When I started pursuing a career in music, one chorus of advice recurred.
Don’t do it.
Turn around while you still can.
Avoid this industry at all costs.
The landscape at the time inspired grave warnings. I dipped a toe in fast-receding waters around 2009/2010. Job security and corporate strength hit all time lows. Would-be advisors gave me guidance born as much from prudent observation as self-preservation.
Bad omens proved fruitless. By the time I was asking for advice about the music industry, I’d already etched dreams in my mind. I wasn’t sure if the industry’s particular flavor of terrible would suit my life, but I was set on finding out.
All this advice may well have been correct, regardless of the era. As any of my friends (or my therapist) can tell you, I love what I do. I also complain about the industry’s draining vicissitudes constantly. The music business remains the hallowed dream thresher of lore, idealists and softies ground to dust in its gears. It is run by cynics, driven by perverse profit imperatives, and horribly regulated.
Miraculously, I’ve worked in music for a decade. Nearly a third of my life. Being a moody, philosophizing fuck, I’ve spent a lot of that time contemplating this business and the best ways to navigate it.
What follows is not a guide book. No secret codes, no magic bullets, no set prescriptions, no panaceas for fledgling careers or flagging businesses. My observations might not even help you, but I hope they provide some clarity about a field that mystifies so many, that gnashes dreamers, rewards thieves, and so often brutalizes our best, brightest artists. A masochistic labyrinth without end, it also attracts some of the most passionate, thoughtful people I’ve ever met. Burning crusaders who create or support dazzling art that defies odds, tops charts, and shapes lives.
My observations come from a very specific perspective. During my decade in music, I’ve been a writer, a record label A&R, a publishing A&R, a manager, and had a hand in product development. I have managed producers and artists for the majority of my career. I’ve done my level best to defend their rights and interests, and build stable careers for them. I have been chronically bad at jobs where I could not shape the conditions of my work around my particular ideological quirks. Management has been in turns the most entrepreneurial, the freest, the most challenging, the most emotionally draining, and the most rewarding work. As my primary experience, it undoubtedly shapes biases about the business.
I’m writing this now because our industry is at another inflection point. I started scribbling this piece after attending my first Grammy Awards earlier this year, an experience that invigorated me as a fan (Stevie Wonder live! A surprisingly energetic, thoughtful tribute to the 50th anniversary of Hip-Hop! Beyonce breaking records!), while frustrating and confusing me as a professional (what the fuck is this thing now? Is it a popularity contest? A signifier of music quality and posterity? A fun concert? All three? None?). Even though ratings went up for the first time in years, it was hard to experience the 2023 Grammy’s and feel as though they were deeply connected to the rapidly changing world outside the Crypto.com Arena (which has only been Crypto.com for a year and already feels due another name change before the end of the decade).
I was a teenager during the industry's last major refractory evolution: Napster’s assault on the sales value of music, the labels vs. the internet, and the dawn of the digital native age. In 2023, artificial intelligence calls the futures of creatives and executives alike into question. Labels, distributors, and publishers largely report booming revenues (while new frontiers of monetization promise even bigger boom times). Uncertain economic conditions abate the flood of catalog acquisitions and venture investments. The TikTok gods anoint surprise hits of songs old and new.
I wrote something similar for Complex in 2015. In re-reading it, I was shocked to find I still stand by almost all of it. So much so that I incidentally repeated myself a bit in what I wrote below. The following list is by no means exhaustive. I may update it annually. Or I may come back to it in a decade, if we’re all still standing. It may be overly simplistic. It may feel rife with truisms. I am not sure who comprises the audience for this piece, but I hope it finds you wherever you are, whenever you read it, and gives you something meaningful to chew on.
Since this is long, here’s a playlist to soundtrack your read:
The industry needs youth but fears it. I’m not just talking about the audience. A&R’s, marketers, publicists, writers, developers, producers, songwriters, artists. Young, inexpensive, inexperienced idealists with big ideas, great taste, and greater hustle provide grist for the music industrial mill. Many leaders of the industry—record label execs in particular—pay lip service to the earnest exuberance and knowledge of the young. They turn around and take credit for their ideas and block their upward mobility, fearing they’ll be replaced by their juniors (because, naturally, they will—they’re just trying to stem the inevitable). The greatest leaders I’ve met have embraced youth and meant it; they’re real mentors who understand that tutelage is a two-way street.
