Born Standing Up – Steve Martin

Born Standing Up by Steve Martin
Date read: 10/18/23. Recommendation: 9/10.

Steve Martin details his early years, influences, and the lightning strike of his stand-up success that was decades in the making. I love studying people who you can tell are doing what they believe they were meant to be doing. Martin is certainly one of them. His story resonates on many levels—finding something that feels true in childhood, taking risks to eliminate a nagging sense of what if, imitating your way to originality, struggling to find consistency, and eventually reaching a place where your craft no longer serves you like it once did and relearning how to find your way forward. Entertaining, insightful, and one of the best comedic biographies out there.

Check out my notes below or Amazon for details and reviews.

My Notes:

Influences:
TV had a huge influence on Steve, it’s where he found Laurel and Hardy, who were clever and gentle. That’s where he learned that jokes are funniest when played upon oneself. He watched Jack Benny’s variety show and learned how funny a slow burn was. He would watch The Red Skelton Show and memorize Red’s routines and perform them the next day during “sharing time” at grade school. 

Disneyland:
Summer of 1955, Disneyland opened in Anaheim, CA. They were hiring kids Steve’s age to sell guidebooks on weekends and during the summer in the park. Steve pedaled his bicycle two miles to Disneyland, was pointed toward a souvenir stand a few steps inside the main gate, spoke with a vendor named Joe, and got the job. He was issued a candy-striped shirt, a garter for his sleeve, a vest with a watch pocket, a straw boater hat, and stack of guidebooks. They were sold at 25 cents each and he received two cents per book. Earning up to two dollars every day. They were sold in the morning when people poured through the gates. By noon he was done but didn’t have to leave, had free admission the the park. Became a regular employee at age 10.

As he wandered Disney and found shortcuts and hidden treasures, two places captivated him. “One was Merlin’s Magic Shop, just inside the Fantasyland castle gate, where a young and funny magician named Jim Barlow sold and demonstrated magic tricks. The other was Pepsi-Cola’s Golden Horseshoe Revue in Frontierland, where Wally Boag, the first comedian I ever saw in person, piled a hilarious trade of gags and offbeat skills such as gun twirling and balloon animals, and brought the house down when he turned his wig around backward. He wowed every audience every time.” SM

“Here I had my first lessons in performing, though I never was on the stage. I absorbed Wally Boag’s timing, saying his next line in my head…I studied where the big laughs were, learned how Wally got the small ones, and saw the tiny nuances that kept the thing alive between lines. Wally shone in these performance, and in my first shows, I tried to imitate his amiable casualness.” SM

“Merlin’s Magic Shop was the next best thing to the cheering audiences at the Golden Horseshoe. Tricks were demonstrated in front of crowds of two or three people, and twenty-year-old Jim Barlow took the concept of a joke shop fay beyond what the Disney brass would have officially allowed…I loitered in the shop so often that Jim and I became buddies as I memorized his routines, and I wanted more than ever to be a magician.” SM

“With any spare money I had, I bought tricks, memorized their accompanying standard patter, and assembled a magic show that I would perform for anyone who would watch, mostly my parents and their tolerant bridge partners.” SM

At age 15 (August 1960), a job opened up at the magic shop and Steve got the gig. “I stood behind a counter eight hours a day, shuffling Svengali decks, manipulating Wizard decks and Mental Photography cards and performing the Cups and Balls trick on a rectangle of padded green felt. A few customers would gather, usually a young couple on a date, or a mom and dad with kids. I tried my first jokes—all lifted from Jim’s funny patter—and had my first audience that wasn’t friends or family.” SM

As he demonstrated tricks 8-12 hours/day, started to improve, channeling his impression of Jim. 

Later a man named Dave Steward took over as manager of Merlin’s, a former vaudeville performer, whom Steve learned a lot from. Like his opening joke, the glover into dove trick where he threw a white magician’s glove into the air, it hit the floor and lay there, he stared at its then went onto his next trick. First time Steve had seen laughter created out of absence so he borrowed this and used it in his own routine. 

