Bookshelf

Note: just because something is on this list doesn't mean I like it, or agree with everything it says. It's what I've read—no more, no less.

Books

By order of reading, roughly.

• O'Brien, Robert C. Mrs. Frisby and the Rats of NIMH.
• Kirch, Olaf. Linux Network Administrator's Guide. How-to guide on throwing a preteen LAN party.
• Raymond, Eric S. The Cathedral and the Bazaar.
• Lee, Harper. To Kill a Mockingbird.
• Golding, William. Lord of the Flies.
• Hemingway, Ernest. The Old Man and The Sea.
• Powell, Colin. My American Journey.
• Salinger, J.D. The Catcher in the Rye
• Franklin, Benjamin. Autobiography of Benjamin Franklin.
• Orwell, George. Nineteen Eighty-Four.
• Plato. The Republic.
• Jubien, Michael. Contemporary Metaphysics: An Introduction.
• Mill, John Stewart. Utilitarianism.
• Schlosser, Eric. Fast Food Nation: The Dark Side Of The All-American Meal.
• Martel, Yann. Life of Pi. Pissing Patel.
• Schwartz, Randal L., et al. Learning Perl. My all-time favorite "learn to program" book. These guys just nailed it. Perl is unhygenic, write-only, and has the most clunky OO imaginable, but its community was first-rate.
• Eargle, John, and Augspurger, George. JBL Sound System Design Reference Manual. When preteen LAN parties turn into high school speaker-building parties.
• Hume, David. An Enquiry Concerning Human Understanding. I considered minoring in philosophy before ultimately choosing math.
• Adams, Scott. God's Debris.
• Richter, Jeffrey. CLR via C#. Deep geek-out on MSIL/CLR during my first Microsoft internship in 2005.
• Sullivan, Bob. Gotcha Capitalism. Jeremiad against concentrated, non-competitive industries.
• Kiyosaki, Robert. Rich Dad Poor Dad: What the Rich Teach Their Kids About Money That the Poor and Middle Class Do Not. The true test of a book for me is whether I appreciate it more or less with time. On my first reading, I learned a bit about compounding and investment. 8-10 years later, I read it again and was really turned off by the author's crass materialism, and disrespectful attitude toward his employees. The real genius here isn't the content—it's the storytelling, and how he fooled so many people into buying such a turd of a book.
• Welling, Luke, and Thompson, Laura. PHP and MySQL Web Development. Web development for simpler times.
• Tolkien, JRR. The Hobbit
• Tolkien, JRR. The Lord of the Rings
• Gladwell, Malcolm. The Tipping Point: How Little Things Can Make a Big Difference.
• Bossidy, Larry, and Charan, Ram. Execution: The Discipline of Getting Things Done. Mediocre business book, probably not worth your time.
• Norman, Donald A. The Design of Everyday Things. Seminal book on design from the early-2000s. Great books like this have a way of disappointing; their conclusions seem so "obvious" (I feel this way also when watching The Matrix). I have to remind myself when reading books like this, things that seem obvious today often weren't so obvious, 20+ years ago, at first publication.
• Surowiecki, James. The Wisdom of Crowds.
• Berkun, Scott. The Art of Project Management. One of the first books I read on software project management. Less popular than Brooks, though I think it will age better. Scott Berkun is really active in the Seattle tech/meetup community, and I'm happy he made a second career out of writing, something I wish more practitioners would do.
• Wolfe, Tom. The Bonfire of the Vanities.
• Aczel, Amir. Chance: A Guide to Gambling, Love, the Stock Market, and Just About Everything Else. A few nuggets of practical advice on house-buying and card-playing.
• Heller, Joseph. Catch 22.
• David Keirsey. Please Understand Me II: Temperament, Character, Intelligence.
• Anderson, Chris. The Long Tail: Why the Future of Business is Selling Less of More .
• Taleb, Nassim. Fooled by Randomness.
• Harris, Judith Rich. The Nurture Assumption. Heredity and environment, not "nature vs. nurture".
