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A
This is an Iheart podcast. Run a business and not thinking about podcasting, Think again. More Americans listen to podcasts than ad supported streaming music from Spotify and Pandora. And as the number one podcaster, iHeart's twice as large as the next two combined. Learn how podcasting can help your business. Call 844-844-IHeart.
B
Welcome back to the Carol Markowitz show on iHeartRadio. My guest today is Josh Holmes. Josh is a partner at campbellrey, LLC and co host of the Ruthless po. So nice to have you on, Josh.
C
Oh, it's great. Thank you for having me.
B
I love your show. I love your Twitter feed. I've been a huge fan of yours for many years, and I'm really excited to learn more about you. I don't feel like I know a lot about your background or about how you got into this, you know, thing of ours. So how did it start for you? How'd you get into politics?
C
Well, the feeling is mutual. Obviously. I've been an admirer of your work a lot over the years. Thank you. Yeah, it's a roundabout of getting here for me. I grew up in Minnesota and had, you know, the time of my life, sort of an ideal upbringing in a lot of different ways. But when it was time for college and, like, professional, you know, imaginement at some level, like, what is that you do? I went to Arizona State University. And I wish I could tell you that that was a academic decision.
B
That's a party school, right?
C
Yeah.
B
Well, it wins awards.
C
At the time, at the. At the year that I was going, it was number one.
B
Number one. Wow.
C
And I applied to two schools, Arizona State and the University of Florida. And Arizona State said yes first. And so that's where I went, which is a long way from Minnesota. And it had absolutely nothing to do with what it is that I wanted to or thought I wanted to do for a living, but.
B
Which was what? What were you thinking?
C
I didn't know. I mean, I, you know, like so many young people, you just have no idea of what it is that you're good at, you know, And I, like, I think this is at some point an indictment of education and education systems. At some point, I found nothing that I was super excited about.
B
No. You haven't used the Pythagorean theorem since. Since you learned about it.
C
No. I mean, the last math class I took, Carol, was called Math.
B
Same. I recently learned there's a thing is math dyslexia. And I'm pretty sure I have it.
C
But I mean, so I went down there to basically have a good time. But I also, you know, in the process I had a, a medical procedure. When I was in my second year, I had brain surgery, believe it or not. And you know, I, I was something less than a good student. The first year, year and a half that I was at Arizona State, I was more interested in the social scene, but I had this, this issue where I had, I had brain surgery. And I remember sitting in the hospital bed where all my friends were coming in one after one just to wish me well and try to cheer me up. And I was there for several weeks and they were talking all about what they were doing and all the career advancement or internships, whatever that they were interested in. And I remember at that moment thinking to myself, man, I gotta kind of get this thing together. Like I, I certainly don't want.
B
But you just had brain surgery. Yeah, I feel like if you could take it easy at any point, it might be that moment.
C
Well, I think the problem was that I took it easy for a long time before that and it required a kick in the ass, to be honest with you. It requ a observing that other people were moving on with life after high school and, and you know, early part of college and they were focused on something. And so, you know, I, that was kind of the moment I started focusing a little bit on school. And then what did. I wanted to do?
B
So what did you want to do?
C
I didn't, I still didn't know. I started doing some journalism stuff back then in large part because I grew up in a family that was really big into news, really big into politics, although it wasn't my politics. I mean I, I grew up all the way from Ronald Reagan just being a die hard Republican. Both my parents grew up as Democrats.
B
Wow.
C
And. But I kind of knew where I, I was on all of that. And I thought, well, news and information is pretty powerful and maybe this would be a business that I wanted to go into. But then I spent, you know, the first couple semesters, everybody telling me about the history of news and Edward R. Murrow and everything else. And I was like, no, no, this.
B
Is not for me.
