MBW’s World’s Greatest Managers series profiles the best artist managers in the global business. Next up is Nick Bobetsky, manager of the biggest breakthrough artist of the past 12 months, Chappell Roan. World’s Greatest Managers is supported by Centtrip, a specialist in intelligent treasury, payments and foreign exchange – created with the music industry and its needs in mind.
Chappell Roan is one of those artists whose success isn’t just discussed in terms of its scale – it’s discussed in terms of its significance.
People aren’t only interested in what the hockey stick curve in streams and ticket sales makes ($$$$), they’re interested in what it means. There is much mention of ‘the zeitgeist’.
Rolling Stone recently called her The Future of Pop. Cynical old British (one-time) taste-making music mag the NME was far more restrained, ‘only’ calling her “the most exciting new pop star in the world right now”.
Some of these cuttings might well feature as motivational messages (aka warnings) on the walls of Atlantic Records, the label that dropped Roan in 2020.
That turned out to be a pivotal moment in her career, but it only happened because she’d begun redefining her own artistic journey.
Nick Bobetsky, who started managing Chappell shortly before the split, describes it as a time when she was “exiting phase one” of her growth.
He continues: “When an artist makes a real change like that, it can be hard for an existing partner to completely defer to the artist.
“They should, we all should, but when you have certain expectations of an artist, and that artist pivots, not everyone can understand that change is important – and that’s what happened with that relationship.
“Don’t get me wrong, it was hard for her to get dropped. But the reality was a focus on what to do next.”
“It’s difficult for everyone when an artist is still defining themselves – but it’s important to remember that it’s hardest for the artist. I think Atlantic really believed in her by the time that they parted ways, but I also know that she was ready, we were ready, to make that change. And ultimately Atlantic agreed that they weren’t the right fit. Don’t get me wrong, it was hard for her to get dropped. But [it led to] a focus on what to do next.”
And what she did next was pretty spectacular. Following a series of independently released singles, Roan signed a deal withIsland via Amusement Records, the label founded by her long-term writing partner, Daniel Nigro.
Her debut album, The Rise and Fall of a Midwest Princess, was released in September 2023, but only last week reached its peak position (so far) on the Billboard 200 chart at No. 2.
It’s a similar slow-burn story in the UK where the record didn’t chart until April this year (at 68) before hitting No.1 at the start of August.
Its ascent was helped by a support slot on Olivia Rodrigo’s Guts World tour; a standout, much-shared performance on The Tonight Show; Good Luck Babe, the first post-album single, currently in the Top 10 in the US and UK; and a Lollapalooza appearance in early August that organizers believe attracted a record crowd.
Bobetsky recalls that he and his team were in tears after that show, reflecting on how far they’ve come with their star client and, surely, awestruck by where this might lead.
Bobetsky began his career at soundtrack-specialist label Milan Records, but eventually realized that “my passion was to be as close to the artist as possible, connected to all aspects of their career – as much a partner as I could be. And that meant management.”
He left Milan and managed a couple of bands on his own before becoming part of Red Light Management’s roster.
In 2019 he moved on again, this time to join his friends Marc Jordan and Ian McEvily at Rebel One (now State of the Art). Looking back on the switch, he says: “For me it was about really focusing on artists that were excited to scale to a level that has cultural relevance and impact. Marc in particular taught and encouraged me to think bigger, and to find artists who wanted to make big statements.”
Coincidentally, he had just met a client who would be a perfect match for this new philosophy…
How did you first meet Chappell and what were your impressions?
Her then-label, Atlantic, sent me some music and said she had parted ways with her management. What I saw, straight away, was already a next-level talent, and a level of confidence, even at that stage of her career, that was truly remarkable.
“She was still only 19, but it was clear to me that Chappell was going to be an artist that really mattered for a long time.”
She had a conviction about who she was that was unshakeable. She’s wired in such a way that when you meet her, you realize, she’s just got it. She was still only 19, but it was clear to me that Chappell was going to be an artist that really mattered for a long time.
Why do you think you two clicked?
What I will say is that she had gone through experiences that weren’t advantageous to a young artist finding themselves.
I am just generally really supportive in helping artists find their way, rather than shifting their direction according to my or anyone else’s agenda.