• Lewis, Michael. Liar's Poker: Rising through the Wreckage on Wall Street.
• Gilbert, Daniel. Stumbling on Happiness.
• Pausch, Randy. The Last Lecture.
• Brealey, Richard, et al. Corporate Finance. I read this book because I wanted to understand discounting. It delivered.
• Prahalad, C.K. The Fortune at the Bottom of the Pyramid: Eradicating Poverty Through Profits.
• Derman, Emanuel. My Life as a Quant.
• Lowenstein, Roger. When Genius Failed: The Rise and Fall of Long-Term Capital Management. A cautionary tale about overconfidence, and taking risks you don't understand (especially if asymmetrical/fragile).
• Dennis, Felix. How to Get Rich. When I first read this book in my mid-20s, it seemed exotic, even crass. After working ten years, I appreciate its honesty. This guy isn't going to win a Nobel Prize or start the next Microsoft, but he understands the people side of things better than most.
• Obama, Barack. The Audacity of Hope: Thoughts on Reclaiming the American Dream. Illinois (my home state) as a microcosm of the United States.
• Florida, Richard. The Rise of the Creative Class: And How It's Transforming Work, Leisure, Community, and Everyday Life.
• Klarman, Seth. Margin of Safety. Cult classic value investing text. Out of print, but you can find it if you try.
• Covey, Stephen. The 7 Habits of Highly Effective People. Easy to understand, remarkably difficult to master.
• Dominus, Mark Jason. Higher-Order Perl. "Hey, I'm an electrical engineer. Designing a compiler can't be too hard, can it?"
• Hill, Napolean. Think and Grow Rich.
• Kidder, Tracy. The Soul of A New Machine
• Florida, Richard. Who's Your City?: How the Creative Economy Is Making Where to Live the Most Important Decision of Your Life.
• Gawande, Atul. Checklist Manifesto. Checklists are a good idea that I use often. A more cynical take on this book: how broken is healthcare, that getting doctors to do something that costs nothing and reduces infection rates so much, is worthy of writing a book?
• Brooks, Frederick P., Jr. The Mythical Man-Month. How was software built in the 70s? Classic, but dated.
• Gerber, Michael E. The E-Myth Revisisted. Another book I read when too young to appreciate.
• Pollan, Michael. The Omnivore's Dilemma.
• Rubin, Bob. In an Uncertain World. Wall Street veteran's take on working (well) in politics.
• Gunther, Max. The Zurich Axioms: The rules of risk and reward used by generations of Swiss bankers. I read a lot about trading and investment during my mid-20s "peak libertarian" phase. I taped a copy of these to the wall above my desk when I lived in Seattle.
• Robin, Vicki, and Dominguez, Joe. Your Money or Your Life: 9 Steps to Transforming Your Relationship with Money and Achieving Financial Independence. There are other, better ways to live than a 9-5 you can't stand.
• Rand, Ayn. Atlas Shrugged. Complaining about the writing or story means you missed the point.
• Feathers, Michael. Working Effectively with Legacy Code. All-time favorite technical book and sometimes gift, written by a guy who's seen a lot of code.
• Cain, Susan. Quiet: The Power of Introverts in a World That Can't Stop Talking.
• Fowler, et al. Refactoring. Improve the design of existing code, without changing its behavior.
• Christensen, Clayton. The Innovator's Prescription. Integrated fixed-fee providers (IFFPs) seem a good model for care delivery.
• Petricek, Thomas. Real-World Functional Programming: With Examples in F# and C#. I went deep into functional programming in 2008-2009, starting around the time I read Higher-Order Perl. I wouldn't try developing a game, operating system, or enterprise application in pure functional style, but I've observed that liberal application of functional techniques (e.g. static single-assignment, immutability) tends to produce easier-to-use, less buggy code.
• Sorkin, Andrew Ross. Too Big to Fail. Definitive historical narrative of the 2008 financial crisis. Surprisingly good reading.
• Huxley, Aldous. Brave New World. Huxley's dystopia has always felt more probable than Orwell's.
