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DJ Envy
This is an iHeart podcast.
Ashley Nicole Moss
Wednesday at 10, 9 Central on BET. An all new episode of 106 in Sports from executive producers LeBron James and Maverick Carter. It's a new top five countdown with hosts Ashley Nicole Moss and Cam Newton. They're breaking down the top moments in sports, culture and entertainment and highlighting both established pros and the stars on the come up. Watch the all new series 106 in sports Wednesday at 10, 9 Central on BET or catch up the next day on BET.
Charlamagne Tha God
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Johnny Knoxville
Johnny Knoxville here. Check out Crimeless Hillbilly Heist, my new true crime podcast from smartless media, campside media and big money players. It's the true story of the almost perfect crime and the nimrods who almost pulled it off.
Ryan Holiday
It was kind of like the perf storm in a sewer. That was dumb. Do not follow my example.
Johnny Knoxville
Listen to Crimeless Hillbilly Heist on the iHeartRadio app, Apple Podcasts or wherever you get your podcast.
Hell in Heaven Narrator
Two rich young Americans move to the Costa Rican jungle to start over. But one of them will end up dead and the other tried for murder three times. It starts with a dream, a nature reserve and a space. Spectacular new home. But little by little, they lose it.
Ryan Holiday
They actually lose it. They sort of went nuts.
Hell in Heaven Narrator
Until one night, everything spins out of control. Listen to hell in Heaven on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
Charlamagne Tha God
Every day I wake up.
Ryan Holiday
Wake your ass up.
Lauren LaRose
The Breakfast Club.
Ryan Holiday
Y' all finished or y' all done?
Charlamagne Tha God
Morning, everybody. It's DJ Envy. Just hilarious. Charlamagne the guy. We are the breakfast club. Lauren LaRose is here as well. We got a special guest in the building.
Lauren LaRose
One of my favorite authors ever.
Charlamagne Tha God
He has a new book, Wisdom Takes work. Learn, Apply, repeat. Ladies and gentlemen, Ryan Holiday. Welcome back.
Ryan Holiday
Thanks for having me.
Charlamagne Tha God
How you feeling this morning?
Ryan Holiday
Doing awesome.
Lauren LaRose
What book is this number?
Ryan Holiday
What I don't know.
Lauren LaRose
You don't even. 10 to 10.
Ryan Holiday
It might be 15, 16, something like that.
Charlamagne Tha God
Damn fifth or sixth time he's been up here.
Ryan Holiday
Yeah, very good to me.
Lauren LaRose
Yeah, no, we like having you, man. The wisdom takes work, learn, apply, replete, repeat. And in the book you argue that wisdom is the virtue on which all other virtues depend. How did you arrive at that belief?
Ryan Holiday
So the four virtues of Stoic philosophy which I write about are courage, discipline, justice and wisdom. They're all separate, but they're related in that, you know, wisdom tells us when and how to apply the others. It doesn't matter how good your heart is if you don't have the wisdom, the intelligence to know how to bring it into the world. Or courage is important, but you could be courageous for something real dumb. So wisdom is the sort of layer on top that we have to apply to all our other skills and assets.
Lauren LaRose
Well, is one thing to do, to research. Was there a specific moment in your.
Ryan Holiday
Life that made you realize that that wisdom was important? Yeah. Well, you know, I think we've all met some smart people that do dumb things, and I think we've all done dumb things. And you look at wisdom as being the sort of the key to not just a successful life, but a good life, Right. You can be really good at what you do and then you can blow it all up or you can be profoundly unhappy or, you know, how many smart people are lacking in self awareness? So I just think wisdom is this sort of piece that brings it all together. And I think one of the problems is that we assume wisdom is this thing that just happens, right? We go, sure, school is important, but you know, experience is important. You know, wisdom comes with age, not it's no guarantee. I met a lot of dumb old people too.
Lauren LaRose
Absolutely. I was always taught smart people learn from their own mistakes. Wise people learn from the mistakes of others. I completely agree that wisdom is a lost art. I think you have a lot of smart people. I don't think you have a lot of wise people nowadays.
