The Innovation Stack – Jim McKelvey

The Innovation Stack – by Jim McKelvey
Date read: 10/25/21. Recommendation: 9/10.

One of the most compelling and entertaining business narratives that I’ve read. McKelvey details his first-hand experience launching Square alongside Jack Dorsey. The book dives into what entrepreneurship truly is, how to identify and articulate meaningful problems, and how to create a differentiated business model through your own innovation stack—a series of interlocking solutions that serve to create defensibility for your business. But as McKelvey points out, an innovation stack isn’t a neatly planned map of things that you anticipate building ahead of time. Instead, it’s a series of reactions to real problems and challenges that you stack on top of each other to deliver a solution that drives results.

See my notes below or Amazon for details and reviews.

My Notes:

Innovation Stack:
“The problem with solving one problem is that it usually creates a new problem that requires a new solution with its own new problems. This problem-solution-problem chain continues until eventually one of two things happens: either you fail to solve a problem and die, or you succeed in solving all the problems with a collection of both interlocking and independent innovation. This successful collection is what I call an Innovation Stack.” JM

“An Innovation Stack is not a plan, it is a series of reaction to existential threats.” JM

“You cannot view the elements of an Innovation Stack individually. The innovation evolves as a whole. No single element can be inserted or removed without changing the behavior of the other elements.” JM

Square’s Innovation Stack:

1. Simplicity: focused on a known price—one price, a percentage of the transaction for everyone at all times, no hidden fees. Consequence is that even on small transactions, Square was still paying per transaction fee to card networks so they were losing money. Forced to recoup these by having a huge volume of other transactions so they need to scale.

2. Free sign-up: Pricing model could only work if they grew rapidly, so created a fast, frictionless, free sign up.

3. Cheap hardware

4. No contracts: hardly spoke to customers in early days to keep costs down.

5. No live support: “We took our lack of live customer service very seriously. It was not just a way to keep our costs down, it forced us to develop more innovation to further reduce the need for customers to contact us.” JM

6. Beautiful software

7. Beautiful hardware: “By intentionally sacrificing function for attention we got people to notice that something was happening outside the city walls.” JM

8. Fast settlement: “Speed was critical for several reasons. It delighted customers and kept our growth humming, but more important, it eliminated all those ‘Where’s my money?’ Support calls.” JM

9. Net settlement: Simple pricing allowed them to know what to send to the merchant daily. Rest of industry spent days before they knew cost of a charge which involved complicated math to determine balance.

10. Low price

11. No advertising

12. Online sign-up

13. New fraud modeling

14. Balance sheet accountability

These were not planned inventions. They were reactions to real problems and challenges that Square then stacked on top of each other to deliver a solution that drove results. 

Square’s innovation stack of 14 elements makes it incredibly hard to replicate. To copy even one element correctly is likely around a 75% chance. Stack that on top of 13 other elements and you have less than a 5% chance to copy the product correctly. 

Control:
In the early days, it’s important to control every aspect of your product. Especially physical products. If you’re not doing it by hand and you’re outsourcing, the feedback loop becomes too drawn out to make quick corrections. Because of this, in the early days of Square, their hardware changed every week. 

Commitment:
“Commitment can substitute for qualification.” JM

Management:
“This is why I laugh when people copy Google’s management practices. Twenty billion dollars of free cash flow fixes a lot of managerial mistakes.” JM

Timing:
Cut through the infinite options by asking, “When should we begin?” There are two answers to this: now or later. “Now is often the right answer. In this world of highly similar products, speed is a huge advantage.” JM

Observation + skin in the game:
“Entrepreneurs fighting for survival outside the civilized market don’t build mathematical models of what will happen, they just do it and observe. Jumping rope with a bungee cord isn’t impossible; you try, experience what happens, and make adjustments. The effects of each element on the other elements, while impossible to predict, are relatively easy to observe and respond to.” JM

Competition:
If your industry is growing slowly through incremental improvement, copying competitors and watching your competitors more closely than you watch customers is a sound strategy. 

Entrepreneurial companies should focus on the customer, typically a customer who is new to the market, since a company can only develop an innovation stack by being laser-focused on customers. Maintain focus on customers, even in face of direct attack from competition. 

Working Backwards – Colin Bryar and Bill Carr

Working Backwards: Insights, Stories, and Secrets from Inside Amazon by Colin Bryar and Bill Carr
Date read: 10/8/21. Recommendation: 8/10.

This is a great directional resource for companies to fine-tune their own top-performing culture. Bryar and Carr cover everything from leadership principles and hiring during their time at Amazon to the product development approach, relentless focus on customer experience, and communication processes. I’m a big fan of Amazon’s communication style, favoring narratives (written documents) over slides. While I believe the themes and general concepts found in this book are valuable, when you read books like this there’s always a temptation to apply the entirety of the content back to your own company and experience. But the exact processes and systems that work for Amazon will not work the same way for your business. The real value is using this as inspiration then leveraging interesting concepts or approaches to fit your team.

See my notes below or Amazon for details and reviews.

My Notes:

Amazon’s culture:
“Our culture is four things: customer obsession instead of competitor obsession; willingness to think longer term, with a longer investment horizon than most of our peers; eagerness to invent, which of course goes hand in hand with failure; and then, finally, taking professional pride in operational excellence.” Jeff Bezos

Amazon’s leadership principles:

1. Customer obsession: Start with customer and work backwards

2. Ownership

3. Invent then simplify

4. Are right, a lot: “Leaders are right a lot. They have strong judgment and good instincts.”

5. Learn and be curious

6. Hire and develop the best

7. Insist on the highest standards

8. Think big: “Thinking small is a self-fulfilling prophecy”

9. Bias for action: “Speed matters in business”

10. Frugality: “Accomplish more with less. Constraints breed resourcefulness, self-sufficiency, and invention. There are no extra points for headcount, budget size, or expense.”

11. Earn trust

12. Dive deep

13. Have backbone; disagree and commit

14. Deliver results

Two-pizza teams are:

• Small: no more than ten people.

• Autonomous: No need to coordinate with other teams to get their work done.

• Monitored in real-time

• Business owners

• Led by a multidisciplined top-flight leader

• Self-funding: team’s work will pay for itself

• Approved in advance by leadership

Autonomous team setup:

1. Well-defined purpose: “For example, the team intends to answer the question, ‘How much inventory should Amazon buy of a given product and when should we buy it?’

2. Boundaries of ownership are well understood

3. Metrics to measure progress are agreed upon upfront

Specifics of how the team will solve its challenge and achieve its goal is entirely up to the team. They must figure that out for themselves.

Narratives:
Six-pager: Describe, review, or propose just about any idea, process, or business. Maximum length 6 pages.

PR/FAQ: Working backwards process for new product development.

“The reason writing a good 4 page memo is harder than ‘writing’ a 20 page powerpoint is because the narrative structure of a good memo forces better thought and better understanding of what’s more important than what, and how things are related. Powerpoint presentations somehow give permission to gloss over ideas, flatten out any sense of relative importance, and ignore the interconnectedness of ideas.” Jeff Bezos

Courage Is Calling – Ryan Holiday

Courage Is Calling – by Ryan Holiday
Date read: 10/2/21. Recommendation: 9/10.

