Here's my reading list with ratings and detailed notes. You can read more about my reading and note taking system here.
If you want to receive my top 5+ book recommendations each month–with notes so you can dig in–and other exclusive content, sign up for my newsletter 👈👈👈
Sort by: Most Recent ｜ Highest Rated
The Black Swan: The Impact of the Highly Improbable – by Nassim Taleb
Date read: 1/28/18. Recommendation: 8/10.
A strong case could be made that Nassim Taleb is one of the most original minds of our time. It's well worth reading every book of his Incerto series, which includes: Antifragile, The Black Swan, The Bed of Procrustes, and Fooled by Randomness. Taleb defines Black Swans as events with the following three attributes: rarity, extreme impact, and retrospective (though not prospective) predictability. He discusses how the root of our inability to understand Black Swans lies in mistaking a naive observation of the past to be representative of the future. The book details specific themes that arise from our blindness to the Black Swan, including: confirmation bias, narrative fallacy, human nature, silent evidence, and tunneling. Taleb sets out to make us more aware of the biases in our logic as it relates to Black Swans so that we might better embrace our own humanity (that's part of it!) and avoid large-scale harmful predictions that might hurt our future. He advocates the "barbell" strategy and positioning ourselves to take advantage of positive Black Swans (lose small to win big) and situations where favorable consequences are much larger than unfavorable ones.
A More Beautiful Question – by Warren Berger
Date read: 1/19/18. Recommendation: 7/10.
I first heard Warren Berger on The Knowledge Project podcast, then purchased this book in an effort to improve my own questioning ability. While it is a great resource for asking better questions, this book offers so much more than that. It's an insightful look into the role of inquiry in modern life. Berger suggests that as the world becomes more complex and dynamic, questions become more valuable than answers. He offers a framework to formulate and ask better questions. But he also digs deeper into topics such as the age of adaptation, design thinking, our education system, and the reasons people avoid fundamental questioning. As an added bonus, there are some brilliant questions Berger challenges us to consider for ourselves along the way.
Zero to One – by Peter Thiel & Blake Masters
Date read: 1/12/18. Recommendation: 8/10.
I had high expectations for this one, considering it has become a sacred text for many startups and entrepreneurs. But Zero to One did not disappoint. The core of the book emphasizes that there is no single secret to innovation and entrepreneurship. But Thiel explains that if we want to to create a better future, we can't wait around, we have to go out and actually build it. He touches on concepts like vertical progress, opposite principles, monopolies, luck, venture capital, and the importance of getting the founders right when launching a new startup. The first half of the book is particularly brilliant. If you're an entrepreneur or working in technology, there's a reason this book is so highly rated.
The Inevitable: Understanding 12 Technological Forces That Will Shape Our Future – by Kevin Kelly
Date read: 12/27/17. Recommendation 7/10.
Kelly is a great teacher when it comes to helping others think beyond the realm of current possibilities. I often find myself fighting the inertia of the way things currently are, instead of looking at the inevitable trends and determining what's next. The specific forces he outlines become a bit repetitive, as there is significant overlap to each. But as a whole it's a great exercise in reminding yourself to take your thinking to the next level. Kelly is also refreshingly optimistic about the future of technology. He suggests that while we have little control over the inevitable technological forces on the horizon, we do have influence over their character and how symmetrical those relationships end up being.
Tribe of Mentors – by Tim Ferriss
Date Read: 12/20/17. Recommendation: 7/10.
Tribe of Mentors is built around a set of 11 questions that Tim set out to answer for himself by asking some of the most brilliant people (100+ in this book). Most of the questions are the same as the rapid-fire questions he uses in his podcast, "what book have you gifted the most?" and "what new belief, behavior, or habit has most improved your life?" There are a few nuggets of eye-opening wisdom, but the brevity kept things fairly shallow for me. I prefer Tools of Titans which covers a wider range of ideas in greater depth, and includes more of Tim's own notes and insights. For me, the most valuable part of Tribe of Mentors was its wealth of book recommendations
The Undoing Project: A Friendship That Changed Our Minds – by Michael Lewis
Date Read: 11/26/17. Recommendation: 8/10.
