When Julie Swidler, Sony Music’s executive vp of business affairs and general counsel, steps down today (June 30) after 18 years at the company, the record industry will lose one of its most accomplished, respected advocates — at least in her current capacity.

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But even after her exit, Swidler, one of the highest-ranking women in the record business, will still be supporting the music community. In her next chapter, Swidler — who has regularly appeared on Billboard’s Power 100, Top Music Lawyers and Women in Music lists — is launching an advisory services company for creative-focused ventures.

Swidler began her industry career at Polygram Records in the late 1980s, and has also held senior legal and business affairs positions at Mercury Records, Arista Records, J Records (helping launch the label with Clive Davis), RCA Records and BMG. She also served as lead counsel for the 1994 Woodstock Festival.

Throughout her career, Swidler has been in a front-row seat while the record industry has undergone massive shifts from relying on physical media to digital downloads to streaming, often navigating the legal challenges along the way. And now, as the industry faces a far bigger challenge in AI, she remembers successfully surviving other critical junctures.

Despite all her success, Swidler, who Zara Larsson immortalized in 2017’s “Make that Money Girl” (“Julie Swidler / Run a buildin’ everyday”), cites another song when describing how she’s often looked at her career.

“I always felt like I was a little bit of an outsider, because I was,” she tells Billboard in her final interview before exiting the Sony building. “When I started, there were very few women. No mothers. And I had three kids by the time I became head of business affairs at Mercury [in 1995]. I’m very big on lyrics. I never loved the show Wicked, but the first time I heard ‘Defying Gravity,’ I was like ‘That’s how I feel.’ I always felt like I was just lucky to be here, and that, somehow, I was defying gravity.”

Swidler spoke to Billboard in early June in her New York office. She talked fondly about mentor Davis less than two weeks before his June 22 death, shared some of her favorite career memories and revisited major industry milestones.

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Why is now the right time for you to go?

I don’t know if you ever know when the right time is. It’s not like you wake up one day and you say, “It’s time!” I’ve been thinking about it for a while, and over the years in my career I’ve seen a number of people wait a little too long before leaving and I always wanted to walk out on my own two feet. I also knew if I ever wanted to do anything different, I had to get off the stick and do it. I had been talking to [Sony Music Group chairman] Rob [Stringer] about it for a while as to when the right time would be. And while I’m extraordinarily sad and terrified, at the same time I haven’t thought twice about the timing.

What has been the most gratifying win of your career?

The number of people, both lawyers and non-lawyers, who have told me that I was a great mentor to them. That means everything. Recently [a] CEO of a label was telling me how fantastic their senior [business affairs] person is, and asked, “Do you know this person?” And I said, “Yes, actually, I hired them.” It’s the number of lawyers [and] non-lawyers who have developed into amazing executives who say to me, “You let me fly and were there to support me.” And if that is my legacy, to me, that’s a huge win.

There’s a Julie Swidler diaspora out there.

Exactly. [Laughs] And, all of a sudden, I’m hearing these things that they’re calling “Julie-isms” that I didn’t even know I had. There was one thing that I said years ago that everybody laughs at: I always call business affairs Rome, in that “all roads lead to Rome.” Because given the kind of business we’re in — we are such a rights-based business — we have to support everybody. One of the things I’ve always told everybody is that there’s a reason we’re called business and legal affairs and not just law, because if you don’t understand the business, you will not be able to give good advice. You may say things as a litigator because you think it’s a good reason to go after the other side, but we can’t look like dogs going after an artist. We always have to think about, “How will this reflect on us as a company?” Whether it’s litigation, whether it’s mergers, whatever it is, we have to think about that. Otherwise, we’re not good at our jobs.

Why are there still so few high-ranking women at record labels?

I’m not sure. I think it’s hard still. I think sometimes as women we feel like we need to do everything perfectly before we take on a new role. Most men are not like that. I can give you an example of a woman who was promoted a few years ago, who I knew was going to do a phenomenal job, but when we were talking about [the promotion], she said, “But I don’t know everything about business affairs. I don’t know everything about this, and I don’t know everything about that.” And I said, “You realize you’re acting like a girl because most men would not sit there and say, ‘I need to know everything before I take on this role.’ You will do phenomenally well in this job.” And she’s done very well.

