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Chance The Start Up: Dissecting Music’s Favorite Indie Obsession

A Chance the Rapper show is something every person ought to experience in their lifetime. Every year since his initial step onto the scene in 2012, more have been able to do so, with his Matryoshka doll-like venue growth spanning from selling out the 500-cap Lincoln Hall in Chicago two months after 10 Day, to playing a thousand, then three, then five—up until this moment, where it finally felt like the crowd was in line with the man’s musical gift and the reach of his songs and the passion for them that his listeners feel so deeply was accurately represented in the crowd he was about to play for. One evening this past April, nearly 10,000 people poured into the Valley View Casino Center in San Diego for his tour’s opening night, filling a venue to capacity that was large enough to have once hosted an NBA team (the now-Houston-based Rockets), an NBA all-star game, and an NCAA Final Four. Chance had last been out there only seven months prior for his Magnificent Coloring World Tour, but in that short time he’d again doubled the capacity of a venue he could fill. Was anybody surprised, though? Chance just isn’t the artist whose growing fame will ever elicit disbelief, no matter how high we all expect him to rise.

Just two weeks prior the Chicago native and outspokenly-independent artist had turned twenty-four, and it was rather fitting that he’d have such a milestone sit right atop this new year, considering the one he’d just had: three Grammy’s (including the highly-coveted and often controversial Best Rap Album), the almost unanimous critical and cultural adoration of his third project, Coloring Book, and its historic achievement of peaking at number eight on the Billboard charts solely off of streams (it was the first streaming-only release ever to even chart). This tour, Chance’s first run of many, many shows to come headlining arenas, was to be his passionate victory lap; a time to celebrate with the fanbase that had played a far larger role in getting him to this stage than just about any other artist who’d ever played a venue this size before. Chance and his furiously-talented band played beloved numbers from both Acid Rap and Coloring Book, the Surf-favorite “Sunday Candy,” and even a few Kanye covers, too — before that ubiquitous choir-laden, early-’Ye-inspired pitched-up-soul beat of “No Problem” came booming from the speakers.

While there are a handful of single records in Chance’s discography that feel like a near-perfect encapsulation of his musical gifts and vision, no other song he’s recorded to date (apart from maybe the 2014 one-off “Home Studio” that opens with the label gut-punch, “Young black boy, how he got the labels scared?/A&Rs like, ‘Chano you ain’t playin’ fair!’ ”) also carries with it such clarity about his larger mission and anti-label advocacy. Sure, it also has the two biggest guest-rap verses his career has wrought to date, and a harmonious gospel-rap sound that potently echoes back to the College Dropout days that so inspired a young Chance. But its triumphancy runs deeper than that. As Chance began bouncing around the stage and roaring the hook, with Donnie’s vibrant and buttery trumpet cutting straight through the collective band’s sound, that sense was magnified even further, as fans caught the first glimpse at a video sequence that would come to define much of the press surrounding the tour.

#ColoringBook available now at

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Here was Chance, in front of this vast sea of fans, whom just half of could’ve fit when he came here last, becoming miniaturized on stage by the screen revising the well-known logos of majors from Def Jam to “Don’t Join,” from SONY to “PHONY,” from Virgin to “Villain.” Here was this formal and very-public cementation of his “anti-label, pro-famous” agenda into the foundations of his career’s biggest moment yet, a scene that this rap sensation would take and replicate inside sold-out, corporately-owned arenas across the country, doubling-down as a champion of independent artistry while surfing atop a heightening wave created by the kind of swift tides that, to this point, major labels had thought they alone could muster.

* * *

While Lil Chano From 79th is arguably the most famous rapper ever to be as outspoken as he is about maintaining independence, and his success has sparked a time in which it’s such a fad that even some artists who’ve signed deals have kept them on the down low (cc: Logic in this interview on Hot 97, though he’s far from the worst culprit), he is simply a modern-day figurehead of a scene which has been relevant and substantive since even before his birth.