A fascinating look into the unlikely relationship and original contributions of two Israeli psychologists, Daniel Kahneman and Amos Tversky. Together they examined how people make decisions and predictions, and uncovered the systematic bias and errors that are inherent to each. They found that the human mind replaced laws of chance with rules of thumb–what they referred to as "heuristics," including availability, representativeness, anchoring, and simulation. Each heuristic reveals itself in the form of a cognitive bias (hindsight, recency, vividness, etc.). The papers of Kahneman and Tversky have had widespread positive implications, helping to educate experts in various fields (economics, policy, medicine) of their own biases, and ultimately leading to the creation of "behavioral economics."
The Airbnb Story – by Leigh Gallagher
Date Read: 11/15/17. Recommendation: 7/10.
Essentially a giant case study of Airbnb and its founders–Brian Chesky, Joe Gebbia, and Nathan Blecharczyk–which documents the evolution of their initial concept through its unprecedented growth. With regard to each of the founders, it was interesting to hear about their backgrounds and a great reminder that there's no one-size-fits-all approach to launching a company. Chesky and Gebbia were resourceful and got things off the ground without the traditional "technical DNA" that most investors in Silicon Valley obsess over. Their art-school background ended up being an asset that helped set them apart from competitors (better user interface), along with a perfect wave of external factors including timing, price, and a shift in consumer preferences towards artisanal experiences. Gallagher also does a great job remaining objective and presenting both sides of the story–as Airbnb hasn't come without controversy. It's one of the most engaging success stories of recent years.
Hooked: How to Build Habit-Forming Products – by Nir Eyal
Date Read: 11/11/17. Recommendation: 6/10.
Examines how to engineer user behavior, the moral implications, and how to leverage those findings to improve people's lives. Eyal documents each step of the "hook model," consisting of a trigger, action, investment, and variable reward. It's a short read and doesn't advance much past the basics, but if you're looking for an introduction to the startup mindset and how to begin building a product or service of your own, it's worth your time.
Poor Charlie's Almanack – by Charles T. Munger & Peter D. Kaufman
Date Read: 11/1/17. Recommendation: 8/10.
This is one of those must-read books because Munger's concepts are foundational to so many other authors and their ideas. To set expectations, the book is a monster. It took me months and multiple attempts to get through because there is so much there. It's comprised of 11 speeches given by Munger over the years. He details his now-popularized concept of "multiple mental models" and building a latticework of these models to improve cognition. Munger explains that adopting a more multidisciplinary approach is critical to achieving this, and cites Keynes when he suggests that it's better to be roughly right than precisely wrong. He also outlines "sit-on-your-ass investing" and the general approach that led to his success alongside Warren Buffett at Berkshire Hathaway. Poor Charlie's Almanack is one of those that you should sit with and reflect on so you can take it all in.
The Lessons of History – by Will & Ariel Durant
Date read: 10/22/17. Recommendation: 7/10.
A high-level look at the major lessons and themes throughout human history. The Durant's discuss race, religion, economics, capitalism, socialism, war, progress, and heritage, to name a few. They offer some interesting insights that are particularly relevant in today's politically-charged climate. They tackle the concentration of wealth, value of free enterprise, and increasing complexity of the economy. The Lessons of History also wisely reminds us to maintain a healthy level of skepticism as, "history is so indifferently rich that a case for almost any conclusion from it can be made by a selection of instances."
Principles – by Ray Dalio
Date read: 10/14/17. Recommendation: 8/10.
Dalio offers a detailed analysis of his principles for life and work, which have led him to become one of the most successful investors of our time. He offers these lessons with a refreshing dose of humility–not what you'd expect from the founder of one of the world's largest hedge funds. I gravitated towards his life principles where he champions truth, the value of painful mistakes, and the importance of looking beyond first-order consequences. His work principles also offer great insight into human relationships, conflict resolution, and the importance of building a culture of transparency.
Mastery – by Robert Greene
Date read: 9/30/17. Recommendation: 9/10.
