Ryan Holiday: Life Is Too Short to Be a Bootlicker
Ryan Holiday joins Tim Miller for the weekend pod.
show notes
Press play and read along
Transcript
Master distiller Jimmy Russell knew Wild Turkey Bourbon got it right the first time. So, for over 70 years, he hasn't changed a damn thing.
Our pre-prohibition style bourbons are aged longer and never watered down, so you know it's right too.
For whatever you do with it, Wild Turkey 101 bourbon makes an old-fashioned or bold fashion for bold nights out or at home.
Wild Turkey Bourbon, aged longer, never watered down to create one bold flavor. Copyright 2025 of Harry America, New York, New York, never compromised, drink responsibly.
What if your data team could be 10 times more productive? Most teams waste hours switching between fragmented tools, rebuilding the same analyses, and debugging AI chatbot outputs.
Hex integrates the whole analytics cycle, deep analysis, self-serve, and trusted context in one platform. The result, faster insights, higher trust, less tool sprawl.
Transform your data team from a dashboard factory to a strategic insights engine. Join teams from Anthropic, Lovable, Ramp, and 1,500 other customers at hex.ai.
Hello, and welcome welcome to the Bulwark Podcast. I'm your host, Tim Miller.
Our guest today, Ryan Holliday, 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.
I'll 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 Hanby 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 and 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 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, 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 was 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 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 that doesn't really matter for this year, but it is encouraging that at least, you know, there's some action out there in Colorado.
Now, I asked J.B.
Pritzker about this. I leaned in on this pretty hard.
And it's up to Illinois and Maryland. Westmore and J.Britzker both looking at 2028 races.
Probably they can both only squeeze out one seat apiece out of Illinois and Maryland. And Illinois in particular has 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 one 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 on J.B. Pritzker and Wesmore 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, 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...
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 effort 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 The 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 in 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 will be the president in 28.
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 Fengali-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 is 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 is 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 we happen in 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? Like, 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? You know, it's just, 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 incentivized in the pundit sphere to come on in a moment like this and be like, see, he's going to do it.
Trump is trying to stay in 2028.
Or to go out there and be like, Trump's never going to be able to stay. There's no chance he's going to stay.
Like, that is, you know, 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. Like, the right way to think about this is that
can we completely waive this off? Of course not. Is he absolutely going to do it? It doesn't seem like it to be.
Like, 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, the 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 it in the aftermath as far as 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 the pro-democracy movement, media, folks like us, something that I've been talking to Joe Perticoan 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 a certain places. You know, I'm sure the senator in the Senate race for Alabama to replace Tommy Toberville, 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,
you know, burnt Sienna makeup. He already has like these massive hand bruises.
You know, he's walking with a limp.
Like he, his hair, like, look at what is happening with it 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 the fact 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 jd 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 can 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. It's like, ooh, I'm really scared.
I'm quaking in my boots 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. We 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 the legal community, our friends, society for the rule of law, Mark Elias, all those guys, you know, 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 a 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 at the dailystoic.com and on the Daily Stoic podcast. It's Ryan Holliday.
What's up, man? Hey, thanks for having me. 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.
Oh, yes, yes, we did. 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 going to do any dad talk on this one. Folks can go into the archives.
All right. I want to 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. Yes.
So maybe they're like taking it 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's law enforcement roundtable at the White House.
Let me just say, Mr. President, that this country was going to die without you.
This country was going to actually die without you. That's what we were facing in 2024.
We've been invaded for four years. Our communities were sinking.
Our public safety had gone to zero. Cartels are running entire communities.
Hmm.
There you go. The country was going to die.
In the face of that,
how do you process it? Can you imagine how much money you would have to be paid to have to say that to someone?
There's no number for me. 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've 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 is 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 he could be.
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 lavishing with praise in service of his
efforts to make things better. I don't want to go that far because Seneca is actually very smart and probably
fundamentally
not an insane person. So I bizarro.
Bizarro. Inverse.
Did you not see the Bizarro Seinfeld episode? It's like bad Seinfeld. I did.
