Book Review: Hackers & Painters

April 19, 2021

Cover: Hackers & PaintersPaul Graham is perhaps best known for his entrepreneurial work with Viaweb—one of the earliest online-shopping experiences, which Yahoo later purchased and made the Yahoo Store—and as a cofounder of Y Combinator, a venture-capital firm. Graham and Y Combinator made early-stage investments in a variety of startups, including disruptive firms such as Stripe, Doordash, Twitch, and many others.

Graham is also an accomplished designer of programming languages and was the creator of LISP. After finishing his computer science degree, in a somewhat unexpected turn, he studied painting. Hackers & Painters is a collection of Graham’s essays. Taken as a whole, the book is a thought-provoking work.

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Book Specifications

Title: Hackers & Painters: Big Ideas from the Computer Age

Author: Paul Graham

Formats: Paperback, Hardcover, Audible

Publisher: O’Reilly Media

Published: May 2004

Pages: 336

ISBN-10: 0-596-00662-4

ISBN-13: 978-0-596-00662-4

Why Nerds are Unpopular

The first and perhaps most popular essay is Graham’s analysis of teenage social dynamics. Most anyone who has attended middle school in the United States would recognize the stratified and dysfunctional caste system that has evolved—sorting children into categories from that of the enviable popular kids to the loathsome nerds.

Graham describes how he and his friends applied their intellect to understanding the social dynamics that played out in the school lunchroom. They defined five categories, ranging from A, which they reserved for jocks and cheerleaders, to E, which comprised only mentally handicapped kids. Graham, a confessed nerd, and his friends realized that they belonged to the D category.

Rather than lamenting the unfairness of school life, Graham’s essay seeks to understand why things are the way they are, and he provides some compelling explanations. Some might posit that, if nerds are so smart, they should be able to crack the code and find ways of becoming more popular. However, according to Graham’s assessment, nerds actually value intelligence over popularity. Plus, it takes a lot of work to become popular and sustain that vaunted status.

Ultimately, the dysfunctional social order could be due to the artificial construct of school itself. While in earlier generations, children of middle-school age might have been apprentices and held actual jobs, our industrialized society has created an extended—and seemingly pointless—childhood. Rather than having a constructive purpose, pursuing their interests, and being contributing members of society, middle-school aged children spend much of their time in dreary classrooms, reciting facts and figures that would likely have little bearing on their adult life. Because the stakes within middle school are so low, the conflicts are intense—hence the rise of bullying. Popular kids ultimately persecute nerds to make themselves feel better.

Hackers & Painters

In a somewhat rambling essay, from which the book takes its title, Graham describes the similarities between hackers, or programmers, and painters. While people might assume that someone in computer science would follow logical procedures with predictable inputs and outcomes, Graham describes a much more purposeful drive: both hackers and painters are ultimately trying to create something new. There is also a certain amount if improvisation that happens in both painting and hacking. Things don’t go perfectly the first time around, so iterations and even imperfections become part of the work product.

Both hackers and painters are ultimately makers who produce something for other people. The importance of the concept of making things for people arises in Graham’s other essays as well. Of course, making something for people requires empathy, a trait that is necessary for successful hackers, designers, and other creative people.

How to Make Wealth

In a longer essay, Graham gives us his thoughts on how to create wealth—and dispels some of the myths of wealth. Given his role with Y Combinator, it should not be surprising that Graham has a preference for making wealth through technology startups.

Graham is specific in his description of what a startup is and how it works. According to his definition, a startup is a company that people have formed for the purpose of solving a difficult problem and generating wealth thereby. So, for example, a company providing social-media marketing services might not be a bona fide startup, but a company creating software to automate social-media postings would be. More than just starting a company, a startup’s founders compress their wealth-creating potential into a short period of time. Rather than committing to 40 hours a week, working for a typical salary, the startup founder commits to working many more hours a week, seeking much bigger returns.

The pie fallacy is a popular misconception of wealth that can limit people’s potential and create distortions in the way we perceive wealth creation. First, it is important to understand that wealth is not the same thing as money. As Graham notes, wealth has existed for much longer than money—and even animals such as ants have a concept of wealth. Wealth is nothing more than the capacity to attain the goods and services you want. The pie fallacy posits that there is only so much wealth available in the world, for which all people must compete. But this cannot be true. One can simply compare the standard of living and growth in the availability of goods and services over centuries to see that wealth has expanded.

In providing a great example of the ability to create wealth, which breaks the pie fallacy, Graham describes how a person can purchase an old car; make improvements to it through their work and purchasing new components; then, ultimately, sell the vehicle for more than the sum of the purchase price. This illustrates how you can create wealth without exploiting others and that wealth creation isn’t a zero-sum game. In fact, this is the model for real-estate flipping. Of course, there could also be the positive externality that, if a house that is adjacent to mine sells for a higher price, my home becomes more valuable, thus creating wealth for me.

Again, in this essay, Graham extols the virtue of being able to make things, as he describes the innate ability of traditional craftsmen and programmers to generate wealth through their talent.


Graham commits a fairly large proportion of his writings to discussing opportunity, relationships, and wealth creation. His essays could be read as a defense of the enormous wealth that California technology moguls enjoy. Indeed, it is a fair assessment that, for many entrepreneurs in new technologies—throughout history, by the way—being in the right place at the right time has played an outsized role in their success. Of course, having the ability to respond to opportunities is an important variable in the formula for success—if one exists.

However, I read Graham’s book less as an apologist for the wealthy technology entrepreneurs of the late ’90s and early 2000s and more as encouragement to other would-be entrepreneurs. The work that he and Y Combinator have done in developing early-stage companies—through training and direct investment—are a testament to Graham’s commitment to helping other people succeed.

Hackers & Painters is definitely not your typical text on user experience or design. It is much more about Graham’s philosophy for applying design to solving business problems, devising strategies, and expanding opportunities. This book is an important collection of writings from which any mid- or senior-level UX professional could learn some valuable lessons. 

Vice President, User Experience at Metisentry

Owner of TheoremCX

Kent, Ohio, USA

D. Ben WoodsBen began his career in 1999, when businesses were just beginning to recognize the World Wide Web as a valuable tool. Prior to his appointment at Kent State, he held positions as a UX designer and UX manager. He has worked with global teams and a variety of consulting firms to deliver research and design that improved digital experiences for customers. He has also developed his organizations’ analytics discipline to track the performance of digital properties and identify opportunities for improvement. Ben’s company TheoremCX is an innovation firm that provides customer-focused solutions. He has developed solutions and corporate workshops for a variety of organizations around the world, including Eaton, General Electric, Knoch Corporation, and Orange S.A. Ben is the chairperson of UX Akron, a nonprofit professional network serving Summit and Portage Counties, as well as all of Northeast Ohio.  Read More

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