🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

Something that seems to make some people extremely uncomfortable:

A lot of folks like comic book movies.

And I am one of those people.

We like to clap and dress up, and we cry when heroes fall. We like to have a good night out at the movies, and we like that night to involve various caped demigods, mutants, and wizards. We find it inspiring, uplifting, and ridiculously and unapologetically exciting.

In short, we love watching the Avengers.

But there is a certain incredibly angry kind of person on the internet who sees our joy and feels nothing but impotent rage. They crash out, and they call us dumb, and they kick and scream about how comic book movies are trash and culture is dead, and we’re all garbage people for consuming garbage content.

They post long Twitter threads and ranting YouTube videos looking down on the “basic bitches” who enjoy mainstream pop culture.

If you ask me, they don’t seem like happy people.

And, well - I don’t think the movies are actually the problem.

I don’t think any of the juggernaut superhero franchises are the problem.

I don’t think my happiness, or the happiness of anyone who enjoys watching Iron Man or Captain America or Shang-Chi or the other paragons of the pantheon, is the problem either.

No: If your reaction to popular things is to lose your proverbial shit and rend your proverbial garment, the problem is very clearly and very simply with you.

If my joy makes you hopping, steaming mad, you should look inside the cave instead of looking at everyone else and pointing the finger of doom out of your own emotional dysregulation and your own inability to articulate and deal with your Big Feelings.

My Hot Take Is That Joy Is Not a Crime.

People are allowed to like things.

People are allowed to have fun.

We’re allowed to be moved by movies about heroic figures wearing red capes.

We’re allowed to love big dumb space operas.

To treat joy as if it’s the sole product of a weak mind, and to treat fun like some form of moral failure is a moral failure in itself.

Robert Louis Stevenson said, "There is no duty we so much underrate as the duty of being happy. By being happy, we sow anonymous benefits upon the world, which remain unknown even to ourselves."

Fandom, the act of enjoying something and becoming part of a tribe of people who enjoy that thing, is not a disease. And your personal taste does not equate to an IQ test that determines whether or not somebody is enlightened or a member of the Sheep Class™️.

My joy doesn’t actually need your approval.

It doesn’t need anybody’s approval.

If I’m inspired by something, I have every right to be, and nobody has any mandate or God-given right to make me feel ashamed by it; and if I’m happy and no one got hurt and you’re still angry, that anger is your fault and your responsibility. It’s certainly not mine.

Taste is incredibly personal and weird. It’s shaped by your life, by your memory, and by your tribe. But it’s not a weapon, and it’s not a crown; it’s not proof of a good soul or an elevated IQ. And it’s certainly not a reason to spit on people because they like different things than you.

It’s only the snob who says, “I like better thing, therefore I’m smarter than you, and you’re a plastic person and your fun is fake.”

And the snob is very rarely happy.

Liking serious films doesn’t make you noble, and liking old books doesn’t make you deep. Hating Marvel will not make you either a prophet or the savior of modern culture.

In fact, publicly and loudly hating any popular thing won’t actually make you free; sometimes it just makes you incredibly isolated. You might take some solace in feeling awfully superior in your isolation, but it won’t make you any less lonely.

A far better stance is to like what you like and let others like what they like.

You don’t have to turn your taste into an exclusive club, and you don’t have to beat the happy people around you to death with that club.

If you’re angry at a movie, it’s worth asking, am I actually angry or am I tired, lonely, and bored?

More often than not, rage is simply a mask for grief and fear and envy. It’s easier to feel anger than it is to admit that you miss your own sense of wonder and you don’t know how to get it back, or you desperately want to fit in with the mainstream and you don’t know how, and it makes you feel angry and left out.

There’s a hidden wound here; why do they get to enjoy this thing? Why don’t I feel anything? Why is my world not made for me? Why is my taste not popular?

It’s a form of projection.

You’re projecting your emptiness onto our excitement, your bitterness onto our popcorn, and your contempt onto our night out. If the joy of others feels like an insult to you, the wound is yours entirely, and the wound is yours to heal.

Something Being Popular Is Not the Same Thing as It Being Bad.

Just because something has mass appeal doesn’t make it empty or soulless.

Just because something is small and limited and exclusive doesn’t make it pure.

Sometimes a popular thing is bad, sure, but sometimes a popular thing can just be popular.

It can be fun, and mean little, and that’s okay too.

It can bring people together, bridge gaps, and give folks something to have in common.

Comic book movies can be corporate, formulaic, loud, and stupid, sure. But they can also be fun and moving and, in a way, beautiful and meaningful to some folks.

Two things can be true. Studios can want money, and viewers can actually feel real joy. A brand machine can be huge, and human moments can still be human.

It’s an incredibly lazy criticism to dismiss something because it’s popular, it’s a franchise, it’s for children, or it’s not real cinema. A much better criticism is to ask, what worked and what didn’t work? What did the movie do and what it failed to do? Why do people care?

You can hate the machine all you want, but hating the person smiling in a seat because their taste doesn’t match yours is petty and small-minded.

It’s a caveman-level scarcity brain mindset to think that my joy can only exist by stealing from yours. If you truly believe that the success of a mainstream movie crowds out your movie, that the flourishing of a fandom lowers the culture, and that the broader tastes of the Marvel fandom ruin the world, you’re welcome to keep on keeping on; but none of it is actually based on reality.

A great many joys can exist at the same time. A great many stories can exist at the same time. There can be infinite rooms and infinite fires burning, and you’re allowed to pick and choose. You can watch an art film if you want. You can read a hard book, and you can ignore the superhero movies. You can make your own thing. You can touch grass. You can leave people alone if they’re experiencing joy.

You don’t need to mock the fans and police what they love and rage post and perform disgust.

You don’t need to audit and censor everyone else’s taste.

The far healthier move is to guard your own attention and feed your own mind. If you want to build your own culture, do so. If you want to find your own people, do so. But if you can only focus on and expend your energy on stuff you hate, you’re going to have an incredibly miserable life.

If you truly hate something, if it awakens nothing but loathing, the best thing to do is to walk away, not to stand there pointing at it.

You Can Let People Have Dumb, Sacred Things.

Humans need myths and heroes; we need stories and tribes and costumes. We need to be able to feel something big and momentous that brings us closer to each other and gives us a shared sense of something bigger than ourselves.

Comic book movies might not be your thing, but they are a modern campfire.

They are a ritual of friendship that is much needed in what can be, for many people, an incredibly dark and unpredictable and anxiety-ridden time.

Marvel movies might not be for you; they might never be, and that’s fine. We can each have our own passions and our own tastes, but you have to go and find yours. If your sacred thing is hating everyone else’s sacred thing, there’s only one way that ends.

For everyone else, these heroes come to life.

These stories help.

These scenes heal.

These villains give us a way to channel and name our fears, and the endings give us hope.

You don’t need to join in, but you certainly have no right to sneer at us.

Being cold and mean and joyless and always above and apart from everyone else is not actually a sign of intelligence at all. You’re far more likely to find critical thinkers among the curious and the precise, the generous, and those willing to experience childlike delight. Calling everyone else dumb and complaining that culture is in decline and that you alone see and hold the truth actually makes you an incredibly lazy, boring, and self-indulgent critic.

A good critic asks, “Why does this matter? What need does this meet? What hunger does this fill, and what does the crowd feel?”

The intelligent understand joy; they don’t mock it.

They can see craft and commerce and emotion in more places than an arthouse flick.

They can hold more than one thing at a time.

Anyone can dislike a movie, but only a fool hates happiness. Millions of people enjoying a comic book movie is neither a crisis nor a plague, and it’s certainly not proof that the world has come to an end.

You can dislike it if you want. You can dislike the whole franchise. You can hate the entire genre. You can loathe the cape movie. But hating people for finding joy in it and building your own identity on contempt confuses bitterness with taste.

Am I harming you by counting down the days to the next Avengers movie?

Am I forcing you to participate by tweeting about it?

Am I stealing from you because I want to see it on opening night, or am I just happy?

Remember: if someone else’s happiness makes you angry, the problem is you.

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

If you spent any time on tech Twitter over the past few weeks, you’ll have seen the same growing panic.

