Entrepreneur

LifePass – Payal Kadakia

LifePass by Payal Kadakia
Date read: 7/15/23. Recommendation: 7/10.

Payal Kadakia’s story makes this book worth picking up. Lots of wisdom around how to navigate your own creative entrepreneurial journey. But as she demonstrates, it starts with revealing more of yourself. Only by putting yourself out there can you open yourself to the right opportunities and self-select out of the wrong ones. The generic self-help exercises at the end of each chapter are forgettable. But it’s easy to look past those.

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

My Notes:

Post-college (Bain):
Took a job at Bain & Company (management consulting) because it looked good on her resume and made her parents proud. For 2.5 years worked 70 hours/week as an associate consultant, then six months before contract renewal was sitting in her manager’s office receiving negative feedback for the first time. She questioned Payal’s reliability and commitment to clients. “If you really want to further your career as a consultant, your clients are going to have to come first. I don’t know if that’s the case for you.”

Her manager was referring to the fact that Payal was studying dance and performing with a troupe, Bollywood Axion, outside of consulting on nights and weekends. Six months before they had a big performance on the same day as an important client meeting and she chose to be at the show. Her manager didn’t make a big deal about it then, but 6 months later it was rearing its head and impacted the way her boss saw her.

Her initial instinct was to dive back into work and prove to her boss that she was worthy of staying on as a consultant. But as she worked harder she realized she would have to give up dance, what she truly loved doing, which wasn’t a compromise she was willing to make. 

“I realized my boss was completely right. I wasn’t fully committed to being a consultant. I wasn’t making Bain my everything, because it simply wasn’t enough for me.”

Warner Music Group:
When her contract was up at Bain, Payal found a job in 2008 working on licensing agreements for digital music at Warner Music Group. It paid less and wasn’t as prestigious, most of the people in her life looked at her like she was crazy. But this was the most comfortable compromise at that time, she wasn’t quitting to dance full time and was giving herself more predictable hours. She had a steady income, work ended at 5 p.m. every day and she could attend dance classes and rehearsals all evening. 

This was a period of transition. Also left Bollywood Axion and started choreographing her own dance pieces (something she found to be a powerful expression of herself). Led her to start her own dance company that showcased Indian dance as an art and culture beyond merely a form of entertainment and fun. Started Sa Dance Company. 

Sa Dance Company:
Applied to participate in an annual Indian dance festival in downtown Manhattan. NYT dance critic, Alastair Macaulay, decided to do a piece on the festival in the next day’s arts section and Sa would be on the Saturday morning cover. Huge half-page image of Sa in motion, dancers looked radiant—a sign she was on the right track. She felt like the universe was telling her to believe in herself and what she was doing.

Spent the next several months planning Sa’s weekend-long Premier NYC Showcase. Dove into making her own production, writing her own story, creating new choreography, and rehearsing for hours with the dancers with the goal of sharing the beauty of Indian dance. To reserve the theater, Payal fronted $20k, her entire savings account. It was on her to sell tickets to break even. Had to sell 1000 tickets to cover her costs. All three shows sold out. 

Sitting in her office at Warner, she realized there was still a disconnect between the person she was at work and the life she wanted for herself. 

San Francisco:
During the Warner and Sa years, she spent all her time working and dancing. But in the summer of 2010, one of her close friends (Parul) invited her to San Francisco for her birthday. This helped create some distance and the change of pace helped her gain new perspective. 

At the birthday gathering, she chatted with Parul’s friends, who all seemed to be developing apps, starting companies, or embarking on some type of entrepreneurial journey. People were pursuing exciting, creative projects as actual career paths. Unlike anyone she knew in New York.

On Sunday night red-eye flight back to New York, her mind was racing. Idea of creating something of her own as her career fascinated her. How could she create something that provide the same type of freedom and inspiration? She gave herself two weeks to come up with an idea for something she would be passionate about creating. 

Back in NYC, as she settled into the week, she opened her laptop and looked for a ballet class to attend. She searched websites for different studios across the city, comparing schedules, researching their instructors, mapping out their locations. Two hours later looked up and had thirty browser tabs opened and realized she wasted her afternoon without finding anything. Entrepreneurial epiphany: why wasn’t there one place you could go to find and book classes?

This was the earliest inkling for ClassPass, an app to give people the opportunity to keep moving and try new things, and as a business, it became a new path for my life that aligned my calling with my career. 

Leaving Warner:
Created business plan and built up courage to leave her job. The day she quit got a message from the vice chairman of Warner asking her to come to his office. He wanted to hear about what she was doing next. He told her he wanted to invest, gave her a check for $10k and introduced her to David Tisch, who was heading up Techstars (one of hottest tech incubators in NYC). 