The industry runs on talent but disdains it. How else can you explain the structure of a 16pt royalty deal where an artist doesn’t own their masters? Or one in which artists have to battle with their record labels for “creative control?” Or one in which the primary tool for listening to music in the modern world is also funneling fake artists into its platform? Every company that works with artists and the intellectual property they make knows the importance of these creations, their worth, and their intangible reach. Many executives wax poetic about the paramount place of talent while simultaneously moving to devalue it behind closed doors. It is a paradox as old as the entertainment industry itself. (I can already hear the chorus of those who’d defend labels and publishers as the primary capital partners in bringing art to market. Believe me, I get their importance in commercial art at scale. That role doesn’t make the industry’s core mechanisms less vampiric.) If you need an example of this dynamic unfolding in an adjacent industry, look to the WGA and SAG-AFTRA strikes in Hollywood, and the comments of studio executives in response.
A lot of perceived malfeasance is caused by human error/overload…In the age of runaway growth imperatives, companies always seek ways to expand profit margins. That typically means fewer employees servicing more “clients.” In the case of record labels and publishers, this has been at least partially true in the boom time following the rapid contraction of the early 2010s. A&R’s have signed far more artists than they can possibly service. Those artists, in turn, work with tons of independent contractors: Producers, engineers, designers, directors, stylists, biographers, and countless other creative folks who are not employed directly by labels, but rely on them for payment. Administrators at labels are responsible for making sure these folks get paid. Those administrators might be seasoned professionals, they might be young people pushing paper because they just wanted some job in music. They’re all human beings, and, as humans do, they fuck up. Try not to be a dick with administrators. A lot of their mistakes are probably not intentionally malicious. With that said, just because something is unintentional doesn’t mean it’s not hurtful to creative people. Almost every producer and artist that I work with has suffered at the hands of unintentional errors fucking with their music making its way into the world, or money making its way into their bank accounts.
…but also these companies make it really hard to get paid (because the industry is not designed to remunerate creative people efficiently). Anyone who has ever read a record deal or tried to get paid for freelance work will confirm. It is totally understandable to get frustrated, particularly when some anonymous bureaucratic cog on the other end of an email obstructs payment with no good reason, then doesn’t respond, then cites some byzantine company policy as a reason for not handling something. This dedication to corporate stricture is one of the most insidious vice presses companies throughout the industry apply to creative people; they can cause the kind of fatigue and confusion designed to make you wonder if the money’s even worth the extra work (it is).
Getting people paid is the most important skill you can learn. Pay on time, pay consistently, and apologize if you are ever late (or at least explain why). Assume that a payment might mean life or death for someone. I made many friends early as an A&R commissioning remixes and getting people paid for their work (whether it was ever commercially exploited). I have also made mistakes and had to correct them. The apology never makes up for the squeeze of not having money in your pocket to cover basic needs. It is easy to get caught up in the delayed nature of the business. Don’t let that guide your practice.
You can survive at a major label or publisher by never swinging for the fences and simply knowing what’s going on in music. A powerful lawyer (one of those “name in the firm’s name” types) once told me that if I didn’t fly too high or too low and just stayed aware of a few hot things a year, I could maintain a job at a major label for a long time. Not have hits. Not even sign anything. Just know stuff. Presumably one should have relationships to “get in the mix” on deals, but he didn’t even specify that.
This is a business of stars, everyone else splits the (relative) scraps. According to Spotify’s recent reporting, 1060 acts earned over $1m per year from Spotify (up from 460 artists in 2017). While that is a staggering number of artists, contrast it with a few figures. In 2021, 52,600 (15,140 of whom were independent) artists generated over $10,000 each in revenue. Bear in mind these are gross revenue figures. They don’t include payouts to third parties (such as producers, songwriters, mixers, featured artists). On top of that, Spotify claims to host 11 million active creators between musicians and podcasters. While this only speaks to the blockbuster nature of the music business in microcosm, it’s a helpful gauge for how few artists achieve truly stratospheric success within music. I’m only talking about streaming, saying nothing of touring, merchandising, endorsements, and all manner of other financial windfalls lavished on visible stars. On this topic, it is also highly worth reading Anita Elberse’s 2013 book Blockbusters, which summarizes the rules still governing the prevalent thought in the current media landscape a decade later. This line of thought may be buckling as one comic book film after another tanks and artists like Steve Lacy become superstars, but it undoubtedly still colors executive decision making at the highest levels.
