The Diary Of A CEORick Rubin: What Jay-Z Did in 30 Minutes Left Me Speechless!
The Diary Of A CEO
How Jay-Z Wrote 99 Problems 0:00
Jay-Z worked differently from every other rapper Rick Rubin ever recorded. Where other artists spent hours writing lyrics on paper, Jay-Z never seemed to write anything down. When Rubin played him the beat for 99 Problems, Jay-Z simply asked him to loop it over and over while he sat in the back of the room, mumbling and humming to himself. After twenty or thirty minutes he announced he had it, went into the vocal booth, did about three takes, and picked the best one. The song came together entirely in his mind before it ever touched paper.
Ordinary People Who Made a Decision 0:30
Rubin has worked with an enormous range of artists, from Jay-Z and Kanye West to Adele, Justin Timberlake, Mick Jagger, and the Red Hot Chili Peppers. Asked why these people seek him out, he points to his forty years of making things, starting as a hobby that grew into a career. He insists the artists on that list are not special in some innate way but ordinary people who made a decision to commit fully. He cites Eminem as someone who writes constantly simply because he wants to be the best possible version of himself, driven by an almost obsessive standard.
Creativity Gets Beaten Out of Us 1:00
Rubin rejects the idea that some people are just born more creative. He argues creativity is worn down over a lifetime by school and institutions that teach people to follow rules and repeat back what they're told rather than think freely. He says these rules exist to control people, not to help them, and he calls for breaking free of that conditioning. He believes every meaningful creative act involves risk, and that something has to die first, a lifestyle, a career path, a relationship, before real growth can happen. He also mentions his own depressive episode in his early thirties, when he felt the rug pulled out from under him, suffered panic attacks, couldn't sleep, and describes it as feeling shot with a poison arrow.
Defining Himself Through Art 2:32
When asked how he identifies professionally, Rubin says he is involved in art and creativity, sometimes as a coach, sometimes as a collaborator, sometimes helping with a film project or advising a startup. He believes almost any problem, whether creative or business, has a creative path toward improvement, and that the commonly accepted way of doing things is often just another limitation in disguise.
The Idea of Indefensible Work 4:00
Rubin introduces the word indefensible as a guiding principle in making art, meaning something taken to such an extreme that it can't be rationally justified. He says he leans toward intuition and a kind of guidance from the universe, which he personally calls God, rather than reason. As an example, he describes how a meme linking his image to the term vibe coding, coined by Andrej Karpathy, kept appearing to him from multiple directions until he felt compelled to respond, first with a joke tweet that unexpectedly got a million and a half views, and then by setting aside his professional work to write an entire book on vibe coding, without being able to explain why.
Risk Over Popularity 9:32
Rubin says the most interesting art is often challenging on first encounter, and that revolutionary work tends to arrive without context, which is why people may not like it immediately. He points to Kanye West's Jesus Is King as an intentionally anti-hip-hop album that took time to appreciate, and to Radiohead's Kid A, which he initially disliked after loving OK Computer but has come to consider his favorite Radiohead record. He contrasts this with Lincoln Park, who broke from their earlier rap-rock sound years into their career; the choice split their audience but set them up for a longer creative life instead of riding out a dying genre.
Never Considering the Audience 16:31
Rubin says he never thinks about near-term incentives, chart performance, or what a record label wants. Every project is treated as a diary entry, a personal true expression that either resonates with someone or doesn't yet. With 99 Problems, the president of Def Jam, the label Rubin himself founded, said the track would never be a single because it didn't sound like radio, yet it became a defining hit precisely because it didn't sound like everything else. A similar story unfolded with System of a Down, whose song Sugar was rejected outright by a major rock station before becoming its most requested track within a year, and the band later sold out an 80,000 seat stadium in Paris two nights running.
Meditation as a Grounding Practice 20:30
Rubin learned transcendental meditation, or TM, at age fourteen, and describes it as a mantra practice done silently with closed eyes, using a private sound given by a teacher that he has never spoken aloud or shared with anyone. He practiced twenty minutes twice a day, often meditating alongside artists like Tom Petty, Johnny Cash, and the Red Hot Chili Peppers before studio sessions. He stopped during college, then resumed in California, and found the depth of connection was still there even after years away, comparing consistent practice to making deposits in a bank, a phrase he attributes to Maharishi Mahesh Yogi. He describes its effect as letting go of ordinary concerns and seeing beneath the surface of things, and calls the creative process fundamentally spiritual rather than intellectual.