• Borges, Jorge Luis. Collected Fictions. Favorites: The Immortal, Library of Babel, House of Asterion. (Thanks, Ariel.)
• Ryan, Christopher, and Jetha, Cacilda. Sex at Dawn: How We Mate, Why We Stray, and What It Means for Modern Relationships.
• O'Shea, Donnal. The Poincare Conjecture: In Search of the Shape of the Universe. I never formally studied topology, but this book gave me good intuition about how relatively simple, finite structures (e.g. a ball) can appear "infinite" in lower-dimensional space.
• Putnam, Robert. Bowling Alone. The book that put "social capital" on the map.
• Battistella, Roger M. Health Care Turning Point: Why Single Payer Won't Work (MIT Press).
• Taleb, Nassim. The Black Swan: The Impact of the Highly Improbable. By far my least favorite book of the Incerto series, although perhaps the most well-known.
• Reich, Robert. Supercapitalism.
• Fowler, Martin. Patterns of Enterprise Application Architecture. Influential book about enterprise software in the "Big Java" era (early 2000s). Widely cited, but like Brooks, starting to show its age.
• Crockford, Douglas. JavaScript: The Good Parts.
• Spolsky, Joel. Joel on Software.
• Hunt, Andrew, and Thomas, David. The Pragmatic Programmer. Programming is a craft profession.
• Jay, Meg. The Defining Decade. Critiques the idea of using your 20s to "find yourself".
• Murray, Charles. Coming Apart. White America, then and now.
• Gamma, Helm, Johnson, Vlissides. Design Patterns: Elements of Reusable Object-Oriented Software. Classic, but dated (published 1994). Necessary reading for serious software developers, also a reminder how much better things have gotten, and will get (more expressive and automatic languages, less boilerplate, better performance).
• Stanley, Thomas J. The Millionaire Next Door. Portrait of American wealth outside industry clusters. I'm still trying to figure out how it works in Silicon Valley, or Hollywood.
• Fowler, Martin. Domain-Specific Languages
• Kim, Gene. The Phoenix Project
• Farley, David, and Humble, Jez. Continuous Delivery. Deliver change in small increments.
• Carnegie, Dale. How to Win Friends and Influence People
• Evans, Eric. Domain-Driven Design: Tackling Complexity in the Heart of Software 1st Edition. How to build data models, the beating heart of large-scale enterprise software.
• Vernon, Vaughn. Implementing Domain-Driven Design. Evans is great, but too hand-wavey; this book became "The Bible of HOLMS", the hotel property management system we built at shortbar.
• Duckett, Jon. HTML & CSS: Design and Build Websites. When I finally broke down, and decided it was time to learn about margins, padding, and other CSS features.
• Bauer, Cornelius, and King, Gavin. Java Persistence with Hibernate. When so-called "feral concurrency control" doesn't cut it.
• Lewis, Michael. The Big Short.
• Lopp, Michael. Being Geek.
• Pfeffer, Jeffrey. Power: Why Some People Have It and Others Don't.
• Taleb, Nassim. The Bed of Procrustes
• Cowan, Tyler. The Complacent Class. Why is travel getting slower?
• Kahneman, Daniel. Thinking, Fast and Slow. The story of two researchers trying to reconcile psychology and economics. 499 pages, no starch.
• Harari, Yuval Noah. Sapiens. Stories are everything.
• Osterwalder, Alexander, and Pigneur, Yves. Business Model Generation: A Handbook for Visionaries, Game Changers, and Challengers.
• Blank, Steve. The Startup Owner's Manual: The Step-By-Step Guide for Building a Great Company.
• Spolsky, Joel. Smart and Gets Things Done. Spolsky is an entertaining writer, if a bit lacking in substance.
• Wiegers, Karl. Software Requirements (Developer Best Practices). Good book on managing requirements for large, "engineered" software projects.
• Piketty, Thomas. Capital in the 21st Century
• Bogle, John. The Clash of the Cultures: Investment vs. Speculation
• Goldhill, David. Catastrophic Care. A surprisingly readable critique of life on "The Island"—the part of the economy (healthcare) where ordinary rules about pricing, competition, and customer service seem not to apply.
