35:40Speaker 02

  Yeah.

• 35:40Ryan Holiday?

  Like, you, you do them as well as they could be done, which is not much longer than it needs to be.

• 35:46Speaker 02

  Yeah, and you might, I mean, maybe you're gonna do a few less things in a day.

• 35:51Ryan Holiday?

  What do you think about that tension? Because I actually have the Thomas Keller line in, in the office. I'll show it to you upstairs, which I borrowed from him, a sense of urgency.

• 35:59Speaker 02

  Yes.

• 35:59Ryan Holiday?

  So how do you balance a sense of urgency with slow down to speed up?

• 36:04Speaker 02

  Well, I think it doesn't mean that once you're done doing this thing, that you just like. Go take a nap on the couch, right? Then you move on to the next task and you keep on going. I think the other way I think about this is I really care about being on time. It like drives me crazy and it used to even more to be late to a meeting.

• 36:23Ryan Holiday?

  Yeah.

• 36:24Speaker 02

  And someone I worked with like was always late to meetings. And that like really drove me crazy because oftentimes we were together in the meeting.

• 36:32Ryan Holiday?

  So yeah.

• 36:33Speaker 02

  Him being late meant that I was going to be late. But I realized that there was something virtuous about his approach. The reason he was late was because he was so focused on the person he was meeting with just before.

• 36:45Ryan Holiday?

  Yeah.

• 36:46Speaker 02

  Whereas me, I would be distracted for the last 10 minutes of one meeting because I was so fearful of being late to the next. And this idea that like, I'd rather be five now, these days, I'd rather be five minutes late to my two o'clock and be present with the one o'clock until the last moment we are together.

• 37:04Ryan Holiday?

  Right.

• 37:05Speaker 02

  And so that doesn't mean I don't have a sense of urgency. Now, the moment that meeting is over, I'm getting right into the next one. I'm going to be fully focused on you. But I would imagine most people would have the same answer that they would rather me be five minutes late to the meeting with them. If I'm going to be a hundred percent present with them the entire time we are together.

• 37:24Ryan Holiday?

  Yeah, it's in Discipline is Destiny, I had two chapter, I did a chapter on having a sense of urgency, like sort of hustle and work quickly and whatever. And then I had a chapter on festina lenta. Cause I think they're, it's not that they're in tension with each other, or maybe they are, they balance each other out. Like you can't be the guy that, that, that jogs to first base.

• 37:41Speaker 02

  Yeah.

• 37:41Ryan Holiday?

  Because you, you don't care that much.

• 37:43Speaker 02

  Yeah.

• 37:43Ryan Holiday?

  And at the same time, if you're running around recklessly or irresponsibly doing some other activity, you're not going to do it well and you're going to have to do it again.

• 37:55Speaker 02

  Or you need to run fast to first base and you also need to wait for your pitch.

• 37:59Ryan Holiday?

  Yes. Right, right, right. You have to have pitch discipline, but then once you make connection with the ball, you go as fast.

• 38:05Speaker 02

  Yeah, exactly.

• 38:06Ryan Holiday?

  But the, the idea of like that perfectionism sometimes being a kind of paralysis. And then also that also like being too fast as an excuse for sloppiness.

• 38:20Speaker 02

  Yes.

• 38:21Ryan Holiday?

  The, the virtue somewhere between the two extremes.

• 38:24Speaker 02

  Yeah, I think, well, I think the success comes because of the tension.

• 38:28Ryan Holiday?

  Yes.

• 38:29Speaker 02

  Not in spite of it.

• 38:30Ryan Holiday?

  Yeah.

• 38:30Speaker 02

  I mean, it's like anything, if I'm at a restaurant and I'm gonna wait 30 minutes for a perfectly cooked entree versus 22 minutes for one that tastes like crap, obviously, I'd rather wait 30 minutes.

• 38:42Ryan Holiday?

  But if you are sitting in the waiting area and you can see that your table is ready and they haven't got you there.