People keep talking about how the indie hacker economy is collapsing.

Revenue is down for anyone building their own app, and the money is leaving the space.

And the reason why is simple: everyone points to AI. The more AI tools there are that can enable anyone to build anything, the less people need the tools built by indie hackers.

But I think the core problem here isn’t actually that the indie hackers are losing market share purely because of AI. I think it’s more because the indie hackers’ entire audience has always been other indie hackers.

Revenues are dropping because everyone in the indie hacker space is building for everyone else in the indie hacker space, who is already building for everyone else in the indie hacker space.

When builders keep selling to builders, they’re selling to the very people who are the most likely to build their own SaaS tools.

They’re selling SaaS to SaaS people, tools to tool makers. They’re selling products for people who would always rather build their own products in the first place.

That’s the core identifier of their whole scene.

Which means we now have an infinite supply of micro tools being marketed to a shrinking pool of genuine buyers, with more launch energy than there is market demand.

Read more

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

You could make something right now.

If you wanted to stop reading, grab a sheet of butcher’s paper and brainstorm ideas; you could probably come up with half a dozen ideas for apps, books, or products.

Ideas aren’t the hard part, after all  -  just ask Tom Haverford.

Or anyone with “Serial Founder” in their bio.

You could build a WordPress site and start harassing your friends to test the concept. You could start writing op-ed pieces on Substack and put “Founder” or “Author” in your Twitter bio within 48 hours. You could throw up a landing page, post the first chapter of a book, and start pushing it on Product Hunt.

Where things get tough is when you’re trying to make something that people genuinely give a shit about.

You don’t want your dream to die in the chamber, because nobody read it, watched it, used it, or listened to it.

Because the deafening silence surrounding your work can crush your soul.

You want people to care? Here’s how.

1.

Only Make What You Care About

If you want to make something that people actually care about, you have to care about it yourself. Because if you don’t, then try as you might, it’ll come out in the final product.

The reason for this?

Making something is hard. Making something you don’t care about is even harder.

The only way you’ll be able to consistently work when you don’t want to work, consistently try when you don’t want to try, is if you deeply and honestly care about your work.

This has never been more pronounced. AI seems to be making everything from software to the written word all but disposable; and the temptation that comes with it is to make as much work as possible, while caring as little as possible, and doing it at scale. I keep coming across creators who are obsessed with automating the work into a content farm; they want the glory of the written word, but they don’t want a single letter etched onto their souls.

Unfortunately - whether or not people can tell AI-written content from human-written content, I think most folks have an almost supernatural ability to sense whether a creator actually gives a damn. We know when someone doesn’t care. We know when someone’s phoning it in. We know when someone doesn’t give a shit.

The good news is this: being deeply invested in the things you make, say, and do is a moat that few will bother to build.

So, rule number one:

You want people to care?
You have to genuinely care yourself.

2.

Make Things For Real People

The best writing advice I have ever heard was to write specifically for someone I know.

It’s a genius idea.

Every time I go to create something, or build something, I think about who I know that would benefit from what I’m doing.

If you have something that you care enough about to make, you have to ask the next question  -  who are you making it for? What information do they need? What turn of phrase would stop them in their tracks? What is their single pain point that the product could solve, or their secret story that your novel would be able to touch and cultivate into a real emotional response?

Stop thinking about your audience as a vague concept, a collection of faceless people.

Believe that your audience is a real person with feelings, experiences and a story. It will change your perspective.

The mass appeal of social media makes this a good deal harder; the fact that every post has the (technical) potential to reach an audience of millions encourages us to believe that an audience of millions is within reach, that our target audience must be so broad as to give us the best possible fighting chance of capturing the multitudes.

This is a false idol.

Your audience is as small as the thing you care about, and as big as the things they care about. That’s it. The work of it all is finding out what those things are.

You want people to care?
You have to know what will make them care.

3.

Ask Yourself If You Fit The Project

You need to ask yourself whether you have the courage, the strength, the motivation, and the passion to make what you want to make.

Do you have what it takes to do this, specifically this?

And I mean really ask yourself.

When you first come up with an idea, you can get so caught up in it that you can’t see anything else. You can’t see the toil on your horizon.

It’s easy to mistake excitement for passion, motivation and ability.

When that feeling starts to die down, or you get used to it, you can realize that you don’t have the real raw power to be able to finish and follow through. The idea was grand enough to spark action, but the long tail of effort doesn’t and shouldn’t belong to you.

Fact: there is nothing wrong with recognizing that a project isn’t right for you.

Maybe there’s another project that is.

If it’s not this one, it’ll be another.

It’s not enough just to care about what you’re making  - it has to feel right.

You want people to care?
Only work on projects that feel right.

4.

Don’t Do Anything To Be Someone

Have you ever watched one of those reality TV singing competitions?

You’ve probably seen a hundred young people, eyes shining, clutching microphones and talking about their dreams.

They’ll explain that ever since they were kids, they wanted to be singers.

Note that: BE singers.

Be.

They hardly ever say they want to actually sing.

When it comes down to it, half the time it’s because actually singing isn’t the end goal. They want the trappings, lifestyle, and breaks of being a singer.

If the act of singing was really their end goal, they wouldn’t be on a reality TV show. They’d be out there every night singing anywhere they could, writing songs, starting bands, recording music.

The same is true for anything you could make.

Do you want to make X, or do you want to be the person who made X?

Because if you don’t care about the act of making something, and if you don’t want to get out there every day and try to make something, you might as well quit.

You want people to care?
Care about your work. Not your title.

5.

Work. Work Hard.

If you want to write a book that can break someone’s heart  -  work hard.

If you want to start a business that changes the world  -  work hard.

If you want to draw a comic book that expresses everything you are and dream about  -  work hard.

I think we’ve overindexed on being anti-hustle culture. And to be fair, hustle culture itself was mostly bullshit. But the way to push back against it isn’t to insist that hard work of any kind is something to be denigrated, mocked, and avoided at all costs.

The hands of a craftsman or an artisan are made rough by the friction of hours at their work. That’s not altogether a bad thing.

I am the first to say that the pursuit of burnout is a performative waste of a good life. But I have never achieved anything by embracing the admittedly attractive notion that hard work is simply too much to ask.

It’s not.

I wouldn’t call myself a particularly impressive or successful writer, founder, or anything else for that matter. But I make enough money from writing and working and building on the internet to support my family; and the only way that happens is by getting up every single day and putting in the hours, whether I want to or not.

You want people to care?
Work hard.

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

I’m not a true believer in much.

I am a fanatical believer in reading.

I do it early in my day, I do it late in my day, and I do it often.

I keep the Kobo app in my iPhone dock, a paperback in my messenger bag, and my eReader never out of arm’s reach. If I’m waiting in line for a coffee, jumping in an Uber, etc, I’ll be nose deep in a book.

Why?

It takes serious concentration, and I’m addicted to focus.

We keep searching for lifehacks, productivity tips, and bullshit, but the answer is right there. If you want to be better, grow more, understand your life, understand your purpose, learn something, or just find somewhere to stay a while when life gets overwhelming  -  pick up a damn book.

Why You Should Spend The Majority Of Your Time Reading

The Pareto Principle states that 20% of the effort yields 80% of the results.

It’s the 80/20 rule.

I believe that spending 20% of your time buried in a book, buried in something that will inspire you, excite you, and make you want to jump out of your seat is going to give you the fuel, the ideas, and the power to create 80% of your output.

It’s worked for me so far. Every decision I’ve made, every idea that’s shaped the course of my life, every drop of sweat that I have spent trying to be a better human being, can be traced back to the power of a good book.

In other words?

Damn right you should spend the majority of your time reading.

You should be reading books, newsletters, magazines, and blogs.

Literally anything of worth and value to you.

Anything and everything.

Reading books will improve your vocabulary by 80%.

Readers have a 20% reduction in the risk of dying before their time.

Readers are 2.5 times less likely to contract Alzheimers.

And readers have a better handle on the various weaknesses of dragons  -  something that may or may not be useful, depending on your career path.

