2025-06-23 21:25:27
For context, I run what used to be the 2nd biggest newsletter on substack by revenue and the biggest by far by paid subscriber count. Apparently they're trying to raise money again at what looks from outside like a pretend-up round; here's what I'd want to know if I were an investor. (Everything here is speculative, I do not have inside information).
As best I can tell, Substack's One Weird Marketing Trick was leveraging the economic interests of traditional media employees against their publishers to get positive "earned media". This is clever, and apparently effective! I'm not sure it's a trick available to many other startups, but it's an interesting thing to noodle on.
When buzzy articles first came out about Substack, people would say "it's crazy that journalists are writing these glowing profiles of their competitor!!!!" But this gets it wrong: Substack competes with publishers like The Atlantic, but it competes for writers at the Atlantic. And since Substack has long had a VC subsidy to throw around, it can compete for those writers at higher prices than most magazines can.
If you're a writer at a legacy publisher and there's a new company in town who is promising to pay writers a lot of money, this increases your leverage against your own employer; it makes sense for you to gush about this new alternative employer for writers. I think the right comparison is well-funded media companies of the past like FusionTV, who hired writers at competitive salaries and got a lot of coverage.
Early on, the coverage of Substack was truly ridiculous: there was a time when e.g. Substack added a feature to allow publishers to change colors of their websites, and got gushing standalone coverage in the Verge. For a while I thought the fawning was just because Substack had raised a lot of money, and people confuse fundraising for income. But competitor Beehiiv launched in 2021, got a bunch of VC funding, and brought in various famous writers e.g. a popular fitness influencer named Arnold Schwarzenegger.
Beehiiv claimed $15 million revenue in 2024, and on previous growth trends will be claiming $30 million revenue at the end of 2025; I suspect they may have more real recurring revenue (more on that in a minute) than Substack. But you still hear infinitely less about Beehiiv than Substack. Why?
Partly it's just self-fulfilling: once you become A Company That People Write About you're a Company That People Write About, and journalists with a quota can just file a fluff piece about whatever random junk you did today and pass the Nobody Every Got Fired For Writing About IBM test. Some of it is possibly the consequences of the paid PR ecosystem. And part of it is Substack's annoying-to-me but ultimately successful gambit to brand-smother actual writers and publishers, while other platforms are much better about letting publishers get credit for their own work.
But ultimately, I think the secret of the Substack Story (TM) is that it gets disproportionate media coverage because it offers lots of money to writers, and (consciously or unconsciously!) writers can then go back to their employers and say "hey wanna see my BATNA? Substack sets my BATNA."
When I say "offers lots of money to writers", I mean that (as best I can tell, though I cannot know for certain: my experience is that publishers who sign deals with Substack do not then talk openly about the contents of those deals), Substack has been compensating famous writers and publishers to be on its platform since day 1, in a way that other platforms are not doing. They suffered some controversy for this in 2021 with the "substack pro" product, which gave "advances" to famous writers to join. But my sense is that the extent of Substack-paying-publishers has never been reported properly: that many important publishers on Substack are getting many special deals and arrangements, in a way that might scare investors if they knew about them.
Why does this matter? Because, per Newcomer, "Substack is telling investors that it’s currently generating about $45 million in annual recurring revenue. The total subscription revenue flowing to Substack creators is roughly $450 million, sources tell me." That implies a 10% take on creator revenue, which is the public "standard" deal. But if in fact a decent share of that $45m is being rebated to publishers – in cash or in kind – to keep them on the platform, the company's economics are completely different from what they seem on the outside.
If I were an investor, the first thing I'd ask about is Substack's "enterprise" offering. If an individual publisher is (supposedly) responsible for more than 1% of Substack's nominal revenue, it becomes really important what deal that publisher is actually on. And there are many ways to rebate to a publisher, for a platform that is willing to do so.
Another "tell" I'd look at is when an established mainstream writer moves to Substack and launches with a ․substack․com domain instead of their own custom domain – again, I'm sure some of these people are on the public Substack plan, but if I were an investor I would try to get a hold of these people and ask in some NDA-circumventing way whether Substack is giving them a special deal.