Steve learned to throw everything at the audience, costumes, lights, music, everything. But originality was not yet on his mind. He started to lean more into comedy, because that seemed to have a clearer path forward, like Stan Laurel, Jack Benny, or Wally Boag. And advanced magic tricks cost too much. 

Knott’s Berry Farm:
At age 18, Knott’s Berry Farm needed entertainers with short acts. Steve auditioned with his thin magic act at a small theater and got the job at the Bird Cage Theatre. 

“At the Bird Cage, I formed the soft, primordial core of what became my comedy act. Over the three years I worked there, I strung together everything I knew including Dave Steward’s glove into dove trick, some comedy juggling, a few standard magic routines, a banjo song, and some very old jokes. My act was eclectic, and it took ten more years for me to make sense of it. However, the opportunity to perform four and five times a day gave me confidence and poise.” 

Over time learned it was not magic he was interested in but performing in general. 

Evolving beyond imitation:
Eventually, in his early 20s, realized how important originality would be and that comedy could evolve. “I would have to write everything in the act myself. Any line or idea with even a vague feeling of familiarity or provenance had to be expunged. There could be nothing that made the audience feel they weren’t seeing something utterly new. This realization mortified me. I did not know how to write comedy—at all. But Id did know I would have to drop some of my best one-liners, all pilfered from gag books and other people’s routines, and consequently lose ten minutes from my already strained act…After several years of working up my weak twenty minutes, I was not starting from almost zero.” SM

Started testing his concept of creating tension but never releasing it. No formal punch lines. What would audience do with all that? They’d eventually have to pick their own place to laugh out of desperation. 

Also gave himself a rule: “Never let them know I was bombing: This is funny, you just haven’t gotten it yet. If I wasn’t offering punch lines, I’d never be standing there with an egg on my face. It was essential that I never show doubt about what I was doing.” The act would go on with or without them. 

Taking the leap:
“I concluded that not to continue with comedy would place a question in my mind that would nag me for the rest of my life: Could I have had a career in performing?” SM

Writing career:
In 1967, landed a writing job on The Smothers Brothers Comedy Hour. Started painfully and was uncomfortable contributing anything of his own. He faced pressure to deliver, was unsure of himself, and felt doubt from other professional writers on the show. One afternoon was asked by Tommy Smothers to write an intro for a sketch dealing with television. Steve went upstairs to his office and couldn’t come up with anything. Suddenly a line occurred to him, but it belonged to his roommate, comedian Gary Mule Deer. Steve called him and got his approval to use it. Then he went downstairs, handed the line to Dick Smothers: “It has been proven that more Americans watch television than any other appliance.” Two highly experienced writers came up and asked if he wrote that joke, he said yes, and they said good work. Afterward, he was much more relaxed and able to contribute more to the show. 

Early Act:
In the early days (1960s), Steve’s act was a catchall, cobbled together from juggling, comedy, folk, banjo playing, weird bits he’d written in college, and magic tricks.

With practice, Steve’s act became more physical. Singing, dancing, etc. “My teenage attempt at a magician’s grace was being transformed into an awkward comic grace. I felt as though every part of me was working.” SM

“Between 1973 and 1975, my one-man vaudeville show turned fully toward the surreal. I was linking the unlinkable, blending economy and extravagance, non sequiturs with the conventional.” SM

Consistency:
“It was easy to be great. Every entertainer has a night when everything is clicking…What was hard was to be good, consistently good, night after night, no matter what the abominable circumstances.” SM

After years on the road, now had four hours of material to pick and choose from. 

Hitting his stride:
Dave Felton, Rolling Stone, on Steve’s act: “This isn’t comedy; it’s campfire recreation for the bent at heart. It’s a laugh-along for loonies. Disneyland on acid.”

His audience developed more like that of a rock-and-roll band than that of a comedian. 

