LifePass – Payal Kadakia

LifePass by Payal Kadakia
Date read: 7/15/23. Recommendation: 9/10.

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.

How I Built This – Guy Raz

How I Built This by Guy Raz
Date read: 3/1/23. Recommendation: 7/10.

Based on Guy Raz’s podcast of the same name, this book shares insights from some of the world’s top entrepreneurs on building, launching, and scaling their ideas. Great chapters on identifying risk, extending your runway, harnessing the power of your story, and being deliberate about your location.

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

My Notes:

Scary versus dangerous:
“One of the things we taught people to do was rappel off a cliff. It is a very scary thing to do, but you are also held by a belay rope, and that rope would hold a car. So walking off the cliff backwards is scary, but it’s not dangerous. Walking across a thirty-five-degree-angle snowfield on a beautiful late May afternoon with bright blue sky, on the other hand, is not scary at all, but it is very dangerous, because the snow is melting, eventually it is going to find a layer of ice, the water will lubricate that ice, and then you have an avalanche. That is dangerous but not scary.” Jim Koch

“In my situation, staying at BCG that was dangerous but not scary. The danger was continuing to do something that didn’t make me happy and getting to sixty-five years old looking back and going, ‘Oh my God, I wasted my life.’” Jim Koch

“Failing is scary. Wasting your life is dangerous.” Guy Raz

Michael Dell on the origins of Dell Computer Corporation: There was nothing dangerous about his idea, he loved working on computers. He knew them inside and out. The reality was the scariest thing about starting the business—the unknown. “The danger for Michael was in relenting to his parents’ demands that he become a doctor, in hating every waking second of it while he watched the personal computing revolution unfold in front of him, and then in resenting his family for the rest of his life because they pushed him down a path that he knew in his heart was wrong for him.” Guy Raz

Safety nets:
Herb Kelleher, co-founder of Southwest Airlines, didn’t give up his law practice until 1981—fourteen years after founding Southwest. Draymond John continued to work at Red Lobster for six years after he started FUBU, only after he secured a multi-million dollar round of financing. Both used their jobs to create runway for their ideas. 

Avoid catastrophe: “By doing things smartly and safely like this, you’ll give yourself more time and more room to operate, while simultaneously reducing the chances that failure can ruin your life.” 

Never be unprepared:
Each founder that Raz highlights in his book has one thing in common: they’ve done their homework. They know their product, business, customers, and industry inside and out. And this gives them a deep confidence in the viability of their ideas. 

“They knew their ideas would work because they knew their stuff.”

The role of research for artists and entrepreneurs is the equivalent of practice for athletes or rehearsal for actors. “It’s deep work and repetition that sear the fundamentals into your muscle memory….so when the lights come on and it’s time to do something for real, you can put all that prep work away and just act or play or build. You can create freely, without reservation or hesitation.” Guy Raz

Relationships:
“My best business decisions really have to do with picking people. Deciding to go into partnership with Paul Allen is probably at the top of the list…Having somebody who you totally trust, who’s totally committed, who shares your vision and yet has a little bit different set of skills, and also acts as a check on you—and just the benefit of sparking off of somebody who’s got that kind of brilliance—it’s not only made it fun, but it’s really led to a lot of success.” Bill Gates

Know your story:
“The story must explain at a fundamental level why you exist.” Ben Horowitz

“The basic story that answers the big ‘why’ questions is the one that creates loyal customers, finds the best investors, build an employee culture that keeps them committed to the venture, and keeps you committed and grinding away when things get real hard and you want to give up (and you will).” Guy Raz

Location matters:
Three different approaches to location: moving in order to break into your industry, moving in order to break out of your industry, or staying put right where you are. What matters is that you’re intentional in that decision. 

Master your craft:
“Whatever you do, do it well. Do it so well that when people see you do it, they will want to come back and see you do it again, and they will want to bring others and show them how well you do what you do.” Walt Disney

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). 

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

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.” 

The Responsible Company – Yvon Chouinard and Vincent Stanley

The Responsible Company: What We’ve Learned from Patagonia’s First 40 Years – by Yvon Chouinard and Vincent Stanley
Date read: 1/4/23. Recommendation: 8/10.

A quick read that operates like a handbook for how to build an enduring, responsible company. Chouinard and Stanley detail—across decades of experience—how doing the right thing and focusing on sustainable growth is actually what’s good for business. Every entrepreneur should read this. There are tremendous lessons in doing hard things, anchoring in truth, disrupting yourself, and investing in meaningful work.

See my notes below or Amazon for details and reviews.

My Notes:

Patagonia origins:
“Yvon created Patagonia as an offshoot of the Chouinard Equipment Company, which made excellent mountain-climbing gear recognized as the best in the world, but very little money. Patagonia was intended to be a clean and easy company.” 

“At Chouinard Equipment we were used to a life-or-death standard of product quality: you did not sell an ice axe without checking it closely for a hairline fracture or any other fault. Although we applied the same standard to rugby shirts (they had to be thick and tough to survive the skin-shredding sport of rock climbing), we knew that seam failure was unlikely to kill anyone. Patagonia was to be our irresponsible company, bringing in easy money, a softer life, and enough profits to keep Chouinard Equipment in the black.”

We are part of nature:
“As men and women we are part of nature. If we were to have no experience of wild nature, or no way to know of it, we would lose entirely our sense of human scale. We derive our sense of awe from our ability to feel nature’s force. We better know ourselves when we come face to face with the magnificence of the unknown. Emerson, Thoreau, and other transcendentalists learned and taught these lessons in New England in the 1830s through 1860s. They showed us that we can learn directly from nature about who we are and how to live.”

Not everything can be quantified: “We don’t think a speech from John Muir on the need for ecosystem services would have swayed Teddy Roosevelt to preserve Yosemite Park nearly as much as a night in the redwoods under the stars.”

Reducing environmental harm:
“Know your impacts, favor improvement, share what you learn.” Daniel Goleman

“Responsible behavior, as it becomes cumulative, also makes a company smarter, more nimble, and potentially more successful.”

Making it everyone’s job: “It is important to note that Patagonia’s dedicated environmental staff for products numbered all of two. The small size of the department was deliberate: we wanted the reduction of environmental harm to be part of everyone’s job. We did not want to create a separate bureaucracy that might clash unproductively with our product-quality or sourcing staff, or give that staff a reason to make environmental considerations secondary because someone else would handle them in their stead.”

Verify before trust: “Before placing an initial order with a factory, Patagonia has a member of its social/environmental responsibility team visit to verify conditions. This team member can break the deal. Our quality director has similar veto power over the sourcing department’s decision to take on a new factory.”

Win/win: “Companies that recognize the opportunity to use the intelligence and creative capacity of their people to do less harm, certainly less harm that serves no useful purpose, will benefit. The company that wreaks less environmental harm will at the same time reduce its sharply rising costs for energy, water, and waste disposal.”

Meaningful work:
“At its heart, to have meaningful work is to do something you love to do and are good at doing for a living. Most people don’t know, at first, what they love best. What they become best at develops by trial and error or by accident. We’re all good at something: with words or numbers, or we work with our hands, or we work best outside.”

“Meaningful work is doing things you love to do, often, though not always, with other people. No responsible company can function well without a lot of different people doing things they love to do in concert with others. Doing what you love to do makes work meaningful. Doing the right thing, with others, makes work meaningful.”

“We have made the choice to do better and not accept the status quo. This is how our work has become more meaningful: we’re not just making clothes, we’re making long-lasting clothes that do less damage.”

Disrupting yourself:
“In 1972, Chouinard Equipment was still a small company (about $400,000 a year in sales), but it had become the largest supplier of climbing hardware in the U.S. With the increased popularity of climbing, and its concentration on the same well-tried routes (in Yosemite Valley, El Dorado Canyon, the Shawangunks, etc.), our reusable hard-steel pitons had become environmental villains. The same fragile cracks had to endure repeated hammering of pitons during both placement and removal, and the disfiguring was severe. After an ascent of the degraded Nose route on El Capitan, which had been pristine a few summers earlier, Yvon and partner Tom Frost decided to phase out of the piton business. It was a huge risk: pitons were the mainstay of the business. But the change had to be made for reasons both moral and practical: the routes were beautiful and satisfying and shouldn’t be ruined; and to ruin them would put an end to, or greatly reduce, the possibilities for climbing in the most popular areas, and thus eventually hurt our business.”

