Reading List

Authors Like Paul Graham

Paul Graham was born in Weymouth, England, in 1964, took a PhD in computer science at Harvard and then studied painting at RISD and in Florence. In 1995 he and Robert Morris started Viaweb, software for building online shops, and in 1998 they sold it to Yahoo, where it became Yahoo Store. From 2001 he began posting essays on his own website; O'Reilly collected a set of them as Hackers & Painters in 2004. The next year a talk he gave to the Harvard Computer Society, later published as “How to Start a Startup”, turned into Y Combinator, which he founded with Jessica Livingston, Morris and Trevor Blackwell, and which went on to fund Airbnb, Dropbox, Stripe and Reddit. He stepped back from its day-to-day running in 2014 and has kept writing. Readers come to him for two things: plain, short sentences that make a hard idea look obvious, and the sense of watching someone work a question out from first principles — about startups, but just as often about taste, ambition or why nerds are unpopular. The writers below share either his subject — how software and companies actually get built — or his method: the essay as a way of thinking something through in public.

By Lisanne Swart · 10 authors · Startups · Software · The essay · Updated October 2026

Quick answer

If you love Paul Graham, start with Jessica Livingston's Founders at Work, the interview book by his Y Combinator co-founder. For the programmer-essayist next to him, read Joel Spolsky; for the hacker culture he came out of, Steven Levy's Hackers. For startup thinking with a harder edge, Peter Thiel. And for where his kind of essay began, Montaigne.

10 authors like Paul Graham

01
His co-founder · Closest match

Jessica Livingston

American · b. 1971 · Interviewer and investor

Livingston studied English at Bucknell and in 2005 co-founded Y Combinator with Paul Graham, Robert Morris and Trevor Blackwell; she and Graham married in 2008. Founders at Work (2007) is a book of long interviews with the founders of early technology companies, Steve Wozniak among them, about what the first months were really like. She started YC's Female Founders conference in 2013 and since 2023 has co-hosted the podcast The Social Radars with Carolynn Levy.

The companion volume to the essays. Graham generalises; Livingston lets founders tell the specific story, mess included, and the patterns he writes about — the pivot, the early user, the near-death moment — turn up again and again in their own words. It is the evidence behind a good share of his arguments.

— Lisanne
02
The hacker culture he came from

Steven Levy

American · b. 1951 · Reporter

Hackers: Heroes of the Computer Revolution (1984) grew out of a 1981 Rolling Stone article and follows programmers from the MIT labs of the 1950s to the early game makers of the 1980s; it set out the “hacker ethic” that information should be free and computers can improve life. Levy has since written Insanely Great (1994) on the Macintosh, In the Plex (2011) on Google and Facebook: The Inside Story (2020), and has been at Wired since 2008.

Graham's title Hackers & Painters assumes you know what a hacker is in the old, admiring sense; Levy is where that sense is written down. Read it for the history behind Graham's view of programmers as makers, and for a reporter's account of the same type of obsessive, playful builder that Y Combinator went looking for.

— Lisanne
03
The programmer-essayist next door

Joel Spolsky

American · b. 1965 · Programmer and essayist

Spolsky was born in Albuquerque, grew up partly in Israel, and in 2000 started both the software company Fog Creek and the blog Joel on Software, whose essays were collected in book form in 2004 and 2008. In 2008 he co-founded Stack Overflow with Jeff Atwood; it was sold in 2021 for $1.8 billion. Fog Creek also launched Trello in 2011.

The nearest thing to a contemporary of Graham's in the same genre: a working programmer who started writing essays online at almost the same moment and built an audience of developers with them. Spolsky is funnier and more practical — hiring, schedules, bug tracking — where Graham is more abstract, but both write for the reader who builds things.

— Lisanne
04
The classic essays on building software

Fred Brooks

American · b. 1931 · Computer scientist

Brooks managed the development of IBM's System/360 computers and their OS/360 operating system, and wrote up what he learned in The Mythical Man-Month (1975), a book of essays on software projects. It gave the field Brooks's law: “Adding manpower to a late software project makes it later.” He won the Turing Award in 1999 and published The Design of Design in 2010.

