An Open Letter to Bob Pittman and Other iHeartMedia Execs As Layoffs Hit…Again

To Mr. Bob Pittman and other various iHeartMedia Executives,

Any time iHeartMedia announces another round of layoffs, there’s going to be anger. The calls, texts, and emails will pour in. People will vent, curse, and point fingers. Plenty of folks who don’t even work for the company begin to wonder about their own fates, because if a giant comapny like iHeart can’t make it work, how is my company going to succeed? Existential dread follows, coupled with even more charges that the industry is dying and anyone who remains is going down with a sinking ship.

But this isn’t one of those times. This isn’t a letter written in outrage. It’s one written in genuine concern.

It’s clear that the business realities of radio are tough. You’re not the only company going through this. It’s almost assuredly going to happen at other radio companies before the calendar flips to 2026. Costs rise, revenues fluctuate, and every company has to make painful decisions.

But I can’t help but wonder — do you guys really hate doing this? Does waking up in the morning knowing that you’re going to cause chaos to your employees’ families make your stomaches churn? Because if you hate something, don’t you do everything you can to avoid having to do it again and again? That feels like a logical and reasonable conclusion to me. That, if you truly hate something, you’ll figure out a way to make sure you don’t have to do that again, and if you do have to do it again, you’ll make sure you’ve exhausted all other options beforehand.

And, from an outsider’s pespective, it doesn’t feel like that’s the tenacity with which you work.

At this point, layoffs have become a near-annual, sometimes even semi-annual, event for iHeartMedia. They’ve become so predictable that employees brace for them like they do for bad weather: they know they’re coming, they just don’t know when.

And that’s a problem. Not just for morale, but for the soul of the company, and the industry, really.

For a company that has gone through rounds of layoffs more frequently and robustly than any other radio company, there’s still one thing that’s abundantly clear: you guys are really not good at this.

I’m a firm believer in that you can be the boss so long that you forget what it’s like to not be the boss. Empathy toward employees can easily fade when you’re only surrounded by those who think and act like you, and are more worried about self-preservation than anything else. That knowing what it’s like to be the managed instead of the manager is fleeting, gone in such a short time you can’t really remember the thoughts and feelings you had toward those above you in the corporate heirarchy.

With that in mind, I’d like you to go through a thought exercise with me: put yourself in your employees’ shoes for just a brief moment.

Think about what it must be like to make it through Tuesday’s rounds of cuts, only to have to come in to work on Wednesday, or Thursday — or even Friday, for that matter — wondering and worrying about whether or not the Market Manager is going to give you the dreaded “Hey, do you have a minute to meet in my office real quick?” Questioning if you really did make it through the cuts, or if they just haven’t gotten to you yet. Wondering what your future looks like. Are you gonna have to sell your house? Is a move in the cards? What am I gonna have to do to make it? Will there even be another radio job out there for me?

Now, you can see how that would absolutely suck, right? So, my question would be: why do you continually do it? Not the layoffs. I’ll give you the benefit of the doubt in that these are absolutely necessary for the company’s survival. I’m certain they’re not, but for sake of the argument, let’s go with that.

Why do your company’s layoffs routinely last days? It isn’t 1984 when word would slowly trickle out that someone in some far-flung locale had been let go or that news of mass layoffs at a company would come out days after the fact. We live in an instantaneous world, where these things are reported immediately. So, when word gets out that there are plenty of layoffs taking place, people know.

Have some humanity. I’m certain that it absolutely sucks to swing that ax. And I’d like to think that you hate swinging it. But why prolong it? Why take extra chops and put employees that you’re — in theory — supposed to care about through extra psychological torture?

Do the employees ever put themselves in your shoes and consider what the ramifications are for not cutting costs and slashing positions? No, not likely. But that’s the burden of leadership. That’s the downside of being tasked with running a radio giant. I’m not naive enough to think that there aren’t aspects of your jobs that suck, despite never really getting the chance to air those grievances.

I don’t envy the position you’re in. I wouldn’t ever want to be in a position where I had to continuously figure out how we’re going to cut our way to prosperity, because I don’t believe that pathway exists. And I also know that this is a business and business is business. You gotta do what you gotta do. I understand and respect that.

But I hope you believe that you win with people. You’re running out of those people, though. And even worse yet, you’re inflicting torture on those who are busting their tails for you day in and day out. I know it’s not easy, I know it’s not fun. Maybe there are reasons for why you can’t get layoffs done in one fell swoop. But I think you need to figure out how you do that, because once you’re able to stop the bleeding, the healing can begin.

Futhermore, I hope I’ve given you something to think about. Because I have a deep appreciation and respect for the work you do and the situation you’re in. As I said, I wouldn’t ever want to be in your shoes. But that’s why you make millions and I work from a spare bedroom in my house.

I thank you for your time. I know how insanely valuable it is. And I wish you the best of luck going forward. In many facets, your success is the radio industry’s success. Like you, I want to see that industry not only survive, but thrive going forward.

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Garrett Searight

Garrett Searight is Barrett Media’s News Editor, which includes writing daily news stories, features, and opinion columns. He joined Barrett Media in 2022 after a decade leading several radio brands in several formats, as well as a 5-year stint working in local television. In addition to his work with Barrett Media, he is a radio and TV play-by-play broadcaster. Reach out to him at Garrett@BarrettMedia.com.