Naturally, there are the usual suspects: Think and Grow Rich, Rich Dad Poor Dad, The Millionaire Next Door; however at this point, if someone hasn’t told you to read Stephen Covey’s The 7 Habits of Highly Effective People or Tim Ferriss’s Four Hour Work Week, then I can’t help you (or maybe I just did).

Entrepreneur reading book and drinking fresh coffee

Rather than add to the volume of these already touted books and add to their sales on Amazon, or let’s be honest their downloads on Blinkist, this article will focus on slightly different material. Each book highlights a different area of life that we all need to master: business, marketing, leadership, negotiation, the works. Often, we get siloed in our fields. Artists think like artists, programmers like programmers, and we never learn how to blend mediums.

While we hold the ideal of the Renaissance Man in reverence, we often fail to strive for the ideal. The below books are meant to help you bolster your stats and help build a better business.

The 48 Laws of Power

Robert Greene

“Do not leave your reputation to chance or gossip; it is your life’s artwork, and you must craft it, hone it, and display it with the care of an artist.”  ― Robert Greene, The 48 Laws of Power

If there is one book that every hustler should read it is Robert Greene’s The 48 Laws of Power. Whether you’re an intern starting out on a summer gig or a CEO looking to build their empire, Greene’s book is a collection of timeless wisdom gathered from emperors, warlords, and businessmen. Filled with useful quotes and distilled anecdotes, this book is practically a user’s manual for how to make it in any business.

Green wrote the book after working in Hollywood and taking notes on how agents and producers maneuvered behind closed doors. Similar to Niccolo Macheovelli’s The Prince (another must read) this is a useful tool to learn from, be it simply to know what to look for from a sociopath.

While Green’s other books such as Mastery, The 33 Strategies of War, and Seduction could also be put on this list in their own right, it is Power that contains the most useful knowledge of them all. With tips like “Never outshine the master,” and, “Say less than necessary,” this book is like the wise grandfather we never had.

It should be noted that much of this knowledge could be considered to be tools of the Sith, or at minimum will not gain you many favors; however, these are the methods employed by hundreds of powerful men in politics, entertainment, and Wall Street. Therefore, if you’re going to play in the arena, you better damn well know the rules of the game.


Robert McKee

“When we want mood experiences, we go to concerts or museums. When we want meaningful emotional experience, we go to the storyteller.” ― Robert McKee, Story: Substance, Structure, Style, and the Principles of Screenwriting

This is the bible for screenwriting. While Save the Cat, The Art of Dramatic Writing, and Syd Field’s Screenplay are all essential reads for wannabe writers, Robert McKee’s book is the most useful outside of industry.

Every entrepreneur understands brand and the importance of public image; however, every product comes down to one thing: story. People buy ideas not things. As Henry Ford said, “If I had asked people what they wanted, they would have said faster horses.”

Perhaps more than any country in the world Americans love movies. Our number one export is culture. From the glory days, the muscled men of the 80s, to the Marvel Cinematic Universe, the world loves stories. The beauty of McKee’s books is that it extolls the quintessential structure of how to build a screenplay. All stories follow a narrative. Whether it is Joseph Campbell’s monomyth or a stranger walking into town, everyone loves a good story.

Would bourbon be as popular today if it wasn’t for the stories of moonshiners, prohibition, and the men who carried the torch? Would Apple be the monster it is today without Steve Jobs creating an identity diametrically opposed to its competition? Rather than reading another book on marketing or another non-fiction diatribe on branding, dig your teeth into how movie makers think about crafting the script, and learn how you can literally create the arc of your business.

The Obstacle is the Way

Ryan Holiday

“The essence of Stoic philosophy is distilled into three disciplines: Perception, Action, Will. How we think about things, what we do about them, and how we accept or endure that which we cannot change.” — Ryan Holiday, The Obstacle is the Way

Every leader needs a point of view. Character is power. And while we all wish we had summers learning the lessons of life from the village elder, we are often left to become the men we wish to be.

Primarily based on the writings of Roman Emperor Marcus Aurelius, Ryan Holliday takes the lessons he has learned from an ancient tradition, Stoicism, and passes them on to a contemporary audience. With his companion book Ego is the Enemy, Holiday gives readers a deep dive into this ancient Greek and Roman way of living.