C
Yeah, I was like, yeah, this is probably not the thing. So I got out of it. And you know, both my parents were attorneys and so I thought, you know, maybe pre law, maybe something like that. And they had a program at the time at Arizona State that was like a, it was like a double minor type thing was called interdisciplinary studies, whereas justice studies and political science, it kind of combined that where they could get a lot of people into law school. And I thought that's what I wanted to do at the time.
B
So did you do it?
C
Nope. I sure did.
B
What did you do? Where did you go? Tell us about it.
C
Well, I think what happened to me was my dad convinced me at some level to come out to Washington D.C. and just spend an internship program. And there was this Washington semester program through American University that gives you a little entree into the political world. And obviously, I'm from the middle of Minnesota. I have no idea. I've got no connections. My dad's got no connection. My mom, you know, mom's got no connections. Nothing connected to Washington D.C. but he's like, why don't you just go out and try it? And I did. And I was there for 10 days, and 911 happened.
B
Wow.
C
And that fundamentally changed the trajectory of me and what I wanted to do, and I think the rest is history.
B
So it's interesting that your dad encouraged you to go to D.C. even though you guys were politically opposed. Like, I think about that with my own kids. If my kids end up being libs, am I going to be like, yeah, you go pursue those dreams, you know, you go work for me matters. I don't know. I don't know that I would be so like, you know, I probably wouldn't, like, dissuade them, but I also don't think I'd be like a big cheerleader for it. But your dad was.
C
Yeah, well, I mean, his politics were changing too. You know, I think. I think my parents had a fundamental realignment after 9 11, which coincided with me. My brother worked in Lower Manhattan, and I was at this point an intern in D.C. and if you remember, 9 11, nobody could get a hold of anybody. And so it just fundamentally realigned their point of view. But from a personal experience, it was realigned what I wanted to do and where I thought I could make a difference in what I was interested in. And I just really dug in at that point. And, you know, everybody's got a different pathway, but when you see something that is. Gives you energy that you think you're good at, that you think you can provide value for you charge forward even as a young person. And I never would have imagined that all of that would have led to, you know, my experiences over the last 20 years, but it did.
B
So how did you guys get into Cavalry? What. What was the impetus for that?
C
Well, it's a longer story in a little bit in that I got into politics. I Did it the first time I was in the United States Senate, I couldn't figure out why it was that everyone spent so much time talking about things that were never going to happen.
B
You know, welcome to government.
C
Yeah. And it just, it frustrated me. And you get that. You know, I'm sure your listeners all can identify with this. You get this component somewhere between when you get into the workforce in your late 20s, where you look at things and you're like, well, I can do the job better than the person who's like, supposed to be managing me, but I'm not recognized as such. And there's a frustration involved in all of that. And so I kind of switched things up and I wanted to go into communications. I was in policy and I met Ken Melman, who was then 2004 presidential campaign manager for George W. Bush, who brought me into the RNC at the time. We had a historically bad election in 2006, but I met a whole bunch of people who were just really good people, thoughtful people, and had hilarious dark.
B
Humor about it, which is really important, actually.
C
Yeah. I mean, they could make the worst time not feel like work. And I was attracted to the whole situation. And Melman at some point introduced me to McConnell, who was just becoming leader, was elected in the fall of 2006, and. And McConnell said to Melman, I. I gotta revamp all Republican communications at some level. I mean, if you went into like the Republican conference in the Senate at that time, they were doing like these weird tape, like pre tape things that look like they. I mean, I remember walking into one, it was Ted Stevens, and they had this whole bumper music that was like, today we bring you the Ted Stevens show. And then he would talk about the most boring shit on the face of the planet.
B
Yeah.
C
And. And then they would just take it and ship it back to Alaska. And I was like, this is like, we're in a different time. The Internet is like a real thing at this point. And so. And McConnell recognized that too. And so he asked me to come in and help run this new communications unit that he was using. And my promise to him was that I would be there for six months or so to make sure that they got up and running. And then I was going to go do a presidential campaign or something like that. And I remember there was a couple of moments in there that I was like, wow, this guy doesn't. He's not talking about anything that's not going to happen. He only talks about what is going to happen. And it was a. A fundamental, fundamental Reversal from where my whole point of view, Senate and government was.