• 38:49Speaker 02

  Or that someone's gotten up and no one has actually busted and reset it. It's like, hey, guys, get out to the table and reset that table as soon as possible.

• 38:56Ryan Holiday?

  That's one of the ways I like, I have a sense of urgency, but the thing I say to people on my team is like, start the clock. Like, the part of it that is in your control, it's gonna take 12 minutes to cook this steak, right? That is unchanging, but if you waste three minutes getting started cooking the steak, you've now made it take 15 minutes.

• 39:16Speaker 02

  Yes.

• 39:16Ryan Holiday?

  And you tell yourself, hey, it takes what it takes, but it didn't take that. Three minutes of that was in your control.

• 39:21Speaker 02

  Yes.

• 39:21Ryan Holiday?

  And so it's like, yeah, look, you don't control how long the diners take once they sit down to when they leave. That's not up to you, but if you don't turn the table over the second they leave.

• 39:31Speaker 02

  You can control how long it takes before you greet them the moment they sit down. One of the things we'd always say is, in a restaurant, this happens in a lot of restaurants. If you sit down at 5:30, like the first seating, and you watch how the staff moves through the room, and then compare that to how quickly they're moving through the room at 8:30.

• 39:49Ryan Holiday?

  Yeah.

• 39:50Speaker 02

  5:30, they're moving far too slowly. And at 8:30, they're effectively running around the room.

• 39:56Ryan Holiday?

  Right.

• 39:57Speaker 02

  And so our whole thing, I would say it many, many nights in premium, is start moving the same speed you will be moving in three hours. And effectively, you end up splitting the difference. You're moving more quickly at the beginning.

• 40:08Ryan Holiday?

  What's your pace? And how do you have the discipline to stay at the pace even when there's not pressure? And then when there's too much pressure?

• 40:14Speaker 02

  Yes, and, and by the way, when you do that, it's less likely that there ever will be too much pressure.

• 40:19Ryan Holiday?

  Right.

• 40:19Speaker 02

  Because you're staying on top of it from the beginning. The added benefit is also in a restaurant, and I think this applies to other environments, when the people start to speed up, that's when, as a customer, you feel like things are going off the rails.

• 40:33Ryan Holiday?

  Right.

• 40:33Speaker 02

  If they're always moving at the same pace, you think that things are always in control, even in the moments where they might not be.

• 40:39Ryan Holiday?

  And that's what festina alenta is. It's the sense of, of setting the pace as opposed to being hurried or.

• 40:48Ryan Holiday?

  Not hurt like you're like I'm I'm deciding the speed like as a runner you learn this it's like you have to be running at the pace you set for yourself and if there's people pressuring you you can't let that rush you because they could be running at a different pace they could not know what they're doing and conversely just because there's nobody behind you doesn't mean you take your foot off the gas like can you be sort of self regulating about the speed that you're operating on independent of the environment.

• 41:17Speaker 02

  The situation does not drive your your actions.

• 41:20Ryan Holiday?

  Yes.

• 41:32Ryan Holiday?

  I was surprised you didn't have a card on this one because it's one of my favorites and you you do have it in the journal. How you do anything is how you do everything. And you were talking another Thomas Keller one which I loved that when they use masking tape to label like dishes or supplies or whatever they have to cut it with scissors. It shouldn't matter at all just masking tape is designed to be torn easily. But for some reason he's insisting that you cut it. Why is that?

• 41:56Speaker 02

  I mean, in their kitchens and we copied it, you'd cut the masking tape in my dining room, we would put, do you know where the charger is?

• 42:04Ryan Holiday?

  No.

• 42:04Speaker 02

  Charger is the plate that's on the table in a fine dining restaurant already when you sit down.

• 42:08Ryan Holiday?

  Yeah.

• 42:09Speaker 02

  Which means that's a part of setting the table in the beginning of service before anyone arrives and in a nice restaurant, you may or may not be someone that does this, people will pick up the plate to see who made it. They're like, oh, my gosh, I like this plate. Who made it? And so we would set the chargers so that if I ever picked it up like this, I don't know how to describe that for people not watching, but the logo would be facing me perfectly.