Working from Inside Out, Not from the Customer 27:01
Rubin draws a contrast between his own approach and the standard business advice of starting with the customer's problem and working backward to a solution, as companies like Amazon are known to do. He notes that Jeff Bezos bets on things unlikely to change, such as customers always wanting faster delivery. Rubin argues his own method is the opposite: making what excites him personally, without asking what an audience wants. Yet he points out Amazon itself lost money for about twenty years and was considered a poor investment until it wasn't, suggesting its success came from doubling down on a belief despite the metrics, which he sees as fundamentally the same instinct as his own creative approach.
Feeling over metrics 30:00
You ask whether it helps to measure creative success with data, and the answer is no. What matters is an internal feeling and how a piece lands when you share it with someone, whether it genuinely lights them up. Two things can look equal by the numbers, yet one of them excites you and the other merely does the job, and over the long run the one that excites you is the one you will keep supporting.
Believing you are not good enough 32:30
A major block to creativity traces back to childhood moments, like being told as a kid that you cannot sing, which then lodges itself in you for life. Everyone is creative, but many people never make creative choices because they were given bad information about themselves early on. The word creative gets misapplied too, treated as something only certain people or activities qualify for, when really it describes a way of engaging with anything, even an Excel document.
Comparison is pointless 34:01
Ranking artists against each other is treated as normal, but comparing Michael Jackson and Prince, or Kanye West and Drake, misses that they do entirely different things and give you entirely different experiences. The whole idea of competition between artists comes down to arguing over whose diary entry is better, which does not really make sense. Deciding who is more creative is left entirely up to you as the listener, not something to be settled objectively.
Deadlines and phases of creativity 36:01
Deadlines only get set once a project already feels cracked, roughly ninety percent finished, so the deadline only governs the small remaining polish rather than the core work. Before that point, creativity moves through phases: a seed phase where you try many things without knowing what they will become, an experimentation phase where you discover what the seed wants to be, a crafting phase where you shape it, and finally a finishing phase. None of these phases can be rushed onto a timeline, because until you have passed through them you genuinely do not know what you are making.
Risk, failure, and paying the bills 41:00
Pursuing what you love can mean losing friends or facing people who think you are strange, and that risk is real and worth taking. At the same time, it is fine to keep a job that pays the bills while pursuing a creative passion rather than forcing the passion to also be the income source. This was the original plan with music, expecting a regular day job while making music purely out of love, before it unexpectedly became a career on its own.
Working with artists through listening 44:31
Rather than persuading artists toward a direction, the approach is to ask what they hope to accomplish and support that process, listening closely the way a good therapist does. Artists often arrive knowing exactly what they want, then say they have no idea and ask for help, revealing a barrier to hearing themselves. Most people are rarely listened to deeply, and simply being heard lets someone find their own answer, similar to choosing which of two pieces of pizza tastes better to you personally, not which one you think others would prefer.
Backing people, not just products 49:00
A venture capitalist friend said that when investing, it is always about the founder rather than the specific business idea, and the same logic applies to artists. The Strokes were turned down twice, roughly fifteen and twelve years ago, because the demos did not reveal a clear path forward, even though that did not mean the work was bad. Years later a rough twenty second voice note demo carried enough potential to say yes, describing the decision as a felt knowingness rather than something that can be explained or calculated.
Living without fixed goals 51:30
Personal goals are absent entirely, replaced by moving forward based on the information available and accepting that impermanence is real, illustrated by losing a Malibu house and all its possessions in a fire eight years ago. Instead of planning a route the way a satnav sets a destination, the approach has long been to simply drive without a plan, sometimes literally, during rare days off from long studio sessions.
Choosing to start a new life 54:00
A story is told about a very successful but deeply suffering artist who was reassured that success meant he was not obligated to keep living the way he had been, that he could walk away and live simply on a beach instead. Years later that same person confirmed he had remembered and eventually done exactly that. People who consider suicide often feel boxed in by choices already made, a career, a relationship, a lifestyle, and mistake the need for that situation to end with a need for their body to end, when really it is possible to leave the table, like stepping away from a game of chess, and start an entirely different life instead.
Boxed in by our own stories 1:00:00
Rick talks about how people trade parts of themselves for identity and status, and end up feeling stuck as a result. He insists this feeling of being trapped is really just a story we tell ourselves, not a fact, and that we are free to start over at any point if we choose to.
