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Derek Hunter
This is an iHeart podcast.
Carol Markowitz
Guaranteed Human.
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Derek Hunter
Chloe Kim with the gold medal.
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Derek Hunter
In April, and now I have customers out the door.
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And this is Sarah.
Sarah (Business Owner)
Hi.
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Business is big, booming. That's why I'm working on a Saturday.
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Carol Markowitz
Welcome back to the Carol Markowitz show on iheartradio. My guest today is Derek Hun. Derek is a columnist for Town hall, author of the book Outrage Inc, Podcaster and radio host at WMAL in D.C. and someone who has had 81 jobs and counting. Hi, Derek. So nice to have you on.
Derek Hunter
Hey, Carol. Thanks for having me.
Carol Markowitz
I mean, 81. What's going on?
Derek Hunter
You'd want to talk about lost souls. That's it. You flounder around. You start off when you're 15, keeping score of softball games and losing track of what's going on in those games and get fired for that. Then drawing lines on the softball field with chalker. And they go like this because it's much easier to guess what a line looks like than to hammer in the chalk line.
Carol Markowitz
Okay.
Derek Hunter
My entire teen years were looking at.
Carol Markowitz
So wait, are those jobs one and two?
Derek Hunter
It was job one and like four. There was a couple of jobs in between. I made sandwiches. I was a Busboy. I worked at a sub shop. I was a busboy. I was a waiter. I worked maintenance at a trailer park. You. I was a maid for an hour.
Carol Markowitz
For an hour.
Derek Hunter
I was hired by Merry Maids. That's desperate for a job. I was like 18 years old, aimless. Went and watched the train, filled out the paperwork, watched the training video. Came out about an hour after the paperwork and all. There's my crew of nice probably old ladies sitting there. And I just looked at them and I said, I can't.
Carol Markowitz
I can't forget it.
Derek Hunter
And I walked out and they mailed me a check for like $5 and change.
Carol Markowitz
Nice.
Derek Hunter
Pretty much done. I've done it.
Carol Markowitz
What was the weirdest job you've had? Or is that it? The made.
Derek Hunter
No, this is a difficult one to even explain. When I was a. When I was in college, I found a job on a message board somewhere online. Back in the Internet was all dial up that I drove around to 16 area hotels five days a week and read the events board into a micro cassette recorder. And then I. Yeah, like, okay, you know, breakout session. This room. It was just stupid. And then once a week I would FedEx that out to a woman in Utah who transcribed it for. I assume. I never really found out. It might have been an elaborate money laundering scheme. But it was for a newsletter where hotels could subscribe and then steal business from each other. Cause they would see the oldest companies having their meetings at this particular hotel every three months or whatever. So they try and steal. That's the best I could do. I never literally spoke. I never spoke to anybody.
Carol Markowitz
You never asked, what is this?
Derek Hunter
I never spoke to. I answered that ad. I met the guy who was doing the job at a diner, had breakfast, drove around to the hotels. He said, do you want it? I said, sure. It was like two hours worth of work for $425.
Carol Markowitz
Oh, there's something very suspicious about that.
Derek Hunter
And he slid me a folder with the hotels and everything and a bunch of micro cassettes and a bunch of liqu labels for FedEx. I took it. I did it. I did it probably for two years. I got to the point, this is terrible. I would go and just go up to the desk. I'd get to know the people who worked there. And I'd get the entire week's worth of events on Monday and I would just be done. I'd work one day instead of five days. And then I had so many of it, so much of it repeated. And weddings, I just made it up sometimes. This is why my attitude was so bad. This is how you get 81 jobs, is you get the easiest tap in, putt of a job job, and you go, I bet I can do it even lazier than it actually is. And you do that. But I kept the job for about three or four months after I moved to Baltimore, after I graduated. That's. I did it 5 miles away or 500 miles away. Fake for a while and then I just kind of quit.
Carol Markowitz
How do you know you actually gave.
Derek Hunter
It to a friend of mine who was lazier than me and couldn't keep it. That's how bad it was.
Carol Markowitz
How do you know you weren't, like, sending this to, like, Chinese spies or Russian, you know, agents?
Derek Hunter
I don't know what they could do with it. You know, you got the, the Horowitz bar mitzvah in the salon, three on Saturday at noon. Like, if you need that information.
Carol Markowitz
Crashed that bar mitzvah.
Derek Hunter
All that information. Carol is online now, but it was in like, a piece of paper that they would put out for guests to come out and figure out where things were.
