Northleaf Capital Partners will raise $303.8 million through the sale of bonds backed by music royalties of The Who’s Pete Townshend, country star Tim McGraw and other artists in Spirit Music Group’s wide-ranging collection of music rights.

The bonds will be backed by over 52,000 assets, primarily compositions but also recordings, that represent a sub-section of Spirit catalog, according to Ross Cameron, a partner at Lyric Capital Group, a private equity firm and Spirit’s financial sponsor. The sale is a “joint effort” of Northleaf and Lyric that provides “a replacement” for another debt facility, says Cameron, who co-founded Lyric in 2019 with managing partner Jon Singer, Spirit’s former CEO and current chairman.

The partnership with Northleaf, which invested $500 million in Lyric in October, “puts Spirit Music Group in a position to continue to do what they do best — service the writer community [and] be an independent publisher,” says Cameron. Lyric’s management-led buyout of Spirit used $350 million, including $280 million in equity by the Morgan Stanley Alternative Investment Partners, to recapitalize the company.

While some publishing investors have sold equity in recent years to build war chests, the concept of securitizing music assets — selling bonds backed by music royalties — gained stature in 1997 when investment banker David Pullman sold David Bowie raised $55 million selling 10-year bonds backed by David Bowie’s publishing and master recording royalties. Pullman went on to sell bonds backed by the publishing assets of James Brown, the Isley Brothers, Ashford & Simpson, and the Holland-Dozier-Holland songwriting catalog. Bowie didn’t have great timing, though: U.S. recorded music revenues peaked in 2001, leading ratings agencies to downgrade the bonds, although they were paid off on schedule in 2007.

Northleaf’s bonds, which will carry an investment-grade A rating by Kroll Bond Rating Agency, should appeal to investors who increasingly see music royalties as safe and recession-proof assets. In just the last four years, independent companies such as Spirit, Hipgnosis Songs Fund, Concord Music Group, Round Hill Music and Primary Wave Music have raised and spent billions of dollars on primarily publishing rights. The major music companies, too, are snapping up songwriting and recording catalogs by the likes of Bob Dylan (Universal Music Publishing for between $375 and $400 million), Paul Simon (Sony Music Publishing for an undisclosed sum) and Bruce Springsteen (Sony Music for more than $500 million).

In its 26-year history, Spirit has amassed a catalog of over 100,000 songs, including 800 hits, featuring rocker Billy Squier (“The Stroke,” “Lonely is the Night”), jazz great Charles Mingus, T. Rex (“Get It On (Bang a Gong)”), James William Guercio (producer of albums by Chicago and Blood, Sweat & Tears), Graham Nash (of The Hollies and Crosby, Stills and Nash) and composer Henry Mancini (“Moon River,” “The Pink Panther Theme”). In the last two years, Spirit acquired the songwriting catalogs of Kara DidGuardi (hits by Pink!, Katy Perry and Carrie Underwood) and Ingrid Michaelson (“The Way I Am” and “Girls Chase Boys”) as well as some of McGraw’s master recordings.

[Spoiler alert: This story contains the identity of the winner of Wednesday night’s (Dec. 15) season six finale of The Masked Singer.] 

The sixth season of The Masked Singer was a wild ride, with the usual complement of legendary singers (Toni Braxton, Ruth Pointer, Natasha Bedingfield, Todrick Hall, Faith Evans) mixed in with TV personalities and comedians (Bobby Berk, Honey Boo Boo/Mama June, Rob Schneider, Larry the Cable Guy, Willie Robertson) and the left-field outliers, including punk icon Johnny Rotten, composer David Foster and his wife Katharine McPhee, rapper Tyga and NBA legend Dwight Howard.

But when it came down to it, it was clear the shiniest gem in the bunch — the glittery Queen of Hearts — was destined to take the season 6 crown over the formidable Bull. The Queen left nothing to chance, blasting out of the gate with a cover of Lady Gaga’s “Born This Way,” followed by Edith Piaf’s “La Vie En Rose,” then Bishop Briggs’ churning “River,” Sia’s “Bird Set Free,” Patsy Cline “She’s Got You” and a titanic duet with judge Nicole Scherzinger on Aerosmith’s “Dream On.”