You would be hard-pressed to find a more profound, relevant book, no matter your position in life. If I had to recommend a single book of Greene's to get you started, this would be it. He begins by defining mastery as the sensation we experience when we feel that we have a greater command of reality, other people, and ourselves. The book offers a deep dive into every element of mastery–including insight for those just starting out and searching for their life's task. True to form, Greene also provides detailed accounts from some of the greatest masters in history–Leonardo da Vinci, Benjamin Franklin, Charles Darwin, Albert Einstein, Paul Graham, and dozens more.
The 50th Law – by Robert Greene
Date read: 9/12/17. Recommendation: 7/10.
Greene pairs up with Curtis Jackson (50 Cent) to offer a real-world look into the laws of power and perseverance. He details stories from Jackson's rise and dissects how he was able to evolve and create momentum to escape dire circumstances. The more interesting sections of the book examine the underlying themes in Jackson's stories, such as fearlessness, self-reliance, and persistence.
Fooled by Randomness – by Nassim Nicholas Taleb
Date read: 8/28/17. Recommendation: 7/10.
Deep dive into the role of luck in the financial markets and life. Taleb emphasizes how we tend to only accept randomness in our failures, never in our successes. He discusses concepts like Monte Carlo math, Russian roulette, the Pólya process, nonlinearity and the human brain, and Buridan's donkey. Our tendency to favor the visible, narrated, and neat models, leads us to being fooled by randomness. He summarizes best by suggesting we are all idiots who are mistake prone, but only a handful of us have the rare privilege of knowing it.
The Bed of Procrustes: Philosophical and Practical Aphorisms – by Nassim Nicholas Taleb
Date read: 8/18/17. Recommendation: 8/10.
Great introduction to Taleb's take on uncertainty, which he discusses in detail in his other books that make up the Incerto series: Antifragile, Fooled by Randomness, and The Black Swan. This book offers a succinct look into how we deal with what we don't know. Taleb examines our tendency to package and reduce ideas into neat narratives that fit within the constraints of our limited knowledge.
On Writing Well: The Classic Guide to Writing Nonfiction – by William Zinsser
Date read: 8/14/17. Recommendation: 8/10.
An essential for nonfiction writers. This is the only book I keep within reach as I'm writing. Zinsser advocates a lean, direct writing style. He outlines strategies for crafting a more effective story that resonates with readers. This includes how to cut down first drafts, rewrite, organize the flow of an article, develop your own voice, address your audience, handle humor, and avoid the danger of clichés. There's also a practical style guide for reference that addresses everything from the use of qualifiers (rather, quite, very) to specific punctuation marks (dash, colon, exclamation point). Every writer will be better for picking this up.
Perennial Seller – by Ryan Holiday
Date read: 8/6/17. Recommendation: 8/10.
You can't go wrong with any of Holiday's work. His latest is a great read for anyone who considers themselves creative, and particularly insightful for writers and entrepreneurs. If you're thinking of writing a book or bringing an idea to life, start here and save yourself a few headaches. He outlines best practices for the creative process, along with the importance of positioning, marketing, and building a platform. The most important advice can be summed up as playing the long game. If you want to create something of lasting value, there are no shortcuts or paths to immediate gratification. Put in the work.
The Rational Optimist – by Matt Ridley
Date read: 7/29/17. Recommendation: 7/10.
I read this book to combat confirmation bias. I tend to romanticize the past and idealize the simple living we associate with the hunter-gatherer era. As such, I read a lot of books that fall in line with that interest. Ridley makes the argument that we're currently living in the best period of human history (which we are). He credits this to the free exchange of ideas and knowledge, which breeds even more innovation and knowledge. He details the driving factors of dynamic change, bottom-up innovation, and how the specialization of talents has led to mutual gain for everyone involved. It's a dense book but Ridley offers brilliant insight, which should give you a much needed boost of optimism for the future.
I Will Teach You to Be Rich – by Ramit Sethi
Date read: 7/22/17. Recommendation: 9/10.