Ryan is a great writer and his books follow an effective formula of short chapters, quotable content, and abbreviated stories from history to illustrate his points. This is a great introduction to courage as the pinnacle of all virtues. As Holiday emphasizes, if the life you’re leading doesn’t demand acts of courage, you’re living a boring life.

See my notes below or Amazon for details and reviews.

My Notes:

Lead by example:
“If we are going to indict anyone for their cowardice, let it be silently, by example. Waste not a second questioning another man’s courage. Put that scrutiny solely on your own.” RH

“This is why the truly brave are often rather quiet. No time for, no interest in, boasting. Besides, they know that bragging puts a target on their back, and what is to be gained from that? That doesn’t mean they’re timid or self-effacing.” RH

“Character is above all the ability to disregard insults or abandonment by one’s own people. One must be willing to lose everything. There is no such thing as half a risk.” RH

Skin in the game: 
“A leader cannot sit in some ivory tower or behind thick castle walls. They cannot protect themselves from every danger and risk while they let their followers or employees or soldiers take the brunt of what the world throws at us. No, a leader must have real skin in the game.” RH

August 30, 1945: General Douglas MacArthur touches down in Japan. Fighting between Allies and Axis had just ceased. No enemy boots had touched Japanese soil in six years. Told his team to leave their weapons. Instead walked into the country with fearlessness and complete confidence to show it was over. “Tokyo itself went without a shot. MacArthur’s entrance told them it was over…and they believed him. A more trepidatious commander could have never pulled it off, nor an angry or vengeful one.” RH

Apathy:
“The opposite of courage is not, as some argue, being afraid. It’s apathy. It’s disenchantment. It’s despair. It’s throwing up your hands and saying, ‘What’s the point anyway?’” RH

Growth:
“The fear you feel is a sign. If courage is never required in your life, you’re living a boring life. Put yourself in a position that demands you leap.” RH

Indecision:
“At the top, there are no easy choices. All are between evils, the consequences of which are hard to judge.” Dean Acheson

“What cowardice fears most of all is the making of a resolution.” Soren Kierkegaard

“What you fear is consequences. So you keep deliberating hoping you can put them off.” RH

“We claim we debate so we can get to the right decision, that we need more information. In truth, we are delaying. We don’t want to leave the comfort of the status quo. We don’t want to have to own the consequences.” RH

Virtue:
“The virtues are like music. They vibrate at a higher, nobler pitch.” Steven Pressfield

“Courage is not simply one of the virtues, but the form of every virtue at the testing point.” C.S. Lewis

Four Thousand Weeks: Time Management for Mortals – Oliver Burkeman

Four Thousand Weeks: Time Management for Mortals – Oliver Burkeman
Date read: 9/18/21. Recommendation: 9/10.

I started this book while standing in a two-hour-long security line at Denver International Airport and there was perhaps no better book I could have chosen at that moment. Burkeman is a tremendous writer. He reaches surprising depth in such a short amount of time by distilling his ideas into their simplest form. The Antidote is the same way and was one of my favorite books for years. In this book, he addresses the anxiety that’s built from our own busyness and the shortness of life. While we obsess over an imaginary future state where we’ve escaped all problems and mastered our time, we’re actually missing out on life’s most meaningful moments. Burkeman rejects productivity gurus and time management hacks as making matters worse by further fueling our anxiety. Instead, he suggests letting go of the futile attempts to master our time. This starts with reconciling what’s within our control, taking ownership of those things, improving our decision-making, and embracing the art of patience. It’s a refreshing take on how to make the most of our time here.

See my notes below or Amazon for details and reviews.

My Notes:

The Efficiency Trap:
The more efficient you get, the more you become a “limitless reservoir for other people’s expectations.” Jim Benson

To avoid the efficiency trap, you need an anti-skill—a willingness to avoid such urges—“to learn to stay with the anxiety of feeling overwhelmed, of not being on top of everything, without automatically responding by trying to fit more in.” OB

“Convenience culture seduces us into imagining that we might find room for everything important by eliminating only life’s tedious tasks. But it’s a lie. You have to choose a few things, sacrifice everything else, and deal with the inevitable sense of loss that results.” OB

“But the undodgeable reality of a finite human life is that you are going to have to choose.” OB

Ownership:
“Rather than taking ownership of our lives, we seek out distractions, or lose ourselves in busyness and the daily grind, so as to try to forget our real predicament. Or we try to avoid the intimidating responsibility of having to decide what to do with our finite time by telling ourselves that we don’t get to choose at all.” OB

Expectations vs. reality:
“When you’re trying to Master Your Time, few things are more infuriating than a task or delay that’s foisted upon you against your will, with no regard for the schedule you’ve painstakingly drawn up in your overpriced notebook. But when you turn your attention instead to the fact that you’re in a position to have an irritating experience in the first place, matters are liable to look very different indeed.” OB

“You don’t get to dictate the course of events. And the paradoxical reward for accepting reality’s constraints is that they no longer feel so constraining.” OB

“Really, no matter how far ahead you plan, you never get to relax in the certainty that everything’s going to go the way you’d like. Instead, the frontier of your uncertainty just gets pushed further and further toward the horizon.” OB

“A most surprisingly effective antidote to anxiety can be to simply realize that this demand for reassurance from the future is one that will definitely never be satisfied—no matter how much you plan or fret, or how much extra time you leave to get to the airport. You can’t know that things will turn out all right. The struggle for certainty is an intrinsically hopeless one.” OB

“Your days aren’t progressing toward a future state of perfectly invulnerable happiness, and that to approach them with such an assumption is systematically to drain our four thousand weeks of their value.” OB

Procrastination:
Success isn’t preventing everything from falling through the cracks, it’s knowing what to let fall through. “The real measure of any time management technique is whether or not it helps you neglect the right things.” OB

“The good procrastinator accepts the fact that she can’t get everything done, then decides as wisely as possible what tasks to focus on and what to neglect. By contrast, the bad procrastinator finds himself paralyzed precisely because he can’t bear the thought of confronting his limitations. For him, procrastination is a strategy of emotional avoidance—a way of trying not to feel the psychological distress that comes with acknowledging that he’s a finite human being.” OB

“Since every real-world choice about how to live entails the loss of countless alternative ways of living, there’s no reason to procrastinate, or to resist making commitments, in the anxious hope that you might somehow be able to avoid those losses. Loss is a given. That ship has sailed—and what a relief.” OB

When faced with a significant decision in life, ask “Does this choice diminish me, or enlarge me?” Comfortable often equals diminishing. Uncomfortable often equals growth.

Awareness:
“We cannot get anything out of life. There is no outside where we could take this thing to. There is no little pocket, situated outside of life, to which we could steal life’s provisions and squirrel them away. The life of this moment has no outside.” Jay Jennifer Matthews

Impatience:
People complain that they no longer have “time to read” but the reality is not that they don’t have time, but when they find time they’re too impatient to give themselves over to the task.