Obstacles provide opportunity for growth. Or in the words of stoic philosophers, “What blocks the path becomes the path.” The challenges we face in life and in business are not a nuisance they are the reason we exist. There is a great moniker for finding a new business, “Look for duct tape.” Where are the problems? What can be fixed? Done better? Where are others failing? What needs are not being met?

Michael Jordan had to learn how to beat the Pistons. Tom Brady was not given five Lombardi trophies. Stephen King faces the same blank page as every writer. The timeless wisdom passed along in this book helps change the frame of reference for all leaders.

Deep Work

Cal Newport

“If you don’t produce, you won’t thrive—no matter how skilled or talented you are.” ― Cal Newport, Deep Work: Rules for Focused Success in a Distracted World

 Distraction is the death of creativity. In the modern world companies are constantly vying for our attention. Social media wants to hook us with sensational news and rage bait. The world of click bait offers juicy, more intriguing headlines than we can possibly imagine. Newer, better documentaries are put out every week on Netflix and Amazon just as the latest, better looking video game is released by Square Enix.

The modern man faces more distractions today than anyone who has come before him. Every time we look at our screen there are thousands of programmers and investors looking back at us, trying to figure out how they can turn us into Pavlov’s dog.

Newport’s book lays out the value of discarding “multitasking” for more meaningful creation. We’ve created a distracted life. We believe handling things like email or checking our updates or the latest headline is productive, however, at the end of each day what have we really accomplished?

By setting strict time limits to work and focusing solely on one task, we get things done. Human beings are not machines that can constantly run. We may wish we could always be on, however, we need breaks. We do not, on the other hand, need breaks every five minutes to check our Instagram.

Perhaps the most useful tool in the book is it’s explanation of “The 4DX Framework.” Similar to the Eisenhower Matrix of urgent v. important, the 4DX Framework asks:

  1. What is the most important thing?
  2. Act on what you can measure
  3. Keep score
  4. Be accountable

The best system, not mentioned in the book, to apply this is Jerry Seinfeld’s method for writing jokes. Before he became the creator of the greatest sitcom of all-time, Seinfeld had a simple rule for writing material: everyday he wrote one joke. Next to his door he kept a calendar. On the days he wrote a joke he would draw a red “X” through the box. On the days he didn’t write a joke, he wrote nothing. Thus, he could literally see his progress and whether the chain was broken or not.

Do the work. Eliminate distractions. Focus on keeping the chain going.

The War of Art

Stephen Pressfield

“Are you paralyzed with fear? That’s a good sign. Fear is good. Like self-doubt, fear is an indicator.
― Steven Pressfield, The War of Art: Break Through the Blocks & Win Your Inner Creative Battles

Stephen Pressfield could have an entire list dedicated to his books alone. Each book is a literal goldmine for useful tips and tricks from Turning Pro to Nobody Wants to Read Your Sh*t, Pressfield has a practical and actionable guide for creating.

The War of Art is perhaps Pressfield’s most successful and most well-known work of nonfiction. Pressfield was a writer long before he was ever paid a dime to write. The interesting thing about Pressfield’s book is that the challenges faced by artists everywhere are the exact same challenges entrepreneurs face. Labeling it “the resistance” Pressfield dives into ways to combat those feelings of self-doubt, worthlessness, overthinking, and the mother of them all: fear.

The negative self-talk we berate ourselves with is crippling. Is this novel good enough? Will this company ever get off the ground? How will I ever sell this product? These are the trappings of the amateur. In order to combat them we must accept their existence and turn pro. Turning pro is Pressfield’s answer for meeting the challenge of the resistance. The professional shows up everyday. It is not a calling, it’s a hustle. We do not act when motivated, we show up again and again. We put in the work.

As with artists, entrepreneurs understand this struggle as well. Any creative endeavor be it a new company or a new script involves experience, dedication, hard work, grit, courage, and the ability to follow through. We understand that we are our own worst enemy.

In sports, athletes talk about being their “hardest critic,” however, they inevitably have an enemy at the gate. Michael Jordan had Bird, Magic, and Isiah to overcome as well as Barkley, Malone, and Ewing. And while businessmen like Elon Musk or Peter Theil have their adversaries and their obstacles, when starting a company from the ground up, the first thing we must learn to conquer is ourselves.