The most accessible, practical book I've read on personal finance. Sethi dismisses trendy advice, such as cutting back on lattes, and instead emphasizes saving on the big purchases that really matter. And he's hilarious. This book is all about optimizing your strategy, prioritizing what matters most, and making money work for you (instead of obsessing over the minute details). This is a must read for anyone in their 20s or 30s, and should be a required reading for all who can still take advantage of the most valuable asset in investing: time.
If You Can: How Millennials Can Get Rich Slowly – William J. Bernstein
Date read: 7/15/17. Recommendation: 7/10.
An easy-to-read overview of the topics covered in his earlier book, The Investor's Manifesto. I prefer the depth and detail of the latter. But if you're looking for an introduction to investing in low-cost index funds and the importance of developing a financial strategy at an early age, this is a good starting place.
The Investor's Manifesto – William J. Bernstein
Date Read: 7/5/17. Recommendation: 8/10.
Champions an investment strategy focused on low-cost index funds that track the market, rather than attempting to guess on individual stocks. This is a must-read when it comes to investing. And it's not a massive encyclopedia. Bernstein offers a more rational approach to investing by detailing historic returns of various asset classes, the importance of diversification, and why you must play the long game if you have any hopes of coming out ahead.
Growth Hacker Marketing – by Ryan Holiday
Date read: 7/2/17. Recommendation: 8/10.
Flips traditional marketing (and ad agencies) on its head in favor of the growth hacker mindset. Growth hacking still requires pulling customers in but it favors a more innovative, effective, and cheaper method of reaching the target audience. Holiday emphasizes the importance of Product Market Fit and building a product that generates explosive, contagious reactions from those who first see it. Great foundation to have in place before building any product, service, or following. Digs into real examples of some of the most successful startups in Silicon Valley (Airbnb, Twitter, Dropbox, etc.) and how they were able to adapt, optimize, and make themselves indispensable in the process.
How to Be a Stoic – by Massimo Pigliucci
Date read: 6/24/17. Recommendation: 4/10.
New addition to my library of Stoic philosophy. I didn't feel like it brought enough original ideas to the table, based on the books already out there. It's essentially a walkthrough of Epictetus. If you're looking to get into Stoicism, check out A Guide to the Good Life, Ego Is the Enemy, or The Obstacle Is the Way. Or go straight to the source and read Seneca or Marcus Aurelius.
Live Your Truth – by Kamal Ravikant
Date read: 6/19/17. Recommendation: 6/10.
Not a book I would typically read, but there are a few hidden gems in its passages. If you're looking for inspiration, it's an easy read that you can get through in a day. Ravikant's handful of original, eye-opening insights make it worth it. Most of the book is focused on tapping into yourself and living an authentic life.
Homo Deus: A Brief History of Tomorrow – by Yuval Noah Harari
Date read: 6/11/17. Recommendation: 8/10.
Follow-up to Harari's critically acclaimed Sapiens. Whereas Sapiens is focuses on humanity's history, Homo Deus examines on humanity's future. Compelling book in its own right and worth reading. Guaranteed to expand your perspective and worldview. He discusses how Homo sapiens came to dominate the world, imagine and assign meaning to life, and what our current trajectory looks like.
The Time Paradox – by Philip Zimbardo and John Boyd
Date Read: 6/3/17. Recommendation: 8/10.
Fascinating look at how the way we regard time influences the course of our lives. Zimbardo and Boyd discuss six distinct time perspectives and illustrate how they are a reflection of our personal attitudes, beliefs and values. Great insight into the future-oriented world we live in and what that means for those who are more present-oriented. Also offers an interesting examination of various religions and their effect on individual time perspectives and behaviors.
Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days – by Jake Knapp
Date read: 5/28/17. Recommendation: 7/10.
Targeted to those working in technology, but useful lessons that can be applied more broadly. The authors pioneered their own rapid sprint process at Google Ventures. The book documents, step-by-step, the best way to examine, prototype, and test new ideas with customers, in a single week. The faster you can test out a new idea out and gather real feedback, the better. Great framework for creative problem solving, no matter what project or initiative you're working on.
Walden – by Henry David Thoreau
Date read: 5/21/17. Recommendation: 8/10.
