Books you should read if you want to succeed (updated for 2020)

These are the books that helped me the most and made me who I am today.
January 20, 2020

Reading is priceless. I present to you my favorite books, divided into 5 major categories, that allowed me to develop the tools necessary to achieve success, get a job at a FAANG company, and eventually retire at 30.

I'd say that while many techniques may be useful (to widely varying degrees), the most important things these books can do is change your beliefs. Good books will change/drastically improve your beliefs about yourself, what you/your business is capable of and also highlight limiting beliefs you've taken for granted (that can hurt you and your business).

Different books will impact you depending on where you are with your beliefs and culture, so a book someone may swear by could do nothing for you.

My key idea in this article is to show you books that actually changed my life the most and avoid recommending cliches like the Four Hour Work Week and Zero to One.

Entrepreneurship

What I tell people about business books:

  • There are no silver bullet answers.
  • They won't tell you exactly what to do.

But if you can't dedicate yourself to sitting down and reading and taking notes on at least one REALLY GOOD book... you probably won't be able to follow through on all the processes that businesses require.

Innovation and Entrepreneurship by Peter Drucker

I would add almost anything by Peter Drucker but in particular Innovation and Entrepreneurship — that's the book that most of the business authors read. And it's the book that actually gets into the details of what needs to happen to set yourself up for success and how to think about it.

Most people who are buying entrepreneur books don't have to be motivated to become an entrepreneur. They need to work. And the reason they're buying a book usually is for some direction. Entrepreneurship really doesn't need to have anything to do with disatisfaction at the lives that we lead. It has to do with understanding our abilities to solve problems for others, and helping us with tools to expand those abilities, and our ability to identify worthy problems to solve. Worthy problems that either create great social, or financial good.

If you seriously want to start a business, read this book.

  • It's not motivational.

  • It's not a bunch of success stories or some lucky guy taking you through all of his achievements.

  • It's what you actually need to know. And if you can't sit down and read a book like this, you probably don't have the drive to start a business.

If you like it, add Effective Executive to your list. Best management book I've ever read.

Unscripted by MJ Demarco

Unscripted is an excellent, excellent book, if you need help with fundamentally understanding how to actually go about becoming a millionaire.

Details about starting a business the right way, making sure its scalable. Very motivating and detailed. The whole idea makes it sound like some four-hour workweek bullshit, but it's not.

The premise might seem obvious, but 99% of people are completely ignoring it. It's a must read. This is coming from someone who is highly skeptical of business books.

PIMP by Iceberg Slim

I read this after seeing Dave Chapelle call it the Capitalist Manifesto, and he was spot on. I was able to use this book for an assignment in a graduate level human resources class I was taking.

It really just showed me how we're all 'pimped' in everyday life, or how pimps 'manage' their stable, the lines are pretty blurred to me now.

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Pimp: The Story of My Life Pimp: The Story of My Life 864 reviews

Warren Buffett's Management Secrets by Mary Buffett

There's a short book by Mary Buffett I came across called Warren Buffett's Management Secrets. Although I really admire him as an investor, I was blown away by his very simple, yet extremely effective leadership style.

From the few books I've read on management, this one boiled everything down into 4 or 5 core skills that no doubt got Warren Buffett where he is today. His track record of managing managers, in my opinion, is just as impressive, if not more so, than his actual investing skill.

Finance

Personal finance is an extremely important life skill to enjoy a comfortable life. You can become a millionaire on a meager salary or be broke on a very high salary. I'd strongly recommend reading books, sticking to budgets, and investing as best as you can.

If you're interested in takings some risks and trading stocks, take a look at Ed Thorpe, William O'Neil, and Alexander Elder. They are 3 of the greatest books ever written about trading, capturing the entire symphony of the markets.

One rule. Never, ever risk more than 2% net worth on a single trade. 1% if your trade parameters are met with frequency to merit more positions or are inconsistent in performance, like having a losing month or unexpected results.

There's no such thing as an edge minus uncertainty large enough to warrant a 15% risk position - it's by definition negative EV by Kelly Criterion and the definition of gambling. You should never put a 100k into crypto if your net worth is 1mil.

The Bogleheads' Guide to Investing Paperback by Taylor Larimore

Explains the mindset to become wealthy. Its mostly a slow and steady wins the race via frugality and investing strategy.

It goes over a lot of different scenarios and how to invest. Key points are tax advantages and diversity.

A Man for All Markets by Edward Thorp

Ed Thorpe is perhaps the greatest trading mathematician to ever live. Not only did he singlehandedly beat the casinos with card counting, but this MIT professor also revolutionized portfolio and risk management with his findings.

He has a net worth of 500mil, and he genuinely does not care about money. He is a true academic at heart and you can tell. He only made the money to quiet the naysayers. There are audio interviews with him that are pure gold

The New Trading for a Living by Alexander Elder

Elder Alexander is a comprehensive introduction to the realities of trading for a living. Designed to simplify advanced concepts to be understandable for non specialists, it examines how trading fits into your life, and how to structure your life around it.