I don’t pretend to ever know where it’s going to go [for any artist], I just support their personal and creative journey, and their artistry. I’d like to think that that’s what resonated with her, because I don’t think she had that.
Chappell was still with Atlantic when she signed up with you. So, how did that relationship come to an end and how did that change things?
She ended up making Pink Pony Club, California and Love Me Anyway [all 2020], writing with Daniel Nigro at that time.
By then, I think she was really clear in what she wanted Chappell Roan to be. And that was actually a pretty remarkable shift from her first era; that’s what precipitated the parting of the ways.
“there are two very different paths when an artist gets dropped: one is that they’re deflated and destroyed because they put so much weight on the fact that they were with a major label; the other is that they’re inspired by knowing that they now truly hold the reins… Chappell obviously took that second path.”
Like any artist, there’s a level of self-doubt in a situation like that. But there are two very different paths when an artist gets dropped: one is that they’re deflated and destroyed because they put so much weight on the fact that they were with a major label; the other is that they’re inspired by knowing that they now truly hold the reins, there is no one telling them what they should or shouldn’t do.
Chappell obviously took that second path and thrived independently.
How did you go about making the new situation work for you?
I set up a distribution deal for her. She continued to make great music, and we just focused on building it, releasing singles independently.
We weren’t leveraging, I wasn’t working the DSPs – we didn’t bring on a publicist until the end of 2022. Maybe because of that, the fans were getting louder and louder, they felt real ownership. And that in turn meant we were getting more and more press interest. Something was going on.
Chappell’s always been really big on her community, and really open about what she’s going through and what she’s feeling; that resonates.
“With every decision, if it’s not 100% yes, then it’s no. So we passed on some really high-profile support tours, we passed on some early record deal offers – and then we came to the point when there were a lot of labels circling.”
I’ve said it before, but she has the 100% rule. With every decision, if it’s not 100% yes, then it’s no. So we passed on some really high-profile support tours, we passed on some early record deal offers – and then we came to the point when there were a lot of labels circling.
But even then, there was a real commitment: if we didn’t find the right partner and a fair deal, we wouldn’t sign any deal; we’d just keep building.
Thankfully, we found Island. It was a really special connection, and they’ve proven to be really great partners, supporting her vision in every way.
If we hadn’t found them, there were plenty of other suitors, other majors, the biggest indies, but I know 100% that she would have walked if they didn’t check those boxes.
What was it about Island that persuaded you both to sign?
In all the meetings she took with the labels, she asked a lot of questions, she pushed them. She was interviewing them more than anything, taking them to task on how happy their employees are, how they operate etc. She went way deeper than, ‘How can you help build my career?’
She was really open with people about how she operates and her core values.
“She was interviewing them more than anything, taking them to task on how happy their employees are, how they operate.”
Island did a really good job of giving her a very honest representation of how they’re wired. I think Justin [Eshak] and Imran [Majid, co-CEOs of Island] are running a really different kind of company.
Because company culture comes from the top, I think everyone at Island is very real, very honest, very passionate and driven, which is rare with labels. Both of us saw that and felt that.
When it came to Midwest Princess, what were the creative goals and what were the commercial expectations?
By the time we released it we’d put out, I don’t know, six singles. So it felt like the arrival of something bigger for her. It felt like a huge step but also a continuation.
I mean, even now, daily, we’re seeing new peaks pretty much exactly a year out from release. And we’ve got six tracks in the Billboard Hot 100.
In truth, the album was about continuing to do what we’ve always done, and that’s to have a very clear focus on the world of Chappell Roan.
I’m sure the labels had specific projections, but for us that wasn’t a priority. We all loved the album. She was really proud of it. We released it and continued to grow it. That’s it.
For us it all really reflects that Chappell is more than one moment, more than one song. There’s this inclusive artist that people are coming together to celebrate and be part of.
Why do you think Chapell has connected so strongly with such a big audience at this time?
She was always really focused on what was important to her. She was always very vocal that her shows were safe spaces for queer kids, for example.
We’re not stretching things too thin; we’re not doing a load of collaborations. The word ‘marketing’ in the world of Chappell Roan means something really different than it does to a lot of artists right now.