Those stars are (primarily) artists. You will hear many stories about them not doing right by the people that make their artistry possible (producers, songwriters, creative directors, etc.) Not all artists engage in selfish practice, but, by its very nature, the act of becoming a famous, successful artist requires a level of delusion and egocentrism that often leaves little oxygen for praising others. This principle applies as much to artists as to executives. Memoirist Claire Dederee’s recent book Monsters sharply enumerated this nature: “There are many qualities one must possess to be a working writer or artist. Talent, brains, tenacity. Wealthy parents are good. You should definitely try to have those. But first among equals, when it comes to necessary ingredients, is selfishness. A book is made out of small selfishness. The selfishness of shutting the door against your family. The selfishness of shutting your door against your family. The selfishness of ignoring the pram in the hall. The selfishness of forgetting the real world to create a new one. The selfishness of stealing stories from real people. The selfishness of saving the best of yourself for that blank-faced anonymous paramour, the reader. The selfishness that comes from simply saying what you have to say.” Selfishness doesn’t define all artists, but a little solipsism forms a necessary backbone of any public-facing success. Always remember: No growth or great achievement happens in a vacuum. Everyone learns from someone. Many hands deliver every work of art into the world.
This reign of stars defines consumer art. The selfishness described above can reap big dividends. Music is not an exception. Film, sports, academia, business, law, politics. In almost every field, America worships the myth of individual genius. We forgive sins big and small in the name of genius. Capitalistic systems heap individual achievement (however that gets measured) with outsized spoils.
Collaboration is key. A few months ago, a close friend asked me: “If you met Take A Daytrip at the beginning of their arc with the knowledge you have now, what would be your key piece of advice?” Countless thoughts swirled, but one cut through: The path to your dreams will be paved by collaboration with others. Beware the myth of the individual genius—it poisons people into thinking they need to do things themselves and that that is somehow more honorable than working with other amazing people to bring ideas to life. Embrace collaboration. Celebrate your collaborators. It is not just a faster path to success, it’s a way to build lasting relationships that will simply make your life better.
If your work is primarily in support of creative people, never tell them something is going to be “hard” for you. A few months into managing Michael Uzowuru, he told me that an artist had cribbed a bit of inspiration he’d provided for a video and wanted to figure out the recourse for compensation and attribution. I told him it would be hard to do that, for a number of reasons (which would shortly be made irrelevant). He paused. “Don’t tell a creative person that something you do is going to be hard,” he said. “I know it’s hard. What I do every day is hard.” This conversation fundamentally changed the way I think about management and still guides me nearly a decade later. Making a living off of art is nearly impossible. Keep that in mind when you talk to artists, producers, songwriters, painters, writers, etc.
Build and maintain a rolodex of people in various worlds who can be the answers to different questions. Digital security experts, food and wine plugs, handlers, fixers, lawyers, litigators, multi-instrumentalists, gallerists, gardeners, contractors, sneaker dudes, bouncers, drug dealers, and so on. As your career continues, regardless of what aspect of music you work in, you will likely find yourself trying to make increasingly outlandish wishes into realities. Let your moral compass be your guide on whether or not you should fulfill some of those wishes, but know that wish fulfillment is a big part of many jobs in music.
Develop a creative diet. Never stop feeding your head with music, books, films, trips, conversations, and art. Everything, new and old, is potential inspiration. Develop (and renew, when necessary) rituals that keep you fed with idea fodder. This goes for the people who support artists as much as the artists themselves.
Beware of Daniel Plainview’s. There Will Be Blood is probably my favorite film ever made. Throughout it, monomaniacal oil tycoon Daniel Plainview (played perfectly by Daniel Day Lewis) tells the residents of a California nowhereville that he is the only person suited to pump the oil from their earth and make them all prosperous. What starts as a con takes on the hue of truth when Plainview hits a gusher and starts producing enough oil to make him a serious competitor to the major corporations of the west. His line was always a con. Any number of other prospectors and established players could have gotten that oil. He just got to it first and sold his yarn most convincingly. The music business is teeming with Daniel Plainviews.
IP Ownership is crucial, but means very little without the right mechanisms to make that IP valuable. This is a corollary to #2, as anyone at a label or publisher will argue that their work is in service of making music valuable. In a literal sense, this argument is true. That’s their job. Regardless of the infrastructure you choose as an artist, producer, or songwriter, the monetary value of your creation is going to be largely dependent on luck, tireless work, and your willingness to lean into systems of consumption. All that said, don’t get caught slipping. Understand any deal you do. Know what you give up by signing and what you retain.
