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Ryan Holiday
Welcome to the Daily Stoic Podcast, designed to help bring those four key stoic virtues, courage, discipline, justice, and wisdom into the real world. Hey, it's Ryan. Welcome to another episode of the Daily Stoic podcast. You just never know how stuff's gonna work out. You never know if you're gonna get the break if you're not gonna get the break. I remember back In April of 23, I was putting out the Daily dad and I was supposed to do CBS this Morning, which is a huge win.
Stephen
I was so excited.
Ryan Holiday
You know, I thought, that's as good
Stephen
as it's gonna get.
Ryan Holiday
It's amazing. And then we got this call from the Daily Show. The Daily show wanted to have me on. Jordan Klepper was the guest host.
Stephen
I brought you part one of his
Ryan Holiday
episode earlier in the week.
Stephen
They wanted to have me on.
Ryan Holiday
And so you might go, oh, that's amazing. But there was a conflict, which is CBS this Morning had the exclusive on the book. Like, we had to run any other appearances by them for approval. And naturally, they don't want you to go on another show first and then go do their show. And my wonderful publicists and the wonderful producers of the Daily show managed to work it out. They made an exception. So I got to go do the Daily show to talk about stoicism, and then a few days later got to go on CBS this Morning to talk about parenting. But like the Daily Show, I remember the first time I watched the Daily Show. Jon Stewart was the host, and I watched it. I was homesick one day, I think, in middle school, and I watched it on tv and I just thought, what is this? This is amazing. And I watch it sporadically. In high school, I would watch it every night. In college, actually, I went and saw a taping of the Daily Show. This would've been like the summer of 2005. So for me to come full circle and be able to be on the Daily show, it was amazing. Let me bring a little clip of that.
Jordan Klepper
Ryan, I've been a fan of yours for quite some time. You're a popular man. 12 best selling books. That's a lot of books. That's almost more books than I've read. But you have a lot of fans out there, from very successful comedians like myself to folks in the NFL to senators, sort of what you speak to goes across many aisles, if you will. And I will say I've taken a lot from some of the ideas you have. I will also say that you kind of, you talk about philosophy, and it helps me work through Life. And then a byproduct is then I go home and I tell my wife how she should work through life.
Ryan Holiday
That's a great idea.
Stephen
Yeah.
Jordan Klepper
And just before we get started, I wonder if it's possible for you to apologize to my wife for me.
Unnamed Female Speaker
People ask my wife what it's like living with a Stoic philosopher, and she usually answers, I don't know.
Jordan Klepper
That feels Socratic. But mostly maybe it's just passive aggressive.
Unnamed Female Speaker
Yes. One of us writes about it, and then the other is sort of natural.
Jordan Klepper
It kind of lives it.
Stephen
Yes.
Jordan Klepper
For those who don't know a Stoic philosopher, what are the tenets of Stoicism?
Unnamed Female Speaker
Stoicism, if I had to summarize it in one sentence, I would say it's this idea that we don't control what happens to us in life, but we control how we respond to what happens in life. And the Stoics say that basically every situation. Big ones, small ones, ones you wanted, ones you didn't want. It's all an opportunity to respond with these four virtues. The virtues are courageous. Discipline, justice, and wisdom. So the idea is that that is what life is asking from you. One or all of those virtues in some kind of a combination. That's what it's demanding of you. And what's cool about the Stoics is like, I think when people hear philosopher, they think like, you know, a tweed jacket or an old white guy in
Stephen
a toga or whatever.
Jordan Klepper
Sure.
Unnamed Female Speaker
But the Stoics were philosophers, they were thinkers, but they were also doers. The most well known Stoic is Marcus Aurelius, who's the emperor of Rome, the philosopher king. But there were Stoics who were slaves, who were soldiers, who were artists. There were men and women. There were people trying to do what we're all trying to do, which is make sense of the crazy world that we live in.
Stephen
Okay.
Ryan Holiday
And so the person interviewing me there was not Jon Stewart. It was Jordan Klepper, who is today's guest. He was in town for a live show he was doing at the Paramount Theater in Austin. I was very grateful that he was
Stephen
able to squeeze that in. I know what it is to sort
Ryan Holiday
of do press the same day you're doing a performance. So that was really cool. And then we got to nerd out about some books at the bookstore. In this episode, Jordan shares what it's like to do what he does, what it was like being at the Capitol. On January 6th, we talked about the First Amendment and his message to young people. I think you're really gonna like this. Part one was really great too and I'm excited to bring you part two of this episode now. Jordan is a writer, a comedian, a correspondent for the Daily Show. You can follow him on Instagram jordanclepper. You can check out his upcoming live show dates. He amazing. Very very funny@officialjordanclepper.com. It's funny. People want to level up their business, but they always focus on like big stuff and they neglect some of the small, basic stuff. Like how do you talk to your customers and keep your team on the same page? Sometimes just a cleaner, more modern setup can make everything feel smoother and work better. And that's why today's episode is sponsored by Quo Q U O the modern alternative to help run business communications KUO is the number one rated business phone system on G2 with over 3,000 reviews, and it's built for how modern teams work. More than 90,000 businesses, from solo operators to growing teams, rely on Quo to stay connected, professional and consistently reachable. Your entire team can handle calls and texts from one shared number. They don't miss messages. Conversations don't get disconnected. Everyone sees the full thread, making replies faster and customers feel genuinely cared for. And Quo isn't just a phone system, it's a smart system. Quo's AI automatically logs calls, generates summaries and highlights next steps so that nothing gets lost. Can even qualify leads and respond after hours, ensuring your business stays responsive even when you yourself are enjoying some much needed offline time. Make this the year where no opportunity and no customer slips away. Try quo for free plus get 20% off your first six months when you go to quo.comdailystoic q u o.comdailystoic no missed calls, no missed customers I know it's not good for me to just run. I need it for my mental health. But it takes a toll on me physically and I need to mix it up.