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One of the executives you’ve worked with most closely is Clive Davis. What is the biggest thing you learned from him?

I love working with people that don’t necessarily feel like they have limits, and I wish I felt like that more. I think that Clive never, ever put people in a box. He didn’t say to you, “Oh, you can’t do that because that’s not your job,” or, “Stay in your lane.” He tried to figure out what people’s strengths were, and he had you work within those strengths, which was an amazing learning experience. So, if he thought I was the right person to give comments to a songwriter on a song, he would have me do it. He would hold the bar really high, and I would sit there and say, “My God, I can’t,” and most of us were like that: “I can’t possibly do that. What is he thinking?” And then you would accomplish it and you would go, “Oh my God, he’s going to expect me to do it again.” [Laughs]

So, Clive really made you stretch your wings.

Yes, in many, many ways he did. I think that I had even before, but I think he expected so much of his people that he made you push [yourself] because he pushed himself so much. People ask me sometimes, because I know there’s so many different stories of Clive, “Did he really know what was going on with the business?” And the answer was yes. Every detail. But he knew that it was better to leave some of this stuff to others, so that he could be the creative person that works with the artist. But he knew everything… He had his share of yelling, but I never thought it was personal. It was more he was frustrated with the situation. There were times where I worked with people who would yell, and it would get personal. He was definitely not like that at all.

What’s the biggest change you’ve seen in artist contracts over your time as a label attorney?

[They’re] much shorter. I think the period of time that a company has to actually develop artists and break them has become probably too short and makes it much harder. People talk about labels and doing this job of developing artists, but in many ways the deals have made it more difficult to do that. There are still amazing artist development people out there, but if they [only] have two albums [on the contract], they’re not going to be able to do very much.

If you think of the biggest artists that have broken over the last however many years, it’s because somebody believed in them over very long periods of time, and then they have decades-long careers. The shorter deals make it very difficult. It’s not about the money; it’s really about the amount of time that it takes to develop an artist and to make sure they grow and work with the right people. If you think of the greatest artists of all time, very few [broke out on] their first album.

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Looking at AI, Sony hasn’t settled with AI music generators Suno or Udio, making Sony the only major that hasn’t settled with one or the other. Why not?

I don’t think we feel compelled to settle. To start off, they stole our music. They don’t even deny they stole our music. This company is very much driven by what artists want. When YouTube started, believe me I think we would have been very happy to sue YouTube and to not work with YouTube. But the artists loved it, and they felt that YouTube was a promotional vehicle at the time to promote other aspects of their business. In a way, because the artists forced us to settle with YouTube, we settled with YouTube, and we developed a business with YouTube over the years.

The artists aren’t pushing us to settle with Udio or Suno, and so we have to think about what’s right for them, what’s right for us, who’s willing to work with us. Because certainly I can tell you that at least one of them is not willing to really work with us. The other one may be — who knows? We have the advantage in many ways of not being a public company. Yes, the bigger Sony [Corporation] is, but we don’t feel compelled to make a deal. I think we feel like we want to make a deal when it’s the right deal. When it’s right for artists. When it’s right for us. It would be different if the artists were clamoring and saying, “We really want you to do those AI deals,” but none of them are.

As a label business affairs person, what does ethical AI look like to you?

Where the company that wants to develop whatever product they’re developing comes to us and says, “We want to use your several hundred years of music to train our AI product, and this is the type of product that we would like to put out. And, by the way, we’re willing to pay you market rates.” So far, a lot of the AI companies have come to us and basically said they want the vast majority [of revenue] and the little bit that’s left over can be for the artists and the songwriters and everything else.

For whatever we say about Spotify, [founder] Daniel Ek went to all of the companies and said, “I have this idea and I really want to license your music, and this is what I think it could be.” He came to the business and he worked with us. What I’ve always tried to explain to people at the time was Daniel was like the 250th person to come and tell us that. We had done hundreds of deals already, so it’s not like we definitely knew that Daniel was the one, and, therefore, we took all this equity because we knew the equity was going to mean something. Believe me, there were hundreds of other deals where we had equity, and the companies went belly up. We were trying to do deals with everybody at the time because we didn’t know what would work. But the difference was these were people who came to us and said, “We’re not going to take your music and screw you and once we get up and running, you’ll have no choice but to deal with us.” So, to us, ethical AI is where somebody comes to us and says, “We want to properly license music,” and then we will develop a product that works for everybody.

