My favorites books, essays, and videos.
Meditations on Moloch by Scott Alexander
Why does the system persist — and perhaps get worse — even though the participants all hate it? Because "things that work from a god’s-eye view don’t work from within the system."
The Vulnerable World Hypothesis by Nick Bostrom
"A vulnerable world: one in which there is some technological development at which civilization almost certainly gets devastated by default."

Will our drive to invent new things eventually destroy us?
In Praise of the Gods by Simon Sarris
A compelling case for balancing rationalism and intuition. Rationalism is good, but granting it total supremacy much robs us of our soul.
Life is Short by Paul Graham
"If life is short, its shortness should take us by surprise. And that is what tends to happen. You take things for granted, and then they're gone."
How I Found Freedom in an Unfree World by Harry Browne
Browne’s premise is that attempting to change the world will be a futile endeavor for most. Instead, he outlines a libertarian personal philosophy for changing yourself and your immediate environment in order to achieve your goals and live the life you desire.
Solitude and Leadership by William Deresiewicz
A great speech by Deresiewicz. He submits that solitude, deep thought, and deep work are the keys to effective leadership.
Letters from a Stoic by Seneca
Stoicism has made a huge comeback in recent years and Letters from a Stoic is my favorite Stoic text. The letters are believed to be written by Seneca to his friend Lucilius explaining how to be a good Stoic.
The Crossroads of Should and Must by Elle Luna
Everyone is pulled between two choices – what their peers and environment tell them they should do, and what they know they must do.
12 Rules for Life by Jordan Peterson
Twelve lessons for how to live virtuously in the modern world. What I love about Peterson’s writing is that he weaves together what he’s learned from his psychology practice along with his deep knowledge of religious scripture. The modern Western world is deeply rooted in Christianity, so whether one is religious or not, understanding these foundational narratives is crucial to understanding modernity. Combined with Peterson’s psychology anecdotes and excellent writing, 12 Rules for Life is an incredible read.
Hardcore History: The Death Throes of the Republic by Dan Carlin
The epic history of the decline of the Roman Republic as told by Dan Carlin.
Fast by Patrick Collison
An epic, inspiring list of “people quickly accomplishing ambitious things together.” My favorite:
On August 9 1968, NASA decided that Apollo 8 should go to the moon. It launched on December 21 1968, 134 days later.
How This All Happened by Morgan Housel
An incredible look back at the modern economy and how it was created over the 70 years since WWII.
What the Hell is Going On? by David Perell
A deep dive on how the shift from information scarcity to information abundance has fractured established powers in commerce, education, and politics.
Flags of Our Fathers by James Bradley
The flagraising on Iwo Jima is the most reproduced photograph in history. It was taken almost by accident—the photographer wasn’t even looking through the lens of his camera when he snapped the shot. After learning that his late father was one of the six flagraisers, Bradley dedicates himself to researching the story of the flagraisers, how they ended up in the famous photo, which of them survived the battle, and the often tragic later years of the survivors.
The Purpose of Technology by Balaji Srinivasan
A brilliant reframing which argues that the ultimate purpose of all technology is to eliminate mortality.
JUMP by Mike Solana
People often joke you can’t change the world with a tweet. But it’s more apparent now than ever that you can. The problem is, in practice, a meme at rapid global scale doesn’t often look like freedom, or justice, or prosperity. It looks like a billion people doing the same thing, at the same time, in a temporary state of madness.
The Refragmentation by Paul Graham
Graham puts forward a theory that our fragmenting society is not due to forces driving us apart, but rather the erosion of anomalous forces that kept us together. Fragmentation is the norm, not the exception.
Next door in Nodrumia by Scott Alexander
The fictional town of Nodrumia is formed by a group of drum haters (Nodrumia = no-drum-ia) who ban drums in their community. Through the lens of Nodrumia, Alexander explores NIMBYism, exit costs, and libertarian philosophy applied to local governance.
It's Charisma, Stupid by Paul Graham
Paul Graham introduces his theory for how to win presidential elections. He discusses the 11 presidential elections since the advent of televised debates to prove that more than any single issue or party, the charismatic candidate always wins.
You have to engage with the world to change it by Shyam Sankar
You can’t advance the world’s largest institutions by complaining from the sidelines. You need to get in the game and change them from within.
This Old Man by Roger Angell
A beautiful New Yorker longform about life in your 90s.
The Intellectual Yet Idiot by Nassim Nicholas Taleb
A classic Talebian tirade against Ivy League “intellectuals” with no skin in the game.
The IYI pathologizes others for doing things he doesn’t understand without ever realizing it is his understanding that may be limited. He thinks people should act according to their best interests and he knows their interests, particularly if they are “red necks” or English non-crisp-vowel class who voted for Brexit. When plebeians do something that makes sense to them, but not to him, the IYI uses the term “uneducated”. What we generally call participation in the political process, he calls by two distinct designations: “democracy” when it fits the IYI, and “populism” when the plebeians dare voting in a way that contradicts his preferences. While rich people believe in one tax dollar one vote, more humanistic ones in one man one vote, Monsanto in one lobbyist one vote, the IYI believes in one Ivy League degree one-vote, with some equivalence for foreign elite schools and PhDs as these are needed in the club.
