Jonathan Gray on Building the Encore app, democratizing the music industry, and working with kid cudi

Credit: Encore

Credit: Encore

There’s a new music streaming app available for musicians to cash in on their music without breaking a sweat — and it’s all thanks to a tech mogul, a Hollywood director, and a famous rapper. JonATHAN Gray, Ian Edelman, and Scott Mescudi, better known as Kid Cudi, joined forces with the same mission in mind and heart; to “democratize the music industry” for young and inexperienced musicians looking to break into the business.  

I learned a lot about the CEO of the Encore app during my conversation with him, a man who used the management and leadership skills he gained at Facebook for his businesses, including this new music app. In the interview, Gray outlined his journey for building himself as a sought-after tech expert, selling his startup company, ‘Cask Data’ to Google and watching the phenomenal rise of Facebook, and how Edelman convinced him to join Encore after three months. 

Jonathan Gray, CEO of Encore. Credit: Encore

Gray is a Los Angeles-born and raised tech entrepreneur. The husband and father of two is a self-proclaimed ‘Hip-Hop Head,’ intending to aid musicians who are being underpaid by their labels with the help of Edelman and Mescudi. Gray, a college graduate with a degree in computer engineering, shared that before becoming an engineer for Facebook, he hated the idea of the site, which at the time was a college-only platform. And as a result of that contempt, he and a roommate started his first startup company, “Streamy.com.

When I was an undergrad, Facebook came out as a college-only platform, and I hated it. Because it was like—I called it “the social stocking” because there was no news feed,” Gray said. “So all you could do is check everyone’s profile to see their relationship status. And I was like, ‘what are we doing?’ And so, a friend of mine and I were roommates; we started this company my senior year called streamy.com.” 

Gray called the web 2.0 era-based website the “bootstrap painful experience in your early-mid 20s” point in his post-college career, noting that it was an amazing experience. We built like incredible [and] cool stuff, way ahead of its time, but we did not make it. And that kind of crash— of 2008 and 2009 [sic] was kind of the nail in our coffin, and that led me to Facebook.” When the tech genius first joined the company, only 200 engineers worked on the website. A couple of years after joining Mark Zuckerberg’s social network, Gray was an eyewitness to the company’s growth and expansion after employing more than 2,000 engineers. 

So I was kind of—I just kind of joined right before its inevitability. It was big; there were hundreds of millions of users, but there was still competition,” Gray stated. “And it was not what it kind of became shortly thereafter. And so it was insane and amazing and really, really changed.” Gray would learn a lot as a part of the brand, applying his new skills to hiring people, guiding them to zero in on their energies, and “empowering them to do their best work ever.”  

He recalled a time at Facebook when employees became “wildly focused” on a single project through a method called lockdown. 

They had this thing there called lockdown. One of the coolest things in the world, and it’s something that they had from the very, very early days,” Gray remarked. “Which was—some huge target, ‘everyone, stop what you’re doing. This is the only thing that matters.’ We’re all going to put our weight behind this thing. And in their early days, that was like, ‘oh, we’re going to launch in a new campus. We’re going to launch in a new country until we win that market. No one does anything else.'” 

Additionally, Gray recounted the moment when Google released Google+ and how Facebook locked down to replicate the features of Google’s new social media platform.  

We went into a Google+ lockdown because Google+ launched and said, ‘oh, we have circles.’ And they had they Like these three features that were supposed to make them different from Facebook,” Gray explained to me. “Zuck put the company into a lockdown. [So] We all built those three features and in three weeks had feature parity with Google+.” 

Despite feeling like Facebook has lost its way in certain aspects, Gray said he wouldn’t take anything away from his time spent there, saying that it allowed him to become a “ten times better Founder/CEO.” After leaving Facebook, Gray started Cask Data, the “complete opposite” of Facebook. 

My next company, what I did was a lot of what I did at Facebook, [which was] build —kind of like these big data, back ends at the level of scale of Facebook. And we were inventing a lot of technologies,” Gray said. “But those technologies were only really used by the “Googles” and “Facebooks” and “Twitters” of the world. And so I started this company, Cask, to basically say, ‘how do we take all of these new innovations that these internet companies have made, but bring them to banks and telcos and health insurance companies and all these large Enterprises that are like 20 years behind in terms of where the internet companies are?’ And so Cask was really about bringing a lot of the things that Facebook does in the world and bringing it to traditional enterprise companies.” 

Gray, however, did not have the vision and purpose needed to propel a company of that magnitude, so in 2018, he sold the company to Google for an unspecified amount, mentioning his burnout and resistance to building any more startups. 