• 42:33Ryan Holiday?

  Right.

• 42:35Speaker 02

  Which meant that you look at it and then you place it down. Now, let's just break this down for a moment. How many people are actually going to pick up the plate? Maybe 5%? How many people are going to pick up the plate exactly like that?

• 42:48Ryan Holiday?

  And you're saving them.

• 42:49Speaker 02

  Yeah, maybe 5%. How many people who pick up the plate and pick it up in the way that we imagined they would pick it up are even going to notice that the logo is facing you perfectly?

• 42:58Ryan Holiday?

  Sure.

• 42:58Speaker 02

  Maybe 5%. So an extraordinary amount of energy.

• 43:01Ryan Holiday?

  And then appreciate it.

• 43:02Speaker 02

  That's my point.

• 43:02Ryan Holiday?

  0%.

• 43:03Speaker 02

  Yeah, like a fraction of a fraction of a fraction.

• 43:05Ryan Holiday?

  Yeah.

• 43:06Speaker 02

  It's not for them.

• 43:07Ryan Holiday?

  Right.

• 43:08Speaker 02

  I think that in, it's not dissimilar to what we were just saying about you begin moving at the pace you want to move. It's about setting an excellence mindset in the room the moment people are set in the tables and that pursuit of excellence carries through the entire night.

• 43:24Ryan Holiday?

  Yeah.

• 43:25Speaker 02

  I think anytime as a leader, you can create mandated practices at the beginning of a day that just shift people into an excellence mindset that always pays dividends throughout the entirety of the day. And the same is true in cutting the masking tape. That is something you do at the beginning of your shift. And so, yeah, the way you do one thing will be the way you do everything. It is, there are exceptions to this. There are people who have extraordinarily messy offices and somehow have an organized mind.

• 43:53Ryan Holiday?

  Sure.

• 43:53Speaker 02

  And yet they're few and far between.

• 43:55Ryan Holiday?

  Yeah, it's like, aren't the inside of Apple products beautiful?

• 43:59Speaker 02

  Mm hmm.

• 44:00Ryan Holiday?

  And Steve Jobs said he learned that from his father, who's a carpenter, who said like, no, the back of the cabinets matters too.

• 44:06Speaker 02

  Yes.

• 44:07Ryan Holiday?

  And it is interesting, like, you find, like, because I'm not in that, like, if I was working on a project, like woodworking, my workshop would be a mess. You know, it would be a disaster because that's not my crap. I don't care about that profession.

• 44:19Speaker 02

  Yes.

• 44:19Ryan Holiday?

  But then you meet someone who does and they're like, no, we're gonna have a construction clean come in afterwards. And like, they really, like, the best ones, the ones you can really count on, the ones that you, that won't screw you over are the ones that care about those little details because it doesn't actually have anything to do with you. It's their respect for the thing. It's like the, the baseball player that doesn't cheat the game.

• 44:41Speaker 02

  Yes, 100%. You know who Tom Sacks is?

• 44:44Ryan Holiday?

  Yeah, he's an artist, right?

• 44:45Speaker 02

  Yeah, have you ever seen his, like, it's a video and there's also a little book. I think it's called 11 Bullets.

• 44:50Ryan Holiday?

  No.

• 44:51Speaker 02

  You got it.

• 44:51Ryan Holiday?

  Okay.

• 44:52Speaker 02

  You have to get this little booklet. You'll love it. And it's effectively their, like, employee manual.

• 44:56Ryan Holiday?

  Yeah.

• 44:57Speaker 02

  And it's like these rules of what you're required to do if you work in their studio. And one of them is always be gnawing. And I don't know that, I'm not sure where the word gnawing came from, but basically it means like tidy up everything always because it, and it's not about, like, is the art gonna be better because your desk is well organized? No, what it is, is respect. The space that we create art within.

• 45:23Ryan Holiday?

  Yes, I think it was Proust had this thing about how the more disciplined you are in the stuff that's not the work, the more extreme and experimental you can be in inside the work, which is ultimately where it matters.