Of course. Yes, I get what you're saying.
I just mean for all time in the royal courts. Sure.
The person whose position is dependent on
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's 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 like endlessly fascinating.
And the lengths that humans will go to degrade themselves to maintain their access and influence.
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. Yeah.
So I'm 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 I'm just kind of wondering how you're sort of processing, navigating that, you know,
given the threats. Yeah,
I was both pleased and horrified that my son in the backseat of the car, you know, I was like, hey, do you want to go to this thing? And 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 immigrants.
So I, although 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 eight-year-olds. I don't know if that counts for temperance.
No,
no. 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 this sort of moral philosophy, an ethical framework, and philosophy for rationality. I just think
life's too short to be a bootlicker, you know? And there was 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 Domitian. At one point, the Stoic philosophers were such perpetual thorns in the side of the sort of powers that be that all philosophers are banned from Rome.
So Epictetus spends the rest of his life in exile. There's this Stoic named Agrippinus who's fascinating, who's told, you know, why don't you blend in a little bit more? Isn't this dangerous?
And he goes, you know, everyone else can be the white threads. I prefer to be the red thread in the garment that makes it beautiful.
His point is like, you should be yourself.
You shouldn't mute your colors. So 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 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 ethics and right and wrong to know what's obviously right and wrong.
And then you have to have the courage to say it, even though it's not always, you know, good for business. Do you need to have the wisdom to not let it consume you? I do.
I do.
I think when I think about the ancient world,
I'm always bemused at our tendency to idealize it. Like we think of like Socrates as this guy walking around in a toga in this beautiful, you know, idyllic, peaceful society.
The Athens 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 the 30 tyrants.
Like one tyrant is bad, 30 is really, really bad. And 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.
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 it 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 you have for the last couple of years at least.
And you'd sent them a PowerPoint, I guess, about what you were 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.
So, yeah,
I've 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'd put together the...
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. Well, extremely woke, as I was going to 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 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 mention 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 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
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.
And then even worse, remove said mention. under pressure, you know, under political pressure.
Like I'm a private citizen.
That was a bridge too far for 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.
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 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 hit because they're scared of trump cracking down on them if they allowed wrong talk that that that's actually the i think the crux of it you know 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 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.
Did you hear from any
of the big free speech types on the right after this happened?
Anybody come to you and say, hmm, I'm a little concerned about this.
The government is canceling a speech on Stoic philosophy. Yeah, you can imagine all the cancel culture people that have been really loud the last couple of 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.
No, I think fire. You're not on the Bench of Hero show
next day as a hero of the the free speech movement.
I was not.
And,
you know, I think Fire.
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 going from.
They put in a freedom of information request, which I'm interested to see when it eventually comes out. Because 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, 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 right like not because she wasn't going along with what what they wanted she clearly was 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? No, she's the superintendent of the Naval Academy. Okay.
So the woman that was the superintendent of the Naval Academy, like either made the decision or was, you know, 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, you know, a lot of the same reasons why they wanted to cancel your speech, like this overly concerned about DEI and, you know, diversity, things of that nature.
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 not 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.
This episode, sponsored by BetterHelp, was trying to 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 U.S.
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 in industry-leading match fulfillment rate means that 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 recs. 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, you know, I found a therapist, Dr. Sharp, who I just will always appreciate, helped 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 in on the show because he dumped a couple of 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 listeners get 10% off their first month at betterhelp.com slash the bulwark.
That's better, H-E-L-P dot com slash the bulwark.
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. 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 is this 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. 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, right?
Like big super fans of Elon Musk and people that have come to really loathe Elon Musk and have like 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, you know, that like.
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.
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, that's more or less.
Edward Norton plays like an Elon Musk character, and it's 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 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. That's interesting.
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. Like, 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. Really? 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 good bet.
But if you look at from there to here, right, that's the brain-destroying experience. Like when you make a bet and everyone else thinks it's dumb, this happens to entrepreneurs, artists all the time.
You do something and everyone tells you it's a terrible idea. And then it turns out it was a good idea.
