My Reading Recommendations for New Startup Employees

When I talk to other young people about what it’s like to work in a startup environment, I often get asked about the books that have helped me most. As anyone who has received gifts from me could tell you, I am happy to oblige a request for reading recommendations.

Here’s a quick rundown of the books and essays that have helped me get through my first couple of years at BitPay – and to become a better employee and person along the way. You’ll notice that very few are explicitly related to startups.

#1: The Startup of You

LinkedIn founder Reid Hoffman and Ben Casnocha make the case that you need to think and act like an entrepreneur to build equity in yourself. Every action you take in your career working for someone else is an action that can add or subtract from your value and potential. Every day you work, you can build your skills, your resources, and your unique insights that enable you to create value in the world – regardless of whether you ever start a company.

#2: Zero to One

This book is an edited compilation of PayPal founder and Founder’s Fund investor Peter Thiels’ notes on startups given to Stanford University students. The takeaway for me? Think about what your unfair advantage is – the secret insight you have that can give you a monopoly or first mover advantage in whatever you want to accomplish in your world. If you do that, you can innovate and create something new while others compete.

#3: That Which is Seen, and That Which Is Not Seen

This is a selection from French classical liberal stateman Frederic Bastiat on one of the most important tools of economic thinking (and business thinking): seeing the unseen in the value creation and destruction that goes on around us every day. This essay is a powerful reminder of the importance that opportunity cost – and not just immediately perceived cost/benefit – should have in our calculations of how to act.

#4: The Use of Knowledge in Society

If you want to begin to understand how economies and societies work without central planning or direction, this is the place to start. Hayek brilliantly explains how the price system coordinates the actions of millions and billions of strangers to provide for almost every desire and need humans have. This essay will humble you, make you appreciate every working person and every job you ever encounter (or do), and awe you with a sense of the simultaneous fragility and robustness of human creativity.

#5: On Writing Well

This book played a major role in showing me exactly how badly school had screwed up my writing. On Writing Well is a classic guide to avoiding the bullshit that most people include in their nonfiction writing: the cliches, clutter, weak phrasings, and lack of specificity that make a piece of writing painful to read. The author pulls back the curtain on the writing process for everything from science writing to travel writing and business writing. You won’t read other people’s writing – let alone your own – in the same way after checking out this book.

#7: Antifragile

In Antifragile, contrarian statistician, sociologist, and crotchety-old-wise-man Nassim Taleb presents a new thesis: there are some things which get stronger when exposed to stress and disorder. From the human body to self-employment to decentralized societies, Taleb details how apparently “disorderly” and “unstable” modes of being actually win in the face of chaos and change. On the other hand, the things we often consider reliable and steady bets – full-time jobs, centralized economies, large corporations  – are most subject to disruption when the world changes.

#8: The Four-Hour Workweek

Tim Ferriss is a strange animal, and he’s one you should learn from. A self-described human guinea pig, Ferriss has staged and written on experiments from health science and personal training to how the world’s best athletes, artists, and entrepreneurs learn and create. The Four-Hour Workweek was Ferriss’s first work, and it still holds up as a manual on achieving efficacy over efficiency, automating and delegating the tasks of running a business or doing a job, designing an independent life beyond the wastefulness of the 9 to 5, and building in the things you actually want out of life – exploration, freedom, and personal development – into your pre-retirement years.

#9: Atlas Shrugged

Atlas Shrugged was one of the most popular and controversial books of the 20th century in the United States, and for good reason. From themes like the virtues of selfishness and creativity, the absoluteness of individual moral responsibility, and the sacredness of the human mind, Atlas was author Ayn Rand’s attempt to present an alternative to the downward-spiral of the century’s totalitarian ideals and the West’s half-hearted approach to defending real humanist ideals.

Whether or not you agree with Rand’s full philosophical conclusions, this book will force you to think about what kind of world your code of values is creating. It will give you a profound understanding of evil and a new appreciation for the good all around you – especially the good created in businesses in the pursuit of profit. You’ll want to have both if you want to come out at the other end of your career with your soul intact.

Honorable Mention: Rand’s The Fountainhead is another great novel on the relationship between integrity and creativity. I recommend it highly. 

#10: The Lord of the Rings

Working in a startup is a quest. Every day of startup work is a battle. If you don’t have a proper relationship with fantasy and mythology, you’ll lack the metaphors and role models you will need to get through the darkest and most trying moments of your work. Enter J.R.R. Tolkien. In The Lord of the Rings, Tolkien created the mythological masterwork of the 20th century.

In your work as a startup employee, you will face the same moral choices faced by all of Tolkien’s characters: whether to be loyal, and what loyalty means (Samwise Gamgee); how to be heroic even when the world sees you as insignificant (Frodo); how to fulfill a long mission without giving into evil or despair (Gandalf); how to lead without glorifying yourself or dominating others (Aragorn). Need I say more? Read it.

#11: The Great Divorce  

Ostensibly a religiously-themed book written by Christian thinker C.S. Lewis, The Great Divorce is an uncommon revisitation and dramatization of the ideas of Heaven and Hell. In a series of conversations between the inhabitants of the two realms, Lewis explores how most modern people turn romantic love into a tool of envy, familial love into a tool of control, power into self-cannibalism, intellect into incuriousity, sexual desire into a hideous taskmaster, and “moral decency” into self-blindness.

In The Great Divorce, Lewis ends up writing one of the most observant, funny, sad, and challenging books on personal transformation (and the lack thereof) that I’ve ever encountered. Hell is a state of mind which is almost entirely self-imposed. Heaven is an uphill climb – further up and further into real goodness and truth. Read this book. You’ll be far better equipped to grow into the kind of person you want to be in your life – and in your startup career.

#12 (Bonus): EconTalk

This isn’t a book but a podcast. You should still listen to it. EconTalk is one of the best resources I know for learning just about any subject, from sports and psychology to history and cooking and why grocery stores are laid out the way they are. Even better, each topic gets a treatment in the economic way of thinking – or, in other words, you actually get to understand the logic of the human action behind everything in the modern world. It will transform the way you think and make you far more open to opportunities for appreciation and value creation.

James Walpole

James Walpole is a writer, startup marketer, and perpetual apprentice. You're reading his blog right now, and he really appreciates it. Don't let it go to his head, though.

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