“There was an alternative: aluminum chocks that could be wedged in and removed by hand without the use of a hammer. Hexentrics and stoppers made their first appearance in the Chouinard Equipment catalog in 1972.”

“That catalog opened with an editorial from the owners on the environmental hazards of pitons. A fourteen-page essay by Sierra climber Doug Robinson on how to use chocks began with a powerful paragraph: ‘There is a word for it, and the word is clean. Climbing with only nuts and runners for protection is clean climbing. Clean because the rock is left unaltered by the passing climber. Clean because nothing is hammered into the rock and then hammered back out, leaving the rock scarred and the next climber’s experience less natural. Clean because the climber’s protection leaves little trace of his ascension. Clean is climbing the rock without changing it; a step closer to organic climbing for the natural man.’”

“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 sheds of Chouinard Equipment, the steady pounding rhythm of the drop hammer gave way to the high-pitched whine of the multiple-drill jig.”

“At Chouinard Equipment, we learned that we could inspire our customers to do less harm simply by making them aware of the problem and offering a solution. We also learned that by addressing the problem we had forced ourselves to make a better product: chocks were lighter than pitons and as or more secure. We might not have risked the obsolescence of our piton business just to sell something new. But doing the right thing motivated us—and turned out to be good business.”

Retention:
“It costs Patagonia roughly $50,000, on average, to recruit, train, and get up to speed a new employee; if we want to make any money, it’s a good idea to keep the ones we have happy and fully engaged.”

“How to gain a customer and keep one? First, make something or offer a service someone can use, for which satisfaction endures. Second, your company should romance, but not bullshit, the people whose business it solicits.”

Navigating downturns:
“Our emergency plan for a downturn of any magnitude now is to cut the fat, freeze hiring, reduce travel, and trim every type of expense except salaries and wages.”

Anchor in truth:
“A company needs to present itself well to the customer; it may even preen a little, the way a lover might take care to dress for a date. A life story, or product story, told just this side of myth-making is okay when it fairly represents the real. But beware of conjuring a false image of your company’s goods or services. Mystification will no longer work in a world where stage fog can be quickly dispersed by a competitor, activist, or regulator.”

“Transparency is the primary contemporary virtue for all responsible businesses.”

“For a company to set goals or assess progress toward meeting them it needs freely flowing, transparent information. No transparency: no accountability.”

Do the hard thing:
“Patagonia was not always an especially transparent company, nor were we eager to learn about problems that seemed beyond our control. We collectively groaned when we learned how harmful conventionally grown cotton was. We had no idea when we decided to switch to organic cotton how much work would be involved; we knew only that it was possible, and that we had no compelling reason to continue to use harmful, chemically dependent cotton.”

“Over time, your company will become healthier as a benefit of knowing your business more intimately—and more fully engaging your workforce and community.”

Build – Tony Fadell

Build - by Tony Fadell
Date read: 7/23/22. Recommendation: 8/10.

Such a great book for entrepreneurs and creators. Fadell, the engineer behind the iPod and iPhone, and founder of Nest, reflects on lessons learned over the course of his career. He offers advice on evaluating opportunities, working with executives, disrupting yourself, managing crises, and knowing when to quit and when to stick it out. Throughout the entire book he ties these themes back into his own experiences and advocates for the importance of having skin in the game.

See my notes below or Amazon for details and reviews.

My Notes:

Evaluating opportunities:
“When you’re looking at the array of potential careers before you, the correct place to start is: ‘What do I want to learn?’
Not ‘How much money do I want to make?’
Not ‘What title do I want to have?’
Not ‘What company has enough name recognition…’” TF

“The only failure in your twenties is inaction. The rest is trial and error.” Anonymous 

Tony spent the dot-com bubble building handheld devices. Instead of going to some internet startup, he went to Philips to make devices, then started his own company to make digital music players. Eventually, that led him to Apple where he made the iPod and iPhone. Wouldn’t have had that opportunity if he didn’t stick with what he wanted to learn and what he cared about building. 

“The way I’ve gotten wealthy is not by accepting giant paychecks or titles to do the jobs I know I’ll hate. I follow my curiosity and my passion. Always.” TF

“What you do matters. Where you work matters. Most importantly, who you work with and learn from matters. Too many people see work as a means to an end, as a way to make enough money to stop working. But getting a job is your opportunity to make a dent in the world. To put your focus and energy and your precious, precious time toward something meaningful.” TF

“Students seek out the best professors on the best projects when getting their master’s or PhD, but when they look for jobs, they focus on money, perks, and titles. However, the only thing that can make a job truly amazing or a complete waste of time is the people.” TF

Characteristics of a successful company:

1. Creating product or service that’s wholly new or combines existing tech in a novel way that competition can’t understand.

2. Product solves a problem—a real pain point that customers experience daily. Large existing market.

3. The technology can deliver on the company vision (product, infrastructure, platform, systems).

4. Leadership isn’t dogmatic about what the solution looks like and is willing to adapt to customer needs.

5. Thinks about a problem or customer need in a way you’ve never heard before but makes perfect sense once you hear it.

Growth:
Company and personal growth: “Either you’re growing or you’re done. There is no stasis.” TF

Grind:
“But if you want to prove yourself, to learn as much as you can and do as much as you can, you need to put in the time. Stay late. Come in early. Work over the weekend and holidays sometimes. Don’t expect vacation every couple of months…” TF

Skin in the game (avoid consulting):
“Just whatever you do, don’t become a ‘management consultant’ at a behemoth like McKinsey or Bain or one of the other eight consultancies that dominate the industry. They all have thousands upon thousands of employees and work almost exclusively with Fortune 5000 companies. These corporations, typically led by tentative, risk-averse CEOs, call in the management consultants to do a massive audit, find the flaws, and present leadership with a new plan that will magically ‘fix’ everything.” TF

“To do great things, to really learn, you can’t shout suggestions from the rooftop then move on while someone else does the work. You have to get your hands dirty. You have to care about every step, lovingly craft every detail. You have to be there when it falls apart so you can put it back together.” TF

Working with executives with strong opinions:
Ask why: “It is the responsibility of a passionate person—especially a leader—to describe their decision and make sure you can see it through their eyes. If they can tell you why they’re so passionate about something, then you can piece together their thought process and either jump on board or point out potential issues.” TF

When to quit and when to stick it out:
“Most people know in their gut when they should quit and then spend months—or years—talking themselves out of it.” TF

Indicators that it’s time to quit: 1) You’re no longer passionate about the mission. If you’re staying for the paycheck or to get the title you want, but every hour feels like an eternity. 2) You’ve tried everything. You’re still passionate about the mission but the company is letting you down.

“Every meeting, every pointless project, every hour stretches on and on. You don’t respect your manager, you roll your eyes at the mission…It is time and energy and health and joy that disappear from your life forever.” TF

“People won’t remember how you started. They’ll remember how you left.” TF

“Quitting anytime things get tough not only doesn’t look great on your resume, but it also kills any chance you have of making something you’re proud of. Good things take time. Big things take longer.” TF

“Too many people jump ship the second they need to dig in and really push through the hard, grinding work of making something real.” TF

Disrupt yourself:
“If you’re experiencing your biggest market share ever, that means you’re on the brink of becoming calcified and stagnant. It’s time to dig deep and kick your own ass.” TF

“We had to make the iPhone, even though we knew it could, probably would, kill the iPod.” TF

Tesla could have fallen into the same trap—made EV cars attractive. Every other carmaker followed. So they focused on innovating charging networks, retail, service, batteries, supply chains to stay ahead.

Three generations of products to get it right:
Make the product (not remotely profitable. Fix the product (get gross margins right). Build the business (reach net profits). 

Managing crises:

1. Keep your focus on how to fix the problem, not who to blame.

2. Don’t be worried about micromanagement. Get in the weeds. During a crisis, your job is to tell people what to do and how to do it.

3. Get advice. Don’t try to solve problems alone.

4. Your job once the initial shock is over is to overcommunicate and listen.

5. Accept responsibility for how it has affected customers and apologize, regardless of whose fault it was.

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

Radical Focus – Christina Wodtke

Radical Focus – Christina Wodtke
Recommendation: 8/10. Date read: 7/14/21.