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.
And this is Trump himself. And obviously, it's people that bet on him, but it's Trump himself.
He didn't think he was going to win in 2016.
And so now, how could somebody, 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 time where he doesn't even receive, like forget receiving dissenting views and rejecting them. Now he's not even receiving them.
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 style intervention. Like, you cannot do this.
You will lose all of your money.
So they were wrong in that case. Now, was it a very risky, perhaps even reckless bet? Yes, right?
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.
At Carrington College, we're ready to help you begin your next chapter. We've been helping students launch healthcare careers for over 55 years.
Our hands-on programs in nursing, medical assisting, pharmacy technology, and more are taught by experienced, real-world professionals.
With programs completed in as little as 9 to 12 months and convenient learning options, we make sure your education works with your life.
Classes start soon in Pleasant Hill, San Leandro, and San Jose. Visit Carrington.edu to find out more.
Programs vary by location.
For information about student outcomes, visit Carrington.edu/slash SEI.
Escape to a Mexico rarely seen. Uncruise Adventures offers Baja, California on this all-inclusive journey on the 66-passenger Safari Voyager.
Snorkel with sea lions, paddle turquoise bays, kayak hidden inlets, hike rugged coasts, savor locally sourced flavors, and enjoy a cocktail beneath fiery sunsets. Adventure without the crowds.
Unrushed, unplugged, unbelievable. Uncruise.
Visit uncruised.com or call 1-888-862-8881.
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 like pick your brain on it.
And obviously Peter's now out there doing the Antichrist lectures. South Park did a big takeout on him.
And everybody makes the obvious joke about how like somebody who is transforming physically into kind of a demon-looking creature
who is obsessed with the Antichrist, you know, maybe should be looking internally. I'm just like wondering, is it just the succeeding on the contrarium bet? Was there anything else you thought about?
I mean, 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 Mal? Like, to have all of that insight and power and use it how he has is pretty dispiriting.
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.
Yeah, I'm sure same. But I was usually kind of like the
diversity invite, right? Like I'm not like the others. Maybe they know my 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. 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.
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, 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 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 yeah 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 teal famously wrote this op-ed many years ago the famous line is he believed that democracy, was it democracy and multiculturalism, I think?
Yeah, are no longer compatible. He basically wrote like a piece that in some ways argued against women's suffrage.
Now, this isn't totally a fair interpretation, but 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.
Yeah, you were right. It was capitalism.
It was in the same book about how multiculturalism and diversity is bad.
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, but 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. Is it possible that Peter Thiel is actually a supervillain, though? And that it's just leaking out.
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.
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.
Yeah. But like when Bannon says it, like that's about Bannon.
Like 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, you know,
powerful, 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, you 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 an example. I want to talk about Trump first, and then I want to talk about all of us.
So talk about the example you use for Trump and the information diet. Have you ever heard those reports of like Kennedy's, all the drugs Kennedy was on when he was on?
And then one of his doctors finds out and he goes, you know, no one with their finger on the button should be taking anything like that.
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 it home for me. So I was reading this Rolling Stone profile of Kid Rock, which is a fascinating article.
And in it, Kid Rock's about to go 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 TV. And then Trump like turns it on and watches it.
Right. And you go, okay, 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.
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 is on in the background, like always doing, you know, Fox cable news, brainstorm.
It's not good for your psyche because this is an artificial, radically cranked-up up version of reality. To be a leader requires a certain amount of reflection and sobriety and perspective.
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 a great president, not anymore.
But like, he was at least, I mean, George W. Bush reads The Great Influenza by John M.
Berry and puts in place the pandemic preparedness response group that Trump disbands in, you know, like 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.
Your global campaign just launched. But wait, the logo's cropped.
The colors are off. And did legal clear that image? When teams create without guardrails, mistakes slip through.
But not with Adobe Express, the quick and easy app to create on-brand content. Brand kits and lock templates make following design guidelines a no-brainer for HR sales and marketing teams.
