I’ve read some 170+ books since I started tracking my reading with Goodreads. Since 2018, I’ve run annual Twitter threads where I’ve captured lessons from each book I’ve completed. Here’s the complete breakdown of books I’ve read over the years and any lessons I’ve documented — since I drop books that I don’t find particularly compelling, you can look at this page as an endorsement of the set.
2014:
Steve Jobs
Live and Let Die
American Gods
Red Plenty
My Seinfeld Year
Fly My Tears, the Policeman Said
Creativity, Inc.
Fahrenheit 451
Zero to One
2015:
The Business of Venture Capital: Insights from Leading Practitioners on the Art of Raising a Fund, Deal Structuring, Value Creation, and Exit Strategies
Throne of the Crescent Moon
The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers
2016:
The Inevitable: Understanding the 12 Technological Forces That Will Shape Our Future
Thinking, Fast and Slow
Hillbilly Elegy: A Memoir of a Family and Culture in Crisis
The Fractured Republic: Renewing America's Social Contract in the Age of Individualism
Sapiens: A Brief History of Humankind
Between the World and Me
Superforecasting: The Art and Science of Prediction
Losing the Signal: The Untold Story Behind the Extraordinary Rise and Spectacular Fall of BlackBerry
The Everything Store: Jeff Bezos and the Age of Amazon
Capital in the Twenty-First Century
Specialization and Trade: A Re-introduction to Economics
High Output Management
Blockchain Revolution: How the Technology Behind Bitcoin Is Changing Money, Business, and the World
2017:
Guns, Germs, and Steel: The Fates of Human Societies
Strangers in Their Own Land: Anger and Mourning on the American Right
The End of Alchemy: Money, Banking, and the Future of the Global Economy
When the Tea Party Came to Town: Inside the U.S. House of Representatives' Most Combative, Dysfunctional, and Infuriating Term in Modern History
The Origins of Political Order: From Prehuman Times to the French Revolution
Technological Revolutions and Financial Capital: The Dynamics of Bubbles and Golden Ages
Misbehaving: The Making of Behavioral Economics
Why Nations Fail: The Origins of Power, Prosperity, and Poverty
Homo Deus: A History of Tomorrow
How Not to Be Wrong: The Power of Mathematical Thinking
The Fire Next Time
Dealing with China: An Insider Unmasks the New Economic Superpower
Team of Rivals: The Political Genius of Abraham Lincoln
Alibaba: The House That Jack Ma Built
The New Geography of Jobs
Shoe Dog: A Memoir by the Creator of NIKE
The Righteous Mind: Why Good People Are Divided by Politics and Religion
Titan: The Life of John D. Rockefeller, Sr.
The First Muslim: The Story of Muhammad
The Rational Optimist: How Prosperity Evolves
Antifragile: Things That Gain from Disorder
The Complacent Class: The Self-Defeating Quest for the American Dream
The Signal and the Noise: Why So Many Predictions Fail - But Some Don't
More Money Than God: Hedge Funds and the Making of a New Elite
The Upstarts: How Uber, Airbnb, and the Killer Companies of the New Silicon Valley Are Changing the World
Scarcity: Why Having Too Little Means So Much
All Marketers Are Liars: The Power of Telling Authentic Stories in a Low-Trust World
Behave: The Biology of Humans at Our Best and Worst
Tempo: Timing, Tactics and Strategy in Narrative-Driven Decision-Making
The New Jim Crow: Mass Incarceration in the Age of Colorblindness
Nonzero: The Logic of Human Destiny
The Snowball: Warren Buffett and the Business of Life
Hit Refresh
The Intelligent Investor
Sourdough
The Closing of the American Mind
Irresistible: The Rise of Addictive Technology and the Business of Keeping Us Hooked
A Crack in Creation: Gene Editing and the Unthinkable Power to Control Evolution
Hit Makers: The Science of Popularity in an Age of Distraction
The Lessons of History
Alexander Hamilton
Meditations
How Google Works
Principles
2018:
Blitzed: Drugs in the Third Reich
think through the second- and third-order effects that might result from a short-term fix
Flash Boys: A Wall Street Revolt
Technical insights come from deep understanding of the rules you're playing by.