As hip-hop continued to trend upward in its mainstream popularity throughout the ‘90s, aspiring artists and entrepreneurs began to be thoughtful about how they might cultivate homes for a sound more alternative to the early iterations of pop-rap, which was finding a great deal of success and national relevance. In 1995, Coolio’s “Gangsta’s Paradise” topped the Hot 100 for three weeks, with songs like “Ice Ice Baby,” “Baby Got Back,” and “Jump” also reaching that milestone in the few years prior. That same year two major-label alternatives were launched, Rhymesayers Entertainment and Rawkus Records (with other notable additions like Stones Throw and Strange Famous forming in 1996), and both would become huge players in the indie rap scene for the foreseeable future.

Chance is the music world’s founder that wants to be Bill Gates, who wants to be Anita Roddick, who doesn’t want to compromise neither wealth nor control along the way to realizing his dream.

While many of the genre’s biggest independent artists and labels have proved to be rather content with existing primarily within the underground, Rawkus was one of the first to think bigger and challenge the majors for exposure. Jarret Myer, who co-founded the label (as well as UPROXX), has much to say about that period in rap:

“Looking back now, it must have seemed crazy to the major radio stations, BET and MTV that this label outside of the major system had the balls to demand that its brand of rebellious music be broadcast alongside the priorities of behemoths like Sony, BMG and Universal. We just believed in our music so much. We had picket signs and petitions ready to go if anybody stood in our way. Luckily we had champions at these outlets like Hot 97, Power 106, BET and MTV. Those DJs and programmers didn’t play everything we pushed, but they took chances because they recognized greatness in the artists and a legit street movement that supported them.

“When we came into the game with Rawkus, we had such a large and obvious target to address: shiny suit rap. Puff and them gave us purpose to fight against. They were our fuel. If the popular sound at the time was shiny, made for the radio, and pumped full of corporate dollars, we had to be the opposite. We were grassroots in marketing and revolutionary in sound. From an A&R perspective, Brian and I always wanted to sign artists like John Lennon, Bob Marley, the Clash, and Marvin Gaye. Artists whose mission was as important as their music. We felt like we found those artists when we started to work our roster. Brian and I also grew up listening to a lot of punk rock music and that mentality really informed our label, our marketing, and our philosophy. I remember when I got Company Flow’s label solicitation package it came with a bunch of demands such as owning their masters. It was a super punk rock attitude and very out of line with what labels were doing at the time. It was like, ‘f**k you, we actually don’t want a label deal,’ and we loved it and ran with their energy. El-P’s ‘f**k you’ philosophy that he still has to this day really informed our philosophy at Rawkus. We felt if he was brave enough to wave his middle finger at the industry, we could do it, too.”

The courageousness of Myer and his long-time partner, Brian Brater, proved to be significant, as over the course of its early years, they released a handful of albums that have come to be widely-considered as classics to this day: Company Flow’s Funcrusher Plus, Mos Def and Talib Kweli’s debut as Black Star, Lyricist Lounge one and two, Mos Def’s Black on Both Sides, Big L’s The Big Picture, Pharoahe Monch’s Internal Affairs, and Reflection Eternal (Kweli & Hi-Tek)’s Train of Thought, just to name a few.

Chance The Rapper: Dissecting Music's Big Indie Obsession
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While some of the label’s later releases did involve early iterations of the kinds of distribution deals many indies have in place today, and Myer and Brater raised corporate financing to fund their releases, it was a pioneering moment to have hip-hop music finding such success all-the-while being created without major label intervention. To have so many important rap records of the time garnering sufficient exposure and finding the audience they deserved, and yet it was a distinctly separate enterprise from the A&Rs who were on a rap artist signing-frenzy, trying to replicate the sound that was further solidifying itself on pop radio.

Rawkus’ biggest artist in its history (who remains their largest progeny to date) was Talib Kweli, whose dexterous raps, intellect, and political awareness earned him tremendous praise on his first two releases: his collab albums with Mos Def and Hi-Tek, respectively. But after those two releases in 1998 and 2000, he decided to go solo in 2002, hoping that going it alone and widening his palette of producers and overall sound might help him break into the mainstream. Prior to its release, Rawkus pushed two singles to radio, the Kanye-produced “Good to You” and the Bilal-featuring “Waitin’ for the DJ,” but neither of which—like plenty of Rawkus’ pitches—were successful, or eclipsed the Hot 100. He had another record that he’d made with Kanye which he knew was special, but while Rawkus (and its distributor at the time, Geffen) had enough resources to give its artists a chance, being independent still had its limits.