Carol Markowitz
Well, I was thinking, is it online now? It's not really. Like, hotels don't post. Like, we're going to have this, you know, pharmaceutical company meeting in conference room.
Derek Hunter
I'm sure you could get it by phone, especially if you, you talk to them.
Carol Markowitz
Yeah, I don't know. I. I think it was the weirdest thing. I think you could go back to them right now and say, I want my job back.
Derek Hunter
I wouldn't even know. I don't remember what the company was called. I don't remember anything about it. I just. There's some old lady or some woman's name. God knows. Nowadays nobody knows what a woman is. I would FedEx it off to. To Utah. I never heard a complaint. The check was mailed. This was long before direct deposit. And I, I coordinated via email and I got a $75 a week raise. Maybe it was every two weeks. Maybe it was every two weeks, but I got a. I got a raise to $500 after like a year. Amazing. It was because I asked for it and it was just an email and they said yes. And that was about the exchange. That was it.
Carol Markowitz
So how did you get into media from this?
Derek Hunter
Well, it's a natural progression. Obviously the script writes itself.
Carol Markowitz
Actually, I was actually thinking you should write a movie about this, about what you think is actually happening on the other side of receiving those tapes in the mail.
Derek Hunter
I could. My just professional story, not a private life, too, would be Just a very long cautionary tale. I've made the mistakes so you don't have to. But how I got into media, I don't know. After I graduated college In December of 2000, I should have graduated in June or whatever of 2000, but I had to take my college required. Two years of German, two years of a foreign language. I have pretty severe dyslexia, and I, I. German is awful. It sounds like somebody with pneumonia having sneezing feet. German. I had a girlfriend at the time who spoke fluent German when I started taking German, and so she could help me cheat. I had taken a German in high school a little bit, and I. So I knew how to say the basics, but it just. The gender and all, it was just terrible. So I had to take German 202 outside fantasies of junior year in Germany, which never happened, as the girl and I broke up and I would have starved to death. But I. I had to take 202 German 202 three times. And so I set it up so it was my. Yeah, it's like, there's no way I'm gonna get a passing grade. And like, yeah, no, you're not. And I was taking it with a full load. So my last semester, that extra semester was just German. Like, I. I could handle it there. I'm pretty sure it was a pity grade. I don't even remember what it was. But they just said, all right, go ahead. Just promise never to say enough of this. Never tell anybody where you learned your horrible German. And so I graduated. I got a job in the bookstore at the Heritage Foundation.
Carol Markowitz
Oh, wow.
Derek Hunter
It was on the fourth floor. So there's nobody coming in. You're just answering phone calls in 2001. Yeah, 2001. From old people who don't know how to access the Internet and get the backgrounders for free there. So you had to, like, mail them out to. That was my job. I started doing volunteer research for people in healthcare and education and ended up getting a research assistant position in that. And then Medicare Modernization act came and it blew up. There was only two people doing health policy at the Heritage foundation, and neither of them were doing prescription drugs. And that's what that bill was. So I. I was sort of given that. One was Medicare, one was Medicaid, and I was the prescription drug guy. And so I started doing media hits from there. I'll tell you how sad it was. I was making such little money. I lived in Baltimore. I had to take a train. I don't know if the statute of limitations has run out. It's been 20 years. They couldn't prove it.
Carol Markowitz
Is there a crime here?
Derek Hunter
They can't prove it. There's definitely a lot of felonies there. A friend of mine would make my monthly pass train tickets on Photoshop.
Carol Markowitz
Wow.
Derek Hunter
Because they were $143 and I didn't have $143, so that's wild. I didn't have a phone. So when I had to do a radio interview anytime outside of normal business hours, I had to stay around the Heritage foundation to do it on their phones. I couldn't afford a ph. And eventually that led to somebody who was in the PR shop coming by one day. This was 2004, 2005. And I just go, hey, Derek Hunter. Radio started like, what is that? I don't want to stay after. I don't want to do it or interview. So I went to her office and I ready to get out of it. And there was something called writetalk.com I.
Carol Markowitz
Think I had a show on that.
Derek Hunter
Like the first streaming. Yeah. My friend Liz was one of the producers. I didn't know this at the time, but they said that senior management, they were offered the show one day a week for an hour. Nobody listened. But they.
Carol Markowitz
Oh, we had listeners. We had very dedicated listeners.
Derek Hunter
Senior management asked who could do it, who could speak for an hour without going oom and ah. And my name kept coming up. So they gave it to me. It was great. Cause I got basically Wednesdays off.