It touches briefly upon every aspect of the entire symphony of the art, giving a complete overview of what to realistically expect. A magnum opus, as if A Brief History of Time.

How to Make Money in Stocks by William O'Neil

William O’Neil answers the burning question on every man’s mind. Which stock? He presents one of the best ways to pick a long term, safe, growth stock that will rise and rise for years to come.

A complete system, with complete reasoning and explanation. It's an excellent starting point for new stock market investors.

What Caused the Financial Crisis by Jeffrey Friedman

Same finance books get pimped all the time. I've probably read over 100 finance books.

Here's one I've never seen recommended ANYWHERE that is great: What Caused the Financial Crisis - Jeffrey Friedman. Read this book and thank me later. The single best book on the financial crisis.

To be recommended.

Personal development

Kant famously said "I freely admit that the remembrance of David Hume was the very thing that many years ago first interrupted my dogmatic slumber and gave a completely different direction to my researches in the field of speculative philosophy."

Things that, in my opinion, count as "enlightenment" are experiences which, in whatever personal way, wake you from some of your "dogmatic slumber". If you've experienced it, you'll recognize the label for it, but reading the label won't make you experience it.

Mastery by George Leonard

Imagine a book like 12 Rules for Life that wasn't treating the reader like a complete idiot and you've got Mastery.

It's a neat little book that teaches the reader about his five keys to mastery. Leonard relates it to his aikido practice, but it can be applied to learning any complicated skill. One of the lessons that stuck with me is that getting better at basically anything is not a linear path. As you improve at something, be it lifting, writing, or making music, you'll experience temporary dips where you seem to actively get worse at that thing. That was a weird, counter-intuitive but incredibly useful revelation to me at the time. Progress isn't entirely linear. That lesson got me through some tough times, and stopped me from giving up when it seemed like I was getting shittier at the things I tried.

Interestingly, near its start, Mastery does have a brief critique of American society and its excesses. Given that Mastery was published in the early 90s, right after the Cold War ended and third-way politics were in ascension, I can't say I'm surprised.

it's a pity that the self-help gurus and con artists monopolized the personal development genre because, for all its fucking bullshit, the gems of motivation and purpose in specific books (of which I've read an embarrassing amount) have really moved me in the right direction. Mastery is one example.

10% Happier by Dan Harris

It's his memoir about falling to demons, figuring out what they are, and overcoming them. It sounds more dramatic than it reads. The first line in the book is, "I wanted to call this book "The voice in my head is an asshole."" He's a skeptic of everything, and he is very relatable.

Priciples like, "respond, don't react" and realizing whether a negative thought/emotion is useful or not have been hugely influential on my life. I could not recommend this book highly enough. You will like Dan. He loves cats and is a very relatable guy.

The Prince by Nicolo Machiavelli

It's a very rough read so let me summarize it for the people who don't want to put in the time to read it:

  • Being generous is great, but if you are too generous, you will give everything away and will have nothing, and your generosity will end.

  • Keeping your word is great and will gain you respect. But if keeping your word means you will lose everything, then don't.

  • Having no vices is good. However if you have vices, you can compensate by being great. The people will forgive your vices because of your greatness.

  • There are two kinds of wisdom, and one folly. The wisdom that comes from your own mind, the wisdom of discerning wisdom in others. The folly is not having wisdom and not recognizing the wisdom in others.

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The Prince The Prince 530 reviews

Lost in the Cosmos by Walker Percy

In it, you'll find: a satirical look at the self-help craze, as well as a semiotic theory of the self and how it is that modern man is in such an existential crisis.

Percy is an engaging, witty writer, and while there are elements of the book I wasn't thrilled by (his provincial attitude toward homosexuality, for example), I found it incredibly insightful and genuinely profound. The final section of the book leaves me speechless every time I read it.

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Lost in the Cosmos Lost in the Cosmos 102 reviews

Unborn by Bankei Yotaku

The first half is basically just a summary of Bankei's life and how he attained enlightenment. While interesting, the best part is the second half, which consists of sermons that his students recorded.

It made me rethink my understanding of 'experience' and how it relates to what I consider my 'self'. Nobody has so clearly put to words the concepts set forth by Zen, Tao, the Buddha or what have you.

Positive Psychology in a Nutshell by Ilona Boniwell

Reading books, in general, is a great idea, but a lot of times it can be just another way to procrastinate. I just wanted to make sure you do not end up in this trap.

Knowledge is nothing without work. I have a very important book to recommend. It's not strictly motivational or directly related to the topics at hand, but it changed the way I look at certain things myself,

Critical Thinking

Books about critical thinking and technology always pushed me to get more creative with my endeavors.

  • Consider the media you take in. Do you only listen to one radio station, watch one news outlet, or value the reporting you receive on social media?