Visiting a friend after a suicide attempt 1:00:32
Rick recalls visiting a close friend in the hospital after a suicide attempt, where visitors before him treated the moment like a death. Instead, he told his friend he was in the sweet spot, that he had hit a reset button, and that none of his old obligations still applied. The friend reacted, got up, got dressed, and the two had a real conversation, which Rick describes as an amazing experience showing how much of our sense of being boxed in is just a story.
How to actually hit reset 1:03:00
Asked for a first step toward change, Rick says to identify what you truly want different in your life and find the cleanest way to change it, whether that means leaving a job or a relationship. He argues commitments are good to make and keep, but when a relationship has gone bad, such as living with an alcoholic partner, staying locked in does nobody any favors, and love only works as a two way pull, not one sided.
His depressive episode at 33 1:07:30
Rick describes a business dispute at 33, when a new executive he had no relationship with challenged an agreement he had with his mentor. Having never faced instability before, he had panic attacks, couldn't sleep, and felt physically sick, describing it as being shot with a poison arrow. He went to therapy, eventually used an antidepressant, and says the crisis permanently changed him, making him feel less like Superman but more grounded, and better able to understand the personal struggles of the artists he works with.
Point of view and hard work in art 1:14:30
Rick says what great artists share is a distinct point of view, a way of seeing something ordinary that others haven't noticed, similar to what a good comedian does. He stresses that talent alone isn't enough, great work also demands intense work ethic, since the field is crowded and competitive even without direct rivalry.
Where interesting perspective comes from 1:17:01
To sharpen your own point of view, Rick suggests looking outside business and self help material, toward museums, great literature, and great films, since fresh ideas often come from unrelated fields. He references Steve Jobs's love of typography as an example of a skill combination no one would have prescribed for a computer programmer.
Lessons from the Dao and Jung 1:19:01
Rick describes reading the Dao decades ago and finding it read as a completely different book each time he returned to it, inspiring his own adaptation for coding. He highlights the idea that the soft overcomes the hard, illustrated by water slowly wearing down rock, and by a story about Napoleon delaying decisions two weeks so problems could resolve themselves. He also praises Carl Jung's ideas on archetypes and synchronicity as closer to how the world actually works than science admits.
Trusting an inner sense over rationality 1:22:00
Rick argues that science only describes how things appear until the next breakthrough overturns it, and that there is an inner knowingness, like sensing you want to be near someone, that data can't explain. He suggests overly rational, metrics based thinking can be a curse, and that learning to trust that inner antenna, rather than letting it go rusty from disuse, opens up more of life.
A generative force behind creativity 1:25:02
Rick describes sensing a higher creative intelligence behind life, similar to what makes plants grow, that isn't aimed personally at anyone but can be ridden like a wave. He says this feeling guided him toward the Dao adaptation project even though it seemed indefensible at first, because he felt asked to participate in something larger than rational sense could justify.
AI as a powerful, dangerous tool 1:27:31
Turning to artificial intelligence, Rick compares it to fire or the printing press, a wildly powerful tool that can do real good and real harm depending on use. He notes growing public unease, including a friend outside tech worried about job loss, and an AI researcher's warning of serious existential risk.
Can AI actually be creative 1:29:01
Rick doubts AI has genuine creativity because creativity depends on a distinct point of view, while AI only recombines existing ideas and can give different answers to the same question on different days. He compares a possible use case to old hip hop crate digging, where you might sift through thousands of AI generated tracks to find one usable fragment, but doesn't think it will fully replace the artist.
AI as a creative tool 1:31:00
Rick Rubin suggests that AI could let people who don't see themselves as artists still create something beautiful through prompting and iteration. He raises the recurring debate about whether AI can be creative, and pushes back on the idea by pointing out that what people call great creativity is often really the whole story around a song, the artist's history, their record deal, and the audience following them, rather than the output itself.
The prompt is the creativity 1:33:00
Rick argues that the real creativity lies in the idea, not in the finished product. He points to Alfred Hitchcock, who storyboarded entire films in advance so the movie already existed on paper, and to Wes Anderson, who mocks up his films frame by frame before actors are involved. In both cases the prompt, the instruction given to others, is where the creative act happens, and AI could serve as a tool for that kind of mocking up.
Barrier to entry and what still matters 1:35:31
Rick notes that prompting is easy to learn, so the barrier to making things has dropped sharply. He argues that what separates a great artist from a lesser one stays the same regardless of the tool: whether the work changes your life, moves you, and makes you want to experience it again and again. He shares a personal story of loving a Spotify song for two months before discovering it was AI made, and admitting that once he knew, he liked it less, suggesting something irreplaceably human affects how art resonates.