• 45:37Speaker 02

  Yeah.

• 45:37Ryan Holiday?

  Right? Like, having the messy studio doesn't help anyone.

• 45:41Speaker 02

  But the balance there, like for me, if I'm gonna like start to write, if I'm writing my newsletter, or if I'm writing whatever, or doing any sort of creative exercise, I kind of need everything to be perfect before I can focus, and that can be an excuse for procrastination.

• 45:57Ryan Holiday?

  Sure. The resistance for you is manifesting in, we'll do all these other things before the conditions are right.

• 46:03Speaker 02

  Exactly. But I need to be careful. It's like, bro, okay, let's calm down a little bit. Like, you can just sit down and write now.

• 46:08Ryan Holiday?

  Yes. Yeah, I think the founder of Rolls Royce had this like Latin motto on his mantle, and it was like, you know, whatever done rightly, however humble, is noble. And you think about, oh, yeah, that's why, you think about the details that would go into a Rolls Royce, like, if you do the thing right.

• 46:25Speaker 02

  However humble the part of the process is.

• 46:27Ryan Holiday?

  Yes, exactly. Which actually tied to one of the other ones you had, which is, uh, there's nobility in service. Like, anything that you do well, anything that you take seriously, and especially if you do it over and over and over again, it takes on a kind of a, uh, an element of majesty and grace.

• 46:45Speaker 02

  Yes.

• 46:46Ryan Holiday?

  Even if it's shining people's shoes, or opening car doors, or, you know, washing the, washing the dishes.

• 46:53Speaker 02

  I mean, the nobility of service also takes that in to a different place, which is, yes, everything you just said is true, and whatever it is that you do, I believe you need to name for yourself why there is importance in it.

• 47:06Ryan Holiday?

  Yeah.

• 47:07Speaker 02

  And then if you lead others, you better re-articulate that reason, that nobility, over and over and over again, because I don't care how much you like your job, let's name it, sometimes work sucks.

• 47:21Ryan Holiday?

  Yeah.

• 47:22Speaker 02

  And if you don't know that there's inherent importance, and I believe you can ascribe nobility and importance to literally everything. If you if you search hard enough for the words.

• 47:32Ryan Holiday?

  I'm really glad you said that because it's really easy to take whatever it is that you do. And just start to see it as like a bunch of obligations or a bird like I just did this TV thing this morning. And so that like a bunch of orders came into the bookstore and like so like that's like hundreds of books that they have to package and send out, right? And so it's like, it can be very easy to be like, oh, you know, like this is books to go at the shelf, books to go in the envelope, papers to print out, envelopes to seal, thing to drive down the street to the post office, right? And the other way to think about it is like, we love these books and now people are going to read them. And like, also like, this was from a cable news thing I did. Why did these people order the books from us?

• 48:16Ryan Holiday?

  Like they they did something awesome for like they instead of pulling up their phone and ordering it from Amazon, which is easier and faster and cheaper.

• 48:25Speaker 02

  Yes.

• 48:25Ryan Holiday?

  They did us the service of typing in the name of our bookstore and ordering it from us. Even though on every one of those things.

• 48:34Speaker 02

  Credit card and doing all this stuff.

• 48:36Ryan Holiday?

  Yeah, exactly. Like, Amazon has their information saved. Amazon is cheaper. Amazon doesn't pay shipping.

• 48:42Speaker 02

  Amazon will be there in 30 minutes. They're going to be a back rub when they.

• 48:46Ryan Holiday?

  Exactly. Like, I try to remind people, like, every one of the people that ordered a book from our bookstore online did the least efficient, like, least easy for them option. Like, it's not an act of charity, but it was an act of kindness. Kindness is even right. It was an expression of support.

• 49:05Speaker 02

  Yes.

• 49:05Ryan Holiday?

