Applied Science #16: Lessons & Observations 2025
Another set of anecdotes and advice from my time in the music industry.
A year and a half ago, I dusted off this Substack to share lessons and observations I had gathered from my decade in the music industry. Much to my joy and surprise, it resonated, with readers reaching out to share aspects of their own stories they saw reflected in what I’d written.
In the grand Hollywood tradition of bleeding a good thing dry, I am back with another round of lessons and observations. Many of these thoughts tumbled out immediately after hitting publish. I thought, “shit, how could I have missed that?” Some of them are bits of received wisdom, words from mentors that slipped my mind when I was reflecting for the first piece. Others are entirely new, drawn from life lived since the original publication.
I warn that this list is not exhaustive. Everything on this list forms a compass, not a map. No strict commandments. Guiding markers meant to help you get your bearings on unfamiliar terrain. And, once again, my advice shakes loose from my time spent as a talent manager. It may not make sense to everyone.
You can read the original 39 observations and lessons here (and reprinted below for ease and posterity). As before and as always, I hope these fragments of experience find you wherever you are, whenever you read them, and give you something meaningful to chew on.
Take a deep breath before responding...to anything. Your response will almost always be better for it. Particularly if someone has sent you an email or text that infuriates you, or if they’ve asked you a question (in person, on the phone, on a Zoom) that causes you to stumble, a deep breath can recenter your body and help you collect your thoughts.
Build horizontally / with your friends. When most people start out in an industry like music, they naturally look towards successful figures for inspiration and help. So many of us have sent our share of embarrassing emails, letters, texts, and DMs into the abyss that divides the aspirants from the heroes. In a career, you may bump up against some of your idols and the titans that inspired you in the first place. Some of them will live up to the hype. Others will deeply disappoint you. In any event, you likely won’t have a ton of time with them. They’re on their own journeys, often nearing their ends. It is often best to build with your peers and the people you love. Some of them will become the titans of tomorrow. Many of them will do amazing things and provide constant sources of inspiration. At the end of the day, you won’t be lonely in a profession that can often make you feel like a fool. In life, you spend far more time engaged in process than enjoying results. If you can do it with your friends, your life will feel all the fuller for it.
The seared steak method of staff management. My dad was a dentist who ran his own practice. He would often tell me that one of the biggest keys to running a business was setting an overarching goal and allowing people to work however they were comfortable to achieve it. “What you want their way,” he’d say in his typically gruff Brooklyn tone. Over the years, I’ve found this notion to be largely true, and I’d take it a step farther. In any creative field, it’s a fool’s errand to try and impose total order on the workplace. You can and should build strong, consistent systems that allow for work to be done efficiently, but there is no one right way to negotiate a deal or deliver an album. Set guidelines, but allow trusted team members to do what they do their way. This way of seeing staff management is much like searing a steak. You can use hot oil in a cast iron pan. You can use a broiler. You can use a pizza oven. You can use browned butter, high heat, then low and slow. You can reverse sear, chucking the steak in the oven first, then searing in a pan. You can temper your steak. You can take it right out of the fridge. You can salt it overnight. You can salt it right before. You can make your steak out of Lion’s Mane mushroom if you don’t eat meat. Ultimately, there is no one true way to achieve your desired result. It’s all about what feels best and works for you (and the team that, in this butter-basted metaphor, comprises your chefs).
Always ask questions. Stuck in the catacombs of my drafts lies an essay entitled “WE DON’T ASK QUESTIONS AND IT’S KILLING OUR BUSINESS.” The music industry fosters a caustic environment in which people face derision for not knowing answers to basic and complex questions alike. In the beginning of my career, I always felt afraid to ask what certain terms meant, thinking it better to learn through osmosis and observation or nod my head and grunt like I understand, then silently google the answer whenever it was safe. This practice creates all sorts of inefficiencies and insecurities, as uncertain people do worse work in the absence of answers that would enable them to simply be better. There may be stupid questions, but they are still worth asking if you don’t know the answers.
Plant seeds. In 2015, Take A Daytrip signed their first publishing deal with Universal Music Publishing Group. Our A&R was Jessica Rivera, a legend to the initiated because of her shoutout on Kanye’s “Last Call” (the closing song on College Dropout that immortalized her attempt to sign him to Def Jam early in 2000s). She taught me and the Daytrip guys that building towards goals is rarely linear, demanding countless invisible steps. She referred to this process as “planting seeds,” meetings that led to sessions, sessions that led to placements on albums, placements that opened doors into film, TV, and advertising, all the while creating narrative around the work the Daytrip guys were doing from one conversation to the next. She always had their big goals in mind, working backwards to lay out the little building blocks that could get them there. Of course, there is no guarantee that seeds sprout, but you don’t get very far without planting and tending them.