Reading can shape your path

Even if you have a clear as crystal idea of what you want to do with your life, it’s almost impossible to know the correct path to follow.

There are so many things that can happen along the way that it can be tortuously difficult to figure out exactly where you should be going and how you should be getting there.

But you have access to the entire archive of human knowledge up until this point.

In the pages of every book in your library, every book on Kobo, every book on Gutenberg. You have access to every insight worth exploring, and the answer is going to be somewhere out there.

I would guarantee that there is not a single question or problem you could bring to me that can’t be solved with a book that someone has already written.

And it could have been written 1,000 years ago.

What you should spend the majority of your time reading

Books: This is the most obvious. Books are filled with words, ideas, and information that will improve your experience of life. Most of your time should be devoted to books, at whatever pace and in whatever category you’re comfortable with. They’re the purest form of the written word, created with love and care, crafted and honed to their best possible form.

Other publications: There are many other publications, newsletters, and news outlets that can be a good way to spend your reading time. But you’ve got to be careful about it. Reading the news obsessively can completely destroy any time you had devoted to reading, and throw it away in favor of doom scrolling, easily leading you down a Twitter rabbit hole instead of leading you down Lewis Carroll’s rabbit hole.

Sometimes you’re going to want to read something that isn’t going to make you smarter.

Sometimes, you’re going to want to read something that doesn’t challenge you.

Sometimes, you’re going to want to read pure trash.

The good news?

Even reading trash is better than watching it.

Even reading trash is still giving your reading muscles a quick workout. That’s never a waste of time. I’m not saying that you should spend the majority of your time reading Star Wars fan fiction. That would be ridiculous, and it might give you some odd ideas (yes, there’s a fanfic where the Almighty Sarlacc gets it on in quite a graphic scenario)

I’m saying that you should give yourself space to read what you want.

It’s the reading that matters.

It’s the journey, not the destination.

Fuck podcasts. I’ll take a book any day.

When people say that reading is not as exciting as watching a movie, or listening to a podcast, I want to f**king scream.

They’re wrong.

Books are full of excitement and adventure. Books are beautiful and detailed. Books are the home of suspense and mystery. Books contain the signals that we have to reach for amidst the noise.

There’s nothing boring about the act of reading.

It might not be scalable. There might be more efficient ways of consuming content. But it’s the only way to retain and explore information that can afford it the respect it deserves.

I’ve never seen the point of blasting through as much as possible, as fast as possible, with your podcast player set at 2x speed. It’s a breakneck approach to consumption that seems harmful to my mind. And it cheapens the content itself.

Just Read It.

Reading gets perceived (by various influencers and hustle-minded assholes) as a waste of time, a distraction from other tasks, or even a leisure activity that should be left for lazy weekends.

Even if it were just a way to pass an afternoon, it would still be the single best way to spend your life.

But it’s not only a hobby - the ability to read is a tool. In fact, if you were to spend the majority of your time reading, you’d be well on your way to achieving happiness, success, fulfillment, and so much more.

Reading is one of the most important skills you can learn, yet it is one of the most neglected.

Reading can help you understand other people, cultures, and perspectives. Reading can help you develop empathy for others.
Reading can help you learn how to write.
Reading can help you become a better thinker.
Reading can help you conquer your fears.
Reading can help you relax and reduce stress.
Reading can help you be more productive.
Reading can help you solve problems.
Reading can help you live a more fulfilling life.

Make some time to hit the library this weekend. Pick up a book from the store on the corner. Go through your shelves and build a stack of books you bought that you’ve been meaning to read. And carve out some time for it.

You won’t regret one single, solitary second.

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

The US AI companies are screaming about distillation.

(Again.)

To OpenAI and Anthropic, the idea of an open-source or Chinese AI company building their own AI by querying Claude, ChatGPT, etc is abhorrent - it’s a form of theft, taking that which doth not belong to them.

But there’s a deep hypocrisy at work here, and I don’t think it takes a highly developed moral compass to find it.

The US frontier companies built their own models on the entire corpus of human knowledge; they trained on books, images, music, videos, software and so on - entirely without the consent of the creators.

It’s the original sin of artificial intelligence. I won’t go so far as to say they stole these works - although in the case of torrented and pirated books, I think that case makes itself - but they certainly didn’t get permission from any of the folks whose work now constitutes Claude et al.

We weren’t allowed to opt out.

And in most cases, we certainly weren’t given compensation for our work.

In the vast scheme of things, this doesn’t actually keep me up at night. I’ve been writing on the internet long enough to know that my own work has been chewed up and digested by every model out there. I’ve understood that since the first models were able to do a passable job at generating a JA Westenberg-style blog post from first principles.

I remain largely unbothered by it.

Most of what I produce - including this blog - I consider to be open source anyway.

Reproduce it however you like; send me a link for my archives.

My problem is the moral inconsistency.

Defining Distillation

Distillation is when a smaller AI model learns from a bigger model. It’s almost copying homework; it extracts the patterns created by the frontier labs without having to copy the weights. The method enables AI models like DeepSeek to be built - and therefore, provided - at a fraction of the cost of US models.

According to the luminaries running Anthropic and OpenAI, this constitutes theft, inasmuch as it’s the unauthorized use of intellectual property.

But if Anthropic has extracted value from someone else’s work without permission, and DeepSeek has extracted value from Anthropic’s work without permission, I fail to see which sinner has acted more egregiously.

Both have used the output without direct permission; both claim:” Transformative use” as a defense. The logic is identical. If, as a writer, Anthropic has trained on my work without my consent, I don’t see that I should be at all invested in protecting Anthropic’s rights if and when Moonshot (the makers of Kimi) train on Anthropic’s work.

It seems a fairly clear-cut case of what goes around comes around.

On Power Asymmetries.

Anthropic, of course, has teams of lawyers, lobbyists, and flaks. They have an army of folks whom they can call on to protect their IP. The individual artists, creators, etc whose work wound up in their training data have no such advantages.

They have every right to attempt to use that army to fight for their commercial moat, but they’re playing a very different game than the rest of us. They’re not the victims here, and pretending to be so when their own logic is turned on them seems a bit rich.

A bully who goes crying when someone else punches back is hardly likely to garner sympathy from anyone but the bully’s own overindulgent mother.

If training data is fair use, it must logically follow that distillation is fair use; and if distillation is theft, it must follow that training is also theft. You can’t have your cake and eat it too. You have to pick one.

And the truth is, they already picked theft, by their own definition of the word.

Nobody in AI has clean hands; everyone is tainted to some degree by the original sin of training data. The entire stack is built on borrowed ground, and arguing about distillation won’t change that fact. I don’t think you need to abandon AI entirely because of it, but you do have to take the indignation of the injured AI labs with more than a grain of salt.

Anthropic and OpenAI forfeited the moral argument at the inception of their commercial models. They may be able to make a compelling legal case to the US Government, but they have no ethical case they can make that won’t show them up to be sore losers who can’t handle their own medicine.

Distillation is a mirror.

Just because the US labs hate what they see in it doesn’t mean the rest of us should weep tears of sympathy.

I cover:

• The actual comments Naval made about his schedule and his wife booking his time.

• Why the internet views this as wealthy philosophy instead of real wisdom.

• The “if you need me you’ll find me” problem and how it establishes a strict hierarchy.

• How survivorship bias plays into billionaire lifestyle advice.

• Why modern audiences are totally allergic to guru content right now.

If you enjoyed this video, definitely subscribe and leave a comment below.

Do you think Naval’s approach is pure freedom or a status flex?

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

I’ll be the first to say I was a fan of Tim Ferriss.

Actually, scratch that. I am a fan.

I have all of his books, from The 4-Hour Workweek to Tools of Titans.

So what follows isn’t intended as a hit piece.

But I have a growing sense that the core argument of The 4-Hour Workweek itself - the thesis that we should be creating loops of income-generating work that remove the human from the loop - is both obsolete and dangerous.

The original book was the product of a specific moment: the explosion of online products and services, in a pre-AI, pre-remote-work-mass-adoption era, when time and geographical arbitrage still mattered.

But it’s not 2003 anymore.