“The whole kind of company, the product and engineering teams went to Google. And I came out and said, ‘you know, I don’t think I’m gonna start another company again,’— that kind of burn me out,” Gray divulged. “And so instead, you know, what, I really love to do is help people. And so I started this thing called the startup lab and basically just helped other entrepreneurs get companies started.”  

During this time, Gray met Edelman, a director, screenwriter, and the President of Encore, who approached him with the original concept of the app. Grey explained how he went from helping Edelman crowdfund the app to being introduced to Kid Cudi and finally working on it before Covid. 

Ian Edelman, President of Encore and Scott Mescudi, COO of Encore. Credit: Encore

“And so I met Ian Edelman, who’s the person who originally came up with the concept. He’s, you know, the creator of ‘How to Make It in America.’ He gave [Kid] Cudi his first acting gig back then before Cudi had made it. And so, Ian and Cudi go back to before either of them had kind of made it. And so that’s a really long kind of standing relationship,” Gray said. “But Ian had this idea, and for a year, I was helping him just as an advisor. And so we were building decks, and helping him raise some money and kind of figuring out, kind of some of the product ideas, coming up with the 10-cent clap.”

As the trio was getting excited about their new project, a worldwide pandemic broke out. Despite its impact on the tempo of the process, the trio continued with the new endeavor. 

 “A lot of that stuff happened in these really early days of just me and him jamming on a whiteboard in my office. And then comes Covid. And, you know, basically, the entire initial idea pre-Covid was artists had to give away their art for free all day on Instagram,” Gray explained. “And so I basically told him [Ian] ‘hey, you need to do this all the way now, quit everything you’re doing in Hollywood. Jump into this company,’ and then he said ‘do it with me’ and after like three months I gave in and decided to do it with them.”

In the three months leading up to his joining the company, the three men discussed the idea with people in the music industry, validating it and verifying its value. Yet Edelman was also working on a collaboration with Cudi called “Entergalactic.”  

“At the same time, Ian was in the middle of making a movie with Cudi, “Entergalactic,” which is coming out this year. And so they were talking, and then the three of us got to talking,” Gray stated. “you know, that kind of became the founding team. And so, you know, the three of us were the original three founders; all equal Partners in the business.” 

Gray told me that he believes that the fact that they are from different walks of life and have different careers is fundamental to their company’s success. In contrast, most music-oriented apps are either founded by musicians or technology enthusiasts; Encore is a balance of both. 

 “We have a founding team that straddles these two worlds completely. Cudi is an artist’s artist. He is not a capitalist, entrepreneur, businessman. He is amazing and completely different from me in almost every way. And, you know, I come at it a very different way, and Ian sits somewhere in the middle,” Gray affirms. “And I think that’s really a huge part of the strength is, you know, the ideas that we have. The strategy that we have is very much my technical and product design-oriented way of thinking about consumer apps and thinking about, you know, the technology side of stuff.” 

“And, you know, every young artist that we work with, they all know and respect Cudi infinitely. And so it’s, you know, another reason why he was really just the perfect partner for us. Because he does really commend that kind of respect because he is truly authentic, and I think artists love artists that put out different albums, and some shit great and some shit slightly different.”

Jonathan gray on younger artists looking up to Kid cudi

Gray discussed Kid Cudi highly in our conversation, revealing that he was a pivotal part of the conception and direction of the app. “Cudi, He’s coming at it from an artist perspective and not a technology perspective at all. And, you know, he was really instrumental in kind of a lot of the original vision and the direction that we ended up going,” Gray explained. 

Grey compared Encore to the social media site Myspace, where Kid Cudi was discovered, as a new way of finding unknown musicians. Although most musicians upload their music on different streaming services like Spotify, he clarified that it is difficult for artists to be discovered because of their controlled playlists. 

“You can’t be discovered on Spotify— [there’s] 75,000 tracks a day. The playlists are controlled in the same way that radio is controlled. And so, it’s really, really hard for new artists to be discovered. And a lot of the game today is it’s all won and lost on social,” Gray described. “And socials—not really that much about art and music. It’s much more about persona and kind of virality and memes and a whole different category of stuff that is in many ways, a departure from art.” 

I sense Gray was very passionate about differentiating Encore from other music apps, creating a new frontier for musicians, and establishing different expectations for them. We discussed the difficulties artists face as they manage their social media accounts, hope to get enough streams, and even sell merchandise to stay afloat. 

“And the thing I told Ian when I first met him, the thing that excites me the most is it incentivizes artists to create art. And so we are, we can be responsible for more art in the world.”

jonathan gray on wanting to encourage artists to create art.

