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Hello and welcome to the Bulwark Podcast. I'm your host, Tim Miller. Our guest today, Ryan Holiday, is a friend of mine. He's awesome. And what we're going to do is try to take a step back a little bit from the news cycle, see if we can find any wisdom from the ancients on how to process everything that's happening. Also, talk with him a bit about some controversies he got in with the administration. So it's going to be a great podcast. But I had a little bit, a few politics notes that I had to get to you guys first before we took you into the weekend with a little bit of Zen. I will start with some good news. How about that? The redistricting battle is looking better for the Democrats than even it was last Friday when I was talking to Peter Hamby about this. And so I want to go through a couple of developments with you and then make a plea to some of the remaining Democrats out there who have been a little slow to the punch on this. The big news came yesterday, which is that Virginia is starting a process that could yield three new Democratic seats, assuming the party holds on to the state legislature, the state house, this coming November here. So in a week or two. So that makes those elections even more important than they already had been. Kudos to the Democrats in the state legislature. I was kind of wondering if this might be possible. I figured that Abigail Spamberger, who's running, didn't really want to make her campaign for governor about redistricting, but just because of some machinations of kind of how you got to get this process done legally and constitutionally, the legislature had to start the process without her, and they did so yesterday. So assuming that my girl Abigail Spanberger is fully on board for this, if the Democrats pass this through their legislature in Virginia this year, and then when the new legislature comes in in January, if they pass the amendment again next year, they can redistrict the state. And I looked at a map yesterday that made it look pretty clean as far as the Democrats adding three new seats in Virginia. And so that is a big counterweight to what Republicans are doing in some states. Another piece of good news this week, you got to shout out JVL's boy, Mike Pence, former Vice President Mike Pence, who would have known that he would have turned out to be the play, the chime, the bulwark that we were hoping for in the last Trump administration. Pence was working behind the scenes in Indiana with some of his old colleagues to basically try to get them to stop their redistricting effort that is not finalized. But things are looking worse for the Trump administration as far as their efforts to gerrymander Indiana. And so that could cost them a seat. The other thing that I talked about a little bit with Peter is the Voting Rights act getting overturned. Conceivably, this is going to be a big issue for 2028 and a big issue for our constitutional democracy. And it's just a big issue across the board. But it's seeming less and less likely that there will be an opportunity for any of the states here in the south to redistrict for the midterms following an overturn of the Voting Rights Act. And so that also is good news for the Democrats looking ahead to 2028. There's one other news item. Yesterday, my home state of Colorado is preparing to redistrict. Thank God. Something that I've been calling for. The Colorado process is relatively fair, but you know, it's a Democratic run state and frankly, the current map is favorable to Republicans in my opinion. You know, the way that it shook out. There are a couple different maps. Last time I was nerding out on this at the time and they ended up with a map that was, I think, the maybe the most or second most favorable out of the options to the Republicans. So Colorado can do a mid decade redistricting, but they got to put it on the ballot like California. They don't have a 2025 option to do that. So I'll have to do that next year. So that'll be a 2028 thing. So. So that doesn't really matter for this year, but is encouraging that at least, you know, there's some action out there in Colorado. Now. I asked JB Pritzker about this. I leaned in on this pretty hard. And it's up to Illinois and Maryland, Westmore and JB Pritzker, both looking at 2028 races probably they can both only squeeze out one seat apiece out of Illinois and Maryland. And Illinois in particular is already gerrymandered to hell. The subtext of Kritzker's pushback to me was that he was worried that some of the others, because it's already so gerrymandered, worried that some of the incumbent Democrats might become vulnerable. I think that's maybe a legit worry in the future. Unlikely to be 1 in 2026 and worth the risk anyway because everything's on the line in 2026 making sure that the Democrats can get some sort of foothold of power before we get to 2028 for some reasons, we'll get to here in a second. So I think that it's incumbent J.B. pritzker and Wes Moore to step up here in the next month or two and make sure that their states do what is necessary to try to get more seats. Some of the other Democratic states like New York, issued the process. These are more like Colorado. It's not going to happen for the midterm. So anyway, when you look at the total map, there was a worst case scenario that was developing where it would have been impossible for the Democrats to win in the next midterm. It was something I was talking about with Hamby. There's a depending on what happened with the Voting Rights act and some of these other states, with Virginia making their move, with California ballot initiative looking very strong in the polls, with the Voting Rights act overturned, looking like that'll be a problem for another day. Not for this midterm. All those things combined are good news for the Democrats in the effort to take back the House of Representatives and at least have some foothold of power in Washington. If and maybe it seems like when Donald Trump tries to stay in power or tries to do some other efforts to undermine our elections come 2028. And that takes us to the other topic I wanted to bring up, which is Steve Bannon was out yesterday in an interview I believe with a guardian. And let's listen to what he had to say. Well, he's going to get a third term, so Trump 28. Trump is going to be President 28. And people just ought to get accommodated with that. So what about the 22nd Amendment? There's many different alternatives. At the appropriate time, we'll lay out what the plan is. But there's a plan and President Trump.
B
Will be the president in 28.
A
There's a plan. Trump will be president in 2028. I want to start here. This is the only way for Steve Bannon to get attention right now. Okay? He's out of the loop in this White House. It's not like the first term. And I am seeing on social media a lot of Democrats like clapping like seals and doing exactly what Steve Bannon wants them to do, which is talk about Steve Bannon and his Svengali like effort to keep Trump in power when he's an 83 year old geriatric. I think that we should look at this logically and look at it strategically because that's what Steve Bannon's doing. Steve Bannon isn't like letting you guys in on A little secret that they have a secret plan to keep Trump in power. Steve Bannon's running. An angle like this is an angle. This is a bit. He wants attention for himself. He wants to throw this out there in the hopes that things develop that way. And I don't think that we should play into his hands. I think that we should counter it. As I mentioned, Trump will be 83 in 2029. Who knows what will be happening? And that guy's adult brain in the fall of 2028, when he's 82 years old, would he be capable of running another race? Would he be capable of overturning? Would he maybe just be happy that he got the ballroom named after him and they're going to mint a coin with his face on it? It's hard to predict. And that's why the right way to look at this is probabilistically through probabilities. You have a lot of pundits. You're incentivized in the pundit sphere to come on in a moment like this and be like, see, he's gonna do it. Trump is trying to stay in 2028. Or to go out there and be like, trump's never gonna be able to stay. There's no chance he's gonna stay. That is how you make a point on one of those panels with Scott Jennings on cnn. Right? The truth here is that it's a possibility. The right way to think about this is that can we completely wave this off? Of course not. Is he absolutely going to do it? Doesn't seem like it to me. Who knows? A lot can happen. The future is unknowable. And so you think about this as well. Does it seem like they're going to try? Is it a possibility? Yeah, it is. It is a possibility. And we should take that possibility seriously and do things that are useful to counteract it. For starters, what I was just talking about, the most useful thing that Democrats and anyone in the pro democracy movement can do to help prevent Donald Trump from trying to stay in power a third term is to make sure the Democrats are in the House in 2026. So the Democrats have powers, Democrats have subpoena power so that they can't just work the game post election, which is