Part of that was in the actual creation of the music. While Rawkus offered its artists complete isolation from the thought-processes and demands of major label execs, they also had a much stiffer budget, which, for one, kept Kweli from being able to get a professional choir on the record. It also meant that once his first two singles had been passed on, his record was now categorized as “underground,” and Kweli remembers his promotional contact at Geffen telling him “Get By” was simply “an underground rap record that I might even have to convince mix show DJs to play… No one’s f**king with this.” But he went on to hire independent promotional companies to push it, and it caught on so much with New York and L.A. DJs that it ended up hitting number 77 on the Hot 100, the first charting solo record by a rap artist so far in Rawkus’ history. It even spawned a remix featuring verses from JAY-Z, Busta Rhymes, Kanye West, and Mos Def, though it never got an official release since Def Jam executive Lyor Cohen refused to allow Jay to appear on what he perceived as an underground rap record, and Rawkus didn’t have the funding to pay him his going rate for a verse.

Kweli, a Brooklyn native, just recently released his eighth solo album, Radio Silence, last year on his own label. Kweli says it was far more difficult in the late ‘90s as an independent to compete with artists from majors. “There were certain things that had to happen for you,” he says. “Frankly, if you didn’t have a sponsor, you couldn’t compete on the level with them. It had to sound a certain way. You had to be on MTV. If you didn’t sell a certain amount, it was over for you.” Kweli’s successes following “Get By” and his nationwide tour (on which he brought along Kanye, prior to his Roc-A-Fella deal), led to him to test out the major label scene, with his 2006 release Right About Now dropping on E1 and 2007’s Eardrum on Warner Bros — the latter of which debuted as the number two album in the country. Even so, Kweli recognized the lack of care his music received at majors, compared to how invested in the music and the culture the founders at Rawkus had been. “By the time I got to a major I got to see what the difference was between being part of a global corporation that doesn’t care about you, versus an indie that does,” he says. “But I used those platforms to build my name up, and by the time I went fully independent, I had the fanbase and I was the owner of it. I still don’t own the rights to some of that early music, but I do have those fans’ hearts.”

Part of his decision to create his own label and go completely independent was also that the Internet had created new marketplaces which were far more accessible to indie artists than when most sales were brick-and-mortar. “It’s much easier to be independent now because of the Internet. It’s leveled the playing field,” Kweli says. “Chance is hosting SNL even though he’s never sold a record. Artists are having success without owing labels content. They’re reinvesting in themselves and doing everything they can to get music to everywhere music is being listened to. People don’t need to rush to do what I did anymore… I personally wouldn’t advise any artist I know to take a deal.”

Sage Francis, the founder of Strange Famous Records and another pioneer of the early indie rap scene (in all his promo materials he’s dubbed as the “forefather of indie-hop”), was able to build a foundation purely off taking part in the battle circuit and songs being spread over file-sharing networks. By 2005 he’d become the first rapper signed to Epitaph Records, and was one of the world’s best-selling independent hip-hop artists. Here, he questions whether the digital explosion has been all good though, as it has certainly over-saturated the market to a point where his career-path is no longer possible for a new independent act today:

“It’s much easier to be a DIY artist these days which, ironically, probably makes it more difficult for DIY artists to be heard. Since it’s so easy to record music and release it to the world, all the channels are flooded. Everyone’s on SoundCloud, everyone’s on YouTube, everyone’s on every digital store and streaming service. Before the digital explosion, it took a lot more elbow grease in order to have something recorded and released to the public, but if you were able to get over all of the hurdles you had a good chance of getting spins on college radio. Not that college radio matters nearly as much as it did, but that’s just one example of how there was a clear path an artist could take if they believed enough in their music to invest the time and money. It was also easier to sell music before the digital music explosion because people were buying music. I was able to build my career and record label off of mixtape and album sales. Doing shows has always been a great way to do this, but even that is becoming more difficult considering how flooded the market is. It’s not as if the best talent rises to the top. More often than not it seems like the people with the right connections and/or “hustle” get noticed enough to acquire a large enough following to constitute a career. And that’s when we get into the blurred line of what ‘independent’ means these days. Are you beholden to someone else’s bottom line? Are you being financed by a music giant? ‘Indie’ is a buzzword obviously, and I’m not sure it’s fair to use it just because you aren’t signed to a label. Because a lot of us are really out here financing ourselves and calling all of our own shots, which, as a result, often leaves us with a taller hill to climb. It’s difficult to explain this without coming across as salty. I’m not. This is merely the battle I’ve been in since 1996, so I’ve got all these wild, grey hairs in my beard. I can accept that it’s just a whole different game than how it was when I started out.”