Stephen
So one of the things I'm trying
Ryan Holiday
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Stephen
When you do those interviews, the other thing I think about, it's always remarkable to me, is when you have what seems like a nice person nicely saying a horrendous thing, you know, like chatting with them. You get them to be like, yeah, maybe the Civil War was a mistake, or, you know, or. Or maybe we should just throw them all in jail. Or, you know, I can't tell what that is.
Ryan Holiday
What.
Stephen
What is your feeling about it? Like, are. Are they disconnected? Are they putting a smile on a horrible thing? Like, what do they think is happening?
Jordan Klepper
I think a few different things are happening. What I noticed originally, when Trump first ran in 2015, and then we went out there, birtherism was a taboo.
Stephen
Yeah.
Jordan Klepper
It was widely considered, at least among the masses and on television, I think, culturally, like a racist theory. Not that people didn't believe it, that there were people who had these feelings, but people weren't going on television and saying. And so if I were to go to a rally and talk to people, which I did when that was coming out, nobody would admit to the idea that Barack Obama wasn't born in America. So I went to an early Trump rally and would ask, go down that path, and nobody, maybe one out of 10, would allude to birtherism. And Trump started then talking about birtherism very openly and how he thought Obama was born in Kenya, yada, yada, yada. A couple months later, we were at, like, 7 out of 10 people talking about birtherism. And at that point, I don't think he changed that many people's minds, but I do think he completely changed the discourse of what was acceptable. Yes.
Stephen
What people would keep to themselves and what they would feel comfortable saying out loud.
Jordan Klepper
He has, like, this baseline of culture that gives permission for cruelty. He gives permission for some of your innermost thoughts that are perhaps Thought about without reflection.
Stephen
Yeah.
Jordan Klepper
That have unkindness and perhaps hate behind it or even ignorance behind it. I think those were suddenly elevated in a way that if he is talking about this, if the culture is talking about this, this, then I will be open about this. Now, I don't think everybody thought that was true. Again. I think there's another pocket of people that we're talking to who are just trying to be a part of the conversation and are catching up. And this apparently, is the thing that people are talking about now. When I see that, that is that mob mentality. Like, I've seen that at January 6, all different places where it's not everybody who believes this thing, but suddenly when you're a group of people who are all talking about this thing and such a powerful famous person tells you this thing, you go along with this thing. We're seeing so many people going along with it. And so I see it as a mix of Donald Trump raising their. Or lowering the bar of what is socially acceptable to reveal in public company and on television, as well as a mob mentality of, this is the thing I must talk about now because this is culturally where we're moving.
Stephen
Is that an argument, you think, for political correctness? Like, there's been this backlash against political correctness, but I think we might be throwing the baby out with the bathwater. Like, it serves a purpose to be. Like, hey, we draw some lines about what we do and say in public.
Jordan Klepper
I think. I think it definitely. It's an argument for integrity for people in positions of power.
Stephen
Yeah.
Jordan Klepper
I mean, you and I both know we hold very little power.
Ryan Holiday
Yeah. Yes.
Jordan Klepper
But we have microphones in front of us.
Stephen
Sure.
Jordan Klepper
And so even when pushed on more extreme topics and doing interviews elsewhere else, like, I'm sure you have an idea of, like. Well, these are the types of ideas that I want to push out into public and the ones I'm choosing not to.
Stephen
There's a carefulness.
Jordan Klepper
There's a carefulness that even at your most. I don't want to say unhinged, but open.
Stephen
Sure.
Jordan Klepper
You're still aware that there's a microphone that other people are listening to and take into account. I think most respectable people have that awareness. And it does make me look back on American history and say what you will about many of the presidents and people in charge of our country, but there was an understanding, a belief in the institution of the president of the United States, United States, that even in times of public distress, you're talking about people coming together. I think looking at what happened with the Charlie Kirk shooting. What became so frightening is, I think, Trump's response afterwards, just fanning those flames, and I hadn't fully put it together, be like, oh, right. When things like this normally happen, even if you don't buy it, the President comes on television and he sets the bar.
Stephen
Yes.
Jordan Klepper
And the bar is, these are difficult times. Violence is never acceptable. And we need to tone down the rhetoric and come together as a country.
Stephen
There's things the queen does and doesn't do or the king does or doesn't do, and it's this sort of performance role and that you're trained in understanding. This is what I do.
Jordan Klepper
I'm realizing, I think Americans have always been partially shitheads.
Ryan Holiday
Yeah.
Jordan Klepper
But we've also believed in this idea of better angels that we can ascribe to something more.
Unnamed Female Speaker
Yeah.
Jordan Klepper
And I think that's mostly perform. People in charge.
Stephen
Yeah.
Jordan Klepper
Some people are closer to actually believing that. But the baseline has always been, you got to still perform that shit.
Stephen
Yes.
Jordan Klepper
You got to still pretend like we are better than this, that we can achieve greatness in these types of ways, that we can come together and we hold ourselves in high regard. That was, at the very least, an empty performance, but it was still a necessary performance. And now you have this bar dropped to the point where the guy there has no problem being a dickhead.
Stephen
Yeah.
Jordan Klepper
But he feels no compulsion to pretend like he's better than that.
Stephen
Well, yeah. Even like, if. If you had 200 million Twitter followers and you're Elon Musk, you would think about the things that you say before you say them, because you would think about what would happen if even 1% of people took this seriously or it was misinterpreted. You would. You would be careful. Right. Just like you guys are. You have people. There's no law mandating that the Daily show have certain kinds of fact checkers
Ryan Holiday
or standards in practice.