The best book that I’ve read on using objectives and key results (OKRs) to achieve your most important goals and focus on what matters. Wodtke advertises this as “a business book in the form of a fable” and its format doesn’t disappoint. Radical Focus follows a fictional case study of two entrepreneurs struggling to keep their startup alive. Throughout the story they find themselves struggling to communicate, not allowing their strategy to evolve, and trying to do too many things at once. The story brings the ideas to life without being overly prescriptive. The second half of the book then provides a tactical guide to implementing OKRs in an effort to help both you and your team realize your most ambitious goals.

See my notes below or Amazon for details and reviews.

My Notes:

Focus:
“A startup’s enemy is time, and the enemy of timely execution is distraction.” CW

“Select only one OKR for the company unless you have multiple business lines. It’s about focus.” CW

Weekly check-ins:

1. Objectives = inspiration for quarter. Key results = what happen if you do the right thing. DO NOT pick more than three key results. Set these with 50% confidence of achieving and every week give them a score out of 10 to assess confidence level. When you kick off the quarter, your confidence would be 5/10. As a starting place, think about usage, revenue, and satisfaction metrics as your KRs.

2. Health metrics: Sit below objective and key results. These are things you don’t want to forget or sacrifice while you aim to achieve key results. This could be customer satisfaction (don’t want to alienate current customers), team health, code health, etc.

3. This week: P1s and P2s, write 3-5 big things you’ll focus on this week to affect the OKRs. Don’t list everything you’re going to work on, just the things that must happen or else your objectives will be at risk.

4. Next 4 weeks, pipeline: Things you expect to happen in the next month so stakeholders aren’t caught off guard.

Example of how this might look:

• Objective: Establish clear value to restaurant suppliers as a quality tea provider
  

• KR: Reorders at 85% (5/10)

• KR: 20% or reorders self-serve (5/10)

• KR: Revenue of $250k (5/10)
  

• P1: Close deal with TLM Foods

• P1: New order flow spec’d 

• P1: Three solid sales candidates in for interview

• P2: Create customer service job description

Weekly status emails:

1. Lead with your team’s OKRs, and how much confidence you have that you are going to hit them this quarter.
   -OKRs remind everyone why you are doing the things you do
   -Confidence is a guess of how likely you feel you will meet your key results. 1 is never going to happen, 10 is in the bag. Mark red when it falls below a 3, green when it passes a 7.

2. List last week’s prioritized tasks and if they were achieved. If not, explains why (goal is to learn what keeps org from accomplishing what it needs to).

3. List next week’s priorities (pick three P1s)

4. List any risks or blockers

5. Notes (hiring updates, reminders about team events, open questions, opportunities to shadow discovery, etc.)

Vision:
“When you are tired of saying it, people are starting to hear it.” Jeff Weiner

Trillion Dollar Coach – Eric Schmidt, Jonathan Rosenberg, and Alan Eagle

Trillion Dollar Coach – by Eric Schmidt, Jonathan Rosenberg, and Alan Eagle
Recommendation: 7/10. Date read: 4/3/21.

Details the leadership and life lessons of Silicon Valley’s most renowned coach and mentor, Bill Campbell. Bill played a critical role in the growth of Apple, Google, and Intuit, among dozens of others before he passed away in 2016. This book serves as a guide for forward-thinking leaders who are seeking to build enduring companies by empowering their people. As Bill emphasizes, people are the foundation of any company’s success. You have to start here and ensure the right team is in place while accruing respect through your own actions and the substance of your character.

See my notes below or Amazon for details and reviews.

My Notes:

Humility:
Your title makes you a manager; your people make you a leader.

“You have demanded respect, rather than having it accrue to you. You need to project humility, a selflessness, that projects that you care about the company and about the people.” Bill Campbell

Focus on being all substance rather than style or virtue signaling.

“Leadership is not about you, it’s about service to something bigger: the company, the team.”

Manager’s role:
“People are the foundation of any company’s success. The primary job of each manager is to help people be more effective in their job and to grow and develop.”

Trip reports:
“To build rapport and better relationships among team members, start team meetings with trip reports, or other types of more personal, non-business topics.”

Decision making:
“Eight out of ten times people will reach the best conclusion on their own. But the other two times you need to make the hard decision and expect that everyone will rally around it.”

First-principles:
How do you make hard decisions when the room is full of conflicting opinions? “In any situation there are certain immutable truths upon which everyone can agree…it’s the leader’s job when faced with a tough decision, to describe and remind everyone of those first principles. As a result, the decision often becomes much easier to make.”

“Define the ‘first principles’ for the situation, the immutable truths that are the foundation for the company or product, and help guide the decision from those principles.”

Compensation:
“Compensation isn’t just about the economic value. It’s a signaling device for recognition, respect, and status, and it ties people strongly to the goals of the company.”

Work the team, then the problem:

“When faced with a problem or opportunity, the first step is to ensure the right team is in place and working on it.”

“The top characteristics to look for are smarts and hearts: the ability to learn fast, a willingness to work hard, integrity, grit, empathy and a team-first attitude.”

Empowered – Marty Cagan and Chris Jones

Empowered: Ordinary People, Extraordinary Products – by Marty Cagan and Chris Jones
Recommendation: 8/10. Date read: 2/4/21.

Anything Marty Cagan touches is likely going to be an incredible, detailed resource for Product Managers. While Inspired focuses on best practices from discovery through delivery in an effective production organization (individual contributors should start with Inspired), Empowered focuses on product leadership. The book highlights the role of product leaders in creating an environment where greatness can emerge through effective coaching, staffing, team topology, product vision, product strategy, and objectives. Cagan and Jones pull everything together with case-studies from top tech companies and leaders throughout the book to show concepts in action. As with Inspired, the emphasis is on creating empowered product teams that have meaningful problems to solve, rather than features to build.

See my notes below or Amazon for details and reviews.

My Notes:

Empowered product teams:
Strong product companies give teams problems to solve rather than features to build. Teams are then empowered to solve those problems in the best way they see fit. Because the best people to determine the most appropriate solution are those closest to the problem, with the necessary skills (the product team).

Output does not equal impact: It’s far better to miss a date and ship something that solves a real pain point and delivers real business results. This is the difference between feature teams (measured by output) and empowered product teams (measured by outcome and results). 

Three characteristics of strong product teams: tackle risk early, solving problems collaboratively, accountable to results. 

Collaboration-based decision-making is not about consensus, not about pleasing the most people (dot voting), and not about having one person who's forced to make all decisions. If the decision is about enabling technology, we can debate, but defer to the tech lead. If the decision is primarily about the user or customer experience, we defer to the product designer. If the decision is about business viability, we defer to PM who collaborates with relevant stakeholders. 

“The essential point of team objectives is to empower a team by (a) giving them a problem to solve rather than a feature to build, and (b) ensuring they have the necessary strategic context to understand the why and make good decisions.” MC

Product manager responsibilities:
Ensure solutions are valuable (customers will buy the product and/or choose to use it) and viable (it will meet the needs of the business). The designer is responsible for ensuring it’s usable. The tech lead is responsible for ensuring it’s feasible. Together this team is responsible and owns results.

“Your highest-order contribution and responsibility as a product manager is to make sure what the engineers are asked to build will be worth building.” MC

Product strategy helps us decide what problems to solve, product discovery helps us figure out tactics that can actually solve the problems, and product delivery build that solution so we can bring it to market. 

The role of managers: 
“If you want to have truly empowered product teams, then your success depends very directly on these first-level people managers. If you are wondering why there are so many weak product companies in the world, this would be the primary culprit.” MC

Critical skills of managers: understand and can communicate product vision, principles, and product strategy from senior leaders. Additionally, have three important responsibilities…

1. Staffing

2. Coaching

3. Team objectives

Coaching mindset:
Developing people is job #1. If you are a manager, you should be spending most of your time and energy coaching, unlocking, and leveling up your team.

Remove impediments, clarify context, and provide guidance. 

Seek out teaching moments to help people stretch beyond their comfort zone and navigate adversity. 

