Jimmy Iovine, pictured in front of Ed Ruscha’s “Our Flag,” started the decade running a major label and ended it retired from his position at Apple Music.

The record executive who made the leap to Silicon Valley looks back on the decade in the music business, and sees a major problem on the horizon.

The biggest story in music over the last decade was the industry’s reconciliation with tech — after a decade fighting the internet, the music business fully embraced it in the 2010s. Streaming has now finally returned the business, which was nearly decimated by the shift from physical to digital formats, to growth.

Perhaps no one has had a broader view of this phenomenon than Jimmy Iovine, the producer and record executive who made the leap to the other side. He and his partner, Dr. Dre, sold their company, Beats Electronics, to Apple for $3 billion in 2014 and helped launch Apple Music, the tech giant’s late entry to the streaming market, which now has more than 60 million subscribers.

It was, from the start, a strange pairing. Apple is obsessively cautious in maintaining its public image; Iovine, the son of a Brooklyn longshoreman, blurts profanities in a high-pitched rasp and is one of music’s great hustler-salesmen. But Iovine, who co-founded the Interscope label in 1990 and led it until he left in 2014, has long been one of the sharpest observers of the tug-of-war between the entertainment business and Silicon Valley.

Iovine, 66, retired from Apple in 2018, and says he has devoted himself to passion projects like the XQ Institute, an educational initiative led by Laurene Powell Jobs, who was married to the Apple co-founder Steve Jobs. He has even started taking guitar lessons. “I’m realizing how hard Tom Petty and Bruce Springsteen’s jobs really were,” he said from his home in Los Angeles, with a chuckle.

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Iovine has also become a dedicated collector of contemporary art, guided in part by David Geffen, his friend and fellow mogul retiree. His most prized work is a 2017 commission by Ed Ruscha, “Our Flag,” an update to one of Ruscha’s perennial subjects that shows a star-spangled banner ripped and tattered — a striking comment on contemporary politics.

“If you looked at the painting and thought it represented the disarray of democracy you would be right,” Ruscha said. “Any flag that flies for 250 years deserves to be a little soiled but nothing this extreme.”

In a series of conversations in December, Iovine spoke about his career transition from the studio to the halls of Cupertino, and the tangled relationship between music and tech in the 2010s. Artists, he said, are more powerful than ever, thanks to social media — but too few, in Iovine’s opinion, have made social statements as bold as those by the 82-year-old Ruscha and “Our Flag.”

“This painting says more than any song that I’ve heard in the last 10 years,” Iovine said. “Why is that?”

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These are edited excerpts from the conversation.

Back in 2010, you were still at Interscope, where you had hits with Lady Gaga, Eminem, the Black Eyed Peas. At the same time, you were building up Beats. But within four years, you left the label and sold Beats to Apple. Why did you take that trajectory?

What you’re talking about actually goes back 20 years. It’s all a response to Napster. I saw how powerful that technology was, and I realized we had to switch gears. The record companies were not going to exist without tech.

Why I got into the music business originally was to be associated with things that were cool. And I realized that the record business at that moment, the way it was responding to Napster, was not cool.

Image Iovine with Lady Gaga and Dr. Dre in 2009. Credit... Dimitrios Kambouris/WireImage, via Getty Images

Meaning suing people?

Yes, and putting up a moat, like that was going to do something. So I said, “Oh, I’m at the wrong party.” And I met a bunch of people in tech. I met Steve Jobs and Eddy Cue from Apple. And I said, “Oh, this is where the party is. We need to incorporate this thinking into Interscope.”

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I find out a lot through the artists I work with. Dre is a perfectionist of audio, maybe one of the greatest audio producers that ever existed. And when I found out what Dre was concerned about, that the equipment his kids were listening to the music on — an entire generation was learning about audio through cheap, inefficient equipment. That’s how Beats started.

Steve Jobs used to sit with me at this Greek restaurant and draw out what I needed to do to make hardware. He’d say, “Here’s distribution, here’s manufacturing,” and he’d be drawing on this paper with a Sharpie. And I’d go, “Oh, [expletive].”

So what did you learn when you got to the other side?

I didn’t want it to be the other side. I wanted it to be all one thing. I wasn’t bailing on music. I always thought that technology was going to get people to listen to music in a better way, and you were going to promote it all through a streaming service. But it would all be in the same house.

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Is that where things ended up? Are music and tech in the same house, or is the house divided?

The two sides don’t speak the same language. Content doesn’t know what technology is building. And engineers are just going by the way they see a problem. The streaming business has a problem on the horizon, and so does the music business. That doesn’t mean they can’t figure it out.

What’s the streaming business’s problem on the horizon?

Margin. It doesn’t scale. At Netflix, the more subscribers you have, the less your costs are. In streaming music, the costs follow you.