Stephen
All of this is kind of voluntary, responsible behavior that you engage with because you're a business, you're owned by a corporation. There's just, like, these layers of like. And some people rightly push back on it as bureaucracy and frustrating, and it has some minor consequences, but it also prevents, you know, you're not giving unqualified medical advice or whatever, because, you know, that's dangerous.
Jordan Klepper
There's a baseline responsibility.
Stephen
Yeah.
Jordan Klepper
I think adults have.
Ryan Holiday
Yes.
Jordan Klepper
And we are so far away from that at times that I think you and I are. We're trying to wrap our heads around that, which, if you had 200 million followers a Baseline responsibility is not a crazy thing to assume that you would have in this conversation, but that baseline responsibility has been replaced with, like, the possibility or the idea of, like, edgelord politics is in of itself, like, more redeemable equality than basic responsibility. So that, like, success in being in nagging, being outrageous, crossing that line that it's always funny because comedy gets looped into this about, like, what can you say? And woke and all these kinds of things. But more often than not, the people that I know who go out there and do it have that baseline responsibility and choose to step over the line through a tactical nature because it's something they believe and they want to provoke in a very specific way. I think those who don't understand the baseline responsibility just, I think, are removing something that is not a creative choice, but more of a basic human quality that all adults should be expected to have.
Stephen
Well, the First Amendment debate is really interesting because we tend to focus on whether stuff should be legal or not. And it's like, it should definitely be legal, but you fucking suck if you say certain things. You know, it's been weird that we've kind of lost track of that. Like, obviously a whole bunch of abhorrent things are allowed under the First Amendment because if you make them illegal, a bunch of good things would also become illegal. But, like, we should have. Like, we should have no problem being like, only an asshole would do this or say this or think this. And so it's weird too. Like, obviously there's been this reaction against cancel culture, but there should be social consequences for saying and doing shitty, but not outright illegal things.
Jordan Klepper
Yeah, 100%. We should still have a basic morality or an understanding of like, oh, you, you are being irresponsible. You're being a dick. We can call you out for being a dick. And there can be. Yes, there should be consequences for that. Yeah, I think, like, what has gotten so interesting as of now is, like, that loose idea of cancel culture has suddenly been, again, we have so little both understanding publicly and respect for what government does that in that equation, people have gotten confused as to what a government can and should do. And so the fact that, like, the Trump administration is weighing in, leaning on the FCC and doing all these things, you're like, we're not talking about what culturally we're doing. We're talking about what, like, an elected government is now imposing. Yes, but we're all just lost in this mix of conversation that it all just feels like it's part of the same. Same stu.
Stephen
But I agree, like, there's something. There's something that shifted in the culture about what we accept or allow. Like, political assassinations are very, very bad. And you cannot have a civil society where people murder other people. Like, George Wallace shouldn't have been shot. John F. Kennedy shouldn't have been shot. RFK shouldn't. No one should be shot. Right.
Ryan Holiday
Charlie Kirk.
Stephen
It was weird to watch people struggle to wrap their heads around the fact that he said a lot of horrible things about people. Like, if you tweet that when you get on a plane you're suspicious of black pilots, you're a bigot. Like, that's the definition of what being a bigot is. Now, should you be murdered for that? No, of course not. But that's a shitty thing to say. It's a shitty thing to think. And just because you said a lot of other. Other things that people like doesn't mean that that doesn't really suck. And so, like, I think, like, they call it the Overton window, but just generally, the things that we've not held people accountable for for saying has gotten so bad that it all. I think it's all just kind of swirling around when those are the kinds of things. Remember, they got rid of a Republican. Was it the House Majority Leader who just complimented a segregationist, which. That seems like a good punishment that you. You should not be in elected office if you think segregationists were good. Like, that seems like a society that's getting better would swiftly deal with something like that. But, like, our ability to handle people who have abhorrent ideas shouldn't just be like, oh, just say whatever you want. You're cool. Like, again, you shouldn't go to jail and you shouldn't be murdered for them. But, like, I don't feel any compunction about going, like, you suck, dude.
Jordan Klepper
Yeah, we should be open to be critical of the things you say. Everybody who has a microphone in front of them is pushing out ideas and thoughts that people should be critical of those. They should have consequences for it. Obviously not consequences that are violent in any kind of a nature, but it speaks to, like, how our culture has such a hard time having an earnest conversation around this. That whole incident, it just became a tool for the culture war, where people who weren't even aware of who that person was, now it just becomes a thing that they can use to try to cancel somebody else for it and tighten speech. And then you also feel, because that happened, seeing people on the left shy away from being critical of the things that were said in a way that Double spooked me. Where suddenly we're putting up these boundaries here where we're right, we're now using the words that somebody said in the conversation about who this person was. Is now being deemed something you could be canceled is not how a republic should be working.
Stephen
No, it's also just not how like a moral society. It's like, okay, there's a video of Dana White hitting his wife. He's going to put on a fight on the lawn of the White House. Yeah, that's insane. First off, we don't need to be like, boxing's been a sport for a long time. They never even. Theodore Roosevelt wasn't like, let's have, who loved boxing?
Jordan Klepper
Bears could wrestle on the White House lawn. But people, let's not have that happen.
Stephen
Even he was like, this is, this is something we do in the dark, you know, but like, if there was ever a thing to be canceled for, that seems like one of the things, again, they shouldn't take all of his money. Although if it was a crime, you know, whatever, it's a crime. But it's interesting that we're just like, okay, yeah, you could. You get to still have your polite society card. But then somebody else over here, like some 20 year old kid that does something stupid is gone forever.