While the game has certainly changed, key platforms have provided artists with the chance to reach the majority of the marketplace in a way that simply wasn’t possible before, as most indie artists didn’t have the money to get themselves placed in enough record stores to compete. Rappers like BUGUS, who co-founded the independent label DIEMON with his childhood friend and frequent collaborator, Russ, see this era as more of an advantage.

“My only promotion is social media and word-of-mouth,” BUGUS says. “Radio is still useful but it has less and less pull on the success of a song. Take ‘Man’s Not Hot.’ That blew up on social media, no major label involved. Within a day, millions of people worldwide heard it. I don’t think there’s a single radio station in the entire world that is that powerful. We are truly in the future. It’s awesome. As an independent artist, I feel extremely empowered and I would have hated to be an artist in any other era.”

He expressed that similar budget issues persist, for sure (“I don’t have anyone I can call and yell at for a bigger music video budget”), but he’s one of thousands of artists for whom SoundCloud came at exactly the right time, and has been an invaluable tool in his building of a fanbase and a brand. Another such artist is none other than Chance’s younger brother, Taylor Bennett, who may shout from a smaller platform, but is equally vocal about the benefits of staying independent, both financially and artistically. His debut mixtape, 2013’s The Taylor Bennett Show, drew a tremendous amount of attention on SoundCloud, and led him down a similar path, choosing not to sell his music and keep full creative control over all his work to come, which culminated in him starting his own label, Tay Bennett Ent.

“I’ve always believed that whoever creates the product should be in charge of it,” Bennett says. “The reason I used SoundCloud was because I didn’t know how to sell my own music. There weren’t any distribution companies. What I did know is that putting music up there was going to be a good investment. I knew it was going to become a worldwide success for artists. What it got me more than anything else was exposure to people who didn’t use iTunes. Once that began to faze out, it was all about SoundCloud.”

But simply putting your music online, whether SoundCloud or a streaming platform that pays royalties simply isn’t enough, as Bennett quickly found. “I was the first person in my city to use TuneCore,” he says. “My experience was that it’ll just sit there. You can get your fans to listen to it, but how do you make sure Apple actually listens? That was the struggle me and [my manager] had. We had to make connections, and talk to people to make sure when our project came out, everybody saw it. I don’t think there are really any other independent artists who have penetrated into the industry the way we have without a deal. It’s hard to do without a distribution platform. Anyone with a distribution deal is not an independent artist. In order to be an independent artist you can’t have a publicist. You want to be loyal to your fans, but you still want to be on those billboards next to Beyonce. You still want to be in those shows with Young Thug. To be in those movies and commercials.”

While Kweli called moves like Macklemore’s partnership with a distributor (more on this later) just “smart business moves,” every independent artist is entitled to their own idea of what this over-used and quite ambiguous term entails. Others have called out Chance for signing his two-week exclusivity deal with Apple Music (most notably Joe Budden on his Complex show, Everyday Struggle), prompting him to release the full details of the deal over social media, an act of great integrity and transparency. But regardless of what different artists might express as the gray area with this term, studying the careers of those like Kweli and Sage Francis, Atmosphere and Brother Ali, Tech N9ne and El-P (and the list goes on and on and on and on), who all have had their own unique independent journeys and decision-making strategies and amounts of funding, shows us that really what’s most essential is the way they’ve parlayed the indie hustle into something no label can promise: longevity. In an era where you can look at any given year of XXL’s Freshman List and see a handful of artists who were signed just as swiftly as they were dropped, the sustainability that these veterans of the indie scene have shown is absolutely remarkable, and that’s what the modern-day leaders like Taylor and his older brother seek to replicate most.