The lid was slammed shut on Wednesday night’s finale, where she crushed an unplugged version of Marvin Gaye’s “What’s Going On” featuring her signature yodel and a high-energy run through Katy Perry’s “Firework.” With a clearly well-honed voice inside the sparkly, winking head, the judge’s guesses mainly focused on pop icons such as Miley, Gaga, Katy, Britney and Christina, as well as Kellie Pickler and always-wrong judge Ken Jeong’s suggestion that it might be Miranda Lambert or actress Renée Zellweger. There were a few other left-field guesses as well, roping in actresses Ashley Judd and Helena Bonham Carter.

But when the glitter settled, it was no surprise that the diamond in the rough was none other than Grammy winner Jewel. Billboard spoke to the singer before Wednesday’s finale to find out how the TV-less star ended up on the show, how advice from Bob Dylan and Neil Young helped her make such left-field choices, and what we can expect from her in 2022.

How does Jewel end up on The Masked Singer in 2021?

It’s not a very sexy answer, but it’s an honest answer: I am a mom and I’m a single mom, and this business is not very kind to women that become parents. One is because the physical nature of the job, we have to tour and be away on the road and it’s hard for a mom because kids need stability and they need to be in school… I love art, obviously, but my job and my commitment to having a child is that I’ll be a present and engaged mom, so I’ve looked for opportunities that let me check a lot of boxes. The first one has to be it can’t take too much time from my son’s life. I obviously needed to raise my profile if I was going to do it and promote new music and the third box is it has to be creatively fun and interesting for me. So the Masked Singer, I know it sounds odd, but it was a great fit for me for all those reasons. We shot it pretty quickly, it’s a really high-profile show and it let me focus on something that I’ve never been able to focus on the entire 25 years of my career: just showing my technical ability.

You have such a distinctive voice — for the record, I could tell it was you right away — but it seemed like sometimes you tried to tweak it, such as on the Lady Gaga cover, as well as busting out a Southern accent when speaking to the judges. Were you purposely trying to throw the panel and audience off?

Yeah, I definitely did. The tricky thing with the show is I think you have to really be authentic and sincere and you also have to throw people off. So I tried to choose things that were a little more superficial while still offering people a sincere experience of myself. So getting to change my vocal tone a little bit –really just emulating the singers — being a bit more Lady Gaga in tone or Patsy Cline in tone, because that’s how I taught myself to sing by imitating Ella Fitzgerald, Sarah Vaughn, Tracy Chapman and learning to control my voice in different ways. But I do think if you game the show too much nothing rings as sincere or authentic. People can’t read your face and read facial expressions and connect to you, so I think you have to give people something sincere to connect to and then have fun with tweaking everything else.

You opened pretty strong with Edith Piaf’s “La Vie En Rose,” which really threw down the gauntlet. Does that song have special meaning to you?

Like I said, one of the attractive things about the show was to focus on my technical abilities. I grew up listening to Edith Piaf, I find her heroic, I find her singing heroic, I find her writing heroic — she wrote “La Vie En Rose”! — and that song is still… my 10-year-old son heard it and said, “wow!” He doesn’t speak French and he doesn’t know who Edith Piaf is. I grew up worshipping the song and I knew it would scare the bejesus out of me to perform it, especially since I don’t know French. But it’s why I did the show, I wanted to challenge myself vocally and it was kind of liberating not to have to write the song, but just pick songs that I loved vocally or how they were written.

Were you already watching the show?

I don’t have a TV, so we don’t watch a lot of TV. I’ve been aware of it, but my son and I haven’t followed it.

Some of the clues were pretty obvious — tea party images from Alice in Wonderland that alluded to your 2006 album, Goodbye Alice in Wonderland — but were we supposed to know Hilary Swank has a dog named Jewel? Is that common knowledge?

[Laughs] I didn’t even know that and I’m friends with her. No, I didn’t think that was common knowledge, but they are always trying to throw people off because I would think it would be so easy to guess me. My fans were 1000% locked in on first breath I think.

The guesses ranged from Miley Cyrus to Lady Gaga, Ashely Judd, Katy Perry, Britney Spears, Christina Aguilera and Helena Bonham Carter. Were you Flattered? Shocked? Annoyed?