Often, your customers are so used to the status quo that you need to inform them of their problem before you can sell them the solution.
How to Read a Book: The Classic Guide to Intelligent Reading
There are four questions you should ask of the books you read: What is the book about as a whole? What is being said, and how? Is it true? What of it?
Manufacturing Consent: The Political Economy of the Mass Media
For structural reasons (corp structure + ownership, advertising business models, sourcing issues), mainstream press in the US has longed served a propaganda function for elite interests that constrains critical analysis of gov and other power
The Varieties of Religious Experience
People stand by the gods they need; those whose demands of them enforce the demands they place on themselves.
The Globalization Paradox: Democracy and the Future of the World Economy
The tension between globalization, nation-states, and democracy will generate some of the most important domestic and international conflicts in the 21st century
Rational Ritual: Culture, Coordination, And Common Knowledge
Many coordination problems can be solved by generating common knowledge; some kinds of products are “social goods” which gain network effects via common knowledge of how/when they are used.
The Three-Body Problem
Don’t underestimate the potential impact of new knowledge as a symbol. New discoveries have second- and third-order effects beyond their direct applications.
Making Movies
When building something with many intertwining technical dependencies that need to form a cohesive whole, there’s a balance to strike between trusting technical leads while guiding the trade-offs they make
Scale: The Universal Laws of Growth, Innovation, Sustainability, and the Pace of Lifein Organisms, Cities, Economies, and Companies
The potential scale of a complex adaptive system (organism, city, company) is determined by the efficacy/efficiency of the networks it is composed of at moving around energy, information, and physical resources
Influence: The Psychology of Persuasion
The brain has a set of automatic responses that can be triggered to shape our decision-making. Monitoring the factors you’re basing decisions off of and the emotions you’re feeling can mitigate their effect.
The Brothers Karamazov
Suffering can lead to growth and redemption. But we shouldn’t take that to mean we should let or make people suffer - the escape from those circumstances is what allows for improvement.
Subliminal: How Your Unconscious Mind Rules Your Behavior
Our brains are wired to more readily accept new information that confirms our existing beliefs/vested interests than that which goes against them. To improve understanding/decision-making, actively try to invert this
Finite and Infinite Games: A Vision of Life as Play and Possibility
The mindset required to win a game where the end goal is a title and the power that comes with it is different from that needed for games where the goal is to simply continue playing
Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers
Building a product for the mainstream market requires adopting the mindset of the customer and thinking about how you can deliver the whole product - your offering + the other products/services needed to deliver on your promises
The Myth of the Rational Market: Wall Street's Impossible Quest for Predictable Markets
What looks like disruptive innovation is often the latest manifestation of a decades-old theory, mindset, or vision in particularly propitious circumstances
To Sell Is Human: The Surprising Truth About Moving Others
When you experience a setback, ask yourself: Are the new circumstances permanent? Will you always run into the reasons for the setback in your current effort? Did the setback happen because of personal failings, or the external situation?
The Power of Habit: Why We Do What We Do in Life and Business
Small wins fuel transformative changes by demonstrating patterns that convince us bigger achievements are within reach.
Charlie Munger: The Complete Investor
You can mitigate errors in your decision making by building a latticework of mental models about how the world works and cultivating a habit of looking for signs of bias in your own thinking.
The Book on the Taboo Against Knowing Who You Are
Distinction is not separation. To understand something, you must also understand its relationships with other parts of the environment or context around it.
Product Leadership: How Top Product Managers Launch Awesome Products and Build Successful Teams
A product leader succeeds by bringing together a team motivated to build and learn and regularly communicating a shared product vision aimed at providing value to a customer.
The Creators: A History of Heroes of the Imagination
Even the creative geniuses whose work transcends their time were extending, remixing, or responding to the techniques and themes prevalent in the context around them.
The Little Book of Common Sense Investing: The Only Way to Guarantee Your Fair Share of Stock Market Returns
Once you account for the difficulty of predicting future securities prices, transaction costs, other intermediary fees, and taxes, a low-cost, all-market index fund looks like a pretty good place for most to invest for the long term.