• Freeman, Steve. Growing Object-Oriented Software, Guided by Tests. Growth/gardening as a metaphor for software, which I wholeheartedly embrace.
• Lessig, Lawrence. Code 2.0. 20 years before everyone had an opinion on how facebook should be regulated, this guy wrote a book on it.
• Fisher, Roger and Ury, William. Getting to Yes: How To Negotiate Agreement Without Giving In. Issues, not positions.
• Bogle, John C. The Clash of the Cultures: Investment vs. Speculation. The father of indexing's critique of the "dual-agent society"—how money managers need to fight harder for their clients.
• Collins, Jim. Good to Great: Why Some Companies Make the Leap and Others Don't. On its face, it's easy to criticise a book about "great companies"—what even defines such a thing? But Collins and company did their homework. A forceful reminder that not everything worth knowing has an easy mathematical formulation.
• Burniske, Chris, and Tatar, Jack. Cryptoassets: The Innovative Investor's Guide to Bitcoin and Beyond. The finance perspective on cryptoassets.
• Narayan et al., Bitcoin and Cryptocurrency Technologies: A Comprehensive Introduction. The technical perspective on Bitcoin (particularly InfoSec academia, my professional home from 2008-2009).
• Peter, Laurence J. The Peter Principle
• Dalio, Ray. Principles: Life and Work. A book by a man who found his passion young, and is still going strong, 50 years later.
• Weinberg, Gabriel et al. Traction.
• Christensen, Clayton. How Will You Measure Your Life?. Management theorists's attempt to measure something that can't be measured. I found this book pretty disappointing.
• Taleb, Nassim. Antifragile
• Haidt, Jonathan. The Happiness Hypothesis
• Rees-Mogg, William. The Sovereign Individual. How long will nation-states remain the dominant form of political organization?
• Willink, Jocko, and Babin, Leif. Extreme Ownership. As my friend Sebastian put it, "A great book on military leadership, when that's what you need".
• Brooks, David. The Road to Character
• Duckworth, Angela. Grit
• Tully, Byron. The Old Money Book. Live well on any budget.
• Moynihan, Brendan. What I Learned Losing a Million Dollars. Great recommendation from my friend Luke Gotszling. Having worked and lived as a caddy through my teens/20s, this hit close to home.
• Cohen, Marty. The Party Decides. How do presidential elections actually work? Presents a good theoretical model of political parties (e.g. why they form). After Trump's election in 2016, this book felt short a few chapters.
• Milner, Murray Jr. Elites: A General Model. High-quality, cross-cultural academic synthesis of "elites": who they are, their types, their strategies for getting and keeping power. Recommended by the always-insightful Naval.
• Skidelsky and Skidelsky. How Much is Enough?: Money and the Good Life. The first time I encountered the conservative case against "the market society", a key underpinning of Brexit.
• Johnson, Steven. Farsighted. Read due to recommendation from noted VC Fred Wilson. Asks a lot of good questions but the answers given feel incomplete.
• Levy, William, and Erlanger, Steve. The Condominium Greenbook. Crash course to running the books at a 350-unit condo, which I did 2018-2020.
• Reinhart, Carmen M., and Rogoff, Kenneth S. This Time Is Different: Eight Centuries of Financial Folly.
• Marohn, Charles L., Jr. Strong Towns: A Bottom-Up Revolution to Rebuild American Prosperity. We don't celebrate maintenance—at our peril. But nobody celebrates well-maintained parks.
• McConnell, Steve. Code Complete 2. Most software is gardening; this book explains how to pour concrete.
• Cowan, Tyler. Stubborn Attachments. In the long run, growth, stability, and climate are all that matter.
• Myers, Scott. Effective C++
• Myers, Scott. Effective Modern C++. I've tried to learn C++ three times (2001, 2005, 2019). The fourth time could be the charm, but don't hold your breath.