And commercially safe AI powered by Firefly lets them create confidently so your brand always shows up polished, protected, and consistent everywhere. Learn more at adobe.com slash go slash express.
Our diets today are dominated by ultra-processed foods packed with sugar, low in fiber, and cause issues like diabetes and high blood pressure.
What if you could transform that processed food into real food that nourishes your body? That's what MonchMonch does.
It absorbs excess carbs and sugars from the food you eat, blocking them from your body so you can enjoy your favorite meals with fewer calories, more stable blood sugar, and better gut health.
It's like turning apple juice back into apples. Visit MonchMunch.shop today and start transforming your food into fuel.
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, the people I talk to, like myself, like overconfidence that we were so right, that Trump is horrible and bad like led to blinders yeah and just like going back to like my just speaking for myself like my original
and it ended up working out by accident but 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 are you aren't you a little worried that he's going to become the president and like you will have been on tv like and he seems vindictive and i was like this guy this fucking clown can't win You know, so oops.
But I feel like that same underestimating of him has
plagued us for years now. Yes.
Decade almost.
And many other things.
Just like the sense that you're right always about everything and that the other side is idiots, you know, can lead to misjudgment about the fact that, you know, you're not always going to bat a thousand.
Yeah. So 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 like, 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 in 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 in 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, right? 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 like a big part of their success.
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, that their information diet in Trump 2.0 isn't a ton better than Trump's.
I mean, like, you know, 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? To be 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, like 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 thoughts you have for somebody that might be in that boat. 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, no.
Podcasts are not a substitute. Okay, we got to bleep that.
Okay, sorry.
They are not a substitute for thinking. Like, I think people go, audiobook, that's just coming in through my ears.
Podcast, 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 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.
Yeah, I was listening to you on another podcast do this rant and you were talking about, you know, two, 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 red for filth right now by Ryan Holiday. I think I recognize this because my 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 like 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 apart. I listen to podcasts.
I listen to yours. I like Ezra Klein.
I like, I'm sad that Mark Maron's podcast is ending. I like Theo Vaughan sometimes.
Like, I've listened to Rogan. I listen to these shows.
It's not a problem. It's just not a substitute for 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 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.
I also would say
read and listen to either way, news that occasionally makes you uncomfortable. Totally.
Because you were just going through that list.
Like you, I'm sure what you say through Rovana, some people are like, oof. And it's like, yeah, well, Theo's not probably the best example of this because.
Yeah. With love to my fellow Louisiana, 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 like, there is news that you can consume that also challenges a little bit.
And, like, 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, like a minimum first step would be like consuming information about what's happening in the present day, at least
sometimes that like gets you out of your comfort zone. I do think that's important brain work.
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 the sort of attraction to young men to the sort of alt-right world because I get the power and the energy that comes from being the sort of, that sort of arrogant truth teller.
And then I remember like Al Franken or something came out with that book where it'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 bubble or that bubble of certainty, or you can end up in a pretty dark place pretty quickly.
Cal State East Bay was founded on a belief that every student holds incredible potential.
And when that potential is unlocked, doors open to opportunity, to purpose, to a better future for their families and communities.
Our students are modern-day pioneers, breaking new ground and paving the way for generations to come.
Here, they find an intellectual oasis, a place to pause, reflect, and rise, gaining the knowledge and confidence to make their mark on the world. Enroll today at csueastbay.edu slash start
at Carrington College. We're ready to help you begin your next chapter.
We've been helping students launch healthcare careers for over 55 years.
Our hands-on programs in nursing, medical assisting, pharmacy technology, and more are taught by experienced real-world professionals.
With programs completed in as little as nine to twelve months and convenient learning options, we make sure your education works with your life.
Classes start soon in Pleasant Hill, San Leandro, and San Jose. Visit Carrington.edu to find out more.
Programs vary by location.
For information about student outcomes, visit Carrington.edu slash SEI.
All right, to that point on men, you know, your material, giving us the Stoics, it's the Roman Empire.
There's that meme going around last year about like, guys, it's like, when was the last time you thought about the Roman or girls would ask their boyfriends like, when was the last time you thought about the Roman Empire?