We don’t have to let the man, per se, control what we’re doing with our art. We can all make so much — I don’t wanna say better sh*t — but we can. —JMSN

“For all of us who grew up without a lot of money, 700,000 or a million dollars on the table from a label to sign is hard to give up,” Bennett explains. “And as you grow more successful, the offers go up, too. But the question is, do you believe that your music can surpass the amount of money that labels are offering? It’s not just about having that hit record. You can have 50 million plays, and have 50 people come up to your shows. You have to be able to promote your own shows and promote your own music because it’s about longevity. It’s about being here 10 years later. Being somebody that your fans grow older with, and about growing as a person with your fans.”

* * *

In April of 2013, with just a few weeks left until its promised release, Acid Rap — Chance’s second and career-defining mixtape — wasn’t yet complete. While in recent years the triumphs of sudden-releases like Beyonce’s Lemonade and J. Cole’s 2014 Forest Hills Drive have pushed majors to reconsider whether the lengthy, telegraphed roll-out is always the best approach, at the time not many artists with a product as highly anticipated as his got to operate without a well-in-advance due date.

In the three weeks prior, Cash Money/Universal Republic had released two high-profile LPs: Tyga’s third album, Hotel California, and Lil Wayne’s tenth, I Am Not a Human Being II. Promotion for these had begun as early as the past summer, when the label sent out “My Homies Still” as Wayne’s first promotional single (only to be scrapped and become, as so many singles have, a single-turned-deluxe edition album cut). The album went on to have another two singles dropped before the end of the year (“No Worries” and “Love Me”), while Tyga’s roll-out included two hype-garnering mixtapes that fall, and three singles (“Dope,” “For the Road,” and “Molly”) before his release date that April.

Acid Rap’s 50,000-plus streams in its first 24 hours was a huge success for him and his team, especially considering that he’d had no A&Rs choosing and distributing singles months in advance, and little marketing or media attention to speak of. His success, in comparison to Tyga, whose Hotel California had underwhelmingly sold 54,000 in its first week, clearly showed that there was success to be had even with just the employment of YouTube and DatPiff (the mixtape, to this date, has over 1,600,000 downloads, is top-fifteen all-time, and the most played and downloaded mixtape by an independent artist in the site’s history). And yet, when answering questions from the media about his independence in the coming weeks, Chance’s stance towards labels was still relatively neutral:

“It’s super important to me to make music the way I want to make it, that’s the main reason why we’re still independent right now,” he told SPIN, just two weeks after Acid Rap’s release. “I can do literally whatever the f**k I want. I don’t have to make music a certain way and I don’t have any A&Rs telling me how my sh*t should sound. I don’t have a turn-in date for my mixtape. I didn’t have anyone to turn it into. I could take as long as I want to. If I didn’t want to release it, I could’ve just scrapped it. So whenever I get to a point where my worth is worth having all the freedoms that I ask for, then I’ll be at a point where I sign.”

Chance’s first label offer had come the summer before, two months after releasing his debut mixtape, 10 Day. It was through Vested in Culture, the new partnership between industry executive Sylvia Rhone and Epic Records’ CEO L.A. Reid, and Pat Corcoran, Chance’s manager, later claimed that him and Chance had been “so stoked” by the offer. “But my mentality was, ‘We’re just learning about all this.’”

A few weeks earlier he’d spoken similarly in an interview with Billboard, during which he was asked about his talks with labels — of which there’d been plenty (Columbia, Republic, Def Jam, RCA, Atlantic, Interscope, Shady, and Capitol, all reportedly had made offers already) — and stated matter-of-factly: “I don’t really like meetings, I like recording and performing music… But I need to set myself up for when the time does come that I need better distribution or just a bigger team behind me.”

Chance The Rapper: Dissecting Music's Big Indie Obsession
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What’s most intriguing about studying Chance’s history of speaking about this is how drastic the shift was that would come that summer. By its end, Acid Rap had sent Chance across the country touring with Mac Miller. It had sent him over to Europe to open for Eminem and Kendrick Lamar in front of 90,000 people. It had gotten him added to Macklemore & Ryan Lewis’ upcoming European run. It had even caused Lil Wayne to delay the release of Dedication 5 until he could secure a Chance feature. And yet, somehow, maybe the most remarkable thing was none of those, actually, and came in the form of the mixtape’s July appearance on Billboard’s Top R&B/Hip-Hop Albums chart due to a bootleg copy being sold over Amazon. Speaking with Rolling Stone in September (during which Pigeons & Planes asked, “Is Chance the Rapper having the best month ever?”), Chance answered why he hadn’t yet signed as definitively as ever: “There’s no reason to. It’s a dead industry.”

