The Almanack of Paul Graham

Hi Ripsters,

I’m a huge fan of Paul Graham.

Paul is the co-founder of Y Combinator and one of the greatest essayist of modern era.

I’ve read I guess 70% of his essays, several of them multiple times (I reached double digits re-readings count on The age of the Essay) and I’ve already shared some of his essays in my Learning Journals with you in the past months.

A good chunk of my life philosophy has been influenced by Paul’s writing. I wish I had his writings available when I was younger. Luckily you, 20-years-younger-than-me reader, have access today to his entire body of work.

Few months ago this crazy idea popped up in my mind: I wanted to write The Almanack of Paul Graham.

Of course I got also inspired by The Almanack of Naval Ravikant, by Eric Jorgensen, mentioned in my WLJ #5. Naval and Paul are both in my personal Olympus. Paul is much more concrete and action oriented, while Naval is my “principles” guide and “virtual mentor”.

As a Naval huge fan, I looked at the success of the Navalmanack with a bit of envy. I should have written that book myself! I was already devouring everything about Naval, and taking personal notes about his Philosophy from sources like: How to Get Rich without being Lucky, Naval on Farnam Street Podcast, Naval on Tim Ferriss Show, Naval on Joe Rogan Experience, Naval’s Tweetstorm on Meditation, and more. Eric did a great job, bringing Naval’s philosophy tot he masses, but as a “scholar” I felt like being spoiled the finale of a season I was still binge watching 🙂

Btw, thanks to this post you’re reading right now, I found that  the Navalmanack is available for FREE as a PDF, Mobi, ePub, and also browsable on the web. This is awesome, seriously, thanks Eric! I’m going to buy the paperback version from Amazon exactly because you made everything available for free (and because I love paper books).

That’s the “business model” I want to incentivize 🙂

Please, make yourself a favor and read this book. It’s free, you don’t have excuses 😉

Few weeks after Navalmanack publication, I felt a urge to write something similar about Paul Graham. My inner voice was telling me to drop everything else and go all-in on this project.

I didn’t react though. I silenced that voice. I just threw this idea on top of the infinite list of the things I would love to work on someday. Time is scarce, ideas are abundant.

Anyway, today I can check off this idea from my infinite TODO list.

Cool! RIP, you finally wrote the book?

No. Paul wrote the Paulmanack himself.

And it’s not a book, it’s just an essay (though 13.6k words long).

In the coming soon section of my latest Monthly Learning Journal I mentioned that I was going to read one of Paul’s newly published Essay: “What I Worked on“. I just finished reading it a couple of days ago, on Pi Day 2021. It took me several sessions, and I guess a total of at least 10 hours of reading, taking notes, thinking and connecting the dots (plus another 10 hours to write, edit, and publish this post).

I was going to add it to the next MLJ, but given the quality and quantity of information shared I decided to write a full dedicated post, where I’m going to quote a lot of passages and adding my own thoughts.

I recommend you to read the original essay first (set at least 30 minutes away for it), then eventually come back here and read my “reaction” post if you’re still curious. I won’t mind if you skipped my post – but please make yourself another favor and read Paul’s essay. Actually, read as many Paul essays as you can, at least those I’ve listed in the “theoretical minimum” 🙂

According to what stage in life you currently are, this is probably going to be either the most or the least useful post you will find on my blog.


…or get out of here asap!

What Paul Worked On

Paul was born in November 1964. He’s currently 56 years old (in early 2021).

Early Drive

Paul’s story begins with his passions as a late teenager, before picking a field to study in college.

Before college the two main things I worked on, outside of school, were writing and programming. I didn’t write essays. I wrote what beginning writers were supposed to write then, and probably still are: short stories. My stories were awful. They had hardly any plot, just characters with strong feelings, which I imagined made them deep.

I can already see several gems in the first paragraph alone. First, Paul didn’t mention “passion”, or “I was passionate about” but “I worked on writing and programming”. I actually “CTRL+F”ed the word “passion” in the entire essay and I got zero results. Good.

I guess he was deeply passionate about both writing and programming, and he’s still writing and programming almost 40 years later. This is of course a “calling” level of passion, but he’s wise enough to recognize that you can’t call it passion at that early stage. Serendipitous encounters with the fields, rewarding iterations, trending topics, a community to share your thoughts and findings, a ton of deliberate practice, hours spent in flow state, good general cognitive abilities and a bit of obsession (or “talent” if you like). Those are the ingredients that build passion. You work, practice, iterate and then you become passionate. Stop waiting for your “passion” to show up before acting on something!

