The Best Books for Building a Startup Career

When I landed my first startup job, I felt like I knew nothing. Actually, some days I felt like I knew less than nothing.

I was nineteen years old, and my previous working experience consisted of tutoring homeschooled kids and picking apples for a living. I had no idea what a quarter was, let alone a KPI. I was excited and I was hungry and I had no clue what I was doing.

I realized (much later) that it wasn’t just me. One of the most frustrating things when you’re starting your career is all the stuff you don’t know. You’re young, and you’re excited, and you have all the time in the world — all advantages — but there are some pretty big disadvantages that come with the territory. The biggest two are a lack of experience and a lack of knowledge. The latter, in part, is a symptom of the former.

When you don’t have a lot of knowledge yet, one of the best ways you can compensate for it is by reading.

Here’s the thing — to be an effective player in the startup world, there’s a lot you have to be good at. Some of the most important:

  • understanding how startups work in the first place (pretty obvious, but as I quickly discovered, it’s a whole different world)
  • knowing how to articulate and sell ideas really, really well
  • being super adaptable, on the turn of a dime
  • understanding how to test ideas, learn from the results, and redirect course accordingly
  • being resilient, even when it seems like everything’s going wrong
  • thinking creatively about solving problems
  • thinking innovatively, and being able to come up with ideas no one’s ever tried before

Relying on experience as a source of knowledge limits you to a chronological progression of growth — one that’s constrained by how quickly you can accumulate experiences. It might take years to encounter enough problems and come up with enough solutions to really learn how to think innovatively and start to pitch ideas that have an impact.

When you don’t have experience, borrow someone else’s. The fastest way to level up is to read — a lot.

When you read, you get to immerse yourself in the thoughts and ideas of people far smarter than you. It’s the equivalent of landing a dinner with one of your professional heroes, and getting to ask them questions all night, and then getting lucky enough to have them accept your invite to go get drinks once dinner is over, at which point they’re answering questions you didn’t even know you had.

And even once you have leveled up, keep reading. If you rely solely on your own experiences and perspectives, your growth trajectory is limited by the linear and chronological pace of your own development. If you use books as a window into other people’s experiences, you blow your knowledge-acquisition potential wide open.

The following is a collection of some of the books that have been most impactful to me on my own journey as a professional, and the ones I’d most highly recommend to others trying to level up their startup game.

The Essential Classics:

Zero to One by Peter Thiel

This is the classic playbook of the startup world. The subtitle says it all: “notes on startups, or how to build the future.” Thiel boils down the lessons he learned through starting PayPal and Palantir into 12 chapters of pure wisdom. I reread it on the regular.

This book will help you understand how startups work, and it will give you a window into what it means to think innovatively — one of the most important skills to have if you want to really crush it in the startup space.

Thiel talks about:

  • What it means to go from zero to one. Zero to One means going from nothing to something (inventing something that has never existed before, like the Wright brothers building the first airplane). One to N means innovating on something that already exists (like Boeing releasing the 737 MAX). The best companies always want to start from zero, and create something entirely new.
  • How the paradigm around innovation and growth has changed over time, and what that means for business.
  • How all the most successful people know secrets, and build their companies around the secrets they’ve discovered about how the world works. There are lots of secrets left to be discovered in the world, and our job is to find them.
  • His philosophy around hiring and building great teams
  • The importance of coming up with ideas no one has ever thought of before (and what this looks like in practice)
  • The importance of thinking about the best businesses as monopolies.

Niche Down by Christopher Lochhead

This book starts with the idea of thinking innovatively/finding your monopoly and takes it one step further.

Niching Down means finding your niche — the smaller, the better — and then completely dominating it. That’s how all great companies are built. Lochhead explores great companies that have found their niches, and breaks down what makes each one so impressive.

It’s a phenomenal book that will help you understand markets, categories, customers, and the power of being really specific.

I’d recommend Niche Down as a starting point, but Lochhead has a lot of other content that’s valuable to explore. He’s the co-author of another book, Play Bigger, which talks about category creation (not competing against other products, but rather inventing an entirely new category of products), and he’s the host of two phenomenal podcasts.

He’s also a fun author and speaker. He calls himself a pirate of the startup world, and it’s an apt descriptor. He’s as colorful as he is smart (The Economist once called him “offputting to some,” and he was so proud of the title he put it on his website’s About page).

The Hard Thing About Hard Things by Ben Horowitz

This is a book for CEOs, not employees, but it’s an invaluable read no matter who you are. As an early employee, one of the most confusing things is the way executives think. It feels like there are lots of curtains and secrets, and a lot going on that you sense is there but never get to see.

This book is the distillation of everything Horowitz learned in his 8 years as CEO of Opsware — one of the fastest-growing companies in the country during the dot-com boom, which had its IPO after the bubble burst, had to lay off large numbers of its employees four times, and eventually sold to HP for $1.6b.

This book breaks down what’s going on in the head of a CEO, and what happens behind the scenes. It offers a window into the things you don’t usually get to see a an entry-level employee, but that are critical to understand in order to grow.