“In a world geared for hurry, the capacity to resist the urge to hurry—to allow things to take the time they take—is a way to gain purchase on the world, to do the work that counts, and to derive satisfaction from the doing itself, instead of deferring all your fulfillment to the future.” OB

Three principles of patience:

1. Develop a taste for having problems.

   “Yet the state of having no problems is obviously never going to arrive. And more to the point, you wouldn’t want it to, because a life devoid of all problems would contain nothing worth doing and would therefore be meaningless.” OB

   “I was peeling a red apple from the garden when I suddenly understood that life would only ever give me a series of wonderfully insoluble problems. With that though an ocean of profound peace entered my heart.” Christian Bobin

2. Embrace radical incrementalism
.
   Create small habits that you can sustain even on your worst days. Persistence is what matters, start small, show up every day.

3. Originality lies on the far side of unoriginality.
   
Arno Minkkinen, Finnish American photographer, power of patience parable: At Helsinki’s main bus station, there are two dozen platforms with several different bus lines. You pick a route, but it follows most of the other buses on its first few stops through the city. In your career, after a couple of years of following that route, you’re dismayed your work isn’t as original as you hoped so you go back to the bus station and pick a different route. Instead, Minkkinen says the solution is to “Stay on the fucking bus.” Because after the buses get through the first leg of their journey, their routes begin to diverge, plunging off to unique destinations as they head through the suburbs to the countryside. That’s where the original, distinct work begins. “But it begins at all for those who can muster the patience to immerse themselves in the earlier stage—the trial-and-error phase of copying others, learning new skills, and accumulating experience.” OB

The Art of the Good Life – Rolf Dobelli

The Art of the Good Life – Rolf Dobelli
Date read: 9/5/21. Recommendation: 8/10.

The book provides a toolkit with 52 guidelines for operating in a challenging modern world that we can struggle to understand intuitively. It’s a summary of lessons from modern psychology (Kahneman), Stoic philosophy, and value investing (Warren Buffett and Charlie Munger). If you enjoy those sources, you will enjoy this book. If you’re unfamiliar with those sources, Dobelli presents an approachable introduction that encourages further exploration. It’s a great overview of the powerful mental models and frameworks that some of the best minds use to navigate (and simplify) life.

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

My Notes:

Self-correction:
Education system oriented around factual knowledge and certifications, rather than the ability to reflect and self-correct. Degrees are nearing the point where they have less and less correlation to workplace success.

The wise man makes small adjustments: “What do you think: was it the set-up—the perfect genes, an ideal upbringing, a first-class education—that made this person so wise? Or was it acts of correction, of constant work on their own issues and shortcomings, a gradual elimination of these inadequacies from their lives?” RD

Flexibility is a trap:
Flexibility makes you unhappy, tired, and distracts you from your goals. There are two main traps: 1) Constantly having to make new decisions situation by situation saps willpower and leads to decision fatigue. 2) By being consistent on certain topics, signal where you stand and there’s no room for negotiation. Warren Buffett refuses on principle to negotiate. You get to make one offer.

Act while it’s uncomfortable:
“If you won’t attack a problem while it’s solvable and wait until it’s unfixable, you can argue that you’re so damn foolish that you deserve the problem.” Charlie Munger

Authenticity within reason:
“People are respected because they deliver on their promises, not because they let us eavesdrop on their inner monologs.” RD

“Restrict authenticity to keeping your promises and acting according to your principles. The rest is nobody else’s business.” RD

Prioritization + Focus:
Before ever responding to a request, wait five seconds. “If you say ‘No’ ninety percent of the time, you’re not missing much in the world.” Charlie Munger

Focusing illusion: “Nothing in life is as important as you think it is while you are thinking about it” Daniel Kahneman. The more narrowly we focus on a specific aspect of our lives, the greater its apparent influence. Step back, create some distance, and compare only once you pull yourself from the trenches.

Circle of competence: “Know your circle of competence, and stick within it. The size of that circle is not very important, knowing its boundaries, however, is vital.” Warren Buffett

Professional backgammon player makes a few deliberate mistakes to see how well his opponent will exploit them. If the other guy plays well, stop playing so you don’t throw away money. Knowing when you’re outside of your circle of competence and when not to bet is a critical life skill.

“A single outstanding skill trumps a thousand mediocre ones. Every hour invested in your circle of competence is worth a thousand spent elsewhere.” RD

Volunteer’s folly: “Many people fall for the volunteer’s folly—they believe there’s a point to voluntary work. In reality, it’s a waste. Your time is more meaningfully invested in your circle of competence, because it’s there that you’ll generate the most value per day.” RD

Purpose:
“One of the symptoms of approaching nervous breakdown is the belief that one’s work is terribly important.” Bertrand Russell

When you’re starting your career, focus on stacking skills first, purpose second.

Prevention:
“Wisdom is a practical ability. It’s a measure of the skill with which we navigate life. Once you’ve come to realize that virtually all difficulties are easier to avoid than to solve, the following definition will be self-evident: ‘Wisdom is prevention.’” RD

Consider your health, career, finances, relationships: “A clever person solves a problem. A wise person avoids it.” Einstein

Prevention of mistakes and massive do-overs requires the ability to anticipate second and third-order consequences. Project multiple steps down the line.

Do the work:
“You can know the name of a bird in all the languages of the world, but when you’re finished, you’ll know absolutely nothing whatever about the bird…So let’s look at the bird and see what it’s doing—that’s what counts. I learned very early the difference between knowing the name of something and knowing something.” Richard Feynman

Monetizing Innovation – Madhavan Ramanujam

Monetizing Innovation – Madhavan Ramanujam and Georg Tacke
Date read: 8/26/21. Recommendation: 7/10.

Reads like a series of case studies on the importance of monetization when you’re launching a new product or startup. However, it lacks some of the punch and the frameworks that a course like Reforge leverages to really drive its concepts home. To be fair, this is still a solid resource. Monetization strategy as it relates to building products is a subject that deserves more focus (and more books). The general principles of the book can be summed up as: assess willingness to pay early, segment customers based on willingness to pay, use that information to inform product configuration and bundling, and choose a pricing model that fits your business.

See my notes below or Amazon for details and reviews.

My Notes:

Willingness to pay:
“New products fail for many reasons. But the root of all innovation evil is the failure to put the customer’s willingness to pay for a new product at the very core of product design.” MR

The willingness to pay talk is critical to have early and will immediately tell you whether you have an opportunity to monetize your product and if it will help you prioritize features and design the product with the right set of features.

Asking about the value of your product:

• What do you think could be an acceptable price? Why?

• What do you think would be an expensive price? Why?

• What do you think would be a prohibitively expensive price? Why?

• Would you buy this product at $X? Why?

Other mechanisms for assessing value:

• Purchase probability questions (Scale of 1-5 how likely would you be to buy this product, how would you rate this product, etc.)

• Most-least questions (List six features and rank from most valuable to least valuable then run a MaxDiff).

Feature shocks:
When the product has too many “nice to haves” and too few “gotta haves.”

Rules for innovation + monetization success:

1. Have the willingness to pay talk with customers early

2. Build customer segments based on differences in their willingness to pay

3. Pay close attention to product configuration and bundling

4. Choose the right pricing and revenue models, how and how much is a critical decision that must match your product.

Segmentation:
Examples could be, 1) want price only (low cost), 2) want it now (fast delivery), 3) want product only (performance above other factors like service, shipping, price), 4) want the best (least price sensitive)

Monetization models:
Subscription (Netflix), dynamic pricing (airlines, Uber), market-based pricing (AdWords), pay as you go (CAT scan or jet engine).

