The Best Books of 2016

Each year on this site, I share two of the emails that I send to my “book club,” which now reaches ~8,000 people each month. Here is the year-end email I sent yesterday. To sign up and receive suggestions every month, head here

This year I read 82 books, down from 103 last year. Having two kids is no joke! Below, I share my favorites from this past year.

Because I am committed to “growth without goals,” I will always be doing new things and sharing them with you. This year, the big new addition (on top of the website and this book email) was a podcast. The most popular episodes (measured by downloads) have been with Brent Beshore, Ted Seides, Jason Zweig, and Michael Mauboussin. The one with the fewest listens (understandably, she’s only 21!) was also the person who changed me most: Kiley Adams. The one that still has me thinking and confused in a good way is with Chris Cole.

I’ve realized that what connects all these pieces is inviting others into a search which has no end, where the search itself is the reward. That will continue. Because I don’t have goals, I don’t know what I will bring you in 2016, but I hope you’ll find whatever it is fun and useful.

Now back to the good stuff.

Just like last year, I have collected the best books that I read in 2016, with one sentence describing why I loved each book, and one passage to gauge (and pique) your interest. I’ve started the list with books I haven’t recommended before (think of these as my suggestions for December, with longer descriptions). As always, I hope you find something great to read.

At the end of 2015, this email went to four thousand people. In 2016, we doubled the list to eight thousand avid readers. I want to double it again. For that to happen, I need your help! If you have a friend that loves books or loves learning, send them this link so they can join our club:

I am deeply grateful to you all for your time, your kind notes, your book recommendations, and your willingness to engage in interesting conversations. Because of your interest and kindness, this book club has become a wonderful part of my life.

The Sovereign Individual by James Davidson and Lord William Rees-Moog

Sometimes, a book comes at me from all different directions. Out of nowhere, this book was being recommended by several people I count on for great recommendations. It was published in the late 1990’s, but is enjoying a very well-deserved resurgence. The first 2/3 or this book was the most interesting text of the year, filled with incredible history and visions of the future. The book outlines what the authors refer to as “mega politics” through the lens of “returns to violence.” They examine what the rate of return is on using violence through history, and suggest that we are entering (or already in) a long period where the returns to violence will fall considerably.  This will have profound implications on government, sovereignty, creativity, jobs, property, laws, and so on.

Many of their predictions from the late 90’s have come true. Many didn’t. But they seem to get some of the biggest trends right. There are passages that are downright eerie in the context of Trump’s rise to the presidency. The message of the book was ultimately very hopeful for me.

In the future, one of the milestones by which you measure your financial success will be not just how many zeroes you can add to your net worth, but whether you can structure your affairs in a way that enables you to realize full individual autonomy and independence

Finite and Infinite Games by James Carse

A deep thank you to Taylor Pearson for recommending this book to me. I absolutely loved it. It hits at a lot of the themes that I think about a lot—play, growth, meaning, etc—through a neat dichotomy of infinite vs finite games. Most people are “finite players,” but abiding joy comes through infinite play. I really, really loved this book and will re-read it often.

Finite players play within boundaries; infinite players play with boundaries.

Because infinite players prepare themselves to be surprised by the future, they play in complete openness. It is not an openness as in candor, but an openness as in vulnerability. It is not a matter of exposing one’s unchanging identity, the true self that has always been, but a way of exposing one’s ceaseless growth, the dynamic self that has yet to be.

The joyfulness of infinite play, its laughter, lies in learning to start something we cannot finish.

The Everything Store: Jeff Bezos and the Age of Amazon by Brad Stone

A history of my favorite company and its enigmatic leader.

“One early challenge was that the book distributors required retailers to order ten books at a time. Amazon didn’t yet have that kind of sales volume, and Bezos later enjoyed telling the story of how he got around it. “We found a loophole,” he said. “Their systems were programmed in such a way that you didn’t have to receive ten books, you only had to order ten books. So we found an obscure book about lichens that they had in their system but was out of stock. We began ordering the one book we wanted and nine copies of the lichen book. They would ship out the book we needed and a note that said, ‘Sorry, but we’re out of the lichen book.’ ”

Spent: Sex, Evolution, and Consumer Behavior by Geoffrey Miller

A book that changed how I view human behavior forever.

The trouble is not that marketing promotes materialism. Quite the opposite. It promotes a narcissistic pseudospiritualism based on subjective pleasure, social status, romance, and lifestyle, as a product’s mental associations become more important than its actual physical qualities. This is the whole point of advertising and branding—to create associations between a product and the aspirations of the consumer, so the product seems to be worth more to the consumer than its mere physical form could possibly warrant. Marketing actually avoids materialism at all costs, for if consumers comparison shopped solely on the basis of objective material features and costs, the products themselves would be reduced to commodities—and commodities cannot be sold for serious profits in a competitive market.