“This lightning strike was happening to me, Stephen Glenn Martin, who had started from zero, from a magic act, from juggling in my backyard, from Disneyland, from the Bird Cage, and I was now the biggest concert comedian in show business, ever.” SM

When he started playing arenas, he could no longer experiment. Eventually, he lost touch with what he was doing and suffered an artistic crisis. Walked away from stand-up and never did it again. 

Film:
Determined to parlay his success from stand-up into motion pictures. 

Carl Reiner’s influence: “His memory was sharp as cheddar, and he would spontaneously relate anecdotes relevant to our work.” SM

The world of moviemaking had changed me. Carl Reiner ran a joyful set. Movies were social; stand-up was antisocial. I was not judged every day by a changing audience. It was fun to have lunches with cast and crew and to dream up material in the morning that could be shot seven different ways in the afternoon and evaluated—and possibly perfected—in the editing room months later.” SM

“I got another benefit: my daily observation of Carl Reiner. He had an entrenched sense of glee; he used humor as a gentle way of speaking difficult truths; and he could be effortlessly frank. He taught me more about how to be a social person than any other adult in my life.” SM

Personal History – Katharine Graham

Personal History by Katharine Graham
Date read: 3/4/23. Recommendation: 10/10.

The best autobiography I’ve ever read. Graham tells her own story with honesty and candor. She reflects on how she built her own strength and self-confidence navigating a business world dominated by men while leading the Washington Post through its crucible moments of the Pentagon Papers, Watergate, and the pressmen’s strike of 1975. The Post not only endured but thrived, elevating its position among the most respected newspapers in the country thanks to Graham’s dedication to serving the public good, her ability to make tough decisions, and her commitment to upholding high journalistic standards.

Check out my notes below or Amazon for details and reviews.

My Notes:

Upbringing:
The children were an afterthought to Katharine’s mother, Agnes. She rarely mentioned them individually. The first time Katharine appeared in her diary by initial was two years after her birth. 

“My difficulties were much more tied to a lack of guiding personal relationships, for I had more or less to bring myself up emotionally and figure out how to deal with whatever situations confronted me. At the same time that I was surrounded by extreme luxury, I led a life structured and in many ways spartan, circumscribed by schools and lessons, travel and study.”

“My mother’s effect on us was often contradictory. We received every encouragement for what we accomplished, yet her ego was such that she trampled on our incipient interests or enthusiasms. If I said I loved The Three Musketeers, she responded by saying I couldn’t really appreciate it unless I had read it in French, as she had.”

Between fourth and fifth grade, she spent the entire summer by herself reading nearly 100 different books on the third floor of Mount Kisco. 

Self-esteem:
Upon graduating high school: “I still felt fairly different and shy and believed I had only a few friends. Apparently my class didn’t see me the way I saw myself. My senior yearbook entry describes a girl known for her laugh and manly stride. My class prophecy read: ‘Kay’s a Big Shot in the newspaper racket.’ But I envisaged no such future for myself or, in fact, any specific future at all. Rather than creating my own way, what I was trying to do all the time was figure out how to adjust to whatever life I found.” 

After departing for college, she read the Post daily and offered feedback: “I found myself deeply involved with the struggle to improve the paper. Somewhat to my surprise, given that I thought of myself during this period as unsophisticated, unworldly, and fairly unopinionated. I seem to have been full of independent appraisals of the paper and what it was printing.”

The Washington Post – beginnings:
In June of 1933, Katharine’s father, Eugene Meyer, bought The Washington Post at a bankruptcy auction. The paper had fallen on hard times and was led by an aimless owner. Five years earlier her father had tried to buy it for $5m, at the auction he got it for $825k. 

Eugene soon realized the newspaper business wasn’t like the other businesses he knew. The space was competitive. The tactics he applied weren’t generating results. The beginning was a struggle. But he always maintained his belief that a newspaper is a public trust, meant to serve the public. And over time, he stuck with it and began to create his own success. See his original principles on page 63.