Pour faith and encouragement into creative people. In nearly 13 years of working in creative fields, I have often gotten the best results out of artists of all disciplines when I have granted them time, attention, and real support. Whether your friends, your clients, or your collaborators, you should know that anyone making art publicly has to muster the bravery to bust their work out of the prison of their mind, studio, or computer and share it with even one other person. No matter what that work entails, if you honor it somehow with your response and continue to provide faith, you’ll see amazing results. And remember, sometimes faith and encouragement mean learning how to be critical without undermining one’s will to make things.
“Create power by sharing power” - Jamal Joseph. A corollary to the concept of building horizontally. Jamal Joseph is a towering figure. A member of the Panther 21, the legendary cadre of Black Panthers who stood trial and won their freedom in the late 1960s. Tupac Shakur’s godfather and biographer. Former chair of the Columbia University Graduate Film School. Prison educator and activist. I had the profound privilege of calling Jamal a mentor and teacher, studying under him my final year of college and getting to know him beyond the bounds of his book-filled office as a true sage and artist. He never skimped on time. He never held back a secret. He always encouraged me to push farther, explore ideas without fear, simply do. “Create power by sharing power” comes from his staggering memoir Panther Baby. It is a credo worth attempting in every working and personal relationship you cherish.
True mentorship is a two way street. You will be the sum of many mentors, direct and indirect. You will learn in the process that you often teach them as much as they teach you. Education is not unidirectional. It is osmotic, transferring back and forth between the thin membranes of time and space that separate individuals from any two generations coming in contact with one another. Mentorship is not merely a function of age, it is about a willingness to share information, create opportunity, and learn from the mentee in equal measure. Mentors can, at times, be ungenerous, dogmatic figures, but any long-lasting mentor/mentee relationship is bilateral.
A deal is only as enforceable as the relationship it accompanies. Unless you want to go to court.
If you can have a real conversation, you can find a solution. Or, exhaust all options before litigation. Unless you really want to go to court.
Don’t let standards get in the way of what’s right or important. Few things make me angrier than when a lawyer or manager invokes standard or custom when telling me one of my clients can’t or shouldn’t have something they deserve. Sure, precedent matters, but, so often, people lean on it to move things along without having to critically reason through situations. As an example, simply because it is not a standard for songwriters not to receive master royalties doesn’t make it right, particularly at a time when the production and songwriting processes are often more deeply intertwined than in any prior era. Standards in an industry that is barely 150 years old are meant to be tested, reconsidered, and rewritten, especially when the facts on the ground change and old customs wilt in the face of new realities.
In any negotiation, understand the levers, the asks, and what you actually want. A powerful lawyer (the same “name in the firm’s name” type mentioned in the first iteration of this list) broke down publishing deals for me once. He said there are really only four things that matter. Money, time, terms, and splits. In greater detail: The amount of money you’re being given (upfront, in total, and for different purposes like travel and studio), how long the deal is, what specific conditions govern your satisfaction of the deal (whether in the form of a Minimum Delivery Commitment, which stipulates that you deliver a certain number of songs, or a Minimum Delivery and Release Commitment, which stipulates you must deliver a certain number of songs and they must be released in a commercial capacity), and the breakdown of how you and the publisher divide revenue from various sources. Of course, most publishing or record deals are typically tome-like documents that contain far more than these four pillars. The devil is surely in the details. Yet the longer I work in this business, the truer this advice proves. Focus on the important, core elements as you negotiate. Small details matter, but they tend to govern edge cases that rarely materialize. Understand that when you ask for one thing, you may have to give up another. Know what’s most important to you and what you’re actually willing to give up. If you have a clear sense of your absolute no’s in a deal, it is harder to get fucked.