Andy Warhol and hidden hands 1:37:02
Rick uses Andy Warhol's shift from painting to screen printing images like Marilyn Monroe and Elvis as proof that authorship isn't about who physically makes the work. Warhol directed the process without touching the canvas, and it was still considered fully his art. Rick draws a parallel to Renaissance studios, where masters like Rembrandt may have painted only part of a canvas while assistants did the rest, and to modern records where studio musicians play instead of the credited band, all without diminishing the work's value.
Miracles in the studio 1:40:30
Rick describes a session with a brothers duo recording a song called No Hard Feelings, where nothing had changed on paper but suddenly the performance became extraordinary, and he felt afraid they might not make it to the end and lose the moment forever. He also recalls a week recording with Neil Young that felt like a total failure, only to have drummer Ralph suggest replaying last week's tape with small adjustments to bass and piano, revealing that the magic had been there all along despite the mistakes. Rick concludes that none of this is repeatable in a formula sense; the only repeatable part is showing up and continuing until the work becomes great.
Trusting the work's own direction 1:44:01
Rick describes recording Johnny Cash informally in his living room, just to get to know him and hear his favorite songs, with no plan to release anything. Later, polished studio versions with full bands never matched those raw living room takes, so those original recordings were the ones released. He says a piece of work sometimes reveals through the process that it wants to be something entirely different from what was planned, and once he decides he likes something enough to share it, he lets go of caring how the world responds.
Making art as an offering 1:49:02
Rick explains that he no longer thinks of studio work in terms of charts or singles, but as an offering to God, calling numbers and metrics insignificant next to that intention. He recalls realizing this a few years ago while sitting in a lifeguard chair in Hawaii, describing it as a quiet epiphany that reframed decades of work he had done without fully understanding why. He clarifies this is meant literally, that the art is a gift to a higher power he calls the father, not a transaction with a customer, and that other people's approval is simply a bonus, not the point.
Consciousness and self-expression 1:52:31
Rick connects his idea of art as offering to a bigger claim: that people exist to show who they are and to self-express, comparing notes with others to see where their views align or differ. He responds warmly to a story about a physicist who suggested that consciousness might have divided itself into every person and creature so it could explore and understand itself, saying the idea does not strike him as strange at all.
Jay-Z and the Ace of Spades story 1:54:00
Rick tells the story behind Jay-Z's champagne brand, drawn from their eight part documentary premiering September 18th. Jay-Z had popularized a rival champagne, Cristal, until its head made disparaging comments about hip hop drinkers, at which point Jay-Z pulled it from his clubs entirely without any plan to profit from the decision. Shortly afterward, someone approached him with an existing bottle design and the chance to start his own brand, Ace of Spades, which he eventually sold for 630 million dollars, and Rick frames this as evidence that acting on principle, without calculating personal benefit, tends to be met by the universe stepping in.
Quitting as the first step 1:59:30
Rick and his interviewer discuss how culture glorifies starting new ventures but rarely acknowledges that quitting something first is often the necessary step, since Jay-Z's brand could not have existed without him quitting Cristal. Rick brings up a senior tech executive he recently spoke with who is stepping down for personal reasons of conscience, worried people will assume he was fired, illustrating how rare and uncomfortable it is for people at that level to walk away voluntarily.
Supporting an Artist's Choice 2:02:00
Rick explains that if someone truly believes a piece of work is great, he will support them putting it out, even if he personally doesn't like it. He recalls working with an artist who included a song that felt out of place with the rest of the material, and that song went on to become a big hit. He says his opinion of whether something is good is only ever true for himself, comparing it to disliking a pizza, and he mentions turning down the chance to produce Guns N' Roses' first album after seeing them play to a small crowd, deciding it wasn't the right fit for him.
Talent Alone Isn't Enough 2:05:30
Rick says it is entirely possible to be a great creative and never achieve commercial success, and that this is probably more common than the reverse. Success depends on far more than talent, he says, since many things beyond a person's control have to align. He suggests that for some genuinely talented people, success simply may not be part of their path, calling it possibly a karmic matter.
Jay-Z's Unwritten Process 2:07:00
Rick describes what made Jay-Z different from every other rapper he worked with: Jay never physically wrote lyrics. When Rick played him the beat for 99 Problems, Jay sat silently for twenty or thirty minutes, occasionally mumbling, then went into the booth and performed the entire first verse from memory, with no lyrics on paper. Each take kept the same words but shifted the cadence and emphasis, the way a saxophonist varies a solo. Rick calls this an unusual and specific skill, since rap lyrics are far more complex to memorize than a typical song verse.