Radical Candor – Kim Scott

Radical Candor – Kim Scott
Recommendation: 8/10. Date read: 8/12/21.

I’m late to the game when it comes to this book. Radical Candor has long been cemented in the business world and catches quite a bit of flack as a buzzword. But criticism, as Nassim Taleb suggests, is a far better indicator that a book is worth reading than silence. Scott’s core concept is that radical candor is the combination of caring personally and challenging directly. The best managers align themselves to this while avoiding ruinous empathy, manipulative insincerity, and obnoxious aggression. This is one of the best all-around resources for managers that I’ve read with insightful sections on responsibilities, how to run meetings, and growth management.

See my notes below or Amazon for details and reviews.

My Notes:

Empathy and the golden mean:
“Healthy emotional empathy makes for a more caring world. It can nurture social connection, concern, and insight. But unregulated emotional empathy can be the source of distress and burnout; it can also lead to withdrawal and moral apathy.” John Halifax

Responsibilities as a manager:
1) Create a culture of guidance (praise and criticism) that will keep everyone moving in the right direction.

2) Understand what motivates each person on your team well enough to avoid burnout or boredom and keep the team cohesive.

3) Drive results collaboratively.

Radical candor:
Radical candor = care personally + challenge directly

“Being responsible sometimes means pissing people off. You have to accept that sometimes people on your team will be mad at you.” KS

Growth management:
Steep growth trajectory: change agent, ambitious at work, want new opportunities, superstar

Gradual growth trajectory: force for stability, ambitious outside of work, happy in current role, rock star

You need both types on your team. Rockstars are better for roles that require steadiness and accumulated knowledge. Superstar might not have the focus or patience for the same type of project. Best way to keep superstars happy is challenge them and make sure they’re constantly learning. People often shift between growth trajectories at different phases of their life/careers.

“To be successful at growth management, you need to find out what motivates each person on your team. You also need to learn what each person’s longe term ambitions are, and understand how their current circumstances fit into motivations and their life goals.” KS

Don’t over-promote as the only way to reward your best people: “In World War II, the U.S. Air Force took their very best pilots from the front lines and sent them to train new pilots. Over time this strategy dramatically improved the quality and effectiveness of the U.S. Air Force. The Germans lost their air superiority because they flew all their aces until they were shot down; none of them trained new recruits. By 1944 new German pilots had clocked only about half of the three hundred hours an Allied pilot would have flown in training.” KS

Refinement:
“It is only by selection, by elimination, and by emphasis that we get at the real meaning of things.” Georgia O’Keeffe

“The essence of making an idea clear requires a deep understanding not only of the idea but also of the person to whom one is explaining the idea.” KS

You are the exception to the “criticize in private” rule of thumb:
Determine who on your team is comfortable criticizing you and ask them to do it in front of others at staff or all hands meetings. Will demonstrate you want the feedback. “The bigger the team, the more leverage you get out of reacting well to criticism in public.” KS

“Remind yourself going in that no matter how unfair the criticism, your first job is to listen with the intent to understand, not to defend yourself.” KS

Hiring:
“If you’re not dying to hire somebody, don’t make an offer. And, even if you are dying to hire somebody, allow yourself to be overruled by the other interviewers who feel strongly the person should not be hired. In general, a bias towards no is useful when hiring.” KS

Staff meetings:
-Learn: review key metrics (20 minutes)
-Listen: put updates in a shared document (15 minutes)
-Clarify: identify key decisions and debates (30 minutes)

Continuous Discovery Habits – Teresa Torres

Continuous Discovery Habits – Teresa Torres
Recommendation: 8/10. Date read: 8/3/21.

This should be a foundational book for product teams looking to introduce stronger discovery habits. Torres emphasizes the principle of outcomes over outputs as being at the heart of better discovery. She starts by walking through how to discover opportunities through visualization exercises, mapping, and continuous interviews. Then she digs into how to discover solutions through ideation and identifying hidden assumptions. It’s in this section that I think she presents her strongest idea and framework which is built around testing assumptions, not ideas. Along the way, Torres also presents anti-patterns that go against best discovery practices so you can identify which pitfalls to avoid.

See my notes below or Amazon for details and reviews.

My Notes:

Opportunity solution trees:
“Shifting from a project mindset to a continuous mindset is hard. We tend to take our six-month-long waterfall project, carve it up into a series of two weeks sprints, and call it ‘Agile.’ But this isn’t Agile. Nor is it continuous. A continuous mindset requires that we deliver value every sprint.” TT

Solving smaller opportunities eventually solves bigger opportunities. 

Instead of asking, “Should we solve this customer need?” Instead ask, “Which of these customer needs is most important for us to address right now?”

Assumptions:
Desirability: Does anyone want it?
Viability: Should we build it?
Feasibility: Can we build it?

Once you have all assumptions listed out, map them on a quadrant. X-axis goes from strong evidence on the left to weak evidence on the right. Y-axis goes from less important at the bottom to more important at the top. Any assumptions that land in the top right corner (weak evidence, more important) are leap of faith assumptions. This gives you an indicator of which assumptions should be tested first. 

Break a product or feature up into smaller opportunities. Each opportunity should then map to assumptions that you are testing. That way you’re learning with each opportunity you knock out. If you attempt to test the whole idea, rather than an individual assumption, there will be too much noise to determine what was actually effective or ineffective. 

“We aren’t testing one idea at a time. We are testing assumptions from a set of ideas.” TT

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

Freedom – Sebastian Junger

Freedom – by Sebastian Junger
Recommendation: 7/10. Date read: 6/25/21.

You can’t go wrong with any of Junger’s books. In Freedom he examines how the ideal of freedom manifests in our lives and throughout human history. As well as the tension it creates as we cling to the illusion of self-sufficiency in a modern world where it’s nearly impossible to achieve. Junger weaves his own story, contemplating these ideas while spending a year walking railroad lines in the Eastern United States, à la Thoreau in Walden. Worth the read, he’s one of the most powerfully succinct writers out there.

See my notes below or Amazon for details and reviews.

My Notes:

Self-sufficiency:
“If subsistence-level survival were the standard for absolute freedom, the word would mean nothing because virtually no one could pass that test. People love to believe they’re free, though, which is hard to achieve in a society that has outsourced virtually all of the tasks needed for survival. Few people grow their own food or build their own homes, and no one—literally no one—refines their own gasoline, performs their own surgery, makes their own ball bearings, grinds their own eyeglass lenses, or manufacturers their own electronics from scratch.” SJ

“Fit people obviously outperform unfit ones, but their minds are also better adapted to stress.” SJ

Detachment:
“Spanish horseman strapped into armor and backed by cannon might successfully siege a Pueblo town, but they couldn’t hope to run down small bands of Apache in the mountains. It was the very poverty of the Apache—nothing to defend and almost nothing to carry—that made them hard to subdue, and therefore free.” SJ

Sacrifice:
“In modern democracies, however, an ethos of public sacrifice is rarely needed because freedom and survival are more or less guaranteed. That is a great blessing but allows people to believe that any sacrifice at all—rationing water during a drought, for example—are forms of government tyranny.” SJ

“The idea that we can enjoy the benefits of society while owing nothing in return is literally infantile. Only children owe nothing.” SJ

“Like warfare, building a railroad is crushingly monotonous when it isn’t absolutely deadly.” SJ

Washington: A Life – Ron Chernow

Washington: A Life – by Ron Chernow
Recommendation: 9/10. Date read: 4/27/21.

