At Work With Gwen Riley, Peloton’s Music Mastermind - Rolling Stone

Posted: 20 Nov 2020 08:53 AM PST

In Rolling Stone's series At Work, we go behind the curtain with decision-makers across the fast-changing music business — exploring a range of responsibilities, burgeoning ideas, advice for industry newcomers, and more. Read earlier interviews here.

Gwen Riley has partnered with the likes of 88rising, Mabel, Machel Montano, Wyclef, Common, The Grateful Dead, Lin-Manuel Miranda, the Prince estate, and her crown jewel, Beyoncé. But she doesn't work in the music industry — rather, in home exercise.

As head of music at Peloton, Riley thinks of herself as equal parts businessperson and storyteller. The New Hampshire native studied law at Boston College, but wanted to keep music at the center of her world — having grown up with a pianist mother and jazz-musician father — so she spent 10 years at Disney, where she led business affairs in the entertainment company's music department. Riley made the jump to Peloton last August and was promoted this year to senior vice president of music, responsible for drawing major artists to the fast-growing bike and exercise subscription company. (Disclosure here: I'm one of many who bought a bike when Covid-19 shut down gyms nationwide.)

Recently, Riley has taken great pride in offering artists a way to reach new audiences in a year that they can't tour. Peloton's membership more than doubled in the last fiscal year, rising from 1.4 million to 3.6 million in 2020 — and Riley, speaking with Rolling Stone from her home office in Los Angeles, explains how she's seizing this moment to launch as many new music projects as possible.

Let's talk about Beyoncé. How long did it take to turn the idea of that partnership into a reality?
It took over a year. This is obviously not lost on me: It was a very big deal. She is the most-requested artist on our platform and has been since 2016. And that's not just from our membership — it's also from our instructors.

We started thinking, "How can we partner up with her and do something really special, knowing that music is such a central part of the Peloton experience?" And then there was the fact that Beyoncé is a Peloton member. We approached her and there was interest.

The partnership really came together in the true spirit of collaboration. She recognizes the power that music has to engage and empower individuals as part of their wellness journeys. We thought, together, we could really start to elevate a conversation around health and fitness using music as the lever. This is just the kickoff for a multi-year partnership. And it started with a surprise drop — which is very Beyoncé — of the artist series. When we had conversations with Beyoncé around how critical a social impact component was to all of us, it crystallized around a creative concept to feature her "Homecoming" projects. It was an opportunity to celebrate and create dialogue around Black culture and music in partnership with HBCUs (Historically Black Colleges and Universities).

Beyoncé's Homecoming album became the focus of the first artist series that we've done with her. And that was beautiful because it tied into her love of the HBCU system and culture. There was a great through-line that just felt very organic and authentic to what we were doing and who she is. Having access to the dynamic live "Homecoming" music and documentary footage, which was featured prominently in our workouts and in our launch materials, was a career highlight. And we gave students at 10 HBCUs two-year digital memberships. It was very exciting.

Generally speaking, what does an average day look like for you? What are some of your reoccurring responsibilities?
Normally, my day starts at about 5 a.m. I wake up and run six miles. Then I sit down and start to get into a lot of meetings — obviously on Google Meet right now. I'm sort of my own satellite office. I do miss traveling quite a bit; before the pandemic, I traveled frequently and was in the New York office at least on a monthly basis.

I run the music department. We have three different divisions within it. There's a creative team that handles all of the day-to-day programming and the partnerships. We also have a whole deal vertical that's handling business affairs, legal, all of our deal-making, and all of our strategy around that. And then we have a big tech backend that we're running. We built the engine that houses all of our music. As we ingest, we're working on a whole feature side in the dashboard design that allows our instructors to program music directly from our database of songs, search for music, and more. Obviously, they also handle all of the backend reporting, the gating, and everything that goes on when you're managing a catalog of millions of songs.

So, I'm really overseeing everything, and making sure we're steering correctly and that all those different teams are working closely together like a well-functioning band; I like to think of it as a band. And I have to make sure that we're partnering well across the company with all of the different departments and divisions. It takes a thousand-person army for Peloton to do what it does — because we have a hardware sector, because we're product-based, because we're content-based, because we're membership-based. So a lot of my daily meetings surround the internal stakeholder material. But I'm also communicating externally with the entire music industry. That's everything from fielding inbound interest in the platform to going out and pitching new concepts, making sure that we're keeping up and keeping everybody abreast on where we're at and where we're headed.

You studied law in college. How did you end up in this kind of role?
Ironically, at the end of law school, I actually realized that what I really wanted to do was A&R and produce music. As you can imagine, it wasn't the most usual outcome for members of a law-school class. Literally the day after graduation, I ran to Manhattan and started to talk to everybody that would listen to me at record labels about being able to bring in some of the huge talent that I met at the Berklee School of Music.

Everyone was excited about it creatively, but the response that I would typically get was, "We can't hire somebody with a law degree to talk to artists and be able to explain to them the parameters of a recording agreement. There are people down the hall who work in business affairs and are going to work on the deals; you need to work there."