The Hidden Life of Trees: What They Feel, How They Communicate-Discoveries from a Secret World by Peter Wohlleben

The best book I’ve ever read on nature; cemented my love for the woods.

As people, we easily lose sight of what is truly old for a tree, because modern forestry targets a maximum age of 80 to 120 years before plantation trees are cut down and turned into cash. Under natural conditions, trees that age are no thicker than a pencil and no taller than a person.

Streaming, Sharing, Stealing: Big Data and the Future of Entertainment by Michael D. Smith, Rahul Telang

Helped me understand entertainment/information based content businesses in an entirely new way.

The big companies did agree on one element of success: the ability to pay big money to sign and promote new artists. In the 1990s, the majors spent roughly $300,000 to promote and market a typical new album16—money that couldn’t be recouped if the album flopped. And those costs increased in the next two decades. According to a 2014 report from the International Federation of the Phonographic Industry, major labels were then spending between $500,000 to $2,000,000 to “break” newly signed artists. Only 10–20 percent of such artists cover the costs—and, of course, only a few attain stardom. But those few stars make everything else possible. As the IFPI report put it, “it is the revenue generated by the comparatively few successful projects that enable record labels to continue to carry the risk on the investment across their rosters.”17 In this respect, the majors in all the creative industries operated like venture capitalists.

Dear Chairman: Boardroom Battles and the Rise of Shareholder Activism by Jeff Gramm

The best investing book of the year because of rich stories and history (also, the catalyst for my new podcast, as Jeff Gramm was my first guest).

Sadly, your ineptitude is not limited to your failure to communicate with bond and unit holders. A review of your record reveals years of value destruction and strategic blunders which have led us to dub you one of the most dangerous and incompetent executives in America. (I was amused to learn, in the course of our investigation, that at Cornell University there is an “Irik Sevin Scholarship.” One can only pity the poor student who suffers the indignity of attaching your name to his academic record.)

Shoe Dog: A Memoir by the Creator of Nike by Phil Knight

The best business book that I can remember.

You are remembered, he said, prophetically, for the rules you break.

Leaning back in my recliner each night, staring at the ceiling, I tried to settle myself. I told myself: Life is growth. You grow or you die.

The Wayfinders: Why Ancient Wisdom Matters in the Modern World (CBC Massey Lectures) by Wade Davis

A wonderful exploration of unique cultures through history and what they can teach us about how to live.

There is no beginning and end in Barasana thought, no sense of a linear progression of time, destiny, or fate. Theirs is a fractal world in which no event has a life of its own, and any number of ideas can coexist in parallel levels of perception and meaning. Scale succumbs to intention. Every object must be understood, as Stephen told me, at various levels of analysis. A rapid is an impediment to travel but also a house of the ancestors, with both a front and a back door. A stool is not a symbol of a mountain; it is in every sense an actual mountain, upon the summit of which sits the shaman.

Nobody Wants to Read Your Sh*t: Why That Is And What You Can Do About It by Steven Pressfield

I’ve given this book to more than 10 people, because it is so useful for writers.

Nobody wants to read your shit. What’s the answer? 1) Streamline your message. Focus it and pare it down to its simplest, clearest, easiest-to-understand form. 2) Make its expression fun. Or sexy or interesting or scary or informative. Make it so compelling that a person would have to be crazy NOT to read it. 3) Apply that to all forms of writing or art or commerce.

At Play in the Fields of the Lord by Peter Matthiessen

My favorite novel of the year: incredibly well written, with memorable setting and characters.

For men like himself the ends of the earth had this great allure: that one was never asked about a past or future but could live as freely as an animal, close to the gut, and day by day by day.

Capital Returns: Investing Through the Capital Cycle: A Money Manager’s Reports 2002-15 by Edward Chancellor

The second-best investing book of the year, and the most useful because it might change the way you think about your investing process.

Thus, the great commodity supercycle bears the hallmarks of a classic capital cycle: high prices boosting profitability, followed by rising investment and the arrival of new entrants, encouraged by overly optimistic demand forecasts; and the cycle turning once supply has increased and demand has disappointed.

Positioning: The Battle for Your Mind: The Battle for Your Mind by Al Ries, Jack Trout

A simple but perfect book on marketing.

To be successful today, you must touch base with reality. And the only reality that counts is what’s already in the prospect’s mind.


In a year that I watched my beautiful daughter enter the world, I was constantly reminded of the magic that is possible in our lives, available to all who open themselves up to it. I hope to enter 2017 with you openly: ready to learn, ready to shed ego, and ready to enjoy whatever may come!