It’s 2026, and passivity - whether it’s to do with your income or literally any part of your life - is dead.

The original arbitrage (and why it worked)

What Tim Ferriss actually taught:

You should outsource as much as possible to cheaper labor, automate everything else, and live like a king in Buenos Aires, Thailand, Bali, etc, profiting off the USD value imbalance and letting your business run itself as much as possible.

The advice was to get out of your expensive backyard, uproot, move somewhere cheap, and build a largely autonomous business that printed money while you slept. It was the OG passive income Bible.

The PI businesses of the age were largely informational: selling cheap physical products en masse under your own brand or selling PDFs of your domain knowledge.

They made money because information asymmetry still existed. Simply put: you could know things that other people couldn’t, and you could monetize that knowledge because it was actually in demand.

It was the “Muse” business model: create a low-touch product, automate fulfillment, and reap the rewards. You can still find various grifters pushing this model in 2026.

It no longer works, but it did work for Ferris and the cohorts who came directly after him.

The AI collapse

AI automated the tasks better than any of us ever could; but more than that, it flattened out the arbitrage itself. Every single tactic of the Passive Income gurus is now available to anyone with the cheapest possible AI // LLM subscription. VA work? AI does it for next to nothing, and better than a VA used to. Niche info products? AI can generate 100 in a single run. Dropshipping? Automated. Content farms? Dead. SEO arbitrage? Buried.

The moat, if there was one, was asymmetric effort. But AI removes the asymmetry. If it can be done passively, it can be done by AI, for everyone, digital nomads not required.

The speed of change is critical here too. Passively sitting back to let your business run itself = sitting out one of the fastest-moving periods of tech change in our history - and you’re missing out on every single opportunity that comes with it. The passive income model relied on taking advantage of tech to apply your arbitrage, but the tech is changing fast enough now to make any form of passivity a liability.

If your goal is to sit on a beach and glance at a laptop a few hours a week, you’re functionally behind.

But was any of it true?

Of course, if you pull back the curtain, passive income was never actually passive./ It took massive upfront effort, constant maintenance, algorithmic chasing,n customer service, and reinvention. Tim Ferriss himself worked constantly, putting in vast amounts of effort above and beyond the vaunted four hours, appearing on podcasts, writing books, doing consulting and speaking tours, angel investing, etc. There was nothing passive about the godfather of passive income at all.

And there was nothing passive about the work adopted by his disciples either.

The passive part was just outsourcing the visible work, while you did the invisible work of managing the machinery.

But the machine now runs itself, which means it runs for your competitors too. The only thing left is a commodification race to the bottom.

What replaces passive income? (active leverage)

AI creates infinite supply, meaning the only scarce resource left is human judgment, curation, and trust. If you define active leverage as using AI to amplify your output, not eliminate your involvement, there are massive opportunities that dwarf anything the passive income blogger could have dreamed of.

The goal is no longer 4 hours; it’s 40 hours of high-leverage work that produces 400 hours of impact.

If you’re actually present and accounted for, the power of a frontier model is incredible, and it will pay out asymmetrical rewards; but if you’re chasing passivity and attempting to outsource your entire existence to an LLM, you’ll be arbitraged to fuck by everyone else who still shows up with their brain attached.

And you’ll deserve it.

If you’re still chasing passive income, you’re building an obsolete 2006 business in 2026, and that only ends one way. Working 4 hours a week is more of a red flag than something to celebrate; it means you’ve removed yourself from the loop, abdicating responsibility, and automating yourself into irrelevance.

The irrelevant are replaceable.

And the replaceable are expendable.

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

I keep seeing the same people crashing out over the same thing.

I keep being told that we’re heading for an apocalypse, and that I have either three, or six, or 12 months to escape the permanent underclass, after which the social order will have been entirely rewritten, and the haves (post-AI millionaires) will eternally rule over the have-nots (the rest of us chumps)

I’d expect to hear this from the AI doomers; it’s their bread and butter to spread the message of bleak determinism that says everything is over for the human species.

But they’re not the core culprits.

The culprits are the AI maximalists - the tech optimists and indie makers who are thoroughly AI-pilled; they're the folks who are the loudest about the “permanent underclass.”

I think the reason why is simple: they’re overexposed to AI; they’re on the cutting edge, consuming the latest reports, whitepapers, blog posts, tools, etc, and everyone in their bubble is talking about AI constantly. They can’t catch their breath. They’re operating from a very human place of anxious insecurity, and it’s 10xed by their exposure.

But I also think they’re wrong.

The historical pattern of these exact predictions failing repeats over and over again.

And it’s both incredibly hubristic and ridiculously short-sighted to think our current viral predictions won’t fail in the same way.

Read more

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

You’ve heard the line (slogan?) a thousand times.

“If you’re not paying for the product, you are the product.”

It’s a clever-sounding thing people post on the very platforms they criticize and spew at the parties I am no longer invited to because I have a terrible habit of rolling my eyes, and because I have no poker face at all.

But I think the idea is wrong.

Or perhaps - it’s not wrong enough.

It lets you believe the transaction makes some kind of sense: the platforms take your data and/or your soul, but you get free cat videos. A fair trade, maybe slightly sleazy, but completely understandable.

A product.

Fine.

Products are things. Things get used, sure, but they also get shelved, preserved, owned.

All well and good.

But you are not actually the product.

You are the Mine.

Read more

Hey!

You’re on this list because you give a damn about the written word.

So I’ll skip the warm-up and tell you the news.

SELF has relaunched.

SELF is my studio for turning technical founders and builders into public thinkers. Essays, keynote narratives, messaging, founder voice. One senior operator - me, JA Westenberg - doing the work directly.

No handoffs, no account managers, no coordination tax, etc.

Here’s why it exists:

The best builders // makers often have sharper ideas than anyone in their market, but they rarely get credit for them.

Their thinking stays trapped in Slack threads, all-hands decks, and half-finished drafts that never ship.

SELF takes what you actually believe and turns it into a body of work people follow - essays that get shared, talks that get quoted, and a point of view your market checks before deciding what it thinks.

How it works:

1. Subscribe. Pick a plan and bring your hardest narrative problems.

2. Request. A full thought leadership program, or a single essay.

3. Receive. Work back in 48–72 hours, depending on your plan.

Three plans, flat monthly fee, in USD. Pause anytime - billing pauses with it.

Book a call

Apply to see if you’re a fit

Try it for a week, and if it’s not for you, get 75% back.

The partner list is strictly capped. I’m a solo, founder-led studio, and the quality of the thinking 1:1 is a product I’m deeply passionate about.

If your best ideas are still stuck in drafts, this is the fix.

JA Westenberg

P.S. If you want a sample of how I think before you commit, the new essays are live on the site - start here! “Humans Don’t Want Infinite Content. We Want Common Ground.”

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

In summer 1999, a kid could whisper “I see dead people,” and every person in the room knew exactly what he meant. That is what a movie actually is. It’s not content; it’s never content. It’s actually closer to a coordination technology - a machine for getting millions of nervous systems to fire in sync.

In this video, I take on the “everyone will just prompt their own movies” prediction. The people making it understand the models, the costs, and the timelines. What they miss is a category error: they think culture is a product to be consumed, when it is actually a fire to be gathered around.

I call it the campfire law: the value of culture scales with the number of people who share it, not with how well it fits you.

What I Cover

• Why “I see dead people” was a skeleton key that unlocked every classroom, dinner table, and bus ride in 1999, and why your perfect personalized AI movie in 2035 unlocks nothing

• The campfire law: content is fuel, culture is a fire, and a fire exists to be gathered around

• How TikTok, the most personalized media machine ever built, immediately got repurposed into a folk monoculture of shared sounds, jokes, and dances

• The dream test: your subconscious already produces perfectly personalized entertainment every night, and “let me tell you about my dream” is the most boring sentence in the English language

• Why references are the compression algorithm of human connection, and shared context is the reserve currency of every friendship and group chat

• The software version of the same mistake: your prompted personal app has no tribe, no tutorials, no forum, and no fan club

• Why restaurants, concerts, and sports should all be “dead” by the optimization logic, and why they are not

• What history says happens when the cost of making culture collapses: cheap cameras gave us YouTube, cheap distribution gave us podcasts, cheap publishing gave us newsletters. More fires, not more isolation

• My prediction: everyone will be able to prompt their own movies, and almost nobody will want to most of the time

Key Quotes

• “A movie is not content. A movie is a coordination technology.”