He’s also aware that beginner writers should write “short stories” and not essays. Why? My guess is that a beginner writer has random unstructured ideas, that could fill a few pages. Usually fictional stories that they think they’re original but whose influences from surrounding culture compose 99% of it. And with no philosophical idea to explore. But it’s ok. Writing crappy stories should ignite the positive feedback loop that gets your ball rolling faster: improving your vocabulary, finding your writing voice, playing with your ideas, building complex structures on top of them… Who cares about the quality of your teenager writings?

Now that I think about it, I also wrote short fantasy stories (and a shitload of Dungeons And Dragons adventures and settings for my players group), but I didn’t keep this ball rolling because I let society convince me that I was good at math & science, and my literature scores were just average.

It was Paul, in The Age of the Essay, who opened my eyes:

The most obvious difference between real essays and the things one has to write in school is that real essays are not exclusively about English literature. Certainly schools should teach students how to write. But due to a series of historical accidents the teaching of writing has gotten mixed together with the study of literature.

And so all over the country students are writing not about how a baseball team with a small budget might compete with the Yankees, or the role of color in fashion, or what constitutes a good dessert, but about symbolism in Dickens.

Substitute English with Italian and Dickens with Alessandro Manzoni, and you get the Italian version.

I was so uninterested in literature back then that I never stressed my writing skills hard enough at young age. Of course I don’t think that literature is uninteresting, I just think that it probably is not what a teenager wants to write about.

If I were allowed to write about (and get professional feedback on): “the defensive problems of Roma Soccer Team in the 90s“, “A psychological analysis of the conflict between Shu and Souther in Hokuto no Ken“, or “The use of Yellow, Blue, and Purple candies in Bubble Bubble” I might have become a real writer.


Yeah, what?

Paul’s essay is 13.6k words long. If you vomit 10x more words on every paragraph, explore tangent topics, and talk about yourself I’m gonna cut my veins right now.

Ok ok, do not worry my lazy friend… thanks for reminding me to stay on topic. But this is my Paulmanack, so shut up and listen! It’s going to be less than 8k words long, promised 😀

The equivalent of “writing short stories” in the programming field is of course writing video games, which Paul also did.

Computers were expensive in those days and it took me years of nagging before I convinced my father to buy one, a TRS-80, in about 1980. The gold standard then was the Apple II, but a TRS-80 was good enough.

This was when I really started programming. I wrote simple games, a program to predict how high my model rockets would fly, and a word processor that my father used to write at least one book. There was only room in memory for about 2 pages of text, so he’d write 2 pages at a time and then print them out, but it was a lot better than a typewriter

This is me! His father bought him a computer, and he wrote video games on it (been there, done that).

My early coding explorations helped building skills that snowballed, because I needed no permission and minimal feedback to keep it rolling. And the artifacts, the WIP crappy games I was coding, were themselves positive pushes in the feedback loop.

So I “quit” writing and humanistic disciplines in general to focus on coding.

Luckily for us, Paul kept working on both. He wanted to become an artist, a painter, and he took a PhD in Computer Science by mistake, dreaming about quitting the field at every turn.

His personal story is so inspiring, keep reading!

Philosophy and AI

Paul picked Philosophy in College:

Though I liked programming, I didn’t plan to study it in college. In college I was going to study philosophy, which sounded much more powerful.

It seemed, to my naive high school self, to be the study of the ultimate truths, compared to which the things studied in other fields would be mere domain knowledge.

What I discovered when I got to college was that the other fields took up so much of the space of ideas that there wasn’t much left for these supposed ultimate truths. All that seemed left for philosophy were edge cases that people in other fields felt could safely be ignored.

And he quit philosophy for very practical reasons. Paul wrote a great essay about “How to do Philosophy” in 2007 (ranked 9/10 in my WLJ #2).

So I decided to switch to AI.

Oh come on Paul, stop following me!

Writing, Video Games, AI. And a desire to study the ultimate truths. Same here, that’s me talking.

I need to find patterns, I want to recognize them in myself and in others. I want to anticipate, predict. I want knowledge and wisdom.

I guess the patterns here are:

  • Creativity: writing and coding are two expressions of creativity. Coding at least was creative in the good old days, especially if you worked on your own project for its own sake, without the corruption of money.
  • Curiosity: writing is a doors opener in the realm of knowledge. Philosophy is the ultimate curiosity expression.
  • Control: writing sharpen your thinking. Philosophy attempts to put pieces together. AI extends your control outside of yourself. Writing video games makes you “a God” in the world you created “by definition”.
  • Self Actualization? Transcendence? Immortality? What’s our North Star?

Down to Earth.

While I like to let my mind wander in the abstract world of Platonic ideas, Paul is a very concrete man:

I don’t remember the moment it happened, or if there even was a specific moment, but during the first year of grad school I realized that AI, as practiced at the time, was a hoax […]

That whole way of doing AI, with explicit data structures representing concepts, was not going to work. Its brokenness did, as so often happens, generate a lot of opportunities to write papers about various band-aids that could be applied to it.

