Jumpspeed Ventures Lending Library

The 102 Books I Read This Year

Ben Wiener
8 min readDec 31, 2020


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

Happy reading!