Paul Graham is most famous for heading up Y Combinator, a seed-stage startup funding firm, and also for Hacker News, a social news website revolving around computer hacking, startup companies, and as their submission guidelines state, “anything that gratifies one’s intellectual curiosity”.

Graham’s essays online are highly regarded for their insight and relevance – and his book, Hackers and Painters, is no different.

Hackers and Painters, as Graham describes it, “examines the world of hackers and the motivations of the people who occupy it.” Although it informs the world of hackers more generally, the concepts within reach much further, and have many takeaways outside the programming world. For the uninformed, “hackers” , are the programmers and developers that code the internet – not the traditionally imagined security disrupters and virus-spreaders as is sometimes thought.

The idea of “hackers”, here, can be moved over to the “makers” – people that create. If you ever find yourself thinking these insights don’t apply to your own life, substitute hacker for maker and you’ll understand that Paul Graham’s thoughts go beyond the specialization of developing and programming.

To help inform the great insights from the book, I included the essay title and summary, as Graham offers in the contents. A few chapters had only one or two notes or none at all, because they were overly technical or not particularly relevant to a wider audience. I have included those at the end.

Why Nerds are Unpopular – Their minds are not on the game.

1. Nerds serve two masters. They want to be popular, certainly, but they want even more to be smart.

2. An American teenager may work at being popular every waking hour, 365 days a year.

3. Most people seem to consider the ability to draw as some kind of innate quality, like being tall. In fact, most people who “can draw” like drawing, and have spent many hours doing it; that’s why they’re good at it.

4. Smart people’s lives are worst between, say, the ages of eleven and seventeen. Life at that age revolves far more around popularity than before or after.

5. People unsure of their own position will try to emphasize it by maltreating those they think rank below.

6. To become more popular, you need to be constantly doing things that bring you close to other popular people, and nothing brings people closer than a common enemy.

7. The most popular kids don’t persecute nerds, they don’t need to stoop to such things. Most of the persecution comes from kids lower down, the nervous middle classes.

8. I think the important thing about the real world is not that it’s populated by adults, but that it’s very large, and the things you do have real effects. That’s what school, prison, and ladies-who-lunch all lack. The inhabitants of all those worlds are trapped in little bubbles where nothing they can do can have more than a local effect.

9. Why do people move to suburbia? To have kids! So no wonder it seemed boring and sterile. The whole place was a giant nursery, an artificial town created explicitly for the purpose of breeding children.

10. And as for the schools, they were just holding pins within this fake school. Officially the purpose of schools is to teach kids. In fact their primary purpose is to keep kids locked up in one place for a big chunk of the day so adults can get things done.

11. What bothers me is not that the kids are kept in prisons, but that (a) they aren’t told about it, and (b) the prisons are run mostly by the inmates. Kids are sent off to spend 6 years memorizing meaningless facts in a world ruled by a caste of giants who run after an oblong brown ball, as if this were the most natural thing in the world. And if they balk at this surreal cocktail, they’re called misfits.

12. In pre-industrial times, (kids) were all apprentices of one sort of another, whether in shops or on farms or even on warships. / Teenagers seem to have respected adults more then, because the adults were the visible experts in the skills they were trying to learn. Now most kids have little idea what their parents do in their distant offices, and see no connection (indeed, there is precious little) between schoolwork and the work they’ll do as adults.

13. it’s important for nerds to realize, too, that school is not life. School is a strange, artificial thing, half sterile and half feral. It’s all encompassing, like life, but it isn’t the real thing. It’s only temporary, and if you look, you can see beyond it even while you’re still in it.

Hackers and Painters – Hackers are makers, like painters or architects or writers.

14. Samuel Johnson said it took a hundred years for a writer’s reputation to converge. You have to wait for the writer’s influential friends to die, and then for all their followers to die.

15. Everyone in the sciences secretly believes that mathematicians are smarter than they are. I think mathematicians also believe this. At any rate, the result is that scientists tend to make their work look as mathematical as possible.

16. A page of formulas just looks so impressive. And so there is a great temptation to work on problems that you can treat formally, rather than problems that are, say, important.

17. Big companies want to decrease the standard deviation for design outcomes because they want to avoid disasters. But when you damp oscillations, you lose the high points as well as the low.

18. Because painters leave a trail of work behind them, you can watch them learn by doing. If you look at the work of a painter in chronological order, you’ll find that each painting builds on things learned in previous ones.

19. Scientists start out doing work that’s perfect, in the sense that they’re just trying to reproduce work someone else has already done for them. Eventually, they get to the point where they can do original work. Whereas hackers, from the start, are doing original work; it’s just very bad. So hackers start original, and get good, and scientists start good, and get original.

