There’s richness and complexity in the concepts you absorb through reading that you can’t get from listening to talks or having someone explain something to you. So I love to read. My personality and work have skewed my reading list towards the philosophical, historical, sciences, startups and venture capital. This isn’t an exhaustive list, but excluding the venture capital books which would be too specific, I think the books on this list can be interesting to most anyone who is interested in understanding how the world works and how to function better in it.
Books worth reading more than once:
Sapiens: A Brief History of Humankind by Yuval Noah Hariri: What a brilliant, honest account of the world we live in. He pushes no agenda but truly informs. It is not through an Eastern lens, a Western lens, an Israeli lens, an Arab lens, or any other lens, just reason by someone who sees outside their own prejudice and is willing to go against convention. My only disappointment is he came up with no logical answer as to why the subjugation of women has been so ubiquitous across the cultures and eras, despite his ability to come up with true answers to many other anthropological/sociological questions that have stumped entire departments/the news media. Throughout the book I went “that makes sense!” on his theses that directly conflict with popular consensus.
From Zero to One: Notes on Startups, Or How to Build The Future by Peter Thiel: This is a book from someone who truly thinks for himself, and imparts his wisdom clearly. He understands startups and human nature as it applies to modern business in the same way Yuval Noah Hariri understands human history. I’ve since voraciously been eating up everything Peter Thiel. Man is brilliant.
Stuff Matters by Mark Miodownik: I never thought I would audibly “ooh” and “aaah” alone at home from a book about common materials such as glass, plastic, and cement. Think of this book as your chemistry textbook come to life, without all the unnecessary detail and some added suspense. I have a much greater appreciation for materials science and the world around me now and I feel more competent when thinking about industrial technology trends.
#GIRLBOSS by Sophia Amoruso: It was really nice to read one of these startup/founder biographies that is 1. autobiographical, 2. by a woman, 3. well-written. She’s funny, light, anti-authority and I was able to see elements of my character and journey in hers which made it extra relatable.
Principles by Ray Dalio: Hedge fund billionaire and Bridgewater Associates founder shares his life and work principles and his personal story. It is well written, an easy read, and provides good principles to reference in determining or re-evaluating one’s own principles.
Angel Investing by David S. Rose: I still use this as a reference for evaluating early stage tech companies and we ordered these at WOMENA to give as welcome gifts to new members.
The Business of Venture Capital by Mahendra Ramsinghani: I use this as a reference now and again. Covers what you need to know about everything about the businesses of venture capital quite well. Equally useful for LPs as it is for new analysts and even startups if they want an empathetic leg up.
Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist by Brad Feld and Jason Mendelson: It delivers as promised — you will end up smarter than your lawyer and venture capitalist. I found that I knew more about deal structuring than my lawyer and understood my negotiating position well when looking at deals better than many of my co-investors (not you if you’re reading this). Highly recommend and still reference sometimes.
Books I read once and I’m glad I did:
Scarcity: Why Having Too Little Means So Much by Sendhil Mullainathan and Eldar Shafir: If you’re a rich person who wants to understand why poor people do all those gosh darn kooky things, or a person with scarce resources wanting to understand how you can make better decisions, I recommend this. I should preface though — this is not a self-help book, it is a book written by academics. You can turn it into a self help book if you can make logical inferences and relate it back to your own behavior, though.
Abundance: The Future Is Better Than You Think by Steven Kotler and Peter Diamandis: I’m a strong believer that our understanding of economic principles is deeply flawed. Economic principles as taught now ignore the rate of change accelerated by technological advancements, as well as human nature when faced with abundance, scarcity, and irrationality, and that history and likely the future is more defined by spikes than cycles. In short, it ignores the formula which appears rather clear to me for creating abundance. This book allows me to take my belief in abundance beyond the theoretical and provide concrete examples for a free, technology-focused, and competitive society.
The Short History of Nearly Everything by Bill Bryson: Sapiens begins at the beginning of human history and this book starts with the Big Bang. I enjoyed that he tells it in story form rather than as a boring science book. But I can’t help but be suspicious that he is putting forward hypotheses as accepted theories, which reeks of the same ignorance that made people think they knew all they needed to know to know the world is flat. I would have preferred if he said “we don’t know” more often. But it’s good to know what the scientific establishment is putting forth as truth in our era.
The Golden Tap: The Inside Story of Hyper-Funded Indian Startups by Kashyap Deorah: I had met Kashyap a couple times before and he said he was writing a book, so one day when browsing through Amazon I stumbled upon this I was like, “Cool!” and I read it. And I’m glad I did. For anyone who works in, invests in, starts up in emerging tech startup ecosystems, it is a highly informative read. Although India and MENA are extremely different, I gathered a lot from his mistakes and successes which can be used to make better decisions in the MENA region allow any VC who invests in emerging market ecosystems to adjust their assessment framework to the market they are in.