Acid Rap had, at the very least, further questioned the necessity of record labels, both in terms of their frequent impedance in the creative process, and in regards to their marketing power. Chance’s upcoming tourmates, Macklemore & Ryan Lewis, had also made a lasting indent on the independent rap scene, as their 2012 album The Heist had been released on their own label, and steadily grew from 78,000 first week sales to over a million by the time their European tour commenced. But they also had been the biggest beneficiaries to date of increasingly common deals between independent acts or labels and a distribution company — some of whom, like the Alternative Distribution Alliance (ADA) who were hired by Macklemore & Ryan Lewis — were actually owned by major labels.

While it’s fair to question whether this approach is as equally independent as some of the scene’s original trailblazers, the blueprint it produced was clear and also cogent: artists were fully capable of creating content completely divorced from any major label interference, keeping one-hundred-percent of the rights and artistic control, and still could pay a flat fee if they were so inclined to utilize the access to radio that companies like ADA could provide on a one-off basis. If Macklemore could ride this to the tune of four top-fifteen singles, and Chance could find himself charting without any such distribution deal or even his music available for sale (legally), then maybe Chance’s declaration that the industry was dead was actually a very calculated, early sign of how his career would ultimately unfold.

* * *

In his award-winning 2012 book, The Founder’s Dilemmas: Anticipating and Avoiding the Pitfalls That Can Sink a Startup, Noah Wasserman, the founding director of USC’s Founder Central Initiative and long-time Harvard Business School professor, writes about the key struggle that the founders of new companies face in choosing between wealth and control. “Many founders,” he writes, “have so much confidence in their startup’s prospects and in their own abilities and feel such intense passion for their idea that they systematically underestimate their need for further resources or overestimate their ability to remain in control… These natural entrepreneurial inclinations can lead founders away from becoming Rich or King as they make decisions that leave them with either too few resources or too little control of the startup.” (p. 337)

In his research, Wasserman identified founders who consistently make “control decisions” as likely to reach the King outcome—“… the founder retains the throne but does not rule as big and rich a kingdom as might otherwise have been possible.” On the flip side, those who make decisions primarily around wealth generally reach the Rich outcome—which, unsurprisingly, means that the founder “loses the throne but sees his or her venture pursue its business opportunity to the fullest.”

Regardless of the obvious differences between the motivations within the music industry and the business world, the parallels are certainly there. For instance, when we talk about the independent music scene, there will always be a handful of artists that choose that route because it’s simply their only option—what they’re creating doesn’t have the legs to garner mainstream appeal or label affection—but, there are plenty of others (such as Kweli) who started on a major and didn’t like what they found.

One of the best examples of this is JMSN, an R&B artist who signed to Universal Motown back in 2009 as Christian TV, and seemingly had a clear-cut route to a career of celebrity and fame. He’d performed on So You Think You Can Dance? and his single had been called Britney Spears’ favorite song of the summer in a widely-publicized tweet. But he was also firmly moving down the Rich path, as much of what he was making was controlled by the label, and had little to do with his own musical taste.

“I remember them being like, ‘You need to stop producing your own sh*t and work with these big producers.’ Or, ‘You need to stop writing your own songs and have these people who know how to write songs write them for you,’” he says. “They would tell me to sing more like Rihanna or to use more Auto-Tune. And they’d play songs for me like ‘I Gotta Feeling’ by the Black Eyed Peas and say I should make something like that… It’s difficult because you want them to put your album out, but in order to do so you have to make compromises.”

In an era where you can look at any given year of XXL’s Freshman List and see a handful of artists who were signed just as swiftly as they were dropped, the sustainability that these veterans of the indie scene have shown is absolutely remarkable.

His debut as Christian TV never came, because he decided he wanted to take back the reins, and instead played his label what would later become his first album as JMSN, Priscilla. “You always think that they believe in you, but they just wanted me to make the song that’s like everything on the radio. I brought them the album I wanted to put out and they were like, ‘Nah, we’re good,’ and I was dropped.”