I like the range of the guesses. Bob Dylan mentored me when I was young, [as did] Neil Young… to take the risks creatively that you want to take, no matter the consequences. Follow your heart and your muse, so I’ve done everything from pop to country and dance… it’s funny, people just don’t like singer/songwriters to branch outside of the genre… but I love every genre and it’s’ really sincere so for me doing this show it was a no brainier that want I wanted to cover everything from current pop to 1930s music and classic country. I like that that was reflected in the guesses.

To be fair, your costume was kind of Jewel-shaped, so it wasn’t that hard a guess. The costumes are famously cumbersome and hot, but yours seemed especially unwieldy and top-heavy. What was the hardest part of maneuvering in it?

First of all, designing the costume was fun. I’m a visual artist and I don’t ever show my work, but I was working on a sculpture of a heart that’s breaking open and it had this eye with a star and a light shining out of it. So when I decided to do the show I wanted to build a costume based on this one-eyed heart design [and] I drew this little sketch of the costume… but it didn’t dawn on me how top-heavy it would be. It wasn’t too bad, but the part that was difficult was visibility: I couldn’t see for 20 feet in front of me and I could only see from the bridge of my nose up. I could see the hair of the judges, or the back wall of the studio, but I couldn’t see the edge of the stage, I couldn’t tell where the center of anything was. They had to put up a light high up on the wall at the back of the studio so I could center myself.

You mostly covered songs by women, but that duet you did with [judge] Nicole [Scherzinger] on Aerosmith’s “Dream On” really showed off your rock side. You guys really had a high note-off in there. Why that song for the duet?

I think Nicole wanted to serve the drama as much as I did. You’re always looking for songs that show range and start somewhere different than where they end up. We both just love that song, it’s vocally challenging and well-written and she’s a great singer. I just really wanted her to have a great moment and shine and I feel like she did. She looked amazing and she sang great. The thing I’m most proud of in the duet is singing harmony with a brand new person is hard. Because you have to feel each other and once you do your harmonies become in synch. So not ever having sung with her, not being anywhere near her, being in a costume and you only get one run-through earlier in the day… for me the ending notes of the song, where she’s going out of time and I’m harmonizing with her is my favorite part of that song.

Also, your Sia cover made her weep like a baby. That one felt especially emotional. Was there more to that choice that met the eye?

I’m a huge Sia fan. I love that song. It’s definitely a song I feel I could have written, or wish I’d written and it feels so personal to my life as anyone who’s read my autobiography [Never Broken] that song… it felt like I was singing about my own life. I think that’s a song a lot of people can relate to, how we make ourselves small or don’t speak up and use our voice. And when you finally find your voice it’s so empowering and that song typifies it. It was super emotional for me and it’s amazing that in a minute and  a half I could sing a song in a costume that nobody can see me in a dark audience and that people could cry. Music’s so powerful… music has always been my own healing and I’m honored that it moves people in that same was as it does me.

You don’t come off as super-competitive, but did your really, really want to, or expect to win?

Definitely. The problem is that this isn’t like a race with a finish line where there’s a literal linear winner. It’s art and it’s super subjective and obviously I’m not more talented than David Foster or Todrick, but my whole career’s that way. As an artist you have to get really comfortable that success is outside of your control… So all you can do is focus on, “how am I doing, what am I offering?” The show is a great example of that: I never knew who else was singing, I didn’t know what songs they were doing, whether they could dance, so I caused me to hyper-focus on “what do I want to get out of the show? How can I be authentically myself and connect with people through costume? How much heart can I bring?” That’s really all I focused on.

Tell me about the Queen of Hearts covers EP you’re dropping tonight that includes all the covers from the show?

I just loved singing these songs and I worked hard on the arrangements and really poured my heart into them. Once I was done I was like, “aw, I worked hard on this and I want these songs to live on!” And I knew my fans would want them.

And you have a new album and tour next year?

It’s called Freewheelin’ Woman. It comes out pretty soon and I’ll be touring next summer. The goal was to challenge myself as a writer to write bigger melodies to show my vocals more and show a new style of my singing. It’s kind of a Muscle Shoals pop album and it was produced by Butch Walker.