Favorite Books

I always appreciate when people share their favorite books with me. Ryan Holiday’s blog and e-mails in particular have provided some fantastic book recommendations. Additionally, Michael Fogus’ and Christina Cacioppo’s blogs inspired me to keep track of books I’ve finished over the years. I figured I’d do the same here. In no particular order, (because trying to rate a book is akin to trying to rate a poem, per Dead Poets Society) here are the books I’ve most enjoyed.

I also have a spreadsheet with every book I’ve read since 2013 and plan to read.

My favorites:

Buffett: The Making of an American Capitalist, Roger Lowenstein - I’ve spent a lot of long walks listening to Buffett and Munger on Berkshire Hathaway calls. No matter the year, the principles are consistent and simple. Find situations where the incentives make sense, managers have a track record of allocating capital well, you understand the few key factors that drive outcomes and are committed to staying the course for years without looking to others for mark to markets. I think this advice goes far beyond investing and to me help explain in Lowenstein’s book how Buffett built Berkshire. He didn’t live where other investors lived, didn’t buy the same stocks, didn’t use the same techniques. In a world where advice is everywhere, Buffett to me is a reminder that there is no one course to finding your life’s passion and that first principle’s thinking may lead you to surprising conclusions.
The Art of Learning, Josh Waitzkin - No book has shook my reality more and encouraged me to make changes in my own life. Waitzkin is the rare dual-sport athlete who, after winning nearly every conceivable junior chess award and rising to International Master, retired and became world champion in an entirely different sport which he had no previous experience in (Tai Chi Push Hands). This book is not so much how as it is an exploration of why reaching optimal states and deep learning matter. A wonderful nugget from this one: Jim Harbaugh is a huge Waitzkin fan and slips chess every once in a while into NFL banter.
The War of Art, Steven Pressfield - A short read that for me was worth the several hour investment many times over. Seth Godin raved about War of Art on The Tim Ferriss show, which is how I originally heard about it. This book is 1) a call to action to work on important things and 2) a guide to how to defeat all the distractions that would prevent us from working on those things.
Surely You’re Joking, Mr. Feynman!, Richard Feynman - This title is tongue-in-cheek accurate, as some of the anecdotes in this book are so ridiculous they border on seeming made up (it’s actually a quote from a woman at a Princeton tea party commenting on when Feynman asked for cream and lemon in his tea). Feynman holds court on his adventures cracking safes, playing the bongos , painting and selling risque art, arguing with the best scientists of his day and so much more. The experience of reading this book is like listening to an incredible storyteller at a bar while getting the benefit of thought-provoking insights on science and human nature from a Nobel prize winner. Avoid reading on airplanes - too many laugh-out-loud moments.
The Soul of a New Machine, Tracy Kidder - Kidder won the Pulitzer in 1981 for this book and it’s a truly incredible story. Kidder has more or less full access to all members of a team of engineers and managers at Data General as they develop a new computer. The sheer complexity of the task at hand is both overwhelming and beautiful. Kidder has written a long-lasting testament to engineers’ ability to cope with unique problems.
How Life Imitates Chess, Garry Kasparov - worth it just to read the section on Kasparov’s five month duel with Karpov in 1984. Consider that for a second - two human beings played chess at the most elite level possible over five months (spanning 48 games). That’s a longer time period than the entire playoffs for all the major sports. Moreover, Kasparov discussing (i) the experience of playing Deep Blue and (ii) facing the world in an online match over four months are particular treats. I really feel Gary Kasparov’s contributions to chess are equivalent to Donald Knuth in computer science. Both have contributed so much to the world and put their contributions in an understandable form.
Hackers and Painters, Paul Graham - significantly more than entertaining essays on technology. Paul Graham’s thoughts on education, politics / religion, growing up (this essay on nerds is one of my favorites), etc. all represent a significant break from the norm. Also, the footnotes are wildly entertaining. **While not in the book, Maker’s Schedule, Manager’s Schedule is another great one from Paul Graham.
Extra Lives: Why Video Games Matter, Tom Bissel - prior to this collection of essays, I had read nothing reaching this level of eloquence on the sensory experience of playing video games. And it would be enough if Bissel just waxed poetic on playing - he goes out into the field and interviews all types of game-makers, talking about the decisions surrounding the design process, the future of the industry and the impact of games on the mind.
Benjamin Franklin: An American Life, Walter Isaacson I read this one after hearing Elon Musk cite it as a book that impacted him in an interview. Musk has said that what he admires about Franklin is that “he just thought about what are the problems that need to get solved and worked on those”.

Indeed, it’s really a weird wrinkle of history that one of history’s greatest scientists was called upon to play an integral role during the American Revolution. The question of American independence was one Franklin initially did not see as pressing, and his ability to shift gears accordingly and play the most crucial of parts in 1776 is intimately detailed by Isaacson.
The Education of a Coach, David Halberstam Yes, yes, I know. Spygate. It’s difficult for most NFL fans to warm up to Belichick unless, like me, you hail from Boston, MA. Know, however, that this biography was authored by the late David Halberstam, who is undoubtedly the greatest sports journalist of all time. Moreover, Belichick is a fascinating character whose work ethic (as shown in this biography) is incredible. I highly recommend in combination with A Football Life, the NFL Films documentary on him.
Damn Lucky: One Man’s Courage During the Bloodiest Campaign in Aviation History, Kevin Maurer John Luckadoo flew 25 bomber aircraft missions in 1943-1944 when most pilots during that time did not survive ten. I couldn’t put this one down as it has the unbelievalable action sequences of a real life Top Gun II mixed with Maurer’s incredibly detailed writing about Luckadoo’s life and WWII. Bomber pilots during this time had to face extreme German anti-aircraft fire (called flak) and German fighters hounding them. The story is told from the bomber pilot perspective; B-17 “flying fortress” aircraft had 10 people flying in them and dropped 500lb bombs on industrial and other Nazi Germany targets that helped swing the outcome of the war. Many of these missions resulted in heavy losses, including one over Munster where of the 13 aircraft that left, only one returned. Luckadoo and the 100th Bomb Group are heroes and this book is a remarkable retelling of their story.