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What is an example where the record industry got it wrong?

The fear originally that we had of the internet. I think everybody feels we got it wrong then. I think that the other thing we should have done that people tried to do was get a better deal from Steve Jobs when he started iTunes, because think about how the music products turned Apple around so he could sell the hardware.

Did you see anything that was as big a threat to intellectual property and copyright during your years at labels as AI is potentially now?

I really do believe if we had lost [the case against peer-to-peer network] Grokster [in 2005], we would have been dead in the water. Absolutely. I remember even after winning Grokster, we sued [file-sharing program] LimeWire. It was the exact same fact pattern, practically. It took us at least six or seven years to get them to shut down LimeWire [in 2010]. When I started, there were six major music companies. There are three now. Thousands of people have lost their jobs in the music business. Nobody talks about it.

I remember at one point, one of my first jobs here [was] I had to sign separation agreements, piles and piles, and after a while I would feel awful when I got home at night because I knew there were real people behind every agreement. And so, if we had not won Grokster, we would have been in big trouble because none of the streaming services would have been able to survive. It was both coming up with a legitimate service that everybody liked, like a Spotify — not even an iTunes; Spotify was way bigger in some ways — and winning Grokster. It was almost like both of those had to be the combination to bring that online piracy down.

Since you oversee global, is there another country that you feel has enacted some legislation or practice that the U.S. should adopt?

There’s still a lot of debates about it, so it’s not like anybody’s gotten it 100% right, but I think some of the transparency provisions in the EU AI directive, where people have to really be very transparent about what they use to train their models, that’s very important.

Is there any issue that that you wish you’d seen through to its conclusion that you won’t be able to at Sony?  

I want to see A&R people less afraid to talk about the advantages of a real label. We’re almost in this fight to the bottom of, “Let’s do the distribution deals,” and who could pay the most and have the shortest deal. First of all, I don’t think it’s good for the artists, and second of all, if everybody wants there to be continued investment in long-term artist development, you can’t do that with a short-term distribution deal. And, by the way, if you are a public company, what kind of asset value are you creating for your shareholders? You’re not!

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But you have The Orchard, which is a distribution company.

Yes, because The Orchard’s another alternative, but The Orchard is not more important than the frontline labels. We also have AWAL. The idea is to offer opportunities for artists wherever they may be at that moment. Meeting them where they are. But that doesn’t mean that it’s more important than the frontline labels and what they need to do over time, because if you think about it, our catalog is still the most important thing we have. It’s the reason we’ve spent billions of dollars over the last few years in acquiring catalogs, because of how important it is. The only way to build that catalog is long-term artist development.

What did you enjoy the most about running the Nashville office in between two Sony Nashville regimes in 2016?  

I love the fact that even the first day I was there, the artists came to the office. There was this relationship which made a huge difference. The artists would sit in some of these marketing meetings. There was not this distance between the label and the artist. When we started J Records, it was the same thing. Alicia Keys would hang out in my office; Swizz Beatz would hang out in my office. You have that relationship that makes a difference.

Who’s the artist you enjoyed working with the most over the years?  

When I was in working in Nashville, I loved working with Kenny Chesney. He was somebody that you could sit down and have a conversation with. Old Dominion has my heart.

You’re starting a new advisory services company that will help creative-focused ventures. What does that look like?

What I’ve loved the most in my job over the years is working with creative people. The dreamers. It could be producers, it could be entrepreneurs, it could be A&R people, it could be artists who have big ideas, but they’re not quite sure where to go next with that big idea. Somebody said this to me recently, and I like the way they described it: I want to provide the scaffolding for them.

When we started a couple of joint ventures, I would sit down with the person who we were going to do the deal with and [ask], “What is your goal? What does this look like in five years? Because once you tell me that, I can figure out what kind of deal we should do together.” That’s how I feel about this. “What is your dream? What does the goal line look like to you? Let’s figure out a plan over time, even figuring out the right kind of investment.” There’s lots of money going around, but you have to be careful about how much money you take because you have obligations to the people whose money you take. You don’t want to have 500 people the first day in overhead. People think that the more people they have, the more important they are. No. So it’s that kind of thing I want to do. I want to help people launch.

This interview has been edited for length and clarity.