It’s also a great book to read if you’re ambitious and know you want to rise up quickly in a company. It gives you some toeholds as you start to understand what you need to be thinking about in order to grow.

It’s also a great book to remind you how gritty startups are, and how much grit you’re going to need if you’re going to make it big.

The Inner Game of Tennis by Timothy Gallwey

This is a tennis book, not a business book, so it may seem odd to see it on the list. But Inner Game of Tennis is one of the most important books to read to level up your game.

The author of this book is a professional tennis coach. Over the course of his career, he started to see patterns in the way people learned — and realized that the biggest differentiator between people’s success was what was going on in their heads. He started experimenting with the way he gave people directions, the way he coached, and the way he helped people understand the game — and over time, he pivoted his coaching from teaching tennis to teaching the mindsets that are pivotal for success.

Just like in sports, your level of success in your career is going to hinge on what goes on between your ears. The sharper your mental game, the sharper your game in the real world is going to be.

The Magic of Thinking Big by David Schwartz

I’m a big fan of books written in the first half of the 20th century, and while 1959 doesn’t quite hit that mark, this book still has that old-school feel. Take a look at this quote from the opening chapter:

“The most essential element — in fact, the essential element — in our space explorations today is belief that space can be mastered. Without firm, unwavering belief that man can travel in space, our scientists would not have the courage, interest, and enthusiasm to proceed.”

In a similar vein to The Inner Game of Tennis, this book is all about what’s going on in your head. Your inner game is just as important is your outer game in the startup world. You’re creating something out of nothing, and running up against hard challenges, and pushing yourself farther than you thought you could go.

How you think makes the biggest difference in how you perform. Your level of success hinges on what you believe. The first step to succeeding is believing you’re able to succeed.

This book is all about getting your head in the right space, and establishing elite thinking. It also talks extensively about learning how to observe the people around you, and how they think, and how to adopt the mindsets you see in other people’s thinking.

The War of Art by Steven Pressfield

To be successful, you’re going to have to create stuff — the more the better — and you’re going to have to ship that stuff out into the world. Creating stuff is hard. Shipping it is even harder.

In The War of Art, Steven Pressfield talks about why shipping is so difficult — because of a force called Resistance, which is always present and always equal in measure to the importance of the thing you’re trying to accomplish. When you sit down to watch Netflix, you don’t feel Resistance, because what you’re trying to do isn’t worth much. But if you try to get up and clean your room, you’re going to feel a little bit of Resistance, because that activity has value. And if you decide to scrap all of the above and go write an article, let along a blog post, the force of Resistance is going to recognize that as something that’s both valuable and hard, you’re going to feel a lot of adversity in getting started.

Pressfield also talks about how to combat and overcome resistance, to be a consistent creator — and why it’s so important to do so. This is a phenomenal book to re-read on the regular. It will reset your creative process every time you pick it up.

The Best Articles and Essays

How to Get Work Done: A Primer — this one was a post on the Praxis blog written by my friend and colleague Chuck Grimmett. It’s a masterful overview of how to think about working and efficiency.

How to be Successful by Paul Graham — a phenomenal essay on thinking about your success and career growth.

Breaking Smart by Venkatesh Rao — a brilliant essay “miniseries” built off of Marc Andreessen’s quote “software is eating the world.” It explores how technology is changing everything in the world around us and gives you an edge in thinking about the future of the tech/startup world.

The Ultimate Gide to Writing Online by David Perell — the best professionals are writers too, and the fastest way to accelerate your career is through writing. David breaks down writing as a tool not only for communication, but for learning. This essay is a great resource as you’re building your career.

7 Essays That Will Help You Succeed in Internet Business by Taylor Pearson — this collection of essays is a great set of resources on thinking about your career. While it’s written for “internet business,” it’s highly applicable to all things startup, and should be studied thoroughly.

Patrick Collison on doing things that don’t scale — this is a talk, not an essay, but it still deserves a space on the list. It’s a great piece on thinking about getting in the weeds as a strategic move, to help you a) make your customers happy, and b) obtain the information you need to build systems that do scale.

Six Principles for Making New Things by Paul Graham — the title really says it all. A great essay on thinking about innovation.

The Most Important Points:

Make up for your lack of experience with the work of those who are smarter than you. They were generous enough to give you a window into their thought processes. Take advantage of them.

Pursue resources that help you gain knowledge not only about how startups work, but how innovators think. The history of innovation is one of the most important things to understand. It tells the story of all the people who saw things that didn’t yet exist, which are now part of your day-to-day world.

You Don’t Know How Much You Know

I talk all the time about how you don’t know what you don’t know. It’s one of the most important things in life — the more you know, the more you realize you don’t know.

But the reverse is also true — you don’t know how much you know.

And you won’t know, until there’s a context that draws it out.

We hold a vast amount of information that we never properly pin down, identify, and articulate. If there’s never a context in which you have to pin down an idea, you might never know it’s there.