Ryan Holiday
Yeah, yeah. And I mean, you need this not just to be successful, as I was saying, but like, how do you not fall for demagogues or how do you not fall for scams? How do you rise above the noise? How do you separate fact from fiction? Wisdom, I think, is, you know, there's this word discernment, right? Art of discernment. Like how many people can really see the difference between good and really good, you know, right? And almost right. Truth and complete nonsense. That to me is the missing Skill of our time.
Lauren LaRose
We're doomed. Guys, it's over. Pack it up. Go home.
DJ Envy
We're not doomed.
Lauren LaRose
Yes, we are.
DJ Envy
No, I think. I think everybody eventually has something in their life that wakes them up to that, whether it's at a different. Like, might be young, might be older. But you always taught. You're always taught that, like, wisdom comes with age. Yes, that saying. So you probably hate that saying, huh?
Ryan Holiday
Yeah. Churchill was joking about this guy he didn't like, and he said that although he occasionally stumbled over the truth, he quickly picked himself up and carried on as if nothing had happened. Right. So people are. I think life is always teaching you. Right, but you don't have to hear it. And so life will sometimes whisper. Life will tell you nicely things that you need to know. And then when we ignore that, it becomes louder and louder and louder until sometimes, you know, you have to learn from some kind of catastrophic failure or catastrophe. And so your point, that we can learn from the experiences of others, that's the cheap, effective, efficient way to do it. And then a lot of us go, no, no, I'd rather figure it out on my own. And that costs. Not just them, but the people around them. When we're late to learning lessons, that doesn't just affect us, but that affects the people that work for us. That affects our family. That affects the people who, you know, bear the consequences of that, you know, painful lesson that we chose to learn the hard way.
Charlamagne Tha God
I think wisdom has to come from age, though.
Ryan Holiday
Sure.
Charlamagne Tha God
Regardless. I mean, regardless of what the. You could meet a stupid old person, but there is some wisdom that comes from what they're doing. Whether if they work at a plant, whether they. Whatever they do at the house, there is some type of wisdom that they can continue on to give to somebody else.
Ryan Holiday
Well, you know, the root of the word idiot is somebody in ancient Greece who did not participate in public life. So you can read everything you want, and you can read a lot, and that'll make you smarter than the average person. But if you're not engaged and involved, you're gonna miss some things that you can only learn from experience. Da Vinci would sign his letters a disciple of experience. You have to learn by doing. You have to put yourself out there. And that's why I say it's learn, apply, repeat. So you learn the things you hear, the lessons you. You study, you go to school, then you got to go out in the world and you find that. That a lot of what you learn now has to be applied, or a lot of what you learned you didn't actually understand it. And then you repeat that cycle over and over and over again. And each time that that's a positive feedback loop that's making you smarter and better.
Charlamagne Tha God
They talk about education a lot of people, and I'm seeing this a lot more and more and more that people are not necessarily wanting to go to college.
Ryan Holiday
Sure.
Charlamagne Tha God
They feel like the. The education that they get in college, they can be taught more through life experiences, and they feel like the wisdom that those professors have might be outdated, what they're teaching. What's your thoughts on that?
Ryan Holiday
Well, look, I'm a proud college dropout, so I'm all about it. There is and always has been a difference between school and education. So. So I think the problem is, if you don't know what you're trying to do, how do you know what the best form of schooling or education is for you?
Charlamagne Tha God
I say that all the time, by the way. I think it's stupid that we force kids to get out of high school and say, go to college and pick a major immediately when they don't necessarily know what they want to do. If you know what you want to do, that's great. But there's been times where kids were like, I don't know, don't make me pick a major and make me take these courses if I don't necessarily know what I want to do in life.
Lauren LaRose
And by the way, nowadays, when we live in a world where we're kind of preparing for a future that won't even even exist because the AI going to be having all the jobs that.
Ryan Holiday
You wait well, and look, spending a couple hundred thousand dollars over four years is an expensive way to figure out what you want to do. Absolutely. Especially if at the end of it, you find out that what you want to do is something that didn't require college. For. For me, I met Robert Greene, our mutual friend, and then I realized that's what I wanted to do. And then I said, well, am I going to keep going to college, or am I going to go directly learn from the person who's done it? So I'm a big believer in apprenticeships and mentorships. You got to find your teachers. Sometimes those are college professors, sometimes they're business executives, sometimes they're, you know, your neighbor down the street. But you got to find who can teach you how to do what you want to do.