like, what they would really want to do, right? Maybe not rig the election, but work in the aftermath, as far as, you know, how the electors are certified, et cetera. If the Democrats, if the speaker of the House is a Democrat, that makes their job a lot harder. So that's the first step Here is winning the House of Representatives in 2026. If you're the Democrats, other things that Democrats can do about this that would be useful or members of pro democracy movement, media folks like us. Something that I've been talking to Joe Perdicone about. Make Republicans respond to this. Make Republicans in swing areas respond to this. It's not popular. Believe it or not, Trump might be more popular than we all think. It's not popular for him to become a king. Still not popular. There's certain places, you know, I'm sure the senator in the Senate race for Alabama to replace Tommy Tuberville, you know that will be a litmus test whether or not you're on board with Trump 2028. It'll be a winner for you if you say that. And a lot of these other districts, it is not. These guys should be pressured and should not be allowed to just be like, oh, this is just a joke. This is just a gag. It's not a joke. It's not a gag. They got it on hats. His chief strategist for 2016 is saying it's going to happen. They should have to answer it. If they cannot say definitively that they would not be on board with it, that's something. That's a political vulnerability for some of them. I also think we should make fun of it. Like, really? This is the best you guys can do? Somebody that was born in 1946 is going to try to become a king in 2029. With lathered on burnt sienna makeup. He already has like these massive hand bruises. He's walking with a limp. He has hair. Look at what is happening with the weave right now. And he looks and sounds ridiculous. He should be spending his golden years after his second term with his grandchildren. If he is trying to stay in power to become an actual dictator, it is because they're so weak. It is because they know that J.D. vance has negative charisma. It's because they know that they have no succession plan. It's because the only option they have, the only thing holding their political coalition together with bubblegum and twine is like a decrepit old reality show host. Okay, if you really want to try to roll that up, let's see it. Let's see it. Let's see him. Roll him out there at 83 in his wheelchair and see how he matches up against whatever the Democrats can put forth. Maybe Obama, who knows? Maybe bring Obama back. He's youthful. Maybe the Democrats come with somebody else. I don't know. I think that mocking them is also useful in this moment. I just think the thing that is not that useful is making him seem like he's so strong. Like, ooh, I'm really scared. I'm quaking in my boots about Donald Fauch, about this old theater queen trying to become a dictator at age 83 in 2029. I'm not. I'm not shaking my boots. It's a worry. It's a concern. We should be concerned about it. We should be fighting back against it. Should be making sure that the Democrats are in the best position possible in the midterms. I'm not trying to downplay the fact that the end of the democracy and the longest running democracy in the world would be a bad thing. It would be. But in this moment, I think the fact that they are floating it is a sign of weakness and we should treat it as such rather than letting them use it to kind of puff up and feel more powerful, because that's not what's happening. And also our friends in legal community, our friends, Society for the Rule of Law, Mark Elias, all those guys should be doing the real work to get prepared for what might be a real fight in 2028 with Grandpa Trump. So there you go. That's what I got for the intro. My friend Ryan Holiday. It is going to be a good one. He's extremely wise. Stick around for it. I am so delighted to welcome writer and philosopher. His latest book out this week is Wisdom Takes Work, the final installment in his Stoic Virtues series. He offers advice and insights@thedailystoic.com and on the Daily Stoic podcast, it's Ryan Holiday. What's up, man?
B
Hey, thanks for having me.
A
Good to have you. I've never been on the Bulwark flagship. We did a spin off on your. What's it called? The Daily Dad.
B
Oh, yes. Yes, we did.
A
We did a Father's Day thing on the Daily Dad. People should go back and find out. That was so good. So we're not gonna do any dad talk on this one. Folks can go into the archives. All right, I wanna start here. People tell me often when I'm out and about that this show is keeping them sane, which I don't really understand because it's maybe driving me insane. So maybe they're, like, taking it from my brain somehow, cosmically, I'm not sure. But you, on the other hand, I can understand why people would say that you're keeping them sane. You're doing some real work here. And I want to start by playing you one of the things I have to listen to every day and see if you can give us some advice on Stoic wisdom. In response to this, here's yesterday law enforcement roundtable at the White House.
B
Let me just say, Mr. President, that.
A
This country was going to die without you.
B
This country was going to actually die without you.
A
That's what we were facing in 2024.
B
We've been invaded for four years. Our communities were sinking.
A
Our public safety had gone to zero.
B
Cartels are running entire communities.
A
Hmm, there you go. The country is going to die in the face of that. How do you process it?
B
Can you imagine how much money you would have to be paid to have to say that to someone?
A
Like, there's no number for me.
B
I'll talk about the Stoic element of it. But I think I am struck by the timelessness of that position. Right. The sort of courtier in the king's court having to tell them that they're amazing, that they saved the world. Like, I imagine Seneca, the Stoic philosopher, is Nero's tutor. And probably a very similar sort of rationalization. You know, the first five years of Nero's reign are actually quite good. They're called the Quinquinium Neronis, the five golden years, where Nero basically listens. Then he starts to become insane and deranged and horrendous. But the signs were obviously always there. And you've got to imagine Seneca in saying things like that to Nero all the time. Because that's how he gets Nero to listen to him. Right. And so he probably tells himself that he's, you know, preventing him from being as bad as. As he could be.
A
So Stephen Miller is kind of like the Bizarro Seneca in the sense where he's doing this in service of his nefarious plans rather than. Rather than lavishing with praise in service of his, you know, efforts to make things better.
B
I don't want to go that far. Cause Seneca is actually very smart and probably fundamentally not an insane person.
A
So I. Bizarro. Bizarro Inverse.
B
Yes, sure.
A
Did you not see the Bizarro Seinfeld episode? It's like bad Seinfeld.
B
I did, of course. Yes, I get what you're saying. I just mean for all time in the royal courts.
A
Sure.
B
The person whose position is dependent on the Them always remaining in favor. Like, we have a few other anecdotes from this court. Like, the other one is Epictetus, who's actually a slave working for one of the advisors to Nero, tells us this scene about catching this wealthy Roman Blowing smoke up the ass of Nero's cobbler. Like the guy that makes Nero shoes because he wants to remain in Nero's good graces. So this is a little bit closer to that. You know, when you have an unstable, vain, and vindictive boss, what are the things that you have to say to that person to get them to do what you want to do or to let them let you keep doing what you want to do? So I just think the timelessness of that is endlessly fascinating and the lengths that humans will go to degrade themselves to maintain their access and influence.
A
I do think there was a moment maybe in this country where we felt like we had evolved past that at some level. Not evolved past apple polishing, obviously there was that, but evolved past, like this level of subservience in a royal court, and apparently not. I saw you at the. You posted. I didn't see you in person. A picture of yourself with the family at the no Kings protest.
B
Yeah.
A
So just kind of wondering. Your show is non political, right? In a sense. I mean, it's political, but it's not modern politics. And you're talking about the stoic virtues, wisdom, courage, justice and temperance. And so just kind of wondering how you're sort of processing, navigating that, given the threats.
B
Yeah. I was both pleased and horrified that my son, in the backseat of the car, I was like, hey, do you want to go to this thing? They said, yes. We went to the one back in June. He's like, can I make my own sign? And I said, yeah, of course. And he goes, how do I spell immigrants? So we're spelling him and he writes, immigrants. We get the job done from Hamilton, which is his favorite thing. We've listened to it an endless amount of times. We're not Immigran. So I. Although my. I guess my grandmother is, but I thought that was funny. Then he shows me the sign when we get out of the car and he wrote fuck ice on the bottom of it, which is a lot to see from your.