Another classic. Thoreau documents his two years of simple living in a cabin near Walden Pond outside Concord, Massachusetts. He discusses themes of minimalism and self-sufficiency. Along the way he emphasizes the value of reconnecting with the natural world, and hints at stoic themes with his disdain for modern luxuries and comforts. His motivation for the book? Ensuring he was not wasting his life on trivialities, and instead living in a more deliberate, meaningful fashion.
The Art of Travel – by Alain de Botton
Date read: 5/15/17. Recommendation: 6/10.
Interesting book that feels like a series of essays. Dissects why we travel, the inspiration for doing so, and contemplates the experience of traveling abroad in a way that resonates with any seasoned traveler. In certain sections the language gets a bit too abstract and flowery for my taste. But if traveling is a large part of your identity, you'll appreciate de Botton's ideas.
A Guide to the Good Life: The Ancient Art of Stoic Joy – by William B. Irvine
Date read: 5/8/17. Recommendation: 8/10.
There's no better modern introduction to Stoicism. Contrary to today's understanding of the term as a lack of outward emotion, it's a life philosophy which cultivates rationality, appreciation, and joy. Irvine discusses the practicality of Stoicism, how it applies to our every day lives, and the importance of adopting a coherent philosophy of life that suits us as individuals. He hits on key concepts in Stoic philosophy and wraps them in a modern, logical context. I originally read this book over a year ago, and almost every single word struck a chord with me. It was one of my first encounters with Stoicism and I was surprised to find it matched almost identically with my existing worldview, which I had pieced together over the years.
On the Shortness of Life – by Seneca
Date read: 5/4/17. Recommendation: 8/10.
If you're looking to dive deeper into the works of Seneca, this is a great follow up to Letters from a Stoic. I read the Penguin Great Ideas edition. It's a collection of three essays filled with plenty of brilliant insight that Seneca is so well known for.
The 48 Laws of Power – by Robert Greene
Date read: 4/17/17. Recommendation: 9/10.
This took me months to read because there's so much to it. Perhaps the most detailed, convincing book I've ever read. Greene sets forth the individual laws of power and offers countless historical examples of each in practice. Not a book you're going to finish over the weekend, but a very important book and investment. Greene makes the argument that it's not a question of ethics, the game of power is inescapable, even in our daily lives. We might as well learn the game and master the laws of power so we're more aware, less distracted, and better able to negotiate situations in our favor.
Meditations – by Marcus Aurelius
Date read: 4/5/17. Recommendation: 9/10.
A cornerstone of Stoic philosophy, along with Letters from a Stoic by Seneca. It's critical which interpretation you read. I highly recommend the Modern Library version with an introduction by Gregory Hays. It's a short read with some of the most useful insights and aphorisms that money can buy.
Antifragile - by Nassim Nicholas Taleb
Date read: 4/1/17. Recommendation: 9/10.
Taleb introduces his concept of antifragility, which explains that certain things (including us) benefit from a degree of randomness, chaos, and disorder. While comfort, convenience, and predictability, breed the opposite–fragility. He presents this as part of what he calls 'the central triad' which ranges from fragile to robust to antifragile. As he explains antifragility, he discusses the value systems that hold us prisoner, ancestral vs. modern life, and Seneca's version of Stoicism. It's a dense read, but worth it for a glimpse into the originality of Taleb's ideas.
Check out my notes or Amazon for details and reviews.
If you're this far along in my reading list and you're on board with Stoicism, you'll enjoy this book. The greater your interest in Stoic philosophy, the more you're going to get out of the book. It's a tremendous resource. There's also a daily newsletter that offers brief overviews of many topics covered in the book. I don't normally recommend signing up for mailing lists, but this one is worth checking out. It's a great daily reminder and a solid introduction to Stoicism if you're looking for a place to start.
Sapiens: A Brief History of Humankind – by Yuval Noah Harari
Date read: 3/21/17. Recommendation: 10/10.
This is my favorite nonfiction book, hands down. It's one of the most important books you'll read and tackles some of the biggest questions we face. Harari tracks human evolution and the implications of the cognitive revolution through the agricultural, industrial, and scientific revolutions. There's a reason it's so popular and highly regarded. Just read it.