ClassPass:
Built beautiful product, homepage colors were just right, launched to fanfare and publicity, but then zero bookings came through. Social media, brand partnerships, press hits were not leading indicators of success. The false signals of success shielded them from seeing the real problems right in front of them. Hadn’t fully understood the challenges our customers were facing in getting to class. Reservations were the most important metric. 

1.5 years after visiting SF, went back to try to raise capital, met with big-name VC firms. None of them wanted to give her money. And no one was signing up for classes on their website. Sent email blast to 10k subscribers asking people to sign up for a free class, and not a single person converted. 

Decided to launch something new with a value prop that was more enticing. There wasn’t anything motivating customers to book classes through their site. Passport idea allowing them to bundle together trial classes at different studios to explore new classes over the course of a month. But this was only available to new customers for first month. Sales improved but then people dropped out or used new emails to sign up for another month, upsetting the studios when people returned at discounted prices after their initial trial. 

Eventually pivoted into a subscription service for fitness classes that allowed customers to return to classes they liked and continue exploring month after month.

Years later ClassPass was acquired by Mindbody, thanks to a connection and partnership she cultivated with Rick Stollmeyer (their founder) in the early days.

Quench Your Own Thirst – Jim Koch

Quench Your Own Thirst: Business Lessons Learned Over a Beer or Two by Jim Koch
Date read: 2/18/23. Recommendation: 7/10.

Jim Koch’s inspiring story of founding the Boston Beer Company (Samuel Adams) and lessons learned in building a meaningful business along the way. Koch has great sections on risks, the difference between what’s scary and what’s dangerous, charting your own path, and doing the right thing.

See my notes below or Amazon for details and reviews.

My Notes:

Taking risks:
Spring of 1984 decided he was going to leave his job as a management consultant at Boston Consulting Group (BCG) to start his own beer company (the Boston Beer Company, famous for Samuel Adams). His family had a legacy of brewing beer (five generations on his father’s side were brewmasters). His dad thought he was an idiot, leaving a high-paying job. Jim’s response was that he can make a living, but not the living he was currently making. And that was enough, and he’d be happier running his own small brewery than constantly traveling across the country and working for someone else like he was in his consulting role. 

People were perplexed as to why he was leaving a great consulting job for a new unexpected path as a brewer-entrepreneur. He was supporting his wife and two small children. What if he blew up his life? What if it failed? But it wasn’t as scary as it looked from the outside. 

“Most risks aren’t really risky. Isn’t the biggest risk of all that you’ll waste your life doing what you don’t really enjoy doing, making compromise after compromise?”

“By the time I reached my mid-thirties, starting a company didn’t seem fundamentally different from any other practical task I’d attempted. I wasn’t terrified at the prospect of leaving stability and familiarity behind, because I knew things would work out. Even if the solution to a problem didn’t come to me immediately, I knew that if I hung in there, I would find it. I just needed to be in the right frame of mind to see it.” 

Scary versus dangerous:
“At Outward Bound, we taught people to rappel off a cliff—you literally walk off a cliff backward into empty space. That scares the bejesus out of most people trying it, or even watching it, for the first time. In truth, that rope is strong enough to hold a car. But the first time you do it, it’s pretty scary. It’s just not very risky.”

“Other kinds of situations, however, really are dangerous even if they don’t seem like it. Let’s say it’s a really beautiful early spring day. You’re on the side of a mountain or glacier, walking across a sunlit slope that isn’t too flat or too steep. You think everything is fine, but you’re wrong. The sun is hitting the top layer of snow, causing some of it to melt. The water is trickling down into layers of the snow and ice below. When enough water hits a layer of less-dense snow that had fallen on top of an icy layer months ago, the entire layer begins to slide, and the snow breaks free. All of a sudden, you have an avalanche. Not just an avalanche—AN AVALANCHE! These things can be hideously dangerous. People caught in avalanches tend not to survive. This is real danger, despite the bright sunlight and the sparkling snow.” 

Chart your own path:
When Jim was 24 (1973), he was enrolled in graduate school (a dual J.D./M.B.A. program at Harvard). He felt trapped and decided to drop out. Went to work at Outward Bound, an intensive outdoor program designed to foster mental toughness. Gave him a chance to open his mind and build perspective away from Harvard. Cast aside the weight of people's expectations and came to grips with his true self. 

“It may have seemed like I was a ‘dropout,’ and in a literal sense I was. I was moving in no particular direction, toward no particular goal. To my Harvard classmates, I looked like a loser. But I was also laying the foundation for life as an entrepreneur. I thought of myself as gathering my forces.” 