To release the album, JMSN started his own label, White Room Records — on which he’s released each of his last five albums. “I was definitely trying to push everybody forward and out of this thinking about labels. There is so much more than that. We don’t have to let the man, per se, control what we’re doing with our art. We can all make so much — I don’t wanna say better sh*t — but we can. We really can. I wanna be one of the people who sticks to my guns and pushes it forward and proves that we can do it without that sh*t. And it’s hard as f**k, don’t get me wrong.”

Even with the rise of streaming platforms, which he’d hoped would equalize the playing field, the lion’s share of discovery opportunities go to major label artists, and it’s not quite as much of a independent-friendly market as you’d think. Austin Staubus, the Managing Director of ItsNoRequests, one of a growing number of playlisting services working with artists and labels to leverage independent playlists on Spotify. He confirmed that much of Spotify’s marketplace is difficult for indie acts to break into on their own.

“Currently, UMG, Sony, and Warner have a stake in Spotify (as well as their own branded playlist companies) which gives them priority with editors who make the decisions on what gets included in popular playlists like ‘Rap Caviar’ or ‘New Music Friday,’” Staubus says. “Every major label, distributor, and manager lobbies Spotify on a daily basis for playlist support. Very few independent artists are in touch.”

Chance The Rapper: Dissecting Music's Big Indie Obsession
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But services like Staubus’ have found success marketing independent acts, and also, Spotify’s new emerging artist program, RISE, give the sense that maybe their end-goal isn’t actually to remain in business with traditional labels at all. “There’s been rumors that Spotify is signing artists directly, sharing in the streaming revenue, and split testing their own releases. This makes sense, as Spotify currently pays out 70 percent of their revenue to labels. If they can work with independent artists directly and share in the revenue, Spotify could increase their margins significantly and effectively cut out labels and distributors, which I suspect is their ultimate goal.”

But even if Spotify does ultimately become more independent-friendly, money is still a common limiting factor for independent artists everywhere, and one that has continued to limit JMSN in his efforts to make his new music, of which he’s exceedingly more proud of, heard by as many listeners as possible. “Everyone wants to make their money in this business, so you just can’t get everything,” JMSN says. “I would love to be in places like Urban Outfitters, but that’s a label-driven thing and they don’t work with independent artists. I’d love to be in Best Buy. But there’s stuff you just can’t do.”

But for all its trade-offs, JMSN’s choice to retain his control rather than chase his loftiest financial potential had its purpose and it continues to, even if those money in mind don’t agree with his moves. “I can’t tell you how many times people told me I shouldn’t release a song,” he continues. “Even Spotify playlist people. Then once people start liking it, it’s everywhere. But I was listening to the top songs playlist last week and I was like, ‘Holy sh*t, I make nothing close to any of this stuff’ So of course nobody thinks it’s going to work when they first hear something different. At the end of the day, I’m just trying to make the best stuff I can, and not allow myself to be polluted by what’s going on today, because it’s all the same.”

Artists like JMSN and the countless others who began their careers on labels and later chose independence, have made career choices around staying upon the King course, and regardless of how much they may end up making, they’ll be able feel good about the product they’ve created. Such was the inspiration for Big K.R.I.T., the critically-acclaimed Mississippi rapper who left Def Jam last year. October’s sensational release, 4eva Is a Mighty Long Time, was the first album on which he’d had complete freedom, and it showed. “The business side of the music industry used to affect my creative process,” he told us. “Once I got off the label I was truly able to focus on the album. I was definitely able to craft the album the way I wanted to.”

An interesting business comparison to this is Craigslist, for—as was detailed in the 2010 book, Values-Centered Entrepreneurs and Their Companies—founder Craig Newmark repeatedly turned down acquisition offers from eBay that “would make him a millionaire many times over,” citing that “‘it just didn’t feel right’ considering that his business was never so much about making money and more about providing a useful service to communities… Newmark believes that he has to retain control of the company to assure that his vision of helping communities will endure.” For those with a mission and sense of artistic integrity that is greater than their financial aspirations, the King route will always be more appealing.

But some founders, despite Wasserman’s heady warnings, aren’t willing to compromise either. “They want to be the next Bill Gates of Microsoft or the next Anita Roddick of The Body Shop, prominent founders who managed to achieve both value creation and control,” Wasserman states in his book. “However, few founders are able to maximize both goals because… the actions that maximize one inherently hinder the other, and most founders are forced to choose.” While successes like Gates and Roddick are what primarily get the attention, Silicon Valley is filled with stories of companies that turned down acquisition deals and then lost significant value, or sold too early and never got to fully realize their vision for the company.