B
So what was the next step? What happened then?
C
So we got, you know, look, there's a ton of war stories with, I would go out and do campaigns, then I'd come back to the Senate and go out and do campaigns, come back to the Senate. But there was a synthesis there where I got to work with really good people. And I think if there's one fundamental takeaway from my career at that stage was when you get good, decent people who are doing things for the right reasons that you understand and you jibe with and you can create and do things bigger than you can do individually, you don't want to lose that. You want to make that a central part of what you're doing. And so all of that ran up until 2014, where, you know, I'd worked with John Ashbrook who was a co host of, of Ruthless. And I always felt like if the two of us are in a room, we can figure out any problem.
B
Yeah.
C
No matter how bad it is. And there was a number of other people that were involved in all of that. And so we started a company after we got out of government service called Cavalry, where we tried to basically take what it is that we learned over the last seven, eight years of government and politics and advocacy and everything else to try to bring it to a larger marketplace that was, I mean, largely operating on a 1980s footprint. Right. It was like if you read Gucci Gulch of like shoe leather lobbying. That's basically where things were in the early 2010s and the world had changed, changed. And so we wanted to get involved in it.
B
We're going to take a quick break and be right back on the Carol Markowitz Show.
D
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A
Run a business and not thinking about podcasting, think again. More Americans listen to podcasts than ad supported streaming music from Spotify and Pandora. And as the number one podcaster, iHeart's twice as large as the next two combined. So whatever your customers listen to, they'll hear your message. Plus, only iHeart can extend your message to audiences across broadcast radio. Think podcasting can help your business. Think iHeart streaming radio and podcasting. Call 844-844-IHeart to get started. That's 844-844-IHEART.
B
How did Ruthless start?
C
That was a funnier story. So Johnny and I at that point had worked together, and Duncan and I had worked together since 2014, since that great campaign cycle we had. And so we were watching the change in media. And it used to be that you would hire a PR agency or do whatever you can to fight like hell to get the quote that tried to refute the premise of a mainstream news studio at some point in, like, the 16th paragraph. And that was, like, considered to be a win. But we were watching audiences change, and at some level, audiences were becoming larger than the mainstream media outlets themselves. And so we, we put a lot of thought into it. Meanwhile, we were huge fans of Smug.
B
Comfortably Smug, my favorite liberal friend.
C
Yeah, exactly right. So on X, his sense of humor is irrever. Sense of humor. His engagement or whatever in the early days of X, like, blocked out the sun.
B
I mean, he was everything.
C
He was everything. And one day he asked all of us to go have a happy hour with him out of nowhere. We'd never met him, and I was like, I gotta see what this guy looks like. Like, I have no, I have no clue. He's an anonymous figure. And we went and had the time of our lives. And at the end of it, Smug says to me, hey, I got an idea. Do you mind if I come by the office in the next couple weeks?
B
It was Smug's idea, huh?
C
Well, here's the funny part of the story. He comes into the office and he's got this memo that outlines what it would be like to have a media company and a podcast that basically uses humor in large part to sort of Skewer and make commentary on what's happening with, like, a leftist media and leftist narratives and whatever. At the same time, we had worked out on one ourselves and presented him with a PowerPoint. It was literally the same idea.
B
Wow.
C
It was literally the same idea. And so at that point, like, we knew we had to do something. And then it Covid hits, and we're all sitting at home because nobody in DC wouldn't allow you to come into dc, Right. And we started this happy hour zoom call where we would have a bourbon at the end of the day, talk about whatever, bet on some horses, because that was, like, the only thing that was still going. They're like, sports shutting down, gambling.
B
That's crazy. But if you remember, like, of course, but not gambling.
C
Sports were largely canceled, which is what we all do.
B
And so horse racing was, like, in baseball, right?