  • Listen - watch - value something different. For example, if you only listen to NPR, tune into AM talk radio. Conversely, if you only watch Fox News, tune into Colbert or late night tv to hear the other side.

  • Hear what others are saying. Oftentimes we can expand our critical thinking skills when we suspend our judgments and authentically listen to what others are saying.

  • Although being right and agreeing with others is not required, please consider your values and think for yourself.

  • Question your own thoughts and actions. Consider your values again, are you doing or saying something that is helpful to another person - or are you doing or saying something harmful? Are your thoughts and actions aligned?

Incerto Series by Nicholas Taleb

So, this is actually a series of 5 books: Fooled by Randomness, The Black Swan, Antifragile, Skin in the Game, and The Bed of Procrustes.

It made me skeptical about my own work and about if and when top-down theories are actually effective or useful.

Being skeptical about your ability to understand the phenomenon you’re studying (whether it’s apoptosis of cancer cells or click-through rates of search advertising campaigns) is critical to being an effective decision-making person and this series helped me to be humble in considering top-down approaches to the problems I’ve worked on.

Also it’s solid statistics.

Causality by Judea Pearl

Not sure if it's a 'must read' for everyone, but the most useful in-depth book I read through in the recent years was Judea Pearl's Causality. Really challenged me to think about probability distributions in a different way, I feel like I came out of it with some new ability to reason about things that I didn't really have before.

Pity the book wasn't more intuitive and direct though. The section on linear models and connections with the marketing literature was interesting, but I feel like the similarity with full nonparametric causal models and the slightly different rules you get with linear structural equation models was a little too much for me to fully wrap my head around.

I do a lot of A/B testing these days, and because of this book I now have a rigorous foundation for thinking about experiment sample size and statistical relevance of the results. I can't believe I used to fly blind with that stuff back in my early marketing days.

How to Create a Mind by Ray Kurzweil

I got overly excited at the prospect of iPhones and Internet connected laptops making hunger, pestilence, and CIA spooks obsolete. I sort of deep-fried myself in Kurzweil and felt like all was good.

Now, I'm not so sure. I still believe technology will play a deep and important role but, while I'm not convinced Kurzweil was wrong, I definitely think the solution is going to require more than just throwing bits and bytes at it. It's going to require new economic and political layers on top of those technologies as well. All very interesting.

Health

You need to do things slowly, and that your palette and tastes will change over time. I eat a super clean diet now, although used to eat the standard American diet in the past. I always struggled to stay eating healthy because I didn't enjoy the tastes and less sweetened food. It took me about nine months of slowly changing my foods for my palette to learn how to enjoy very earthy tastes without any sweeteners.

I drink a giant green smoothie with just water, greens cucumber and avocado in it every morning. A year ago it would have tasted disgusting but now it tastes so good, and best of all it satisfying. Unlike when I was overloading on carbs, food sure tasted good but I was never satisfied. People want easy fixes but to be truly content it takes a lot of dedication. Life feels such much better on the other side.

I Can Make You Thin by Paul McKenna

It is so much more than just to help you lose weight. It tackles self esteem, confidence, body image, self sabotage, how to confront and deal with emotions immediately rather than suppress them, and how to have a normal relationship with food. Losing weight is an inevitable side effect of it once you've fixed the body image and confidence issues which are far more life changing.

It literally changed my entire life completely and made me a far happier person in my own skin, happier with my life and the kind of confident person I never thought I'd be. It is absolutely not a diet book it barely touches on food, it is all about fixing your internal issues and bad wiring in your brain.

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I Can Make You Thin I Can Make You Thin 565 reviews

How Not to Die by Michael Greger M.D.

"How Not to Die" uses a traffic light system to rate foods. Almost all unprocessed plant foods are green light, meaning that they are health-promoting foods that can be eaten without limit, without negative effects.

Yellow light foods may have little or no positive effect on health and should only be enjoyed in moderation. I can't think of any off hand, but maybe white potatoes?

Red-light foods are harmful and should be avoided. Examples include ultra-processed foods and soda.

The recipes are gourmet level and the photography is just beautiful.

You won't need another book on food for a really, really long time.

Starting Strength by Mark Rippetoe

Starting Strength is good for beginners because it does four things:

  • Introduces the important compound lifts.
  • Encourages working on form over constantly adding weight.
  • Low volume/High intensity. This makes sure you're not destroying your joints but also making steady progress.
  • It's simple as fuck to follow.

A high volume/high intensity program is bad for beginners because beginners dont have the elbow/knee/forearm stability that most experienced lifters have. The high volume is going to destroy those parts of your body if you're not used to it.

Once you're confident in your lifts, Mark says to add whatever accessories you want, though you'll quickly learn not to overdo it. If you're bored or not progessing anymore, then obviously switch programs.

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Starting Strength Starting Strength 1,731 reviews
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