Investing: The Last Liberal Art
To build good mental models of how the world works, we need a general awareness of the fundamentals of various disciplines + the ability to think metaphorically
The Artist's Way
"Real artists/creators/entrepreneurs" don't go through life without experiencing self-doubt. They've simply learned to live with the doubt and do the work anyway.
The 48 Laws of Power
Power comes from directing the flow of information, patience, willpower, and a strong theory of mind.
Measure What Matters
To achieve high performance as an individual, you need to set goals beyond what you’ve accomplished in the past. To achieve high performance as an organization, you need to align contributors in the same direction.
The Hero with a Thousand Faces
Embedded in human psychology (and the resulting symbolism we find compelling) is a wish for our struggles to be meaningful, for our suffering to have value, for our effort to pay off for ourselves and those we love - and to then be recognized for it.
Clockspeed: Winning Industry Control In The Age Of Temporary Advantage
The only lasting competency is the ability to continuously assess industry/tech dynamics and build capability chains that exploit current opportunities and anticipate future ones.
Squeezed: Why Our Families Can't Afford America
We've got a few high-ROI tools for confronting inequality: Provide low income individuals and families the tools they need to make better decisions and plan for the future. Shift norms toward life-long learning. Value and invest in care work.
The Power
Power exists in the moment it's exercised. Its use shapes the wielder and the power itself.
Seeing Like a State: How Certain Schemes to Improve the Human Condition Have Failed
Modernist states try to simplify their environments to allow for measurement, management, and appropriation, to the detriment of the emergent, adaptive, practical, and local. Informal improvisation is required to sustain formal systems.
George Lucas: A Life
The world won’t judge you by the bar you set for yourself.
The Dictator's Handbook: Why Bad Behavior is Almost Always Good Politics
Autocratic leaders want to minimize the size of the coalition that can keep them in power and maximize the private rewards allocated to that coalition.
The Quest: Energy, Security, and the Remaking of the Modern World
The best ideas come under pressure. Accidents precede strategies.
Physical Control of the Mind: Toward a Psychocivilized Society
People will opt-in to brain-computer interfaces because they will give us explicit control over our own motivations, willpower, and mood.
Never Leave Well Enough Alone
In consumer psychology, there is a tension between the attraction to the new and the fear of the unfamiliar. Attempting to innovate while hitting expectations is inherently risky.
A World Lit Only by Fire: The Medieval Mind and the Renaissance: Portrait of an Age
The 20th century isn’t a big enough sample set to draw from to understand the range of societal responses to radical change. Things can get much, MUCH worse.
Old Man's War
Our lives get meaning from caring for others and having other people care about us.
Thinking in Systems: A Primer
Designing your startup as a system, you want external-facing systems to exhibit positive reinforcing feedback loops and internal-facing systems to drift to high performance.
Democracy in America
It’s only in the birth of societies/companies that we can easily follow principles to their conclusions and ignore the conflicting interests around us; this is not because of wisdom, but youth.
Wonder Boys
We can get trapped in the narratives we imagine around us. Reality is not a structured plot.
Strategic Intuition: The Creative Spark in Human Achievement
The most important question you can ask to solve a problem: "Has anyone ever made any progress solving any pieces of this puzzle?"
Kill Chain: Drones and The Rise of the High-Tech Assassins
Our illusions come from accepting abstractions as reality. They drive us toward disaster when processes become ends in themselves.
Lake Success
People can’t start over, lives go on. Resentment comes from people not living up to the abstraction of them that we hold in our mind.
The Ascent of Money: A Financial History of the World
As a system operates for an extended period without crisis, it becomes harder to imagine a crisis occurring and the more traumatic a crisis will seem for a given level of severity.
2019:
A Consumers' Republic: The Politics of Mass Consumption in Postwar America
The collective action in the 20th century toward consumerist reforms led to a political economy so oriented around convenience/value that it inhibits further collective action.
Procedural Content Generation in Games
When generative systems can automatically create high-fidelity art, human creativity can move up a level of abstraction to adding and removing constraints from a system and curating output.
The Courage to Be Disliked: The Japanese Phenomenon That Shows You How to Change Your Life and Achieve Real HappinesS
You don’t have to hold on to the trauma in your past.