The narrative is everything until it’s not. In a career, you will encounter countless stories, projections, next big things, and industry darlings. It is easy to get lost in hype, gossip, and storytelling. These narratives are ephemeral. They change. Artists and their teams have power to change them, difficult as that may be. Time changes them. Always remember the ill-fated Kelefa Sanneh New York Times headline from 2003: “The Solo Beyoncé: She's No Ashanti.” Don’t let yourself get caught up in the superficial while pursuing your goals. Simultaneously and paradoxically: An understanding of how to ride certain narrative waves can be crucial. It is exceptionally hard to build a career off trend-hopping and often leads people to ramp into outrageous antics over time.
Persistence. Persistence. Persistence. You will fail so many times it will become difficult to keep track. You will forget about decks, ideas, late night fits of inspiration, and demos hidden deep on your hard drive. You will be told “no” so much it will seem like the only answer, regardless of the question. You might get laughed at—I certainly have. At every turn, you have to remember: This shit is hard. Success, however defined, is hard. Gaining attention is hard. Making great things is hard, even if they’re seemingly simple. The only way to achieve your goals is to keep going. In the words of Maya Angelou, “the work is all there is.”
Build small to go big. A spin on the old adage “think global act local.” Focus on individual fans and connections. We are entering an era of small niches on larger scales—bigger subgroups of fans that idolize more different artists, rather than a cultural monolith rising around a singular artist. In this new era, you must focus on community and individual fan acquisition if you want to build something sustainable enough to eventually go big. Hone in your specific message, your specific aesthetic, your thing, whatever that is. As every writing teacher I loved ever told me, find the general in the specific. Don’t make art so general it means nothing to anyone.
You are no longer competing against your peers when you release music, you’re competing against the entire history of recorded sound (and also movies, sports, video games, podcasts, YouTube, TikTok, everything but Quibi). That knowledge shouldn’t necessarily factor into your creative process, but it’s important to keep in mind when for you or anyone marketing your creations.
You have to decide who you want to be. As an artist, as an executive, as a manager, as anything in this industry. Who do you want to be? Do you want to dedicate yourself ceaselessly to hard hewn quality, or go for facile, copycat ideas? Are you obsessed with financial success or making great art? You can have success in any number of ways (especially depending on your definition). In my experience, you lose yourself when you don’t have a clear sense of what that success looks like. Define it for yourself. Don’t let others define it for you. Define it clearly. Interrogate it often.
If you want to be considered valuable, create value. When I got laid off from my first A&R gig at a major label, I realized three important lessons in short order: I owned nothing, no one owed me anything, and I hadn’t done anything to make someone want to keep me around. I’d created no value.
You never know what someone else is thinking or going through. Even when you disagree with someone or think they’re saying something you find stupid, hear them out till the end. It is the decent thing to do and may lead to unexpected positive outcomes. Walk with empathy.
You can’t build a creative company entirely off “vibe” people. Someone, somewhere, at some point in a company will have to understand how to build out an Excel spreadsheet or organize a Dropbox folder. There is an obsession in the music business with mythical cool people who know about art and great restaurants, who show up late to the office and leave early so they can float to the next gallery opening or underground rave. The work of those people can be immeasurably valuable in attracting artists to work with a label, publisher, management company, or brand. These creatures can be true muses. Their work stands on the bedrock of people who show up on time, do boring work, and don’t often get to share in the superficial spoils. Make sure you treat those people well. You’ll need them to build anything lasting.
Creative development mostly comes down to producers (and some managers). When the industry deflated in the early 2000s, labels largely abdicated their responsibility to patiently develop artists. At present, labels largely pay to acquire talents that have already built considerable commercial tailwinds. Whatever there is of a development process comes largely at the hands of producers and managers who understand that creativity takes time, failure, life experience, and hard, unglamorous work to blossom. Producers and managers, often unburdened by the restrictions of the corporate fiscal year, have the space to experiment, try out sounds, and fail in search of that elusive something. This “space” can come from having tons of money and resources, or from having no resources (though the romanticization of the starving artist is largely horse shit, there is some truth to the notion that you may make some of your best work before commercial pressures and opinions tied to salaries enter the fold). To quote the great Toni Cade Bambara (on writing, but it surely applies to musical creation): “People have to have permission to write, and they have to be given space to breathe and stumble. They have to be given time to develop and to reveal what they can do.”
You are going to disappoint people. You are going to be disappointed. That’s life, but it’s also really crucial to remember in the context of a business that is so often rooted in the fulfillment of strange wishes with long odds.