• “The film is the vehicle, the synchronization is the product, and you can’t synchronize with only yourself.”

• “Content is fuel, culture is a fire, and a fire exists to be gathered around.”

• “A reference is only worth something if the other person holds the file.”

• “Being the sole user of a product is solitary confinement.”

• “Humans don’t want infinite content. Humans want common ground.”

• “The maker will change, but the gathering never will.”

The One Question That Survives Every Media Revolution

“Okay, what’s everyone watching?”

That question is not going anywhere. The future of media is not a billion people watching a billion private movies alone in the dark. It is the same thing it has always been: all of us around the same fire, arguing about the ending.

If you liked this one, subscribe and drop a comment: what’s the one movie line that works as a skeleton key for you?

Mine: “Greed, for lack of a better word, is good…”

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

Most writers choose a niche by looking outward.

They study what’s popular.

Possibly, compare audience sizes.

They search for gaps within established categories: productivity, personal finance, business, creativity, the eternally nebulous “self-improvement.”

And then they squeeze themselves into whichever box appears most promising // profitable.

It’s the current best practice x best advice you’ll hear from every authorial charlatan flogging a course.

But 9 times out of 10, it’s the reason your work becomes completely forgettable.

When you start with the market, you inherit the market’s language, assumptions, and boundaries. You inherit someone else’s idea of what a Good Writer should write about, and you end up writing competent variations of ideas readers have already encountered from people with more experience, more authority, and a larger following.

The resulting output reads as lifeless dreck. It may be useful, and it may even perform well occasionally. But it gives off the unmistakable aura of work produced to meet a “niche.”

I tell first-time writers to use first-principles thinking instead.

Don’t ask, “Which niche should I choose?”

Dismantle the concept of a niche and ask what makes one worth occupying in the first place?

Then rebuild yours from the raw materials of your own life…

A Niche Is Not a Topic

“Productivity” is not actually a niche.

Neither is marketing, psychology, technology, leadership, fitness, or personal finance. These are markets - vast territories containing thousands of writers saying roughly the same things.

A useful niche isn’t simply what you write about.

It is the distinct perspective from which you write about it, for a particular person facing a particular problem.

Compare the difference:

I write about productivity.

Vs:

I help ambitious people who hate rigid systems build a calmer way of working.

The first describes a category, but the second has tension, perspective, and a reader.

Readers don’t follow writers for access to a topic.

They can find information anywhere.

YouTube, TikTok, etc.

They follow writers who help them see familiar problems differently.

Your real “niche” is not the subject you cover.

It’s the intellectual territory you can explain better than almost anyone else because of the unusual combination of what fascinates you, what experience has taught you, and whom you understand.

Why Conventional Niche Advice Produces Conventional Writing

Most niche advice follows the same sequence:

1. Find a growing market.

2. Identify a popular problem.

3. Study successful creators.

4. Publish your version of what already works.

All of which can help you manufacture content, but it won’t help you develop a body of work.

That is because it treats writing as a positioning exercise before treating it as an act of thought.

When you reverse-engineer a niche from market demand, your prose comes off like an assigned College Essay. You can reproduce the format, use the right hooks, and publish on schedule, but readers can sense when the writer arrived at the subject through opportunity and instruction over conviction.

More dangerous though: starting with an established category means accepting someone else’s map.

You accept their definitions of the important questions.

You accept their vocabulary.

You accept on their terms.

First-principles thinking asks you to temporarily discard that map.

Replace “Where is there room for me?” with three more useful questions:

• What’s the one thing I can’t stop thinking about?

• What’s the one thing I understand because I have lived it?

• Who actually needs that understanding?

The Three Raw Materials of a Durable Niche

A niche capable of supporting years of meaningful work needs three ingredients:

Obsession × earned insight × unmet need

• Obsession gives you energy.

• Earned insight gives you authority.

• Unmet need gives your writing relevance.

This is not a checklist where two out of three is good enough.

If one factor approaches zero, so does the value of the whole.

1. Inventory Your Obsessions, Not Your Interests

Interests are pleasant.

Obsessions are persistent.

An interest is something you enjoy reading about. An obsession follows you into the shower, interrupts unrelated conversations, and makes you open seventeen browser tabs past midnight like the crazed, fucked up little Wikipedia gremlin you are.

(You know precisely what I’m talking about.)

You can build ten articles around an interest, but you can build a decade of work, an entire lifetime of work around an obsession.

1. See: Tolkien’s obsession with myths, industrialisation and what drives men to make war…

2. See: and his obsession with finding and teaching an alternative to trad work

To identify yours, ignore the subjects you think a serious writer is supposed to care about.

Ask instead:

• What do I investigate without needing a reason?

• Which problems do I keep returning to after everyone else has moved on?

• What do I read about when nobody is watching?

• What do I explain with more enthusiasm than the situation requires?

• Which commonly accepted ideas irritate me because they feel incomplete or wrong?

Pay special attention to the obsessions that seem too narrow, impractical, or embarrassing.

Write down ten obsessions.

Then cross out anything you’ve gone ahead and included because it sounds intelligent, respectable, or commercially attractive. And don’t kid yourself. You’re the only one getting screwed by that.

2. Identify the Knowledge You Had to Earn

Obsession creates curiosity, but curiosity alone won’t create authority.

Your second raw material is knowledge acquired through contact with reality: decisions made, consequences absorbed, patterns observed, decisions fucked up and beliefs revised.

This is not the same as credentials.

Credentials may indicate that you studied something. Earned insight reveals that the subject changed you.

Ask yourself:

• Where have I been tested repeatedly?

• What have I learned through failure, responsibility, or prolonged exposure?

• What can I see now that my younger self could not?

• Which accepted explanations conflict with what I have witnessed?

• What do beginners consistently misunderstand about work I know well?

• What can I explain that cannot be learned from a summary or textbook?

Note: you’re not looking only // exclusively for expertise.

You’re looking for earned contradictions:

“People usually say X. My experience taught me Y.”

3. Find the Reader Experiencing the Sharpest Need

Writers ruin a promising niche by trying to make their audience too big, too early.

They write for “creatives,” “professionals,” or “people who want to improve their lives.”

These groups sound commercially attractive because they contain millions upon millions of people, but they’re too broad to capture effectively.

If you can’t imagine the moment in which someone needs your writing, you’ll struggle and fail to produce anything precise enough to get attention and garner a single reader.

Instead of asking how large the audience is, ask:

• Who is repeatedly making an expensive mistake I know how to prevent?

• Who would feel relieved - not merely informed - after reading what I know?

• What problem can I describe in the exact language its sufferers use privately?

A strong niche is usually built around a specific tension.

Never “career advice for creatives,” always:

Career strategy for experienced creatives who want stability without turning their work into soulless content.

Never “leadership for founders,” always:

How first-time technical founders can lead former peers without becoming controlling or evasive.

Never “personal finance for freelancers,” always:

Financial systems for freelancers whose income is high, irregular, and psychologically difficult to trust.

When the right reader encounters precise language for a problem they have struggled to articulate, they don’t waste their time thinking, “This audience seems small.”

They think, “This was written for me.”

Find the Overlap

Now place your three lists beside one another:

• What are you obsessed with

• What has experience taught you

• What does a specific reader urgently need

Obsession without earned insight produces enthusiasm without depth.

Earned insight without obsession produces technically correct writing you will eventually resent.

Obsession and insight without an unmet need produce a private journal.

Need without either of the other two produces generic content engineered for attention.

Broad niches sound familiar because they’re assembled from established categories. Original niches sound unusual // freakish because they’re assembled from a life no one else has lived.

Imagine, for example, someone who has:

• an obsession with decision-making under uncertainty;

• ten years of experience managing live events, where plans regularly collapse;

• a deep understanding of anxious high performers who freeze when conditions become unpredictable.