Carol Markowitz
Yeah.
Derek Hunter
And we had a lot of fun with that. That led to podcasting. That led to, you know, some. It's weird. Neither one of my parents graduated high school. None of my siblings went to college. So nobody knew what a think. Everybody I knew in my world was, what do you do to think tank? Sit around, think all day, Right.
Carol Markowitz
Yes.
Derek Hunter
And like, kinda. But you know, when they'd see you on TV or something, they'd go, at least he's dead. He'd be real. He's alive, he's real, he's wearing a suit, whatever.
Carol Markowitz
Right.
Derek Hunter
And so from there, it just progressed to podcasting with a happy hour that I'd started with a friend. And then Saturday fill ins at UMAL just for fun. And then a job in Baltimore. And from there just. I got taken to lunch by Jonathan Garthwaite at Town hall and the then editor, Kevin Glass. They liked my Twitter feed, the attitude of it, and they wanted a column with that attitude. So they asked me if I wanted to try that. I said sure. And I ended up. I submitted for like the first two months, I submitted 3,500 words, like three, four columns all in one thing on a Sunday. And they said, well, that's great, why don't we, it's working. Why don't we just do more than one a week? And so from there it's just led to four columns a week and a book and all kinds of weird stuff that I would never. You couldn't plan it. If somebody had said, how do you get into radio? Like, I don't know, never stop talking. And that's it. But one of the weirdest things.
Carol Markowitz
But that's a long, strange trip.
Derek Hunter
Really. You have to have experienced this. When I started doing fill in work, like I was the last new fill in for Rush Limbaugh before he passed away. And I started doing fill in work and being heard on the radio that I'd go to. I worked at Americans for Tax Reform for Grover Norquist. And there's that big Wednesday meeting, 150, 200 people. And a bunch of them come up to you and go, you should have them have me fill in.
Carol Markowitz
Right?
Derek Hunter
Like, first of all, who are you? I don't think you could do that. You're kind of dumb. Secondly, what kind of juice do you think I have as the occasional fill in guy? And third, screw you.
Carol Markowitz
Okay, I met this stranger.
Derek Hunter
Yeah. Hey, there's this guy I know. He really thinks a lot of himself and he loves to hear himself talk. It's one of those things, you know, before you got into this, you probably thought this was going to be one way and then you do it and you realize it's completely different. There are some people who can and some people. It's not brain surgery, it's not saving lives or anything. I'm not trying to congratulate myself, but there are some people who have a three hour show and 10 minutes in they're going, here's the number. Please call somebody. Please call. Whereas there are other people.
Carol Markowitz
I don't think I could do three hours. I, you know, it's not that hard.
Derek Hunter
Three hours in front of you is forever. Three hours behind you is like, what just happened.
Carol Markowitz
Both of my shows are 30 minutes and I feel like that's a very sweet spot for me.
Derek Hunter
Well, it's not that hard, especially once you do it. It's, you know, not a lot changes one day to the next. So there's repetition and then history is always the same. So whatever you learned before is still valid and you can recall it and use it at any given time. You just have to be willing to. Weirdly, I hate public speaking. I just turned down a speech in Maryland for a Republican club. Like, hey, we wanted to get you to come out. I'm like, nah, I don't think so. I gave it to Larry o'. Connor. I said, contact Larry o'. Connor. He loves talking in front of people.
Carol Markowitz
He's great.
Derek Hunter
Yeah, I don't love talking in front of people. But you do it for a living. There's me and a microphone and that's it. I'm very good. The cats are attentive listeners and they love my show and that's my audience.
Carol Markowitz
So this job is gonna take. Is what you're saying.
Derek Hunter
This.
Carol Markowitz
This is.
iHeart Radio Advertising Representative
This is.
Derek Hunter
I hope so.
Carol Markowitz
Yeah. How long you been doing this, like, specifically your radio show?
Derek Hunter
I've been. I started in, I don't know, probably 10 years ago in Baltimore. Someone had. A local legend had passed away. That seems to be the only reason there's opening. And I did that for a few years and then just wait for somebody to die. Yeah, they wanted to go hyper local. And I. I just. I'm not hyperlo. I didn't. I don't even know. I lived in Baltimore for 13 years. I couldn't name the mayor. Most of that time, it just wasn't my interest. And then another. The other station in Baltimore called after I was let go and I started doing fill in and then they had somebody pass away and so I'm here till I die. So I got that job.
Carol Markowitz
Circle of life, really.