No Single Right Process 2:12:02
Rick warns against taking advice too literally, since people offer guidance based on their own story, not yours. He suggests immersing yourself deeply in whatever medium you're working in, then listening closely to your own internal compass, since there may be no single right answer, only the right answer for you. He also talks about separating your own wishes from voices absorbed from parents or outside influence, describing how it took him roughly a year after leaving home for college to distinguish his own thoughts from his parents'. He recommends grounding practices like meditation or therapy to build that self-understanding, calling it slow, difficult work with no quick fix.
Fearlessness and Risk in Art 2:17:32
Discussing Kanye West, Rick says what sets him apart is total fearlessness in art and in life, calling it a rare strength. Rick argues that risk and greatness go hand in hand, comparing the creative process to walking a tightrope where the only way to reach something truly great is to risk falling. He adds that everyone has the potential to become the best version of themselves, even if that doesn't mean becoming the best in the world at what they do.
Obsession Behind Greatness 2:21:01
Rick describes the people he's worked with, from Justin Timberlake to Jay-Z to AC/DC, as ordinary people who made a decision and, in some cases, cultivated a gift rather than being born with it. He points to Eminem as an example, someone who writes constantly, filling notebooks that are mostly never seen by anyone, purely to keep improving, comparing it to an athlete who trains hard in the offseason.
Artists Who Changed Him 2:23:01
Asked which artists fundamentally changed him, Rick names Johnny Cash, whom he describes as humble, quiet, and spiritually inspiring. He then describes Tom Petty as the ultimate craftsman, comparing him to Paul McCartney's ability to construct and understand every part of a song, and recalls spending two and a half years making the album Wild Flowers, learning patience and the importance of every vocal being perfectly in time and understandable. He also praises Adele and Shakira for writing their own songs, calling Adele almost mythical for being able to deliver a great take again and again.
Making a Documentary About Jay-Z 2:31:30
Rick explains that after making a documentary about Paul McCartney's musicianship, which he felt had been overlooked in favor of stories about Beatlemania, he began thinking about who else was misunderstood in a similar way. That led him to Jay-Z, who today is mostly seen as a billionaire businessman rather than as the poet Rick believes he fundamentally is.
The Long Road to Jay-Z's Documentary 2:34:00
Rick Rubin explains how the idea for the Jay-Z documentary began. He shared the concept with Jay-Z, focusing on revealing the lyricist and poet behind the fame, since most people never see that side of him despite it being the reason for his success. Jay-Z liked the idea but wouldn't commit right away, saying he needed time to think. A year passed without follow-up. A friend advised Rick to simply call and ask directly rather than wait for Jay-Z to bring it up, and Rick admits he still waited six to eight months out of discomfort before finally reconnecting, at which point Jay-Z agreed to move forward. The finished project surprised viewers with its unconventional style, including black and white color grading and unusual camera angles, which made it feel like an intimate, private conversation rather than a typical interview, giving audiences a rare, honest glimpse of who Jay-Z really is.
The Strange Story of 78 Chapters 2:37:01
Discussion turns to Rick's book, described as more of a philosophy book than a creativity guide, organized into what he calls areas of thought rather than chapters. He recounts how the book evolved from 1,400 pages of unorganized ideas into a structured form, originally landing on 63 areas of thought, then growing to somewhere in the low 80s. Wanting a number tied to something meaningful, he decided he wanted exactly 78, matching the number of tarot cards, since numbers like 78, 108, and 144 held significance for him. His collaborator Neil thought this was an unnecessary, even irrational demand after eight years of work. The next day, without anyone consciously removing anything, the sections were counted and there were exactly 78, a mystery nobody could explain.
Gratitude, Family, and Childlike Wonder 2:42:32
Asked who he'd call to apologize, Rick says he rarely uses the phone and can't think of an outstanding apology to make. Instead he'd rather call to say thank you, choosing his wife Mutasi or his son. He describes 15 years with his wife spent almost entirely together, rarely apart, and reflects on fatherhood as deeply joyful, watching his son experience wonder and occasionally surprising him with unexpected wisdom. He connects this to the book's idea that children remind adults what creativity truly is, since young kids haven't yet been told what they can't do and still see the world with awe, which he says is the same perspective held by great artists who find ordinary things breathtaking.
AI-generated summary. It can be wrong or incomplete - check anything that matters against the original.