The older book Graham's essays on software quietly argue with and agree with. Brooks writes from inside one of the biggest projects of his time; Graham from inside a three-person startup; both conclude that small teams of good people beat large organisations, and both say it in clear, unfussy prose.

— Lisanne
05
Short essays on running a business

Derek Sivers

American · b. 1969 · Essayist

Sivers was a professional musician before he started CD Baby, an online shop for independent music, which he sold to Disc Makers in 2008 for $22 million. Anything You Want (2011) is forty short lessons from building and selling it. He has since published Hell Yeah or No (2020), How to Live (2021) and Useful Not True (2024).

Sivers shares Graham's distrust of received business wisdom and his preference for what actually happened over theory, and he writes even shorter. Where Graham builds an argument over several thousand words, Sivers makes one point in a page and stops. Anything You Want reads in an hour and is the best place to start.

— Lisanne

Every book by Derek Sivers →

06
First principles, compressed

Naval Ravikant

Indian-American · b. 1974 · Investor

Ravikant was born in New Delhi, co-founded the review site Epinions in 1999 and in 2010 co-founded AngelList, which grew out of the Venture Hacks blog he began in 2007. The Almanack of Naval Ravikant (2020) was compiled by Eric Jorgenson from his tweets, essays and interviews, with his permission, on wealth and happiness.

The aphorism to Graham's essay. Both reason from first principles about how wealth is made and why most advice about it is wrong, but Ravikant compresses an idea into a line and leaves the reader to unpack it. Because the Almanack is assembled by someone else, it reads as a collection rather than an argument.

— Lisanne
07
Startup thinking, more contrarian

Peter Thiel

German-American · b. 1967 · Investor

Thiel was born in Frankfurt, co-founded PayPal in 1998 and invested $500,000 in Facebook in 2004. Zero to One (2014), written with Blake Masters, grew out of Masters's notes on Thiel's 2012 Stanford class on startups and argues that founders should build monopolies rather than compete. In 2016 he confirmed that he had paid about $10 million towards lawsuits against Gawker Media, including Hulk Hogan's, which ended in a $140 million verdict and Gawker's closure.

The closest book to Graham's startup essays in subject, and the sharpest contrast in tone. Both ask what most people believe that is not true; Thiel answers more provocatively and with more appetite for power. Read them together and Graham's version looks gentler and more empirical.

— Lisanne

Every book by Peter Thiel →

08
When the startup gets hard

Ben Horowitz

American · b. 1966 · Investor

Horowitz co-founded Loudcloud with Marc Andreessen in 1999, turned it into Opsware and sold it to Hewlett-Packard in 2007 for $1.6 billion. In 2009 the two founded the venture firm Andreessen Horowitz. The Hard Thing About Hard Things (2014) is about running a company through near-collapse; What You Do Is Who You Are (2019) is about company culture.

Graham writes mostly about the start: the idea, the first users, the founders. Horowitz writes about what comes after, when the company is big enough to fail expensively, and he is blunter about layoffs, firing executives and fear. It is the book for the reader who has taken Graham's advice and now runs something.

— Lisanne
09
The essayist as contrarian

Nassim Nicholas Taleb

Lebanese-American · b. 1960 · Essayist

Taleb was born in Amioun, Lebanon, and worked as a derivatives trader for about twenty years before writing the five-book Incerto: Fooled by Randomness (2001), The Black Swan (2007), The Bed of Procrustes (2010), Antifragile (2012) and Skin in the Game (2018). The books are about chance, risk and why experts so often fail to see either.

Like Graham, Taleb distrusts credentials and prefers what works in practice to what sounds right in theory, and both have a habit of making the reader feel slightly foolish about a belief they never examined. Taleb is far more combative and digressive; Graham far tidier. Antifragile is the one closest to Graham's interest in small, adaptable things beating large, fragile ones.