“The best product leaders measure their success in how many people they’ve helped earn promotions, or have moved on to serve on increasingly impactful products, or to become leaders of the company, or even to start their own companies.” MC

Assessing product skills:
Product knowledge, process skills and technique, people skills and responsibilities. See page 41 for full details on what to look for. 

Assess these skills to determine gap analysis (1-10 scale), then provide coaching, training, reading, or exercises to help PM develop in each area. 

Interviews:
“A’s hire A’s, but B’s hire C’s.” A manager who is not an accomplished IC and who hasn’t been on the ground floor doing the work they’re speaking about can’t expect to effectively assess a candidate. As a result, they often end up hiring incompetent people.

Question to assess self-awareness: You’re a product person so I already expect that you’re strong in each. But how would you self-assess the following attributes?

1. Execution—how well do you get things done, do the right thing without being asked, and track lots of simultaneous targets?

2. Creativity—how often are you the person in the room with the most or the best ideas?

3. Strategy—how well do you get up above what you’re working on and put it into broader market or vision context then make this clear to others?

4. Growth—how good are you at figuring out ways to multiply effort through smart use of process, team management, and so on?

Objectives:
Objective is the problem to solve, key results tell us how we define success. See examples of good objectives on page 276 and page 340. 

The Coaching Habit – Michael Bungay Stanier

The Coaching Habit – by Michael Bungay Stanier
Recommendation: 7/10. Date read: 1/30/21.

This is a quick read focused on coaching others to unlock their potential. Stanier details seven core questions that are critical to successful coaching and guides readers through best practices for asking better questions. He also emphasizes how effective coaching can break the three vicious circles of creating overdependence, getting overwhelmed, and becoming disconnected. I would have preferred this to be an essay with the core concepts outlined above, rather than a book. But it’s short and well worth the read for those who want to become better leaders.

See my notes below or Amazon for details and reviews.

My Notes:

Coaching:
Coaching = helping others and unlocking their potential.

Three vicious circles:
Coaching helps break three vicious circles: creating overdependence, getting overwhelmed, and becoming disconnected. 

Creating overdependence: steal learning moments from the team, people become excessively reliant on you.

Getting overwhelmed: taking on more than you can handle and executing at a fraction of your ability because you’re spread too thin.

Becoming disconnected: getting disconnected from work that’s meaningful to you where you can have the most impact. 

Best practices for asking questions:
“What people think of as the moment of discovery is really the discovery of the question.” Jonas Salk

Ask one question at a time then shut up. Never ramble off multiple questions at once.

Stop trying to setup questions and provide backstory. Just ask it. 

Uses what questions instead of why. Rather than “why did you do that?” instead ask “What made you choose this course of action?”

When you receive an email that triggers the advice monster, instead of writing a long answer full of solutions, decide which of the most seven questions below would be most appropriate and ask that question by email. e.g. “Before I jump into a longer reply, let me ask you: what’s the real challenge here for you?”

Questions for successful coaching:

1) What’s on your mind

2) And what else?

3) What’s the real challenge here for you?

4) What do you want?

5) How can I help?

6) If you’re saying yes to this, what are you saying no to?

7) What was most useful for you? (spaced repetition)

Before saying yes, ask more questions:

• Why are you asking me?

• Who else have you asked?

• When you say this is urgent, what do you mean?

• According to what standard does this need to be completed? By when?

• If I couldn’t do all of this, but could just do a part, what part would you have me do?

• What do you want me to take off my plate so I can do this?

The Making of a Manager – Julie Zhuo

The Making of a Manager – by Julie Zhuo
Recommendation: 8/10. Date read: 1/7/21.

The best resource that I’ve read to date for individual contributors who have recently been thrust into the world of management (which requires an entirely different skill set). Zhuo provides an honest assessment of the fears and concerns that come along with venturing into a new world of management. But the bulk of the book provides insightful strategic and tactical advice for new managers. Zhuo emphasizes the primary focus on purpose, people, and process. She also provides frameworks and specific advice on how to evaluate your own performance as a manager, how to delegate, how to run meetings, how to run one-on-one’s, how to provide great feedback, how to articulate a vision, and why focus matters—to name a few.

See my notes below or Amazon for details and reviews.

My Notes:

What is your job as a manager?
Your job is not to be the best at everything or know how to do everything yourself: “Your job, as a manager, is to get better outcomes from a group of people working together.” JZ

Three areas of focus in your day to day:

1. Purpose: Outcome your team is trying to achieve. Ensure your team knows what success looks like and cares. This is the why.

2. People: Are the members of your team set up to succeed? Do they have the right skills? Are they motivated? This is the who.

3. Process: What principles govern decision making, how does your team work together? This is the how.

Evaluating your own performance as a manager:

1. What did the team achieve? Did we hit our goals?

2. Did I do a good job hiring and developing individuals? Was team engaged and working well together?

Delegation:
If you do every job yourself and are unable to delegate and coach, you’re doing work that is additive, not multiplicative. 

Delegation: “Spend your time and energy on the interaction of 1) what’s most important to the organization and 2) what you’re uniquely able to do better than anyone else.” JZ

Supporting your team:
Support and respect your reports unconditionally. If this is based on performance and you only demonstrate support or respect when things are going well, it will make things difficult for a report to be honest with you when things get tough. 

“We are more than the output of our work on a particular team at a particular moment in time, and true respect reflects that.” JZ

One-on-ones:
Focus on your report and what they need/how you can help them be more successful. Not what you need or status updates. 

• Discuss top priorities

• Calibrate on what great looks like

• Share feedback

• Reflect on how things are going

Listen and ask questions that allow your report to uncover the answer on their own: “Your job isn’t to dole out advice or ‘save the day’—it’s to empower your report to find the answer herself.” JZ

“Remember that your job is to be a multiplier for your people. If you can remove a barrier, provide a valuable new perspective, or increase their confidence, then you’re enabling them to be more successful.” JZ

Potential questions for great 1:1’s:
Identify what matters for your report and what’s worth spending time on: 

• What’s top of mind for your right now?

• What priorities are you thinking about this week?

Understand and seek to gain context and find the root of the problem:

• What does your ideal outcome look like?

• What’s hard for you in getting to that outcome?

• What do you think is the best course of action?

• What’s the worst-case scenario you’re worried about?

Support by determining how you can be of service to your report:

• How can I help you?

• What can I do to make you more successful?

Feedback:
Always ask yourself, “Does my feedback lead to the change I’m hoping for?”

You’re probably not giving feedback often enough. Start by doing it more, then dial in the type of feedback you’re giving. 

Make feedback as specific as possible, clarify what success looks/feels like, suggest next steps.

Pointer for critical feedback: “When I heard/observed/reflected on your action/behavior/output, I felt concerned because…” or “I’d like to understand your perspective and talk about how we can resolve this.”

Meetings:
Decision-making meetings:

• Good: get the decision made, includes people directly affected by the decision, clear decision-maker, presents all credible options objectively, give equal airtime to opinions, and makes people feel heard.

• Bad: people feel their side wasn’t presented well so they don’t trust the resulting decision, decisions take a long time to make (think about reversibility here), decisions keep flip-flipping, too much time is spent trying to get a group to consensus rather than escalating to decision-maker, time is wasted on rehashing the same argument.

Informational meetings:

• Good: group feels like they learned something, conveys key messages clearly, keeps the audience’s attention (storytelling, interactivity), evokes intended emotion.

Feedback meetings:

• Good: everyone on the same page for what success looks like, honestly represents the current status of work, clearly frames open questions, key decisions, or concerns, ends with agreed-upon next steps.

Who should you invite to a meeting: Which people are necessary to make your desired outcome happen?

“As a manager, your time is precious and finite, so guard it like a dragon guards its treasure stash. If you trust that the right outcomes will happen without you, then you don’t need to be there.” JZ

Process:
“Process isn’t inherently good or bad. Process is simply the answer to the question, ‘What actions do we take to achieve our goals?’…Bad process is heavy and arbitrary. It feels like a series of hoops to jump through. But good process is what helps us execute at our best. We learn from our mistakes, move quickly, and make smarter decisions for the future.” JZ

Team vision:
To define your vision for the team, ask yourself the following…

• What do you hope will be different in 2-3 years compared to now?

• How would you want someone who works on an adjacent team to describe what your team does? How far off is it from where things are today?