Lauren LaRose
When you started off as an apprentice with Robert Greene, one of the first things he put you on was 40. A lot of power, right?
Ryan Holiday
No, I've worked on the 50th law.
Lauren LaRose
50Th.
Ryan Holiday
Like, the first thing I did was transcribe before in a world before AI. I transcribed hours and hours of interviews between him and 50. And so that was part of my education. It's just listening, not just listening to it, but having to painstakingly type it all out. And so I got this masterclass. And not just how he worked, but all the people around him. But what I was actually learning was like how you put a book together. And Robert showed me how to research a book and how to write and then how to operate. In the industry, you want to find the people who are further ahead in what you want to do and do it. Although, to be fair, like in college, I think one of the most professors are professionals in what they do. They're not just teachers, they're researchers, they're experts. They're, you know, they had a previous experience where they did the thing. And, you know, every week they have office hours where they have to sit there and meet with the students and nobody comes. So I thought the crazy thing for me is like, I didn't go into the library at my college until after I dropped out and I was writing my first book because I was like, oh, wait, this is an incredible free resource that I was too busy, you know, doing the college kid thing to take advantage of. So all this stuff is there. It's just you gotta be self directed.
Lauren LaRose
And self motivated, you know, in Wisdom Takes Work, you write that we live in an age where reaction and idle chatter are rewarded and restraint and thoughtfulness are unfashionable. Can you talk to these digital dickheads about what you mean on that, please?
Ryan Holiday
Yeah, I mean, look, social media is by definition talking and not listening. That's right. Zeno, the founder of stoicism, he said, we have two ears and one mouth for a reason. And when you're talking, what you're mostly doing is not listening. So we have this enormous sort of media culture that's about chatter and noise and it's not about thoughts and reflection. I mean, even how much of what we listen to and talk about is what's happening right now, not the historical context or the, you know, the bigger picture. And I think, not that there's anything wrong with news or podcasts or social media, but if you don't have like the historical basis, the larger context, you're not going to know what any of it means. Truman's famous line was, there's nothing new in the world but the history you don't know. And so most of what's happening now has happened before, but if it's the first time you're hearing about it or experiencing it, you're going to have the wrong read on it because you think it's, like, somehow unprecedented. But in fact, it's very precedented.
Lauren LaRose
Some of this is unprecedented, though. A lot of what we're seeing right now.
Ryan Holiday
You think so?
Lauren LaRose
At least in America. I guess. You mean. I guess if you can rely on historical context.
Ryan Holiday
That's what I mean.
Lauren LaRose
Okay, gotcha. Yeah.
Ryan Holiday
I mean, this. This archetype, you want to look at a Donald Trump. Donald Trump exists in half a dozen Shakespearean plays. He exists in Greek tragedies. There are historical precedent after historical precedent for guys like that. I mean, one of the interesting lines in Marx, Aurelius Meditations, he. He says that he thanks his philosophy teacher for teaching him not to fall for every smooth talker. So, like, the idea of the demagogue, the idea of the strongman, the idea of the con man is as old a thing as there has ever been. And part of the reason I think people have trouble spotting it or seeing it for what it is is that they don't know that this has happened again and again and again, and therefore they don't know how badly this ends. Is.
Lauren LaRose
Is he a smooth talker? I wouldn't consider him a smooth talker.
Ryan Holiday
I mean, he's not smooth in the sense that he's particularly good at it. Like he's this soaring orator, but he's really good at telling aggrieved people what they want to hear. And that's what demagogues have always done and always do. They point to the other and they say, your problems are not your fault. They're these people's fault, and I'm going to be your weapon of vengeance against them. That's as old as political strongmen have ever been.
Charlamagne Tha God
What's a second brain?
Ryan Holiday
Second brain, And I learned this from Robert Greene. The writer is like, you have to be recording and synthesizing the knowledge that you get. So it's not enough to have a mentor. It's not enough to read books. It's not enough to listen to podcasts or watch documentaries. How are you collecting and organizing this information? So, like, I'm. I'm reading the book right now, and I'm. I'm taking notes on. My pen's flying over. I'm taking notes. It's a. It's a big one. This is a Jill Lepore history of the United States all. It's a great book. And I'm going to record this, I'm going to read it, I'm going to take my time with it, and then I'm going to break this down into note cards, which I organize. And then that's what I use in my writing, in my videos, in my talks. So I think if you're not keeping a journal, if you're not recording the information that you're consuming or learning, where's it going? It's just going in a black hole somewhere. So that's what they call the second brain. What's an information diet?