A record deal/publishing deal is just the beginning. In the 2015 piece I wrote for Complex about the things I’d learned in my quaint two years in the music business, the one piece of truly enduring advice I hit upon was the notion that a record deal (any deal, for that matter) was a beginning and not an end goal. In the current industry climate, this notion has never proven truer. Back then, I wrote: “The money can be immediately life-changing, but advances don’t last. For emerging artists, a record deal provides an injection of capital and enhanced resources, human and otherwise. It also means that the artist must now focus even harder on perfecting his/her craft, on image and message, on consistently engaging fans, or conversely building a mystique that keeps the audience hooked and guessing. You sign a deal and very quickly come to realize that your public perception is a product, attached to financial projections and accompanied by certain expectations.” In the years since, these words have only proven truer, with TikTok stars like Addison Rae converting social media fandom into bubbling pop stardom, and artists like the Weeknd turning a parade of hit records into a kind of breathing, ever-expanding art project (for better or worse). To make matters more complex, though recorded music revenue has hit record highs year over year in the 2020s, labels and distributors alike have often turned conservative in their deal making when it comes to artists that don’t have “strong metrics.” So what we have now is a landscape in which major music companies throw big money at proven projects, even as known stars (a random smattering: Dua Lipa, Halsey, Justin Timberlake, Khalid, Lil Nas X, Childish Gambino) all released projects that struggled commercially within the past few years. At the same time, labels are afraid to take bets on relative unknowns who don’t have clear commercial histories, either offering small, “developmental” deals or passing on signings altogether. As I’ve written, many of the biggest recent success stories in the business are traditional artist development stories: Doechii, Sabrina Carpenter, Shaboozey, Chappell Roan. Artists who succeeded through experimentation, years of releases, touring, and constant reinvestment. Artists who were signed, dropped, signed again. Artists who serve as living reminders that a record deal is a milestone, but it is certainly not a final destination.
Avoid “we” when you mean “you.” This is a grammatical pet peeve that doubles as a lesson in accountability. I almost always try to avoid saying “we” when I mean “you” or “I.” In other words, if I want something done by a team member, I don’t say “what are we doing about this situation?” I say “you,” or I clarify that I will be handling said situation. This kind of verbal specificity, though seemingly small, clearly defines responsibility.
“You know artists.” If you work in music for even a short period of time, you will hear some variation of the phrase “you know artists” to explain away all sorts of behaviors. Lateness. Rudeness. Spaciness. Indecisiveness. Inability to handle normal everyday tasks. There are a few reasons I’ve tried to eliminate this phrase from my vocabulary over years of having heard and occasionally said it. First, artists are largely different. Genius is a kind of imbalance. Certain parts of a deeply creative person’s brain function with greater focus and energy than others. “You know artists” is an unfair broad brush that turns the same qualities we love into points of criticism when it’s convenient. Second, artists are human beings. They’re not aliens. They’re not playing by different societal rules. Many bad behaviors can be made better through conscious effort over time. “You know artists” lets too many people off the hook.
When management works, it’s invisible. When it fails, it’s the only thing visible.
Everyone is unreasonable and so are you. Any child who grows up to be a parent understands this principle implicitly. In any negotiation, particularly any contentious one, it can be all too easy to think of your adversary as unreasonable. You have a set of wants. They have a set of wants. The misalignment of those wants can conjure impressions of inflexibility, exploitation, deviousness, and dishonesty. The longer I have worked in music, the more deals I’ve negotiated, the more important I’ve found it to attempt to inhabit the perspective of the people with (or against) whom I’m negotiating. I still may disagree with them and their wants, but I find it helpful to look at any matter through an opposing vantage point. It’s not just empathy for empathy’s sake. It enables you to see moments in which you might be unreasonable and to also understand holes in your own justifications. It’ll also probably stop you from cursing people out and raising your blood pressure, even if they deserve it.
This business is simple, but it isn’t easy.
As I am needed, so I am. Management (and, increasingly, all service work in music whether that of the manager, the A&R, the marketer, the producer, the songwriter, the publicist, etc.) often demands meeting the need of the moment, no matter what the moment entails. It requires constant adaptation and learning, development of new relationships and ways of seeing, an appetite for change even as you try to stay steadfast in your core principles and ideas. The phrase “As I am needed, so I am” came to me one day in an attempt to encompass what it means to be a manager, to have to show up in different ways for other people on a daily basis.
Make the nine to get to the one. One of my earliest bosses was a producer named Tricky Stewart. Responsible for some of the defining records of the 2000s, Tricky lived in Los Angeles at the time. He rarely visited our New York office, preferring to stay close to the creative heart of the industry which had resituated out west by 2013. When he did come east, I tried to soak up as much game as possible. One day, sitting in his office between meetings, I asked what his process was for making music. Did he refine things endlessly? How did he know when something was done? He told me he’d make nine terrible ideas, just to get to one incredible one. He practiced brisk iteration, unafraid of trash in pursuit of gold. It’s classic creative advice, but well worth remembering in a field that is driven by a highly irrational product that has to feel good.