And so a lot of what we’re trying to do is, have a different space, right? Have a different set of expectations. Have a different vibe about the kind of content, the kind of interactions, the kind of experiences [sic] that you can have. [But that] doesn’t mean that there isn’t a place for Instagram and TikTok—there’s a place for Spotify and Apple music, those are other things,” Gray said. “The way that we look at it is; number one, an artist has to give away their time on social, to hope to get enough followers, to hope to catch enough streams, to hope to maybe scratch by and maybe then, sell merch and go on tour and get some brand deals and then actually make a living.

According to Gray, if you have “real engaged fans,” making money shouldn’t be too tricky, primarily if you use Creator platforms, such as Twitch, Patreon, and Onlyfans, that direct fans to creators. Unfortunately, platforms like such haven’t been very profitable for musicians, and consider them the “forgotten creator.” 

“Like they’re still stuck in the same business model, [doing] the exact same things for years after years. Nothing has really changed for music artists. There is this new land like, ‘oh, you can get Tik Tok viral hits and all this kind of stuff, but I think that is as good as it is with the music injury. It’s probably just as bad for the music industry. I think it’s a complicated thing,” Gray said. “I think you know, I think about it as kind of the Memeification of music. You know, it’s really reducing something that is art to viral loops, memes, sexual innuendo, and things that certainly a ‘Cudi’ is not about.”

In Gray’s opinion, Tik Tok has been successful for some artists, but the “Tik Tok-going-viral” model is not a one-size-fits-all approach, even though it’s what labels are looking for these days. However, some musicians would rather provide an experience than a viral moment.  

 “I would never take anything away from artists on Tik Tok at all, but the notion that what’s happened is like the whole record industry, and everyone is completely focused on that now. And you know, we deal with artists all the time who, you know, are leaving their labels because the labels just want to have them throw shit up against the wall on Tik Tok to go viral. They want to build albums. They want to build an experience. They want to have relationships with their actual real fans,” Gray clarified. 

Gray believes that the music industry lacks a lane dedicated to art, performance, and interaction between fans and artists. For most musicians, performing and making music is their full-time job and their primary source of income. According to Gray, musicians often find it challenging to develop content and work on their art. 

And, you know, a lot of how we think about is like, well, how do you fit this into an artist’s life? A lot of the Creator platforms [are] out there—they’re full-time jobs. If you want to be a Twitch streamer, that’s your full-time job,” Gray explained. “And then to be like, okay, you gotta do all that shit, and you have to live an interesting life, so you have something to talk about, and then you got to sit at your computer for five hours a day, every day just to be able to make money from your fans, you know, it’s really really a tough situation.”

He explained the thought process when creating the app while aiming to solve common problems facing musicians today. 

“Okay, well, how can you actually do it so that they can do interactive engaging, other performances or other types of experiences with their fans in a way that’s as accessible as Tik Tok and Instagram? It’s just on your phone. It’s with you everywhere you go,” Gray clarified. “Except it’s really built around music. It’s really built around performance. And so, without a budget, how can you create something that’s still visually interesting? How can you create something that’s really personal to you? So that I can have my own mood set, I can have my own art so that I can have my own environment versus like I’m using the same face filter as everyone else on Instagram.”

While talking, Gray and I got into the nitty-gritty of the app and how they make sure to give a fair share of the money to their participating music artists. Gray informed me that the gaming industry and the free-to-play component of mobile games influence the app the most, disclosing that the “in-app purchases model” has been very successful in the gaming industry as well. 

Every [Encore] show costs ten cents. What’s amazing about a 10 cent show is it actually sounds cheap when you compare it; when you compare it to what a YouTube view gives you or what a Spotify stream gives you, it’s a hundred times better. And so it seems really cheap,” said Gray. “However, it’s way better monetization than everything else that artists are doing today on a per-user basis. And then with the gamification, those game mechanics, obviously people clap way more than one time.” 

According to him, the 10-cent claps are beneficial for artists because even though it appears cheap, fans want access to their favorite artists, the notoriety that comes from it, and higher rankings on the leadership boards, and with that in mind, they are willing to spend money to achieve that. 

“It’s because there’s a set of power users and super fans that pays a lot because they want access, they want credibility, they want notoriety in their community, they want shoutouts, they wanted to talk to the artist. All those types of things get people to want to be up on that leaderboard, get people to want to get closer and closer to the artist. And so it’s an interesting balance,” Gray explains why the “10 cent clap” is successful for Encore. “We call it three adjacent, you know, it’s cheap enough that—I think one of the really important parts and why 10 cents I think is the right has become for us, a really good answer. Like music is art, art has value. So artists should not have to give it away for free after establishing a floor price on an artist’s time, even if it’s 10 cents. It still establishes a floor price, and it really sets an expectation that, okay, they’re going to actually give you something real, and you’re actually going to be engaged in it.” 