They might want to write about “productivity,” but the right niche won't actually be “productivity.”

It might be:

Practical decision-making for high performers who need to act before they feel certain.

Narrower x easier to own.

Turn the Intersection Into a Point of View

Even a precise niche is not enough; you need a perspective - a POV.

Your point of view is the claim beneath your work: the idea you’ll explore, test, complicate, and defend across many pieces.

A useful way to articulate it is:

Most people believe ________.
My experience suggests ________.
This makes a difference, because ________.

For example:

Most people believe consistency comes from discipline.
My experience suggests it comes from reducing emotional negotiation.
This makes a difference, because people keep designing ambitious routines they must persuade themselves to follow every day.

Now the writer has more than a topic; they have an engine for generating ideas.

They can write about habits, environments, identity, motivation, software, planning, fatigue, and attention without becoming scattered, because every subject is examined through the same underlying lens.

A niche tells readers where you operate.

A point of view explains why your work could not have come from anyone else.

Test Your Niche With One Definitive Piece

Don’t breathlessly announce your new niche immediately.

Don’t redesign your website, rewrite every biography, or create a twelve-month content calendar.

Write one definitive piece.

Choose a problem sitting at the exact overlap of your obsession, your earned insight, and your reader’s unmet need. Then write the version that only you could write.

Use the details others omit.

Include exactly what experience forced you to unlearn.

Treat the reader as an intelligent adult capable of handling complexity.

Then publish it and study the response.

Look for stronger signals:

• Did the right people recognize themselves?

• Did readers reply with specific stories?

• Did anyone say, “I thought I was the only one”?

• Did the piece generate better questions?

• Did writing it create ten more ideas?

• Do you feel more curious about the subject now than before you began?

A promising niche creates energy on both sides.

Readers feel seen, and the writer discovers more territory to explore.

If the piece falls flat, adjust the coordinates.

Don’t abandon the entire framework after one attempt. Refine it.

A niche is not selected once.

It becomes clearer through repeated contact with readers and reality.

The Goal Is Not to Eliminate Competition

You don’t need to find a subject nobody has ever discussed.

That’s nearly impossible, and usually undesirable.

You need to develop a combination that nobody else can reproduce exactly:

• your questions;

• your experiences;

• your contradictions;

• your reader;

• your language;

• your way of noticing.

This is why copying another writer’s niche never quite works.

You can imitate their subject and format, but you can’t recreate the life that made their perspective credible.

The safest writing niche is never the biggest category or the emptiest market.

It’s the territory where your curiosity, experience, and usefulness reinforce one another so strongly that continuing to explore it feels almost inevitable.

Never

Which niche should I choose?

Ask:

What can I see because of where I have been - and who needs help seeing it too?

Answer that question precisely enough, and you’ll find the beginning of a body of work.

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

AI companies have built their entire product empire on the misconception that infinite choice is a Good Thing ™️

They’ve convinced themselves that abundance is a gift - that we somehow want *more* options, *more* drafts, *more* noise. Ask for a logo, get fifty. Ask for an email, get ten. Ask for a strategy, and drown in a tidal wave of vomited and re-vomited decks, memos, and over-engineered frameworks.

But nobody actually wants this.

Nobody wants infinite choice and infinite options.

Consumers have proven they hate it for 30 years, as shown by the products they love, return to, and buy.

Every successful product, from the iPhone to the Spotify algorithm, relies on one simple premise: we steal your decisions, we tell you what to do, and you love it.

We Literally Pay Not to Have Choice

Netflix launched on the selling point of an infinite catalog: every movie at your fingertips forever.

And then they discovered an infinite catalog destroys engagement, and the company has spent north of $20 billion in original content trying to fix the disaster.

Infinite catalogs drive paralysis and churn.

Subscribers stared at the interface, couldn’t pick anything, and felt depressed about their evening.

So Netflix built algorithms to strangle the options.

The company created categories, buckets, personalized queues, and autoplay. It invested billions in original content to produce a single answer to “what should I watch tonight?”

Netflix pivoted its whole product into a machine that killed the choice it promised to deliver.

And engagement skyrocketed.

Costco sells around 4,000 SKUs.

The average supermarket carries 30,000.

Costco’s model is commercially authoritarian: we decided for you.

You get one mayonnaise, one ketchup, and one olive oil.

And customers experience this as pure relief.

Costco posts customer loyalty scores that dwarf most retailers’ ambitions.

The constraint is an actual value proposition, and buyers worship it.

When Steve Jobs returned to Apple, he gutted the product line to four devices and murdered the options that had infested Apple throughout the 90s.

Every few years since, Apple removes something (a port, a headphone jack, a feature users swear is structural), and users adapt and go back to buying more Apple products at higher prices.

Analysts might call it arrogance, but over and over again, customers prove they would rather pay a premium to be bossed around than face an open shelf.

What Restaurants Know That AI Doesn’t

I’m the co-founder of a bar here in Sydney, and we’re incredibly proud to have a bare-bones menu.

We have a handful of dishes we love, that our regulars love - late-night toasties and so on - and a limited number of bespoke cocktails.

People find something they like, and they trust that we’ll make it well, because we’re not distracted by trying to stay on top of a 200-item Bible of canapés and mixed drinks.

A 200-item menu dumps the kitchen’s failure onto your cognitive load instead of offering you freedom.

Every item past a certain threshold means the staff refuses to offer an opinion or say, “This is what we’re good at, and this is what you should eat.”

In omakase, the Japanese tradition, the chef decides what you eat based on what’s good that day.

Omakase commands prices that would make a steakhouse blush because the chef strips away every choice.

People pay more, sometimes dramatically so, to have fewer options.

Silicon Valley executives apparently cannot comprehend this.

But deciding is work that depletes the same cognitive resources as manual labor, and people with finite resources will pay a fortune to get that work done for them.

Early dating apps competed on volume: more matches, more profiles, more swipes.

Users discovered more matches correlated with worse outcomes.

More matches meant perpetual browsing and permanent background anxiety that the right person was in the next batch.

It created a learned helplessness about commitment that made entire cohorts functionally unable to go on a second date…

Re: Executive Cowardice

Senior executives have plenty of information.

They know what their customers want.

Deep down, they know.

Their bottleneck is cowardice.

The consultancies and chiefs of staff who command the highest fees walk in and say: you should do this.

They provide the guts the executive lacks.

McKinsey etc charge premium fees for cover, not analysis.

Current AI can’t provide this.

It does research well, but it can’t draw definitive conclusions and stand by them in an argument.

It generates options compulsively, hedges reflexively, and keeps spewing multiple perspectives with the evenhandedness of someone terrified of being wrong.

Engineers optimized it for the appearance of comprehensiveness rather than the delivery of guidance.

It’s the world’s most capable intern: brilliant at gathering, completely gutless at deciding.

The Paradox Is About to Get Worse

Barry Schwartz documented this dynamic in 2004 in The Paradox of Choice.

More options reliably produce worse outcomes across purchase decisions, medical choices, romantic partnerships, and career moves.

This is one of the most robust findings in behavioral economics.

But tech executives spent twenty years building products that deliberately violated it, in the name of engagement metrics that turned out to measure anxiety as much as satisfaction.

AI will violate it harder, at higher intensity, across every product category.

Every AI writing tool gives you ten versions.

Every image generator gives you a grid of four.

Every AI search interface now returns a summary with six angles, three caveats, and a dozen links for further reading.

The volume of options hitting knowledge workers has increased by an order of magnitude over the past two years and shows no sign of stabilizing.

Pre-AI information overload looks quaint from here.

Decision fatigue has moved from psychology journals into mainstream conversation.

Consumers buy capsule wardrobes, meal prep systems, and morning routines with zero variables.

People pay coaches and consultants specifically to reduce the number of choices available to them.

The demand signal is deafening.

But the industry is building in the exact opposite direction.

What the Winning Products Will Have to Do

Generation is becoming a commodity; every foundation model can produce competent output on demand.

The moat belongs to products that use generation internally and deliver conclusions externally, doing the synthesis behind the curtain and handing you an answer, not a menu.

The product will say “here’s your onboarding email,” instead of “here are six approaches; which direction feels right?”