  Right? Like, you have to take that seriously. So when I get upset with my, it's like, hey, guys, I signed this book for this person on Friday afternoon at 2:00. And by you not packaging it by 4:15 PM, that meant that it didn't go in the mail for that person until Monday at 4:00 PM. Because that's the next shipping one. And so you said to that person, even if they don't care and they're not going to complain, you said to that person, hey, I'm going to make you wait for four extra days.

• 49:35Speaker 02

  Yeah.

• 49:35Ryan Holiday?

  For no fucking reason. And that I don't accept that.

• 49:39Speaker 02

  I mean, by the way, now we go back to sense of urgency.

• 49:43Ryan Holiday?

  Yeah, totally. That's why it's up on the wall because I caught that too many times. And I was like, hey, you guys are just thinking you have time, but it's not your time that you're wasting.

• 49:53Speaker 02

  Well, urgency, like with that sort of thing, whether it's even, I'm sure you've experienced this in the same way. The busiest people in my life are always the quickest to respond to a text.

• 50:01Ryan Holiday?

  If you want a response, send it to a busy person.

• 50:03Speaker 02

  And because they understand that, like, actually, like, being timely in a response or being timely in sending out a book, it just shows that you actually respect the person enough to.

• 50:12Ryan Holiday?

  Or that you have your shit together.

• 50:14Speaker 02

  But back to the thing before, yes, boxing up a ton of books, that's not the fun part of the work. No one took a job at this bookstore because like, you know what I want to do with my life? I want to tape boxes, right? And yet, of course, to your point, you need to feel a sense of gratitude in those moments because, yeah, someone is supporting you when they could have done so much easier. But also, like, when I talk about nobility, you could say we sell books.

• 50:37Ryan Holiday?

  Right.

• 50:38Speaker 02

  But it's more than that. You're either selling someone inspiration or education, or simply giving them the gift of putting the world on pause and having an escape in a book that maybe gives them respite from a really difficult moment that they're going through. Like, there's so much more nobility in everything. You could be driving down the street, picking up people's dirty garbage, or you could actually be helping civilization, like, stay alive, right? And I just think the reframe is necessary in order for us to be able to bring our most fully realized selves to the table.

• 51:11Ryan Holiday?

  Well, it kind of comes also back to empathy, like actually thinking about the person on the other end of this exchange. It's not just like, oh, I'm abdicating myself by thinking about them. Actually, what you're getting is some kind of reflected meaning back. Do you serve a plate of calories to people? Or is this like a meal where, like, a family comes together? You know, where people got engaged, where they're on a graduation trip? Like, are you thinking about the person and what they're bringing to it and what this means to them? Or are you thinking about it as like a meaningless exchange of monetary value in the middle of a otherwise meaningless life? Yeah.

• 51:53Speaker 02

  Don't we all want to do something that is important?

• 51:56Ryan Holiday?

  Sure.

• 51:56Speaker 02

  And, and I think just taking the time to identify for yourself why there's importance. And yes, you need empathy in order to get there.

• 52:02Ryan Holiday?

  Yeah, it helps you go, oh, okay, this actually isn't an insignificant, meaningless thing. Like, I'm helping you do a thing that, like, I just had this terrible customer service experience with this doctor thing I was going through. And like, there was some miscommunication or whatever, and she was like, the person was upset with me. But I was like, did you forget that, like, I'm a patient, like, I'm here on a sensitive medical thing and you're a doctor?

• 52:28Speaker 02

  Yes.

• 52:29Ryan Holiday?

  There's no version of this where I have an obligation to you. Like, you have an obligation to me. You're a professional in this thing who deals with this all the time. This is my first time and only time dealing with this thing. And you're frustrated that this, like, miscommunication happened. And so it's like, what you lost is thinking about who I am walking into your office.

• 52:53Speaker 02

  And also, why did you decide to do this with your life in the first place?

• 52:57Ryan Holiday?

  Totally.

• 52:58Speaker 02

  Reconnect with that version of you.

• 53:01Ryan Holiday?

  Yeah.

• 53:01Speaker 02

  And it'll help you, I'd imagine, not only be better at this now, but derive a whole lot more pleasure from doing it.

• 53:07Ryan Holiday?