I love his accurate description of the paper publishing industry also known as Academic Research 🙂

This was the AI back in Lisp/Prolog era. I had the same feeling back in the early 2000s, and I still feel like we’re overestimating AI/ML these days. I’ll be proven wrong, I’m sure, but yeah… Intelligence Artificial isn’t (said RIP, the Principal Research Engineer for an Academic Institute working on ML).

So I looked around to see what I could salvage from the wreckage of my plans, and there was Lisp. I knew from experience that Lisp was interesting for its own sake and not just for its association with AI.

Jumping from a sinking ship to another. This is a common pattern among smart people. Do not get attached to your first ideas. Paul would say “Keep your Identity Small“. Go deep, learn, view everything from the above, and keep moving.

Alan Watts would also add: “You are under no obligation to be the same person you were five minutes ago

On the technical side of things I can’t relate much to Paul: I’m not a fan of Lisp, simply because I never played with the language. I fell in love for C (and then C++) at first sight, which were de facto standard in the videogame industry when I started coding 30+ years ago.

While Paul loves writing software, he recognized that it has some structural problems:

Any program you wrote today, no matter how good, would be obsolete in a couple decades at best. People might mention your software in footnotes, but no one would actually use it. And indeed, it would seem very feeble work. Only people with a sense of the history of the field would even realize that, in its time, it had been good.

I realized it late. At the peak of my passion for coding I had the ambition of writing “library” code that could last forever. I was more of a library guy than a product guy. For example in my professional Videogame Development career I worked in the Game Engine development, not in final video games implementations.

Maybe if I realized (and accepted) that my artifacts were not going to last forever I’d have either had a better career (due to lower expectations) or I’d have quit way earlier to work on something “more immortal”.

All the code I’ve written at Google has been deprecated, discontinued, thrashed within a few years.

Sisyphus, hold my beer.

Paul, like me, had a strong desire to build something that would last:

While looking at a painting there (Carnegie Mellon University – RIP Note) I realized something that might seem obvious, but was a big surprise to me. There, right on the wall, was something you could make that would last.

Paintings didn’t become obsolete. Some of the best ones were hundreds of years old.

Yes Paul, but does it pay the bills?

And moreover this was something you could make a living doing. Not as easily as you could by writing software, of course, but I thought if you were really industrious and lived really cheaply, it had to be possible to make enough to survive. And as an artist you could be truly independent. You wouldn’t have a boss, or even need to get research funding.

Woo-hoo! Frugality as a solution to do what you love, a healthy dose of repulsion of a normal 9to5 life, and independence as a goal.

Paul, you get the FIRE membership ad honorem!

Well, given that his Net Worth should be in the 9 or 10 digits according to some estimates he “might” get a real Gold or Platinum membership…

Anyway, Paul’s approach to “How to do hat you Love” has been expanded in its own essay. I’ve talked about it in my WLJ #4.

Paul started to take Art classes at Harvard, and dreaming about quitting Grad school and his PhD Program.

I remember when my friend Robert Morris got kicked out of Cornell for writing the internet worm of 1988, I was envious that he’d found such a spectacular way to get out of grad school.

After graduating in AI in spring 1990 (age 25), Paul decided to apply for Art Schools.

Art School and Employment

Fun fact: Paul studied art in Italy, at the Accademia Belle Arti in Florence. They mistakenly sent a response to his application letter back to Cambridge UK instead of Cambridge Massachusetts (US).

Aaaah, what a good taste of Italian Quality! You’re welcome Paul. Luckily for him, he managed to pass the preliminary exam even though he received the invitation letter waaay too late!

Italian bureaucracy did damage his artistic career though. We might have to thank Italy if the world was able to enjoy one of the greatest essayists and angel investors of all times:

Here I was, yet again about to attend some august institution in the hopes of learning about some prestigious subject, and yet again about to be disappointed.

The students and faculty in the painting department at the Accademia were the nicest people you could imagine, but they had long since arrived at an arrangement whereby the students wouldn’t require the faculty to teach anything, and in return the faculty wouldn’t require the students to learn anything.

Welcome to Italy, Paul 🙂

The entire section about his life in Italy is funny to read, but a shame for Italy itself. Shame on us.

I never considered painting, or other visual arts that require manual skills. I’ve always told myself I’m not good at it. Here Paul explains how painting is a way to practice awareness and how it’s a form of meditation:

I liked painting still lives because I was curious about what I was seeing.

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” 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.

This is a feature of brains, not a bug. In everyday life it would be distracting to notice every leaf on every bush.

But 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, just as you can after days of trying to write an essay about something people usually take for granted.