The Antidote: Happiness for People Who Can't Stand Positive Thinking – by Oliver Burkeman
Date read: 3/11/17. Recommendation: 9/10.
Rejects the self-help industry and the "power" of positive thinking. One of my favorite books that I've read this year. Burkeman sees the obsession with positive thinking and attaining happiness as counterproductive, and the very thing that makes us unhappy. There are great chapters on Stoicism and negative visualization, meditation and non-attachment, resourcefulness and the myths of goal setting, as well as impermanence and the pitfalls of seeking safety above all else. Makes the case that living meaningfully starts with the negative path to happiness–one which embraces uncertainty, insecurity, and the realities of every day life–so you can better appreciate when things go right. Unrealistic positive expectations are not only ineffective, they're often counterproductive.
Talk Like TED – by Carmine Gallo
Date read: 3/5/17. Recommendation: 7/10.
Gallo dissects the most popular TED talks and discusses the nine elements they all have in common. Great resource if you're hoping to improve your public speaking, presentation, or storytelling skills. The most engaging speakers elicit a set of common themes grouped as emotional, novel, or memorable. If nothing else, these lessons will help you become a better communicator.
Letters from a Stoic – by Seneca
Date read: 2/13/17. Recommendation: 9/10.
Introduction to Penguin Classics edition. Perhaps the most highly regarded/referenced work of Stoic philosophy along with Meditations by Marcus Aurelius. Go straight to the source. It's a classic and one of the most important works you'll read.
The Obstacle Is the Way – by Ryan Holiday
Date read: 1/30/17. Recommendation: 8/10.
Another great book by Holiday. I can't recommend his work enough. His roots in Stoic philosophy are evident in this book, as much of it is inspired by a Marcus Aurelius quote: "The impediment to action advances action. What stands in the way becomes the way." He emphasizes the importance of perspective and framing obstacles as an opportunity to practice virtue.
The Subtle Art of Not Giving a Fuck – by Mark Manson
Date read: 1/17/17. Recommendation: 7/10.
One of the most entertaining writers you'll find. Essentially a deep dive into one my favorite articles from his blog. The core of the book focuses on allocating more time and energy to what matters most (the appropriate allocation of fucks). Instead of over-investing in trivial, superficial things (the inappropriate allocation of fucks). He criticizes our culture's obsession with unrealistically positive expectations and the sense of inadequacy that it provokes. Life is a struggle, we should instead determine what we're willing to struggle for.
Tools of Titans – by Tim Ferriss
Date read: 1/14/17. Recommendation: 8/10.
If you're a fan of the Tim Ferriss podcast, you'll enjoy this book. It's a collection of all his interviews, distilled into their most useful bits of information. Ferriss offers insight into the habits and mental models of top performers across every industry, from fitness to Silicon Valley. This book is a gold mine for thought provoking quotes. A few of my favorite sections feature Naval Ravikant (entrepreneur/investor), Josh Waitzkin (chess prodigy), and Alain de Botton (philosopher). There are sure to be a handful of ideas that will resonate with you and help improve your own mental models. It's a book I revisit with regularity.
Tribe: On Homecoming and Belonging – by Sebastian Junger
Date read: 1/9/17. Recommendation: 9/10.
Thought-provoking, concise read that examines modern society and how poorly adapted we are for the convenience and predictability of modern life. I've gifted this book multiple times since reading it. Great look into why we crave community, raw experiences, and the effects of their absence.
Ego Is the Enemy – by Ryan Holiday
Date read: 1/5/17. Recommendation: 9/10.
My favorite Ryan Holiday book. If you haven't read any of his work yet, start here. It's a great look into how–in an effort to nurse our ego–we often act in opposition to our best interests. He discusses how to leverage ideas from Stoic philosophy, the pitfalls of self-narrative, and the importance of being a lifelong learner. Numerous life lessons and productive mental models packed into a quick read. Along with Tribe by Sebastian Junger, this is the book I've gifted the most in the past year.