Jordan Klepper
This is where I get worried when we talk about these people who I talk to on the road who say stuff that feels abhorrent and you wouldn't expect it to come from them. I look at these conversations and you point to the actions of the most powerful person on the planet. The pardoning of J6ers, all of these actions. Suddenly I don't think if I talk one to one, and I do talk one on one with a lot of these folks at Magarellis off camera, what have you, kind people, I think your moral line is very similar to what yours or mine would be. But there's such a nihilism that comes with Donald Trump's view of the world. The fact that he's looking to pardon J6ers because they supported him, but also because it would piss off Democrats. So much of this has to do with pissing off people. He's talking about pardoning P. Diddy and people like, well, why would he do that? I think only just because it would piss people off. The Dana White of it all is it's there to piss people off. It's edgelord politics. And I don't think mom and pop in the middle of America give a shit about that. But in the last two Years, this seems to be what the competition is. And so like, if you're, like, if you bought the hat, you are a MAGA fan and this is your guy. And now this is the world of it all. You root for the actions of that. And these actions are so amoral and an edgelord in a way that now you have 65 year olds who are like, yeah, I guess I want people to beat each other up on the lawn. They're talking about Conor McGregor being the person who does it. Also, isn't he a rapist? Yeah, I mean, yeah. And he was brought into the White House. Trump shook his hand, talked like he's flaunting that. And I think these actions, again, baseline responsibility in the old. I'm not saying we didn't have terrible people in that Oval Office, but they knew not to. They knew to perform better and we are performing worse as an attempt to own half of the population.
Stephen
Yeah, There would be a system where a press or communications secretary would go, okay, here's a list of 10 boxer or 10 MMA fighters that we might have do this thing. Okay, well this one's a rapist, so he's out. And you know, this one did this and this one did this. Hey, these three are just as good as that one. So this is the safer political pick. And again, I think people took that as like somehow false or inauthentic. But it turns out that it's actually essential to a moral society that you make some judgments and that there's some kind of like, yeah, just mechanism by which you go, look, I'm not saying he has to go into exile, but he's not who we're gonna like. We each have this little bit of platform, this little bit of say. And how do we use that say, who are we endorsing and spending time with and who are we not?
Jordan Klepper
That just seems they will have that list now. And I don't doubt that they will articulate if they articulate who is a rapist and who is not. And I think instead of saying that that person shouldn't be a part of.
Stephen
This guy really likes me.
Jordan Klepper
He likes me.
Stephen
Yes.
Jordan Klepper
And this will piss people off. Yes, they indulge in the cruelty. And that's that Adam Serwer article. The cruelty is the point. I think that is such a big part of it. It's not all of it, but it's such a big part of it in these decisions. Wouldn't this piss these people off? They want the images of these ICE raids in Chicago. They want little K Zip Tied. And you get people one on one. I don't think they want that, but you get them in that gosh darn group and this person just froths at the mouth for that cruelty and lowers that bar. It's such a scary, despicable place to be.
Stephen
Well, the fundamental insight of the civil rights movement, we don't give them enough credit for their media savvy. They were like, we are going to force confrontations that are going to create an overreaction and then that cruelty will be documented by reporters with cameras, and then that will shock and stun the conscience of ordinary Americans. Gandhi did the same thing. Gandhi actually understood that fundamentally the British people were moral people. They just didn't fully understand what running India as a colony looked like because it was obscured from them. That's the whole point. It would do it far away. So not bad. And so he said, if I can reflect this back to you, you'll have to choose between the policy and your conscience. And there is something profoundly alarming about the exact opposite of that strategy being put into play. And it working. Like we went from virtue signaling to like, the cruelty is the point or the corruption is the point, and it's not as repugnant as you would hope it would be.
Jordan Klepper
Exactly. I think we've reached that point where if we can't give you success and joy, we can show somebody has it worse, they will pay.
Ryan Holiday
Yeah.
Jordan Klepper
And that seems to be the thing that excites nonviolence is going to be becoming the one difference, many differences. One of the differences between the 60s is those images were being shot out on three channels and now they're being shot out on a thousand devices and being warped in all these different ways. So it's like, how does that message get out? How do you distill it to just one image? Is, and you are right, like, if suddenly the images of cruelty is not enough to like sicken us, then what. What are the images that could change our point of view?
Ryan Holiday
Or.
Jordan Klepper
Or is this more reflective of what this nation actually wants?
Stephen
Well, yeah, and maybe this goes back
Ryan Holiday
to what we're talking about with the monoculture.
Stephen
So if, if this, the same unfiltered image is getting out to everyone, it. There is this sort of shared revulsion. But if part of the population is getting the revolting thing and then the other part of the population is getting it filtered or edited or flipped on its head in some way, you're not getting the shared consensus.
Jordan Klepper
I really don't know how you find that shared consensus. I do think J6 was such a. It was the most. Well, you were there, right? I was there. I was there. I was hanging out, working. I was working. But that was such. That was the most, most documented crime of all time in human history. We've never seen a crime from so many different angles. And I remember J6, but I remember going and talking to people after J6 and there was that little dip of like shared consensus of a reality and of a story. It's almost mind boggling to watch members on the House and Senate floor the day after on January 7th talk about it. Lindsey Graham and all of these Republican senators. We're very much sharing a reality of this is not who we are. What we saw was terrible. We were running for our lives. This can't stand. Let's move forward. There was that little moment. All right, we all saw that. Of course, we all saw that. And then two months later, three months later, going to events again and just seeing how without even a consistent narrative of what was different about what happened, people couldn't decide if, like it didn't happen, if it was low key. People couldn't decide if it did happen. But it was all FBI agents. It was antifa. Some people were telling me it was isis. There was not a coherent narrative. There still isn't a coherent narrative as to what didn't happen on January 6th. But there was such a need to divert from the shared consensus that we got there so quickly and now we live in it. Now we're. They're political heroes.