The Premium Mediocre Life of Maya Millennial by Venkatesh Rao
Venkatesh Rao describes the premium mediocre experience at length. He dives into the traits of those in premium mediocre class, their standing in the social hierarchy, why it all matters, and how to escape it.
On Political Correctness by William Deresiewicz
Deresiewicz explains the free speech crisis at college campuses. Political correctness, though well-intentioned, has stifled open dialogue. He advocates for civility—but not at the expense of free speech and open inquiry.
Crony Beliefs by Kevin Simler
Crony Beliefs are beliefs that exist for the purpose of fitting in or virtue signaling, and are often at odds with reality. Simler discusses these beliefs, how to identify them, and the danger they pose when we hold crony beliefs that go unrecognized.
Decomplication: How to Find Simple Solutions to Hard Problems by Nat Eliason
Hard problems intuitively feel like they require complicated solutions. But this complication is unnecessary. Artificial complexity drains us of our energy, money, and motivation. Nat explains the forces that create artificial complexity and their detrimental impact, and then demonstrates how to identify and eliminate it from our lives.
10-Point Scale & Wikipedia by Nick Yoder
Publish more often using Nick Yoder's system to fight perfectionism. Its simple: publish everything, no matter how half-baked. At the top of each post, give it a score from 1 to 10 to denote how rough or developed the ideas are.
Recommended Security and Privacy Tools by Digital Fortress
Tools for improving your security and privacy across the web, on your devices, and for your cryptocurrency.
The Wired Guide to Digital Security
An excellent resource for securing your digital life and keeping as much private as possible. The content is nicely broken into three tiers of security needs: civilian, public figure, and spy. Each set of articles walks the reader through increasingly serious privacy and security measures.
The Privacy Project by The New York Times
A collection of articles and guides about privacy, surveillance, and how to be better equipped to avoid it.
How to Communicate Privately in the Age of Digital Policing
An extremely detailed guide for getting started with encrypted messaging and email tools.
I Tried Hiding From Silicon Valley in a Pile of Privacy Gadgets by Joel Stein
A fun but scary look at just how closely we are tracked by Silicon Valley companies and how hard it is to avoid.
“Until people demand a law that makes privacy the default, I’m going to try to remember, each time I click on something, that free things aren’t free. That when I send an email or a text outside of Signal or MySudo, I should expect those messages to one day be seen.”
Design & Product
The Best Interface is No Interface by Golden Krishna
“There’s an app for that” used to be a blessing—now it’s a curse. The proliferation of touchscreen interfaces for every purpose are the problem, not the solution. Golden Krishna explores a world where designers think outside of the smartphone to build practical, delightful products.
Butterick’s Practical Typography by Matthew Butterick
The only typography resource you need: there are other good ones, but this is the definitive guide for learning the principles of beautiful typography.
Stanford Design Thinking Bootleg
A great starter’s guide to design thinking. More useful if you’re beginning in design, but great to reread every now and then. The original was called The Bootcamp Bootleg but has since been updated with new sections and exercises.
East of Eden by John Steinbeck
My all-time favorite book. Steinbeck explores good and evil by following two families in Salinas Valley.

John Steinbeck about East of Eden (from Wikipedia):
“It has everything in it I have been able to learn about my craft or profession in all these years. I think everything else I have written has been, in a sense, practice for this.”
The Unbearable Lightness of Being by Milan Kundera
Beautifully written with strong philosophical underpinnings. Nietzsche’s eternal recurrence suggests that every decision will be made ad infinitum, thus making decisions difficult and meaningful, and giving them weight. But reality, as described by Kundera, occurs once and never again, which makes it “light” — but being light has its own challenges.
Einstein's Dreams by Alan Lightman
A short but deeply resonant book. Each of the ~30 chapters has a different conception of time, and each of these alternate universes illustrates something about our complicated relationship with time.
Flowers for Algernon by Daniel Keyes
Another short but profound book. This book is the (fictional) journal of a severely handicapped man who joins an experiment to regain his intelligence. The experiment is a success and he begins – for the first time – to really understand his life.
Watchmen by Alan Moore
A graphic novel, but a novel, not a cartoon. Set in an alternate history where Nixon is elected for a third term, tensions with the Soviet Union are at an all-time high and the Doomsday Clock is almost at midnight. The titular Watchmen are a group of vigilantes who are retired and outcast. When one of the Watchmen is mysteriously murdered, the remainder come out of hiding to find the killer. Interesting political and philosophical underpinnings, awesome artwork, and a gripping story.
When I'm gone by Rafael Zoehler
My favorite piece of fictional writing online. Before a young father passes away, he leaves a box of letters for his son to read as he grows up.
The Picture of Dorian Gray by Oscar Wilde
A wonderfully written short book about a man with a beautiful face and a corrupted soul. Oscar Wilde’s writing style is fun and unique, and the end of the story is chilling.
The Count of Monte Cristo by Alexander Dumas
The original revenge and adventure story. The middle drags a bit, but the first and final thirds of the book are page-turners, and it has one of the most satisfying endings of any book I’ve read.
Father Guido Sarducci's Five Minute University
“The idea is this: in five minutes, you learn what the average college graduate remembers five years after he or she is out of school.”
Heartwarming and just a good read.
Strange Planet
Adorable alien cartoons.
Wendover Productions
Well-produced mini-documentaries. I especially love their videos about aviation.