Homo Deus: A Brief History of Tomorrow by Yuval Noah Hariri: Sapiens: A Brief History of Humankind covers human history from the beginning of what we know to the present and A Brief History of Tomorrow addresses what the future of humanity may look like. Yuval Noah Hariri argues his points unbelievably well. I’d say he’s on the right track with most of the information. He starts by saying that humans will seek immortality, divinity, and bliss in the future [given basic needs are cared for because of abundance]. I found out he meditates two hours per day and spends one month per year away from society. I wonder if I would have the clarity that he does if I did that, too. It would be worth it, the guy is fucking smart.
The Everything Store: Jeff Bezos and the Age of Amazon by Brad Stone: Very well-written, entertaining, well-researched biography of Amazon and Jeff Bezos. It’s good to know what happened internally in Amazon and what kind of leadership it took to get Amazon to be the behemoth it was. I didn’t come away loving or hating Bezos. He is a doer, extremely rational, missionary, cutthroat, and smart as hell. I had a newfound respect for Amazon and a deep belief in its prospects after reading.
Hatching Twitter: A True Story of Money, Power, Friendship, and Betrayal by Nick Bilton: I enjoyed this, but not as much as The Everything Store. It is a much more melodramatic, Hollywood tale that seems to lack good sources at times, and maybe got filled with bullshit sometimes to make it spicy. Like when he talks about how one of the characters was feeling, i.e. “He slumped to the ground in regret, pondering his future” I immediately thought Really, were you there? Did he tell you how he felt? Especially since he by and large wasn’t granted interviews. In any case, it is an interesting story and is probably at least 70% true, so an entertaining way to learn about the origins and growth of Twitter… if taken with a grain of salt.
The Hard Thing About Hard Things by Ben Horowitz: Another gut-wrenching saga of founding that plays out over eight years and is told by the co-founder himself with great stories. I like this one because it is autobiographical so you get a different look at his company growth journey than that written by journalists. The only thing I wish was in there that wasn’t was more on co-founder dynamics and the decisions they made together. This is one of the most important aspects of company founding and he glossed completely over it — maybe because his co-founder in the story is also his co-founder for A16Z and it wouldn’t be appropriate, but I would have loved to have understood how they built a partnership that lasted 20 years and counting and has made it through many rough spots.
Dataclysm: Love, Sex, Race, and Identity — What Our Online Selves Tell Us About Our Offline Selves by Christian Rudder: It’s interesting how a writer’s personality shines through. Christian Rudder seems like a pretty jaded, cynical person, but because he is a good and smart person who saw a disappointing world in what he created with OKCupid. I say this even though this book is a book about data on sexual and romantic preferences from when he ran OkCupid. Fascinating, but it’s based on a blog from OKCupid’s early days and if you read that, you got the gist. He expands on some ideas, but didn’t do new research. In any case, very interesting data. For instance, when it comes to dating preferences, Americans are racist as hell and Brits almost aren’t at all. When it comes to choosing a partner, women tend to search for men of similar attractiveness to them, and rarely message men who are much better looking, while men, regardless of attractiveness, go for the most attractive women first. At least according to old OKCupid data. Who knows how a different UX would affect these.
The Age of Cryptocurrency: I couldn’t get through Blockchain Revolution — it was far more technical than I expected it to be for a mass market book on the topic — but The Age of Cryptocurrency ended up being what I was looking for. It was a great primer on the history of cryptos, ICOs, use cases for blockchain, and current innovations (current-ish — book is a couple years old). If you’re choosing between this and Blockchain Revolution, choose this one.
The Digital Doctor by Bob Wachter helped me understand the challenges facing tech adoption in the US healthcare system and thereby evaluate healthtech deals better.
Double Your Profits in 16 Months Or Less by Bob Fifer: This book written in 1994 was given to me by a VC friend. I met him in his office and they had a shelf of books that acts as a library. You can take any book so long as you bring it back and add another one to the library. I still owe him a book and haven’t returned this one yet. This book serves as a great reminder of how business used to work and allowed me to reflect on how differently venture capital-backed businesses operate and how modern society has changed business. It has some things that have lasted the test of time like cutting non-essential expenses and some that haven’t like one computer is enough for the office. I’d say 80% is still applicable to modern business. It’s an easy read, too. I also like author’s 80s/90s businessman persona seeping through the book. He self promotes in a way that was aggressive and alpha back then but now would be considered cheesy.
The Subtle Art of Not Giving A Fuck by Mark Manson: This is an easy read and he tells good stories to make his point and I agree with 80% of it. The title is misleading… it is much more about motivation and what you should give a fuck than not giving a fuck. I’d say this book is about living a purposeful life, and makes the point that if you live a purposeful life, you don’t give a fuck about stupid shit because you have something more powerful that drives you.