• What unique superpowers does your team have? When you’re at your best, how are you creating value? What would it look like to be twice as good?

• If you had to create a quick litmus test that anyone could use to assess whether your team was doing a poor job, a mediocre job, or a kick-ass job, what would that litmus test be?

Portfolio approach: a third of team works on projects that can be completed on the order of weeks, a third works on medium-term projects that may take months, another third works on innovative, early-stage ideas whose impact won’t be known for years. 

Focus:
“Few people take objectives really seriously. They put average effort into too many things, rather than superior thought and effort into a few important things. People who achieve the most are selective as well as determined.” Richard Koch

Facebook’s original photo upload feature was pretty basic and was competing against incumbents like Flickr which had more features (navigation shortcuts, search capabilities, full-screen displays). But what allowed Facebook to win was focusing on one feature, photo tagging. Triggered a network effect and drew upon the insight that the most valuable part of photos to most people are the people in those photos. 

“Executing well means that you pick a reasonable direction, move quickly to learn what works and what doesn’t, and make adjustments to get to your desired outcome.” JZ

Build, measure, learn: “Our goal is to build simple, conclusive tests that help us understand which things we should double down on and which things we should cut from the list.” JZ

Decision making:
“Most decision should probably be made with somewhere around 70% of the information you wish you had. If you wait for 90%, in most cases, you’re probably being slow.” Jeff Bezos

First Break All the Rules – Gallup Press

First, Break All the Rules – by Gallup Press
Recommendation: 7/10. Date read: 10/3/20.

A solid introduction to management and how to better develop your team. I found it particularly useful as someone who is currently trying to build this skill and help others grow in their careers. The book centers on four key elements: 1) When selecting someone for a role, select for talent. Not simply experience, intelligence, or determination. Gallup emphasizes, “As a manager, your job is not to teach people talent. Your job is to help them earn the accolade ‘talented’ by matching their talent to the role.” 2) When setting expectations, define the right outcomes, don’t prescribe the right steps. 3) When motivating someone, focus on their strengths, not their weaknesses. 4) When developing someone, help them find the right fit, not blindly moving them up to the next rung. Basic, but fundamental concepts that are worth digging into.

See my notes below or Amazon for details and reviews.

My Notes:

The focus of great managers:

• I know what is expected of me

• I have the materials and equipment I need to do my work right

• At work, I have the opportunity to do what I do best every day

• In the last seven days, I have received recognition or praise for doing good work

• My supervisor, or someone at work, seems to care about me as a person

• There is someone at work who encourages my development

Select a person, set expectations, motivate the person and develop the person:

• When selecting someone, select for talent (not simply experience, intelligence, or determination).

• When setting expectations, define the right outcomes (not the right steps).

• When motivating someone, focus on strengths (not weaknesses).

• When developing someone, help them find the right fit (not the next rung).

Talent:
“A love of precision is not a skill. Nor is it a knowledge. It is a talent. If you don’t possess it, you will never excel as an accountant. If someone does not have this talent as part of his filter, there is very little a manager can do to inject it.” Alex: talent in product is a love to create/build.

Three kinds of talent: striving = why of a person, thinking = how/decision making, relating = who of person. 

The talent alone isn’t special, you must match it with the right role. For example the relating talent of empathy with nursing. 

“As a manager, your job is not to teach people talent. Your job is to help them earn the accolade ‘talented’ by matching their talent to the role.”

“A broker with lots of desire and focus is not necessarily a better broker than one with lots of achiever and discipline. But she would certainly fit better in the entrepreneurial company, just as the broker blessed with achiever and discipline would be better cast in the more structured company.”

Focus on strengths:
“You succeed by finding ways to capitalize on who you are, not by trying to fix who you aren’t. If you are blunt in one or two important areas, try to find a partner whose peaks match your valleys. Balance by this partner, you are then free to hone your talent to a sharper point.”

Interviewing:
Past behavior is a good predictor of future behavior, but only give credit to the person’s top of mind response. If the behavior is consistent, a response will come to mind will a single prompt. If they need two or three probes to describe an example, they likely haven’t faced that scenario with any sort of regular frequency.

A person’s source of satisfaction are clues to his talent. Ask what their greatest personal satisfaction is, what kind of situations give them strength, what they find fulfilling. 

Performance Management:
Foundation = simplicity, frequent interaction, focus on the future, and self-tracking.

High Growth Handbook – Elad Gil

High Growth Handbook – by Elad Gil
Date read: 3/21/20. Recommendation: 9/10.

There are tons of resources out there for starting a company, but this book is a resource for scaling one. Gil focuses on tactical advice for scaling a company from ten employees to thousands. He emphasizes that the advice is meant to be painfully tactical in order to avoid the platitudes from investors who have never run or scaled their own company. This book is most valuable for founders, executives, and employees who are facing hypergrowth and scaling for the first time. Gil covers everything from the role of the CEO and managing the board to recruiting, organizational structure, product management, financing, and valuation. An incredible resource filled with dozens of relevant interviews with leaders who have real experience scaling great teams and products.

See my notes below or Amazon for details and reviews.

My Notes:

Focuses on tactical advice for scaling a company from 10-20 employees to thousands. Tons of resources on starting a company, this is a book that serves as a resource for scaling one. 

Most valuable for founders, CEOs, and employees who are facing hypergrowth and scaling for the first time. 

Skin in the game: “The advice presented here is meant to be painfully tactical and to avoid the platitudes you will get from investors who have never run or scaled a company.” EG

Distribution matters:
It’s a myth that most successful tech companies are product-centric. In fact, most are distribution-centric. Startups with better products get beaten by companies with better distribution channels.

“Since focusing on product is what caused initial success, founders of breakout companies often think product development is their primary competency and asset. In reality, the distribution channel and customer base derived from their first product is now one of the biggest go-forward advantages and differentiators the company has.” EG

Viability:
Tactics to stay viable = product iteration, distribution, mergers and acquisitions, moats (defensibility). 

Moats + Pricing:
“The definition of a moat is the ability to charge more.” Marc Andreessen

“Charging more is a key lever to be able to grow. And the companies that charge more therefore tend to grow faster.” Marc Andreessen

If you charge more you can allocate more to both distribution efforts and R&D.

Higher prices = faster growth. 

Product:
“Give me a great product picker and a great architect, and I’ll give you a great product.” Marc Andreessen

Product picker/manager/originator = people who can actually conceptualize new products. Great architects = people who can actually build it. 

“Great product management organizations help set product vision and road maps, establish goals and strategy, and drive execution on each product throughout its lifecycle.” EG

“Bad product management organizations, in contrast, largely function as project management groups, running schedules and tidying up documents for engineers.” EG

Product managers are responsible for:

1. Product strategy and vision (reflect the voice of the customer)

2. Product prioritization and problem solving

3. Execution (timelines, resources, and removal of obstacles)

4. Communication and coordination

Characteristics of great product managers:

1. Product taste

2. Ability to prioritize

3. Ability to execute

4. Strategic sensibilities (how is the industry landscape evolving?)

5. Top 10% communication skills

6. Metrics and data-driven approach

Interviewing PMs:

1. Product insights

2. Contributions to past successful products

3. Prioritization

4. Communication and team conflicts

5. Metrics and data

Product Management Processes:

1. PRD templates and product roadmaps: Build agreement and clarity on what you are building. What are the requirements for the product itself? Who are you building this for? What use cases does the product meet? What does it solve for and explicitly not solve for? What are the main features and what does the product do? What are the main product dependencies? A PRD may include wireframe that roughly sketch out the product user journey.

2. Product reviews

3. Launch process and calendar

4. Retrospectives

Small, self-sufficient teams:
“There are exceptions, but in most cases, you need original thinking and speed of execution, and it’s really hard to get that in anything other than a small-team format.” Marc Andreessen

Design: Usability, how do we design this? Create the optimal user experience.

Engineering: Feasibility, how can we build this? How can technical road map drive product and vice versa. 

Product: Viability, should we build this? Set product vision and road map to ensure the company builds a product that the user needs. Make trade-offs between design, engineering, and business concerns.

Traits to look for in executives:

1. Functional area expertise: Do they understand the major issues and common failure points for their functions?

2. Ability to build and manage a team in those functional areas: Do they know how to motivate people in their functions?

3. Collegiality: Do they do what’s right for the company even if it’s not in their best interest? Create mutually supportive environment.