Ashley Nicole Moss
Ooh.
Ryan Holiday
Well, what do you just like they say, garbage in, garbage out, right? What are you eating? What are you consuming? We understand that what we eat affects our health, affects our mood, affects our happiness, and yet people just consume straight garbage directly in their ears, directly in their eyes all day. And I think you definitely see this on the right, this just sort of depraved garbage information diet of the worst slop and nonsense. Whether it's coming from podcasts or Twitter. If you're not protecting what's going in your brain, you're gonna destroy your brain. And I think we see this happening. Like, no one should watch as much cable news or spend as much time on social media as Donald Trump does. And so you're watching it degrade. I think the most telling example of this is like, at one point in his life, Elon Musk was reading Soviet rocket manuals to figure out physics and space and the aeronautics industry. And now he just spends all his time on Twitter, you know, mainlining memes. And he's insane, right? He broke his brain. And that's, that's why your information diet matters. It's not just the quality, but it's also like, if you consume too much, your brain will break. You got to have some, some discipline and boundaries too.
Charlamagne Tha God
But if it's like, that's, if it's habitual, right?
Ryan Holiday
Like, how do you, how do you.
Charlamagne Tha God
Manage the diet after you already broke your brain?
Ryan Holiday
I remember growing up as a kid and my friend's parents watched so much Fox News, it was literally burned in the corner of the tv. And that's not healthy. Like, that's just not healthy. So you gotta, you gotta say, hey, this is when I get my news, this is when I get my information. This is who I trust to give me my information. And I think people consume way too much real time information and don't go back far enough. I think books are better. I think conversations with real human beings are better. You're just, there's this recency bias. And so much of what's happening right now is ephemeral and trivial or developing. You know what I mean? Like you shouldn't be watching the news as it's happening unless you are a hedge fund trader or you hold elected office. Wait for them to figure it out, then check in and get that information and check it against your larger historical sense of what things mean and how the world works.
DJ Envy
It just always feels like things are moving so fast sometimes. And for a person like me, when you talk about like how you download like information, if I'm watching the news when things are happening, I retain it way better than if I have to go back and like sit with it sometimes because I feel like I'm. It's a lived experience.
Ryan Holiday
You think so?
DJ Envy
That, I mean, that is just kind of what I've been experiencing in working in news. Like, I literally remember January 6th when they went into the Capitol because CNN was on and I watched it. So when I was able to talk about it, I watched it. Like, I mean, I talked about it. From me watching it in real time.
Ryan Holiday
Yeah.
DJ Envy
Versus when I go back and read things, it's. I don't know, it's just different.
Ryan Holiday
No, I get that. I think sports is a great example. It's like you could watch Stephen A. Smith all week. That's not going to change what's going to happen on Sunday. Like what's going to happen on Sunday is what's going to happen on Sunday. And so we sometimes conflate, like speculating about what's going to happen, debating about what happened, you know, get ready because.
Cam Newton
Sports, culture and entertainment is colliding like never before.
Ashley Nicole Moss
Wednesday at 10, 9 Central on BET is BET's all new series 106 in sports.
Cam Newton
Hosted by NFL star Cam Newton and sports analyst ashley Nicole Moss. 106 in sports is where the biggest plays meet the biggest conversations. Each week, Cam and Ashley are counting down the top five moments everyone's talking about. From the most jaw dropping highlights on the field to the viral clips taken over the feedback to the culture shifts shaping fashion, entertainment and black Excellence. The Top 5 countdown dives into all the game winning touchdowns, buzzer beaters, red carpet fits and headlines, making stories that define our culture. With Cam bringing an athlete's perspective and Ashley bringing an analyst edge. They're breaking down every angle. The wins, the controversies and the unforgettable moments that keep us talking. Whether it's a wild play that broke the Internet or a championship celebration for the ages or the latest trends. Shaking up Culture if it's big, it's on 106 in sports. Whether it's stars like LeBron, Steph Giannis and Durant making waves on and off the court, you know it's making the countdown. So tune in and join the conversation because it's where sports meets style, competition meets culture, and every moment matters.