Awesome. Maybe I should add it to my infinite list of things to do 🙂

Sadly, Paul gave up after just a single year:

The Accademia wasn’t teaching me anything except Italian, and my money was running out, so at the end of the first year I went back to the US.

And got a job at Interleaf. But he was a terrible employee:

They wanted a Lisp hacker to write things in it. This was the closest thing I’ve had to a normal job, and I hereby apologize to my boss and coworkers, because I was a bad employee. Their Lisp was the thinnest icing on a giant C cake, and since I didn’t know C and didn’t want to learn it, I never understood most of the software. Plus I was terribly irresponsible.

This was back when a programming job meant showing up every day during certain working hours. That seemed unnatural to me.

I wish I had a fraction of your intellectual honesty Paul. You didn’t let Impostor Syndrome drive your career.

This working experience made him quit and go back to art school, a real art school in the US (fall 1992, age 28)

I moved back to Providence to continue at RISD. The foundation had merely been intro stuff, and the Accademia had been a (very civilized) joke. Now I was going to see what real art school was like.

But alas it was more like the Accademia than not. Better organized, certainly, and a lot more expensive, but it was now becoming clear that art school did not bear the same relationship to art that medical school bore to medicine. At least not the painting department.

Ouch, institutionalized art sucks… like any dream of ours, once dressed the productivity vest, becomes something different, usually worse.

It is really inspirational to see how Paul was able to dance in two completely different worlds while still being able to maintain a “view from the above”, a wise clarity of mind, not letting their respectives echo chambers interfere with his judgement. Now I see where How to Think for Yourself comes from.

In 1993, at age 29, Paul dropped out of art school again. And he was broke. Still a dreamer:

I decided to write another book on Lisp. This would be a popular book, the sort of book that could be used as a textbook. I imagined myself living frugally off the royalties and spending all my time painting.

RoyaltyFIRE, anyone?

He tried painting for a while, in a rent-controlled apartment in NYC, learning directly from Idelle Weber, one of his professors at Harvard and a real artist.

But one day…

Rags to Riches

One day in late 1994 […] there was something on the radio about a famous fund manager. He wasn’t that much older than me, and was super rich. The thought suddenly occurred to me: why don’t I become rich? Then I’ll be able to work on whatever I want.

FatFIRE, anyone?

It’s fascinating for me to acknowledge how much “How to Do what you Love” comes from his own experience. It’s not a speculative essay, it’s been the struggle of his entire life. Thank you Paul, we need more people like you!

Let’s not forget where the story is set:

Meanwhile I’d been hearing more and more about this new thing called the World Wide Web.

LOL. This made me smile 🙂

Paul shares the story of his first failed startup, softly claiming he “invented” web apps:

If I wanted to get rich, here was the next train leaving the station. I was right about that part. What I got wrong was the idea. I decided we should start a company to put art galleries online.

And from the ashes of his first startup, in 1995 he launched Viaweb with Robert Morris and (later) Trevor Blackwell, a precursor of modern eCommerce software.

They got funded $10k for 10% (what a bad deal!), agreement that in a more generous form turned out to become the standard at Y Combinator.

A startup that failed hinting an idea for the next startup, who hinted an idea for the final success. Awesome! In all this, having studied Art helped Paul crafting good looking frontends necessary for the second startup (Viaweb) to live long enough and kind of thrive for a while as one of the first eCommerce platform.

How many have written about the compounding of different skills in different fields? Scott Adams calls it The Talent Stack, James Altucher calls it The Idea Sex… the list is too long.

They sold Viaweb to Yahoo in 1998 for $49 million in Yahoo stocks. I sincerely hope they sold their stocks before the Dot Com bubble exploded!

I hired lots more people, partly because our investors wanted me to, and partly because that’s what startups did during the Internet Bubble. A company with just a handful of employees would have seemed amateurish.

So we didn’t reach breakeven until about when Yahoo bought us in the summer of 1998. Which in turn meant we were at the mercy of investors for the entire life of the company. And since both we and our investors were noobs at startups, the result was a mess even by startup standards.

It’s DotCom bubble babe! Probably most of my readers were too young at that time, but I remember it vividly. I’ve also lost half of my investments back then (8M Italian Lira, i.e. 4k EUR).

Let’s not forget that Luck played a huge role in Paul’s success: finding himself at the right place at the right time. Riding the World Wide Web Wave in 1994, exiting in 1998.

Paul stayed for a year after the acquisition at Yahoo, essentially resting and vesting:

I hung on till the first chunk of options vested, then in the summer of 1999 I left. It had been so long since I’d painted anything that I’d half forgotten why I was doing this.

My brain had been entirely full of software and men’s shirts for 4 years. But I had done this to get rich so I could paint, I reminded myself, and now I was rich, so I should go paint.