A
Your 8 year old. I don't know if that counts for temperance.
B
No, no. And. And then obviously people were quite upset, as if I had told him to do it. I think he'd just seen it on somebody else's sign. I don't know. Look, to me, what stoic philosophy is, is not just that this sort of moral philosophy, an ethical framework and philosophy for rationality. I just think like, life's too short to be a bootlicker, you know, and there was this, this whole group of Stoics, known as the sort of Stoic opposition who just didn't want to deal with Nero, they didn't want to deal with dominion. At one point, the Stoic philosophers were such perpetual thorns in the side of the sort of powers that be that. That all philosophers are banned from Rome. So Epict spends the rest of his life in exile. There's this Stoic named Agrippinas who's fascinating, who's told, why don't you blend in a little bit more? Isn't this dangerous? And he goes, everyone else can be the white threads. I prefer to be the red thread in the garment that makes it beautiful. His point is you should be yourself. You shouldn't mute your colors. I think about it just on that level of just. I say what I think. I think my job is to say what I think is true. And I think when you're looking at what is effectively a fascist administration, or a at least aspirationally fascist administration, it behooves you from all of the virtues we're talking about to say that, like, you have to have the wisdom to see what's obviously in front of you. You have to have the sense of.
A
Of.
B
Of ethics and, and right and wrong to know what. What's obviously right and wrong. And then you have to have the courage to say it. Even though it's not always good for business.
A
Do you need to have the wisdom to not let it consume you?
B
I do, I do. I think when I think about the ancient world, I'm always bemused at our tendency to idealize it. We think of Socrates as this guy walking around in a toga in this beautiful, idyllic, peaceful society. The Athens that, that Socrates lives in is not just the Athens of the Peloponnesian War, which he fights in the sort of great power conflict of his time, but it is also the Athens afterwards of the 30 tyrants. Like, one tyrant is bad, 30 is really, really bad. And then, then when they go out of power and it becomes a democracy again, like the mob puts him to death. So, like, it's always been pretty bad. And I think the role of philosophy is to help you maintain your equilibrium, your sense of values, your sense of truth and perspective in the midst of disorientation and disillusionment and all of the things that they faced then and we face now.
A
I might have a couple more particular examples of that I would like to get your wisdom on. But first I want to get into your Navy lecture from earlier this year, because I think this is an Important story I mentioned on the show back in April, but I kind of want to get it from the horse's mouth. The gist of this was you deliver lectures to the students at the Naval Academy every year on stoicism, or have the last couple of years at least. And you'd sent them a PowerPoint, I guess, about what you're going to be talking about, and included a reference to what at the time was a recent removal of 380 books from the Nimitz Library on campus. When you refused to remove that from your talk, they canceled it because it may have flouted Executive Order 14151, Ending Radical and Wasteful Government DEI Programs. Talk to us about that.
B
So, yeah, I'd been giving a series on the cardinal virtues for the last three, and this was supposed to be the fourth spring and summer. The biggest lecture is at what's called Plebe Summer, which is where the thousand person class at the Naval Academy, all the incoming first years are given a lecture. And so I did courage, I did discipline, I did justice last year where I spoke about Jimmy Carter as my main example, who is a graduate of the Naval Academy, I think embodies this virtue. So this year I was supposed to give it on wisdom. And the main through line was going to be Admiral James Stockdale, also graduate of the Naval Academy, same class. And so I put together the.
A
Was James Stockdale woke? I don't remember. He's a white guy. I don't remember he had that bad debate. I don't remember whether he was woke.
B
Well, extremely woke. As I was gonna explain. The Navy sends him to STANFORD after about 20 years into his career and he gets a graduate degree, studies philosophy. But the most influential class he takes is a class on comparative Marxist thought where he reads only the Marxists in the original. Right. And so when he is shot down over North Vietnam and sent to a Marxist re education camp, this experience actually studying the ideas of his opponents or these transgressive, you know, this is the height of the Cold War that he does this. He's at Stanford, I think, in 61, you know, it's actually extremely important. And he would talk about how you need to be familiar with ideas that you disagree with or even dislike. So that was. That was what I was originally planning to talk about. And then a few days before I was supposed to go, that's when the news of this sort of removal of books from the library were going to come. So my mentioning in the talk is I have a bookstore which you've been to. Sitting across from it right now in the window of that bookstore is a giant sign that has that lyrics from the Rage against the Machine song. It says, they don't have to burn the books, they just remove them. And I was going to talk about how, you know, we should be able to engage with ideas that we disagree with, we don't like, that are not even good. So that was my point. So I sent the slides in the day before, not for approval, but so they could be loaded into the presentation. Like, like my contract did not allow them to pre approve my remarks. And so then when they called me and they said, hey, we can't have you talking about politics in your, in your address today. And I said, that's strange, Considering less than 12 months ago, I gave an entire talk about the legacy of President Jimmy Carter. And they said, well, okay, actually what it is, is we, we just don't want you to say anything that's going to embarrass or imply that we disagree with the administration's policy of removing the books. And they said, so if you just remove these two slides, the talk can proceed, but if you don't, obviously you can't. And I said, well, I'm supposed to talk to the football team later where I'm definitely not talking about politics. Is that also off the table? And they said, yeah, you got to remove these things. You can't come on campus. So to me, that was a pretty straightforward decision. Not just because of my sort of personal values, but I thought, I can't come up to these kids and talk about courage and talk about discipline and talk about justice and then not address the fact that they're removing Maya Angelou's book from the library because it's too woke up. And then even worse, remove said mention under pressure, you know, under political pressure, like, I'm a private citizen. That's. That was a bridge too far for me. And so the talk was removed and they put out sort of a nonsense statement about how, you know, due to a scheduling change, we decided to cancel the talk.
A
So it's interesting who they're more scared of, actually. Like, it shows you this change of the power dynamic and when it comes to the speech, right like that, the Naval Academy, in a different time, I think by a different time, I mean last year would have been more worried about being embarrassed by somebody coming out and saying, hey, the Naval Academy is trying to censor me. This is crazy. In a free country, they would have been worried about that. But in this case, they were willing to take that PR head because they're scared of Trump cracking down on them if they allowed wrong talk.
B
That's actually, I think, the crux of it. They said, hey, we just don't want any controversy. And I said, I get that. Like, I have a lot of empathy for the person who has to deliver this news. Right. Because this is a person who's served our country honorably and is. Is concerned about their pension. Right. Like, why should this person have to blow up their career over two slides in my talk? I get that. But I said, hey, you know, you're canceling a publicly announced talk hours before it's supposed to start. Like, you're not avoiding controversy. This will be much more controversial than if you just allow me to talk privately to a thousand people. And then I realized exactly what you just said, which is actually the worry is not controversy or heat. It is very real reprisals from people in power or worse, what happens if the spotlight is pointed on those people and then the goons that want to impress that person are now. So it's not like the carrot and the stick. It's two sticks. It's the stick of I can take your job away from you. And then also, do you want to be thrust into the spotlight and maybe a crazy person comes to your house?