— Lisanne

Every book by Nassim Nicholas Taleb →

10
Where the essay began

Michel de Montaigne

French · b. 1533 · Essayist

Montaigne left his legal career in 1571 and withdrew to the tower of his family château to read and write. The first two books of his Essais appeared in 1580; the 1588 edition added a third book and some six hundred additions, and he served as mayor of Bordeaux from 1581 to 1585. He was the first to use the word for a short prose piece: an essai was a trial or an attempt.

The origin of what Graham does. An essay in Montaigne's sense is not a finished argument but an attempt to find out what you think by writing, and that is exactly how Graham's essays read. Montaigne's subjects are friendship, cruelty and death rather than startups, but the habit of following a thought wherever it goes is the same.

— Lisanne

Every book by Michel de Montaigne →

Where to start if you loved Paul Graham

If you want the startup stories behind the essays, read Jessica Livingston.

Founders at Work: the people Graham writes about, in their own words.

If you want another programmer who writes like this, read Joel Spolsky.

Joel on Software — practical, funny, and from the same years.

If you want the hacker culture behind Hackers & Painters, read Steven Levy.

Hackers, the 1984 book that wrote the hacker ethic down.

If you want the essay at its source, read Montaigne.

Start with “Of Friendship” or “Of Experience” in any good translation.

Frequently asked questions about authors like Paul Graham

Who should I read if I love Paul Graham?

Jessica Livingston's Founders at Work is the closest companion: she co-founded Y Combinator with Graham and interviewed dozens of founders about their first years. Joel Spolsky is the programmer-essayist writing at the same time; Steven Levy's Hackers covers the culture Graham came out of. For startup thinking, Peter Thiel and Ben Horowitz; for short essays on business and life, Derek Sivers; for the origin of the essay itself, Montaigne.

What books are like Hackers & Painters?

Joel Spolsky's Joel on Software (2004), a collection of a working programmer's essays from the same years, is the nearest. Fred Brooks's The Mythical Man-Month (1975) is the classic book of essays on how software gets made, and Steven Levy's Hackers (1984) is the history of the culture the title refers to.

Does Paul Graham have a book of essays?

Yes. Hackers & Painters: Big Ideas from the Computer Age was published by O'Reilly in 2004 and collects essays from his website. His other books, On Lisp and ANSI Common Lisp, are programming books. His essays, including those in the book, are free to read on paulgraham.com.

Who is Jessica Livingston?

An American writer and investor, born in 1971, who co-founded Y Combinator with Paul Graham, Robert Morris and Trevor Blackwell in 2005. She married Graham in 2008. Her book Founders at Work (2007) collects interviews with founders of early technology companies, and she co-hosts the podcast The Social Radars.

Is Naval Ravikant similar to Paul Graham?

In subject, yes: both are Silicon Valley investors who reason from first principles about wealth, work and judgement. In form they differ. Graham writes long, carefully built essays; Ravikant's ideas mostly come in short lines, and The Almanack of Naval Ravikant (2020) was compiled from his tweets and interviews by Eric Jorgenson.

What should I read after Paul Graham if I want to start a company?

Livingston's Founders at Work for how other founders did it, Peter Thiel's Zero to One (2014) for a contrarian theory of what to build, and Ben Horowitz's The Hard Thing About Hard Things (2014) for what happens when it gets difficult. Derek Sivers's Anything You Want (2011) is the short version for anyone building something small.

Footnotes

  1. Paul Graham — Wikipedia
  2. Paul Graham — Bio, paulgraham.com
  3. Jessica Livingston — Wikipedia
  4. Steven Levy — Wikipedia
  5. Joel Spolsky — Wikipedia
  6. Fred Brooks — Wikipedia
  7. Zero to One: How Blake Masters Went From Being Peter Thiel's Student To Co-Author — TechCrunch
  8. Michel de Montaigne — Renaissance in Print, University of Virginia Library

List last reviewed 15 October 2026.

Written by Lisanne Swart, who has curated reading lists and author guides at lisanneswart.com since 2021. Every comparison here is a judgement about method and subject, not an algorithmic match. See more on her personal bookshelf.

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