We’re all so equal. Deepest desires of humans are very similar. We want to be allowed to be free to do whatever we want. Fun fact: you, yourself, are the final gatekeeper of the freedom you crave for. Most of the “asking for permission” game is played against your own mind.

Financial Abundance

Paul quit Yahoo in 1999:

When I said I was leaving, my boss at Yahoo had a long conversation with me about my plans. I told him all about the kinds of pictures I wanted to paint. At the time I was touched that he took such an interest in me. Now I realize it was because he thought I was lying.

My options at that point were worth about $2 million a month. If I was leaving that kind of money on the table, it could only be to go and start some new startup, and if I did, I might take people with me. This was the height of the Internet Bubble, and Yahoo was ground zero of it.

Holy shit! 2 Millions a month!

I had to read this out loud several times.

It’s a FIRE amount, each month.

And Paul left everything on the table, with no regrets. Telling his boss “listen boss, I don’t need 2M a month. I want to paint apples, pears, and a watermelon for the rest of my life“. This reminds me of my final conversation with my last manager at Google, discounted by two orders of magnitude in terms of money 🙂

How did Paul’s n-th attempt at painting go?

But I really was quitting to paint, and I started immediately. There was no time to lose. I’d already burned 4 years getting rich.

Now when I talk to founders who are leaving after selling their companies, my advice is always the same: take a vacation. That’s what I should have done, just gone off somewhere and done nothing for a month or two, but the idea never occurred to me.

So I tried to paint, but I just didn’t seem to have any energy or ambition.

Let me try to humbly diagnose this: a mix of The Optionality Trap and exhaustion. Paul maximized options in his life by “trying to get rich and then doing what he loved”.

Neil Soni wrote in The Optionality Trap:

And over the course of a lifetime, this optionality maximization mentality turns us into habitual option collectors and prevents us from reaching our goals.

I’m sorry to inform you all that there’s no solution. Either you play the lottery ticket and you’re lucky, or you play it safe and might never go all-in on your dreams. We’re reaching the boundaries of what could be done in just a short lifetime.

Anyway, do we want to tag Paul’s failure to become a great artist as a real failure? Of course not, he’s done better than 99.999+% of the world population!

Let’s keep going.

In the spring of 2000, I had an idea. It was clear from our experience with Viaweb that web apps were the future. Why not build a web app for making web apps?

Actions become passions, not vice versa.

While he romanticized about seeing himself as a painter, his brain has been too much in contact with startups, Internet and the WWW, and money.

He’s now an “idea guy”, back when ideas were not so abundant as they are today.

Our surroundings shape us more than we like to think. It’s an effect similar to hedonistic adaptation. We become what we do, who we hang out with, where we live.

I’ll just spend ten years in Switzerland to accumulate money, then I’ll move back to Italy

I’ll just keep working for another ten years then I can do whatever I want

Yeah, sure.

I got so excited about this idea that I couldn’t think about anything else. It seemed obvious that this was the future.

He was close to launch another startup, a precursor of SaaS platforms, but…

But about halfway through the summer I realized I really didn’t want to run a company — especially not a big one, which it was looking like this would have to be.

I’d only started Viaweb because I needed the money. Now that I didn’t need money anymore, why was I doing this?

If this vision had to be realized as a company, then screw the vision. I’d build a subset that could be done as an open source project.

He then built Arc, a Lisp dialect.

After a speech at a Lisp conference he put the slides and talk notes on his website, and got a 30k pageviews spike.

He was not writing essays yet.

The Age of the Essay

If I write something and put it on the web, anyone can read it.

That may seem obvious now, but it was surprising then. In the print era there was a narrow channel to readers, guarded by fierce monsters known as editors. The only way to get an audience for anything you wrote was to get it published as a book, or in a newspaper or magazine. Now anyone could publish anything.

In 2001 he started writing the best essays you can find on the internet, including the incredible The Age of the Essay. While not exactly being a blog, we can say that he was one of the pioneers of internet writing.

In the print era, the channel for publishing essays had been vanishingly small. Except for a few officially anointed thinkers who went to the right parties in New York, the only people allowed to publish essays were specialists writing about their specialties.

There were so many essays that had never been written, because there had been no way to publish them. Now they could be, and I was going to write them

This essay is a museum of creativity over the internet! I’m having so much fun reading and commenting it. I can’t thank you enough Paul 🙂

I’ve worked on several different things, but to the extent there was a turning point where I figured out what to work on, it was when I started publishing essays online. From then on I knew that whatever else I did, I’d always write essays too.

Writing brings many superpowers. The most powerful one is probably “sharpening your Thinking”.

By writing about things you don’t know (yet) with a curiosity attitude, you explore and prototype working on what might interest you.