C
Yeah, like, horse racing was it. And so, you know, we bet on some ponies and. And talk, and we were like, no, this is a good cadence. Like, maybe we should figure out how to format this. And when we launched Ruthless, it was like a. A real flyer. Like, I don't think any of us thought it was going to be the thing. I thought, you know, we thought it was a 1.0 version to try to test the marketplace because not. None of us knew anything about podcasting.
B
Yeah.
C
In fact, like, Duncan and Ashbrook were, like, teaching themselves how to edit audio and get it online. But our third episode, I think, was. Went to number one on the political charts. And we thought at that point, well, I think we got an obligation to try to do this. And it was a weird period of time. It was the end of 2020. It was between, you know, the 2020 election in January 6th, where we were trying to figure out how to get a foothold in conservative politics.
B
Right.
C
It was. It was tough, and we were very conflicted about a whole bunch of it. But once we emerged from that, we realized that the real conversation we were having is the conversation everybody else is having at the bar.
B
Right. And I think what you guys do so well, and if I could just give you some compliments, I think you're so honest. Like, I don't think any of you are fronting anything. And there's a lot of, you know, this movement in the conservative world, this changes all the time, but you guys are who you are. And, you know, I got my jokes about smug, but I. I always thought that about him, that he is who he is, and he is not trying to pretend to be anything else.
C
Yeah. I mean, I think that's a, a fair assessment. I mean, for Smug and, and the other three, Duncan Ashbrook and I, it, it's not worth doing.
B
Yeah.
C
If you have to come up with some version of yourself, that is not what it is.
B
You're not, you're not adjusting to anything is what I mean. Like, you know, you do see in the conservative, you know, things change very rapidly and what was cool a year ago might not be cool today. And I don't think that you guys are like seeking out the next thing. You're not catering to what the next thing might be or, or trying to find an audience, a newer audience or anything like that.
C
Yeah, no, I mean, because we didn't have to do it. It was a luxury. I understand the people who do have to do it, this is all they do for a living. And you know, you, you want to stay a step ahead of where the electorate is. But yeah, you know, we had, you know, two advantages in that regard. One is that our job was to stay ahead of the electorate in a lot of different ways over the previous 15 years. And the second piece of it was we don't need to do this.
B
Right? That's it.
C
If it's not fun and it's not, we can't laugh, pack up and go do something else.
B
That's what makes it so good. I really, I really believe that we're going to take a quick break and be right back on the Carol Markowitz Show.
D
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A
Run a business and not thinking about podcasting, Think again. More Americans listen to podcasts than ad supported streaming music from Spotify and Pandora. And as the number one podcaster, iHeart's twice as large as the next two combined. So whatever your customers listen to, they'll hear your message. Plus, only iHeart can extend your message to audiences across broadcast radio. Think podcasting can help your business? Think iHeart streaming radio and podcasting. Call 844-844 iHeart to get started. That's 844-844, iHeart.
B
Switching gears. What do you worry about?
C
Look, I worry about where the information flow is in this country. I encounter so many people and you can see this play out live on cable news every day that exclusively subscribe to one information flow cylinder rather than another. And it's always a self rewarding choice. Right. Where it's like they've got previous convictions about something, anything that sort of fills that cylinder, their exclusive view of the world. And you know, in the, in the era of the Internet and podcasts and all these other things, it concerns me now the, the upside of the era that we're in is that you have a choice other than cbs, ABC and NBC. Right. To give you the true story of what's happening. I think we found out over the last eight years or so. They're not.
B
Yeah. They're a bunch of liars.
C
Yes. They're not equipped to do that. Which, which is fine. But I do, I do concern myself a little bit with people self radicalizing.
B
Yeah.
C
And it's, it's not just, you know, this isn't a right or center or a left of center thing. It's about your choice of trying to be intellectually curious and understand your neighbor.
B
Right.
C
And, and I think too often your choices of what you consume in news and information affects your interaction with your neighbor. I hate that.
B
Yeah.