Ashley Nicole Moss
Don't miss the all new series on Wednesdays at 109 Central on BET's 106 in sports.
Cam Newton
If you want to relive the countdown or catch what you missed, stream the next day on BET.
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Hell in Heaven Narrator
In the new podcast Hell in Heaven, two young Americans move to the Costa Rican jungle to start over. But one will end up dead. The other tried for more murder. Not once people went wild. Not twice, stunned, but three times. John and Anne Bender are rich and attractive and they're devoted to each other. They create a nature reserve and build a spectacular circular home high on the top of a hill. But little by little, their dream starts to crumble and our couple retreat from reality.
Ryan Holiday
They lose it.
Charlamagne Tha God
They actually lose it.
Ryan Holiday
They sort of went nuts.
Hell in Heaven Narrator
Until one night, everything spins out of control. Listen to Hell in Heaven on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
Ryan Holiday
You know, rumors are this is what's happening and that's not the actual, like, nut of it. And I think we consume all this sort of stuff and commentary around it and not like the main thing.
DJ Envy
Yeah, I could see that.
Lauren LaRose
Can wisdom protect you from being influenced? Because I do agree with you with the information diet, but they're like, I can look at a whole bunch of stuff throughout the week and not be influenced by it. I think it's the influence of it that I think is, you know, worse than just consuming it.
Ryan Holiday
Yeah. And look, I think part of this comes down to media literacy, technological literacy. I mean, like, look, something like 20% of Americans think that chocolate milk comes from brown cows. Like, no, if that's where your starting point is, you're gonna have trouble. Like when you are reading a complicated news story telling you why something happened or what it means. So yeah, you have to have a certain amount of intelligence and savvy to be able to separate. And I do think that's why it's such a battle for attention, is that some people are up for grabs and some people aren't. And I think you want to be one of the people that's not up for grabs because you sort of know what's what. To me, that's like a good working definition of wisdom. Like, I know what's what. I know what humans are. I know how humanity works. I know history. I know. I know enough about the world that I can. Look, we can all be made fools and suckers, but the bigger basis protects you against the day to day barrage. For sure.
Charlamagne Tha God
You really know people that think chocolate milk come from a black house brown cow.
Ryan Holiday
That is a statistical fact. It is nuts. That is like, is that 20%? It's like 20%. What book was that, Ryan?
Charlamagne Tha God
That's crazy.
Ryan Holiday
It is crazy. But, but, but you, you realize that not everyone's working with the same toolkit. Yeah. And. And that, that, that makes it hard to go through life.
Charlamagne Tha God
How do you attack what book you're going to write about? Like, you know, this was about Wisdom takes work. How do you know? You know, I'm going to go this way on this book and next. Next time it's about this one. So how did you pick this book and what stood out about this that made you want to write about wisdom taking words?
Ryan Holiday
It's 7% to 7%. 7%. It should be 0%.
Lauren LaRose
That is true.
Ryan Holiday
Who's drinking milk either? But look, it's. I've been doing a series. I did courage, discipline, justice and wisdom. Those are the four virtues. So I knew that was the arc. That's what stoicism is based on.
Ashley Nicole Moss
Correct.
Ryan Holiday
But I wanted to save wisdom for last because it's. It strikes me as the hardest and it strikes me as the thing in exactly what we're talking about this world, not just of lots of noise and information, but also AI, like the most essential. I think that's the interesting thing about AI is people are acting like it's going to be this magical thing that solves every problem or can teach you anything. But in fact, what you need, not just to be able to take advantage of AI because it requires you to prompt it, which means you have to be able to ask it smart questions. But, like, if you're not, if you don't have some sense of wisdom, some sense of knowledge, you're gonna be vulnerable to a thing that, by the way, hallucinates a significant percentage of the time. That's wrong all the time. So you're gonna like this idea of needing wisdom. Needing a good bullshit filter is like more important than ever because AI is gonna eat you alive if you don't have. If you don't have a sense of reality, people don't.
Lauren LaRose
I agree. Another claim you make in the book. You say cultivating wisdom requires mental struggle, and there's no shortcut for that. So what does mental struggle look like from a practical sense?