And they're all like, three days ago, yesterday. You know, and the women and the gays were all like, never.
I can't remember the last time of 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 like that does overlap with your world a bit, right?
Like somebody who's not a partisan political person, who's a relative, you know, middle-aged to young guy that's like interested in
reading about Marcus Aurelius. Those people were moving to Trump.
And I just wonder if you have any thoughts for Dems on
what they could do to reach that audience better, like what they're screwing up, what might be a smart strategy? Look, they could try, right? Like I think they seeded the space.
Like 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.
Like regular human beings, like 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 is have these sort of thinkers like not engaged in that space, but they sneer at it and they look down 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 um
churchill is actually the the chief villain of the second world war like that sort of anti-semitic conspiracy theory that they go that's because
There aren't enough interesting people talk 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, you know, 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, you know, when I could have helped.
But, like, I remember I was doing a talk. They had me do a QA to staffers who were leaving the White House.
Yeah.
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 going to be a white nationalist or not. No.
And it was like, yeah.
We ran the audio of it on my podcast, but it's like,
he thought the guy who talks about Stoic philosophy is going to 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 seeded to like perhaps even a generation of sort of influencers and celebrities now.
Which is so crazy. Cause like when I hear you talk about this stuff, like there are 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, you know, 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 that surprising especially if like Democrats aren't engaging with like the entry points that are available like yours, you know?
Yeah. And 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?
Like 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 like not everyone thinks that, you know, masked agents should be pulling people off the street.
Like you're missing just the chance to reiterate basic values. Like, 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 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.
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.
Totally. You know, like basic stuff.
Like what I try to do when I, 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 here in the past.
And then I think part of the reason that Trump, like 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. You know, Washington leaving after two terms.
He does that because he's, it's a nod to Cincinnatus, the Roman statesman. But like, 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.
Ryan Holiday, I appreciate you so much, man. This is so great.
If folks are in the Austin area, the painted porch bookshop is what you referenced out in Bass Drop. I went there.
It's cool.
It's a good vibe. It's a little strip.
You know, 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 be seeing you soon. Thanks for having me.
Who's the boy you like the most?
Is it teasing you with underage?
Could he be waving from a tropical sunset?
Static silhouette somehow.
Single in a fit sunlight
Quiet till it falls, falls, falls
Roam, roam, roam, roam, focus looking forward, knuckles to you.
All that I say, what can I say?
Roam, roam, many tears are falling here. I'll be driving you look the other way.
Dial and easy to ignore.
Shutters open all the way.
And it's candlelight, I see how the went the same.
Distant silhouette somehow.
We shared a cigarette somewhere.
I look to the ball,
boss.
No, no, no, no, focus.
Looking forward. But closely, is the oh no, no, what did I say? What can I say?
Oh, no, many tears are falling here. I'll be driving you the other way.
The Bullwork Podcast is produced by Katie Cooper with audio engineering and editing by Jason Brown.
What if your data team could be 10 times more productive? Most teams waste hours switching between fragmented tools, rebuilding the same analyses, and debugging AI AI chatbot outputs.
Hex integrates the whole analytics cycle, deep analysis, self-serve, and trusted context in one platform. The result, faster insights, higher trust, less tool sprawl.
Transform your data team from a dashboard factory to a strategic insights engine. Join teams from Anthropic, Lovable, Ramp, and 1,500 other customers at hex.ai.
Looking for an exceptional driving experience? Find it behind the wheel of a Mercedes-Benz SUV.
Experience the power, precision, and intelligence of an iconic Mercedes-Benz SUV at your local Mercedes-Benz dealer today.
What if I told you there was yet another tool where you could get surface-level data insights in static, uninformative dashboards?
There are 170 of these products, and luckily for you, we're not one of them.
Hex is a new platform for working with data. We combine deep analysis, self-serve, and trusted context in one platform with purpose-built AI tools for data work.
Over 1,500 teams like Ramp, Lovable, and Anthropic use Hex.
Learn why at hex.ai.