“When I launched the Boston Beer Company, I knew what I wanted: freedom, personal growth, connectedness with others, and the opportunity to do something that mattered, at least to me. I got all of those benefits long before I realized any financial returns. I have enjoyed the freedom of being my own boss, waking up every morning to decide what I need to do that day, stretching myself to learn new lessons or to find new capabilities.”

Focus on meaningful work:
“If you’re going to work hard, you should find it satisfying and meaningful. Work is too much a part of your life and identity not to.”

Loved the intellectual challenge of consulting, but not the travel and being away from his young family. “I wanted to see more of my family while doing something I enjoyed, something that was meaningful.” 

My idea boiled down to: Make great beer. Give it to people fresh. Find customers.

Ignorance:
“Ignorance can actually be a huge asset, giving you the best vantage point. When I started the Boston Beer Company, I had no serious beer industry experience on my side—only ignorance…” 

Clear goals:
After launching the company, the goal was to get their beer into 100 bars in Boston that they handpicked. They got every single one of them.

Do whatever it takes:
Late summer afternoon in 1985, Jim walked into a Boston bar that he wanted to carry Samuel Adams after the lunch rush. He asked the bartender to see the manager. The bartender said that he wasn’t there during the day, he was only there on Thursday nights. Jim replied he would come back then and asked when a good time would be. The bartender said after 10pm—that was his way of screening out salespeople from a regular beer distributor who wouldn’t ever show up that late after work hours. But Jim did. Because that was his livelihood. 

The right thing is the hard thing:
Beer needs to be fresh to taste its best. After 4-5 months in a can or bottle, the character degrades and it starts to taste stale. But unsold beer sits in distributors warehouses for months. And breweries rarely took beer out of circulation to replace it. In 1988 bottles came with a freshness dating system made up of a series of little notches that corresponded to a secret code and could only be deciphered with a code card. Created an opportunity for the Boston Beer Company (BBC). They decided to print an expiration date in plain English on bottles and cans. And they created an amnesty program for distributors—if they returned expired beer, BBC would reimburse them. Practice of buying back beer was unprecedented. They were destroying about $100k worth of beer (now over $6m). 

Sunk costs and avoiding catastrophic decisions: In 1986, decided it was time to build their own brewery. They didn’t technically need one, they had a contract brewing arrangement that was working well for them. Spent two years designing the new brewery and buying some of the equipment. They raised outside capital ($11m) and estimated the brewery would cost $8m. But the formal bids came back at $15m. Jim was tempted to bet the farm to make it happen, because that’s what entrepreneurs are supposed to do right? A mentor told him “don’t risk what you don’t have to get what you don’t need.” He ended up backing out, selling the equipment they had already purchased at a nearly total loss (roughly $2.5m). 

Put Your Ass Where Your Heart Wants to Be – Steven Pressfield

Put Your Ass Where Your Heart Wants to Be – by Steven Pressfield
Date read: 2/7/23. Recommendation: 8/10.

Similar to The War of Art, Pressfield continues his tried and true method of packing concise inspiration into a quick read. The main message of the book is about shifting your creative center of gravity from the superficial and fearful ego to the deep and fearless self. This requires committing for the long haul. Must read for any entrepreneur or artist trying to create something from nothing.

See my notes below or Amazon for details and reviews.

My Notes:

Show up:
“When I sit down to write in the morning, I literally have no expectations for myself or for the day’s work. My only goal is to put in three or four hours with my fingers punching the keys. I don’t judge myself on quality. I don’t hold myself accountable for quantity. The only questions I ask are, Did I show up? Did I try my best?” SP

“Whatever you can do or dream you can, begin it. Boldness has genius, power and magic in it. Begin it now.” Goethe

“Here’s my frame of mind as I sit down to work: This is the day. There is no other day. This is the day. In other words, I release every thought that smacks of, ‘Maybe we can do this some other time.’ There is no other time.” SP

“Putting our ass where our heart wants to be is the equivalent of Alexander charging into the breach at the Granicus River or at the Issus or Gaugamela. We too are risking it all. We too hold nothing back. We too have hurled ourselves headlong into the unknown.” SP

Location matters:
You must leave the place where you live and move to the hub of the creative world where your dreams are most likely to come true. There’s no substitute for being in the heart of the action. Ernest Hemingway moved to Paris. Bob Dylan moved to Greenwich Village. 