Ryan Holiday
Well, look like books are basically free. You can get them from the library. The amount of wisdom in a book is incredibly cheap, but it still takes work. You gotta wrestle with the book, you gotta read it. You gotta put the time in. You know, I think it's not just the struggle to make the time to do the work, to read, to go to class, whatever. But then it's also wrestling with big questions, like if you think life is black and white, if you think it's Easy if you think everyone is trying to tell you the truth all the time. I think again, you're gonna find yourself pretty vulnerable. So it's, it is struggle. It's a battle. It's a battle against ignorance, it's a battle against misinformation, it's a battle against your own biases. I think one of the things the Stoics remind us is that your mind is not always your friend. We all have prejudices, we all have biases, we all have mental shortcuts that we do. Ego being another one that gets in the way of us learning and seeing what we need to see. So you gotta struggle against yourself. Yourself too.
Lauren LaRose
Absolutely. And I like the subtitle too. Learn, apply, repeat. Like you're saying it has to be a cycle, not a one time event.
Ryan Holiday
Yeah, like you become a student when you're young, but that's all sort of forced upon us. But to me the essential question is, how long do you stay a student? There's a story about Marcus Aurelius. He's a philosopher king. He's the wisest man in Rome, the most powerful man in Rome, and he's seen leaving the palace and a friend stops him and he says, you know, sir, where are you going? He says, I'm off to see Sextus the philosopher, to learn that which I do not yet know. The man said, this is amazing. Here we have the philosopher king still taking up his tablets and going to school. But that's why he was a philosopher king. And I like that he was going to the teacher instead of sending the teacher to him. So there is something about staying hungry but also staying humble. Like if you're a know it all, you're right, because if you're a know it all, you know all that it is possible for you to know. But if you focus on what you don't know, if you focus on how much there is left to know, then you're always going to get better. And that, you know, think about what the Socratic method is. It's asking questions. Socrates doesn't go around Athens, you know, lecturing people, he goes around asking them questions, trying to find things out. And so this, this decision to become a student is part one, but part two is staying a student and remaining a student all of your life.
DJ Envy
Okay, I was gonna ask. With your books, it seems like your, your target or your goal is to allow people to think freely, but like have an educated like base that they're pulling from.
Ryan Holiday
Yeah.
DJ Envy
How hard is it becoming for you to go around teaching all of this in this, like, time with this administration. I saw the thing that happened with you at the Naval base, and I'm canceling your lecture. That you do?
Ryan Holiday
Yeah. I've been doing a series of lectures at the Naval Academy on the cardinal virtues for the last four years, and the last one was canceled. I was supposed to lecture about wisdom, and I was going to talk about Admiral James Stockdale, who's a famous graduate there, who famously took a course on Marxism at Stanford before he was shot down in Vietnam and sent to a Marxist prison. And the idea is, like, you want to learn from the enemy. You want to understand what they think, or else you're vulnerable to brainwashing and propaganda. Actually, Seneca, the stoke philosopher, said this. He said, we want to study like a spy in the enemy's camp. So I was supposed to give this lecture, and, like, a couple weeks before I went, they started removing books from the library at orders of the Secretary of Defense and the President because they were too woke or pro dei. And I own a bookstore. I can't get up there and give a lecture about wisdom as they're literally removing books from a library. So I was gonna mention it, and they found out, and they said, look, if you gotta remove those slides or you can't come talk here. Damn. And this is one of the elite universities in this country. These are people who someday are gonna be piloting fighter jets or aircraft carriers or nuclear submarines like these are. These cannot be sensitive little snowflakes, or we're in big trouble. These are people who are gonna not just have to make highly complex technical decisions, but profoundly ethical and moral questions. And yet here we are protecting them, not just from potentially political books, but Maya Angelou's memoirs was one of the books that they removed, probably because no one in Hegseth's office has read it, knows anything about it. Chatgpt told him it was a woke book, so he wanted to remove it. So I felt I couldn't do that. And that's, by the way, where all the virtues are interrelated, because it's not just knowing that book banning is stupid and reckless and dangerous. But then I have to decide, do I want to preserve my access or do I want to say what I think is true? And also, do you want the Secretary of Defense to be mad at you? That's where courage comes in. But then also justice, like, hey, it's the right thing, so you do the right thing. But, yeah, we are in a dangerous moment. Do you know the word Kakistocracy? So, like oligarchy, democracy, different types of governmental system. Kakistocracy is government by the stupidest. And that's what we are facing in this moment. People who are not just not smart, but actively afraid of and angry at and resentful of people who have competence and knowledge because they're fundamentally threatened by it.