According to Gray, artists who perform on the Encore app can walk away with a nice amount of money if they have an active fanbase. In his words, all it takes is good promotion, a great relationship with your fans, and you can walk away with at least $5,000. 

If you’re like, if you’re a SoundCloud rapper and you’ve got, you know, again, like half a million Instagram followers, you know, 100,000 monthly listeners, but there’s ten kids out there who have, you know, Instagram handles that are a riff on your name, I can guarantee you at least 2,500 bucks in 15 minutes,” said Gray. “And if you’re really good at promoting and have a good relationship with your fans, and you’ve got a Discord to promote over, and you have all of that kind of engagement, maybe you can make 5,000 bucks. And that’s in a 15-minute show that ultimately, you could do every week, every month, at some kind of frequency.

Kid Cudi’s March 7th performance was Encore’s biggest to date, with the rapper/actor walking away with over $140,000 after a 35-minute performance watched by almost 14,000 fans. Cudi’s performance started with over 1.2 million claps and accumulated over 2 million claps at the show’s end; Gray shared that Cudi offered incentives for his fans, which other artists might want to emulate.

[Kid] Cudi promoted the show for two weeks. He created incentives for fans. In addition, to the backstage pass and meeting him. He was offering to take someone—flying them out for his tour. He was giving away free t-shirts. So, you know, having a huge lead-up time for [the] promotion and creating some really strong incentives for fans to want to be there,” Gray said. “It led to basically two weeks of all these fans in the app every day, people coming back, people climbing the leaderboard, people chatting, all that kind of stuff. And so, you know, he had tons and tons of claps before anything even started. That was the biggest show we’ve ever had, you know, also, it was really was not heavy AR (Augmented Reality). It was just him, mood-lighting, a living room.”

However, Cudi’s performance was mild, relaxed, and personal compared to the younger artist, Trippie Redd, who took advantage of the app’s augmented reality, far more energized and excitable. In addition, Gray revealed that Trippie Redd only started promoting his show hours before the performance was scheduled, far different from Cudi, who spent weeks promoting his show. 

“He’s a 22-year-old kid with face tattoos, and it was perfect for him. He had this cool immersive world with trippie heads floating around, and he was running around and jumping like a maniac and throwing his socks off and all that shit,” Gray shared. “And one of the things that were cool with him, is he started to promote that show 10 hours before the show started. So it was the morning of the show that he started posting on his socials about the show. We started the day with 200 fans in the lobby. It was almost 6,000 by the end of the show. And so what was really cool and he made you know, it was about 420,000 claps, which was 42 thousand dollars.

The two artists used different approaches to promoting their shows. While Cudi was upfront, he gave away claps to his fans through a special link that he shared on his socials; Trippie showed very low promotion with new fans coming in during the show. “It was just like, ‘hey, I’m going to do the show tonight. Come check it out.’ And then his fans came in, and then they started promoting it, and it just started this effect. And so it was really cool because that was so, I mean—$42,000 with 10 hours of promotion on a 15-minute show. That was pretty great.

When I asked Mr. Gray where he saw Encore being in a year, he told me that he believes the team will produce fewer Encore shows. Instead, artists and their teams will produce more of the shows. Additionally, he said that the “studio” app that the Encore team uses to create its shows is now publicly available. Each day, the app verifies new artists, making it easy for them to put on their own live shows. 

It’s actually picking up tremendous steam, and so over the next month, you’ll start to see shows that happen outside of LA, outside of any Encore control. And that’s the really exciting thing, is putting this in the hands of stuff. I’ve always said, ‘this is about enabling a 16-year-old kid in their mom’s basement,” Gray said. “who has tremendous talent and creativity, a real shot at creating really great elevated content.’ They don’t have 25,000 thousand dollars, and they don’t have a videographer friend, and they don’t know any video editors, and they don’t have—you know, all of the things you would need even to make a music video.

Gray understands that most musicians’ tools can be very inaccessible for young kids wanting to make a name for themselves, something that Cudi understands all too well and wants to change for “the kids.” 

That’s definitely the whole point of the company, you know, we’ve always said is this, ‘we call it Cudi and the kids,’ it’s not about Cudi, it’s about the kids. And the whole reason that Cudi got involved was not so that he could go and make more money. It was all about how he could use his platform and reach to bring in eyeballs so that these other kids could pay rent,” Gray explained. “And that’s really what is the most true to Cudi and the most true to all of us; you know like that’s why I did decide to jump into this company, even though I said I wouldn’t do another company and why I get like unbounded energy and excitement for what we’re doing because we actually already are making a difference in people’s lives and we just started it.”

You can follow Mr. Gray on Twitter at @JGrayLA and the official Encore social media accounts at @ClapforEncore (Twitter and Instagram).

And the Encore app is available on both the Apple store and Google Play store.