For someone who started out as a wunderkind teenage DJ at AM station WCHJ in his native Mississippi, Bob Pittman, now 71, is having the last laugh as chairman and CEO of iHeartMedia Inc., the country’s largest radio company with nearly 900 stations in 151 markets, and $3.8 billion in annual revenue.
Radio? TV was supposed to kill radio. Satellite radio was supposed to kill terrestrial radio, like those stations operated by iHeart. Podcasts were supposed to kill satellite radio. And whatever comes next.
Pittman beams when he says iHeartRadio has more listeners today than it did 10 years ago. “TV certainly can’t say that,” said Pittman, a co-founder of MTV. The media company doesn’t break out daily listeners but claims to reach 90% of Americans every month through broadcast radio and its streaming platforms. Monetizing for the scale of that audience is a struggle, concedes Pittman, who is constantly making the case for radio’s value to advertisers and to Wall Street, which has been skeptical lately of iHeart’s large debt restructuring. The company has pared long-term debt by $400 million since 2022, but it still stands at $5 billion while the stock price is down to $1.40, a drop of 30% so far this year. Pittman declined to comment on the share price, but his message to the Street has been “we are committed to [finding ways] to operate more efficiently and take advantage of new and evolving technologies.”
And, of course, Pittman likes to point to other media’s reach versus iHeart’s: Consider that among adults 18-34, Spotify has a monthly reach of 43%, YouTube Music has a monthly reach of 35%, Pandora and Apple Music both have a monthly reach of 18%, according to Nielsen.
“Listeners want to hang out with us,” in the car, at home, on their phones, said Pittman. “It’s not about programs, it’s about media in real time.” Many people will check back in on radio seven times during a day, iHeart research shows.
TheWrap recently spoke to Pittman about the future of media, the state of radio, podcasting, how iHeart is deploying technology, and whether he plans to retire — ever. The following interview is edited for length and clarity.
You’ve always been able to see around corners in media, finding the next big thing. Where is the future of digital media headed?
To be honest, I feel like predicting the future is often a fool’s errand. For example, everyone thought the world was going to the metaverse and Web 3.0 — and instead, it went to AI, which turned out to be more powerful — and came sooner than anyone had expected and opened up a lot of new opportunities that nobody foresaw.
So my strategy is not to try and predict the future; instead, it’s to be on the lookout for the future, and to be ready when it shows itself.
Let’s get straight to it: How could the Trump tariffs impact an ad-dependent company like iHeart?
At this point in time, we’re seeing generally stable ad spend, but we of course continue to monitor it closely due to the lack of visibility. For the most part, our advertisers would not be affected by tariffs. And they learned some valuable lessons from the pandemic, to not overreact. We’re not seeing a hysteria. (During its first quarter earnings report on May 12, iHeart said digital revenue increased $38.3 million, or 16%, driven by demand for digital advertising, including podcast advertising.)
You said recently that iHeart grew to 40% of the advertising revenue and markets for radio as measured by metrics consultants Miller-Kaplan. What’s the plan to grow that slice of the pie?
The biggest argument for the share gain is that given our size, what you’re finding, particularly with the larger advertising partners, is they want fewer partners, not more partners. We certainly would have to be partner number one. And what other partners they have in radio, I don’t know. But I think that’s probably beneficial to us as the industry consolidates.
Events like the iHeartRadio Music Awards, streaming radio options for mobile devices, newsletters and podcasting have all become growing parts of your business since you became CEO. What’s your podcasting strategy?
Podcasting is really radio on demand, just like Netflix is probably TV on demand. It’s an adjacent business to radio. So we have a natural advantage here, not only in terms of creation and knowing how to do it and having the resources to do it, but we also have this incredible promotional vehicle called broadcast radio.
We’re able to advertise these podcasts, promote them, talk about them to an audience that is very audio centric anyway and understands what we’re doing here.
We’ve got the podcasts people want to listen to, and the programs — like “The Clay Travis and Buck Sexton Show,” “My Favorite Murder,” “Here’s the Thing With Alec Baldwin” and “New Heights With Jason & Travis Kelce.” We’ve got a large podcast audience and it’s growing. If you look at Podtrac, which measures podcast listening, not only do we do extraordinarily well overall, I mean a pretty substantial lead over NPR, the second largest podcast publisher, but we’ve also got it diversified across all 19 categories of podcast listening as measured by contract. So I think it starts with that.
How much are you investing in video podcasting?
When you get into how are people looking at podcasting, the vast majority want to listen to a podcast. Are there some people who prefer to watch a video podcast? Well, at that point, it’s not really so much a podcast as much as it is a video show.
Look at the success of YouTube. But I don’t think that’s the podcasting business, per se. I mean, I understand that YouTube would like to take some of that podcasting revenue, and I don’t blame them. But we think the consumer has spoken. And so although we look at it and watch it carefully, I think we’re in exactly the right position and feel very good about it.
How are you deploying technology across the company?
We remain committed to identifying opportunities across our organization to operate more efficiently and take advantage of new and evolving technologies like programmatic and AI, which are critical to delivering short-term results and long-term growth even during periods of economic uncertainty. Much of how we use AI is in mining data to better understand our audience, the consumer. We are also using technology and AI to hit our target of $150 million in net savings in 2025.

You’ve partnered since 2020 with Malcolm Gladwell’s Pushkin Industry to study the relationship between consumers and advertisers, and you make those findings public. Why do that?
We’ve always been grounded in reality about who the majority of our listeners are. The average American household has an annual income of about $70,000. The biggest purchases are maybe $1,000 or maybe $2,000 a year. It’s important to know that, for example, 44% of them believe they are underserved by advertisers. Marketers live in big cities and don’t commute as often as the average American, don’t necessarily understand the huge role that broadcast radio and podcasts play in people’s lives, particularly in the car. So it’s a matter of checking biases at the door.
You’ve spent the vast majority of your career in leadership roles in the media business and you’ve ridden the waves of never-ending change. What advice would you give to somebody looking to be a leader at a media company?
It’s pretty simple. Ignore the headlines, and focus all your energy on your consumers. And just keep asking yourself: How can I stay current?
Ok, ouch on ignoring the headlines but I get your message. One last question: You’ve been working in media since you were 15 with your fair share of wins over a long career. When do you think you will call it quits?
Listen, business is my golf. As long as my health holds up and my board wants me here, I will continue to do what I love.
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