Quiet: The Power of Introverts in A World That Can’t Stop Talking by Susan Cain: I’ll start by saying I do not consider myself an introvert. I consider myself an extrovert who, when faced with a lack of smart people around me, becomes introverted because I’m deeply bored and I’m just uninterested in small talk, the mundane, and political correctness. I have appreciation for skill and knowledge rather than name-dropping and empty words. But I increasingly see a society where the loudest voice, not the smartest voice gets heard and was looking for an answer that doesn’t force socialization to be miserable for those who are brilliant…but quiet. While this book made good points about why introverts deserve more of society’s rewards, it did not give me the answer to how to actually incentivize that. Still looking, if anybody knows.
Brave New World by Aldous Huxley: A novel from the 20s or a glimpse into the future?
The Art of War by Sun Tzu: It’s not just a military strategy book, it gives tips on how to outsmart opponents and is foundational to modern corporate strategy.
Allen Carr’s Easy Way to Stop Smoking by Allen Carr: This book actually helped me stop smoking. I don’t know how it works but it does. Almost three years now.
It’s Not You: 27 Wrong Reasons You’re Single by Sara Eckel: This book is hilarious. And I read it at a time where my love life had been dead for a socially unacceptable period of time and I was seeking advice from people who give stupid reasons for singlehood. The book reminded me they are stupid reasons and helped me to take things in stride. Every woman, whether single or not, will relate and have a good laugh, though.
Mating in Captivity by Esther Perel: This book takes an honest look at monogamous relationships and acknowledges a problem that past religions, fairy tales, and porn fail to address: sex becomes boring in secure, long-term, monogamous relationships. We want distance, mystery, and thrills sexually, but to come home to a stable, loving home. And we’re too jealous and possessive for open relationships to work for most people. Biology screwed us on this one. Rock, meet hard place. She doesn’t provide an overarching solution or new philosophy on love and sex but at least faces the actual problem truthfully and provides some good tips to keep sex in a marriage exciting. There’s a lot of other really interesting stuff in there, too.
Books I read half of and got the gist of:
The Black Swan by Nassim Nicholas Taleb: Maybe this book has been talked up too much, and maybe it was groundbreaking when it first came out, but I didn’t get the hype. His writing style is erratic and tangential, which I assume makes him a great lunch date, but an irritating read. He spends a lot of time dissecting man’s unconscious biases without introducing new discoveries, and fails to make a connection to his primary thesis. In some places he draws connections that don’t make sense. But I agree with part of the core message— human history is defined by spikes not cycles, and disagree with the other part of the core message: He thinks our prediction models can’t predict these spikes accurately. I think we just need better models with better inputs.
Thinking Fast and Slow by Daniel Kahneman: We all do it and pretend we read the whole book. These books you really only need to read ¼–½ of to get the point, and only if you are an expert who wants minute detail do you need to proceed from there. Thinking Fast and Slow is one of these books. It takes an academic look on how thought patterns shape instinctual fast decisions in people. It’s a good book and makes a good point, but the second half is for psychologists.
How to Create A Mind by Ray Kurzweil: My main takeaway from this book is that the brain is a pattern storage and recognition system and patterns can come through the senses as images, smells, sounds, emotions, etc. It’s a good book but unless you’re a neuroscientist half is enough.
Crucial Conversations: Tools for Talking When Stakes Are High by Kerry Patterson and Joseph Grenny: I was reading it as a reference when I was having some really difficult conflict with someone I cared about. It was helpful at the time. This is a useful tool and I didn’t stop reading because I got bored or got everything I needed out of it, but because it’s better as the kind of book that you use as a reference when relevant, because you won’t retain the info without applying it.
The Four Hour Workweek by Tim Ferriss: The thesis of the book is that we have moved beyond the corporate slave life and the reader should harness technology to be their own boss. I think this book was probably quite seminal when it came out.
The Organized Mind: Thinking Straight in the Age of Information Overload by Daniel Levitin: It gives all sorts of solutions which I think are useful — but the problem is not people changing the way they organize their drawers, the problem is more fundamentally psychological and the author misses this. I’ll tell you what I have found to be the solution to information overload in a paragraph: 1. turn off all notifications on your phone and laptop, including messages, facebook, instagram, snapchat. You decide when you want to talk to people; they do not, 2. Write as much as you read, participate in dialogs. The fundamental issue with information is that it’s constantly an inflow with no response from you which results in a confused mess. This is probably because the brain needs to categorize, and you can only do this by summarizing what you’ve taken in and deciding what’s true and what’s not. Without this outflow of thought, or judgment call, information remains in line to be categorized, creating a gut. Energy in, energy out. 3. Finally, most importantly, learn to be alone. Learn to find validation internally. Social media and faux productivity will result in dispersion. Be quiet with yourself and be disciplined. That’s all.