Commitment:
“The positive face of commitment is self-empowerment. The very act of putting our ass where our heart wants to be makes a profound impression, not just on those we wish to work with or be mentored by, but on ourselves.” SP

“In myth and legend, when the hero commits to an intention by taking bold action, he enacts a Cosmic Overthrow. He ‘crosses the threshold.’ Like Luke Skywalker heading with Obi Wan Kenobi for Mos Eisley spaceport or Dorothy being swept away from Kansas by a cyclone, the hero moves from the Ordinary World to the Extraordinary World. She has gone from the Known to the Unknown.” SP

“The universe responds to the hero or heroine who takes action and commits. It responds positively. It comes to the hero’s aid.” SP

Perseverance:
“For writers and artists, the ability to self-reinforce is more important than talent.” SP

“Resistance is always strongest at the finish.” SP

“Killer instinct is not negative when we use it to finish off a book, a screenplay, or any creative project that is fighting us and resisting us to the bitter end. Steel yourself and put that sucker out of its misery.” SP

Visualization:
“What fascinates me about the character of Alexander the Great is that he seemed to see the future with such clarity and such intensity as to make it virtually impossible that it would not come true—and that he would be the one to make it so. That’s you and me at the inception of any creative project. The book / screenplay / nonprofit / start-up already exists in the Other World. Your job and mine is to bring it forth in this one.” SP

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

Empire State of Mind – Zack O'Malley Greenburg

Empire State of Mind – by Zack O'Malley Greenburg
Date read: 1/16/23. Recommendation: 8/10.

An exceptional Jay-Z biography that details his journey as one of the greatest artists and entrepreneurs of our generation. This book aims to answer a simple question: How did Jay-Z rise from a Brooklyn housing project to a position as one of America’s most successful entrepreneurs? It contains great lessons in the power of controlling your own destiny, honing resourcefulness, doing the work, taking risks, and allowing your voice to evolve.

See my notes below or Amazon for details and reviews.

My Notes:

This book aims to answer a simple question: How did Jay-Z rise from a Brooklyn housing project to a position as one of America’s most successful entrepreneurs? 

The benefits of starting late:
“My first album didn’t come out until I was twenty-six, so I had a bit more maturity….My debut album had all these emotions and complexities and layers that a typical hip-hop album wouldn’t have if you were making it at sixteen, seventeen years old. That isn’t enough wealth of experience to share with the world.” Jay-Z

Control your own destiny:
Record companies had a habit of taking advantage of artists financially. Jay-Z was focused on making great music and controlling the business side too.

Built “an unparalleled commercial hip-hop empire encompassing music, film, liquor, and a clothing company that grew from a few sewing machines into a giant that produced $700 million in annual revenues.” ZG

“Jay-Z’s ability to make money by attaching his name to products is one of his greatest strengths as a businessman, and it was especially important during a period of declining numbers in the record industry, when barely one-fifth of his earnings came from record sales.” ZG 

Jaz-O:
Jay-Z’s early mentor helped him fine-tune his rhymes—his lyrics became wittier, his delivery faster, and his syncopation sharper. Jay-Z would practice his rap skills at school by freestyling to beats pounded out on the cafeteria table.

In 1988, Jaz-O became the first rapper to land a deal with the British label EMI. He brought Jay-Z along to London where he got his first exposure to the broader music industry.

In 1989 after returning to the U.S., Jay-Z talked his way onto the tour bus of Big Daddy Kane (a successful rapper). Would go on stage during intermissions to entertain crowds with his freestyle. Spent four months working unpaid for a place to sleep on the tour bus floor and food. 

“After the tour, Jay-Z found himself between worlds. Nearly twenty years old, he’d gotten a taste of the good life with Jaz-O in London, and he’d rubbed elbows with the biggest names in hip-hop on Big Daddy Kane’s tour. But he’d dropped out of high school, and his own musical career hadn’t gotten to a point where he could make serious money as an artist. So he picked up where he left off as a hustler.” ZG

Hustling:
Childhood friend DeHaven Irby introduced Jay to the lucrative opportunities offered by drug dealing. At 18, Jay started taking the train to Trenton on weekends where Irby taught him everything he knew about the local drug market. 

Jay-Z saw music as a side hustle, his first album was supposed to be his only album. But selling drugs was what he saw as the most lucrative path. But in 1994, in an ambush by rivals, Jay-Z was shot at multiple times before a gun jammed, which saved his life. At that point, he got out of the drug trade in the mid-90s. He knew he couldn’t run the streets forever and the only way out was likely death or prison. 

Natural talent:
“What set Jay-Z apart as an artist was the sharpness and rapidity with which he delivered his lyrics; that verbal dexterity earned him some attention in the underground scene.” ZG

Memorization:
Jay-Z is famous for memorizing all his verses instead of writing them down. Early in his career (1992), Clark Kent (A&R department at Atlantic Records) wanted Jay to lay down a song with rapper Sauce Money. Producer, Patrick Lawrence, was in charge of booking studio time for them. After three hours of Jay and Sauce laughing and talking, Lawrence got on them for wasting studio time. Jay asked to hear the song. “Lawrence played the track. Jay-Z began mumbling along to it, then picked up a pen and a notebook and seemed to write several lines. He placed the pad on the sofa and started pacing back and forth, muttering half-formed words. After five minutes, he glanced once more at the pad and told Lawrence he was ready. While Jay-Z was in the sound booth recording his verse, Lawrence went over to see what he’d written in the notebook, still sitting on the couch. ‘I walk to the pad, and there’s fucking nothing on it,’ Lawrence recalls. ‘He was doing it as a fucking joke, like just to show people.’” ZG

Recording Brooklyn’s Finest with Notorious B.I.G.—Big saw Jay do his part without having anything written down. He had to go home to do his part and fill in the blanks and only after he saw Jay do that, he also stopped writing down his rhymes. 