C
I have a really good friend who works on Capitol Hill who was just telling me on Sunday that they moved into a new house next to somebody and they went up, you know, like at the basket of muffins or something, as one does.
B
Sure.
C
It was like, you know, I'm your new neighbor, you know, just wanted to get to know you. And this person. Basically their response was, we've googled you, we know who you are, we've seen your, your ex account. We know what you do. We're not Interested in a relationship.
B
Wow, that is.
C
And you know, it's a. You're talking about somebody who's a staffer on the Republican side and somebody who's obviously a do liberal. And I worry about that because I just think like the shared experience in the United States has always been part of our story. Empathy, understanding and persuasion. And if you don't have that in some combination, I worry a lot about where that goes from.
B
Yeah, I understand people siloing a little bit. Like, look, I moved to Florida, I wanted to be in a red state. I had never lived any where anybody agreed with me before. So I get the wanting to be in a little bit of a bubble. But, you know, if a liberal moves next door to me, then a liberal moves next door to me. It's not, you know, it's not like I can't possibly be friends with you. And I think that, yeah, it is really sad that that's where we've gotten. I think that, you know, I don't want to just blame the left, but I feel like this happens way more from the left than it does.
C
It's much more intolerant.
B
Yeah.
C
No question about it. I mean, look, I, all my conservative friends, this doesn't enter their lexicon. Like whether I can talk to somebody or not talk to somebody doesn't revolve around whether they're a liberal or a conservative.
B
But your, your friends a smug. So.
C
Exactly, exactly. He's going to love this. He's going to love this.
B
This is what it's all about, actually.
C
But I mean, that is increasingly. It started with Cancel Culture and It started with MeToo movement and all these other pieces of what has become of the left where they're just willing to just cut off like they don't exist, anybody that doesn't agree with them. And I think that's dangerous.
B
Very. Yeah. Because you don't know, it could be, it could be your kids again. You know, I think about stuff like that all the time. And the fact that people cut off each other over politics, especially family, like, don't do that, guys. Just don't do it dumb. So looking back on your life and career, what advice would you give your 16 year old self? Do you still go to the party school?
C
I do, absolutely.
B
Yeah. Like the parties were fun.
C
Unquestionably. Look, I think everybody's different and this is, I think, you know, when I hear people much more successful than I am try to give standard advice on a question like that, too often it's, it's, it, it subscribes to an idea that we're all the same at every point in our life and we're not. I mean I was 16, I was a reckless, crazy party kid. I needed a little bit of guidance, but more than anything I needed something productive to be inspired by. I went through a long period of time there where I just wasn't. I didn't know what I wanted to do, but it landed on me at some point. I mentioned the 911 thing and it just, it created all the energy that I used to be unproductive. I understood that I now wanted to do something to be productive. But there are other kids who, you know, they're studying all day and night in high school and they want to go. Do.
B
Not me, but kids, I, you know.
C
Yeah, but they want it. You know what I mean? You've met these people. Some of them are very, very successful where they just, they're very focused on we have to do xyz. I need to get into Ivy League school and do all these other things for those people, I would say go have fun.
B
Yeah.
C
Like go. Unless you understand the full panoply of life and what it has to offer, at some point in life you're going to be resentful of what you didn't do unless you checked it all out. And you know, you hear a lot about midlife crisis and, and all these other things. Like it's visit you when you're just monocularly focused on one thing that you need to be this one person and at some point it's not authentic. So you got to find your authentic self. I will say the second piece of it is prepare. When you're a young person to go through a decade of your twenties if you want to be successful of just grinding just.
B
Do they 20 year olds still do that? I feel like no.
C
Maybe not, but it's going to be a problem for them. I mean, no, I think some do. I think there are a lot of people who do. But what's most important is that you understand that the work that you put into setting the infrastructure for who you become both in terms of what you're able to do and who you are as a person is so important to not be the 38 year old, 45 year old, 50 year old who is resentful, angry and counterproductive and is basically going to work every morning just to pay the bills and get through the day. Right, Right. I mean that's where you set the bar, you're building all those things. If you're demonstrated value between 22 and 35 is such that everybody sort of recognizes what it is that you do when you're 38.