  Yes. And then, though, to go to the other thing, which I do think about as stoic, the idea of like adversity is a terrible thing to waste. It's not always an economic downturn or like a cancer diagnosis or some huge thing. I was like, this woman is totally wrong and she's being a jerk. And I was like, can I not, like, what I said to myself as this is happening, I was like, do you think I could get out of this appointment without getting upset? I was like, the thing for me is like, I'm not going to get upset. I'm like totally justified in throwing it back at this person and escalating it potentially. But I'm just like, I'm not going to do that. I was like, I'm just going to weather whatever this storm is. I'm going to get the information that I need. And then afterwards, I'm going to be like, hey,

• 53:53Ryan Holiday?

  That person was rude and I was not rude in return.

• 53:56Speaker 02

  Yes.

• 53:56Ryan Holiday?

  That's a big win.

• 53:57Speaker 02

  Yes.

• 53:57Ryan Holiday?

  That's what I got. That was the, actually the gift that they gave me was that like, I got a rep in not.

• 54:05Speaker 02

  Not being reactive.

• 54:06Ryan Holiday?

  And not being a person I don't want to be. Like at the end, if I was like, fucking excuse me, like, you know, like, what is this? You know, or what? Like, I wouldn't leave that later and then like, I'm so glad that that happened.

• 54:18Speaker 02

  You lose and that like.

• 54:19Ryan Holiday?

  I was so crappy also.

• 54:21Speaker 02

  The, the, the thing that's been, I think is so helpful in those moments in leadership and service or in just moving through life. As this story entails is something that came from my former boss, forever mentor Danny Meyer.

• 54:34Ryan Holiday?

  Yeah.

• 54:35Speaker 02

  Charitable assumption.

• 54:36Ryan Holiday?

  Yes.

• 54:37Speaker 02

  Which effectively means give people the benefit of the doubt in that moment. Like what we would say in the restaurants is when someone comes in and they're acting like a jerk.

• 54:47Speaker 02

  Okay, obviously we're not going to be a jerk back to them there in our restaurant, but it is totally reasonable to say, this person no longer deserves our greatest hospitality.

• 54:57Ryan Holiday?

  Yeah.

• 54:58Speaker 02

  The charitable assumption, however, would compel you to look at it in this way. Maybe they're acting like a jerk because on their way to the restaurant, they just heard that their wife was cheating on them or someone in their family died. And maybe the person acting like a jerk actually needs our love right now more than anyone else in the room. Now, sometimes they're just actually a jerk.

• 55:19Ryan Holiday?

  Yes, yes, yes, yes.

• 55:20Speaker 02

  But I obviously always rather err on the side of assuming the best and being wrong than the alternative. And that's a helpful thing for me in those moments because maybe the doctor, just something terrible happened in their lives. And when you think about it like that, it's less of a challenge to be like, you know what?

• 55:39Speaker 02

  I'm just gonna be nice right now.

• 55:40Ryan Holiday?

  Or just, I'm just not gonna be not nice, right?

• 55:43Speaker 02

  Yes.

• 55:43Ryan Holiday?

  Like, I think obviously when you're, when it's in your sort of core element of competency, like it's in your restaurant. It's like, hey, can we give amazing service to a person who doesn't deserve amazing service?

• 55:52Speaker 02

  Yes.

• 55:53Ryan Holiday?

  I don't necessarily know if you need to go through that in all areas of your life. It's just to me, like what the Stoics are saying is like, just don't let an asshole make you an asshole. Like the win is. Just not being dragged down to the level. And so it's like, I'm gonna stay, you're here for some reason. I'm not gonna get there also. I'm somehow saying hi. So it's a high position. But it's like, you're at a 10 and I walked in at a five. This is a totally normal situation. By not getting to a 10, that's a win. I'm just gonna stay at my level.

• 56:22Speaker 02

  Wherever you are in that moment.

• 56:24Ryan Holiday?