The Art of Learning

Josh Waitzkin

“Growth comes at the point of resistance.” — Josh Waitzkin

Waitzkin is a master learner. A child chess prodigy who was the inspiration for the movie Searching for Bobby Fischer, Waitzkin later become a Tai Chi Push hands world champion as well as a black belt in Jiu-Jitsu. However, the focus of Waitzkin’s life and the thing he prides himself on the most is learning how to learn.

Fundamentals are the building blocks of mastery. Every baseball coach and offensive line coach has been screaming this for years, and yet, here it is again from a chess master. This is an essential read for anyone who is interested in optimizing their life. To become great at anything we must learn how to learn. This meta-learning should be taught to us all at a young age, however, it’s not.

His understanding of the mental game of chess has led him to adapt those lessons to high performance in other fields. While many people spend a lifetime climbing the mountain of one field, Waitzkin has move on to many others. In one of the famous stories of the book, Waitzkin talks about the typical training for a young chess player. How they learn openings, attacks, and strategies. They are asked to memorize games and hold them in their heads.

His training began more simply with a king and a pawn. Understand the basics so that they become second nature. Learn how to learn so that there is no door closed to you.

Never Split the Difference

Chris Voss

“Conflict brings out truth, creativity, and resolution.” ― Chris Voss, Never Split the Difference: Negotiating As If Your Life Depended On It

In life you don’t get what you deserve. You get what you negotiate.

F.B.I negotiator Chris Voss breaks down how to be a better negotiator. He tears apart wisdom that has been passed down through the years like, “Getting to Yes,” and offers practical, more sound advice.

For example, how may times have we been told that we must get people to agree with us to get what we want? Yet, as Voss frames it, a “No” sets parameters. We now know our limits and we make the person we are talking with feel in control. We have now broken the cardinal rule of negotiation by getting to a disagreement, but in conflict growth.

Whether it’s buying a car, selling on Ebay, or handling a multimillion dollar deal, at some point we all have to negotiate. We negotiate over salaries, verdicts, relationships, and drinks. This essential life skill stands at the center of our everyday lives, and yet, we are never given a manual for how to handle it.

Voss lays out his methods for hostage negotiation and how it can be applied to everyday life. With tips like using “How” questions to make the conversation a mutual problem in which the target becomes the hero, to learning to use “anchors” to subconsciously control the terms of the deal, Voss’s wisdom is essential to anyone starting, running, or selling a business.

We all think negotiation is about smooth talking, NLP, Jedi mind tricks; however, the reality is much simpler. They key to being a good negotiator is being a good listener. As Stephen Covey would say, “To be interesting you have to be interested.”

Good actors are great listeners. The best improv comics in the world listen better than anyone else in the world. Mirroring, asking questions, and focusing all your attention on the subject at hand is the most important thing we can all do to have better, deeper conversations with our friends and colleagues. Even if it is a debate.

Your Brain at Work

David Rock

“A study done at the University of London found that constant emailing and text-messaging reduces mental capability by an average of ten points on an IQ test. It was five points for women, and fifteen points for men. This effect is similar to missing a night’s sleep. For men, it’s around three times more than the effect of smoking cannabis.” ― David Rock, Your Brain at Work

Ryan Holliday’s book gave us a way to frame our mind. Josh Waitzkin’s book gave us a framework to learn. Chris Voss’s work teaches us how to navigate living on our own terms. Well, David Rock’s book teaches us how our brain works.

This is not wu-wu science or a weekend retreat, but the fundamental patters about how our brain takes in, uses, and stores information. Whether we are creating, building, learning, or working, all our lives would be better if we understand how to better grease the wheel.

Perhaps there is no greater take away from Rock’s work than understanding brain waves. We’ve all heard of sleep cycles and how we move through the night in various states of restfulness. Well, this process does not end when our eyes open. Throughout the day we move through various stages of creativity and productivity based on our own circadian rhythms. Meaning that 2 p.m. coffee was not just about a pick-me-up from that Chipotle lunch, but a reprieve from a dip in your natural rhythm.

The better we understand how we work, the more useful we can be in our lives. This is a nuts and bolts look at how to optimize your day and a better way of living from your brain out.

Have any other business books that hustlers needs to read? Let us know down in the comments.

This article originally published on GREY Journal.