The definitive biography of George Washington. Chernow tracks the entirety of Washington’s celebrated life from childhood to his early experiences in the French and Indian War, and eventually through his role as commander of the Continental Army and years serving as American’s first president. The depth of Washington’s life is awe-inspiring. At every turn, he demonstrated an ability to make difficult decisions by relying on his strong moral compass during turbulent times when outcomes were far from certain—especially through the American Revolution and the early years of a newly formed government. He was a deeply private figure, cloaking himself in mystery despite the fame that followed him in later life. Although reluctant to accept political roles he found his way into, he was purposeful in his every move—a true statesman who put the wellbeing of the nation over his desire for a quiet life.

See my notes below or Amazon for details and reviews.

My Notes:

Cloak yourself in mystery:
“An important element in Washington’s leadership both as a military commander and as President was his dignified, even forbidding, demeanor, his aloofness, the distance he consciously set and maintained between himself and nearly all the rest of the world.” W.W. Abbot

Washington often focused on learning the maximum about other people’s thoughts while revealing the minimum about his own.

“Let all men know thee, but no man know thee thoroughly.” Benjamin Franklin

Washington possessed the gift of silence and had great self-command. Exerted more power by withholding opinions than by expressing them. His public role led him to create a barrier that prevented intimacy with all but a few. This secrecy and evasion allowed him to avoid compromising his position and alerting the enemy to weaknesses during the American Revolution when he was (almost always) deficient of men, munitions, and supplies.

Character:
“With command of his tongue and temper, he had the supreme temperament for leadership compared to his scheming rivals. It was perhaps less his military skills than his character that eclipsed all competitors. Washington was dignified, circumspect, and upright, whereas his enemies seemed petty and skulking.” RC

At the end of the American Revolution, Washington resigned his position and return to privacy at Mount Vernon. “The figure hurrying back to his long-forgotten past had just accomplished something more extraordinary than any military feat during the war. At war’s end, he stood alone at the pinnacle of power, but he never became drunk with that influence, as had so many generals before him, and treated his commission as a public trust to be returned as soon as possible to the people’s representatives. Throughout history victorious generals had sought to parlay their fame into political power, whereas Washington had only a craving for privacy. Instead of glorying in his might, he feared its terrible weight and potential misuse.” RC

“He brought maturity, sobriety, judgment, and integrity to a political experiment that could easily have grown giddy with its own vaulted success, and he avoided the backbiting, envy, and intrigue that detracted from the achievements of other founders.” RC

Purposeful:
Young Washington was adventurous (swimming, riding, hunting, fencing) and combined this with an ability to master social etiquette, enabling him to climb the ladder of high society. “He was an unusually sober and purposeful young man.” RC

Moral compass:
“George Washington possessed the gift of inspired simplicity, a clarity and purity of vision that never failed him. Whatever petty partisan disputes swirled around him, he kept his eyes fixed on the transcendent goals that motivated his quest. As sensitive to criticism as any other man, he never allowed personal attacks or threats to distract him, following an inner compass that charted the way ahead.” RC

Decision making:
“Always fearful of failure, Washington wanted to push ahead only if he was armed with detailed knowledge and enjoyed a high likelihood of success. This cautious, disciplined political style would persist long after the original insecurity that had prompted it had disappeared.”

The French and Indian War:
Taught Washington invaluable lessons in frontier warfare which the Indians demonstrated so well—mobile style of warfare that relied on ambushing, sniping from trees, and vanishing into the forest. His defeat on the frontier came be seen as a doomed but heroic defense rather than a military blunder.

“Some men will gain as much experience in the course of three or four years as some will in ten or a dozen.” Washington


“It was this process of subtle, silent, unrelenting self-criticism that enabled him to rise above his earthly defeats.” RC

Must undergo a hard winter training to develop true confidence:

“As a member of the British forces, he had begun to articulate a comprehensive critique of British fighting methods in North America. For a young man, he acquired an amazing amount of experience and these precocious achievements yielded a lasting reservoir of self-confidence. He had proved his toughness and courage in the face of massacres and defeats. He had learned to train and drill regiments and developed a rudimentary sense of military strategy. He had shown a real capacity to lead and take responsibility for fulfilling the most arduous missions. Perhaps, most important, his experience in the French and Indian War made him a believer in strong central government and a vigorous executive. Forced to deal with destructive competition, among the colonies, dilatory legislative committees, and squabbling, shortsighted politicians, he had passed an excellent dress rehearsal for the prolonged ordeal of the American Revolution.” RC

Skin in the game:
Part of the reason that Washington commanded such a deep respect from everyone throughout his life and career is because he was always willing to put himself in the heat of battle. He never shied away from the front lines.

“Washington was no remote leader but an active, rousing presence.” RC

“To obtain the applause of deserving men is a heartfelt satisfaction; to merit them is my highest wish.” Joseph Addison

American Revolution:
Great Britain was bad for local business, which created the unique situation and historical anomaly of a revolution inaugurated by affluent, conservative leaders.

Early on Washington learned to shift his strategy and wage a defensive war in order to keep the cause alive. See retreat from Long Island on page 250. See calamities at Forts Washington and Lee on page 264 (futility of trying to defend positions along seaboard and moved instead into countryside where mobility favored Continental Army).

Crossing the Delaware, 1776: Washington was more concerned about patriotic support tapering off and short enlistments that would allow most of his army to depart at the end of the year than he was about the strength of the British Army. Washington knew without a momentous victory and a daring strike, it would be difficult to inject energy into the cause. Washington and the army crossed the river in treacherous conditions and descended on Trenton. The battle was over in an hour. After this victory and the next at Princeton, the psychology of the war was dramatically reversed. Page 269.

“His military triumphs had been neither frequent nor epic in scale. He had lost more battles than he had won…But he was a different kind of general fighting a different kind of war…His fortitude in keeping the impoverished Continental Army intact was a major historic accomplishment.” RC

“In defining the culture of the Continental Army, he had helped to mold the very character of the country, preventing the Revolution from taking a bloodthirsty, or despotic turn.” RC

Missionaries > Mercenaries:
“The unconquerable resolution of our citizens, the conscious rectitude of our cause, and a confident trust that we should not be forsaken by heaven.” Washington

Moderation:
When Washington was appointed General and Commander in Chief, he acted as the glue that helped bind the colonies together. Hailing from Virginia, he knew how to bridge the North and South. “Many southerners feared that New Englanders were a rash, obstinate people, prone to extremism, and worried that an army led by a New England general might someday turn despotic and conquer the South. The appointment of George Washington would soothe such fears and form a perfect political compromise between North and South.” RC

“He also provided a conservative counterweight to some of the more unruly impulses of the American Revolution, ensuring incremental progress and averting the bloody excesses associated with the French Revolution.” RC

Second-order thinking:
“His overriding goal was to contrast his own humane behavior with the predatory ways of the enemy.” RC

Washington preached fair treatment of civilians, respect for private property, and doled out harsh punishment for anyone who violated this. “The spirit and willingness of the people must in a great measure take the place of coercion.” Washington

Presidency:
Not every decision you face will be a ‘hell yes.’ Washington was extremely reluctant to leave a sense of privacy and peacefulness at Mount Vernon to take on the challenges facing the country. He had serious doubts. The way he rationalized it was that he felt he could serve a couple of years then bow out before he even finished his first term. If he knew he would have served 8 years, he likely wouldn’t have agreed to it.