My first real career move was working at a film production company in New York City. I came in to support a music supervisor who was a friend of mine. I immediately realized that there was this amazing opportunity on the media side to build and shape essentially a record label inside of a film production company — where you could basically use feature films to produce a soundtrack. And if you got it right and had 12 to 15 tracks that cohesively meshed together and really made sense within a linear story that you were trying to tell from an audio perspective, you would be producing an album. All of a sudden, I was looking around going, "Wait a minute… I get to work with all the labels now, all the publishers and the managers in all of these genres. I don't have to pigeonhole myself. I can actually create records and build opportunities. All these people from Berklee who I was hoping to sign — now they're available to come in and create music as part of our film score. And we can set up a publishing company around that and start to own some of this IP."

It was an interesting combination of left brain and right brain. This was a burgeoning area in the Nineties. It was extremely challenging and fun. I got to stay involved creatively with what I loved and got to kind of start to shape a music licensing business around that and produce records and find a way to market and distribute this music on top of motion pictures.

That's what got me out to L.A. I moved over to Artisan Entertainment, which is now Lionsgate.

When you left Disney, what was it that attracted you to Peloton?
The interactive opportunity.

I transitioned to digital and started working in gaming at a Silicon Valley startup [Tapulous], which eventually did so well with our music game Tap Tap Revenge that it was acquired by Disney. So, through that acquisition, I landed in Disney's interactive studio. I got to touch all sorts of interactive projects, different types of new and emerging technologies, and really just fell in love with creating new music opportunities on evolving platforms. When you look at Peloton, you see what has been accomplished in a relatively short period of time — essentially, building a new interactive fitness category from scratch. That excited me.

All of a sudden, there was this idea of coming into an entirely new and territory — which reminded me of the burgeoning independent film years of the late Nineties, or the advent of the app store and the iPhone, which is when I entered into mobile gaming. It involved technology, a core community and membership that was highly engaged, and hardware; it was kind of a nice combination of everything that I sort of touched at Disney, but on a highly evolved platform.

And you've been exceptionally busy during these times of quarantines and lockdowns.
One of the things I was most proud of was, at the top of the lockdown, we were able to pivot really quickly and figure out a way offer digital subscriptions to people for a 90-day free trial. Just having that access to amazing content and workouts in a digital form that were accessible to everyone at no cost — it was a solution for gyms closing down and not being able to be outside as much anymore. A lot of new members came in. And different parts of the membership are growing — younger, more diverse, more people in the membership that are interested in different types of music.

And the artists really started to come in and say, "We notice what you're doing. This is kind of a new playground. What can we do? We're not able to tour anymore! Is there an opportunity for us to do something with the 3.6 million members on your platform and have a new way to distribute our music?"

Peloton became an interesting part of a digital solution to what a lot of artists have been struggling with. This is exciting because our membership is highly engaged and they're working out, really listening, and discovering music in a visceral way. It's not a passive experience. People call it a music-streaming platform, which we absolutely are, but it's interactive. You have instructors who'll take you on a guided tour of an artist's catalog. I can't think of any other standard DSP platform where not only can you jump into and re-experience an artist's catalog or discover a new one, but you have an instructor who's leading you through a workout and making the music come alive. They share stories of being fans and growing up with the music. They talk about interesting facts about the artist, things they remember from their music video, or any number of things that bring that personal connection. Marrying music, narrative, and visuals together with an elevated experiential workout is the future of workouts.

We've had the artist series since 2018, but it started to ramp up as the membership grew from maybe one artist series every four to six weeks to the cadence we're at now, which is every week. Also, first they started out being exclusive to the bike. Then we added the treadmill. And now, through the growth of our digital membership — in particular, the growth of yoga and strength — a lot of our artist series are multi-discipline. We know have more disciplines and spaces to plan. And through that, we're able to accommodate even more types of music. Just because one artist has a really up-tempo style, doesn't mean we can't do something with slow ballads and more sentimental or emotional pieces through yoga. Oftentimes, yoga or a complimentary discipline offers us the chance to show the B side of or softer side of a catalog — or maybe a harder, heavier side — that people haven't fully explored yet. It's not just the hits with us; we like to go deep.

In 2019, Peloton was sued by music publishers seeking hundreds of millions in damages in a copyright lawsuit. Given your legal background, were you hired to help patch this situation up?
Actually, no. I was hired very specifically to do artist partnerships. I was working on the other side of the table to elevate all of these creative opportunities and ramp up the ways we could take our content and express it on and off platform. That said, a big part of partnerships is not just about partnering with artists or management; it's partnerships with publishers and labels. I'm happy to say that we settled out, and that we're working very closely with the National Music Publishers' Association and all of the publishers who were involved to continue to create great programming on a daily basis. It started before my time and wasn't something I was directly involved in, but it's certainly something that's been nice to expand upon.

Would you say that the complications with publishers have been fully remedied?
Absolutely. And we're moving forward in lock step and partnering very closely with all of them.

What can music fans expect from the future of Peloton?
The vision is to continue to expand our brand — and a big part of our brand is music. There are going to more surprises to come. We'll continue to create different types of context experiences on our platform. So, you just have to keep tuning in and working out. We're just getting started, and the Beyoncé partnership was a great way to get us thinking about what's next.

I'm waiting for the day when there's a surprise album drop by an artist, but the you can only hear it on Peloton for the first day or so.
[Laughs] Keep riding that bike, Samantha!