The Washington Post – Phil Graham years:
Phil, Katharine’s husband, joined the Post as associate publisher in January of 1946 at the age of 30. He would learn an entirely new and competitive business, starting at the top as deputy to Eugene. He was relentless and worked incredibly hard as a close collaborator. By 1947, Phil had established himself as the defacto leader of the paper. He was involved in everything. 

By 1948, circulation had increased from 50k to 180k daily. Advertising had gone from 4m lines to 23m. The Post had been awarded numerous prizes. Eugene decided to officially pass the paper on to Phil and Katharine so it would stay in the family.

Over time, all of Phil’s responsibilities and interests built up—he was stretched thin—and that took a toll on his health and endurance. He suffered from various illnesses, often drank too much, and lashed out in explosions of anger at people who provoked him in the slightest. There were shadows building.

Phil eventually suffered from severe manic depression (bipolar disorder). He grew completely dependent on Katharine, almost like a child. The time between his hyperactivity and despair started growing more severe and occurring closer together. Then he ran off and had a public affair and announce his intention to divorce Katharine. 

Phil was hospitalized for his own safety. But negotiated his own release and went with Katharine to their farm in the countryside. After lunch they went upstairs for a nap, Phil excused himself to lie down in a separate bedroom. A few minutes later Katharine heard a gunshot. Phil had killed himself. She found him in the downstairs bathroom. 

Living in Phil’s shadow: 
“Despite my pleasure in the life I was leading during these years, I can see now that I was having problems I didn’t acknowledge to myself. I was growing shyer and less confident as I got older. I still didn’t know how to look my best or handle myself in social situations. I was afraid of being boring, and went on believing that people related to us entirely because of Phil.” 

“At the same time he was building me up, he was tearing me down. As he emerged more on the journalistic and political scenes, I increasingly saw my role as the tail to his kite—and the more I felt overshadowed, the more it became a reality…The wit he had turned on others he now turned on me. I became the butt of the family jokes. Strangely, I was still so mesmerized by him that I didn’t perceive what was happening, and even played along with it.” 

“I felt as though he had created me and that I was totally dependent on him…The truth is that I adored him and saw only the positive side of what he was doing for me. I simply didn’t connect my lack of self-confidence with his behavior toward me.”

When she and Phil were splitting up, Katharine was intent on keeping the paper in her family until one of her children could run it. Her friend, Luvie Pearson, looked at her and said, “Don’t be silly, dear. You can do it….You’ve just been pushed down so far you don’t recognize what you can do.” This was the first time she ever contemplated the idea that she could actually run the Post.

On her father’s death:
“People react in such complicated ways to any death, but particularly to the death of a parent, because a lot of what one feels is about oneself and the sense that nothing now stands between that self and dying. You have now become the older generation.”

The Washington Post - Katharine’s rise:
After Phil’s death: “It’s hard to remake decisions and even harder to rethink non decisions. Sometimes you don’t really decide, you just move forward, and that is what I did—moved forward blindly and mindlessly into a new and unknown life.”

September 20th, 1963, Katharine was elected president of The Washington Post Company at a board of directors meeting. 

“I naively thought the whole business would just go on as it had while I learned by listening. I didn’t realize that nothing stands still—issues arise every day, big and small, and they start coming at you. I didn’t understand the immensity of what lay before me, how frightened I would be by much of it, how tough it was going to be and how many anxious hours and days I would spend for a long, long time. Nor did I realize how much I was eventually going to enjoy it all.” 

Redefining her role: Comparing herself to her exaggerated idea of Phil’s ability and accomplishments only made things more challenging. “I had to come to realize that I could only do the job in whatever way I could do it. I couldn’t try to be someone else, least of all Phil.”

“What I essentially did was to put one foot in front of the other, shut my eyes, and step off the edge.”

Her devotion to the Post and her overwhelming desire to keep the paper in the family, despite her insecurity and lack of knowledge, she knew she had to make it work. She got down to the job and set out to learn everything she could. 

“Most of all, what I know I did well in these years was to care about the company. I took an inordinate interest in all that we did…I tried to create an atmosphere that gave people the freedom to do their jobs, an environment in which good ideas would always be heard. I think I shared the highs and the lows, the failures as well as the successes.” 