Writing is the ultimate Deliberate Practice tool.

One of the most conspicuous patterns I’ve noticed in my life is how well it has worked, for me at least, to work on things that weren’t prestigious.

Paul also wrote about how to not chase prestige in the How to do what you Love essay, that I already mentioned several times.

It’s not that unprestigious types of work are good per se. But when you find yourself drawn to some kind of work despite its current lack of prestige, it’s a sign both that there’s something real to be discovered there, and that you have the right kind of motives.

Impure motives are a big danger for the ambitious.

A single sentence by Paul summarized a 5k words RIP Transparency Manifesto.

Ok, time to talk about the birth of Y Combinator.

Y Combinator and Hacker News

Of course it happened “by chance”, but at this point he built his luck enough that opportunities were chasing him, and not the other way around. To improve his writing quality he gave talks, and one of this talks were about “how to start a startup“.

This talk/essay kind of evolved into Y Combinator.

This reminds me of the rarest kind of luck, the one that according to Naval Ravikant finds you.

Yes, Paul got lucky a couple of times early on his career.

A bit of “blind luck” at the beginning (especially in the form of being at the right place at the right time), a lot of “persistence luck” during his startup years, but at this point he started attracting luck.

Luck of others became luck of him as well.

In March 2005, Paul and his three partners (Jessica Livingston, Trevor Blackwell, and Robert Morris) founded Y Combinator, the most famous (the first?) startup accelerator and one of the top Angel/Venture Capital firms in the world.

They gave birth to Reddit, Stripe, Airbnb, DoorDash, Coinbase, Instacart, Dropbox, GitLab, Substack, and Twitch to mention some.

There are multiple components to Y Combinator, and we didn’t figure them all out at once.

The part we got first was to be an angel firm. In those days, those two words didn’t go together.

There were VC firms, which were organized companies with people whose job it was to make investments, but they only did big, million dollar investments.

And there were angels, who did smaller investments, but these were individuals who were usually focused on other things and made investments on the side.

And neither of them helped founders enough in the beginning.

We knew how helpless founders were in some respects, because we remembered how helpless we’d been.

This seems obvious, “the norm” today. But just 15 years ago there were no “startup incubator”. They kind of coined the term.

We’d use the building I owned in Cambridge as our headquarters. We’d all have dinner there once a week — on Tuesdays, since I was already cooking for the Thursday diners on Thursdays — and after dinner we’d bring in experts on startups to give talks.

Yeah, In forgot to mention that he used to host interesting people and their friends in a second-degree dinner habit at one point of his life.

Now I need a time machine more than ever 🙂

Fairly quickly I realized that we had stumbled upon the way to scale startup funding.

Funding startups in batches was more convenient for us, because it meant we could do things for a lot of startups at once, but being part of a batch was better for the startups too.

It solved one of the biggest problems faced by founders: the isolation. Now you not only had colleagues, but colleagues who understood the problems you were facing and could tell you how they were solving them.

I have this bittersweet feeling when I read about startups, especially startups in the “good old days” after the DotCom bubble. I’ve never worked at one, even though I think I’m a startup person.

If I’ll leave my tech career for good, not having tried to found a startup would be my biggest regret.

Never say never though 🙂

I had not originally intended YC to be a full-time job.

I was going to do three things: hack, write essays, and work on YC. […]

In the summer of 2006, Robert and I started working on a new version of Arc. This one was reasonably fast, because it was compiled into Scheme. To test this new Arc, I wrote Hacker News in it. It was originally meant to be a news aggregator for startup founders and was called Startup News, but after a few months I got tired of reading about nothing but startups. Plus it wasn’t startup founders we wanted to reach. It was future startup founders. So I changed the name to Hacker News and the topic to whatever engaged one’s intellectual curiosity.

Hacker News (HN) is still, today, the main source of information for Tech topics in general. It’s like a giant tech/startup subreddit.

When my own career was taking off, HN, StackOverflow, and r/programming were my places.

The Last Cool Thing You Do

Paul worked incredibly hard on YC for several years, and in 2010 Robert Morris, friend, co-founder of YC, and renown hacker (in both the good and the bad meaning of the term) suggested him:

Make sure Y Combinator isn’t the last cool thing you do.

This speaks to my heart as well. Commit all of yourself to what you love right now, but please, do respect your future lifetimes.

It was true that on my current trajectory, YC would be the last thing I did, because it was only taking up more of my attention. It had already eaten Arc, and was in the process of eating essays too. Either YC was my life’s work or I’d have to leave eventually. And it wasn’t, so I would.

In October 2013 (Paul close to turn 49), with the benevolence of the other founders, Paul offered the presidency of YC to Sam Altman.

Paul still works few hours a week with founders but he’s not deeply involved with YC anymore.