4. Strong communication skills: Do they have cross-functional empathy?

5. Owner mentality: Do they take ownership of their functions and make sure they are running smoothly and effectively?

6. Smarts and strategic thinking skills: Do they think strategically and holistically about their functions? Are they first principle thinkers? Can they apply their expertise in knowledge in the context of your company, team, and product? Or do they just try to implement exactly what they did in their last role?

External hires: “The way to retain people who are performing and who you really want to retain is to hire someone that they can learn from.” Keith Rabois

Flagship offices in the era of remote work:
Onboarding at headquarters helps to build initial connections and creates significant long-term value. 

With remote teams, create a great teleconferencing setup and consider the timing of your key meetings.

Who to emulate?
“I think people should select carefully the companies they seek to emulate and learn lessons from.” Patrick Collison

With great software companies in China (JD, Tencent, Alibaba), there’s a lack of entitlement, complacency, and a determination that there’s a void of in Silicon Valley.

Interviewing (to remove unconscious bias):

1. Articulate the relevant qualifications for every role.

2. Designing specific questions to assess for each qualification.

3. Limiting the domains that each interviewer has to assess. Don’t go in and try to decide “Should we hire this person?” What you want to focus on is, “Does this person meet what we need on these two things?” When you’re trying to assess people on five different areas, it’s really hard, and you start to take shortcuts/allow biases to factor in. 

4. Create rubrics to help interviewers evaluate answers to the questions that they’re asking.

What You Do Is Who You Are – Ben Horowitz

What You Do Is Who You Are – by Ben Horowitz
Date read: 11/14/19. Recommendation: 8/10.

“Culturally, what you believe means nearly nothing. What you do is who you are.” Horowitz’s latest book is all about leading and creating a purposeful culture at work. He defines culture as a set of actions, rather than the beliefs or corporate values that might be taped on the wall. While he pulls relevant case studies in the modern era – Uber, Netflix, McDonald’s – the book is built upon historical accounts of Toussaint Louverture, Genghis Khan, and the samurai. Each highlights a key lesson in culture, leadership, and how to create meaning. Horowitz reminds leaders that their perspective on the culture isn’t relevant – that’s rarely what your people experience. The real question is what employees have to do to survive and succeed? What behaviors get them ahead?

See my notes below or Amazon for details and reviews.

My Notes:

Why culture matters:
Startups who outsource engineering almost always fail: “It turns out that it’s easy to build an app or a website that meets the specification of some initial idea, but far more difficult to build something that will scale, evolve, handle edge cases gracefully, etc.” BH

“We at Apple had forgotten who we were. One way to remember who you are is to remember who your heroes are.” Steve Jobs

“Culture begins with deciding what you value most.” BH

Culture = a set of actions, not beliefs. 

Virtues vs. Values:
Virtues are what you do. Values are what you believe.

Corporate values are worthless because they emphasize beliefs instead of actions.

“Culturally, what you believe means nearly nothing. What you do is who you are.” BH

Create shocking rules:
Should shock people and force them to ask why and must be something they encounter on a daily basis. This helps program the culture. 

Tom Coughlin (New York Giants): If you are on time, you are late. Meetings would start five minutes early. Fined players who failed to be there by that time. It was memorable, forced people to ask why, encountered daily, and helped build discipline.

Leadership:
“When you are a leader, even your accidental actions set the culture.” BH

Emphasize the “why” behind your values and the vision with every chance you get. That’s what gets remembered. 

Act right: “As a leader, you can float along in a morally ambiguous frame of mind until you face a clarifying choice. Then you either evolve or you wall yourself up in moral corruption.” BH

“Your own perspective on the culture is not that relevant. Your view or your executive team’s view of your culture is rarely what your employees experience…The relevant question is, what must employees do to survive and succeed in your organization? What behaviors get them included in, or excluded from, the power base? What gets them ahead?” BH

“Good intentions, pursued without meticulous forethought and follow-through, often lead to catastrophe.” BH

What you do must matter:
Above all else, employees want to know that they matter, they’re making a difference, there’s meaningful work to be done, and they’re moving the bigger picture forward. Without this, it’s impossible to get people to care. 

If a culture can’t make quick decisions or has a void in leadership, it becomes defined by indifference.

Disagree and commit:
As a manager, the worst thing you can do is undermine decisions made above you – creates cultural chaos, makes your team feel marginalized and powerless, and end result is apathy and attrition. 

The way you get to the place of being able to articulate a decision you might not agree with is by asking why. It’s your job to understand the reasoning behind a decision, otherwise you have failed your team. 

Telling the truth isn’t natural. It requires courage. The easy thing to do is to tell someone what they want to hear.

You might not convince everyone you’re right. But everyone must feel heard and that you’ve acknowledged their concerns. This is the path towards disagreeing and committing. 

It Doesn’t Have to Be Crazy at Work – Jason Fried and David Heinemeier Hansson

It Doesn’t Have to Be Crazy at Work – by Jason Fried and David Heinemeier Hansson
Date read: 5/7/19. Recommendation: 8/10.

The book outlines lessons from Basecamp and how to run a calm company. Refreshing resource, particularly for those who get caught up in the chaos of work. They discuss why calmness is a productive emotion and the work structure they use at Basecamp to help sustain that. Fried and Heinemeier Hansson also dig into work ethic, the danger of meetings, the importance of saying no, the myth of low-hanging fruit, why they ship before they test, and the rationale for why they only have a single product. It’s a great, short read that will help you challenge the status quo.

See my notes below or Amazon for details and reviews.

My Notes:

Calmness = productive emotion:
Goal at Basecamp is to be a calm company. Similar to Phil Jackson’s approach to pre-game speeches or halftime speeches. Remain calm and in control.

“Calm requires getting comfortable with enough.”

“Becoming a calm company is all about making decisions about who you are, who you want to serve, and who you want to say no to. It’s about knowing what to optimize for. It’s not that any particular choice is the right one, but not making one or dithering is definitely the wrong one.”

In victory, learn when to stop (Robert Greene, 48 Laws of Power): 
Basecamp currently generates tens of millions of dollars in profit and they’re happy with that. Not obsessed with doubling or tripling market share. Focused on serving existing customers well. 

Example, they’ve kept fixed monthly fee instead of per-seat business model. Helps them avoid conflicts of interest where biggest customer holds power over the product and controls your time. 

Also, why they only have a single product. 

Work structure:
Projects are typically six weeks cycles, followed by two weeks to wander and decompress. 

Monthly “heartbeats” written by the team lead to summarize progress that’s been made. Boils key learnings down to essential points. Automatically removes the noise of the day-to-day by taking a broader perspective.

Work ethic:
Effectiveness > busyness.

Point of diminishing returns: “Creativity, progress, and impact do not yield to brute force.”

Make the best decision that you’re able to now and avoid indecision: “Accept that better ideas aren’t necessarily better if they arrive after the train has left the station. If they’re so good, they can catch the next one.”

Saying no and getting more done:
Say no, claw back time: “The only way to get more done is to have less to do.” (Similar to Nassim Taleb’s quote, “You want maximal free time, not maximal activity, and you can assess your own ‘success’ according to such a metric.”).

“No is no to one thing. Yes is no to a thousand things.”

“When you say no now, you can come back and say yes later.”

“No is calm but hard. Yes is easy but a flurry.”

Myth of low-hanging fruit:
The idea that you can instantly move needles because you’ve never tried before is delusional. Almost always requires difficult work.

Hiring and talent:
“Stop thinking of talent as something to be plundered and start thinking of it as something to be grown and nurtured.”

Ship it:
Simulated environments provide simulated answers. If you want to know the truth about your product, you have to ship it and see how real customers use it in their natural environment. 

Basecamp doesn’t beta test. They don’t put things in front of users before they’re ready for production. Slow and timid response to feedback might help them catch a few things, but they value speed and conviction over safety. 

Building a Story Brand – Donald Miller

Building a Story Brand – by Donald Miller
Date read: 4/25/19. Recommendation: 9/10.

