These are the most influential books in Silicon Valley
By: Alex Kepka
Tags: Venture Capital, Scaleup, Silicon Valley, Books, Startup

Silicon Valley attracts a colorful mix of characters, from physics PhDs to chess champions, from product designers to master advertisers. A recent study tried to quantify what the typical successful founder looks like, and it’s, surprisingly, a diverse 47-year-old without a computer science background — not the expected almost teenage and hoodied New England engineer.

This is hardly surprising as top founders and investors need to have a close relationship to reality. They need to think beyond the current cultural paradigm to what’s outside, what’s next and what’s timelessly true. To do that, the greats cultivate systems and lateral thinking and reading extensively and broadly supports that.

Stereotypes aside, the titans of technology do usually have one thing in common — they love to read.

I’ve seen a few books popping up again and again in interviews, on personal blogs, in Medium posts and as recommendations on Twitter. These books always seem to reveal hidden patterns of thinking and deep truths about human nature.

Most of the books in this list are nonfiction — and biographies dominate the pack by a mile. And if our famous founders and investors read fiction, then it’s almost invariably the science kind.

Poor Charlie’s Almanack: The Wit and Wisdom of Charles T. Munger

By Charlie Munger

Charlie Munger via Farnam Street

Recommended by:

Shane Parrish of Farnam Street fame

Patrick Collison, founder of Stripe

And Warren Buffett

“In my whole life, I have known no wise people (over a broad subject matter area) who didn’t read all the time — none, zero. You’d be amazed at how much Warren reads–and at how much I read. My children laugh at me. They think I’m a book with a couple of legs sticking out.”

― Charles T. Munger, Poor Charlie’s Almanack: The Wit and Wisdom of Charles T. Munger

Charlie Munger is one of the greatest business minds of our time. He is mainly known for being Vice Chairman of Berkshire Hathaway, the largest financial services company by revenue in the world, and as Warren Buffett’s right-hand man. He is so much more than that.

Munger is a polymath and an independent spirit. Through his studies in economics, history, biology, physics, and psychology, he’s narrowed in on what he calls beneficial mental models. These mental frameworks are often counterintuitive but always powerful lenses to look at the world. They have allowed Munger to understand complex situations and disentangle reality — while becoming a billionaire in the process.

Poor Charlie’s Almanack is a treasure trove of Munger’s writing, speeches, and quotes and shines a light on a lifetime full of cutting through the noise to get to the essence.

Surely you’re joking, Mr. Feynman

By Richard Feynman

Richard Feynman via Wikimedia Commons

Recommended by:

Fabrice Grinda

Noah Kagan, founder of AppSumo

Naval Ravikant, founder of AngelList

“You have no responsibility to live up to what other people think you ought to accomplish. I have no responsibility to be like they expect me to be. It’s their mistake, not my failing.”

― Richard Feynman, Surely You’re Joking, Mr. Feynman!

“Surely you’re joking, Mr. Feynman” is an autobiographical series of stories and anecdotes from the life of the Nobel prize winning physicist.

Richard Feynman was, similar to Charlie Munger, a renegade thinker. Not only that, he was a renegade character.

The running theme of his life was that he had no time for formality. He looked at life with piercing lucidity. He also deeply hated pretension, rituals and most of the blindly accepted norms of his time. Everything had to have a deep, scientific reason behind it, or Feynman wouldn’t buy it. From the way people drink tea to the naming of birds, Feynman opted out of established wisdom. He was also a lover of life — a notorious womanizer, a safecracker, he played the bongos, painted, and also contributed quite a lot to the science of biology.

His life is an endlessly fascinating example of how defying convention and thinking laterally can open up the world.

The Autobiography of Benjamin Franklin and Benjamin Franklin by Walter Isaacson

Recommended by:

Paul Graham, founder of Y Combinator

Elon Musk

“Those who would give up essential liberty to purchase a little temporary safety, deserve neither liberty nor safety.”

― Benjamin Franklin

Benjamin Franklin, one of the Founding Fathers of the United States, continues the list of Silicon Valley’s favorite polymaths. He didn’t just lay the foundation of a revolutionary state, he was also a prodigious scientist and inventor of a wide list of useful things like the lightning rod, swim fins, bifocals, the long arm the glass armonica, a library chair, the Franklin stove and sorely, but usefully — the catheter.