Why We Sleep: Unlocking the Power of Sleep and Dreams
We seriously interfere with the development and mental health of teenagers with early school start times.
The Diamond Age: Or, A Young Lady's Illustrated Primer
Conformity and rebellion are paths for those who struggle to cope with contradiction and ambiguity. Changing a system from the inside requires subversiveness.
The Analects
Copy the good you see in others. When you recognize their faults, correct them in yourself.
7 Powers: The Foundations of Business Strategy
Market power comes from advantages that let you charge higher prices or operate at lower costs while simultaneously preventing competitors from arbitraging away those benefits.
Man and Technics: A Contribution to a Philosophy of Life
All great discoveries and inventions are expressions of personality by strong minds, not of the utilitarian thinking of the masses.
The Odyssey
Survival requires clever adaptation to the circumstances you face. Usually that means external challenges - but the true test is overcoming your own failings
Taxing Wars: The American Way of War Finance and the Decline of Democracy
Eliminating the mechanisms by which people felt the costs of war (draft, war taxes, introducing drones) has led to aimless conflicts with no predictable exit circumstances.
Days of Rage: America's Radical Underground, the FBI, and the Forgotten Age of Revolutionary Violence
Domestic bombing by radical leftists was a fact of life in US cities in the 1970s. Their ineffectiveness stems from lack of clear aims, capped functional network sizes, and drug addiction.
Catastrophic Care: How American Health Care Killed My Father—and How We Can Fix It
Once enacted, we must judge policies by their effects, not the intentions of their authors.
The Revolt of the Public and the Crisis of Authority
Humans tend to identify very narrow problems to solve instead of looking at systems holistically; our solutions change the context around those problems, so our actions implicitly have more unintended effects than intended.
A More Beautiful Question: The Power of Inquiry to Spark Breakthrough Ideas
When people fail to see what’s right in front of them, it’s usually because they stopped looking too soon.
The Age of Gold: The California Gold Rush and the New American Dream
California is forever in a Gold Rush: persistently cheerful, energetic, courageous, and teachable, but also careless, hasty, trusting in luck, and blind to our social duties.
The Writer's Journey: Mythic Structure for Writers
Stories are orientation devices, making us more aware of our identities and responsibilities to the world. They act on us by disorienting us into a state of suggestibility with frequent reversals of circumstance.
Impro
Our personalities are not our true selves, but masks that we put on to control how others see us, different from the crowd along acceptable dimensions. Those who appear most 'normal' are those most suggestible to social coercion.
Hyperion
In seconds of decision, entire futures are made.
Return to the Little Kingdom: Steve Jobs, the Creation of Apple, and How It Changed the World
Big thinkers often do big things; small thinkers never do big things. The spray of a public splash is made of facades, gestures, and illusions.
Original Gangstas: The Untold Story of Dr. Dre, Eazy-E, Ice Cube, Tupac Shakur, and the Birth of West Coast Rap
Vision and craft unite. Money and ego divide.
Zen Mind, Beginner's Mind: Informal Talks on Zen Meditation and Practice
There is no certain way that exists permanently. Moment after moment, we have to find our own way.
Cribsheet: A Data-Driven Guide to Better, More Relaxed Parenting, from Birth to Preschool
There is no perfect set of choices in parenting. The best you can do is to identify your preferences and constraints and make the best decision you can with available data. But definitely vaccinate.
Cradle to Cradle: Remaking the Way We Make Things
It’s not enough to delay the depletion of resources with improvements to efficiency. For the sake of future generations, we must design products and processes which nourish and replenish our environment.
The Japanese Mind: Understanding Contemporary Japanese Culture
It is neglectful to not try hard; make a serious effort, regardless of the outcome.
Designing Games
Stay fluid, don’t assume the future, and pay attention to dependency-driven risk.
Surface Detail
All we ever are is a bit of the universe, thinking to itself.
The Outsiders: Eight Unconventional CEOs and Their Radically Rational Blueprint for Success
Focus on the key assumptions. Insights come from taking variables to extremes.
High Growth Handbook
Choose carefully the role models you aim to emulate. Know the mental models shaping their actions, their actual actions, where their circumstances aligned with your own, and the eventual outcomes.