I must admit that I didn’t know Paul was not leading YC anymore. I discovered it thanks to this essay.

What should I do next? Rtm’s advice hadn’t included anything about that. (RIP Note: RTM is Robert Tappan Morris, his co-founder at ViaWeb and YC) I wanted to do something completely different, so I decided I’d paint.

I wanted to see how good I could get if I really focused on it. So the day after I stopped working on YC, I started painting. I was rusty and it took a while to get back into shape, but it was at least completely engaging.

Still chasing his teenager dreams. It is romantic, it really is. But it’s the dream of a different, younger Paul. Not his anymore.

He had fun for a while though:

I spent most of the rest of 2014 painting. I’d never been able to work so uninterruptedly before, and I got to be better than I had been. Not good enough, but better.

Then in November, right in the middle of a painting, I ran out of steam. […]

I stopped working on it and cleaned my brushes and haven’t painted since.

Lao Tzu is credited with the quote “When I let go of what I am, I become what I might be“.

I think it fits Paul perfectly.

Attention is a zero sum game. If you can choose what to work on, and you choose a project that’s not the best one (or at least a good one) for you, then it’s getting in the way of another project that is.

And at 50 there was some opportunity cost to screwing around.

Oh shit, this hit me like a punch in the face.

There’s no time to waste. Once you “solved” your money problems you must work only on what matters most.

Derek Sivers would say it’s either Hell Yeah or No.

I started writing essays again, and wrote bunch of new ones over the next few months. I even wrote a couple that weren’t about startups.

… and we’re so grateful 🙂

Then in March 2015 I started working on Lisp again.

Writing essays, and writing software for his own pleasure, in the least corporate way possible. He’s definitely living the professional life of my dreams.

Many 20-years-younger-than-me readers reached me out to tell me I’m an inspiration for them. It’s an honor, but I don’t feel like I’m worth being put on a (small) pedestal.

I’m only geometrically halfway between you, average Italian young adult, and people like Naval and Paul, whose accomplishments (and Net Worth) are few orders of magnitude mine.

Maybe if Paul would accidentally find this post he’d think I’m exaggerating with my idolatry. He’d probably think that he’s nothing special, that he’s just geometrically halfway between me and Elon Musk for example.

Hey Paul, if you’re reading this: Elon’s nowhere near to you in my Olympus!

(Wait Elon: I didn’t mean Olympus Mons… please, don’t send the Starman wandering on your Roadster to crash into the surface of Mars for the sake of winning this fake competition, please)

It took 4 years, from March 26, 2015 to October 12, 2019. It was fortunate that I had a precisely defined goal, or it would have been hard to keep at it for so long.

I wrote this new Lisp, called Bel, in itself in Arc.

We’re close to the end of this long trip.

Paul reminds us about the importance of Deep Work, and the dangers of Multitasking:

I had to ban myself from writing essays during most of this time, or I would never have finished. In late 2015 I spent 3 months writing essays, and when I went back to working on Bel I could barely understand the code. Not so much because it was badly written as because the problem is so convoluted. When you’re working on an interpreter written in itself, it’s hard to keep track of what’s happening at what level, and errors can be practically encrypted by the time you get them.

Luckily for us, the essays he’s written during his ban were still extremely good.

But he’s right: you need to clarify your goals, trim the unnecessary, and focus. Maybe I’m doing too many things, none with the required quality. Thanks once again Paul, I’ll think about it.

Working on Bel was hard but satisfying. I worked on it so intensively that at any given time I had a decent chunk of the code in my head and could write more there.

I remember taking the boys to the coast on a sunny day in 2015 and figuring out how to deal with some problem involving continuations while I watched them play in the tide pools.

It felt like I was doing life right.

I remember that because I was slightly dismayed at how novel it felt. The good news is that I had more moments like this over the next few years.

Flow State becoming permanent state of being. This is amazing!

What To Do Next

In the fall of 2019, Bel was finally finished. […] Now that I could write essays again, I wrote a bunch about topics I’d had stacked up. I kept writing essays through 2020, but I also started to think about other things I could work on.

How should I choose what to do? Well, how had I chosen what to work on in the past?

I wrote an essay for myself to answer that question, and I was surprised how long and messy the answer turned out to be. If this surprised me, who’d lived it, then I thought perhaps it would be interesting to other people, and encouraging to those with similarly messy lives. So I wrote a more detailed version for others to read, and this is the last sentence of it.

And I’m thankful you wrote this amazing essay Paul, which is jumping directly into my Top10 list, among the others listed in the final paragraph of this post.

Fun fact (that I discovered only thanks to this rabbit hole) is that Jessica Livingston, one of YC co-founder, is also Paul’s wife and mother of their children.