Stephen
It's kind of amazing. Yeah. In those early days afterwards where you saw the workshopping of ways to excuse it or whatever, and how in the moment with the memory being fresh, it was preposterous and obviously untrue and transparent. I don't think as cynical as I can sometimes be, if you told me, hey, flash forward five years, actually many people, if not most people, will have absorbed one or more of those ideas as a way of not having to carry the weight of what they obviously saw and what it meant. And if it wasn't so important and tragic, it would really be a pretty incredible case study in how cognitive dissonance works and how sort of propaganda and conspiracy theories sort of use that human tendency to accomplish what they want to accomplish. I don't know if you've seen a
Ryan Holiday
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Stephen
a lot of old wood stuff.
Ryan Holiday
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Jordan Klepper
I interviewed a guy who wrote a book. He drove down from, I forget where, but maybe, maybe Pennsylvania, down to Washington, D.C. day of January 6th, met up with some people, tailgated, shotgunned some bears, went to the Capitol, got with some guys, fought with cops. There's video he punched a cop in the face. And then he goes inside, climbs inside a window, goes inside, the Capitol, gets arrested. They have all the video of punching of the cop, all this kind of stuff. He goes in, he pleads guilty, spends time in prison, has prison tattoos of the Capitol on it. He showed it to me all. And this is a man who drove to January 6, punched a cop in the face, pled guilty. And when I asked him who did January 6, he was like, antifa. And I was like, you did January 6th. You did. You drove there, you punched that cop. You stood up in front court and you said, I am guilty. And then when I press you, you're like, well, I was coerced to do this, or what? Like, he's, he had an ego that wouldn't allow him to say, like, I was completely manipulated. Like, he acted of his own volition to do all these things and would tell you to your face that of course he did.
Ryan Holiday
Right?
Jordan Klepper
But still, in his own head, he can't even comprehend that he was pulled into the mob to do these things, making all of these decisions. And I couldn't get past, like, this was an action that you took very openly and repeatedly. You copped to this being an action. There's videos of it. That's why it was so. It's why you were so clearly guilty and admitted to it all. And yet you can't even sit with the uncomfortable reality that you found yourself here and therefore reach for whatever conspiracy that gives you a chance to move on with your life.
Stephen
Well, and that's where the modeling from leaders is so important because, yeah, there is a performative element and most of our politicians are hypocritical in some way or another and sometimes actually really shitty people. But there is, like, there is the ideal that, hey, I take responsibility for my actions or I try to be consistent in some way or. But when you have the most powerful person in the world sort of reveling in contradiction and hypocrisy and never owning what they say or do. I think that's where it trickles down. And I'm actually, I'm not that worried about like what the president is gonna do to me. I'm worried about what people who are cosplaying as the president's, as a guy like the president, what they're gonna do. Because like for most of us, given the American system, the president doesn't have that much day to day power over individuals. But the county sheriff does and the local prosecutor does and the governor does.
Ryan Holiday
You know what I mean?
Stephen
And that's where like going back to the ancients, like the founders knew these sort of monstrous characters from history, Catilines and various demagogues and they sort of held them up as these cautionary tales and then they held up these other characters that they were like. George Washington is cosplaying his whole life as this probably fictional Roman named Cincinnatus. Do you know about Cincinnatus?
Jordan Klepper
No.
Stephen
So Cincinnatus is the movie Gladiator is also based on this. Cincinnatus is made dictator of Rome. When Rome is about to be defeated, he defeats the enemy and then 17 days later resigns as dictator. So he could have become a Roman king and he doesn't. And so when Washington resigns his commission from the Continental Congress, he's cosplaying as Cincinnatus. And then when he walks away after two terms as president, he's doing it again. Washington is not a perfect player. He is a tyrannical man in the sense that he owns these human beings who he puts out newspaper ads for and whips and things. But he is cosplaying as this character of like what a leader is supposed to do. And we get closer to it and better at it as we go. But I think what happens when you go from cosplaying virtue to cosplaying like mob boss, it gets real bad real quick.
Jordan Klepper
I think that is it in a nutshell right there. Yeah. There doesn't seem to be the large question I think we're asking, like, is there a thirst for the cosplaying virtue anymore? I still think there is. I hope there is. I really hope there is. I think when you're looking for other potential candidates or people on the horizon who speak to that. But there's such an American thirst to follow this person who is this, this mob boss. Although I wonder how much of Americans seeing this, this tough guy pretending to be even tougher than he is. How much of that is them enjoying the mob boss. And how much of that is enjoying just the fame of somebody like that? I think like the success of Donald Trump is in his. Part of his success is just him being famous and a part of people's life as this idea of success for so long that they will follow any choice that he makes, less because of the choice that he makes and more because he is just this epitome of what success looks like from a middle class perspective. Looking at the rich guy in New York.
Stephen
The hope is that it's a singular thing and no, that it's not replaceable. No one else could inherit that because
Ryan Holiday
it's such a historical.
Stephen
But if we're a media fluke, if
Jordan Klepper
we're cynical about it, and I feel like going back to the media literacy, the McLuhan, the medium is the message. I think all of that. What I worry about is virtue doesn't play on these very well a little bit, but it obviously pulls us towards our worst instincts. There's no spaces for the conversations to sort of elevate beyond that in these places. You can do it in literature, but that feels like the. The current events conversation is only happening on these. These short form spaces.