20. The other way makers learn is from examples. To a painter, a museum is a reference library of techniques. For hundreds of years it has been part of the traditional education of painters to copy the works of the great masters, because copying forces you to look closely at the way a painting is made.

21. Empathy is probably the single most important difference between a good hacker and a great one. Some hackers are quite smart, but practically solipsists when it comes to empathy. It’s hard for such people to design great software, because they can’t see things from the user’s point of view.

22. What we can say with some confidence is that these are the glory days of hacking. In most fields the great work is done early on. The paintings made between 1430 and 1500 are still unsurpassed. / Over and over we see the same pattern. A new medium appears, and people are so excited about it that they explore most of its possibilities in the first couple generations. Hacking seems to be in this phase now. / Painting was not, in Leonardo’s time, as cool as his work helped make it. How cool hacking turns out to be will depend on what we can do with this new medium.

What You Can’t Say – How to think heretical thoughts and what do with them.

23. In every period of history, people believe things that were just ridiculous, and believe them so strongly that you would have gotten in terrible trouble for saying otherwise. | It’s tantalizing to think we believe things that people in the future will find ridiculous. What WOULD someone coming back to visit us in a time machine have to be careful not to say?

24. The statements that make people mad are the ones they worry might be believed. I suspect the statements that make people are maddest are those they worry might be true.

25. In a field like physics, if we disagree with past generations it’s because we’re right and they’re wrong. But this becomes rapidly less true as you move away from the certainty of the hard sciences. By the time you get to social questions, many changes are just fashion.

26. In our own time, different societies have wildly varying ideas of what’s ok and what isn’t. So you can try diffing other cultures’ ideas against ours as well. / In one culture x is ok, and in another it’s considered shocking. My hypothesis is that the side that’s shocked is most likely to be the mistaken one.

27. Kids’ heads are repositories of all our taboos. / The picture we give them of the world is not merely simplified, to suit their developing minds, but sanitized as well, to suit our ideas of what kids should think.

28. A well brought-up teenage kid’s brain is a more or less complete collection of all our taboos- and in mint condition, because they’re untainted by experience.

29. Moral fashions don’t seem to be created by the way ordinary fashions are. Ordinary fashions seem to arise by accident when everyone imitates the whim of some influential person. | Moral fashions more often seem to be created deliberately. When there’s something we can’t say, it’s often because some group doesn’t want us to.

30. To launch a taboo, a group has to be posed halfway between weakness and power. A confident group doesn’t need taboos to protect it. It’s not considered improper to make disparaging remarks about Americans, or the English. And yet a group has to be powerful enough to enforce a taboo.

31. I suspect the biggest source of moral taboos will turn out to be power struggle sin which one side barely has the upper hand. That’s where you’ll find a group powerful enough to enforce taboos, but weak enough to need them.

32. Most struggles, whatever they’re really about, will be cast as struggles between competing ideas. It’s easier to get people to fight for an idea. And whichever side wins, their ideas will also be considered to have triumphed, as if God wanted to signal his agreement of that side as the winner. | We often like to think of World War II as a triumph over totalitarianism. We conveniently forget that the Soviet Union was also one of the winners.

33. Although fashions in ideas tend to arise from different sources than fashions in clothing, the mechanism of their adoption seems much the same. The early adopters will be driven by ambition: self-consciously cool people who want to distinguish themselves from the common herd. As the fashion becomes established they’ll be joined by a second, much larger group, driven by fear.

34. Whatever the reason, there seems a clear correlation between intelligence and willingness to consider shocking ideas. This isn’t just because smart people actively work to find holes in conventional thinking. Conventions also have less hold over them to start with. You can see that in the way they dress.

35. When you find something you can’t say, what do you do with it? My advice is, don’t say it. Or at least, pick your battles. | Argue with idiots, and you become an idiot. | The most important thing is to be able to think what you want, not to say what you want.

36. The people you can say heretical things to without getting jumped on are also the most interesting to know.

37. When people are bad at math, they know it, because they get the wrong answers on tests. But when people are bad at open-mindedness, they don’t know it. In fact they tend to think the opposite.

Good Bad Attitude – Like Americans, hackers win by breaking rules.

38. Civil liberties are not just an ornament, or a quaint American tradition. Civil liberties make countries rich. | Authoritarian countries become corrupt, corrupt countries become poor; and poor countries are weak.

39. “The spirit of resistance to government,” Jefferson wrote, “is so valuable on certain occasions, that I wish it always to be kept alive.”