2025-06-20 21:57:19
People talk about how AI will enable "the first one-person billion-dollar business"; I find this very dumb and it aggravates me. (I can't fully explain why I find this annoying, out of all the dumb things in existence, but so it goes).
Basically, "one person billion-dollar business" feels like a fact about your legal setup and contracting decisions rather than a real fact about your business.
I have no idea what her business situation is like but I'm pretty sure JK Rowling could have been a one-person billion-dollar business if she outsourced everything to contractors. Why should I care if she hires a full-time employee accountant vs signing a non-employee contract with an accounting firm? I'm sure the "one-person business" people are pointing at something, but I don't know what it is.
There's an economic model I've had vaguely in my head for a while, but which I've never really concretized, that's roughly like this:
Once upon a time, if you lived in a village and played the fiddle, you had a local captive audience that couldn't hear music easily except from your local band. You could get a ton of Live Music Performance Reps in with an appreciative audience, and after a while you'd be good enough to go to the nearest town and get more reps with a bigger audience, and eventually you could move to the city and become a fiddle superstar. I'm sure you had lots of other problems but in terms of your fiddle–playing this seems really ideal to me.
In the modern day, everything is different. People can listen to world-class fiddlers on their phones all day, or watch videos of fiddle concerts by the world's best fiddlers, and with improvements in transportation (and incomes) even hearing those musicians live is infinitely easier than it was a hundred years ago. And for consumers this is in some sense Good, but it also creates a problem of "how will our next generation of champion fiddlers learn to fiddle?"
Anyway. It strikes me that plausibly AI will create this problem in a whole bunch of new domains. I know there's a future where this is irrelevant because even the best fiddle-player is supplanted by AI two years from now, but suppose we're in a world instead where AI is better than 95% of people at any given task but the best human practicitioners are still better. How do those best human practitioners ever get to be best in a world where their many years of learning-curve are not appealing to any audience because AI provides a better version? Yes you can practice alone in your room for years until you show the world anything, but a) this is very unrewarding, and b) there's some things you can only learn by doing them for other people. I worry about this.
One possible outcome of AI (again, in the short term) is that it's a massive boon to "solo creators" who aren't that great at getting along with other people. In the old days, if you wanted to learn songwriting, you had to be good at songwriting but also either 1) good-enough at playing music to perform your songs, 2) good-enough at friend-making to find someone who would sing your songs. To the extent that AI creates a good-enough complement to all kinds of skills like this, the benefits accrue disproportionately to people who aren't good at finding human partners to work.
2025-06-18 23:36:19
When the yoga instructor repeats, before every posture – not just once at the beginning of class – that you can not-do this posture if you don't feel comfortable with it, this is inexplicably hateful.
When you do a favor for a friend that involves a large amount of time and effort, plus a small amount of money, and your friend venmos you the money, this is inexplicably hateful.
At a party, when you're suffering through conversation with someone who doesn't ask you any questions, but you're doing your best to ask them questions and keep things lively anyway, and then THEY make an excuse to leave, this is incredibly hateful.
At a party, when you're trying to get out of conversation with someone but they keep asking you questions and eventually you just have to make an excuse to leave, this is incredibly hateful.
When you don't reply to someone's message, and then you feel bad, and then you keep not-replying because you feel bad you didn't reply sooner, and you're just doing this to yourself and nobody is to blame, this is so hateful.
When you're reading a comments thread about someone who's had a difficult social experience, and then someone else chimes in saying "if that had been ME they would never have got away with this, I would have simply [done thing that's easy to say in theory but hard to do in practice]," this is unbelievably hateful.
When you're walking along the sidewalk behind someone who walks just slightly slower than you do, not slow enough for you to easily overtake them but also just slow enough that you keep failing to get into the walking-groove, this is unfairly hateful.
An attractive person who is also very nice, this is especially hateful.