A
Did you hear from any, you know, of the big free speech types on the right after this happened? Anybody. Anybody come to you and say, hmm, I'm a little concerned about this. The government is canceling a speech on stoic philosophy.
B
Yeah. You can imagine all the cancel culture people that have been really loud the last couple years, they really took this personally. And it's what finally got them to break with the administration because they've been morally consistent on this all along. Right. No, I think fire.
A
You're not on the Ben Shapiro show next day as a hero of the free speech movement.
B
I was not. And, you know, I think fire.
A
Yeah, FIRE is great. Fire is like the legit free speech organization that is out there, no matter protecting speech. And obviously, in your case, you weren't doing bad speech. But they'll even go out there and protect bad speech. And no matter which side it's coming.
B
From, they put in a freedom of information request, which I'm interested to see when it eventually comes out. Because, like, it was intimated to me that this went up pretty far. Right. Like, people of very high rank ultimately made the decision. It wasn't like a. Sometimes. Sometimes bureaucracies do things at a low level.
A
Sure.
B
Hoping to protect the interests of the people at the high level. I got the sense that this was. This was vetted pretty high up. And then, you know, the interesting thing, and I think this is the message that people who end up being sort of collaborators or accommodators find. And this is something that Stockdale talked about. He said in the prison, he said, you're under the pressure of extortionists, and when you compromise with an extortionist, you just get more pressure and extortion. And so the three star admiral who should have pushed back on this order at the beginning and then obviously shouldn't have accommodated and then found herself in the position of having to cover up, you know, even criticism of that order. I mean, Hegseth fired her a few weeks later anyway. Probably because she's a female admiral.
A
Right.
B
Not because she wasn't going along with what they wanted. She clearly was.
A
That's worth saying. Yeah. Just to say it's like the admiral that was in charge of the. Was she the Secretary of the Navy at the time?
B
No, she's the superintendent of the Naval Academy.
A
Okay. So the woman that was the superintendent of the Naval Academy either made the decision or had folks around her to protect her make the decision to cancel your speech in the hopes that that would protect her career. And then a month later, she gets fired. In part for a lot of the same reasons why they wanted to cancel your speech like this. Overly concern about DEI and diversity, things of that nature.
B
Yes, you're making a deal with people who fundamentally don't think you should exist in the first place. So they're not trying to come to some balancing point with you. There's nothing one or two things they want. They want everything and all of it. And that's why the accommodation strategy is never going to work.
A
This episode is sponsored by BetterHelp. I was trying to do my best for you with Ryan Holiday on the pod to give you some amateur therapy today, but, you know, we should really appreciate the professionals. We're just past World Mental Health Day, and we're out here trying to say thank you to therapists and encourage all of you that might need a little extra professional Help to use BetterHelp and be one of the 5 million people who have found a therapist on BetterHelp to improve their mental health journey. BetterHelp has a list of quality therapists that work according to a strict code of conduct at all fully licensed in the US BetterHelp does the initial matching work for you so you can focus on your therapy goals. A Short questionnaire helps identify your needs and preferences and our 10 plus years of experience and industry leading match fulfillment rate means the the BetterHelp will get it right the first time. If you aren't happy with your match though, you can switch to a different therapist at any time from their tailored Rex. It's super easy. You guys know if you've been listening to the show that I'm a huge proponent of therapy. I had a moment in my life about a decade ago now where I was just, it was hard to get out of the covers and I found a therapist, Dr. Sharp, who I just will always appreciate helping me turn the corner on it and start thinking about things differently. And you might not even know it now, but you get some of my little therapy thoughts sprinkled it on the show because he dumped a couple little pieces of therapy nuggets, some therapy language into the back of my brain that pops out from time to time. So this World Mental Health Day, we're celebrating the therapists who've helped millions of people take a step forward. If you're ready to find the right therapist for you, BetterHelp can get you started on that journey. Our listeners get 10% off their first month at betterhelp.com thebullwork that's better. H-E-L-P.com thebullwerk let's go to the book Wisdom Takes Work. You sent me a couple of the sections that I've read. I liked this paragraph. Each of us must be at war with the fool within and outside of us. And I think that you are writing that in context. It's something that I have to think about myself a lot. One prominent example of this you teased out was Elon Musk. So talk about maybe the big picture argument you're making here. And then we can get into Elon Musk.
B
We're all fallible. We all have biases, we're all susceptible to things. I think you and I share at least some empathy for people who are clearly wrong about stuff that's happening in the world right now. Because I've been clearly wrong about things. And I didn't. I know that. I didn't think I was being stupid at the time. Right. You just realize, like, how vulnerable we all are to seductive arguments, to hearing what we want to hear, to being blinded by anger and grievance or tribalism. So wisdom isn't just this kind of acquisition of knowledge and facts. It's not study and teachers and education. I mean, obviously that's part of it, but A big part of it is like just keeping that stupid part of yourself in check, right? Like the self awareness to actually put your beliefs up for review, to challenge yourself, to make sure that you're not falling prey to emotional arguments or cognitive dissonance. Like, it's not just the acquisition of knowledge, but it's also the removal of foolishness, that. That is the sort of perpetual battle, especially in this, like, modern world, where there's so many powerful forces and information in play. Like, I think just maintaining your sanity is a constant battle.
A
And it's a battle that I guess one of the two richest men in the world, Elon Musk, has lost. It seems like maintaining his sanity. It's good when you go through the chapter because it's important, I think, for readers of both stripes, big super fans of Elon Musk and people that have come to really loathe Elon Musk and have the sticker on their Tesla that says, I bought this before he went crazy. It's important to just accept the truth about him, which is that there are certainly some rich people that got lucky, you know, that had a, whatever, silver spoon in their mouth. Nepo babies, you know, right place, right time. Certainly there are plenty of those types of rich people out in the world. I've met many of them. I'm sure you have as well. That's not Elon, right? Like, Elon was obviously extremely smart, took big risks, succeeded where many other people had failed, and yet even somebody like that then falls prey to this vulnerability, this human frailty.
B
Well, and I would say is smart, like, clearly still operating most of the companies at a fairly high level too. Like, have you seen the Glass Onion? Like the Edward Norton character. That's more or less. Edward Norton plays like an Elon Musk character. And he's sort of revealed at the end to have been like a total fraud, that he was like actually a fool. He knew nothing. And that's much too simple. And it lets all of us off the hook. Like the cautionary tale for Elon Musk is how does one of the smartest people on the planet, the person with the access to the best intelligence, the greatest minds, has the highest stakes. How does social media break their brain? And then you're like, well, it won't happen to me, as I tweet 50 times a day. You know, in the same way that you might look at someone who sort of collapses into a drug addiction or something, there but for the grace of God, go, I, like, these are powerful things. And. And in some Ways, the smarter you are and the more successful you are, the more vulnerable you are. Like a friend of mine who works in vc, he was saying that making a contrarian bet that turns out to be right can be a brain destroying experience.
A
That's interesting.
B
I think that's partly what happens to Elon Musk. I think that's partly what happened to Peter Thiel. This happens to a lot of people. I remember because I was writing a book about Peter Thiel. I was sitting with him the day after he made that first Trump donation.
A
Really?