The Other Road Ahead – Web-based software offers the biggest opportunity since the arrival of the microcomputer.

40. The whole idea of “your computer” is going away, and being replaced with “your data.” You should be able to get at your data from any computer. Or rather, any client, and a client doesn’t have to be a computer.

41. Some amount of piracy is to the advantage of software companies. If some user would never have bought your software at any price, you haven’t lost anything if he uses a pirated copy. In fact you gain, because he is one more user helping to make your software the standard – or who might buy a copy later, when he graduates high school.

42. Web –based software sells well, especially in comparison to desktop software, because it’s easy to buy.

43. E.B. White was amused to learn from a farmer friend that many electrified fences don’t have any current running through them. The cows apparently learn to stay away from them, and after that you don’t need the current. | If you’re a hacker who has thought of one day starting a startup, there are probably two things keeping you from doing it. One is that you don’t know anything about business. The other is that you’re afraid of competition. Neither of these fences have any current in them.

How to Make Wealth – The best way to get rich is to create wealth. And startups are the best way to do that.





44. So although there may be, in certain specific moments, a fixed amount of money available to trade with other people for things you want, there is not a fixed amount of wealth in the world. You can make more wealth.

45. Suppose you own a beat-up old car. Instead of sitting your butt next summer, you could spend the time restoring your car to pristine condition. In doing so you create wealth. The world is – and you specifically are – one pristine old car the richer. And not just in some metaphorical way. If you sell your car, you’ll get more for it. | In restoring your old car you have made yourself richer. You haven’t made anyone else poorer.

46. To get rich you need to get yourself in a situation with two things, measurement and leverage. You need to be in a position where your performance can be measured, or there is no way to get paid more by doing more. And you have to have leverage, in the sense that the decisions you make have a big effect.

Mind the Gap – Could “unequal income distribution” be less of a problem than we think?





47. Like chess or painting or writing novels, making money is a very specialized skill. But for some reason we treat this skill differently. No one complains when a few people surpass all the rest at playing chess or writing novels, but when a few people make more money than the rest, we get editorials saying this is wrong.

48. I think there are three reasons we treat making money as different: the misleading model of wealth we learn as children; the disreputable way in which, till recently, most fortunes were accumulated, and the worry that great variations in income are somehow bad for society. As far as I can tell, the first is mistake, the second outdated, and the third empirically false.

49. In the United States, the CEO of a large public company makes about 100 times as much as the average person. Basketball players make about 128 times as much, and baseball players 72 times as much. Editorials quote this kind of statistic with horror. But I have no trouble imagining that one person could be 100 times as productive as another.

50. But since for most of the world’s history the main route to wealth was to steal it, we tend to be suspicious of rich people.

51. Will technology increase the gap between rich and poor? It will certainly increase the gap between the productive and the unproductive. That’s the whole point of technology. With a tractor an energetic farmer could plow six times as much land in a day as he could with a team of horses. But only if he mastered a new kind of farming.

52. If you suppress variations in income, whether by stealing private fortunes, as feudal rulers used to do, or by taxing them away, as some modern governments have done, the result always seem to be the same. Society as a whole ends up poorer.

53. If I had a choice of living in a society where I was materially much better off than I am now, but was among the poorest, or in one where I was the richest, but much worse off than I am now, I’d take the first option. | It’s absolute poverty you want to avoid, not relative poverty.

54. You need rich people in your society not so much because in spending their money they create jobs, but because of what they have to do to get rich. I’m not talking about the trickle-down effect here. I’m not saying that if you let Henry Ford get rich, he’ll hire you as a waiter at his next party. I’m saying that he’ll make you a tractor to replace your horse.

A Plan for Spam – Till recently most experts thought spam filtering wouldn’t work. This proposal changed their minds.





55. False positives are innocent emails that get mistakenly identified as spams. For most users, missing legitimate email is an order of magnitude worse than receiving spam, so a filter that yields false positives is like an acne cure that carries a risk of death to the patient.

56. Nobert Wiener said if you compete with slaves you become a slave, and there is something similarly degrading about competing with spammers. To recognize individual spam features you have to try to get into the mind of the spammer, and frankly I want to spend as little time inside the minds of spammers as possible.

57. Based on my corpus, sex indicates a .97 probability of the containing email being a spam, whereas sexy indicates .99 probability. And Baye’s rule, equally unambiguous, says that an email containing both words would, in the (unlikely) absence of any other evidence, have a 99.97% chance of being a spam.