Debut Album:
Thanks to connections, Jay-Z landed tracks from well-respected producers for his debut album, Reasonable Doubt. With his debut album nearly complete, he shopped it to all major record labels but no one was interested. 

Seize creative control: After getting rejected by every major label, Jay-Z and his business partner, Damon Dash, pooled their resources to start their own record label, Roc-A-Fella Records. 

Resourcefulness and doing whatever it takes: They pressed their own records, their CDs, their T-shirts, their stickers, their flyers. Pedaled music from the backs of their cars. Traveled across the five boroughs distributing tracks in clubs, barbershops, and street corners. Went to open mic nights. 

Creating their own brands:
One of Dash and Jay’z primary tenants was that they shouldn’t let other people make money off of them or give free advertising—meaning they should always be compensated for endorsements or create their own brands. 

During the late 90s, Jay and Dash would often wear Iceberg (Italian knitwear designer). His fans started wearing it and Iceberg’s sales took off. They approached the brand about a partnership and were shrugged off. Jay and Dash then went on to start Rocawear. 

Rocawear was started in the back of the Roc-A-Fella Records office with three sewing machines where they stitched a Roc-A-Fella logo on the front of a T-shirt. But they barely knew how to sew and realized they had no idea what they were doing so they started working with Russell Simmons when founded Phat Farm for advice and partners. Within 18 months, Rocawear was doing $80 million in revenue. 

Transcending mentors and business partners:
“Just as he honed his lyrical skills with Jaz-O’s help as a teenager in Brooklyn and developed his hustler’s sense selling crack with DeHaven Irby in Trenton, he learned legitimate entrepreneurialism from Damon Dash. In each case, Jay-Z absorbed the best qualities of his mentor, applied his own considerable talents to the subject at hand, quickly surpassed said mentor, and moved on to the next one.” ZG

Taking over as president at Def Jam:
When he started at Def Jam, he found people who had been living off one act for the past 20 years, there was no excitement, nothing fresh. During a retreat, he went around the room asking employees to share their reasons for getting into the record business to revitalize their sense of meaning and connection to their work. “We got people to go back to that inner kid and the joy of being in the record business.” Jay-Z

The key to staying on top is to treat everything like it’s your first project—stay humble and curious. 

In December of 2007, his three-year contract was nearing an end and he had launched the careers of Rihanna, Kanye West, and Ne-Yo. His musical career was again on the rise and he immersed himself back into that. 

Blazing the trail for hip-hop at rock festivals:
Headlined Glastonbury in UK in 2008. Many, including Noel Gallagher (Oasis), spoke out against a rapper playing a traditionally rock-focused show. Critics thought Jay would be booed off the stage. Jay came out with a parody of the Oasis song “Wonderwall” and the crow erupted. 

Allow your voice to evolve:
“But the most remarkable aspect of 4:44 was its reflection of an artist who’d evolved from a closed-off adolescent to victory-obsessed hot-head to overly stoic dad to middle-aged sage finally in touch with his emotions and vulnerability.” ZG

Let My People Go Surfing – Yvon Chouinard

Let My People Go Surfing: The Education of a Reluctant Businessman – by Yvon Chouinard
Date read: 1/10/23. Recommendation: 10/10.

A wonderful autobiography that details Chouinard’s early days as a climber and the origins of Patagonia. Most of the content in the book was originally intended to act as a philosophical manual for employees of Patagonia. But Chouinard makes this captivating for any reader through stories that explore his own life lessons, the trials of building an enduring company, and the trap of short-sighted decisions. The book contains powerful insights on simplicity, disrupting yourself, communicating with customers, seeking inspiration from unlikely sources, and the lifelong search for your guiding principle.

See my notes below or Amazon for details and reviews.

My Notes:

Chouinard Equipment:
Origins: “In 1957 I went to a junkyard and bought a used coal-fired forge, a 138-pound anvil, and some tongs and hammers and started teaching myself blacksmithing. I wanted to make my own climbing hardware, since we were starting to climb the big walls in Yosemite on multiday ascents that required hundreds of piton placements.” 