  Yeah, I'm gonna kind of honestly, I'm just like, whoa, okay. Like I found myself just saying over like, I was like, you know, like, okay, so which model is this? And she's like, and I go, like, you know, like, I was like, I just want to know this so I can, you know, and then I just kept asking the questions I needed to get the information that I needed to do what I was doing. But I didn't need to like, I don't need to dunk in this person. I don't need to call this person. I don't need to win. And honestly, I don't really care what you're going through to go to the point that empathy, it doesn't have to cripple you. It's like, clearly something is happening and I hope your family deals with it, but like, I'm just not gonna, I'm not gonna be a person I don't want to be.

• 57:04Speaker 02

  Yes.

• 57:04Ryan Holiday?

  Because you're not being the person you want to be.

• 57:07Speaker 02

  No, I mean, on the receiving end in customer service, obviously this is my entire life.

• 57:13Ryan Holiday?

  Yes.

• 57:14Speaker 02

  And so when I'm on the receiving end of just like, it drives me nuts. How we as an entire culture have seemingly fallen out of love with the words, I'm sorry.

• 57:26Ryan Holiday?

  Yes.

• 57:27Speaker 02

  You know, like when someone makes it like, just please say, I'm sorry. And if I'm not careful, I will let it really grate me or I in some cases will almost be encouraged to be like, excuse me, you realize you're doing this all wrong. Like I actually wrote a book about it.

• 57:43Speaker 02

  And what you're saying is right. Like whatever you're at, like, it's just giving away your power to.

• 57:48Ryan Holiday?

  Totally. And if that's how you go through life, if you go through life as this kind of open wound, it's gonna break you. Do you know what I mean? Like, like also the funny thing is like, I need you to make this right or what? It's like, do you though? Like, are you gonna have a positive experience all the time everywhere you go? Like, I feel like as I've gotten older, gotten more in control of myself, I try to be better at just like, this isn't, sometimes shit just sucks.

• 58:11Speaker 02

  Yeah.

• 58:11Ryan Holiday?

  You know what I mean? Like, I shouldn't, that's not the standard I hold myself to. But I think I've gotten better at not expecting perfection or even hospitality for most of the encounters that I have. Because that's like, it's not probably gonna happen. And also the expectation of it sets you up for disappointment and frustration.

• 58:30Speaker 02

  I mean, I think one of the greatest things about what I talk about and write about is it from a business perspective. It's the greatest competitive advantage.

• 58:39Ryan Holiday?

  Totally. It makes you stand out.

• 58:40Speaker 02

  Because it is not the norm. And not only does it make you stand out, but like when you invest in relationships, they take a long time to build. And when you build them the right way, they take a very long time to erode.

• 58:51Ryan Holiday?

  Yes.

• 58:51Speaker 02

  And we've almost become like starved for those moments when someone is willing to go above and beyond for you. And so when someone does, gosh, it feels so good.

• 59:05Ryan Holiday?

  In a way, it's like you think about, you think about what companies spend to buy the naming rights to a stadium. Or to run these stupid billboards or boring ads. And you go like, what could you, what could you do with $200 million?

• 59:20Speaker 02

  Imagine.

• 59:21Ryan Holiday?

  Like, imagine what you could do with that. And I don't just mean like, how many, you know, starving children in Africa could you support? I just mean like, what kind of, how much better could your product be for how many people?

• 59:33Speaker 02

  Are just doing cool things for people. Like I would say that every dollar I've ever spent on hospitality has been far more impactful than any dollar I ever spent on marketing. Because when you give people stories to share, they're going to share them over and over and over again. The other example of that, I think company, like the big companies dramatically overspend on nonsense, like what you just talked about. And dramatically underspend on guest recovery, like actually recovering.

• 1:00:01Ryan Holiday?

  Yes.

• 1:00:01Speaker 02

  The customers with whom they've messed up. There's all this data. If you come into my business and you have a good time, you're going to talk about it so much. If you come in, you have a bad time, you're going to talk about it a lot more.

• 1:00:12Ryan Holiday?

  Yeah.