B
And like, where were you? In his office in Palo Alto. And his justification was not particularly well thought out. I think he was just like, Trump is very undervalued by the market. And if it turns out to be right, that's a good bet. Yeah, but if you look at from there to here, Right. That's the brain destroying experience. Like when you, you make a bet and everyone else thinks it's done. This happens to entrepreneurs, artists, all the time. You, you do something and everyone tells you it's a terrible idea, and then it turns out it was a good idea.
A
Yeah.
B
How do you then calibrate the value of your subsequent ideas? You now have a very real reason to doubt anyone's criticisms, warnings, advice, and sometimes they're just, you really are about to drive your car off a cliff.
A
And this is Trump himself. And obviously it's people to bet on him, but it's Trump himself. He didn't think he was going to win in 2016. And so now how could somebod, how could he have any advice? That's why he bristled at having the close advisors the first term that told him he was wrong all the time, because he was like, what do you guys know? You're all the same people that told me that I should drop out after the Access Hollywood tape or told me that I had no chance. And so now you're at a place this time where he doesn't even forget receiving dissenting views and rejecting them. Now he's not even receiving them.
B
And just because your contrarian bet turned out to be right, it doesn't actually mean that it was a good bet. Right. Like, if I spin the chamber on a, on a revolver and then I pull the trigger and I don't die, that doesn't mean that I knew better. Right. It just means I put my life in my hands. Like, by every metric, he should have resigned after the Access Hollywood tape because he debased and humiliated himself and rendered himself unfit to be the president. Of the United States. Now, whether it was disqualifying to win an election with, you know, by a razor thin margin is actually a different discussion about whether you should have done that or not. This is where ego is so critical. Like, ego can very often learn the very wrong lesson from events that have happened because it filters it through what it wants to be true. When Elon Musk takes all of his money from PayPal and he dumps it into this rocket company, all his friends stage like, literally an AA stage style intervention, like, you cannot do this. You will lose all of your money. Yeah, so they were wrong in that case. Now, was it a very risky, perhaps even reckless bet? Yes. Right. So, so does he learn from that? Hey, when all your friends are united against you doing something, don't listen to them. Or is it something maybe a little bit more nuanced? And so then when he decides to buy Twitter or he decides to take a chainsaw to the federal government, and some people he knows are like, don't do that. Why would he listen to them? And that's where your brain gets broken.
A
I'd forgotten you'd written that Peter Thiel Gawker book. And so I do, I feel compelled now, just for the sake of podcast, to pick your brain on it. And obviously Peter's now out there doing the Antichrist lectures. South park did a big take out on him. And everybody makes the obvious joke about how somebody who is transforming physically into kind of a demon looking creature who is obsessed with the Antichrist. Maybe you should be looking internally. I'm just wondering, is it just succeeding on the contrarian bet? Was there anything else you thought about it? And obviously a brilliant person, I mean, even more objectively than Elon, probably, because the number of bets he's made in so many different areas that were proven right. And a lot of smart people that hate him talk about his book and how insightful it is. But what about Mao? Like to have all of that insight and power and use it how he has is pretty dispiriting.
B
Here's my pet theory for what I think is happening to a lot of these folks, and maybe we'll pull back the curtain a little bit. The wealthy and powerful love dinner parties, right? They love dinner parties. And then they love inviting. This goes back to the idea of what's timeless about, like, a king's court. They love inviting, sort of like intellectual, artistic, successful, creative. They love having an audience of fancy people. Right? And I'm sure you've been invited to many of these usually less and less. But yes, same. But I was usually kind of like the diversity invite, right? Like, I'm not like the others. Maybe they know my beliefs aren't exactly like theirs. But, like, I was there to keep things interesting. I get invited to a lot of these. I think you do, too.
A
Yeah, sure. Well, we want you to come here and talk about Epictetus. You know, keep some. We don't need your take on, you know, what's happened in the midterms kind of thing.
B
Yes, yes. But they'd be like, hey, I'm having a dinner party and I invited this author and this inventor and this people, and you're there, and they're always fascinating. But really it's a way for the powerful person to kind of hold court and they trot out their theories and their riffs and their little explanations for what's happening in the world. Right. And I think in this sort of Silicon Valley world, there's a lot of these dinners. And as the people have become more and more powerful, the people who attend these dinners are more and more dependent on them. And so what happens is, I think you can explain some of these things that Peter has said that have gotten him in trouble, or Elon Musk has said they've gotten him in trouble as, like, things that went over well at a dinner party, because no one would say, that makes no fucking sense, or, what are you fucking talking about? Or don't ever tell anyone that ever again, because you sound like a super villain.
A
Yeah.
B
And so they're sort of trotting these things out and refining them in these discussions and in these group chats. And then they say it in a public medium, like on a podcast or in an op ed. Like, Peter Thiel famously wrote this op ed many years ago. The famous line is, he believed that democracy was it democracy and multiculturalism. Yeah. Are no longer compatible. He. He basically, he wrote like a piece that in some ways argued against women's suffrage. Now, this isn't totally a fair interpretation, but it. That struck me as an early example of like a very tone deaf take that. Libertarians he was having dinner with never really challenged him on.
A
Yeah, you were right, it was capitalism, but it was within the same book about how multiculturalism and diversity is bad.
B
But, yeah, my point is, I think they get used to trotting things out in these dinners. And then the Stephen Millers go, you know, if it wasn't for you, the country would have fallen apart. Or, you know, we need brave troops. So I think there's this weird echo Chamber that's happening in private. And then when it emerges in public, it suddenly is subjected to, ironically, like, market forces, like the marketplace of ideas, where it is swiftly dismantled and destroyed. It's the sort of Emperor's New Clothes, but in the Silicon Valley entertainment model.
A
Is it possible that Peter Thiel is actually a supervillain, though, and that it's just. It's just leaking out?
B
I certainly think he likes being perceived as a supervillain. It's good for the brand. It's mildly bemusing to him. And it's always better to be radically overestimated in that sense.
A
Similar to what I was saying to Bannon in the intro to this pod, where I was talking about how the 2028 thing, that he's floating Trump, 2028, which is a real risk, which we should take seriously. But when Bannon says it, that's about Bannon. Bannon wants attention for himself as a bad guy, as a Svengali. He doesn't actually have a plan yet. He's, like, hoping a plan emerges and that he seems like the powerful Svengali. Anyway, my reflection on your wisdom so far is the things that have saved me from my worst impulses so far in middle age is that I hate those dinner parties. Hate them, and all of my contrarian bets have failed so far. So those have been the two gifts that I've been given unexpectedly. Another section from your book, we talk about the information diet and how that part of being at war with the fool within and without us is to manage that and use Trump as a example. I want to talk about Trump first, and then I want to talk about all of us. So talk about the example used for Trump and the information diet.