The product will say “here’s the angle; here’s why it wins,” instead of “here are eight potential angles for this pitch deck.”

The AI does the work of having a point of view.

The user gets the output of that work.

This sounds simple, but it’s the hardest thing to build, because builders must hold the product accountable when it is visibly wrong.

That’s why most AI products won’t do it.

Taking a position means being accountable for the position.

Generating options is safe; every direction is defensible because the generator didn’t actually pick one.

The option-generation interface is the AI industry’s version of the 200-item menu: it looks like capability, but it’s the product and its creators hedging their bets.

The highest-value human services have always understood this.

The doctor who says “here’s what you need to do if you want to live to see your kid graduate” is worth a whole lot more than a doctor who says “here are your options, let me know what you decide.”

The editor who cuts the bad paragraph is worth more than the editor who leaves a comment musing about it.

The premium has always gone to people willing to have a view and defend it.

AI is no different.

But you can also take a step away from learning if you aren’t careful.

When you finish a book, podcast, or thread from someone impressive, you feel a sense of fullness. You assume if you just do what they did, you’ll get to where they got. That is almost never true.

In this video, I break down why copying successful people usually fails, how teachers sell you dependency disguised as pedagogy, and how you can extract the real principles that actually transfer to your life.

Key Takeaways:

• The visible parts of success - the habits, the sayings, the aesthetic choices - are just the residue left by a much messier process.

• Don’t take prescriptions unchanged. “Write every morning” is a prescription. The principle is “protect your cognitive best hours.” Extract the principle and re-implement it.

• Gurus sell complete frameworks to create dependency. They optimize for your devotion, not your learning.

• You should scale your deference to the demonstrated domain. A 20-year VC veteran has a great model for company-building. That does not elevate their views on nutrition.

• You do the actual learning by interrogating sources. Everything else is just you admiring them.

I discuss my belief that modern journaling has become a public performance, and share practical steps to adopt the audience-of-zero mindset so you can use writing to figure yourself out rather than to present a polished version of your life…

Key Topics…

• Why Marcus Aurelius wrote with an audience of zero

• The trap of the modern public diary

• How performing for a hypothetical reader ruins your honesty

• Why you should write ugly and use a cheap notebook

• Stopping the factual narration of your day

• Using repetition as a mental gym

• Giving yourself direct commands in the imperative mood

If you found this video helpful, please hit the like button and subscribe to the channel. Let me know in the comments below if you plan to try the zero-audience method in your own life!

Once upon a commit, someone looked at GitHub’s little green squares and thought: what if writers had that?

That someone was me!

And the app is called Kerouac.

For the last year, I’ve been building a writing studio that takes publishing seriously.

If you write online, you already know the pain: your work is everywhere.

A Substack from your current era, a Ghost blog from the one before that, a Medium publication, a personal site you keep meaning to revive, maybe even a YouTube script or two. Your body of work is scattered across the internet, and your motivation is just as scattered. You can’t see the pattern. You can’t feel the streak. You definitely can’t tell whether this year was better than last year.

Kerouac is my answer to that.

What Kerouac actually is

At its heart, Kerouac is a 365-day heatmap of your publishing life.

Connect Substack, Ghost, Medium, Micro.blog, YouTube, any RSS feed, and Kerouac pulls in everything you’ve ever published and shows where you shipped, where you went quiet, how long your streaks are, and what your actual rhythm looks like.

I wanted the dashboard to be the dashboard: a single view that tells you, at a glance, whether you’re keeping the promise you made to yourself.

Behind the heatmap you get:

• Daily and weekly streaks

• At-risk countdowns when a streak is about to break

• A Friday email that gently panics you if a 2+ week streak is in danger

• Insights that read like a story, not a report: words written, weekday habits, platform mix, quiet stretches, and year-over-year pace

For the first time, I can see my own writing as a practice, not just a list of posts.

But it’s not only a rearview mirror

Tracking is nice. Shipping is better.

So Kerouac is also a drafting studio. There’s an idea inbox for the half-thoughts that usually disappear before you can use them. A kanban board for running your blog like a pipeline: Idea → To Do → Drafting → Editing → Reviewing → Scheduled → Published. And a Markdown editor with a built-in research shelf for links, notes, images, and quote snippets you can drag straight into the draft.

I’ve been using the board myself for months now, and it’s changed how I think about writing. Instead of “I should write something,” it becomes “what’s in the pipeline, and what stage needs attention?”

The editor also has syntax highlighting that paints your prose by parts of speech - nouns, verbs, adjectives, adverbs, passive voice - so the weak spots surface without feeling like a grammar lecture.

Importantly, the editor has zero AI features. I’m not against AI - but I think a writer’s studio needs to be a space for a writer to write.

Share away

Writing in public is a weird kind of loneliness. You publish, you hope someone reads it, and then the post drifts downstream into the internet.

So I added public profiles. Claim a username and your graph goes live at: kerouac.app/u/yourname

You get a clean profile with your recent posts across every platform, share cards, Open Graph images, and an embeddable SVG badge you can drop in your README, your newsletter footer, or the bottom of your blog.

You can follow other writers, peek at their heatmaps, and scroll a chronological feed of what they actually published. It’s proof of work, in public, without becoming another engagement-mining social network.

Simple pricing

I didn’t want feature tiers that make you do math.

Kerouac is free for 30 days, no credit card required. After that, it’s $8/month or $60/year (which saves two months). Every plan gets the full studio. No paywalled features, no surprise charges, no “upgrade to unlock the board” nonsense.

Just pick how you want to pay.

If you want to get started today, you can use this code for 50% off your first year:

FIRSTYEAR50

FIRSTYEAR50

SIGN UP

Why this matters to me

I built Kerouac because I needed it. I’ve been writing online for years, and I was tired of feeling like my work was slipping through my fingers. I wanted a place where every post I’ve ever shipped lives next to every idea I haven’t written yet. I wanted to see the consistency, or the lack of it.

In one sentence: Kerouac is GitHub contribution graphs for writers - plus a drafting studio, a tiny social network of heatmaps, a Linktree replacement, and more coming.

If that sounds like something you need, come take it for a spin.

Grab your username. Connect your platforms. Take the 30-day free trial.

SIGN UP

Covering:

• The Gilgamesh Complex: Why the oldest story ever written proves that the fear of death is hardwired into human nature.

• The Core of Longevity Maxxing: We break down the extreme world of modern biohacking. What are people actually doing to stop the clock?

• The Modern “Snake”: Gilgamesh lost his plant of rejuvenation to a snake. What are the biological realities, entropy, and genetic limits that will inevitably steal our modern “plant” of immortality?

Are we finally on the verge of beating the clock, or are today’s longevity maxxers just modern-day Gilgameshes destined to look at the walls of their own mortality and accept defeat?

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Studio Self, a thought leadership agency for founders x VCs.

I am the proud owner of a lightly used bread machine.

It’s an appliance about the size of a microwave, and it sits on my kitchen counter.

It cost about a hundred bucks.

The ingredients for a basic loaf are flour, water, yeast, and salt. A bag of flour costs two or three dollars and yields maybe ten loaves. A jar of yeast lasts for months. Salt is cheap enough to be a negligible cost.

The machine does almost everything: it kneads, it proofs, it bakes. I dump the ingredients in, press a button, and three hours later I have bread.

Well, I have used this machine perhaps twice in three years.

Instead, every week I go to the grocery store and buy a loaf of pre-sliced, factory-produced bread in a plastic bag.

This is the bread paradox.

And it explains why SaaS companies are very, very far from being doomed.

Five thousand years of bread, and we still buy it pre-made

In one form or another, in almost every culture, humans have been baking bread for at least five thousand years.

The ancient Egyptians were running commercial bakeries along the Nile by around 3000 BCE, using emmer wheat and sourdough fermentation techniques that wouldn’t be out of place in a modern artisanal bakery in Brooklyn. The Romans “industrialized “ the process, and by the time Pliny the Elder wrote his Natural History in the first century CE, Rome had a professional bakers’ guild, animal-powered dough-kneading machines, and a distribution network that supplied bread to hundreds of thousands of urban residents who never baked a loaf themselves.

