To be clear: I publish this list every year not to #HumbleBrag or show off. In fact, I am kinda-sorta embarrassed that this list exposes many important works that I had not yet read. Don’t judge me.
Also, other than the “Top Ten” these are not necessarily recommendations, just a chronological log (though most were recommended to me somehow and I recommend most of them in turn, form your own opinion).
Given lockdowns, no travel etc. I read more than usual this year, yet this list would have been even longer had I not followed a curious rabbit down its hole and pursued some new and exciting projects that I never dreamed I might undertake. Also note a heavy emphasis this year on a) fiction, and b) books about writing. Deduce from that what you will; stay tuned … dum-dum dum.
2020 Top Ten
It was very, very hard for me to choose this year’s Top Ten. So, since I make the rules around here, there are thirteen in this year’s Top Ten. Sue me.
1. 7 Powers / Hamilton Helmer
“One of the best business books in history.” — Patrick O’Shaughnessy
“Everyone is trying to eat your lunch, and if you don’t read 7 Powers you’re going to die a lot sooner” — Reed Hastings (“you” = your company, it’s a business book, don’t panic)
More about this one in 2021… dum-dum-dum
2. Play Bigger / Al Ramadan, Dave Peterson, Christopher Lochhead, Kevin Maney
OK, so you’re read Zero to One and Crossing the Chasm, and you want to get your startup to one of Helmer’s 7 Powers. How do you get there? Play Bigger provides the Category Creation playbook. Also, I’ve gotten to know Dave Peterson and he is the nicest guy, ever.
3. The Nature of Technology / W. Brian Arthur
“Entrepreneurship in advanced technology, is not merely a matter of decision-making; it is a matter of imposing cognitive order on situations that are repeatedly ill-defined.” A must-read for anyone (operating or investing) in tech entrepreneurship.
4. Never Split the Difference / Chris Voss
Not your typical, brainless “how to negotiate” book. Lots of proven and actionable tactics from the US’ chief hostage negotiator.
5. Biased / Jennifer L. Eberhardt
Honestly, I read this one before “Black Lives Matter” grabbed headlines — I thought it would take me deeper into understanding behavioral economics-type biases. Some of that, but lots of important and informative discussion about racial bias. Dr. Eberhardt is a brilliant writer and academic with both moving first-hand accounts and scholarly explanations of how humans experience and confront bias.
6. The Power Broker / Robert A. Caro
Caro has dedicated his life to profiling just two men — LBJ, and before that, Robert Moses. Why would Caro do that? Read the books and find out. Possibly the best biographer of all time.
7. The Choice / Dr. Edith Eva Eger
Very Viktor Frankl (he makes a cameo) and, if possible, builds upon Man’s search for Meaning with its touching and inspiring account of overcoming life challenges (in her case, Nazi atrocity). Amazing insights and vignettes.
8. The Ride of a Lifetime / Robert Iger
I generally dislike autobiographies but this was fabulous. I loved the first-person accounts of some of the greatest (and non-consensus) business deals in entertainment history.
9. The Lessons of History / Will & Ariel Durant
A synopsis of their epic work. The best of history from the best of popular historians.
10. The Science of Storytelling / Will Storr
I dove (dived?) deep into storytelling and story structure this year, initially to understand how story structure relates to startup pitching. Then, rabbit, hole, etc…
BONUS: Great Fiction
I read so much great fiction this year.
11. Green Hills of Africa / Ernest Hemingway
If I would have written this it would’ve been a bland short story called “A Man Hunts Kudu.” The Old Man and the Sea would have been “Old Man Catches Fish,” etc. I can’t consume enough Hemingway and Vonnegut.
12. Galapagos / Kurt Vonnegut
Read any Vonnegut, and as much as you can. I binged on Vonnegut this year. I think I enjoyed Galapagos even better than Cat’s Cradle (already read Slaughterhouse Five), the others below are great too.
13. Foundation / Isaac Asimov
By this book, I mean the whole seven-book “Foundation” series. Epic.
Really took chances with Hemingway, Vonnegut and Asimov, huh? What can I say. They are considered masters for good reason.
Now, the rest, some really good ones in here:
Science, The World and Life in General
On Intelligence / Jeff Hawkins, Sandra Blakeslee
Essentialism / Greg McKeown
Farsighted / Steven Johnson
The Price of Tomorrow / Jeff Booth
Cooked / Michael Pollan (Anything by pollan is well done. See what I did there?)
Strong Fathers, Strong Daughters / Meg Meeker (I cannot recall how I stumbled upon this; you will enjoy it immensely if like me you have daughters, and also live in 1850 and are a religious fundamentalist who believes all seventeen year old boys are up to no good. Wait, maybe I do like this book … I don’t really recommend it, but people in glass houses shouldn’t throw stones. If you are not living in 1850 or a religious fundamentalist, maybe pop open two Cokes and listen to and discuss Billy Joel’s “Only the Good Die Young” with your teenage daughter, instead.)
Humankind / Rutger Bregman, Erica Moore, Elizabeth Manton (Along the way, debunks every single famous psychology experiment you leaned about in Psych 101. Hmmm …)
Humble Pi / Matt Parker
The Design of Everyday Things / Don Norman
User Friendly / Cliff Kuang, Robert Fabricant
The Signals Are Talking / Amy Webb
Seeing Around Corners: How to Spot Inflection Points in Business Before They Happen / Rita McGrath (I thought, since I am a venture capitalist and so often hear my colleagues claim to help their companies “see around corners,” that I should find out how. Unfortunately I still do not know how.)