B
Have you ever heard those reports of Kennedy's. All the drugs Kennedy was on when he was on, and then one of his doctors finds out and he goes, no one with their finger on the button should be taking anything like that. Yeah, I think when you. When you actually lay out Trump's media diet, you're like, this person shouldn't even be coaching, like, a children's baseball team like this. This is terrifying, right? Like, nobody should be watching Fox and Friends, but, like, the president shouldn't be watching Fox and Friends. And like, I remember I was reading this Rolling Stone. It kind of brought a home for me. So I was reading this Rolling Stone profile of Kid Rock, which is fascinating article. And in it, Kid Rock's about to go on on Fox News. And he's like, I'm going to. This is before the reelection. But he's like, I'm going to call Trump and tell him that I'm going to do this. And he calls and Trump picks up. You know, he's like, hey, I'm about to go on to. And then Trump, like, turns it on and watches it, right? And you go, okay, this is. This is not healthy, right? Like. Like a billionaire should not be this reachable. Should not be this reachable by Kid Rock. Should not be tuning into television shows because his friends are appearing on them and saying nice things about. Like, this is. This is a recipe for melting your brain. And there's actually a really good quote from Bannon early on in the first term where he was described. He was like, the president watches five hours of TV a day. He's like, what would your brain look like if you did that? And I think that kind of gets to the essence of it.
A
Yeah. And it's also like, he also says, like, he wakes up, he has three TVs, all showing different news channels. He's watching five hours of uninterrupted TV during the executive time. And then during the rest of the time, the TV's on in the background, like always doing, you know, Fox cable news brains.
B
It's not good for your psyche because this is a. An artificial, radically cranked up version of reality. To be a leader requires a certain amount of reflection and sobriety and perspective. Like. Like, look, even George Bush. George W. Bush was reading multiple books a month as President of the United States. Like, he's nobody's idea of their. Of a great president, not anymore, but like he was, at least. I mean, George W. Bush reads the Great Influenza by John M. Barry and puts in place the pandemic preparedness response group that Trump disbands in December of 2019. He was reading about things, understanding history and trying to bring it into his administration. That's the opposite of what we're doing here.
A
All right? We're going to do the harder part for the listeners. Now, that's reflecting on oneself because it's easy to see the ways that Donald Trump and Elon Musk have been unwise in the past few years. But later in the paragraph I read from earlier, you write, none of us can rest content that just because we're smart or educated, we're not also capable of being an idiot. In both of the categories, the Elon and the Trump category, one is kind of overconfidence about being right about things can lead to mistakes. I see this in the Democratic Party and the resistance and all of us individually and people I talk to and myself, like, overconfidence that we were so right that Trump is horrible and bad led to blinders and just like going back to like my just speaking for myself, like my original. And it ended up working out by accident, like my original sin. Like part of the reason. Like when I became the spokesman of the group against Trump. And to me it felt righteous, but I also thought he had no chance to win. And so both Jeb and my father called me and were like, aren't you a little worried that he's gonna become the president? And like, you will have been on tv. And he seems vindictive. And I was like, this fucking clown can't win.
B
Right.
A
You know, so. Oops. But I feel like that same underestimating of him has plagued us for years now.
B
Yes.
A
Decade almost. And many other things. Just like the sense that you're right always about everything and that the other side is idiots can lead to misjudgment about the fact that you're not always going to bat a thousand.
B
Yeah. Someone can both be wildly unqualified to be a good president and then be very savvy at media and politics and power. I think what the left has done a bad job of understanding is how is he continually successful. And I think, like, in some respects, we overestimate and over index his media savvy. I'm more interested in how does someone who is all the things that he is manage to. When he's in the room with people who previously had pretty strong thoughts on him and his character, how does he manage to bring them around? I think his underrated skill, and I saw this because I, like you, had a previous life. I was the director of marketing and American Apparel with Dove Charney, who is a similar figure to a Trump or an Elon Musk, Like a genius in some respects and a wild maniac in others. And I watched him as he drove the company into the ground, somehow still managed to get hundreds of millions of dollars from like, the savviest investors in the world. And I realized that in some ways that that wasn't as complicated as you thought, because he would take this reputation that he had and then in the room be the opposite of that reputation and manage to convince smart people that they saw something that other people were missing. Right. Like, what is it that allows him to convince people who previously thought he was crazy? How does Bill Maher go in there and actually get a little bit seduced? I think that's an illustrative and we should be thinking about that as far as not just this particular administration, but it gives you an understanding of the historical past as well. Because you realize, like, Stalin does this to fdr. FDR goes at the end of the war, and he's like, I can work with. Towards the end of the war, I can work with Stalin.
A
Right?
B
Like, I can make this work. And then Stalin basically eats him up. Khrushchev does the same thing to Kennedy. These sort of authoritarian figures, part of what they do is their reputation actually leads you to underestimate them. And then they're actually quite charismatic and seductive and disciplined in the room, and that's a big part of their success.
A
Now, speaking more to the personal about how listeners and how we all kind of process all this, I've been noticing out there from some folks that I hear from, and I say this with nothing, with love, but people in our kind of that are anti Trump, whatever you want to call that, their information diet in Trump 2.0 isn't a ton better than Trump's watching MSNBC or various YouTube channels or, you know, whatever is not. Yeah, it's not the same as Fox in the sense that it's, like, not as nefarious, you know, in some ways, like, intentionally still. I was with somebody yesterday, and, you know, they come up to me and I'm getting just a lot of wrong information that I know is coming from resistance left sources. And they're asking me about it, and it's tough. It puts me in a tough position. Right. Like, you know. No, like that. You know, like, whatever. Like, whatever. This conspiracy that's going to bring down Trump is not happening. Right. And I think that I get where it comes from. It comes from a place of, like, people are mad, people are upset. People want to speak out about this. They want to be educated, and then they find themselves, like, consumed in a soup of information that is not actually serving them. I wonder what you. What thoughts you have for somebody that might be in that boat.
B
Yeah, look, I love podcasts. I have a podcast. I'm happy to be on this one. I think everyone should be listening to fewer podcasts right now. Podcasts are not.
A
Okay, we got to bleep that. Okay, sorry.
B
They are not a substitute for thinking. Like, I think people go audiobook. That's just coming in through my ears. Podcasts, that's just coming in through my ears. It's not the same thing. Like, I think one of the fascinating things to me about, like, the Rogans of the world is how the listeners manage to convince themselves that they are listening to something intellectually rigorous and not like, dudes bullshitting.
A
Yeah, I was listening to you on another podcast, do this rant, and you were talking about, you know, you turn on this podcast, and it's just two guys talking, and they're pretending to be experts on things, and you think you're doing something intellectually rigorous. And I was like, wow, I'm getting read for filth right now by Ryan Holiday.
B
I think I recognize this because my parents were big. I'm from Sacramento. That's where Rush Limbaugh started. There was always talk radio on. And I remember I was just driving. I was just visiting my parents. I was driving down from Lake Tahoe to Sacramento, and I had this sense memory of where in the drive the Sacramento talk radio station would kick in because the reception was good enough. And so there's a reason, like, house painters and construction workers and truck drivers listen to talk radio. It's possible to hear it while you're doing something else, because it doesn't actually require your attention, but it's still kind of going in your brain. And so there's something about our sort of media culture that's kind of passive, like, passive consumption. And look, I think that's good to a part. I listen to podcasts. I listen to yours. I like Ezra Klein. I like. I'm sad that Marc Maron's podcast is ending. I like Theo Vaughn sometimes. Like, I've listened to Rogan. I listen to these shows, and it's not a problem. It's just not a substitute for any actual intellectual work. Right. And there needs to be. I think most people are consuming way too much real time information and way too much commentary, and they're not consuming enough biography, history, psychology, philosophy. Like, it's like, read a fucking book. Like, I don't know how to say, like, obviously I'm an author, but go read a fucking book. Like, like. And not. Not just the books that you buy at Costco. You know, like, read real books that challenge you, that make you uncomfortable, because that's how you learn, and that's how you understand what's happening in the present moment.