The Pentagon Papers:
The New York Times got a hold of classified documents and started running articles about the secret history of decision-making in Vietnam—the Pentagon Papers. More formally titled, “History of the United States Decision-Making Process on Vietnam Policy.” Secret of Defense Robert McNamara had commissioned the review in 1967 before he had left the Pentagon. This resulted in a year-and-a-half-long study, with a 3000 page narrative history, and 4000 page appendix of documents. It was 47 volumes covering American involvement in Indochina from WWII to 1968 when peace talks began on the Vietnam War began in Paris. The government forced the Times to suspend publication. The Post was the only other paper that was able to get its hands on the raw documents—though it was a 4400 page jumbled mess of unordered pages without page numbers. 

Internal team at the Post was conflicted about publishing and defying court orders. But the company’s soul was at stake. The editors were pushing to publish in solidarity with the Times on the issue of freedom of the press. Their lawyers pushed back. Publishing could destroy the paper. But not publishing and advancing their own cause could do the same thing. Katharine made the decision to publish. 

Supreme Court eventually ruled that the government had not met the burden of showing justification for restraining further publication. 

The Post, as a policy, never published information based on intercepted communications, signal intelligence, or cryptography that endangered national security. This was a pledge they kept even with the Pentagon Papers.

“That was a key moment in the life of this paper. It was just sort of the graduation of the Post into the highest ranks. One of our unspoken goals was to get the world to refer to the Post and New York Times in the same breath, which they previously hadn’t done. After the Pentagon Papers, they did.” Ben Bradlee

Watergate is ultimately what led to the Washington Post becoming a household name.

Integrity:
In 1970, the Post hired an ombudsman whose job it was to receive and review complaints about what appears in the paper—only the second paper to do so.

During Watergate created strict rules to ensure fair coverage and accurate details, despite the abuse Katharine and the paper were facing from the Nixon administration. Every bit of information attributed to an unnamed source had to be supported by at least one additional independent source. They ran nothing that was reported by another newspaper, television or radio station without independently verifying and confirming by their own reporters. Every word and every story was read by at least one senior idiot before it went into print. “No matter how careful we were, there was always the nagging possibility that we were wrong, being set up, being misled.” 

Warren Buffett:
Warren joined the board of The Washington Post Company in 1974 and started mentoring Katharine in business education. During meetings he would bring as many annual reports as he could carry and took Katharine through them, describing different businesses, illustrating his points with real-world companies and case studies, identifying the differences between good businesses and bad ones.

Helped her discover self-confidence: “Warren summed up our learning relationship by suggesting that I seemed to go around as though I were seeing myself through the distorting mirrors of a carnival fun house. He saw it as his task to get me a better mirror that could eliminate the distortions.”

“He later told me that he subscribed to Charlie Munger’s ‘orangutan theory’—which essentially contended that, ‘if a smart person goes into a room with an orangutan and explains whatever his or her idea is, the orangutan just sits there eating his banana, and at the end of the conversation, the person explaining comes out smarter.’ Warren claimed to be my orangutan. And in a way he was. I heard myself talk when I was with him and I always got a better idea of what I was saying.” 

The pressmen’s strike:
Early morning on October 1, 1975, the contracts between The Washington Post and its unions had expired at midnight. Around 4am, the pressmen disabled all nine presses, including setting fire to one and beating the press foreman, Jim Hover. The pressmen walked out, taking the other unions with them, and started picketing. When Katharine arrived there was a foot of water covering the floor, smoke, and chaos. 

Katharine never wanted a strike and told the managers to avoid one if possible. And once it began, she didn’t want it last one second longer than necessary. None of their preparations in case a strike had occurred had planned for the presses being so badly damaged—electrical wiring ripped out, essential operating parts removed, oil drained out to strip the gear, and newsprint rolls slashed, or having all the craft unions in the building out on strike together.