It’s like driving through your town and never noticing all the mechanics’ shops that exist there until your car breaks down; at which point, you start to notice them everywhere. Or like never noticing that there’s kale in the produce aisle of most grocery stores, until you start cooking with it, at which point you see it every time you walk through the store.

If there’s never a context for our brains to stop and focus on something, we might never know it’s there.

We pick up information all the time — through conversations, content we consume, and things we experience and observe in life — and our brains file it away (and slowly process it for future use). But until we force ourselves to articulate it, we may never know it’s there.

This is why blogging is so valuable — because you have to stop and coalesce ideas that might otherwise never become concrete.

It’s why teaching and coaching have been so valuable to me — because when people ask me questions I’ve never considered before, I’m forced to try to answer them — which often leads me to realize I have answers I didn’t know I had.

When people ask me tough questions, I start to realize how much I don’t know that I don’t know. But at the same time, I start to realize how much I do know, that I never really saw before. I find myself intending to stall for time and turn out answering the question instead, in phrases and ideas I didn’t know I carried with me — but that, from that point forward, become deeply valuable to me.

There are few things in life more important than refining your knowledge. Seek this out constantly.

Give yourself writing prompts and force yourself to write. Put yourself in situations where you have to have philosophically challenging conversations. Seek out positions where you have to answer hard questions. When you force yourself to say things you haven’t said before, you realize just how much you didn’t realize you knew.

How to Make Yourself Smarter — Obvious and Inobvious Methods

One of my most prevalent goals is to become smarter — always.

When weighing opportunities, a job’s potential to make me smarter is more important than raw career growth (although the two often go hand-in-hand), monetary gains, or geographic location. It’s an important driver in my personal relationships, and in my choice of activities and pursuits outside of work.

Does it increase my knowledge of the world, and/or the functions of the world, particularly in the areas I hold interest? It’s a yes/no answer — and the answer is one of the most important data points in my decision-making process.

There are a number of reasons becoming smart is important to me:

1. It increases my effectiveness and ability professionally
2. It increases my potential for competence in my personal projects
3. It increases my creative problem-solving capacity
4. It increases the range of things I can intelligently write about
5. It makes me a better coach and teacher
6. It makes me a more valuable colleague, ally, and friend

“Smartness” is a personal definition, to some extent. It’s a value judgment, based on your desires and priorities. By my personal standards, smartness is:

1. The ability to think about complex ideas in a clear manner
2. The ability to creatively solve problems
3. Context for the world in which I’m working
4. Understanding why the world around me is the way it is, and understanding the layers at which I can explore this why.
5. A broad understanding of the broader intellectual world (that we culturally think of when we think about “intellect”)
6. Intellectual agility

The above can neatly divide into two categories: 1. concrete knowledge of objective facts, and 2. the ability to think.

The beauty about knowledge is that it compounds. The more you learn, the more things you become aware of that you need to learn more about, and the more questions you can ask (or the more connections you can draw), which in turn unlocks more knowledge — which repeats the cycle.

The pitfall of getting smarter is that it’s a subjective thing. It’s hard to measure in its raw form, and it’s hard to quantify your progress.

In future posts, I’ll expound on how to develop your ability in both areas — how to increase your knowledge base (that you use for your problem-solving), and your ability to think.

Imprecise Metaphors and Their Benefit for Your Thinking

David Perell wrote a fantastic blog post on the importance (or lack thereof) in the accuracy of maps. Side note — if you don’t follow David Perell, you should.
In a similar vein, I want to talk about the importance (or lack thereof) in the precision of one’s metaphors.
This is not an argument against being precise. It is not permission for ceasing to care about choosing the right metaphor.
This IS an argument that explores the nuance of metaphors as a vehicle for thinking — because they’re something I’ve become more and more dependent on, and dependency as complacency is a dangerous thing.
As I explored in an earlier post, I use whiteboards as a framework for thinking. They give me a structure that allows me to explore random ideas with a sense of familiarity — because there’s a framework that I know, and love, and can win.
Metaphors work in a similar way. I’ve become very fond of mathematical metaphors, because I love their streamlined efficiency. I love using mathematical metaphor to describe non-mathematical principles (like how the coaching process works, or how hiring managers think about candidates. I use mathematical metaphors in my work a lot).
The ideas are sometimes far-fetched, sometimes abstract, and sometimes things I’ve never endeavored to grapple with before — or even looked in the eye. The metaphoric framework gives me a space to explore them without having to define context.
I wonder sometimes if the metaphors are too limiting. Does an (a-b)=c equation give me enough flexibility to cover everything that matters? Am I missing important information by being artificially exclusive?
I wonder the same thing about whiteboards. Does the structure artificially constrain me and cause me to miss pivotal information that just doesn’t fit?
Here’s the thing: we can never be open to every possibility and still be conclusive. It isn’t possible. We must have absolute information in order to be definite.
Creativity likes working with definite quantities — but it isn’t static. What’s definite now can become a variable quantity in future.
The purpose of the metaphor isn’t to be absolute — the way the purpose of a map isn’t always to be exact. The purpose is to give a framework within which the information that’s most pivotal to our advancement and survival can be explored, articulated, and conveyed.