A
I also would say read and listen to either way news that occasionally makes you uncomfortable.
B
Totally.
A
As you're just going through that list, I'm sure what you say through Ivana, some people are like, oof. And it's like, well, Theo's not probably the best example of this, because with love to my fellow Louisianan, he's kind of dumb. And dumb people can have great characteristic traits, by the way. He's got a lot of other good traits. But there is news that you can consume that also challenges a little bit, and that's okay. And I do worry that we're all retreating to a place and I worry about this especially with AI coming where we only consume information that makes us comfortable. And so even if we're not achieving your main goal of reading something from the Ancients that makes you uncomfortable because it's hard to process, a minimum first step would be consuming information about what's happening in the present day, at least sometimes that like, get you out of your comfort zone. I do think that's important brain work.
B
No. And look, I'll credit my parents with this. They listen to Rush Limbaugh all the time. The Rush Limbaugh newsletter came to our house and I would read it. I thought it was fascinating. And I thought he was smart. You know, like, I thought this is what, like I get this sort of attraction to young men, to the sort of alt right world, because I get the, the power and the energy that comes from being that sort of arrogant truth teller. And then I remember like Al Franken or something came out with that book where he's like, rush Limbaugh is a big fat idiot. And I saw that in the store and I was like, hey, can I get this? And my dad was like, go for it. It was the first time where I was like, oh, this guy isn't the smartest person in the world. And actually he's like, other people think he's a moron. Like, it totally. You have to deliberately and consistently be popping that information bub bubble or that bubble of certainty, or you can end up in a pretty dark place pretty quickly.
A
All right, to that point on men, you're material giving us the Stoics. It's the Roman Empire. There's that meme going around last year about guys. It's like, when was the last time you thought about the Roman or girls who asked their boyfriends, like, when was the last time you thought about the Roman Empire? And they're all like, three days ago yesterday. And the women and the gays were all like, never. I can't remember the last time at the toga party in college. There's something about the Roman Empire that straight men are into. Straight men were even more for Trump this past time than previously, including kind of some non political types. So I think that does overlap with your world a bit. Right? Like somebody who's like not a partisan political person who's a relative, middle aged to young guy that's interested in reading about Marcus Aurelius. Those people were moving to Trump. And I just wonder if you have any thoughts for Dems on, on what they could do to reach that audience better. Like what they're screwing up. What might be a smart strategy.
B
Look, they could try, right? I think they seeded the space. Guys like history, they like World War II, they like the Roman Empire, they like sports, they like comedy. These are things that regular human beings like. Regular human beings. You would be amazed the number of people that have been to a Tony Robbins seminar. Right. Like, it's not my cup of tea exactly. But like most of the people you know probably have and if you don't know anyone that has and you think only those people are morons, you're falling prey to that. What's that thing about, like, do you know anyone that owns a truck? If your world doesn't include people that are into self help and into history and into comedy and sports, like you're living in an, in the most abnormal world that there is. And I think part of the problem is that not only have these sort of thinkers like not engaged in that space, but they sneer at it and they look down on it. And so by not engaging with it, what they've done is not just removed their ability to reach those people, but it's like these conspiracy theories about like, you know, whether Churchill is actually the chief villain of the Second World War. Like that sort of anti Semitic conspiracy theory that they could. That's because there aren't enough interesting people. Like the people are like, where's the Joe Rogan of the left? How about just talking about the stories that regular Americans are interested in? Like Bill O'Reilly pulled a genius move by rewriting all these famous history things as like books you buy at the airport. And it became an entry point for sort of political radicalization also. So I talk about things that people are interested in. I just happen to not be red pilled. And that sometimes surprises people on the left. Like I talked at the White House right after the election. It would have been nice had they reached out when I could have helped. But I remember I was doing a talk, they had me do a Q and A to staffers who were leaving the White House and it was in the Indian Treaty Room. I don't know if you're supposed to say that, but that's what it's called. And this guy gets up and he goes, when I heard you were coming, I didn't Know if you were gonna be a white nationalist or not?
A
No.
B
And it was like, yeah, we ran the audio of my podcast. But it's like he thought, guy who talks about stoic philosophy is gonna be like a white nationalist misogynist because that's in his mind. That stuff is coded in that. That has been the field that has been ceded to perhaps even a generation of sort of influencers and celebrities now.
A
Which is so crazy because when I hear you talk about this stuff, there's so many potential entry points for Democrats into it. And I just. And like, when I did your show after my book came out, it was the time that, like, I heard, like, the texts I get. It was from, like, you know, 35 year old, like, guys I'd worked for on Republican campaigns that are, like, not so maga, but are kind of soft. And, you know, I'm like, if that's the representative group that is listening to this show, like, that's a really important group for Democrats to talk to. Right. Because it's not, you know, like, the people that are listening to Matt Walsh's show or whatever are not gettable. Right. Like, that's a waste of time. Right. But like. But there is another kind of group. And, you know, if they're listening to you but like, the rest of their information diet is all of this, like, kind of maha red pill, whatever stuff, then, you know, it's not that surprising that they get sucked into that direction, you know, and it's not as surprising, especially if, like, Democrats aren't engaging with, like, the entry points that are available like yours, you know?
B
Yeah. Not only are they not engaging, it's just. There's just this huge gap in the market. It's like, what are. What are young men listening to at the gym or on their commute? This isn't to say that it should all be this Trojan horse for political content, but the point is you're supposed to be showing that not everyone thinks that masked agents should be pulling people off the street. You're missing just the chance to reiterate basic values. I think sometimes people get mad at me for being political. They go, what would the stoics think about this? And I go, the ones who were literally senators, they probably wouldn't mind, but, like, I don't feel like I talk about policy really at all. I talk about, like, social contract stuff. And that's where they've really lost the opportunity to just be like, hey, here are the things we do. Here are the things we don't do. Here's what a good life is about.
A
Here's what being a good man is about. Your dad's show. Here's what being a good dad is, what being a good man is. It's not like having temper tantrums and picking on the most vulnerable people.
B
Totally.
A
You know, like basic stuff.
B
Totally. Like, what I try to do when I recommend books is like, hey, here's a book. Like, I'm not going to tell you anything, but you can't read this 300 page book and not have it open your mind up to things. Right. Like, I think books are just such a great. Especially history, because history is not partisan. Right. History is the past. And so how do you get people to read things that show them? Oh, actually, this is how I should be understanding what's happening here in the past. And then I think part of the reason that Trump, to you and I, who are decently versed in history and precedent, so much of what Trump is doing is shocking and appalling and not at all like any of his predecessors in any party. But if you don't have the historical basis, you're not going to know that. So, like, the Democrats talk about norms, but that presumes that people know what the norms were. Right. You haven't been educated. You've been so obsessed with showing how Thomas Jefferson was the worst person who ever lived that you missed the opportunity to talk about the places where he got it exactly right. And so you've been, you yourself have also been chipping away at those norms by not teaching them to a new generation or reiterating them. Washington leaving after two terms, he does that because it's a nod to Cincinnatus, the Roman statesman. But how many people would know Cincinnatus, let alone know that Washington left voluntarily after two terms? And so if you don't sort of highlight greatness and dignity and decency over and over and over again, I think you're asking a lot of people to be appalled when they see Trump act the way that he acts.