Derek Hunter
Then they wanted to go local and I just said, I'm done. I'm kind of done with radio. I didn't want to do it. I wasn't willing to move to do it. I just, you know, I have a family, you know, and it just. It's too. It's way too unstable to count on.
Carol Markowitz
Yeah.
Derek Hunter
And then this job opened up and I was like, well, I'm here. My wife is the morning show executive producer. Like, I know the people here. I've filled in for every show on the station here. So I'll try because it doesn't. I don't have to move anywhere. Like, you could be the king of Cleveland. Like. Yeah, but you're in Cleveland.
Carol Markowitz
Exactly.
Derek Hunter
I was already here. And, you know, possession is 9 10. The law and location is 9 10, the battle to get a job in radio. And so I was lucky enough to get it.
Carol Markowitz
What are you most proud of in your life?
Derek Hunter
My kids just have. If I could travel back in time, aside from giving myself a lot of Stock tips and, you know, like, buy gold and buy silver. And then I'd steal the money to get it. I would just smack myself upside the head. For the longest time, kids were not. They're gross. They're disgusting. I didn't enjoy wiping my own butt. I sure didn't want to do it for somebody else.
Carol Markowitz
Right?
Derek Hunter
And I was the worst uncle. I have seven nieces. I had one time, my sister had me babysit just once, and.
Carol Markowitz
And she was like, that's enough of that.
Derek Hunter
Well, she was the oldest, and it was the oldest kid. And then the news traveled and there was nothing. It was one of those explosive. My sister was about 10 minutes from being home, and it was one of those explosive bowel movements that somehow defy gravity and go up like, I don't even know how this happens. And I saw it and it smelled and it was like I'd never changed a diaper and not start now and not start with that thing. And so she was in her pajamas. I sprayed her butt with Lysol on the pajamas. Plausible deniability. I thought it was a perfect crime. I kind of stuck her.
Carol Markowitz
How old were you for this? Don't tell me, like, I was older than I was.
Derek Hunter
Old enough to know I was. I was teens. I was old enough to know.
Carol Markowitz
Okay, late teens.
Derek Hunter
I think I was still in high school, but I was like, teens.
Carol Markowitz
Almost excusable. Teenagers.
Derek Hunter
It didn't matter. But word got around and I didn't get any better at the babysitting, so, like, there was never any babysitting.
Carol Markowitz
But with your own kids. With your own kids, yeah.
Derek Hunter
It's not all that different. It's just that there's nobody to spray the butt with. Lysol that's going to be coming home soon. I'll give my wife credit. With both kids, she was like super mom when she was on maternity leave. So I didn't. The first kid, I didn't change a diaper for like, six weeks. What about the bonding? I don't need that kind of bonding. Yeah, but every time the kid, like, coughed or she was up, my wife was up running around like, I don't have to do anything. Kids are easy. Then she went back to work and.
Carol Markowitz
It'S like, yeah, come get these kids.
Derek Hunter
And then it's. It's not that bad. Still not, you know, an aspiration bucket list, but it's.
Carol Markowitz
How old are they now?
Derek Hunter
Seven and eight.
Carol Markowitz
Okay. It's not that much butt wiping at this age.
Derek Hunter
Not much. Still more than you'd like.
Carol Markowitz
It's still the occasional, you know, put cream on my butt.
Derek Hunter
There's a lot of come look at my poop.
Carol Markowitz
Yes. Yes. There's some.
Derek Hunter
Come look at my poop. Good job. Did you wipe? Did you wash? Did you don't need to see it, but congratulations.
Carol Markowitz
We're gonna take a quick break and be right back on the Carol Markowitz Show.
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Derek Hunter
The moments Chloe Kim with the the gold medal.
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Flex the stars.
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Derek Hunter
Give.
Carol Markowitz
Us a five year out prediction can be about anything at all, however.
Derek Hunter
Oh God, I don't know. In politics or.
Carol Markowitz
It could be really, it could be anything that you find interesting that you want to lay a prediction on the line here and have us make fun of you in five years when it doesn't come true, or herald you as a hero when it does.
Derek Hunter
There's something you're holding onto right now that you will kick yourself for still having in five years because you will have missed the sweet spot for selling it. Whether it's silver right now, whether it's bitcoin, whatever, it is something that you have. You're like, this is my long term get rich quick scheme. There will be a point where you should have sold it and you won't.
Carol Markowitz
All of my son's Legos.
Derek Hunter
No. What are you going to step on and curse existence in the middle of the night?