At the time all climbing gear was European and the pitons used were soft iron—meant to be hammered in once and left in position (and if you tried to take these pitons out and reuse them, they would often break). The prevailing European attitude was to conquer the mountain and leave all gear in place to make it easier for the next person to reach the summit. American climbers modeled themselves after transcendental writers like Emerson, Thoreau, and Muir, and believed in leaving no trace. 

Chouinard made his first pitons from an old chrome-molybdenum steel blade. They were stiffer and stronger, which made them easier to drive into cracks in Yosemite, and they could be taken out and reused. 

“I made these Lost Arrow pitons for myself and the few friends I climbed with; then friends of friends wanted some. I could forge only two of my chrome-molybdenum steel pitons in an hour, and I started selling them for $1.50 each. You could buy European pitons for twenty cents, but you had to have my new gear if you wanted to do the state-of-the-art climbs that we were doing.” 

In 1964, Chouinard put out his first catalog—“a one-page mimeographed list of items and prices, with a blunt disclaimer on the bottom saying not to expect fast delivery during the months of May to November.” 

As demand grew, “We redesigned and improved just about every climbing tool, making each one stronger, lighter, simpler, and more functional.” 

Quality as a top priority: With climbing tools, it is a matter of life and death, and they were often the heaviest users of their own products. 

Despite the volume of sales doubling year over year, Chouinard Equipment showed only about a 1 percent profit at the end of the year because they were constantly coming up with new designs. By 1970 they were the largest supplier of climbing hardware in the U.S. 

Simplicity:
“In anything at all, perfection is finally attained not when there is no longer anything to add, but when there is no longer anything to take away…” Antoine de Saint-Exupéry

“Good design is as little design as possible.” Dieter Rams

“An illustrator becomes an artist when he or she can convey the same emotion with fewer brushstrokes.”

“I believe the way toward mastery of any endeavor is to work toward simplicity; replace complex technology with knowledge. The more you know, the less you need.”

Disrupt yourself:
By the 1970s, the popularity of climbing had skyrocketed. Particularly on well-known routes in primary climbing areas like El Dorado Canyon near Boulder, the Shawangunks in New York, and Yosemite Valley. On these routes, the repeating hammering of hard steel pitons during placement and removal in the same cracks was beginning to severely disfigure the rock. “After an ascent of the Nose route on El Capitan, which had been pristine a few summers earlier, I came home disgusted with the degradation I had seen. Frost and I decided we would phase out of the piton business. This was the first big environmental step we were to take over the year. Pitons were the mainstay of our business, but we were destroying the very rocks we loved.”

Chouinard started looking into aluminum chocks that could be wedged by hand rather than hammered in and out, designed his own versions called Stoppers and Hexentrics, and piloted them in small quantities until they appeared in the Chouinard Equipment catalog in 1972. “The catalog opened with ‘A word…,’ an editorial from the owners on the environmental hazards of pitons and a fourteen-page essay on clean climbing and how to use chocks by Sierra climber Doug Robinson. 

“Within a few months of the catalog’s mailing, the piton business had atrophied; chocks sold faster than they could be made. In the tin buildings of Chouinard Equipment, the steady pounding rhythm of the drop hammer gave way to the high-pitched, searing whine of the multiple drill jig.” 

Underwear: Wearing quick-drying insulation layers (e.g. pile jackets) over cotton underwear defeated the purpose of outer shells. In 1980 they tested making underwear out of polypropylene, a synthetic fiber that absorbs no water. It was originally intended to manufacture industrial commodities like marine ropes which float. Then it started being used in the lining of disposable diapers for its wicking ability to keep babies dry by carrying moisture away from the skin and transferring it to more absorbent outer layers in the diaper. “Using the capabilities of this new underwear as the basis of a system, we became the first company to reach the outdoor community, through essays in our catalog, the concept of layering. This approach involves wearing an inner layer against the skin for moisture transport, a middle layer of pile for insulation, and then an outer shell layer for wind and moisture protection.” 

But polypropylene had a very low melting temperature. Customers who went to commercial laundromats (much hotter dryers than home) would melt their underwear. When Chouinard was at 1984 sporting goods show in Chicago watching a demonstration of polyester football jerseys being cleaned of grass stains. He realized that the material in combination with the etched jersey worked to wick away moisture. Polyester also had a much higher melting temperature. They then introduced their Capilene polyester underwear. Sales soared.

Know your shit: “Some people think we’re a successful company because we’re willing to take risks, but I’d say that’s only partly true. What they don’t realize is that we do our homework. A few years back when we switched midstream from polypropylene to Capilene for our underwear fabric, we had done our fabric development, we had done our testing in the fabric lab. We made tops and bottoms with half the garment Capilene and half polypropylene and extensively tested them in the field. We knew the market, and we were absolutely confident that it was the right thing to do.” 