A
Ryan Holiday, I appreciate you so much, man. This is so great. If folks are in the Austin area, the Painted Porch Bookshop, that's what you referenced out in Bastrop. I went there. It's cool. It's a good vibe. It's a little strip. It's a little place. You get lunch out there. Take a little afternoon trip outside of the bustle of Austin. The book is called Wisdom Takes Work. It's a daily stoic. Appreciate you, man. Hopefully we'll see you soon.
B
Thanks for having me?
A
Who's the boy I like the most? Is it teasing you with underage? Could he be waving from a tropical sunset?
B
Static silhouette somehow single in his bed Someday quiet till it fall Fall, falls.
A
Roam, Roam Roam, Roam Focus, looking forward.
B
The Coliseum. Oh, no. What did I say? What can I say?
A
Roam Ro. Many tears are falling here. I'll be driving you look the other way. Valerie's it to annoy.
B
Shutters open all the way.
A
Hey. The Bulwark Podcast is produced by Katie Cooper with audio engineering and editing by Jason Brown.
The Bulwark Podcast | Ryan Holiday: Life Is Too Short to Be a Bootlicker
Date: October 24, 2025
Host: Tim Miller
Guest: Ryan Holiday, writer/philosopher, author of "Wisdom Takes Work"
This episode takes a step back from the frenetic political news cycle to explore deeper themes of stoic philosophy, personal courage, and the dilemmas of living in a turbulent political era. Host Tim Miller is joined by Ryan Holiday, bestselling Stoic writer, for a candid, wide-ranging conversation. They discuss current political challenges, the dangers of sycophancy and authoritarianism, the importance of self-reflection, the impact of information diets, and how stoic wisdom can guide us through personal and collective storms.
Tim Miller begins with an analysis of political developments in redistricting, affecting Democrats' prospects in 2026 and 2028.
Steve Bannon's Provocative Trump 2028 Claims (06:05+):
"This is an angle. This is a bit. He wants attention for himself." – Tim Miller (06:07)
Ryan Holiday joins, and is asked about the daily experience of hearing extreme pro-Trump sycophancy.
"The lengths that humans will go to degrade themselves to maintain their access and influence." (16:42)
On Personal Integrity & Stoic Opposition:
Ryan: "Life’s too short to be a bootlicker." (18:12)
He recounts the ancient Stoic ‘red thread’ metaphor: be yourself, don’t mute your identity even in the face of power.
"Everyone else can be the white threads. I prefer to be the red thread in the garment that makes it beautiful." – Ryan Holiday paraphrasing Agrippinas (18:39)
He asserts that confronting aspiring autocrats demands wisdom, ethics, and courage — even at personal or professional risk.
Background:
Holiday describes being uninvited from delivering his annual U.S. Naval Academy lecture after refusing to omit slides about banned books, including a Maya Angelou title, and the importance of engaging with uncomfortable ideas.
Institutional Fear:
"It’s not like the carrot and the stick. It’s two sticks." (27:27)
The Folly of Appeasement:
"When you compromise with an extortionist, you just get more pressure and extortion." (28:36)
Hypocrisy of Free Speech Advocates:
Holiday’s New Book:
The theme is the battle against the "fool within and without".
True wisdom isn’t just knowledge, but actively suppressing foolish impulses, bias, and self-deception.
"Wisdom isn’t just this kind of acquisition of knowledge and facts... a big part of it is just keeping that stupid part of yourself in check." – Ryan Holiday (32:34)
Cautionary Tales: Elon Musk and Peter Thiel
Miller and Holiday discuss how extraordinary success (e.g., Elon Musk, Peter Thiel) can foster ego-driven self-destruction.
The victory of a risky contrarian bet warps future judgment, causing one to ignore legitimate warning signs.
"Making a contrarian bet that turns out to be right can be a brain-destroying experience." – Ryan Holiday (36:01)
Trump is also cited: the surprise 2016 win taught him to disregard all dissent – with disastrous results.
The discussion covers the social echo chambers of the powerful, and how unchallenged ideas among elites (e.g., at dinner parties) escape into the mainstream, sometimes with dangerous consequences.
"They get used to trotting things out in these dinners... then when it emerges in public, it’s subjected to the marketplace of ideas, where it is swiftly dismantled and destroyed." – Ryan Holiday (42:53)
Media Diet & Presidential Responsibility:
Our Own Media Consumption:
Miller pivots to listeners’ habits: Many anti-Trumpers are just as trapped in echo chambers as Trump’s Fox News-addicted base.
Holiday urges consuming less real-time commentary, more rigorous and challenging content.
"Podcasts are not a substitute for thinking... Most people are consuming way too much real time information and way too much commentary, and they’re not consuming enough biography, history, psychology, philosophy. Like... read a fucking book." – Ryan Holiday (53:15)
Embracing Discomfort:
Both advocate consuming news and perspectives that occasionally unsettle: "If you’re only consuming information that makes you comfortable, that’s a problem." (55:39)
Holiday shares a personal lesson: learning to challenge his own conservative upbringing by reading critiques, which burst the bubble of absolute certainty.
Stoicism’s Appeal to Men:
Miller notes the Roman Empire fascination among straight men—and their increasing alignment with Trump (57:30).
Holiday says Democrats have vacated the cultural ground young men care about (history, self-help, sports, comedy), leaving it to right-wing influencers.
"If your world doesn’t include people that are into self-help and into history and into comedy and sports, like you’re living in the most abnormal world there is." (58:30)
There’s a "huge gap in the market" for content that affirms mainstream values and connects via shared interests. Democrats should engage rather than sneer at these entry points.
The Power of History for Norms and Values:
"So much of what Trump is doing is shocking and appalling... But if you don’t have the historical basis, you’re not going to know that." – Ryan Holiday (63:28)
On Bootlicking and Courage:
“Life’s too short to be a bootlicker.” – Ryan Holiday (18:12)
On Wisdom and Self-Control:
"Wisdom isn’t just this kind of acquisition of knowledge and facts... a big part of it is just keeping that stupid part of yourself in check." – Ryan Holiday (32:34)
On the Dangers of Contrarian Success:
"Making a contrarian bet that turns out to be right can be a brain-destroying experience." – Ryan Holiday (36:01)
On Authoritarian Appeasement:
"When you compromise with an extortionist, you just get more pressure and extortion." – Ryan Holiday (28:36)
On Information Diets:
"Podcasts are not a substitute for thinking... read a fucking book." – Ryan Holiday (53:15)
On the Power of Unchallenged Elites:
"They get used to trotting things out in these dinners... then when it emerges in public, it’s subjected to the marketplace of ideas, where it is swiftly dismantled and destroyed." – Ryan Holiday (42:53)
The episode closes with Miller and Holiday reflecting on the enduring wisdom of history, the importance for individuals—and political movements—to confront uncomfortable truths, and the need to cultivate moral courage in times of stress. Holiday’s call to "be the red thread" serves as both a challenge and a message of hope for listeners yearning for sanity, decency, and clarity amidst political and cultural turbulence.
For more from Ryan Holiday: