Subscribe
Share
Share
Embed
Find your work.
Welcome to Craftsmith, a podcast about people doing work they love so you can too. This episode is a Craftsmith Letter to Paul Graham. It's a thank you for his essays and also an invitation. Paul, if anything here rings true, I'd love to record an episode together. Twenty five years ago, venture capital worked like this.
Speaker 1:Founders walked Sandhill Road in Palo Alto pitching their startups. VCs sat on boards. Deals took months, and anyone who got funded gave up control of their company. You needed experience, connections, and a polished pitch deck to have any shot. Then a hacker who studied painting in Florence started funding college programmers out of his living room in Cambridge, Massachusetts.
Speaker 1:He gave them small checks, let them keep control, and told them to make something people want. That was why Combinator, co founded by Paul Graham. It became one of the most valuable investment firms in technology history as an early backer of Airbnb, Stripe, Dropbox, Coinbase, Instacart, and countless others. By YC's own estimate, a trillion dollars in value have flowed from an idea that in theory anyone could have had. So why Paul?
Speaker 1:Everyone else looked at young programmers and saw an experience. They looked at small checks and leaving founders in control, and they saw bad economics and unnecessary risk. Paul looked at the same reality and saw what was actually there. I think I might know why. The answer traces back to his years as a painter, studying art in Florence and Providence while everyone else was following an old playbook.
Speaker 1:Here is my letter to Paul Graham. Paul, I want to talk about your painting years. Your readers know you as a programmer, an essayist, and an investor. The painting gets treated as a detour, almost the way people mention that Einstein played the violin. They tend to overlook the years at RISD and the Academia de Belliarty in Florence.
Speaker 1:Painting still lifes, learning to render light on canvas. You said, while I was a student at the Academia, I started painting still lifes in my bedroom at night. These paintings were tiny because the room was and because I painted them on leftover scraps of canvas, which was all I could afford at the time. Why still lifes? He said, I liked painting still lifes because I was curious about what I was seeing.
Speaker 1:Those years matter because I think that curiosity taught you a skill you've been applying ever since. They taught you how to see. In your essay, What I Worked On, you wrote something that seems like a bigger deal than it first appears. In everyday life, we aren't consciously aware of much we're seeing. Most visual perception is handled by low level processes that merely tell your brain that's a water droplet.
Speaker 1:Without telling you details like where the lightest and darkest points are or that's a bush without telling you the shape and position of every leaf. You're saying that your brain takes shortcuts. It shows you a symbol for the thing, not the thing itself. For example, when you look at a tree, you see your brain's shortcut for tree, a green blob on a brown stick. That symbol lets you walk around without bumping into trees, but it's not what's actually there.
Speaker 1:Painting doesn't work that way. You said, when you have to paint something, you have to look more closely. And when you do, there's a lot to see. You can still be noticing new things after days of trying to paint something people usually take for granted. That's the skill.
Speaker 1:Looking more closely. And painting forces you to override your brain's shortcuts because you can't paint a tree by drawing your idea of a tree. To paint one, you have to see the actual light and shadow. Where the highlights land, how the bark shifts color, or the way that the leaves layer over each other. You have to see what's actually there.
Speaker 1:Years later, you wrote about evaluating paintings in museums. How much would I pay for this if I found it at a garage sale, dirty and frameless, and with no idea who painted it? So strip away context, strip away prestige. If you take away the gold frame in the museum wall and the plaque declaring that this is a masterpiece, what do you actually see? That's what you called the garage sale test.
Speaker 1:The purest expression of the skill that you learned painting. Seeing past the brain's shortcuts, past the abstraction to see what's actually there. When you discovered Lisp, you found a programming language that works like painting does. Most languages have different syntax for different things like curly braces for blocks or semicolons for statements. Lisp uses the same structure for everything.
Speaker 1:It's just parentheses and symbols all the way down. You said, learning Lisp expanded my concept of a program so fast that it was years before I started to have a sense of where the new limits were. Lisp lets you see the shape of a program. The structure isn't hidden behind decoration. You wrote a whole book about this called On Lisp.
Speaker 1:You said you learned more by writing that book than ever before because writing it forced you to see what was actually going on. When you built Vioweb in 1995, the idea came to you on a mattress. One morning as I was lying on this mattress, I had an idea that made me sit up like a capital l. What if we ran the software on the server and let users control it by clicking on links? Back then, software was something you installed on a desktop, but you saw what was actually there.
Speaker 1:You went on, a couple days later on August 12, we had one that worked. The UI was horrible, but it proved you could build a whole store through the browser. Your essays work the same way. You've said you write to figure things out. Each essay takes something people take for granted and picks it apart until you can see what's actually there.
Speaker 1:Then you show us what you see. You've said many discoveries have come from asking questions about things that everyone else took for granted. That's what your essays do. They ask questions about things we've stopped looking at. We all know what a startup is, but you ask what is a startup really?
Speaker 1:What distinguishes it from a small business? What do successful ones have in common? You paint the concept until you can see its actual shape. When you taught founders at Y Combinator, your core advice about finding startup ideas was about seeing. You said, the way to get startup ideas is not to try to think of startup ideas.
Speaker 1:It's to look for problems, preferably problems you have yourself. That's the painters I applied to entrepreneurship. Don't start with a symbol in your brain for startup idea. Start by looking at problems in your own life. What annoys you?
Speaker 1:What's broken? Just see what's actually there. I think this is why you saw the y combinator possibility when nobody else did. Everyone else looked at startups and saw the category. The pitch decks, the experienced founders taking large checks, the board seats.
Speaker 1:This was an abstraction of how startups were supposed to work. You looked past the category to what was actually there. Talented young programmers who needed small amounts of money, advice from people who'd done it before, and the freedom to retain control. The idea came together on a walk home from dinner. You've said, as Jessica and I were walking home from dinner on March 11 at the corner of Garden And Walker Streets, these three threads converged.
Speaker 1:You decided that you'd start your own investment firm. You got 225 applications in that first batch, picked eight to fund, and invested $6,000 per founder in return for 6%. That first batch included Reddit, the future founders of Twitch, and Sam Altman. The painter's eye, that is what let you see what everyone else missed. In How to Do Great Work, you turned your painter's eye to finding work you love and you saw something startling.
Speaker 1:How many even discover something they love to work on? A few 100,000 perhaps out of billions. Paul, if that's true, it's a tragedy. That's only a tiny fraction of people who ever discover work they love. And you don't say this with resignation.
Speaker 1:Like all questions you pose in your essays, you frame it as a puzzle. Why so few? Your answer spread across a decade of essays centers on interest. You've said interest is much more evenly distributed than ability. This is a profound observation.
Speaker 1:Ability follows a curve. Most people cluster near the middle, fewer at the extremes. But interest is different. Interest is as varied as fingerprints. There are more types of interests than types of talent.
Speaker 1:So your particular interests are unlikely to match anyone else's. You wrote about this in your essay, The Bus Ticket Theory of Genius. Some people have an obsessive interest in the history of bus tickets. Most people would find that boring. But for the people fascinated by old bus transfers, that interest is real and it's utterly their own.
Speaker 1:You've said, it can be harder to discover your interests than your talents. There are fewer types of talent than interest and they start to be judged early in childhood. Whereas interest in a topic is a subtle thing that may not mature till your twenties or even later. That's the problem. Talent gets tested early.
Speaker 1:There's a handful of school subjects and a handful of sports. If you're good at any one of those, you'll find out. But there are far more types of interest than the things that schools measure. If your genuine interest isn't on that curriculum, you might never get the signal that it's yours. Perhaps where your painter's eye matters most is in your warnings about signals that look like interest, but aren't.
Speaker 1:You said, are you really interested in x? Or do you want to work on it because you'll make a lot of money? Or because other people will be impressed by you? Or because your parents want you to? These are the brain's shortcuts applied to careers.
Speaker 1:Prestige is what other people find impressive, which is not the same as what interests you. Money is a nice byproduct of good work, but it doesn't pull you into the work. And what your parents want is their desire for your security projected onto you. It's not yours. All of those can feel like genuine interest in the moment, but they're not.
Speaker 1:They're just noise. Finding work you love requires stripping those things away to see what's actually there. It's like the garage sale test applied to careers. What would you work on if no one was watching? What pulls you when you don't expect anyone to applaud?
Speaker 1:You wrote about a friend who became a doctor. A friend of mine who is a quite successful doctor complains constantly about her job. When people applying to medical school ask her for advice, she wants to shake them and yell, Don't do it! How did she get into this fix? In high school, she already wanted to be a doctor.
Speaker 1:And she is so ambitious and determined that she overcame every obstacle along the way including unfortunately not liking it. Now she has a life chosen for her by a high school kid. That line devastates me. She is living a life designed by a teenager who couldn't possibly have known what being a doctor actually meant. In other words, she painted from the symbol instead of from observation.
Speaker 1:And by the time she could see reality, she was already trapped by the years she'd invested. You picked apart the problem of finding work you love, looked at it until you could see what's actually there, and then you showed us what you saw. Start by producing. You wrote, always produce is also a heuristic for finding the work you love. If you subject yourself to that constraint, it will automatically push you away from things you think you're supposed to work on towards things you actually like.
Speaker 1:Always produce will discover your life's work the way water with the aid of gravity finds the hole in your roof. I love that metaphor. Water doesn't plan its path. It just follows gravity. If you force yourself to keep producing, eventually your work will naturally flow towards the places you're generally interested.
Speaker 1:Because you can't sustain fake interest over the long run. You've also said to follow curiosity. Curiosity is the best guide. Your curiosity never lies, and it knows more than you do about what's worth paying attention to. But how do you know when it's real?
Speaker 1:You answered, what are you excessively curious about? Curious to a degree that would bore most other people. That's what you're looking for. Don't worry if you find you're interested in different things than other people. The stranger your tastes in interestingness, the better.
Speaker 1:If you're interested, you're not a stray. You also say to start with projects. Big things start small. The initial versions of big things were often just experiments or side projects or talks, which then grew into something bigger. Yuanan.
Speaker 1:Great things are almost always made in successive versions. You start with something small and evolve it. And the final version is both clever and more ambitious than anything you could have planned. Let the path grow out of the prod on the path to some goal you're supposed to have. Paths can bend a lot more than you think.
Speaker 1:So let the path grow out of the project. The most important thing is to be excited about it because it's by doing that you learn. You don't plan your way to work you love. You see your way there, one project at a time. At the end of your essay on doing great work, you speak directly to your readers.
Speaker 1:If you've made it this far, you must be interested in doing great work. And if so, you're already further along than you might realize because the set of people willing to want to is small. Out of billions, most people never even ask the question. You've also said, finding work you love is very difficult. Most people fail.
Speaker 1:Even if you succeed, it's rare to be free to work on what you want till your thirties or forties. But if you have the destination in sight, you'll be more likely to arrive at it. If you know you can love work, you're in the home stretch. And if you know what work you love, you're practically there. You learn to see what's actually there.
Speaker 1:Your essays have been teaching that skill ever since. Paul, behind everything you've been doing for decades, you've been teaching people to see. You applied that skill to programming and saw what code could become when you stopped thinking about syntax and looked at structure. You applied it to essays and saw the actual shape of ideas everyone else takes for granted. You applied it to startups and saw what founders actually needed.
Speaker 1:You applied it to founders and saw who people actually were, not what their credentials said about them. In researching this episode, I came across a passage of yours that I can't get out of my head. It goes, most of the time I'm worried and puzzled. Worried that the essay will turn out badly and puzzled because I'm groping for some idea that I can't see clearly enough. You have moments of happiness when things work out, but they don't last long because then you're on to the next problem.
Speaker 1:So why do it at all? Because to the kind of people who like working this way, nothing else feels as right. You feel as if you're an animal in its natural habitat. Doing what you are meant to do. Not always happy maybe, but awake and alive.
Speaker 1:You turned your painter's eye on what it actually feels like to do work you love and described it so clearly that the rest of us know when we found it. Before your essays, I didn't even know what to look for. Paul, if this letter finds you, I'd love to talk about what you see. This has been a Craftsmith Letter to Paul Graham. If you saw yourself in that story, here's Paul's test.
Speaker 1:What are you excessively curious about? Curious to a degree that would bore most people. And what's a small project you can start this week to explore that curiosity? That's what you're looking for. If you think Paul should hear this letter, you can help me deliver it.
Speaker 1:Send him this episode. I'll put links to his site and socials in the show notes. And if you want to find out whether this letter reaches him and what happens if it does, follow Craftsmith wherever you're listening to this podcast. I'm Bill Allred. Thank you for listening to Craftsmith.