Always be a student. My father was a dentist. He worked until he was 78 1/2 years old, when blood cancer, Parkinsons, and a condition called steroidal myopathy made it impossible for him to comfortably sit in a dental chair with steady hands. Through illness, through decades, through changes in the practice of dentistry, my father always read, always attended conferences, always sought new information about the profession he’d been in since 1962. The most successful people (and, in many cases, the happiest) I’ve encountered in music and other creative fields are the ones who never stop learning—who ceaselessly search for ways to improve their craft, regardless of outcomes.
Stay consistent...
...but don’t be afraid to pivot and reinvent yourself. Or, as my therapist always tells me: Adaptability is the most important skill for a happy life.
Set realistic expectations for your partners (and for yourself)...Before starting a project, it’s important to establish explicit guidelines and goals. The smallest benchmarks quickly accumulate into big progress. When you hire, build teams, or bring on new partners, having documentation that clearly outlines roles and expectations is crucial. It may seem a bit clinical and uncool in a profession that’s supposed to befit free spirits, but this level of pragmatism will save you a lot of pain in the long run.
...but always dream big. Without the dream, the whole insane artifice can crush you like cold, unflinching stone.
Find ways to reduce stress through your communication of stressful information. Particularly as a manager, you constantly have to deliver difficult, delicate, potentially disappointing information in this profession. Sure, you can rip the bandaid off and just drop the news like a brick on a toe, but you’re better served figuring out the right times and the best ways to frame potentially frustrating details. The right methods are going to depend on your personality and the people with whom you’re sharing information, but one rule of thumb I follow is to never get particularly worked up as I relay a situation. If you communicate calmly, it sets the tone for practical handling of a situation, even if disappointment and sadness are inevitable as responses to the information you’re sharing. Always take a deep breath before you start (and keep breathing).
Deadlines are fake...As an A&R said to me recently, most deadlines at labels are suggestions at best. Companies like Spotify and Apple will tell you they need 3-4 weeks lead time for ingested releases to have their editorial staff members properly review them, only to have Drake deliver a surprise album at 11:59PM and get playlist placement at 12:01AM (see #7 & #8).
...but time matters. You can miss windows. You can fuck up campaigns. You can waste people’s time and be left with nothing in return. Time is all we ultimately have, but it is often wielded as a cudgel by people whose jobs and meetings are governed by the pendulum swing of the fiscal year. That sense of time can leave you sweating and feeling empty. Don’t let it distract you from figuring out what time is important for you: When to study, when to work, when to act.
Even time well spent may feel like time wasted. This is the nature of creative pursuits or work in support of creative people. Populated by what if’s, never was’s, and infinite potential made impossible by the singular rail of a lifetime. You can only move forward with the backdrop of what is behind (and the choice to consume or ignore it).
Don’t bet against technology. The music business is consistently behind the technological eightball. Make sure that you are not.
Love the process. Love the people. They will ultimately be all you have. If you make art, you must learn to derive joy from the act of making it. The constant starts and rough drafts, iterations and near-finished edits. You have to find some pleasure, big or small, in learning, in trying, in making things that never see the light of day. Creation should become a joyful sport in itself. Through this journey, you’ll meet some terrible people, no doubt. If you are as fortunate as I have been, you’ll also meet some of the most special people in your life. People who love music in ways that defy words. Great artists. Defenders of artists. People whose work is art, no matter their title. These people will become your friends, your partners, your confidants. Hits come and go. Money comes and goes. The best you can hope for is that you collect great people, great knowledge, and great stories through your career. If you make a lot of money, you’re really fucking lucky.
If the art you love doesn’t make someone money, it’ll probably disappear. Or “many of my favorite songs are only available on deep, dark corners of YouTube, and probably not for long.”
The big successes are rarely the expected ones. As Take A Daytrip’s first hit, the song “Mo Bamba” fundamentally changed their lives and mine. None of us would have predicted that would be their first hit, let alone one of the songs that defines their career and endures years later (before you roll your eyes: Throw it on in almost any club and see what happens). Conversely, there are countless artists we loved, worked with, devoted months, sometimes years to and thought would be successful (both unknown and well known) that simply weren’t. Much success is a series of happy accidents aligning.
The only leverage you truly have is saying no and meaning it.
Incredible read.
Incredible writing and a rare capture of the nuances of the music industry... great stuff, Jon! And that mid journey art is eerily relatable haha!