Stephen
Yeah.
Jordan Klepper
That's where I worry. I'm like, cruelty travels, anger travels. Charlie Kirk traveled and became popular in his life because he had beat down videos of the ways in which he. He shamed other people or said outrageous things about black pilots. Like, these things travel. These are the things that like, college kids see as, like, how do I find success? Well, I become an influencer. How do I become an influencer? I say things like this, like. Like, where are those virtuous influencers?
Stephen
Well, though I had. I interviewed Terry Virts, who's running for Senate in Texas. He's an astronaut. And I was like, my kids don't want to be astronauts. They want to be YouTubers. You know, how do we get back to there? Like, that used to be the highest, noblest, coolest thing you could do.
Jordan Klepper
Yeah.
Stephen
Like, the only thing my kids are impressed by is that YouTube plaque that I. They don't give a shit about any of my other things. Yeah. And when their friends come, they're like, oh, my God, is that right? They're like, because it's the only part
Ryan Holiday
of my world that.
Stephen
That intersects and has currency in their world, you know?
Jordan Klepper
You know, what was. I don't think I talked to you about this. What was the last special I did was looking at sort of this new Right Maga movement, and I talked to like Hasan Piker. I went to a Turning Points event and was talking to a lot of like 18 to 22 year olds and the conversation got into their algorithmic feeds, TikTok and what TikTok is feeding them. We talked a lot about how like men are being feedback. You need like Andrew Tate videos kind of pulled into this uber masculinity world. There was even, I think it was an Australian study that kind of talked about if you started neutral on these algorithms within like 12 minutes, they would get pulled into these Jordan Peterson video and you are. You're all that.
Stephen
That's going to be the best one that you saw.
Jordan Klepper
Yes, exactly. It's dark, but there's a little William F. Buckley vibe in there that maybe isn't quite as hateful as some of these other ones. But they was also pulling to your videos. It talked about Ryan Holiday videos.
Ryan Holiday
Really?
Jordan Klepper
Yes. And so they studied in the Australian study, talked about the things that it pulled towards were these. It was talking mostly about like men, what they came to. And I thought that was fascinating and exciting. I immediately distanced myself from you. I was like, I don't know who this guy is, this Andy.
Stephen
That's one of the reasons I make this stuff is that I like, I would love young men to be like, all I do is read books. That's what I did when I was 20. But that's not representative. They're mostly consuming stuff on social media and on YouTube and podcasts. And so the. I think one of the big problems is that responsible, decent, productive sort of voices have just seeded that field. Like they, they took self by, by looking down their nose at self help and sports and these other things and comedy. They just ceded it to people who don't have any, not, not all of them, but to a lot of them. They, they just ceded it to people who don't share the same notions of responsibility or morality or whatever.
Jordan Klepper
Yeah, I think I, I talked to Hasan Piker out there and it was really curious seeing the fan base he has. He's very political, but he. Outside of the traditional left norm, he's. He posts workout videos and all of these like typically masculine videos, sports videos like that, interesting just fashion videos and so many people on the left don't know what to do with that. But he articulated. I don't want to misuse his words, but in a sense just sort of how like these are younger people who want to learn more about the world feel. He said something that resonates. They feel like they can't change the world because it's so chaotic and moving on without them. It's not going to give them a house, not going to give them a job. So the least they can do is change themselves and better themselves. And they're looking for answers there. And so if that sense makes, Means working out and physically getting better, it's diet, I think it's philosophy and finding ways in which like oh, stoicism can actually give you space for that. I thought that was, I think you're right. A lot of people seceded that space in that lane on these, these mediums where it actually is the stuff that does seem to get through. And when I talked to a lot of those 18 year olds, I saw that. I didn't see the cruelty that I assumed I would see, but I see the older people at these rallies. I saw a lot of people who are looking for ways in which to, to shape their life, understand the world, get some power within it, but also to figure things out. And that like, thirst for curiosity that did give me a little bit of hope and see that it is heading in these, these directions.
Stephen
Well, I, I saw this interview with Ruben Gallego and is that his name? The senator and he was saying that the male constituents, he's like, they want
Ryan Holiday
a big ass truck.
Stephen
He's like, that's what they want. He's like, you're not gonna get elected telling them that having a big ass truck is dumb, you know, and it's not dumb if that's what they want. Like that's what they want, right? I have a truck, I like it.
Jordan Klepper
It's big ass.
Stephen
Is it big ass? I wouldn't describe it as a big ass truck, but I like it because it has leg room and I can fit my car seats in it. Do you know what I like? You gotta work on that branding.
Jordan Klepper
Call it a big ass truck if you want those clicks.
Stephen
It's a regular car. Here's the funny thing. A Ford F150 and a Chevy Silverado are the number one and the number two bestselling car in the country. So it's. You're not the normal one by thinking they're dumb.
Ryan Holiday
You know what I mean?
Stephen
Like that's the normal thing. And so what do people like, what do they want? And how do you meet them where they are? A politician's job is not to tell you that your truck is dumb. You know, it's to solve some of your problems, right? And so there was this kind of snootiness and condescension, like I Remember when my books first started working, there was some article, I'll never forget the headline. It was like, ancient philosophy for designed for Greek slaves, popular with Silicon Valley. And it was like, it was saying that it was so dumb that these people were interested in. And it's like, okay, first off, that's a preposterous misreading of the philosophy. But second, tech bros reading about ancient philosophy is a good thing. You know, you're making them feel stupid for liking this. And so they're either gonna go like, something worse to spite you, or they're just not gonna see the other things that you think are important as important. And so there was, I think, a driving away of people into these different communities. And now you want them back and they're not gonna come back. Like, when I was in college, we watched the Daily show and we watched south park and we thought Republicans were dumb because they wanted to tell us what we could do. And somehow they managed to flip that.