2025-06-16 21:46:06
When I say The Pillow Book, written by Sei Shōnagon in the late 990s AD, reads like a Tumblr, you might reasonably assume I'm being wry and somewhat exaggerated: "ohhhh, this thing from 1000 years ago is just like things we write today [if you squint real real hard]!"
But I'm not: The Pillow Book just very meaningfully reads like a Tumblr, or possibly a LiveJournal. If Shōnagon was somehow magically resurrected today and started posting on her pillowblog, she could immediately participate in modern gender discourse and you would not realize she is literally one thousand and sixty years old.
For example, in her list titled Hateful Things (she loves making Lists, because of course she does), she frets about her texts after she sends them:
When you send a poem to someone and, after it has gone, think of some small alteration—perhaps only a couple of letters—that would have improved it.
She laments The Ick:
It’s very tiresome when a lover who is leaving one at dawn says that he must look for a fan or pocket-book that he left somewhere about the room last night. As it’s still too dark to see anything, he goes fumbling about all over the place, knocking into everything and muttering to himself, ‘How very odd!’
When at last he finds the pocket-book he crams it into his dress with a great rustling of the pages, or if it’s a fan he has lost, he swishes it open and begins flapping it about. So that when he finally takes his departure, instead of experiencing the feelings of regret proper to such an occasion, one merely feels irritated at his clumsiness....
And being aired / left on read:
When you put a lot of effort into writing a letter and send it off, then spend all your time waiting for a reply, convinced it must be coming any minute.
Finally, after what feels like forever, your own letter gets handed back to you—still folded or tied exactly as you sent it, but so finger-marked and smudged that even the address is barely legible. "The family isn’t home," the messenger says, returning it. Or, "It’s a day of observance; they said they’re not accepting any letters today."
Such experiences are dismally depressing.
The book is composed of standalone segments which are largely either 1) lists, or 2) stories about her days hanging out with the girlies, swapping letters with boys, and pulling off pranks. I'm telling you, Sei Shōnagon just is a blogger, inexplicably writing in 1000 AD. Look at this list of Pretty Things and tell me it couldn't be a series of image macros hashtagged #justprettythings:
The face of a child who has their teeth dug into a melon.
A baby sparrow hopping towards you when you call ‘chu, chu,’ or being fed by its parents with worms or what not
A little girl [with bangs] tossing back her head to get the hair away from her eyes when she wants to look at something.
If you replace the servants/maids with a roommate and switch the voice to first person, you could absolutely make selfie tiktoks out of Shōnagon's laments about waiting for a booty call:
When you have been expecting someone, and rather late at night there is a stealthy tapping at the door. You send a maid to see who it is, and lie waiting, with some slight flutter of the breast. But the name you hear when she returns is that of someone completely different, who does not concern you at all. Of all depressing experiences, this is by far the worst.
Or this one:
Someone comes, with whom one has decided not to have further dealings. You pretend to be fast asleep, but some servant comes to wake you up, and pulls you about, with a face as much as to say ‘What a sleepyhead!’ This is always exceedingly irritating.
Or this bit about Hot Priests:
A preacher ought to be good looking. For if we are to properly understand his worthy sentiments, we must keep our eyes on him while he speaks. Should we look away, we may forget to listen. Accordingly, an ugly preacher may well be the source of sin. But I really must stop writing this sort of thing.
Unbelievably, there is even some absolutely literal Delivery Driver Tipping Discourse:
A messenger arrives with a present at a house where a child has been born, or where someone is about to leave on a journey. How depressing for him if he gets no reward! People should always reward a messenger, though he may bring only herbal balls or hare-sticks. If he expects nothing, he will be particularly pleased to be rewarded. On the other hand, what a terrible let down if he arrives with a self-important look on his face, his heart pounding in anticipation of a generous reward, only to have his hopes dashed!
I could go on, but you should read the book. I recommend one of the modern-er translations: I'm reading the 1967 version by Ivan Morris, and there is a 2006 version by Meredith McKinney. I got some of the quotes for this post from the 1928 version by Arthur Waley, and find it a little fusty; it blows my mind that a century-old translation can feel super old-fashioned, while millenium-old content feels fresh.