“The presidency is the powerful office it is in large part because of Washington’s initial behavior. Washington had forged the executive branch of the federal government, appointed outstanding department heads, and set a benchmark for fairness, efficiency, and integrity that future administrations would aspire to match.” RC

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.”

How to Think Like a Roman Emperor – Donald Robertson

How to Think Like a Roman Emperor – by Donald Robertson
Recommendation: 8/10. Date read: 3/15/21.

A unique approach that ties together stories from Roman emperor Marcus Aurelius’s life with Stoic philosophy and modern psychology. As Robertson walks through the chapters alongside Marcus, it’s clear what a rare leader he was with Stocisim as his anchor. To lead, you must care about something bigger than yourself. As Marcus knew, no number of bodyguards could be enough to shield a ruler who does not possess the goodwill of his subjects. There are great chapters on building self-awareness, navigating difficult decisions, and finding strength in kindness.

See my notes below or Amazon for details and reviews.

My Notes:

To lead, you must care about something bigger than yourself:
No number of bodyguards is enough to shield a ruler who does not possess the goodwill of his subjects. 

Rhetoric vs. Philosophy:
Epictetus on the difference between a Sophist and a Stoic: “the former speaks to win praise from his audience, the latter to improve them by helping them to achieve wisdom and virtue. Rhetoricians thrive on praise which is vanity; philosophers love truth and embrace humility. Rhetoric is a form of entertainment, pleasant to hear, philosophy is a moral and psychological therapy, often painful to hear because it forces us to admit our own faults in order to remedy them.” DR

External advantages:
“Those who squander their sudden wealth end up more miserable than they could have imagined. When handled badly, eternal advantages like wealth do more harm than good.” DR

Strength in kindness:
Marcus Aurelius believed true strength consisted of one’s ability to show kindness, not violence or aggression. During his reign, he pledged that not a single senator would be executed. He kept this promise even when he was betrayed by several during a civil war in the east.

Decision making:
Do not let ambiguity linger for too long…Once Marcus came to a decision, he implemented it with unwavering determination. See Ernest Shackleton for a similar example in moments of crisis. 

Marcus was also meticulous in examining matters that required careful deliberation (decisions that were not easily reversible). He would challenge his first impression and patiently consider the issue. 

Marcus was never taken in by charlatans nor did he engage or attack them. He simply ignored those who were a drain on his time and energy. 

Decatastrophizing:
“Involves reevaluating the probability and severity of something bad happening and framing it in more realistic terms.” Instead of “What if?” shift to thinking “So what?” 

Upsetting experiences aren’t timeless. Everything has a before, during, and after phase.

Self-awareness:
“Those who assume they have the fewest flaws are often the ones most deeply flawed in the eyes of others.” DR

The obstacle is the way:
“What do you think Hercules would have amounted to if there had not been monsters such as the Nemean lion, the Hydra, the stag of Artemis, the Erymanthian boar, and all those unjust and bestial men for him to contend with? Why, if he had sat at home, wrapped up asleep in bedsheets, living in luxury and ease, he would have been no Hercules at all!” Epictetus

Joy:
“The Stoics tended to view joy not as the goal of life, which is wisdom, but as a by-product of it, so they believed that trying to pursue it directly might lead us down the wrong path sought at the expense of wisdom.” DR

Expectations
Reverse clause = undertaking action while calmly accepting that the outcomes aren’t entirely within your control. Expectations are reserved for what’s within your sphere of control.

“Virtue consists in doing your very best and yet not becoming upset if you come home from the hunt empty-handed.” DR

The Courage to Be Disliked – Ichiro Kishimi and Fumitake Koga

The Courage to Be Disliked – by Ichiro Kishimi and Fumitake Koga
Recommendation: 10/10. Date read: 2/23/21.

This is the best book I’ve read in months. The Courage to Be Disliked follows a dialogue between a philosopher and a young man who debate whether or not happiness is something you choose for yourself. The philosopher examines happiness from the theories and frameworks of Alfred Adler and Adlerian psychology. It’s a refreshing perspective that empowers you to escape determinism and avoid allowing yourself to be defined by past traumas or the weight of external expectations. As Kishimi emphasizes, “Your life is not something that someone gives you, but something you choose for yourself, and you are the one who decides how you live.” The Courage to Be Disliked is a wonderful resource to improve your relationships, find your courage, and pursue personal growth.

See my notes below or Amazon for details and reviews.

My Notes:

Determinism:
“If we focus only on past causes and try to explain things solely through cause and effect, we end up with ‘determinism.’ Because what this says is that our present and our future have already been decided by past occurrences, and are unalterable.” IK

Shift perspective from past causes to present goals to better understand the situation. Instead of “your friend is insecure so they won’t go out,” consider that “he doesn’t want to go out so he’s creating a state of anxiety.” 

Etiology: the study of causation champion by Freud and Jung.
Teleology: the study of the purpose of a given phenomenon, rather than its cause. 

“The important thing is not what one is born with but what use one makes of that equipment.” Adler

Trauma:
“No experience is in itself a cause of our success or failure. We do not suffer from the shock of our experiences—the so-called trauma—but instead we make out of them whatever suits our purposes. We are not determined by our experiences, but the meaning we give them is self-determining.” Adler

“Your life is not something that someone gives you, but something you choose for yourself, and you are the one who decides how you live.” IK

“An experience of hardship should be an opportunity to look ahead and think, What can I do from now on?” IK

Influence:
“Why are you rushing for answers? You should arrive at answers on your own, not rely upon what you get from someone else.” IK

Change:
“People can change at any time, regardless of the environments they are in. You are unable to change only because you are making the decision not to.” IK

Complacency: People might have complaints but it’s often easier and more secure to leave it the way it is. People become comfortable with being miserable.

Courage:
“When we try to change our lifestyles, we put our great courage to the test. There is the anxiety generated by changing, and the disappointment attendant to not changing.” IK

“Adlerian psychology is a psychology of courage. Your unhappiness cannot be blamed on your past or your environment. And it isn’t that you lack competence. You just lack courage. One might say you are lacking in the courage to be happy.” IK

“Freedom is being disliked by other people…It is proof that you are exercising your freedom and living in freedom, and a sign that you are living in accordance with your own principles.” IK

“But conducting oneself in such a way as to not be disliked by anyone is an extremely unfree way of living, and is also impossible. There is a cost incurred when one wants to exercise one’s freedom. And the cost of freedom in interpersonal relationships is that one is disliked by other people.” IK

“The courage to be happy also includes the courage to be disliked.” IK

“For a human being, the greatest unhappiness is not being able to like oneself.” IK

Relationships:
It’s basically impossible not to get hurt in relationships…you will get hurt and you will hurt someone. “To get rid of one’s problems, all one can do is live in the universe all alone.” Adler

You don’t need to change everyone’s mind and not everyone needs to think identically to you. When you’re hung up on winning and losing, you lose the ability to make rational decisions and clouds your judgment as you’re preoccupied with immediate victory or defeat. It completely breaks your ability to assess long-term strategy. 