Honestly, the only marketing book you should ever need. The heart of the book is about clarifying and simplifying your message. Miller presents his strategy in a seven-point framework that forms the foundation of all great stories. Whether an artist or entrepreneur, it’s a great resource to help you improve your communication. I’ve already used the framework to overhaul my own website and improve my messaging in the products I’m building at work. You’ll get the most value out of this book if you follow (and actually complete) the exercises, chapter by chapter.

See my notes below or Amazon for details and reviews.

My Notes:

Two biggest mistakes in marketing:
-Failure to focus on aspects of product that help people survive/thrive.
-Requires too much energy from customer to understand what’s in it for them. 

Storytelling:
“Story is the greatest weapon we have to combat noise, because it organizes information in such a way that people are compelled to listen.”

The best products don’t always win. The best communicators do.

Say less and communicate clearly, otherwise customers will give up trying to organize and make sense of all the data.

Steve Jobs learned this through his experience with Pixar. In 1983, Apple launched their computer Lisa and took out a nine-page ad in the New York Times. When he returned to the company, took two words and put them on a billboard: “Think Different.”

Seven major elements, make up the SB7 framework:
Character, Problem, Guide, Plan, Call to Action, Avoid Failure, Success.

Three questions you need to answer to drive engagement:

-What do you offer? How will it make my life better? What do I need to do to buy it?

Above the fold: Promise an aspirational identity, promise to solve a problem, state exactly what you do.

Similar to: What is this? What’s in it for me? What do I do next?

1) A Character:
The customer is the hero, not you. What do they want?

Define something they want and open up a gap. 

Make it about survival. 

Make it a single focus.

2) Has a Problem:
Villain should be root source, relatable, singular, and real.

Three dimensions: external problems, internal problems, philosophical problems.

6) And Calls Them to Action
Major life decisions aren’t made until you’re challenged to do so. Must be challenged by outside forces.

Be bolder in calls to action. If they’re soft, they’ll be ignored.

If you don’t clearly invite customers to take a journey with you, they won’t. 

People are drawn to clarity. Have clear calls to action so they know what they need to do next. 

Transitional calls to action are different. Instead of “buy now” they allow you to establish credibility, create reciprocity, and position yourself as the guide (think free information, testimonial video, free trial period). 

7) That Helps Them Avoid Failure
If we don’t bring up the negative stakes early and often, story will fall flat.

What are you helping your customer avoid? What does failure look like?

8) And Ends in Success
Be specific – JFK didn’t say he wanted to build a “highly competitive and productive space program,” he said “we’re going to put a man on the moon.”

Identity transformation: From, To (anxious, glum to carefree, radiant).

The Messy Middle – Scott Belsky

The Messy Middle – by Scott Belsky
Date read: 10/20/18. Recommendation: 9/10.

More than a business book, and that’s what I loved about it. It’s a book about embracing the long game and leading through ambiguity–whether you’re a founder, entrepreneur, or artist, you’ll find relevance. Belsky details the endurance it takes to bring an idea to life. It’s not always as pretty as the beginning or end, but the middle is worthy of equal attention since it’s where most of the journey takes place. As a product manager, I found the book to be particularly insightful for my daily work and career. The next time I’m asked for a great product book, I’ll be recommending this. But again, the beauty of this book is that it’s relevant for anyone who’s building something from nothing. Those who are leading others (or themselves) through uncertainty will benefit greatly from it. Far from a generic business book with the same recycled ideas, it’s original, practical, profound, and one of the best books I’ve read all year.

See my notes below or Amazon for details and reviews.

My Notes:

You cannot travel the path until you’ve become the path. Embracing the middle is the only way through.

Values/Principles:
-“The truth about telling the truth is that it does not come easy for anyone. It’s not natural or organic. The natural thing to do is tell people what they want to hear. That makes everybody feel good…at least for the moment. Telling the truth, on the other hand, is hard work and requires skill.” Ben Horowitz

-“There is no better measure of your values than how you spend your time.” SB, accounting of how you spend your minutes is hard truth of your values.

-Routines backfire when you do them without thinking. Throw a wrench in every now and then to see if it feels liberating and is no longer relevant/effective.

-Sometimes you guard your time too closely. Fluidity/flexibility to adapt is important, or else you won’t reach full potential. Need to create and preserve some margin of downtime in your day to accommodate opportunities. 

-You deserve this and you are enough. There’s a part of all of us that fights our own progress. Overcome these insecurities and doubts.

-"You are not your org chart, your department budget, or your title. Don’t let success at a company prevent you from pursuing scary and wonderful new opportunities to build.” Hunter Walk

Endurance:
-“You need to do your fucking job.” What Belsky would tell himself before going into a tough meeting, negotiation, or firing someone.

-“Playing the long game requires moves that don’t map to traditional measures of productivity.” SB

-“Curiosity is the fuel you need to play the long game.” SB 

-Resourcefulness is a competitive advantage. “Resources become depleted. Resourcefulness does not.” SB

-80% on boulders, 20% on pebbles.

Lead your team:
-Teams need to be reminded of where they are and progress they’ve made. Call out landmarks you pass and the terrain ahead.

-When discussing your teams efforts so far, weave in stories and leverage the perspective that excites you the most.

-Your perspective during trying times will help your team overcome moments of self-doubt.

-Not all meetings end with a solution, quit seeking a false sense of closure. Instead actively lead through a process of self-discovery.

-Unresolved conversations are draining. If you can’t provide closure, add energy, turn negative into positive. 

-“Your story has more gravity than you realize. Your job is to help your team make sense of the strategy–what they’re seeing, doing, and working toward. You are the steward of your team’s perspective, and there is always a way forward so long as you explain it.” SB

-Don’t aggressively market yourself, celebrate the people on your team and empower great makers. “Ego is rust. So much value and potential are destroyed in its slow decay.” SB

-Pick your fights and don’t deprive others of their own process. Sometimes the best way to instigate change is to plant questions as seeds and let them take root so you can avoid immediate reactions. 

Conviction:
-“For extraordinary outcomes, seek conviction in your work and build teams that value conviction over consensus.” SB

-Hesitation breeds incrementalism.

-Most effective way to communicate a vision is to declare it, rather than blunting blow with a comforting narrative that makes it sound less drastic.

-Progress is only possible once a decision is made. Can always backtrack and adjust as you learn along the way. Keep moving!

-Make your mind up quickly and go with the option that feels most right at first (don’t survey every available option). Otherwise you’ll waste time and energy searching for alternatives that may only be mildly more beneficial.

Self-awareness:
-Self-awareness is the greatest competitive advantage for a leader.

-Your sense of self shifts when you’re at a peak or in a valley. 

-Effort to understand how your mind works is only path to reliable self-awareness during intensity/stress.

-“You cannot win unless you know how you’re most likely to lose.” SB

-“Knowing when to ignore your experience is the true sign of experience.” -John Maeda

Ambiguity:
-Avoid temptation to describe what you’re building in context of what already exists (i.e. “It’s Airbnb for X”). 

-When you feel overwhelmed, remember the vision. Compartmentalize your ideas, look ahead, worry less about day-to-day concerns. 

-When you feel lost in ambiguity, ask a different question. i.e. Not “why aren’t people signing up?” but “what kinds of people would benefit most?”

-When you’re building something new, focus on asking the right questions instead of having the right answers. 

Defy prescribed roles:
-Directing blame and expressing disappointment take more energy than tackling whatever you’re criticizing. Take the initiative, even if it falls outside of your job description.

-“There is rarely a scarcity of process or ideas but there is often a scarcity of people willing to work outside the lines.” SB

-“You’re either a cog in the system or a designer of better systems…challenge every system you find yourself confined by.” SB

-Asking for permission to do what you know needs to be done will yield hesitation at best, rejection at worst.

Prioritize your team:
-“I have met many founders who obsess over product and steamroll their team. Most of them have failed. Team comes first.” SB

-If you want to execute well over time or make great products, prioritize your team over your goals and tend to your team before your product.

Hiring:
-Hire people seeking a journey rather than a particular outcome.

-Closing the confidence gap of new hires is more important than closing skills gap. Building confidence is important if you want to unleash someone’s potential. 

-Maturity and perspective > age and accolades.

-Best reason to fire people who aren’t performing is to keep your best people.

-Salary bands: subconsciously biased by age, years of experience, gender, and other characteristics that don’t correlate with indispensability. 