To be able to juggle all these world-changing activities, Franklin set up his own productivity system and describes it in detail, making his autobiography probably one of the first self-help books ever written.

Elon Musk’s take on the book: “Franklin was pretty awesome.”

The Evolution of Everything (and anything) by Matt Ridley

The Evolution of Everything via Souk

Recommended by:

Naval Ravikant, founder of AngelList

“Evolution is happening all around us. It is the best way of understanding how the human world changes, as well as the natural world. Change in human instructions, artifacts and habits is incremental, inexorable, and inevitable. It follows a narrative, going from one stage to the next; it creeps rather than jumps; it has its own spontaneous momentum, rather than being driven from outside; it has no goal or end in mind; and it largely happens by trial and error — a version of natural selection.”

— Matt Ridley, The Evolution of Everything

Evolution sounds like some sort of newt creature slowly crawled out of a pond, put on slacks and went to work on the 7:30 train. It’s an idea that’s been consigned to explaining how the occurrence of tiny mutations has had the power to shape life on earth and nothing more.

Matt Ridley begs to differ.

Through skillful analogy and a host of examples from every field imaginable, Ridley illustrates how the powers of evolution are at work in every system involving change and iteration. From the rules we’ve devised for human interaction to the intricacies of markets, evolution is at play. The book shows how incredibly complex systems are built from the bottom up, iteration by iteration, interaction by interaction, without the need for a designer. Ridley rebels against what he sees as an acceptance of a kind of creationism, of top-down thinking, this time not religious, but just as scientifically bankrupt.

AngelList founder and “philosophical influencer” Naval Ravikant is a huge Ridley fan “4 of my 20 favorite books are written by Matt Ridley.”

The Black Swan by Nassim Taleb

Photo by Teresa Pinho on Unsplash

Recommended by:

Fabrice Grinda

Matt Mullenweg, CEO of Automatic, Father of WordPress

“Rank beliefs not by their plausibility but by how much harm they might cause.”

― Nassim Nicholas Taleb, The Black Swan: The Impact of the Highly Improbable

“The Black Swan” is one of the most influential books on probability of our age. The main idea is that every aspect of our lives, from our history to technology to the appearance of life itself is heavily influenced by ‘Black Swan’ events. What is a Black Swan event in probability? It is s very low incidence but high impact event, like a devastating meteor (for the dinosaurs) or a devastating financial crash (for the humans).

The best analogy to describe this phenomenon in the book is the “Turkey fallacy”. If a turkey thinks probabilistically about its survival chances close to Thanksgiving and looks at historical data, it will observe that in 100% of the days leading up to Thanksgiving it has not died once, and so the probability is outstanding that he’ll be alright on Thanksgiving. The “unknown unknowns”, the information that remains hidden from the bird, have made sure that the Turkey becomes the victim of a tragic Black Swan event. Normal probabilistic thinking breaks down around these high-impact, low-frequency events.

Sapiens by Yuval Noah Harari

Sapiens via Amazon

Recommended by:

Naval Ravikant Bill Gates

Mark Zuckerberg

“History is something that very few people have been doing while everyone else was plowing fields and carrying water buckets.”

― Yuval Noah Harari, Sapiens: A Brief History of Humankind

This is a history of everything, at least in how it relates to human beings — our success, our cultures, and our civilizations. Few other books are so ambitious in their scope and even fewer succeed to make a case as compelling as Sapiens by Yuval Harari.

One of the main arguments of the book is that the killer app in the survival and flourishing of homo sapiens was the discovery of stories. They allowed us to weave bonds of cooperation between disparate tribes, trade, go to war and construct elaborate religious and mythological connections between people. Harari has a series of controversial takes on historical developments, peppered with a bit of romanticism for hunter-gatherer days, but, somehow, every tangent he explores is a gem of lateral thinking and boundless intellectual creativity.

Meditations by Marcus Aurelius

Meditations via Wikimedia Commons

Recommended by:

Kevin Rose, founder of Digg

Ryan Holiday, ex. CMO American Apparel, author

Naval Ravikant

“You have power over your mind — not outside events. Realize this, and you will find strength.”