I happen to have read few chapters of Founders at Work without knowing the author was Paul’s wife 🙂

That’s it!

I hope you enjoyed this trip into one of the most brilliant minds we have the pleasure to share our short ride on this rock around the Sun with.

Here’s a 2014 guest lecture at Stanford University in the How to Start a Startup course by Sam Altman (soon to become Y Combinator President). This lecture became Paul’s “Before The Startup” popular essay. Enjoy:

Paul Graham’s Theoretical Minimum

If you want to start reading Paul’s essays I recommend the following ones, split by category.

Creativity and writing:

Life Design

Critical Thinking:


Yeah, some of the links point to my previous dissertation on the relative essays, but from there you can find the right link to Paul’s website.

It’s been an amazing trip, and I had a lot of fun!

I hope you enjoyed it as well 🙂



  1. Wow, this is great! I need to read many of these essays. It looks like PG has hacked how to live life!

    Also, just to keep the record straight: the whole “almanack” concept (i.e the Navalmanack) derives from “Poor Charlie’s Almanack” (i.e all the wisdom of Charlie Munger) which itself was a reference to “Poor Richard’s Almanack”, written by Benjamin Franklin 😉

    1. I knew about the Poor Charlie’s Almanack, I didn’t know about the Poor Richard’s Almanack!
      I thought everything started with Mickey Mouse Almanack 😀

  2. This is terrific… rabbit hole 😂 I have started reading this article two hours ago and have not finished yet. I did not know who Paul Graham was and I now I already read so many of his essays. I especially loved The Age of the Essay, Life is Short, What You’ll Wish You’d Known. And I must admit that the 10-year-old me would have devoured an essay on “The use of Yellow, Blue, and Purple candies in Bubble Bubble”, too.
    I have 5 more essays waiting for me on my browser tabs.
    Thank you for writing and sharing this. It has been an incredibly sobering trip 🙂

      1. I read it. And I have mixed feelings about it. It is one of those piece of work you know you have to let sink in, and re-think about days (months? years?) later.

        My father always told me that “When you love your job, you won’t work a day in your life”. and he truly loves what he does. Despite this kind of upbringing, I have a different approach to work life. I think that anything I truly enjoy doing will be spoiled if money ever get involved. I kinda liked Mark Manson take on it (Screw Finding You Passion).
        What do you think?

        Anyway, I know I will reflect upon this topic for a long time from now on xD
        Thanks again for sharing. (And I really appreciated your notes on the essay!)

  3. You should be aware that Mr. Graham is the guy who took a vendetta against your Google ex-colleague Michael O. Church just for having a different opinion on the VC world. He managed to ban him from a couple of platforms like Quora, etc. and made his life miserable when looking for employment. While I don’t agree with Michael Church on many topics, I think Michael is a talented decent guy and you need to be a psychopath to give him such a treatment.

    I used to read Mr. Graham books when I was younger, I admit he is a talented writer. Now after a certain amount of life experience I find most of his text platitudes or even untruthful given his course of actions. And yes, Michael is right about the VC world. I speak here from my own experience.

    1. I know nothing about Graham vs Church, and I don’t expect anyone in particular to be Jesus Christ. If the two guys had a fight over the internet… well… whatever!

      1. Well, you know now. Mind you the fight got from the internet to the real world. To make this happen it certainly doesn’t need a Jesus Christ, but a psychopath.

  4. This is great. I’m a huge fan of Paul’s writings.
    I ‘m sure that in my 20s I would have reacted differently to Paul’s (and Naval’s) word. And probably lost many of the messages.
    I’m glad I found their writings now that I’m in my 40s. To find what you look for you should know what you need. And you appreciate what you find when you need it, and I was exactly expecting these words now, in my midlife crisis and halfway in my FIRE journey.

    Thanks for your effort.
    What I am missing right now is : “what do I do now with this knowledge and how does a terrible procrastinator like me apply that to my life decisions now that I’m paralyzed by fear of the unknown and by choice paralysis with all the projects and ideas I have in my head? Where to point my focus?”
    The obstacle is in our head, and probably the right answer is already there too, I know, and we fear to say it aloud, but maybe sometimes we just need a gentle push from behind from someone, to start going in a new direction, and I feel that belonging to a community of like minded people can help a lot.

    1. This is a very good point. I like to imagine that I’d have benefited by having these writings available 20 years ago but maybe I wouldn’t 🙂

      About procrastination I know what you mean. Having this blog and other creative outlet is my best antidote to chronical procrastination.

      Create. Do stuff. Don’t aim to perfection, just get started. Feedback will guide you somewhere.

  5. I’m a big fan of Paul since i cofounded my first startup! (My exit strategy for FIRE)

    Hoping an Y combinator style since when i became an angel investor and mentor in early stage/seed startups in Italy

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