58. Spammers send spam because it works. It works because although the response rate is abominably low (at best 15 per million, vs 3000 per million for a catalog mailing), the cost, to them, is practically nothing. The cost is enormous for the recipients, about 5 man-weeks for each million recipients who spend a second to delete the spam, but the spammer doesn’t have to pay that.

Taste for Makers – How do you make great things?





59. “A lot of the (people applying to be graduate students at MIT) seem smart,” he said. “What I can’t tell is whether they have any kind of taste.” Taste. You don’t hear that word much now. And yet we still need the underlying concept, whatever we call it. What my friend meant was that he wanted students who were not just good technicians, but who could use their technical knowledge to design beautiful things.

60. Your parents taught you to ignore taste. | After dinning into you that taste is merely a matter of personal preference, they took you to the museum and told you that you should pay attention because Leonardo is a great artist.

61. If your job is to design things, and there is no such thing as beauty, then there is no way to get better at your job. If taste is just personal preference, then everyone’s is already perfect: you like whatever you like, and that’s it.

62. Good design solves the right problem. The typical stove has four burners arrange in a square, and a dial to control each. How do you arrange the dials? The simplest answer is to put them in a row. But this is a simple answer to the wrong question. The dials are for humans to use, and if you put them in a row, the unlucky human will have to stop and think each time about which dial matches which burner. Better to arrange the dials in a square like the burners.

63. Humor is related to strength. To have a sense of humor is to be strong: to keep one’s sense of humor is to shrug off misfortunes, and to lose one’s sense of humor is to be wounded by them.

64. Good design resembles nature. It’s not so much that resembling nature is intrinsically good as that nature has had a long time to work on the problem. So it’s a good sign when your answer resembles nature’s.

65. Good design is redesign. It’s rare to get things right the first time. Experts expect to throw away some early world. They plan for plans to change.

66. Nothing is more powerful than a community of talented people working on related problems. Genes count for little by comparison: being a genetic Leonardo was not enough to compensate for having been born near Milan instead of Florence. | At any given time there are a few hot topics and a few groups doing great work on them, and it’s nearly impossible to do good work yourself if you’re too far remove from one of these centers.

Design and Research – Research has to be original. Design has to be good.





67. The difference between design and research seems to be a question of new versus good. Design doesn’t have to be new, but it has to be good. Research doesn’t have to be good, but it has to be new. I think these two paths converge at the top: the best design surpasses its predecessors by using new ideas, and the best research solves problems that are not only new, but worth solving. So ultimately design and research are aiming for the same destination, just approaching it from different directions.

68. Design begins by asking, who is this for and what do they need from it? A good architect, for example, does not begin by creating a design that he then imposes on the users, but by studying the intended users and figuring out what they need.

69. The customer is always right in the sense that the measure of good design is how well it works for the user. If you make a novel that bores everyone, or a chair that’s horrible uncomfortable to sit in, then you’ve done a bad job, period. It’s no defense to say that the novel or chair is designed according to the most advanced theoretical principles.

70. You’re most likely to get good design if the intended users include the designer himself. When you design something for a group that doesn’t include you, it tends to be for people you consider less sophisticated than you, not more sophisticated. And looking down on the user, however benevolently, always seems to corrupt the designer.

71. Even if you’re designing something for the most sophisticated users, though, you’re still designing for humans. It’s different in research. In math you don’t choose abstractions because they’re easy for humans to understand; you choose whichever make the proof shorter. I think this is true for the sciences generally. Scientific ideas are not meant to be ergonomic.

72. All the arts have to pander to the interests and limitations of humans. In painting, for example, all the other things being equal a painting with people in it will be more interesting than one without. It is not merely an accident of history that the great painting of the Renaissance are all full of people. If they hadn’t been, painting as a medium wouldn’t have the prestige it does.

73. To get good design you have to get close, and stay close, to your users. You have to calibrate your ideas on actual users constantly.

74. It’s hard to stay interested in something you don’t like yourself. To make something good, you have to be thinking, “wow, this is really great,” not “what a piece of shit; those fools will love it.”

The Rest

75. The pointy-haired boss miraculous combines two qualities that are common by themselves, but rarely seen together: (a) he knows nothing whatsoever about technology, and (b) he has very strong opinions about it.

76. “Of all tyrannies, a tyranny exercised for the good of its victims may be the most oppressive.” – C.S. Lewis

If you enjoyed these thoughts from Paul Graham, I suggest you read more of his essays online. You can also purchase Hackers and Painters through Amazon if you’d like a little more depth on these subjects.



Image credits go to Inc, theaftershock, and cdevers.