Once they fixed one press, a group of advertising executives and others stepped in to run the press. They were able to print 100k papers that same night. Afterwards, the papers made their way through the mailroom where they were bundled up by another crew of executives and sent down the chutes to the waiting trucks. 

Preparing the mailing for the large Sunday papers was time-consuming and dirty. Katharine worked the mailroom on Saturday nights throughout the strike, as well as several other nights during the week. Went on duty when presses started to run at 930pm, didn’t finish until 3 or 4am. Left them filthy, sweaty, and covered with paste. “We had to roll up each individual paper in a brown wrapper, paste on an address label, seal the whole thing shut, and throw the finished, wrapped package into the big, smelly, heavy, and unwieldy canvas bags at the side of the work table, which we then dragged over to another station from which they were finally hauled off to the post office. 

“The whole job was so tedious and interminable that we came to look on it as our supreme service for the cause, the ultimate sacrifice. Warren Buffett, who spent several Saturday nights in the mailroom with us, said it made him rethink the price of the Sunday paper—no price was sufficient.”

For the first ten days of the strike, they operated at a high level of activity and stress. Facing uncertainties, difficulties, and violence at the picket line. Katharine received threats and personal attacks. Nails and tacks were spread across the alley entrance near the office and resulted in flat tires for those coming into the office. Pressmen began picketing the paper’s advertisers and boycotting their goods. They passed out flyers for consumers to boycott the advertisers goods, went into stores and dumped goods off shelves, and in one instance poured oil into a store’s fish tank, killing all the fish. 

“We had weathered a strike we hadn’t asked for and didn’t control. The Post survived this crucial test, but there was no ‘clean victory’—it was a painful one for the Post, for its guild and craft-union members, and for the Washington community. It divided the paper, creating a false atmosphere of ‘us’ versus ‘them.’ Nearly two hundred people lost their jobs.”

“I never wanted the strike. I know that many people believe I deliberately set out to destroy a union, but that was certainly not the case….I never dreamed it was possible to replace the pressmen, not did I feel it was desirable….Most people at the Post are still represented by unions.”

The Washington Post has lived long and honorably with its unions…Katharine believed that they benefited from strong, healthy trade unionism. She always believed that. But she stands by the choice to go around the union because she had no other choice. The future of the company hung in the balance. The strike was a great tragedy that could have been avoided with wiser union leadership. Many good pressmen were caught in the crosshairs, they either had to resign from the union or remain with leaders who led them so poorly and had done tremendous harm. 

“I felt that the philosophy that any union is right no matter what it does was an odd cause for which to sacrifice one’s career. I wish the pressmen had influenced their union leadership to be responsible in the first place. Failing that, I wish they had returned as individuals. Unfortunately, many followed Dugan over the cliff.”

The strike taught Katharine necessary, but painful lessons about the need for strong and compassionate managers who are knowledgeable about the work, labor relations, and communications. The paper became more efficient, flexible and productive as a result. Went from 17 pressmen on each press before the strike to 8 person crews afterwards. Press speeds increased. Atmosphere improved throughout the building. Katharine focused on establishing better communication within the company and it resulted in a stronger paper.

Decoded – Jay-Z

Decoded – by Jay-Z
Date read: 1/25/23. Recommendation: 10/10.

Jay-Z details his own story and deconstructs the lyrics of the most important songs in his career. I couldn’t put this book down—Jay-Z’s rise to become a self-made billionaire is one of the most inspiring stories you will come across. It’s crazy smart and packs a punch. There are great lessons in fundamentals, depth, truth, flow, and motion that are worth reflecting on and instilling in your own life and work.

See my notes below or Amazon for details and reviews.