How Will You Measure Your Life? / Clayton M. Christensen, James Allworth
The Open Society and Its Enemies / Karl Popper (Taleb draws upon Popper and Wittgenstein, so I explored both. How he derived tangible investment lessons from these two is super-impressive IMHO.)
History & Biography
Ghost Rider / Neil Peart (Rush is my favorite band, and Peart, who sadly died earlier this year, was the GDOAT, but this book is not about music. Rather, I would subtitle it “Grief and the Art of Motorcycle Maintenance.”)
Genius / James Gleick (Richard Feynman bio)
Open / Andre Agassi
The Thank-You Project / Nancy Davis Kho
The Score Takes Care of Itself / Bill Walsh, Steve Jamison, Craig Walsh (Many people think this book is amazing; I was very disappointed.)
Cable Cowboy / Mark Robichaux (John Malone bio)
The Complete Book of Five Rings / Miyamoto Musashi, Kenji Tokitsu (Or, “Ninja Mastery For Dummies”)
24 Hours in Ancient Rome: A Day in the Life of the People Who Lived There
/ Philip Matyszak (Not in Top Ten, but creative, enlightening and enjoyable)
The Alchemy of Air / Thomas Hager
The Lords of Creation / Fredrick Lewis Allen (IMHO incredibly well-written)
Sea Stories / William H. McRaven (meh, sorry)
The Anarchy / William Dalrymple (Not in Top Ten, but fascinating)
The Great Depression / James Ledbetter, Daniel B. Roth
The Great Crash of 1929 / John Kenneth Galbraith
Devil Take the Hindmost / Edward Chancellor
Homewreckers / Aaron Glantz
The Splendid and the Vile / Erik Larson
Boyd / Robert Coram
The Pioneers / David McCullough
The Wright Brothers / David McCullough (Must-read for entrepreneurs)
Wittgenstein / Hans Sluga
Acid for the Children / Flea (I had to put Flea next to Wittgenstein, just for fun)
The Man Who Solved the Market / Gregory Zuckerman (Bad news, fellow humans — before the robots harvest our organs, the quants will have all our money)
Investing, Business, Tech
Fooled by Randomness / Nassim Nicholas Taleb
The Checklist Manifesto / Atul Gawande
Start with Why / Simon Sinek (Very important, but you can get the gist in his fifteen-minute “Golden Circle” Youtube video)
The Infinite Game / Simon Sinek
Product-Led Growth / Wes Bush
Fortune’s Formula / William Poundstone
The Signal and the Noise / Nate Silver (Disappointing, because I wanted answers …)
Frictionless / Christiane Lemieux, Duff McDonald
Billion Dollar Burger / Chase Purdy (Yum! Well written. We need synthetic meat to solve climate change.)
The Art of the Start 2.0 / Guy Kawasaki
The Mystery of Capital / Hernando de Soto
The Rainforest / Victor W. Hwang, Greg Horowitt (A book about startup ecosystems, very close to my heart)
The Innovation Blind Spot / Ross Baird, Steve Case
Because Internet / Gretchen McCulloch
Books About Writing
Pity the Reader / Kurt Vonnegut, Suzanne McConnell
If This Isn’t Nice, What Is?: Advice for the Young / Kurt Vonnegut (I LOVE VONNEGUT!!!)
On Writing / Stephen King
Stein on Writing / Sol Stein
Consider This / Chuck Palahniuk
On Becoming a Novelist / John Gardner
The War of Art / Steven Pressfield (Title is great, book is good too)
Save the Cat! / Blake Snyder (Not in Top Ten, but worth reading if you want to understand the structure of pretty much any book or movie you’ve ever experienced)
Cat’s Cradle / Kurt Vonnegut (I LOVE VONNEGUT!!!)
Breakfast of Champions / Kurt Vonnegut
God Bless You, Mr. Rosewater / Kurt Vonnegut
Welcome to the Monkey House / Kurt Vonnegut
Mother Night / Kurt Vonnegut
The Sirens of Titan / Kurt Vonnegut
Tigerman / Nick Harkaway (John Le Carre’s son, I found out after. Not a spy novel.)
The Big Sleep / Raymond Chandler
I, Robot / Isaac Asimov
The Last Question / Isaac Asimov (OK, a long short story, but Audible charged me as if it were a book)
Prelude to Foundation / Isaac Asimov
Forward the Foundation / Isaac Asimov
Foundation and Empire / Isaac Asimov
Second Foundation / Isaac Asimov
Foundation’s Edge / Isaac Asimov
Foundation and Earth / Isaac Asimov
The Murder of Roger Ackroyd / Agatha Christie
The Mysterious Affair at Styles / Agatha Christie
The Chekhov Collection of Short Stories / Anton Chekhov
Startup / Doree Shafrir
The Unicorn Project / Gene Kim
The Bonfire of the Vanities / Tom Wolfe
Back to Blood / Tom Wolfe
The Screwtape Letters / C. S. Lewis
Paradise Lost / John Milton
Snow Crash / Neal Stephenson (the origin of the term “metaverse”)
The Goal / Eliyahu M. Goldratt, Jeff Cox (Not an incredibly well-written book, but famous for its use of fiction to teach an otherwise kinda dry concept, industrial manufacturing efficiency. Changed the trajectory of my 2020 … dum-dum-dum)
This Is How You Lose the Time War / Amal El-Mohtar, Max Gladstone
On the Road / Jack Kerouac (If reading Hemingway feels like looking at a painting, reading Kerouac is like listening to a vinyl jazz record. Another classic I can’t believe I never read.)
The Sea Wolf / Jack London