“The moment one is convinced that ‘I am right’ in an interpersonal relationship, one has already stepped into a power struggle.” IK

Self-sufficiency:
Two objectives in Adlerian psychology are laid out for human behavior: to be self-reliant and to live in harmony with society. Two objectives for psychology that support these behaviors are the consciousness that I have the ability and that people are my comrades.

“You are not living to satisfy other people’s expectations.” IK

“If you are not living your life for yourself, who could there be to live it instead of you?” IK

Recognition can’t be your motivation: “Wishing so hard to be recognized will lead to a life of following expectations held by other people who want you to be ‘this kind of person.’” IK

Inferiority and superiority:
“The pursuit of superiority and the feeling of inferiority are not diseases but stimulants to normal, health striving and growth.” IK

How to compensate for the part that is lacking: “The healthiest way is to try to compensate through striving and growth. For instance, it could be applying oneself to one’s studies, engaging in constant training, or being diligent in one’s work. However, people who aren’t equipped with that courage end up stepping into an inferiority complex. Again, it’s thinking, I’m not well educated, so I can’t succeed. “ IK

Healthy feeling of inferiority doesn’t come from comparing yourself to others, but from comparing yourself to your ideal self. Competition often only blinds you to your ideal self. You get pulled into races that you’re not willing to run. 

Ego: “Those who go so far as to boast about things out loud actually have no confidence in themselves. As Adler clearly indicates, ‘The one who boasts does so only out of a feeling of inferiority.’” IK

Confidence: True confidence in yourself means there is no need to boast. 

Separating tasks:
All relationship troubles stem from intruding on other people’s tasks or having your own tasks intruded on. Consider ‘whose task is this’ and continuously work to separate your own from other people’s. Similar to the Stoic task of separating internals from externals. 

Intervening in other people’s tasks and taking on other people’s tasks adds complexity, heaviness, hardship, and drama. If you want to optimize for simplicity, discard other people’s tasks and focus on your own. 

Example 1: Studying is the child’s task. A parent commanding their child to do homework is intruding on the child’s task. The parent can only lead the child to their own decision or else they’ll only be successful to a degree because they can’t force this behavior.

Example 2: Not approving is your parents’ task, not yours. It’s not a problem for you to worry about. What another person thinks of you is their task, not yours. You have no control over this. 

Horizontal relationships:
The standpoint of Adlerian psychology is that you should not praise or rebuke another person because both represent an act of judgment. The desire to be praised or give praise is indicative of vertical relationships.

“Instead of commanding from above that the child must study, one acts on him in such a way that he can gain the confidence to take care of his own studies and face his tasks on his own.” IK

Alex: Similar to relationships with managers in the workplace. To treat these are vertical assumes this person is all-knowing. In reality, they’re still learning and growing and you have a unique experience that might provide a better vantage point on a certain problem. 

In horizontal relationships rather than praising or rebuking (as indicated in vertical relationships), express gratitude—thank you, that was a big help, I’m glad. 

Meaning:
“Whatever meaning life has must be assigned to it by the individual.” Adler

How I Invest My Money – Joshua Brown and Brian Portnoy

How I Invest My Money – by Joshua Brown and Brian Portnoy
Recommendation: 8/10. Date read: 2/11/21.

Instead of financial gurus preaching what you should do with your money, this book is a collection of essays by 25 financial experts detailing how they invest, save, spend, give, and borrow in their own lives. Through reflection and personal stories, each expert breathes life into the how and why of their investments. Each investment strategy is quite different which illustrates a key point of the book, there’s no single “right” way. What matters most is that you’re thoughtful and true to yourself in your approach.

See my notes below or Amazon for details and reviews.

My Notes:

Independence:
“I did not intend to get rich. I just wanted to get independent.” Charlie Munger 

“I mostly just want to wake up every day knowing my family and I can do whatever we want on our own terms. Every financial decision we make revolves around that goal.” Morgan Housel

“Independence, to me, doesn’t mean you’ll stop working. It means you only do the work you like with people you like at the time you want for as long as you want.” Morgan Housel

Get the goal post to stop moving: “Independence, at any income level, is driven by your savings rate. And past a certain level of income your savings rate is driven by your ability to keep your lifestyle expectations from running away.” Morgan Housel

Define what is enough: simplify by finding the line between excess and satisfaction. 

Investing strategy:
High savings + patience: “My investing strategy doesn’t rely on picking the right sector, or timing the next recession. It relies on a high savings rate, patience, and optimism that the global economy will create value over the next several decades.” Morgan Housel

Get the big stuff right: “Getting the big stuff right—living within their means, setting a reasonable savings rate, staying employed—will be a bigger determinant of whether they reach their goals than will their investment selections.” Christine Benz

Invest in yourself: “Invest in yourself. Your ability to work is your safest and highest returning asset. By lifelong learning, and taking care of your physical health, mental health, and relationships, you are much more likely to lead a secure and satisfying life without regrets.” Carolyn McClanahan

You biggest asset is your earning power: “I’m about 40, and plan on working for another 20 years. So, my biggest asset is still my earning power—my ability to turn my time and effort into money.” Dan Egan

Working matters more than investments: “I wonder if the greatest trick the devil ever played on investors is making them think it is the investing part that matters most. The working part moves the needle more, both for the math of deposits but also in the discipline of a purpose.” Ryan Krueger

Maximize for choice: “Having options and a little bit of luck are the key to financial security.” Debbie Freeman

Avoid the herd: “The more intensely and emotionally a lot of people ‘hate on’ a particular investment, that is a good signal to buy.” Joshua Rogers 

Move with purpose:
“You have exactly one life in which to do everything you will ever do. Act accordingly.” Colin Wright

Karma:
“Karma may be important in achieving wealth accumulation, but karma is definitely important in wealth preservation.” Joshua Rogers 

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 Great Mental Models, Volume Two – Shane Parrish

The Great Mental Models, Volume Two – by Shane Parrish (Farnam Street)
Recommendation: 9/10. Date read: 1/18/21.

The Great Mental Models series by Farnam Street blows me away. The second book in this series focuses on the hard sciences including chemistry, biology, and physics. They do a tremendous job articulating the laws and models in a way that makes sense for those without a Ph.D. And rather than simply stating the law and sticking with the abstract, they translate how it applies to situations in your everyday life. They explain how laws of reciprocity translate to relationships, the ways in which inertia requires us to overcome the allure of what’s easy, and how an ecosystem translates to the most effective, creative, and collaborative working cultures.

See my notes below or Amazon for details and reviews.

My Notes:

Relativity:
“The limits of perspective are fundamental to how the world works. Considering multiple perspectives is the best chance we have to understand what is really going on.”

“What matters is understanding the complexity and value of multiple perspectives. No one sees it all. Multiple perspectives layered together reduce blind spots and offer us a more textured and truer sense of the underlying reality.” 