Let me leave you, like a good lover, with this one. Sei Shōnagon, we lift our pillows to you.
It is important that a lover should know how to make his departure. To begin with, he ought not to be too ready to get up, but should require a little coaxing: ‘Come, it is past daybreak. You don’t want to be found here ...’ and so on.
One likes him, too, to behave in such a way, that one is sure he is unhappy at going and would stay longer if he possibly could. He should not pull on his trousers the moment he is up, but should first of all come close to one’s ear and in a whisper finish off whatever was left half-said in the course of the night. But though he may in reality at these moments be doing nothing at all, it will not be amiss that he should appear to be buckling his belt.
Then he should raise the shutters, and both lovers should go out together at the double-doors, while he tells her how much he dreads the day that is before him and longs for the approach of night. Then, after he has slipped away, she can stand gazing after him, with charming recollections of those last moments.
Indeed, the success of a lover depends greatly on his method of departure. If instead he springs to his feet with a jerk and at once begins fussing round, tightening the waist-band of his breeches, or adjusting the sleeves of his Court robe, collecting a thousand odds and ends, and thrusting them into the folds of his dress, or pulling in his over-belt—one begins to hate him.
2025-06-13 20:51:03
Here is a thing that happened to me once, that I feel like I should document publicly but isn't enough for a full post: one time I went to Kenya and took precautionary deworming pills, after meeting a couple Kenyans who were like "yeah I take them every year whether I need to or not, just in case, kind of a detox thing."
When I got home from this trip I felt 50% less obsessed with my cat, who (to be clear) I was 100% too obsessed with previously. Like, I used to come home early from parties because I was worried about her, and generally spend all day thinking about her and worrying about her wellbeing.
After coming home from this trip I was just the normal and objectively-correct amount obsessed with her (she is a great cat).
Is it actually possible that I had cat-worms, and the dewormer got rid of them? I feel like the answer is probably no, there was something else happening and this was just a coincidence, but it's such a bizarre thing that I wanted to document the possibility.
I am generally pretty flabergasted about how little we document the effects of medical interventions. Like: as best I can tell, there are tons of interventions that we give to thousands/millions of people and there is no post-intervention surveying of how it affected them? There's an Adverse Effects Reporting System but 1) that requires pro-activity from people, 2) I think people generally don't report mildly-bad but not terribly-bad adverse effects, even if those mildly-bad effects are worrying in aggregate, and 3) it doesn't track non-negative but still meaningful side effects.
Does anyone know why things work like this? Is there a reason we don't randomly survey n% of people who get any given treatment, and then just see if there are patterns of effects that emerge from that? It feels like this would be far more useful than most surveying, and not very costly relative to medical costs overall.
2025-06-11 21:28:11
Here's my public policy proposal: when you have a phonecall (or videocall) with a company, and they make a recording, they should be legally obliged to share that recording with you.
There are too many times now where I've called (say) an airline or cellphone company, they've told me something specific, that something turned out to be false or misleading, but I have no provable record to point to.
If they had written the same thing in an email I would have some leg to stand on in trying them to do the right thing based on their information they themselves gave me – yes I still probably wouldn't have been able to do anything about it, but at least it would be slightly easier to say "here is what you said, why did you tell me that?"
Sometimes (when you have previously called a company) the company is willing to listen back to the recording on their side, but they won't let you listen to it too. So they can just say "we listened to the recording and decided to take no action," which sucks real bad.
I think the future is going to be even worse in terms of bad information from company phonecalls once the entity on the other side of a phonecall is an AI, and if companies aren't forced to be legally responsible for the things their AIs say. So long as the proof of what was said on a call is only available to the company and not the customer, there is ~0 chance of the companies staying responsible.
I know that unfortunately this proposal might not be possible with e.g. banks and hospitals, who 1) really do have a ton of regulation about securing the privacy of your data, and 2) also screw their customers around a lot.
Alas: something is better than nothing, and every company who can share a recording should be forced to do it.