Other companies started introducing rip-offs and had to scramble to keep up. They repeated the same move in the early 1980s when they realized how bland all outdoor products were (tan, forest green, gray). So they drenched the Patagonia line in color (cobalt, teal, French red, mango, sea foam)

By disrupting themselves, they set the tone for the entire market. Whereas if they had focused on competitors instead, they would have been locked in a reactive state rather than forging ahead with bold decisions and new ideas. 

Switching to organic cotton: “After several trips to the San Joaquin Valley, where we could smell the selenium ponds and see the lunar landscape of cotton fields, we asked a critical question: How could we continue to make products that laid waste to the earth in this way? In the fall of 1994, we made the decision to take our cotton sportswear 100 percent organic by 1996. We had eighteen months to make the switch for sixty-six products, and less than a year to line up the fabric.” 

Seek inspiration from unlikely places:
Chouinard’s first idea for clothing: “In the late sixties, after crag climbing in the Peak District in England, I stopped by an old Lancashire mill that contained the last machine left in the world that still made a tough, superheavy corduroy cloth…Back then, before denim, workmen’s pants used to be made of corduroy because its tufted wales protected the woven backing from abrasion and cuts. I thought this durable cloth would be great for climbing. Ordering up some fabric, I had some knickers and double-seated shorts made. They sold well to our climbing friends, so I ordered some more.”

Rugby shirts: In the late sixties, men didn’t wear bright clothes. Active sportswear was often a gray sweatshirt and pants. On a winter climbing trip to Scotland in 1970, Chouinard bought a regulation rugby shirt to wear, thinking it would be good for climbing since it was built to withstand scrums in rugby and had a collar to keep hardware slings from cutting into his neck. The basic color was blue with two red and one yellow center stripe across the chest. When he returned home his friends started asking about it so he ordered some from Umbro and sold out immediately. They couldn’t keep them in stock. 

Pile sweaters becoming an outdoor staple: “At a time when the entire mountaineering community relied on the traditional, moisture-absorbing layers of cotton, wool, and down, we looked elsewhere for inspiration—and protection. We decided that a staple of North Atlantic fisherman, the synthetic pile sweater, would make an ideal mountain sweater because it insulated well without absorbing moisture…We sewed a few seaters and field-tested them in alpine conditions. The polyester fabric was astonishingly warm, particularly when used with a shell. It insulated well but also dried in minutes, and it reduced the number of layers a climber had to wear.” 

Entrepreneurship:
“If you want to understand the entrepreneur, study the juvenile delinquent. The delinquent is saying with his actions, ‘This sucks. I’m going to do my own thing.’”

“A master in the art of living draws no sharp distinction between his work and his play; his labor and his leisure; his mind and his body; his education and his recreation. He hardly knows which is which. He simply pursues his vision of excellence through whatever he is doing, and leaves others to determine whether he is working or playing. To himself, he always appears to be doing both.” L.P. Jacks

Generalist:
“I’ve always thought of myself as an 80 percenter. I like to throw myself passionately into a sport or activity until I reach about an 80 percent proficiency level. To go beyond that requires an obsession and degree of specialization that doesn’t appeal to me. Once I reach that 80 percent level I like to go off and do something totally different; that probably explains the diversity of the Patagonia product line—and why our versatile, multifaceted clothes are the most successful.” 

Search for guiding principle:
During a period of extreme growth when scale was shaking the company, Chouinard sought advice from Dr. Michael Kami who had run strategic planning for IBM and had turned Harley-Davidson around. 

“Before he could help us, he said, he wanted to know why we were in business. I told him the history of the company and how I considered myself a craftsman who had just happened to grow a successful business…We told him about our tithing program, how we had given away a million dollars just in the past year to more than two hundred organizations, and that our bottom-line reason for staying in business was to make money we could give away. Dr. Kami thought for a while and then said, ‘I think that’s bullshit. If you’re really serious about giving money away, you’d sell the company for a hundred million or so, keep a couple million for yourselves, and put the rest in a foundation. That way you could invest the principal and give away six or eight million dollars every year…So maybe you’re kidding yourself about why you’re in business.’” 

Stick with what you know: “The sooner a company tries to be what it is not, the sooner it tries to ‘have it all,’ and the sooner it will die.” 

As a recession hit the company had to reset, they were growing at an unsustainable pace. They redefined their values and mission statement. And while managers solved for the sales and cash-flow issues, Chouinard led weeklong employee seminars on the company’s revitalized philosophy. The goal was to teach every employee their business and environmental ethics and values. 