Carol Markowitz
He swears that he's going to be the wealthiest of all the three kids because of these Lego sets that he has. I feel like now they're an investment. Yes.
Derek Hunter
Look, I have a bunch of baseball cards in a safe deposit box.
Carol Markowitz
Oh, yeah.
Derek Hunter
I. If I had sold during COVID I would have had a ton of money. They're still worth more than I paid. But if you, you look back and just last five years.
Carol Markowitz
Yeah.
Derek Hunter
During COVID everything, everybody got nostalgic and nobody was buying gas, so they had disposable income and they went crazy and they sold it. I have, I will tell you this, Carol. I have. I think it's 56,000 Sheba anew coins, which you're looking at me like, what?
Carol Markowitz
I don't know what that is.
Derek Hunter
I don't know either. It's a, like a bitcoin thing or whatever they are.
Carol Markowitz
Oh, I vaguely remember this. Yes.
Derek Hunter
That is worth like $000004 or whatever. I.
Carol Markowitz
Maybe it comes back.
Derek Hunter
You know, I dump like, no, it's never worth much of anything. I dumped like $300 into it because I knew I'd waste that $300 some other way. And like, well, if in 20 years this gets anywhere near a quarter, I'm rich.
Carol Markowitz
Right?
Derek Hunter
If it doesn't. It's $300 I've probably never thought about again. So I've got it. If it somehow Fluky gets worth something, I will buy an island.
Carol Markowitz
So what is it worth now?
Derek Hunter
I don't know. It's not worth anything. It's still.
Carol Markowitz
So your 300 has now. I mean, but how much of your 300 is left?
Derek Hunter
I think it's still right around this. It was up to like 800 at one point and I thought, I'm on my way. But it's still like the actions of a penny. And then I called my broker. I was gonna buy a guy, Jeff Epstein's his head, an island. He had fire sale they had to get rid of. It's pretty cheap. But then it didn't pay off, so the deal fell. I don't even know what happened to that guy, but I'm sure somebody find out.
Carol Markowitz
Yeah.
Derek Hunter
Yeah.
Carol Markowitz
Well, Derek, I have loved this conversation. I. You are hilarious. I. I kind of knew that, but I don't feel like I knew that on a bigger level. But you're very, very funny. I really loved talking to you. Leave us here with your best tip from my listeners on how they can improve their lives.
Derek Hunter
Hang around with smart people and find someone like me who's already made all the mistakes and listen to them. We're not trying to screw you over. The stove is hot. It will burn your hand. You don't need to figure that. Not everybody needs to touch it and lose their fingerprints. Don't take advantage of the people who have done it right. And learn from them. And take advantage of the people who have done it wrong and learn from them too. And sometimes you find that in the person. But if you think you know everything, that's when you're at your dumbest.
Carol Markowitz
I love that. Learn from other people's mistakes. He is Derek Hunter. Check him out at town hall and at wmal. Thank you so much for coming on, Derek.
Derek Hunter
Thanks for having me.
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Derek Hunter
This is an iHEART podcast.
Carol Markowitz
Guaranteed human.
Podcast: The Clay Travis and Buck Sexton Show
Host: Carol Markowitz
Guest: Derek Hunter
Date: February 18, 2026
This episode features a lively conversation between Carol Markowitz and Derek Hunter—a columnist at Townhall, author, podcaster, and radio host. The discussion explores Derek’s “wild” and eclectic career path (including his claim of having held 81 jobs), his unconventional entry into media, enduring lessons from his journey, and candid advice for listeners. With humor and humility, Derek shares behind-the-scenes stories and unique life and career observations.
Starting Young and Bouncing Around
The Strangest Job
Academic Obstacles and Heritage Foundation Beginnings
First Media Appearances & Radio
Reality vs. Expectations
Skillset and Preferences
On the Motivation for Career Choices:
On Media’s Surprising Pathways:
Survival in Radio:
On Family Priorities:
Life Advice:
The conversation is witty, self-deprecating, and honest, offering a rare behind-the-scenes perspective on conservative media and the quirks of both career-building and parenthood. Both Derek and Carol sprinkle the dialogue with wry humor, relatable confessions, and candid advice.
Derek Hunter’s professional journey is anything but linear—rife with odd jobs, accidental turns, and a healthy dose of cynicism and self-awareness. His story underscores the unpredictable nature of careers in media, the importance of adaptability (and a sense of humor), and the value of learning not only from your own mistakes but from others’ as well.