An Elegant Puzzle: Systems of Engineering Management
To grow as a manager, pursue scope: taking responsibility for the success of increasingly important and complex facets of your organization and company.
Pictures at a Revolution: Five Movies and the Birth of the New Hollywood
Building the new guard requires pairing determined outsiders with the most flexible members of the establishment.
Other Minds: The Octopus, the Sea, and the Deep Origins of Consciousness
If you make what you measure, then to evaluate intelligent systems with humans as your only benchmark is to miss out on the opportunity to build new, complementary forms.
Starting Point: 1979-1996
Even in a chaotic, ruined world, there will always be good things and exciting things.
Competitive Strategy: Techniques for Analyzing Industries and Competitors
Strategy is an exercise in empathy and self-awareness: what can your rivals see, and what does that make them think and feel? What are your strengths and weaknesses, and what paths do they leave available to you?
Secrets of Sand Hill Road: Venture Capital and How to Get It
With negotiating ability or leverage, you might be able to get “better” terms today - but consider the bounds those terms might place around your actions in future circumstances.
Dune
You can’t always take the clear, safe course — that path inevitably leads to stagnation
Creating Customer Evangelists
Listen to your customers and identify how your product/service or the buying experience around it could make their lives more fulfilling. Evangelism comes from wanting to share something that’s made your life better and could work for someone else too.
American Prometheus: The Triumph and Tragedy of J. Robert Oppenheimer
Beware those who conflate dissent with disloyalty.
Reality is Broken: Why Games Make Us Better and How They Can Change the World
People want to work at the edge of their abilities, to get feedback that extends what they’re capable of, and to see that their efforts result in meaningful impact on the world around them
The Book of Why: The New Science of Cause and Effect
An uncertain answer to the right question is much better than a highly certain answer to the wrong question.
The Effective Executive: The Definitive Guide to Getting the Right Things Done
Organizations aren’t more effective because they have better people; they have better people because their standards, habits, and climate motivate self-development
I Am a Strange Loop
Our sense of self, of there being an “I”, is a story the brain tells itself about why it does the things it does. It is our ability to perceive information, categorize it, and use it to predict the future, turned inward and endlessly reinforced.
What You Do Is Who You Are: How to Create Your Business Culture
Your culture is the set of norms that shape people’s decision-making when you aren’t around. Cultivate the virtues that you can embody and follow, and don’t let ethical principles go unsaid.
Leadership: In Turbulent Times
Great leaders cultivate a shared understanding of where the group is going and why.
Recruit Rockstars: The 10 Step Playbook to Find the Winners and Ignite Your Business
The best employees want to know the end goal for themselves and the company as a whole, the time frame and constraints they need to work within, and that they have the flexibility to forge their own path to that point
Creative Selection: Inside Apple's Design Process During the Golden Age of Steve Jobs
In any complex effort, communicating a well-articulated vision for what you’re trying to do is the starting point for figuring out how to do it.
2020:
Wild Cards
If you wish to find the unclouded truth, do not concern yourself with right and wrong.
Who Is Michael Ovitz?
The truth is the ultimate sales tool. Favors come back around. No conflict, no interest.
The Wizard and the Prophet: Two Remarkable Scientists and Their Dueling Visions to Shape Tomorrow's World
People notice that when scientists go into their workshop they strip their objects of study of everything but a few measurable quantities. This often leads to the observation that what was stripped away was worthy, even essential.
How History Gets Things Wrong: The Neuroscience of Our Addiction to Stories
There is a disconnect between the state of the art in neuroscience and our common sense view of the world that people act on their internal, stable desires and beliefs
The Color of Law: A Forgotten History of How Our Government Segregated America
Local, state, and federal government agencies enabled and enforced segregation throughout the 20th century, keeping African Americans from participating in wealth and income growth in housing and labor markets
Amusing Ourselves to Death: Public Discourse in the Age of Show Business
Since the introduction of the telegraph, electronic media has pushed our discourse toward irrelevance, impotence, and incoherence by transforming important elements of our culture into entertainment products
Talent is Overrated: What Really Separates World-Class Performers from Everybody Else
To achieve elite performance in any field, isolate specific aspects of your technique and find ways to do many repetitions involving that technique with a scoring mechanism or outside observer who can provide feedback on whether you are improving
Something Wicked This Way Comes
You can’t have everything — drop your remorse and do good for the people you love, today.