Teaching the classes to his employees on Patagonia’s philosophies finally gave Chouinard his answer to Dr. Kami’s question. “I knew, after thirty-five years, why I was in business. True, I wanted to give money to environmental causes. But even more, I wanted to create in Patagonia a model other businesses could look to in their own searches for environmental stewardship and sustainability, just as our pitons and ice axes were models for other equipment manufacturers…I realized how much Patagonia as a business was driven by its high-quality standards and classic design principles. The products we made, each feature of every shirt, jacket, or pair of pants, had to be necessary.” 

“The history of Patagonia from the crisis of 1991-92 to the present day doesn’t make for such interesting reading, fortunately…The story is really about how we are trying to live up to our mission statement: ‘Make the best product, cause no unnecessary harm, and use business to inspire and implement solutions to the environmental crisis.’”

“We never wanted to be a big company. We want to be the best company, and it’s easier to try to be the best small company than the best big company.”

Make the best product:
“Having high-quality, useful products anchors our business in the real world and allows us to expand our mission. Because we have a history of making the best climbing tools in the world, tools that your life is dependent on, we are not satisfied making second-best clothing.” 

Product design principles: Functional, multifunctional, durable, repairable, simple. “As individual consumers, the single best thing we can do for the planet is to keep our stuff in use longer.” 

Non-obvious application of Occam’s Razor and simplification to establish fewer points of failure: “The best-performing firms make a narrow range of products very well. The best firms’ products also use up to 50 percent fewer parts than those made by their less successful rivals. Fewer parts means a faster, simpler (and usually cheaper) manufacturing process. Fewer parts means less to go wrong: quality comes built in.”

“When I’m working on a problem, I never think about beauty. I think only how to solve the problem. But when I have finished, if the solution is not beautiful, I know it is wrong.” Richard Buckminster Fuller

Communicating with customers:
“Since the publication of the 1972 Chouinard Equipment catalog that contained the ‘Clean Climbing’ essay, we have seen that the primary purpose of our catalogs is to serve as a vehicle to communicate with our customers—whether it is by trying to change climbing philosophy, by rallying them to register and vote for the environment…or just by relating stories.” 

The ‘Clean Climbing’ essay not only encouraged climbers to climb clean but was also the first piece ever written about how to use the new chocks. “As a result, Chouinard Equipment’s piton business dried up, and its chock business exploded, nearly overnight. To show its impact, far beyond a business tool, that catalog was reviewed as a mountaineering book in the American Alpine Journal.

“Just as Patagonia makes products for a deeper, less distracted experience of the world and its wild places, our image has to convey refuge from, and offer an alternative to, a virtual world of fast-moving, mind-skimming (and numbing) pictures and sound.” 

Shoe Dog – Phil Knight

Shoe Dog – by Phil Knight
Date read: 6/23/22. Recommendation: 8/10.

A memoir by Phil Knight, the creator of Nike, detailing the wonderful story of the perseverance required over the course of decades to build an enduring company. The most interesting aspect of the Nike story is how the same six people (including Knight) built and continually reimagined the company as they adapted to insane obstacles to defy the odds.

See my notes below or Amazon for details and reviews.

My Notes:

“Now, here, you see, it takes all the running you can do, to keep in the same place. If you want to get somewhere else, you must run at least twice as fast as that.” Lewis Carroll

Resourcefulness:
In 1964, Knight sold out of his first shipment of Tigers (shoe brand from Japan). Needed to get to California to hire a salesman but couldn’t afford to fly and didn’t have the time to drive. So Knight put on his army uniform from being in the reserves, drove to the local air base, and the MPs would wave him onto the next transport to SF or LA, no questions asked. 

“Happiness can be dangerous. It dulls the senses.” PK

The art of forgetting:
“The art of competing, I’d learned from track, was the art of forgetting, and I now reminded myself of that fact. You must forget your limits. You must forget your doubts, your pain, your past. You must forget that internal voice screaming, begging, ‘Not one more step!’” PK

Athletes:
“Bowerman was forever griping that people make the mistake of thinking only elite Olympians are athletes. But everyone’s an athlete, he said. If you have a body, you’re an athlete.” PK

Nike team (1976):
Us against the world: “Undoubtedly we looked, to any casual observer, like a sorry, motley crew, hopelessly mismatched…Each of us had been misunderstood, misjudged, dismissed. Shunned by bosses, spurned by luck, rejected by society, shortchanged by fate when looks and other natural graces were handed out. We’d each been forged by early failure. We’d each given ourselves to some quest, some attempt at validation or meaning, and fallen short. Hayes couldn’t become a partner because he was too fat. Johnson couldn’t cope in the so-called normal world of nine-to-five. Strasser was an insurance lawyer who hated insurance—and lawyers. Woodell lost all of his youthful dreams in one fluke accident. I got cut from the baseball team and I got my heart broken.” PK