• 1:00:12Speaker 02

  But if you come in and you have a bad experience and then I do whatever it takes to turn it around, you're going to talk about it the absolute most, like an order of magnitude more than the other two.

• 1:00:24Ryan Holiday?

  It's also so much more effective to expand the business you have with a customer.

• 1:00:29Speaker 02

  Yes.

• 1:00:29Ryan Holiday?

  Than it is to acquire a new customer. And the problem is one is much more measurable. Like, it's like, hey, this billboard costs $1,000.

• 1:00:41Ryan Holiday?

  And

• 1:00:41Speaker 02

  It will get this many eyeballs over this amount of time.

• 1:00:43Ryan Holiday?

  Exactly. That is very

• 1:00:45Speaker 02

  Standard conversion rate of people that look at a billboard.

• 1:00:46Ryan Holiday?

  Exactly, like, but just doing what you do well and growing your really, all that stuff feels a little sort of woo woo and immeasurable and whatever. So it gets neglected.

• 1:00:58Speaker 02

  We get so focused on investing only in the things that we can measure that I think we're under investing on the things that actually have the greatest impact.

• 1:01:06Ryan Holiday?

  Well, and then also the things that matter, like what, one of the decisions I made with my business is I was like, I was like, wait, this is what we're spending on like Facebook ads? I was like, the net impact of this on society is not positive in any way. And then at the end of my life, I'm not going to go back and I, I spent cumulatively this much on advertising. And, and that will live on past me, right? Like it's, you're, you're spending a dollar to make a dollar 25, right? And that math is great. And if, if all you care about is numbers, awesome. But I was like, okay, but if I spend a dollar, obviously you don't

• 1:01:44Ryan Holiday?

  literally spending a dollar, but let's say it's a $65,000 advertising budget or a $65,000, like I'm going to hire another copywriter or a creator or whatever. I'm going to make more stuff.

• 1:01:58Speaker 02

  Yeah.

• 1:01:58Ryan Holiday?

  Like, not only am I actually supporting a human being,

• 1:02:01Speaker 02

  Yes.

• 1:02:01Ryan Holiday?

  which is great, but like the stuff that we make together exists after we make it. It exists forever.

• 1:02:08Speaker 02

  If you don't get those Facebook ads, like what is Zucker, like, how is he even afforded?

• 1:02:12Ryan Holiday?

  But it's like, it was like, hey, do I want to spend my money on ads or do I want to spend my stuff on content that one is creatively fulfilling to make, but then actually delivers value for people?

• 1:02:22Speaker 02

  Yeah.

• 1:02:22Ryan Holiday?

  How do you, how do you want to think about what you do?

• 1:02:25Speaker 02

  And now it's different for like, for some people, I remember when I, when I talked to people who were writing their first book, I was like, hey, like writing the book is kind of the sprint before the marathon.

• 1:02:34Ryan Holiday?

  Mm hmm.

• 1:02:35Speaker 02

  Because if, if you wrote a book and you don't do whatever it takes to get it out into the world, then like, what was the point of writing it in the first place?

• 1:02:42Ryan Holiday?

  Sure.

• 1:02:43Speaker 02

  And so like, I think in the beginning, some of that stuff is important, not just for money, but just to like get an idea.

• 1:02:48Ryan Holiday?

  I mean, marketing matters, but I'm saying making content is marketing, right? It's better marketing than.

• 1:02:53Speaker 02

  Oh, you're saying like a newsletter?

• 1:02:55Ryan Holiday?

  Newsletters or videos or articles and like, I want to make stuff that's free, by the way, and that people enjoy, and then it brings them into the universe. Like, you know, the basic marketing funnel. Do you want the top of the funnel to be advertisements? Or you want the top of the funnel to be stuff that you think is good, that you put out into the world?

• 1:03:13Speaker 02

  No, I'm with you.

• 1:03:14Ryan Holiday?

  So that's what I think about. Speaking of which, you want to go check out the bookstore?

• 1:03:17Speaker 02

  I would love to check out the bookstore.

• 1:03:18Ryan Holiday?

  All right, let's do it.