They bought.

And they bought for the same reasons as I did, thousands of years later: because it was easier, because it was consistent, and because the alternative cost time and attention they’d rather have spent elsewhere.

The medieval European guild system kept baking professional for centuries. In London, the Worshipful Company of Bakers received its first royal charter in the 12th century, and sheriffs dragged bakers who sold underweight bread through the streets on a sled as punishment. The guilds enforced standards, maintained training through apprenticeships, and ensured that townspeople bought their bread from specialists rather than making it themselves. The vision of a medieval peasant household where everyone bakes their own daily loaf is a romantic invention. People baked at home when they had no other option. When bakers were available and affordable, they bought.

In 1928, Otto Rohwedder perfected the commercial bread-slicing machine in Chillicothe, Missouri, and within a few years, American bakeries were shipping pre-sliced loaves in mass-produced packaging across the country. In 1961, researchers at the British Baking Industries Research Association in Chorleywood developed a process that reduced bread production time from hours to minutes by using mechanical dough development and chemical additives. By the late 20th century, American bakeries had achieved a level of efficiency and scale that would have been unimaginable to a Roman baker or a medieval guildsman. Today, the United States consumes about 21 million tons of bread and bakery products annually. Divided across the population and the days of the year, Americans buy about 10 million loaves of pre-baked bread each day.

That’s ten million loaves a day, in a country where flour costs pennies per loaf, where bread machines cost under a hundred dollars, where bakers and homemakers have known the recipe for five millennia, and where a machine can do the whole job for you.

The make-or-buy gap

In George Orwell’s essay “In Defence of English Cooking,” he lamented that English bread had become “a pale, fluffy, tasteless thing” thanks to industrial production - but people kept right on buying it. People ate bad industrial bread because it was there, because it was cheap, because it was uniform, and because they couldn’t be fucked baking.

Economists call this the “make-or-buy” decision: a rational actor produces something themselves only when the total cost, including time and opportunity costs, is lower than the cost of buying it from someone else. The total cost, though, is almost always higher than people guess - because they forget to account for the mental overhead. Baking bread takes flour and yeast, but it also takes planning. You have to remember to buy ingredients and start the machine. You have to accept that homemade bread goes stale faster, because it doesn’t have the preservatives that give Wonder Bread its uncanny shelf life. The machine needs cleaning afterward. Each of these steps is minor in isolation, but they build on each other, and the mental cost of doing something yourself, over and over, across a lifetime, is enormous.

And that’s why my bread machine sits unused.

I can make bread.

I have the capacity. I have the skills and the materials.

The ingredients are cheap, and the machine is one button.

But the mental cost of buying bread is even lower: pick up the loaf, put it in the cart. The industrial bread supply chain has condensed thousands of years of baking knowledge, logistics, quality control, packaging, distribution, and shelf-life management into a trip to the grocery store, and the result is worth more to me than the three dollars I would save by making it myself.

Why SaaS is bread, not a bread machine

The argument for SaaS being doomed: AI coding tools have made building software nearly free. You can spin up a custom CRM or a custom analytics dashboard in an afternoon with a good model and a decent prompt. The code is cheap. The infrastructure is cheap. The expertise required is plummeting. Nobody will pay a monthly subscription when they can build their own equivalent for free.

The ingredients cost pennies, the machine costs a hundred bucks, the recipe is public. The bakery is doomed.

But the bakery isn’t doomed.

When a company pays for Notion, or Jira, or Basecamp, or any other tool, they’re paying for what thousands of engineers, compliance officers, security auditors, and domain experts have built and refined over years, sometimes decades. They’re paying for the institutional knowledge in the codebase, the integration ecosystem, the regulatory certifications, the support infrastructure. They’re paying for reliability, predictability, and the peace of mind that comes with knowing someone else keeps the lights on.

A company that decides to build its own version using AI coding tools is buying a bread machine. The ingredients are cheap, and the machine does most of the work, but they’re now the baker. They own the maintenance, edge cases, and security gaps that AI-generated code tends to introduce; AI-generated code has about 1.7 times as many major issues as code written by humans. They own the compliance audits and the 2 AM phone call when the tool breaks and someone has to fix it. And six months later, the person who built the thing has moved to another team, and nobody else understands how it works.

What’s at risk

A tool that converts PDFs to spreadsheets, a tool that generates meeting summaries, a tool that sends automated follow-up emails, etc.: these are single-function products whose whole appeal is a feature that an AI model can now replicate with a prompt. And yes - for a segment of their user base, they are incredibly vulnerable.

But the durable SaaS companies, with deep integrations, proprietary data, compliance certifications, years of domain logic, and ecosystems of partners and consultants, are the equivalent of the industrial baking complex that produces seventy million loaves a day. You can build your own version of what they do, just as I can bake my own loaf of bread. My ability to bake a loaf doesn’t threaten the commercial baking industry, because bakers aren’t selling flour and recipes. They’re selling convenience, consistency, accountability, and someone else to blame when things go wrong.

The Roman plebs understood this five thousand years ago. They could have baked their own bread. They chose not to. Industrial bakeries understood it in the 20th century. The American consumer understands it too, buying 10 million loaves a day despite having every tool and ingredient needed to make their own.

What I think will happen next

I think the SaaS companies that survive will be the ones that understand they sell convenience and accountability. Customers want the supply chain that gets the loaf to the store, and someone to call when the loaf goes bad. AI reduces the cost of making the loaf. It does almost nothing to reduce the cost of building the supply chain.

SaaS pricing will change. Per-seat pricing, which made sense when humans operated software from their desks, will give way to usage-based and outcome-based models as AI agents become a new class of software user. Some thin, single-feature products will die, and they should, because they were never businesses in the first place. They were features priced like businesses during a period when building software was so expensive that even a trivial product could command a subscription fee.

But the core idea behind SaaS, that you can rent a solution to a problem instead of owning the problem yourself, is what has kept commercial bakeries in business since the Roman Empire. It runs on something more basic than technology: people, and the organizations they build, will always prefer to pay someone else to handle complexity if the price is reasonable and the trust is there. Call us lazy bastards, call us pragmatists - we love sliced bread.

In this video, I look at the Easterlin Paradox, the research on income and life satisfaction, and why more money often fails to make people proportionally happier. The answer is not that money is useless. It’s that most people are shopping in the wrong aisle.

The evidence points to three better ways to spend:

Buy experiences, not things

Spend on other people

Buy back your time

Money matters. But it matters less than people think, and it works better when used to create memories, connection, autonomy, and relief from time pressure.

The wrong things are easy to buy. The right things take more intention.

In this video, I explore the cultural, historical, and psychological roots of our obsession with busyness - from Veblen’s theory of conspicuous leisure to Seneca’s warnings about wasted time, from the Protestant work ethic to Parkinson’s Law. Along the way, I examine how we use email inboxes, overflowing calendars, and delayed replies as props in a theater of pseudo-productivity, and why we seem unable to stop.

Topics Covered:

• The performance of busyness and why exhaustion has become a status symbol

• Thorstein Veblen and the inversion of conspicuous leisure

• Seneca, On the Shortness of Life, and ancient Rome’s relationship to leisure

• Max Weber, the Protestant ethic, and the moral weight of work

• Herman Melville’s Bartleby and the emptiness of bureaucratic labor

• Parkinson’s Law: why work expands to fill the time available

• The psychology behind simulated overload and existential dread

• How we use busyness as a competitive dominance game

• Reclaiming true leisure in a culture that treats rest as a moral failure

References & Further Reading:

• Thorstein Veblen — The Theory of the Leisure Class (1899)

• Seneca — De Brevitate Vitae (On the Shortness of Life)

• Max Weber — The Protestant Ethic and the Spirit of Capitalism (1905)

• Herman Melville — Bartleby, the Scrivener (1853)

• C. Northcote Parkinson — Parkinson’s Law (1955)

Key Quote:

“We’ve created a society where we’re actively harming our physical and psychological well-being to maintain an illusion nobody believes. We all know everyone else is faking it too — yet we refuse to break the spell.”