Founders:
-“What distinguishes great founders is not their adherence to some vision, but their humility in the face of the truth.” Paul Graham

-Greatest thinkers anchor ideas around a central truth they believe is unique and unrealized by others, but embrace questions when someone challenges them…they don’t look the other way.

-Poor leaders are too worried about being loved. The best founders have conviction in their ideas and aren’t hedging by spreading resources thinly across too many ideas. 

-Hold on to the openness, humility, and brashness you had in the begging.

Product:
-Speed through the generic stuff, but take time to perfect the things you’re most proud of. This is what differentiates your product, so it deserves a disproportionate investment of resources.

-Uniqueness of your product needs to be baked in, not sprinkled in at the end. Otherwise it’s likely to taste bland.

-Customers don’t engage with functionality, they engage with experiences. Make it more human friendly and accommodating to natural human tendencies.

-Competitive advantage is as much about what you choose to let go and not be, as it is about what you focus on. 

-One feature in, one feature out. Keeps you focused on simplicity.

-Having to explain your product, least effective way to engage new users.

-Empathy for your customers and humility in your market are powerful filters. Focus on these before you fall in love with your solution.

-Greatest brands developed by playing at far end of the spectrum and not trying to be everything to everyone. “Playing to the middle makes you weak.” Don’t give up your edge to appeal to broader audience.

-Engage emotionally as you create, but detach yourself when you’re evaluating.

Innovation:
-Every product or service in your life either helps you spend or save time. Best products remove a daily friction.

-Don’t be too different, familiarity drives utilization. Train customers on something new only when it’s core to what differentiates your product. Helps reduce cognitive friction.

-Big part of innovation is saying ‘you know what I’m really sick of?’ What frustrates you likely frustrates many others.

-True innovators value art up front and compete against incumbents through stuff that doesn’t intuitively scale. Give your customers something precious, uniquely personal, emotional, and seemingly scarce that cannot be easily scaled, automated, or commoditized. Preserving the art in your business gives it a soul that people can connect with. 

-At the beginning, must run manual experiments, spend endless amount of time with customers, and tinker until you find something special.

The Product Lifecycle:

1. Customers flock to a simple product.

2. The product adds new features to better serve customers and grow the business.

3. Product gets complicated.

4. Customers flock to another simple product.

The First Mile:
-Fewer options, shorter copy, simpler steps.

-Need to prime your audience to know, 1) Why they’re there, 2) What they can accomplish, 3) What to do next.

-30% of your energy should be allocated here. Top of funnel for new users, deserves to be well thought out. 

-Remember, people are lazy, vain, and selfish. You have 30 seconds to engage and address each concern.

-Best hook is doing things proactively for customer. Once you help them feel successful and proud, will engage more deeply and take time to learn and unlock the greater potential of what you’ve created. 

Measuring Success:
-Always ask “what is the real goal here?” Answer is rarely as measurable as you may think.

-Avoid too many measures, the more numbers you’re tracking, the less attention you pay to any of them.

-Boil your business down to one or two core metrics.

-Prefer, a referral network for independent professionals, uses a single metric, “number of working pairs.” Allows them to focus on what matters instead of getting caught in surface measures like revenue or downloads.

-Iconic and breakthrough product insight are not the result of trying to improve a metric. Square’s iconic UX requiring everyone to sign using a finger instead of bypassing small transactions.

Investors:
-“For strong companies, financing is a tactic. For weak companies, financing is a goal.” SB

-Is the team attempting to defy a likely outcome or make it happen in a better way? Invest in the latter. Uses forces already in play.

Editing:
“The question that I find most helpful to ask is, ‘if you had to keep 10 percent, which 10 percent would you keep, and if you had to, absolutely had to, cut 10 percent, which 10 percent would you cut?’” Tim Ferriss

Desire to Learn:
-Warren Buffett spends 80% of each day reading. When asked about keys to success, Buffett pointed to a stack of books on his desk and said, “Read five hundred pages like this every day. That’s how knowledge works. It builds up, like compound interest. All of you can do it, but I guarantee not many of you will do it.”

-Annual letters to investors, Buffett is self-reflective and self-deprecating. Admits when he struggles to understand something or has made dumb decisions. Remarkably open to changing his mind. All because of his persistent desire to learn.

Your Move – Ramit Sethi

Your Move: The Underdog’s Guide to Building Your Business – by Ramit Sethi
Date read: 9/20/18. Recommendation: 8/10.

Ramit Sethi is one of my favorite humans and writers (I Will Teach You to Be Rich is a gem, if you haven’t read it). He’s someone who gets it. Whether it’s finance, or in this case business, he’s always focused on the things that matter and assigning things their proper weight. In Your Move he offers insight into handpicking customers, being more selective about who you target, and why that’s fundamental to success. He emphasizes authenticity and crafting a message that resonates with your target audience’s hopes, dreams, pain points, and fears. It’s a book that should be able to point you in the right direction whether you’re struggling with your initial idea, defining your audience, or putting yourself and your product out there. There’s actionable insight for each.

See my notes below or Amazon for details and reviews.

My Notes:

A successful business doesn't mean more money. It means more success, peace of mind and time.

Don't give things away for free:
-People value what they pay for
-Huge difference between free reader and paying customer
-Paying customer is far more likely to engage/open/use whatever they've paid for

"Most people reading this will not become millionaires because it involves extremely hard work and insane perseverance." -RS

Invisible risk of doing nothing > risk of starting a business

If you create value, people will be more than happy to pay for it.

Authenticity matters. Listening matters. When you sit down with customers, encourage them to open up by saying "Tell me about that." Or if you're sending emails, ask "What are you struggling with today?"

Make sure you've identified and are talking with your target market.
-If Ramit had talked to people his parent's age when writing his first book, he probably would have heard something about saving for retirement earlier. That message doesn't resonate with someone in their early 20s who wants to know what to do with their money, make it work for them, and buy a round of drinks for their friends.

Be selective and handpick your customers
-Allows you to target wants, needs, hope, fears, desires of that audience with pinpoint accuracy (and create products they want).
-"Students for life" philosophy.
-Regularly encouraging people to unsubscribe from newsletter (those who stick around are highly committed and engaged).

"Your biggest challenge is customer selection. You pick the right customer, you win. You pick the wrong customer, you lose. Focus on helping great people get better." -Marshall Goldsmith

Learn to embrace mistakes, otherwise, you get stuck in analysis paralysis (thinking instead of acting).

"Focus on being decisive and less on trying to make the 'right' decision. You'll never know until you try, and if you're wrong, you can always try again." RS

Beginners focus on the wrong things – worry about minutiae that won't change a thing and ends up exhausting.

Experienced pros have gone through this and know what to pay attention to (and what to ignore).

"Anyone can be 'efficient'–meaning they can do a given task pretty well. But very few can be 'effective,' meaning they select the right things to work on in the first place. Focusing on the right things is a true superpower." RS

Focus on your audience more, your competition less.

"Be different to be better. Don't be different for the sake of being different." RS

When you nail the right audience, price is a mere triviality. People will pay substantial money if you're solving a problem that's important to them AND they believe you can solve it.

Systems mentality: Life is always going to be messy. Successful people don't rely on "motivation or "working harder" to make things happen. They have systems for the big wins and let the inconsequential stuff fall by the wayside.

To sell you need to know four key things about your customers: their hopes, dreams, pain points, and fears.

Get comfortable being uncomfortable. The things that worked from $0 to $100,000 won't always work when you're trying to crack $500,000.

Change the words you use to sell your products and you can drastically increase revenue.
-Focus on the reader and their pains, challenges and frustrations as they relate to your niche.
-Articulate their biggest hopes, dreams, and goals.
-What do they want? What's frustrating? What's going on inside their heads?

Product or service tiers (i.e. intro, intermediate expert) changes the question from if I should buy, to which should I buy?

If you view yourself as their trusted advisor and you have a product that will help them, you should be doing everything in your power to let them know about it.

"Stop and ask yourself: Are your products awesome? Do they really help people? If the answer is 'No,' then you need to make a better product." Graham Cochrane

30% Raise:
-Change the words on your promotional pages (take focus off product, shift towards customers)
-Offer more expensive option (tiered pricing)
-Begin selling sooner and more often