In an interview for The New York Times, Ben Horowitz, an early investor in Instagram and venture capitalist said, “It’s never obvious whether to sell or hold. When Kevin sold Instagram, people said he was a genius, and now they’re asking whether he did it too early, and they’re saying Snapchat is so bold. Who was right? We don’t know yet.”

What we do know is that if there are any parallels to be drawn here, Chance the Rapper is the founder that Wasserman has warned business owners everywhere not to try to become. The founder who has so much confidence in his prospects and abilities, and who feels “such intense passion for their idea” that he will want to reach all his dreams without compromise. Chance is the music world’s founder that wants to be Bill Gates, who wants to be Anita Roddick, who doesn’t want to compromise neither wealth nor control along the way to realizing his dream. And while many independent artists have found happiness and success along the King route, and many more rappers have signed deals and — at least temporarily — found themselves on the Rich path, Chance has tread that line in a way music (and business, too) history would tell us someone in all likelihood cannot.

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In January of 2015, just a month after becoming the first independent artist ever to play Saturday Night Live, Chance was featured in a cover story for The FADER. When asked to update his position on labels, he was typically thoughtful and candid, and shared the following: “I’ve met with every A&R, VP of A&R, president of the labels, CEOs. I know all these people. I’ve had a lot of advice from people who wouldn’t give me that same advice today… It’s not even that they have any ill will towards me because I didn’t take their advice at the time. They’re almost like, ‘Keep going. You’re in uncharted territory, and you’re helping to shed light on what [the state of the business] will look like, and we’re all curious.”

The following year, with Coloring Book complete and ready to be put on streaming for the first time, Chance’s team was met with what his manager called a lack of “wholesomeness” when trying to clear the appearances of major label artists such as Justin Bieber and Kanye West. In a recent episode of Complex’s Blueprint, Pat detailed the interaction: “It took the wind out of my sails when the first thing I heard from the Def Jam CEO was, ‘No way… not gonna happen. No way in f**king hell. Like, Bieber’s got an album out. Kanye just dropped his album. No f**king way are you taking the fuel from our fire and putting it on Chance’s bonfire.’”

That September, Chance took the stage for the first time at Ellen to give his television debut of “No Problem.” The set design was something Chance had pitched to a few different TV and awards shows, and the others had all refused. The stage was turned into a meeting room at “Generic Records,” with six businessmen scurrying through piles of paperwork around a conference table, surrounded by plaques of platinum records that lined the walls. Just as that same electric climax of the song’s first chorus hits, Chance and his crew burst inside and within seconds, paperwork has been torn up and is drifting in the air, the Generic executives are being pushed to the outer-edge of the room, and Chance is triumphantly dancing and stomping around atop the table.

As Chance moves to the front of the stage and is joined first by 2 Chainz and then Lil Wayne, the set drifts more into the background than anything else — the performance itself too captivating to shift your eyes from, apart from the hilarious amount of white paper that now covers the stage, and still is periodically lifted and tossed into the air. The performance’s true climax comes just as Lil Wayne prepares to send it into its final chorus, and redirects Chance so that he can deliver two newly-penned lines: “And if Cash Money try to stop me/I’ma let ‘em rob me, yeah right, like Ryan Lochte.” Chance’s enthusiasm in that moment, as he delivers the chorus that has become his calling card, and — maybe more aptly put, simply his calling — is as infectious as anything he’s ever done, and it is such that, if you look closely, even the Generic employees find themselves unable to resist the charm. As the set devolves from a kind of a sketch into an all-out celebration, the extras are no longer fully in character, flashing smiles, and unable to resist some minute dancing as they’re disorientingly spun around in their conference chairs.

Chance’s unrelenting drive to keep his anti-label agenda as a focal part of his aesthetic, especially as he continuously elevates toward being the biggest popstar of our time, is sure to continue causing some disarray inside the offices of record companies. And while this scene he created for Ellen was certainly hyperbolic and simplistic, maybe the realest truth was in those extras who couldn’t quite reach the end of the performance without giving in, without being so moved by the energy and the atmosphere that Chance had created here that they at least momentarily forgot what he was celebrating.