Getting paid a lot to do something you don’t normally do can be worse than getting paid less to what you do normally do. If you can get someone to pay you for your passions and strengths, you’ll rarely feel trapped by deals you do. Even if you struggle at times or don’t feel properly compensated, you will not feel out of step with your creative core. Conversely, the farther from your zone of interest you stray in pursuit of a check, the more likely you are to feel friction between your true self and the self that is grinding away in attempts to satisfy the requirements of a deal. Of course, there are times when you must do creative work you don’t love to make ends meet. That’s unavoidable, even when you’ve reached new plateaus in your career. You should always assess what’s important to you in any situation. To paraphrase Baby Keem, always consider the pros and the cons of the next check.
“Stay close to talent” - Mark Stewart. Returning to my first job. Tricky Stewart had a brother, Mark. Mark ran the A&R department with Tricky. His office shared a wall with mine, the closet they’d given me with speakers and an aging PC. Mark always had time for me, excited to share music, talk shit, and tell stories. He also managed Tricky, a partnership rooted in their brotherhood, bonded further by many years of hit records. When I asked him how I could become a manager, he said, “stay close to talent.” At the time, I thought, “that’s fucking rich, your primary client is your brother.” Over the next few years, I realized how sage that advice was, as one talented person introduced me to another, as studios, galleries, and film sets became crucibles for meeting and eventually working with new creative people. It was advice that sounded too simple to be true, but an aphorism I still follow and share to this day when asked the same question.
Beware the “no” that masquerades as a “yes” (or being yes’d to no). I work with an artist who has maintained a philosophy of staunch independence throughout his career. At a critical crossroads between albums, we discussed the idea of doing a record deal with a major label. We wanted more resources. We wanted better infrastructure. We wanted to make the next album as big as possible. We also knew we didn’t want to do a deal that economically disadvantaged him long term or limited him creatively, two toxic hallmarks of major label deals. As an exercise, we conceived a deal no one was likely to entertain. We imagined most labels would dismiss us out of hand. Anyone that went for it would be showing real belief in the project. We shopped it to interested A&R’s. As expected, most balked when we told them what we wanted. One A&R bit. He said he’d take it back to his boss. He seemed excited. When he returned months later, he said he couldn’t do what we’d asked for, but he could do something close. We went along with it. When we finally got a firm offer, fine print made it very far off from both what we’d proposed and what we thought we were being offered. Whenever we’d get on the phone to discuss changes, we would be told they were coming. We’d receive a new draft of the deal. Some changes we’d requested would appear, but other changes that worsened the deal or negated things we’d asked for would also appear. At no point were we ever explicitly told “no,” yet “no’s” kept appearing all around us, masked by “yes’s”. This sort of negotiation happens all the time in entertainment, on levels big and small. It can happen when you ask for a small favor, receive a “yes,” then never hear back from the person you asked. It can happen in a multi-million dollar record deal negotiation. Learn how to discern when “yes” actually means “yes” and when it means “no” and you’ll slice through a ton of bullshit.
Some clients prefer the wires hidden, some want to know how everything works. As anyone who represents talent, it’s your job to figure out which personality type defines your client, then build structures around them that lean into their specific desires.
Beware the accumulation of novelty, the novelty of accumulation. It can be easy to experience something new, attain some new height, or acquire some new toy and feel fantastic. The thrill of unfamiliarity. The excitement of freshness. The joy of learning something different. The adrenaline infusion of the latest thing wears off fast. This concept certainly applies in life, but proves especially toxic in the business of music, so driven by interpersonal relationships. Managers with clients. A&R’s with signings. Producers with gear. Anyone who comes into money and buys fancy things. This kind of accumulation can make you feel temporarily whole, but that feeling rarely lasts. This notion—the accumulation of novelty, the novelty of accumulation—is a cycle. As one new thing fades, the urge to acquire resurges, as if the next wave of more will make up for the gap left by the low tide of old achievement.
Don’t buy too heavily into your own myth.
Sometimes, just do nothing. You’ll be shocked by how many times a situation will simply work itself out. Knowing when to do nothing is an art learned through time, failure, and reflection, but it is a key to survival, success, and happiness.
The original 39 lessons and observations below...
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.
This was great Jon! Such a dope read.
For an old geezer like me to find so much wisdom, good advice and life experience from one so young is humbling. Thanks, Jon. Look forward to checking in again next time.