The Socialist Manifesto
Instead of dogmatically pushing for historically-advocated policies, it is better to pursue your vision for the world by finding the most viable paths from the circumstances today to that potential future
The Design of Everyday Things
It turns out that most cases are “special.” Any system that does not allow for special cases will fail.
The Most Important Thing
Seek value in the knowable (companies, industries, securities), not the unknowable (economies, markets)
Freemium Economics: Leveraging Analytics and User Segmentation to Drive Revenue
Business models fund development methodologies, not the other way around.
The Pragmatic Programmer
A successful tool adapts to the hands that use it.
A History of the Bible: The Story of the World’s Most Influential Book
Building a tribe requires the extension of folk-memories that originally affected only a few to a wider and more distant set of converts.
What I Talk About When I Talk About Running
The most important thing for long-term projects is setting your pace. The problem is getting the flywheel to spin at a set speed — to get to that point takes as much concentration and effort as you can manage.
Against The Gods: The Remarkable Story of Risk
Only the foolhardy take risks when the rules are unclear.
Blood, Sweat, and Pixels
In intensely iterative creative processes, everything tends to come together at the last minute.
Radical Candor
A work culture where criticism is given from a place of caring for one another’s success is scarier but safer. Members of the team feel where their behavior has been deficient, but it ultimately helps everyone get closer to achieving their goals.
Expert Political Judgement
To improve judgement, draw on information from non-redundant sources and update your beliefs as you encounter unexpected evidence.
Red Mars
Very few people ever bother to find out what other people really think. They are willing to accept whatever they are told about anyone sufficiently distant.
How Asia Works
No significant economy has successfully developed through policies of free trade and deregulation. What works: capital accumulation through household farming, manufacturing focused on exports, and regulated banks supporting these efforts.
Stubborn Attachments
If we valued the lives of people in the future, we'd accelerate processes that bring compounding benefits and work harder to diminish processes that bring compounding costs.
The Fifth Season
History is always relevant.
Contagious: Why Things Catch On
People share things that evoke strong emotion, make them look more interesting, or carry practical value that will make them look helpful. They work out what things have these attributes by watching what others do and respond to in public spaces.
In The Blink of An Eye
Using the right technology in the right way for a particular project centers on finding the correct balance of pre-planning and spontaneity.
Catching the Big Fish: Meditation, Consciousness, and Creativity
Everyone on the team is rehearsing until they get it right. Do an iteration, talk about it, help each other make sense of their parts and the whole, get closer to a common shared idea, and go again.
Modern Monopolies
Left unchecked, a network will deteriorate in quality of new users and quality of interactions between users.
The Unwinding: An Inner History of the New America
Revolutionaries are often disappointed because an idea must be very small for people to give it a chance.
Ametora: How Japan Saved American Style
Mastering the minutiae of traditional forms is the key to understanding how and when to break rules to create something new.
The Manager’s Path: A Guide for Tech Leaders Navigating Growth and Change
Be kind, not nice. Do the things that actually set people up to succeed, not just make them feel better in the moment.
The Great CEO Within: The Tactical Guide to Company Building
Teams with formal systems for having priorities flow from leadership to the team and feedback from the team to leadership will inevitably overcome those dependent on unfocused raw talent.
Cognitive Surplus: How Technology Makes Consumers into Collaborators
Increases in community size, decreases in cost of sharing, and increases in clarity all make knowledge more combinable.
Stanley Kubrick: American Filmmaker
You can’t know in advance what pleasant surprises might come from the next iteration. Do it again.
Managing Humans
Until you ship the Real 1.0, your Pitch, Process, and Product should rapidly evolve with new information.
The Ride of a Lifetime: Lessons Learned From 15 Years As CEO of The Walt Disney Company
Longshots usually aren’t as long as they seem. With enough thoughtfulness and commitment, the boldest ideas can be executed.
No Rules Rules: Netflix and the Culture of Reinvention
Increase the density of talent on your team and lead with context rather than top-down controls. A roster of high performers will figure out how to be most effective.