Ryan Holiday
That.
Stephen
They managed to flip that by making fun of the other things that a normal average dude would be into. Yeah, it's really bad.
Jordan Klepper
Democrats, if you're out there, talk about the trucks. People like trucks. They like truck nuts. Yeah, don't be negative. I'm still going to make jokes about truck nuts. But. But understand, there's a desire out there, I do think that is oft forgotten and how it is also connected to, like, people wanting to feel a sense of control, wanting to feel a sense of like, a path towards betterment. There's very few paths towards, like, intellectual curiosity for young men. Again, I feel like such a. Sometimes in the, in the New York bubble, you know, people have questions. How do, like, at least a couple years ago, there was such a question about, like, this desire, like why young men were listening to so much Rogan or Manosphere podcast kind of stuff. And, you know, I was talking to this really interesting guy who was a bartender and he was paying for a podcast that gave him unbiased look on the left and the right and presented things that way. And I was like, you pay for this podcast. He's like, I totally pay for this podcast. He's like, I'm tired of all of the noise. I want these things too. And he also listened to Rogan all the time. When I talked to him, I was like, well, what draws you to Rogan? He's just like, he's a guy who works at a bar, shows up early, has to set up the bar for a couple hours. He's just like, I'm just. I like that he's interesting people on this week he had an expert on bees on and I thought it was fascinating. Just like right. There's so many people out there who desperately curious and it's just a desert of interesting things that are out there and finding people who can point them towards curious thinkers, things that expand their mindset beyond what a normal 22 year old might think about. It's very exciting to most people. And there's very few on ramps for something like that.
Stephen
Yeah, no, no, you have to, you have to meet people where they are and bring, bring them in.
Jordan Klepper
Yeah. And then tell them books. Then sell them books.
Stephen
Right. That's why I was always. It's like I'm selling them books. This is. We're on the same team here.
Jordan Klepper
Guys, guys, let's not get mad at them for the books.
Stephen
Yeah, this is good.
Jordan Klepper
This is a good thing. For God's sake. They're reading, they're reflecting, they're sitting in their thoughts. It's a nice thing.
Stephen
You want to go check out some books?
Jordan Klepper
I would love to check out some books.
Stephen
Let's do it. Thanks so much for listening. If you could rate this podcast and leave a review on itunes, that would mean so much to us and it would really help the show. We appreciate it and I'll see you next episode.
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Ryan Holiday
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Date: March 6, 2026
Host: Ryan Holiday
Guest: Jordan Klepper (comedian, Daily Show correspondent)
In this rich, engaging episode, Ryan Holiday and Jordan Klepper dive deep into the modern challenges of “mob thinking,” how cultural discourse is shaped by leaders and media, the delicate balance between free speech and social responsibility, and what the erosion of shared norms means for American society. Klepper draws on his extensive on-the-ground experience covering political events, including January 6th, and offers sharp, often humorous, insights into why people behave as they do within group dynamics—and what role stoic virtues might have in response.
Klepper on Normalizing the Taboo:
Klepper recounts how, in 2015, certain conspiracy theories (like “birtherism”) were seen as taboo but became normalized when high-profile leaders (Trump) began speaking openly about them.
“I don’t think he changed that many people’s minds, but I do think he completely changed the discourse of what was acceptable.”
(Jordan Klepper, 09:23)
Mob Mentality in Real Time:
He observes a transition from private belief to group rhetoric:
“When you’re a group of people who are all talking about this thing and such a powerful, famous person tells you this thing, you go along with this thing... That is that mob mentality.”
(Jordan Klepper, 10:08)
Power and Integrity:
The conversation acknowledges backlash against “political correctness,” but Klepper argues leaders should model responsibility:
“It’s an argument for integrity for people in positions of power... I think there’s another pocket of people... who are just trying to be a part of the conversation and are catching up. Apparently, this is the thing that people are talking about now.”
(Jordan Klepper, 10:59)
Performance and Standards:
Critiquing the past and present, Klepper remarks on the “performance” of virtue:
“We’ve always believed in this idea of better angels that we can ascribe to something more. That was, at the very least, an empty performance, but it was still a necessary performance.”
(Jordan Klepper, 12:49)
Edgelord Politics:
“That baseline responsibility has been replaced with... edgelord politics... Success in being, in nagging, being outrageous, crossing that line. It’s always funny because comedy gets looped into this about what can you say... But more often than not, the people I know... have that baseline responsibility and choose to step over the line tactically... Those who don’t understand the baseline responsibility... are removing something that is not a creative choice but more of a basic human quality... all adults should be expected to have.”
(Jordan Klepper, 14:13–15:18)
First Amendment vs. Social Consequence:
Holiday and Klepper agree that while abhorrent things should be legal to say, society should still label them as such:
“It should definitely be legal, but you fucking suck if you say certain things... there should be social consequences for saying and doing shitty, but not outright illegal, things.”
(Stephen, 15:18)
Klepper responds:
“100%. We should still have a basic morality... There can be... consequences for that.”
(Jordan Klepper, 16:12)
Conflation of Cultural and Government Action:
“We have so little both understanding publicly and respect for what government does... The fact that, like, the Trump administration is weighing in, leaning on the FCC and doing all these things... We’re not talking about what culturally we’re doing. We’re talking about what an elected government is now imposing, but we’re all just lost in this mix of conversation.”