B
That'S where you want to be.
C
It's easier. It's easier. And then your authenticity as a person can come through. And you learn a lot about yourself in those days, because it's not easy.
D
No.
B
Yeah. I love that. I've loved this conversation. I've loved getting to know you. I think that everything you do is awesome, and I love to follow your career and wish you all possible success. Leave us here. You gave us some good advice, but leave us here with your best tip for my listeners on how they can improve their lives. And maybe it is the live authentically and pursue your passions.
C
Yeah, I think that's a big part of it. More importantly is do not disregard the people you surround yourself with. Make sure that those people are people who lift you up. You're not. You're not associating with them because you think you can get something out of them or. Right. I mean, these are like true blue. Go to war with. Have a great time with people who are just. They're there with you. You can go so far out on the limb, if you look back and you know everybody's got you. Like, they're. They're going to be there for you whether it goes good or whether it goes horribly. Like, these are. These are people who can support you, and once you do that, you're willing to take risks. Not all of them are going to go well, but, I mean, some of them do, and that's going to ultimately define your professional life in one form or fashion.
D
I love that.
B
And if you haven't found those people, keep looking. Think, don't settle. Yep, he is Josh Holmes. Check him out on the Ruthless podcast. Thank you so much, Josh.
C
Thank you, Carol.
A
This is an I Heart podcast.
Podcast: The Clay Travis and Buck Sexton Show (iHeartPodcasts)
Host: Karol Markowicz
Guest: Josh Holmes (Partner at Cavalry, LLC, and Co-host of the Ruthless Podcast)
Date: October 1, 2025
This episode features an in-depth conversation between Karol Markowicz and Josh Holmes, diving into Josh’s unconventional path to politics, his views on the state of American media, and the origin story—and ethos—behind the popular "Ruthless" podcast. The discussion covers personal anecdotes, career pivots, skepticism about the current information ecosystem, and authentic self-expression, peppered with humor and candid moments.
Early Life and Education
Finding His Direction
On personal turning points:
“It required a kick in the ass, to be honest with you.” – Josh Holmes, 03:43
On political communications:
“They were doing like these weird tape, like pre tape things that look like they… just ship it back to Alaska. I was like, we’re in a different time.” – Josh Holmes, 10:29
On the Ruthless podcast’s origins:
“It was literally the same idea.” – Josh Holmes, 17:20
“If it’s not fun and… we can’t laugh, pack up and go do something else.” – Josh Holmes, 20:51
On polarization in America:
“I worry about where the information flow is in this country.” – Josh Holmes, 23:07
“We’ve googled you, we know who you are… We’re not interested in a relationship.” – Josh Holmes, 25:04
“It started with cancel culture… they’re just willing to just cut off anybody that doesn’t agree with them.” – Josh Holmes, 26:58
On authenticity and ambition:
“Find your authentic self… but also prepare…to go through a decade of your twenties just grinding.” – Josh Holmes, 29:10
“Do not disregard the people you surround yourself with… these are people who can support you, and once you do that, you’re willing to take risks.” – Josh Holmes, 31:38
The conversation is candid, friendly, and laced with both humor and hard-earned wisdom. Josh Holmes combines self-deprecation with insight, while Karol Markowicz keeps the conversation relatable, often inserting her own observations and lighthearted asides.
This episode offers a rich insider look at the evolution of conservative media and advocacy, the personal journey of a political strategist, and the challenges facing American society in an era of intense tribalism and media fragmentation. The informal but substantive banter highlights not only the entertaining side of political commentary but also the seriousness with which Holmes and his colleagues approach authenticity, connection, and growth—both professionally and personally. The message: stay curious, be real, work hard, and value the people in your corner.