My Notes:

Origins:
Nine years old, summer of 1978, saw a circle of kids on his way home from playing Little League with his cousin and he moved through the crowd towards the middle, “It felt like gravity pulling me into that swirl of kids, no bullshit, like a planet pulled into orbit by a star…His name was Slate and he was a kid I used to see around the neighborhood, an older kid who barely made an impression. In the circle, though, he was transformed, like the church ladies touched by the spirit, and everyone was mesmerized. He was rhyming, throwing out couplet after couplet like he was in a trance, for a crazy long time—thirty minutes straight off the top of his head, never losing the beat, riding the handclaps…I was dazzled. That’s some cool shit was the first thing I thought. Then: I could do that.” Jay-Z

Natural talent: Started writing rhymes in his spiral notebook that same night. The paper was unlined and he filled every space on every page, writing vertically, horizontally, crowding words together as best he could, scratching out others.

Finding your voice: Jay connected with an older kid and the best rapper in Marcy, Jaz-O. The two would practice their rhymes and record on an old tape recorder with a makeshift microphone attached. “I saw it as an opening, a way to re-create myself and reimagine my world. After I recorded a rhyme, it gave me an unbelievable rush to play it back, to hear that voice.” Jay-Z

Life experiences give you credibility: “I wasn’t even in high school yet and I’d discovered my voice. But I still needed a story to tell.” Jay-Z

Jay wasn’t sure he could get rich from rap, but he knew it would become much bigger than it was before it went away and he leaned into that.

“Manager? That’s a promotion, not a dream.” Jay-Z

Flow:
“From the beginning, it was easy, a constant flow. For days, I filled page after page. Then I’d bang a beat out on the table, my bedroom window, whatever had a flat surface, and practice from the time I woke in the morning until I went to sleep.” Jay-Z

“Everywhere I went I’d write. If I was crossing a street with my friends and a rhyme came to me, I’d break out my binder, spread it on a mailbox or lamppost and write the rhyme before I crossed the street. I didn’t care if my friends left me at the light, I had to get it out.” Jay-Z

“I was good at battling and I practiced it like a sport. I’d spend free time reading the dictionary, building my vocabulary for battles.”

Loved rhyming for the sake of rhyming and the challenge of structuring rhymes in the most effective way possible—moving around couplets and triplets, stacking double entendres, and speed rapping.

Fundamentals:
Jay-Z and his early mentor Jaz-O would go back and forth to each other’s houses and write rhymes for hours. They’d lock themselves in a room with pen and paper. They would test new flows and focus on improving their speed, delivery, and composition.

Putting in the work: “It’s true that I’m able to sometimes come up with songs in a matter of minutes after hearing a track, but that’s a skill that I’ve honed over hundreds of hours of practice and work since I was nine. My earliest mentors in rap taught me that making music is work, whether it was Jaz locking himself in a room working on different flows or Big Daddy Kane taking the time to meticulously put together a stage show. There’s unquestionably magic involved in great music, songwriting, and performances—like those nights when a star athlete is in the zone and can’t miss. But there’s also work. Without the work, the magic won’t come.” Jay-Z

“A tour requires stamina, willpower, and the ability to self-motivate, to hype yourself into game mode night after night….When it comes to signing up new talent, that’s what I’m looking for—not just someone who has skill, but someone built for this life. Someone who has the work ethic, the drive.”

First exposure to the record industry:
When Jay-O got a record deal with EMI in the UK, Jay went along and soaked up all that he could in the recording sessions and meetings.

Producers at EMI convinced Jaz-O to record a pop song with a ukulele on the hook, “Hawaiian Sophie” which tanked. EMI stopped returning his phone calls and instead started courting Jay behind his back. Jay was sick to his stomach and thought the business lacked any sense of honor and integrity. So he buried his rap dreams and went back to hustling.

Hustling:
Got into selling drugs because he was already risking his life by living in the projects, he might as well get paid for it. A friend introduced him to hustling (neither smoked nor used their own supply) and communicated that it required vision and hustle.