(Jordan Klepper, 16:52)
“The Cruelty is the Point”:
Klepper and Stephen discuss how performative cruelty, endorsed by those in power, has become a cultural rallying point:
“The Dana White of it all is it’s there to piss people off. It’s edgelord politics. And I don’t think mom and pop in the middle of America give a shit about that. But in the last two years, this seems to be what the competition is.... Actions are so amoral and edgelord in a way...”
(Jordan Klepper, 20:46)
He later references Adam Serwer’s “the cruelty is the point”:
“That Adam Serwer article—the cruelty is the point—I think that is such a big part of it. It’s not all of it, but it’s such a big part.”
(Jordan Klepper, 23:44)
Media Savvy and Virtue Signaling:
Holiday notes that past civil rights movements used media to shock Americans’ conscience, but now “the opposite of that strategy” is in play, and it works.
“It’s profoundly alarming that... we went from virtue signaling to the cruelty is the point or the corruption is the point, and it’s not as repugnant as you would hope it would be.”
(Stephen, 25:14)
Loss of Shared Consensus:
Klepper notes that even with the most documented crime in history (January 6th), consensus broke down quickly:
“There was that little moment we all saw that... And then two months later... people couldn't decide if it didn't happen... or if it was all FBI agents... There was not a coherent narrative. There still isn't...”
(Jordan Klepper, 27:37)
Cognitive Dissonance in Individuals:
He shares an interview with a J6 participant who, despite having literally pled guilty for his actions, clings to the “antifa did it” narrative:
“This is a man... who drove to January 6, punched a cop in the face, pled guilty... and when I asked him who did January 6, he was like, antifa. I was like, you did January 6th...he can't even sit with the uncomfortable reality...”
(Jordan Klepper, 31:49–32:57)
Modeling Responsibility:
Concern about leaders who revel in contradiction and never accept responsibility, trickling down attitudes to the public.
“When you have the most powerful person... never owning what they say or do... that's where it trickles down... what people who are cosplaying as... the president... what they're gonna do.”
(Stephen, 33:29–34:35)
Historical Role Models vs. Mob Bosses:
Holiday contrasts George Washington’s modeled virtue with today’s leaders:
“Washington is cosplaying... what a leader is supposed to do. But what happens when you go from cosplaying virtue to cosplaying mob boss? It gets real bad real quick.”
(Stephen, 35:00–36:01)
Fame and Authority:
Klepper suggests Trump’s success is less about ideology than about fame and the cultural valorization of unvarnished success:
“He is just this epitome of what success looks like from a middle class perspective. Looking at the rich guy in New York...”
(Jordan Klepper, 36:59)
Algorithmic Drift:
Klepper and Holiday discuss how social media algorithms rapidly pull young men into ideological echo chambers.
“If you started neutral on these algorithms, within like 12 minutes, [they] would get pulled into... Jordan Peterson, Andrew Tate videos...”
(Jordan Klepper, 39:20)
Stoicism’s Surprising Reach:
“It was also pulling to your [Ryan Holiday’s] videos... I immediately distanced myself from you—I was like, I don't know who this guy is...”
(Jordan Klepper, 39:34)
The Need for Responsible, Accessible Voices:
Holiday laments how decent influences have “ceded the field” to less responsible voices, but both agree that there is a thirst among young men for self-improvement and meaning, despite the negativity and bad incentives of some platforms.
Positive Prospects:
Klepper sees hope in young men seeking philosophical or self-improvement content:
“I didn’t see the cruelty I assumed I would see... I saw a lot of people who are looking for ways in which to... understand the world, get some power within it, but also figure things out... that thirst for curiosity did give me a little bit of hope...”
(Jordan Klepper, 41:12)
Cultural Disconnects:
They discuss how politicians and cultural leaders miss opportunities by condescending to or mocking ordinary interests (e.g., trucks, self-help).
“A politician’s job is not to tell you that your truck is dumb. It’s to solve some of your problems...”
(Stephen, 42:48)
Encouraging Curiosity:
Klepper highlights the importance of channels that expand young people’s minds and expose them to new ideas, seasoned by his own encounters:
“There’s so many people out there who desperately [are] curious and it’s just a desert of interesting things... and finding people who can point them towards curious thinkers, things that expand their mindset...”
(Jordan Klepper, 45:26)
On Leadership and Performance:
“You got to still perform this shit. You got to still pretend like we are better than this, that we can achieve greatness... At the very least, an empty performance, but it was still a necessary performance.”
(Jordan Klepper, 12:49)
On Edgelord Politics:
“Edgelord politics is in of itself, like, more redeemable equality than basic responsibility.”
(Jordan Klepper, 14:13)
On Cultural Accountability:
“You fucking suck if you say certain things... there should be social consequences for saying and doing shitty, but not outright illegal, things.”
(Stephen, 15:18)
On Cruelty as Cultural Currency:
“Wouldn’t this piss these people off? ...the cruelty is the point... they want the images of these ICE raids... in that gosh darn group... this person just froths at the mouth for that cruelty...”
(Jordan Klepper, 23:44)
On Historical Role Models:
“But what happens when you go from cosplaying virtue to cosplaying mob boss? It gets real bad real quick.”
(Stephen, 36:01)
On the Future:
“There’s very few on-ramps for something like that... but that thirst for curiosity did give me a little bit of hope...”
(Jordan Klepper, 41:12 / 45:26)
The tone is candid, urgent, and bracingly honest without despair. Klepper and Holiday, with sharp wit and cultural awareness, peel back the nuances behind mob thinking, social leadership, and modern challenges in civic discourse. Both acknowledge the bleakness of current trends (cruelty, nihilism, fractured reality), but also underline the ongoing human thirst for guidance, curiosity, and virtue—reminding listeners that how we use our voices, platforms, and choices still matters.