Lauren LaRose
Are they? So we have to replace the term idiocracy, then?
Ryan Holiday
Yeah, I mean, idiocracy, it's a similar way to say the same thing.
Lauren LaRose
Okay, okay.
Ryan Holiday
But I mean, I don't think the American people are that stupid. I think we are in a moment where we have elected a number of officials who are actively stupid and deliberately ignorant.
Lauren LaRose
What you said is interesting because you said they're resentful of people who are smart. And to me, I'm like, I don't think they believe anybody's actually smarter than them.
Ryan Holiday
There's a hilarious list of all the people that Trump has said he is smarter than. And it's like basically everyone that's ever existed.
Lauren LaRose
That's what I'm saying.
Ryan Holiday
Yeah, but it's this idea that, like, my feelings are more true or stronger than your expertise. So it's this. It's this antipathy towards expertise, credentialism, and look like the experts are wrong all the time. I'm not saying they're flawless, but. But you don't want to be driving the smartest, most qualified, most experienced people out of the armed forces, out of the government, out of business. And that's the sort of bent that we're on. It's going to end very, very badly.
Lauren LaRose
Ooh, Listen, I want to ask you about that, this. Then. Do you think the political climate made them feel that way? Because for the last 10 years, all the political pundits and the strategists, they've just been wrong.
Ryan Holiday
They have been wrong. So it's like, you know, this idea of negative capability. Negative capability is the idea. Can you. Can you hold two opposing ideas in your head? So on the one hand, the experts are wrong a lot. On the other hand, expertise is still really important. So you can't throw the baby out with the bathwater. So you got to go, hey, why were the experts wrong about this, that or the other? What biases or tendencies do they have that you gotta protect against? And at the same time, you gotta elect qualified people? You don't go, hey, that guy talks about the military on Fox News on the weekends. Let's put him in charge of the most powerful military in the world. I mean, he's not even qualified to be the spokesperson for the Pentagon, let alone running the Pentagon. And so you gotta. You gotta go, hey, here's what I believe, here's what I think is important. And then still respect wisdom, intelligence credentials, experience.
Lauren LaRose
I wanna ask you, what role does listening more than talking play when you're in a culturally diverse setting or when you're sitting with somebody with a different ideology and you're listening to them? Yeah, but at some point, you might be like, well, that's wrong with some bullshit. You just keep listening to you and ejaculate.
Ryan Holiday
But that is. That idea of negative capability is like realizing, for instance, I have to think about this with my kids. My kids are never wrong about their feelings because they're their feelings. Now I might feel differently. It might not change. Hey, you gotta go to school. You gotta do X, Y or Z. But, like, your opinion is your opinion. And so I think what strong people are able to do, resilient people are able to do, wise people are able to do, is understand that people feel differently about different things, have different opinions about different things, and to be interested and curious about that without necessarily changing your mind all of the time. So I think diversity is strength in the sense that you want to bring as many different opinions and viewpoints and worldviews into the equation. But at the end of the day, you do have to decide what you think, what you feel, what you're gonna do. Especially in a position of leadership. Like, the leader ultimately has to listen to everyone and then make and own the decision.
Charlamagne Tha God
But it's based on what their opinions are based off of. Meaning your opinion or how you're feeling could be a certain way. Yeah, but if it's based off of some bullshit that's not true.
Lauren LaRose
Yes.
Charlamagne Tha God
Then your feeling is kind of wrong.
Ryan Holiday
Yes. And I think that's our problem with expertise is people are like, well. But I don't want that to be true. And it's like, okay, that's great. And I respect that you don't like it, but it is what it is, right?
Lauren LaRose
Wow.
Ryan Holiday
Yeah. Well.
Charlamagne Tha God
Ryan Holiday, ladies and gentlemen. New book, Wisdom Takes Work, Learn, Apply, Repeat, Apply, Repeat. It's available right now. And thank you for joining us.
Lauren LaRose
Always a pleasure. When you pull up, Ryan, you're the best.