• Oster, Emily Expecting Better
• Oster, Emily. Cribsheet
• Haskell, Jonathan. Capitalism Without Capital
• Buttigieg, Pete. Shortest Way Home: One Mayor's Challenge and a Model for America's Future. As a fellow product of the mid-90s Great Lakes, this was a fun read.
• Goodhart, David. The Road to Somewhere
• Bishop, Bill. The Big Sort: Why the Clustering of Like-Minded America is Tearing Us Apart.
• Willetts, David. The Pinch: How the Baby Boomers Took Their Children's Future - And Why They Should Give it Back.
• Tepper, Jonathan, and Hearn, Denise. The Myth of Capitalism: Monopolies and the Death of Competition
• Jones, Garett. 10% Less Democracy: Why You Should Trust Elites a Little More and the Masses a Little Less. We espouse democracy's benefits in the US, but rarely consider its costs. That's a mistake.
• Fitzgerald, F. Scott. The Great Gatsby. Standard high school reading I finally got around to, in my mid-30s.

Long-form Internet writing

I've read thousands of essays on the Internet. Some favorites:

• Valloppillil, Vinod. The Halloween Documents. Commercial software vendors saw free and open source software (FOSS) as a major competitive threat in the late 1990s. I think everyone would be surprised how things turned out.
• Lynn, Dallas. The Ladder Theory. Tim Urban might call this "How The Primitive Mind chooses a mate".
• Spolsky, Joel. Joel on Software. Favorites: Strategy Letter I: Ben and Jerry's vs. Amazon on how funding follows type of business, Things You Should Never Do, Part I on the danger of the "big rewrite to solve everything", and Fire and Motion on the intensely competitive nature of software development.
• Graham, Paul. Modern-day secular prophet of Silicon Valley. Favorites: What You Can't Say on censorship, Life is Short on the nature of bullshit and its dangers, How to Make Wealth as a structured way to think about income generation, The Bus Ticket Theory of Genius which is kind of the story of Ray Dalio's life, The Refragmentation as an alternate worldview to the 1950s big-labor/big-government consensus pushed by the New York Times and friends, How to Get Startup Ideas on living in the future and building what's missing.
• Akhmechet, Slava aka defmacro. Small number of high-quality essays I refer back to often. Favorites: How to build great products, 44 engineering management lessons, 57 startup lessons, and How to pick startup ideas. His second chapter is on Substack—equally good, better even, but much darker. Envy, How to get promoted.
• Yegge, Steve. Yegge's Google Platforms Rant. Why didn't Google build AWS?
• Lonsdale, Joe. A Deficit of Leadership. "The great lesson of leadership handed down to us from classical thinkers in every culture is that those who handle power must do so with a deep sense of responsibility for those whose lives they touch".
• Gurley and Klein. The Ezra Klein Show: VC Bill Gurley on Transforming Health Care. Two people with very different backgrounds and political views discuss what's wrong with healthcare
• Urban, Tim. Wait But Why. Book-length writing on several important topics including The Elon Musk Post Series, How to Pick a Career, and a new, long series called The Story of Us. Did I mention the articles are long?
• O'Church, Michael. 3 Class Ladders in America. I'm not sure if this was lifted from academic research, but it's the crispest definition of social class in the US I've read; it's also quite short.
• Dalio, Ray et al. Populism: The Phenomenon. A consise description of populism, and an argument why it may be the dominant political movement of the late 2010s/early 2020s.
• Mead, Walter Russell. The Once and Future Liberalism on the many, often confusing, meanings of "liberal" in 2020-era America.
• Bezos, Jeff. Statement by Jeff Bezos to the U.S. House Committee on the Judiciary. The story of Amazon, told by Bezos. Great insights into the competitive, fast-moving world of retail.
• Wealthfront: 2013 Silicon Valley Career Guide and Career-Launching Companies List. How the VC crowd picks places to work, and what they think is hot now. Most of the places on this list are the sort looking to hire MBAs—capital-light business model disruptors, not places doing heavy scientific innovation. Even if you're more independent-minded, it can be worth knowing what's considered "hot".

h/t Patrick Collison for the idea for the page.