― Marcus Aurelius, Meditations

This book is the diary of Roman emperor Marcus Aurelius and contains his personal thoughts on living a good life. It was never intended to be published, but somehow became one of the most important reference works of Stoic thought. Constantly looking to optimize, the tech giants in the Valley have seized Stoicism, an ancient philosophical practice, which some are calling “an operating system for your mind”.

Marcus Aurelius chronicles a life of discipline, of self-control, of taming one’s desires and of avoiding the traps of luxury and the ego. A life well lived for the Stoics is a life where the cultivation of virtues is more important than the pursuit of happiness or pleasure. Happiness for the Stoics was superseded by the idea of eudaimonia, of being in order with the world and at peace as the result of right action. Happiness, therefore, is merely a coincidence of a life well lived — not the goal.

Snow Crash by Neal Stephenson

Snow Crash via Amazon UK

Recommended by:

Reid Hoffman, founder of LinkedIn

Naval Ravikant

“Ninety-nine percent of everything that goes on in most Christian churches has nothing whatsoever to do with the actual religion. Intelligent people all notice this sooner or later, and they conclude that the entire one hundred percent is bullshit, which is why atheism is connected with being intelligent in people’s minds.”

― Neal Stephenson, Snow Crash

Now a classic of the cyberpunk genre, “Snow Crash” is set in a part utopian, part dystopian future, depending on how much you like anarcho-capitalism. Microstates ruled by corporations are the new form of government and a computer virus is literally killing programmers. Paced like a comic book, this light-hearted sci-fi story is a love it or completely-miss-the-point-of-it kind of novel.

This book is part of Silicon Valley lore, as it was an obsession of LinkedIn founder Reid Hoffman when it came out in 1992, according to his friend and PayPal founder Peter Thiel. The internet wasn’t anything close to what has become and social media was non-existent, but the book planted the seed of a sprawling social network in Hoffman’s mind. An idea that Hoffman turned into SocialNet in 1999, a flop, but the company set the stage for his 2002 hit — LinkedIn.

Thinking in Bets by Annie Duke

Annie Duke via Wikimedia Commons

Recommended by:

Mark Andreessen, co-founder of Netscape

“In most of our decisions, we are not betting against another person. Rather, we are betting against all the future versions of ourselves that we are not choosing.”

― Annie Duke, Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts

Annie Duke is an ex-poker champion turned probability populariser. “Thinking in bets” is the culmination of her knowledge in making decisions under uncertainty, and she translates this wisdom from the world of high stakes poker into the world of investing.

Mark Andreessen describes this one as a “compact guide to probabilistic domains like poker, or venture capital. Recommend for people operating in the real world.”

Zero to One: Notes on Startups, or How to Build the Future by Peter Thiel

Photo by Oscar Nilsson on Unsplash

Recommended by:

Mark Andreessen, co-founder of Netscape

Luis Von Ahn, co-founder of Duolingo

Matt Mullenweg, CEO of Automatic, Father of WordPress

“Zero to One moments in business happens only once. The next Bill Gates will not build an operating system. The next Larry Page or Sergey Brin won’t make a search engine. And the next Mark Zuckerberg won’t create a social network.”

Peter Thiel, Zero to One: Notes on Startups, or How to Build the Future

Written by PayPal co-founder, venture capitalist and straight talker Peter Thiel, this book does not pull any punches. It is the synthesis of decades of experience and astronomical success in Silicon Valley. The book condenses what Thiel has learned about what it takes to build your own unicorn.

Thiel argues that not only is a monopoly a good thing, but it is also the right target for a company desiring to revolutionize an industry. The rest of the book is populated with Thiel’s unique and often controversial ideas about what it takes to disrupt a market. Profoundly libertarian, Thiel throws shade at hipsters and “unaligned lab drones” alike, so if you’re looking for a kumbaya guide to building a business, look elsewhere. Thiel is that steely-eyed guy aggressively quoting Nietzsche at a party, not Steve Wozniak.

What are some of your favorite, course-altering & life-changing books?