Ryan Holiday
Thank you, guys.
Charlamagne Tha God
Next time, bring some chocolate milk from a brown cow.
Ryan Holiday
I do have a brown cow. It does not make chocolate milk.
Charlamagne Tha God
It's the Breakfast Club. Good morning. Every day I wake up.
Ryan Holiday
Wake your ass up.
Lauren LaRose
The Breakfast Club.
Ryan Holiday
So y' all done?
Johnny Knoxville
Hello, America's. Sweetheart Johnny Knoxville here. I want to tell you about my new true crime podcast, Crimeless Hillbilly Heist from Smartless Media, Campside Media and Big Money Players. It's a wild tale about a gang of high functioning nitwits who somehow pulled off America's third largest cash heist.
Ryan Holiday
Kind of like Robin Hood, except for of the part where he steals from the rich and gives to the poor.
Lauren LaRose
I'm not that generous.
Johnny Knoxville
It's a damn near inspiring true story for anyone out there who's ever shot for the moon, then just totally muffed up the landing.
Ryan Holiday
They stole $17 million and had not bought a ticket to help him escape. So we're sitting like, oh God, what do we do?
Hell in Heaven Narrator
What do we do?
Ryan Holiday
That was dumb. People, do not follow my example.
Johnny Knoxville
Listen to Crimeless Hillbilly Heist on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts.
Hell in Heaven Narrator
Two rich young Americans move to the Costa Rican jungle to start over, but one of them will end up dead and the other tried for murder three times. It starts with a dream, a nature reserve and a spectacular new home. But little by little, they lose it.
Ryan Holiday
They actually lose it.
Hell in Heaven Narrator
They sort of went nuts until one night, everything spins out of control. Listen to Helen Heaven on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts.
OK Storytime Podcast Host
I live below a cult leader and I fear I've angered her.
Ryan Holiday
Wait a minute, Sophia, how do you know she's a cult leader?
OK Storytime Podcast Host
Well, Dakota, luckily it's I'm not afraid of a scary story week on the OK Story Storytime podcast, so we'll find out soon. This person writes, my neighbor has been blasting music every day and doing dirt rituals and now my ceiling is collapsing. I try to report them, but things keep getting weirder. I think they might be part of a cult.
Ryan Holiday
Hold up a real life cult. And what is a dirt ritual?
OK Storytime Podcast Host
No clue, Dakota. Find out how it ends. Listen to the OK Storytime podcast on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts.
Ryan Holiday
The Big Take podcast from Bloomberg News keeps you on top of the biggest stories of the day. My fellow Americans, this is Liberation Day. Stories that move markets.
DJ Envy
Chair Powell opened the door to this.
Ryan Holiday
First interest rate, cut impact politics, change businesses. This is a really stunning development for the AI world and how you think about your bottom line. Listen to the big Take from Bloomberg News every weekday afternoon on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts.
DJ Envy
This is an iHeart podcast.
Podcast: The Breakfast Club (iHeartPodcasts)
Date: October 27, 2025
Host(s): DJ Envy, Jess Hilarious, Charlamagne Tha God, Lauren LaRose
Guest: Ryan Holiday
Episode Theme: The importance of wisdom, how to cultivate it, and its place as the capstone of the four cardinal virtues in Stoic philosophy—discussing Ryan Holiday’s new book, Wisdom Takes Work: Learn, Apply, Repeat.
In this episode, The Breakfast Club welcomes back bestselling author and modern Stoic Ryan Holiday to discuss his latest book, Wisdom Takes Work: Learn, Apply, Repeat. Holiday delves into the notion that wisdom is the virtue upon which all other virtues depend, arguing that genuine wisdom is earned through continual effort and reflection. The discussion explores how to cultivate wisdom in an age overrun by information, distraction, and anti-intellectual trends; it also touches on how wisdom interacts with courage, discipline, justice, and the realities and dangers of neglecting it today.
The episode offers an accessible, honest, and urgent exploration of why wisdom matters now more than ever, how it’s cultivated through a lifetime of learning and humility, and why it needs to stand as a bulwark against both daily information overload and the anti-intellectual trends shaping politics and culture. Packed with practical advice, real-world anecdotes, and humor, this is a must-listen for anyone striving to think deeply and live wisely in chaotic times.