And the streaming music services are utilities — they’re all the same. Look at what’s working in video. Disney has nothing but original stuff. Netflix has tons of original stuff. But the music streaming services are all the same, and that’s a problem.

What happens when something is commoditized is that it becomes a war of price. If you can get the exact same thing next door cheaper, somebody is going to enter this game and just lower the price. Spotify’s trying with podcasts. Who knows? Maybe that will work.

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And let me just say, what Daniel Ek has done with Spotify is extraordinary. I knew who he did those original deals with. Those were impossible deals, and they’re suffering from that now. All the streaming companies are. But he’s done an incredible job.

Image Iovine with U2’s Bono and the Edge and Apple’s Steve Jobs, in 2004. Credit... Tim Mosenfelder/Getty Images

If you look at the last 20 years of the music business as a recovery from Napster, has the problem now been solved?

I don’t view it as problem solved. There’s been progress, but there’s a ways to go yet. If I were still at Interscope, here are the things I’d be worried about. I’d be worried that I don’t have a direct relationship with my consumer. The artists and the streaming platforms do.

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I’d be worried that an artist like Drake or Billie Eilish streams more than the entire decade of the 1980s, according to the information I’ve seen from labels and streaming services. I’d also be worried that the streaming services aren’t making enough money, because that can jackknife.

What about the future of the record business? Why should the next Billie Eilish sign with a record company at all?

The artists now have something they’ve never had before, which is a massive, direct communication with their audience — from their house, their bed, their car, whatever. And because of that, everybody wants them. Spotify wants them, Apple Music wants them, Coke wants them, Pepsi wants them. And people that make terrible second records are still famous and still have online audiences. The power of celebrity, this obsession with Instagram — it’s driven by personality and lifestyle.

So hail to the artists, because in the end they’re winning. It isn’t their problem to figure out how the streaming company and the record company are going to make more money. It’s the streaming company and the record company’s problem to figure out how to become more valuable to that artist.

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You left Apple in 2018, just three years after launching Apple Music. Why?

When I went to Apple, it was a new creative problem for me. How do we make this the future of the music business? How do we make it not ordinary? But I ran out of personal runway. Somebody else will have to do that.

What do you think about Taylor Swift pushing for control of her master recordings?

Well, who doesn’t want to own their masters? But what she is doing is amplifying that because she has a giant platform. That’s going to have an effect, and it isn’t going to be neutral. So if you’re a 16-year-old kid making music on Pro Tools, that is now in the conversation. If I was still at Interscope. I would say, “O.K., this is coming. So I have to figure out, how do I evolve my relationships with artists?”

What’s the secret for an artist to have a long career today?

Quality — of everything you do. Make quality the priority, not speed. Speed is marketing, but you have to have something great to market.

Dre says we’re seeing a lot of quantity over quality right now. Somebody asked me the other day, how do you make a Christmas album that lasts? I said, “Don’t make it with disposable artists.” If you don’t want to be disposable, take care of the art.

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Image Iovine in the studio with John Lennon in 1974. Credit... Bob Gruen

Are you impressed by artists’ work now?

Artists have these new platforms that are very, very powerful. So why do visual artists like Mark Bradford, Kara Walker, Ed Ruscha, Jenny Holzer make such powerful statements on where we are today in our culture, like Marvin Gaye, Public Enemy, Bob Dylan or Rage Against the Machine did? What has changed?

One of the reasons I left music was because there wasn’t a kind of music that I related to. I grew up with Patti Smith, Bruce Springsteen, John Lennon. When Neil Young’s “Ohio” came out, I was 17 years old. I was a year from being drafted. My instincts said that this war is wrong. And here was a guy whose music I loved, and all of a sudden, I was part of, “We don’t agree with this.” And Neil Young had one-tenth of one percent of the platform that some of these artists have now.

These days I am getting that from the art world and not the music world.

So I call up Ed Ruscha, and I said, “Could you make me an American flag?” And he said, “Only if I can make it the way I feel about America today.” And I said, “Absolutely.”

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When I got that painting, I knew that Ed had hit on something. And I said, “Where are the musicians that are doing this?”

There are some clues. Have we entered into an age of music where artists are afraid to alienate people? Since the country is so polarized, am I afraid to alienate the other audience? Am I afraid to alienate a sponsor from my Instagram? I don’t know. I’m asking the question.

But you do have artists like Eilish who are talking about climate change.

There are a few. But not nearly enough.

If I were still running Interscope, I would be signing artists and encouraging them. Right now there are a lot of people running around saying, “What’s making noise on TikTok?”

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That’s fine. But I’m more encouraged by the people who are saying, “Whoa, this artist has something to say. I’m going to support them, because I believe that in the end they’re going to win, and that will make all of us win.”

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Ben Sisario covers the music industry for The New York Times. @sisario

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