Reciprocity:
Life is an iterative and compounding game…it pays to go positive and go first.

“The more people you help, the more people you will have willing to help you.”

“If you want people to be thoughtful and kind, be thoughtful and kind. If you want people to listen to you, listen to them. The best way to achieve success is to deserve success.”

Thermodynamics:
First law of thermodynamics: energy cannot be created or destroyed. It can only be transferred or changed from one form to another. Consider how this applies in death. 

“Entropy reminds us that energy is required to maintain order. You need to anticipate things falling apart and focus on prevention.”

Exposure: “Mixing cultures gives them common ground. We move toward social equilibrium when we share ideas and values that have the same foundations.”

“Art is born out of as well as encapsulates the continuing battle between order and chaos. It seeks order or form, even when portraying anarchy.” John Yorke

Storytelling: “Every act of perception is an attempt to impose order, to make sense of a chaotic universe.”

Inertia:
“We stay at jobs we hate, avoid meaningful conversations with people of different opinions, and almost never change the religion our parents imposed on us at birth. All because it is easier to stay on our current path, however stagnant and unfulfilling it might be.”

Amount of effort required to change a habit is greater proportional to the length of time we’ve had it. This applies to both good habits and bad habits. Once you’ve established decades of good habits, it compounds and becomes difficult to stop your own success. The same applies in the opposite direction. 

Velocity:
Direction > speed

“If a man does not know to what port he is steering, no wind is favorable to him.” Seneca

Alloying:
Stacking skills is a force multiplier: “Alloying is about increasing strength through the combination of elements.”

Evolution:
“On the human timescale, adaptability is about recognizing when the way you have done things in the past is becoming less and less successful in a changing environment.” 

What got you here won’t keep you here or allow you to get to the next level. Personal growth is a lifelong effort and requires taking new risks: “You can’t stop adapting, because no one around you is stopping…Staying the same as we are often means falling behind.” 

“Success is measured by persistence.” Geerat Vermeij

Experimentation for its own sake matters: “We must not forget that when radium was discovered no one knew that it would prove useful in hospitals. The work was one of pure science. And this is proof that scientific work must not be considered from the point of view of the direct usefulness of it. It must be done for itself, for the beauty of science, and then there is always the chance that a scientific discovery may become like the radium a benefit for humanity.” Marie Curie

Antifragile: “Complacency will kill you. However, it’s not strength that survives, but adaptability. Strength becomes rigidity…Real success comes from being flexible enough to change, to let go of what worked in the past, and to focus on what you need to thrive in the future.”

Ecosystem:
Culture = the key to perseverance. Bill Walsh leading the 49ers: “Walsh recognized that a football organization’s culture is ultimately the system that will determine if a team can sustain the effort needed to win a championship.” Walsh believed, “everyone has a role, and every role is essential.” But they all had to be pointing in the same direction.

“The stronger and more resilient a system, the easier it can adapt and bounce back.” For Walsh it wasn’t about superstars or certain formations, “It was about building a culture that could be flexible in effectively responding to ever-changing environmental pressure.”

Self-preservation:
“Freeze mode usually takes over when the accumulation of stressors is so great that we can no longer really function.” 

Man’s search for meaning: “For humans, survival is not merely a binary like dead/alive. We don’t want to just continue breathing, but to have a life that we perceive as having meaning, value, or at least a point.”

Replication:
Commander’s intent: “Sharing the information necessary to empower subordinate commanders on the scene.” Too rigid and the person doing the work can’t adapt and innovate to execute against the strategy when circumstances change. Encourages troops to consider the why behind an order and the underlying strategy. 

Four elements of commander’s intent: formulate, communicate, interpret, and implement. The first two are the responsibilities of the senior commander. The second two are the responsibilities of the subordinate commander. 

Commander’s must consider four criteria:

1. Explain the rationale (the why): vision + strategy

2. Establish operational limits: constraints

3. Get feedback often: listen and learn

4. Recognize individual differences: leverage individual strengths

Incentives:
“Never, ever, think about something else when you should be thinking about the power of incentives.” Charlie Munger

“An incentive is a bullet, a key: an often-tiny object with astonishing power to change a situation.” Stephen D. Levitt

Least effort principle:
“Change is costly for most organisms. It can be easier to keep doing whatever has guaranteed their survival so far than to try something new that might fail and waste energy or endanger them. The instinct to minimize energy output can lead us to be resistant to change or risk-taking. “

Default thinking tendencies (aka heuristics): “Using this model as a lens helps us better understand our default thinking tendencies, and how our patterns of movement impact our physical environments.” 

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

Greenlights – Matthew McConaughey

Greenlights – by Matthew McConaughey
Recommendation: 8/10. Date read: 12/29/20.

Surprising in all of the best ways. McConaughey details his upbringing and career in a book that’s equal parts memoir and personal philosophy. It’s entertaining, funny, and thoughtful. He has chapters that detail the mindset required to overcome obstacles, the importance of appreciating and respecting your winters (when you feel alone and the going gets tough), as well as identity and the process of elimination. Well worth the read and some great quotes along the way.

See my notes below or Amazon for details and reviews.

My Notes:

Catching greenlights:
“Catching greenlights is about skill: intent, context, consideration, endurance, anticipation, resilience, speed, and discipline.” MM

The obstacle is the way: 
“It’s a matter of how we see the challenge in front of us and how we engage with it. Persist, pivot, or concede. It’s up to us, our choice every time.” MM

“It’s not about win or lose, it is about do you accept the challenge.”

Intentions are the real substance:
“Words are momentary. Intent is momentous.” MM

Outlaw logic:
McConaughey’s mom: “She’s always believed that if you understand something, then you own it, you can sign your name to it, take credit for it, live by it, sell it, and win medals for it. Plagiarism? ‘Shit, they’ll probably never find out and if they do all they can do is blame you and take your medal back, so fuck em,’ she says.” 

“Don’t invent drama. It will come on its own.” MM

Identity and the process of elimination:
“The first step that leads to our identity in life is usually not I know who I am, but rather I know who I’m not. Process of elimination.” MM

“Knowing who we are is hard. Eliminate who we’re not first, and we’ll find ourselves where we need to be.” MM

“Too many options can make a tyrant out of any of us, so we should get rid of the excess in our lives…” MM

On his decision to change direction in college and instead of going to law school pursue acting: “I didn’t want to miss my twenties preparing for the rest of my life.” MM

Respect your winters:
Seasons of suffering and loneliness can become the most important sacrifices in your life if you learn from them and look within. They can be the catalyst that forces you to find yourself. 

“As the noise decreases, the signals become clearer. We can hear ourselves again, and we reunite. Time alone simplifies the heart.” MM

“Sometimes we have to leave what we know to find out what we know.” MM

“Wherever you are, give the place the justice it deserves.” MM

Ego vs being present:
“The sooner we become less impressed with our life, our accomplishments, our career, our relationships, the prospects in front of us—the sooner we become less impressed and more involved with these things—the sooner we get better at them.” MM

“We are all made for every moment we encounter.” MM

“We must be aware of what we attract in life because it is no accident or coincidence…Our souls are infinitely magnetic.” MM