“In the mirror, all I saw was a hustler—a hustler who wrote rhymes on corner-store paper bags and memorized them in hotel rooms far away from home—but still, first a hustler. It’s who I’d been since I was sixteen years old on my own in Trenton, New Jersey. I couldn’t even think about wanting to be something else; I wouldn’t let myself visualize another life. But I wrote because I couldn’t stop. It was a release, a mental exercise, a way of keeping sane.” Jay-Z

Find your deep, dark place and create from there:
Jay was interested in the interior of a young kid’s head, his psychology, and bringing that to life through his lyrics. Everything he wrote he wanted to be rooted in the truth of an experience “To tell the story of the kid with the gun without telling the story of why he has it is to tell a kind of lie. To tell the story of the pain without telling the story of the rewards—the money, the girls, the excitement—is a different kind of evasion.” Jay-Z

“I lost people I loved, was betrayed by people I trusted, felt the breeze of bullets flying by my head. I saw crack addiction destroy families—it almost destroyed mine—but I sold it too…But no matter what, it is the place where I learned not just who I was, but who we were, who all of us are.” Jay-Z

Embracing contradiction: “For any image or symbol or creative act to mean something, it has to touch something deeper, connect to something true. I know that the spirit of the struggle and insurgency was woven into the lives of the people I grew up with in Bed-Stuy, even if in sometimes fucked up and corrupted ways….But to have contradictions—especially when you’re fighting for your life—is human, and to wear the Che (Guevara) shirt and the platinum and diamonds together is honest. In the end I wore it because I meant it.” Jay-Z

“The words are witty and blind, abstract and linear, sober and fucked up. And when we decode that torrent of words—by which I mean really listen to them with our minds and hearts open—we can understand their world better. And ours, too. It’s the same world.” Jay-Z

Entrepreneurial mindset:
“You have to make sure the match runs according to your style and rhythm and not get caught up in someone else’s gameplay. You have to be willing to suffer and to make someone else suffer, because only one of you can win.” Jay-Z

A great product and the hustle to move it are the ultimate advantage.

“Success could only mean self-sufficiency, being a boss, not a dependent.”

“I’m also lucky never to have needed the approval of the gatekeepers in the industry because from the start we came into the game as entrepreneurs. That gave me the freedom to just be myself, which is the secret to any long-term success, but that’s hard to see when you’re young and desperate to get put on.” Jay-Z ^ the opposite of this was Jaz-O recording “Hawaiian Sophie” because he trusted producers that got Will Smith airplay even though it didn’t resonate with him.

The depth of hip-hop:
It’s dense with multiple meanings and unresolved layers you might not understand until you’ve listened to it multiple times through. Those layers of meaning help get at complicated truths in a way that straightforward storytelling might not.

“Every hustler knows the value of a feint. It keeps you one step ahead of whoever’s listening in, which is also a great thing about the art of hip-hop. And it makes it all the more gratifying to the listener when they finally catch up.” Jay-Z

Rap is built to handle contradictions: “It doesn’t force you to pretend to be only one thing or another, to be a saint or sinner. It recognizes that you can be true to yourself and still have unexpected dimensions or opposing ideas…The real bullshit is when you act like you don’t have contradictions inside you, that you’re so dull and unimaginative that your mind never changes or wanders into strange, unexpected places.” Jay-Z

The curse of outrage:
“It’s hard to beat the entertainment value of people who deliberately misunderstand the world, people dying to be insulted, running around looking for a bullet to get in front of.” Jay-Z

Life is motion:
“I’ve always believed in motion and action, in following connections wherever they take me, and in not getting entrenched. My life has been more poetry than prose, more about unpredictable leaps and links than simple steady movement, or worse, stagnation. It’s allowed me to stay open to the next thing without feeling held back by a preconceived notion of what I’m supposed to be doing next.” Jay-Z

The truth is always relevant:
“When it seems like I’m bragging or threatening or whatever, what I’m actually trying to do is embody a certain spirit, give voice to a certain emotion. I’m giving the listener a way to articulate that emotion in their own lives, however it applies. Even when I do a song that feels like a complete autobiography, like ‘December 4th,’ I’m still trying to speak to something that everyone can find themselves in.” Jay-Z

“My songs are my stories, but they take on their own life in the minds of people listening. The connection that creates is sometimes overwhelming.” Jay-Z