She’s not an artist who’s been driven by, ‘How loud can this moment be? How do I reach more people?’ That doesn’t come into it for her. People feel that, which means they feel part of the success, not separate from it – or from her.
“The word ‘marketing’ in the world of Chappell Roan means something really different than it does to a lot of artists right now.”
The success hasn’t taken her away from her core fans, she’s taken them with her; they are part of it.
That’s why Lollapalooza was so impactful, because everybody was ready for it and everybody celebrated it, together with Roan. That’s powerful – and infectious.
And it’s part of our core strategy. It’s not ‘Let’s do everything, let’s maximize every ounce of the success that’s currently happening’; that’s not the point.
What can you tell us about new music on the way?
She’s busy writing. I do think that we’re likely going to embrace a very similar plan that we did for this album, which is that when she finishes a song she loves, we put our heads together and quickly work to get that music out. That’s what we did with Good Luck Babe.
Where does a new album fit into that strategy? Do you guys still believe in the album as a standalone art form?
Chappell Roan is absolutely an album artist. I think that’s what people want from her, big picture. I don’t think that takes away from the impact of singles.
It’s partly a question of when the fans are asking for an album, and we have a lot of insight into that sort of thing.
There are arguments to be had about how you build an album out these days. Sometimes putting a record out with no lead-up singles can be very impactful.
I think right now Chappell wants to feel free to put music out when it’s ready and when she’s excited about letting people hear it. And I think that’s what the fans want as well.
Do you have any insight as to why she writes so well with Daniel Nigro, who is also part of the State of the Art Family, managed by Ian [McEvily]?
It’s a very special creative connection. There are other collaborators that come into their orbit, but what they have is something that I think everyone yearns for.
They really respect each, they really push each other. I have never seen her finish a song that she’s not really, really excited about.
Chappell is ruthless in that she is incapable of embracing something that she doesn’t feel exactly right about creatively. She never compromises. And Daniel sees eye-to-eye on that.
In your view, What are the most important skills and qualities an artist manager needs to have?
The biggest contribution a manager can make is being skilled and committed to what makes the artist great. And that’s the human stuff, the creative stuff, the things that define them.
If a manager can be a partner in that process, that’s the biggest value they can bring – to an artist at any level. And every artist is ever-changing, or at least the best of them are, so as a manager that’s an ongoing process.
“I think that there is an art to management that goes much deeper, that goes beyond business.”
The deal-making, the relationships, the strategy, you have to be good at that as well, and I think smart people can generally learn those things.
But there is an art, truly an art, to management that goes much deeper, that goes beyond business.
It’s about the artist proposition. What is this artist better at than everyone else? What is true for them as an artist? How do I advocate for all of that?
It all needs to come from their identity, one that is real and one that they are committed to exposing, because having a strong sense of self is one thing, but showing that to the world…
Artistry is a human matter, not a career matter, not a business or professional matter; it’s human.
If you could change one thing about the music industry right now, what would it be?
[Making] ticket scalping illegal in the US, as it should be. The secondary market is one of the biggest evils in this industry, and it’s avoidable if the government would step up.
It’s a shame that the scalpers have the most money to spend on lobbying and influence in Washington.
“It’s really out of line that there aren’t policies in place to combat such a clearly egregious and predatory infrastructure.”
For me, it’s not even about the artists making more money, it’s about their relationship with their fans – which is something that is now at the core of our industry.
It’s really out of line that there aren’t policies in place to combat such a clearly egregious and predatory infrastructure.
What advice would you give to a young manager just starting out?
Learn all of the business parts so that you know how to operate at a high level when it comes to deal-making, strategy, a global perspective, all that. And then you can get into the really important stuff, which is sharing the passion of an artist and being a true partner to an artist.
There’s nothing better than being able to be a real partner in their lives. It’s inspiring and it’s important.
I really believe that you can manage differently today.
What do you mean by that?
I think the old guard were connectors, they would use leverage, they would do deals and they would be driving things. They would control and they would manipulate. But that day is over.
I know that doesn’t apply to all managers in previous eras; I’m talking more about a general trend.
Now, you don’t have to operate out of fear. The best managers today are those who are really good at building things and being partners and advocates for their artist.
