michael-dean-k/

Topic

creator-economy

7 pieces

Avoid shipping logistics

· 466 words

I resonate with the vision of Metalabel—artists collaborating and splitting royalties—but after finishing a project with it (The Best Internet Essays 2025), I’m not sure if I’d use it again for a self-published print book. I imagine this works so much better with a digital product, but for a physical deliverable, I found the convenience of automating the royalty split to not be worth the friction of handling shipping. (I’ll describe my process, and if I did something wrong, please correct me.)

All purchases happen through the Metalabel storefront, and from there you can export a CSV that you can bulk upload into a tool like Lulu (an online printer). I decided to offer the anthology (The Best Internet Essays 2025) for a limited window, otherwise I’d have to handle shipping logistics at a daily/weekly level. But even with a single shipment, I ran into trouble. The first issue is that a lot of countries require a phone number for shipping. Metalabel didn’t collect that, so I had to put 1-111-111-1111, which got flagged for some countries, requiring me to use my personal cell phone. Other countries required a tax ID, and I’m still waiting to hear back from the buyers so I can ship them their copy. Another thing I didn’t think through is the return addresses. I assumed that the printer would provide their own address, but instead they used the name/address from my credit card, which I did not intend to share! I’ve been writing under a pseudonym, and this doxxed my last name to anyone who purchased.

The other problem was that so many people—in real life and online—were confused why the sale had an end date. Books don't typically have deadlines. Even those who knew the deadline procrastinated, and were bummed when they remembered they forgot. Again, my decision, specifically because I do not want to be regularly porting over CSVs and manually handling the edge cases that are inevitable.

In the future, I’ll likely set up a storefront where a reader can purchase it themselves, input their address and any required information for their country, and then get their own unique tracking ID. And, considering so much effort goes into making a book, I wouldn't want to limit it to a one-month window; I'd want it open forever, or for years, at least. If I do a royalty split again, I can set some interval, maybe once per quarter or year, and then ask the contributors to invoice me. None of my friction above was specific to Metalabel functionality (the whole platform as it is was very pleasant to use, and it's Lulu that I'm frustrated with), but because they aren't integrated with a shipping platform, it requires logistics that are annoying and avoidable.

Do paid subscribers influence discovery on Substack?

· 546 words

Chris Best, founder of Substack, posted that they caught “President Plump,” the #1 growing account on Substack, for using fake subscriptions to boost discovery. I think this was intended to comfort everyone that they caught a scammer (justice!), but actually it confirmed what many were starting to notice: discovery is contingent on you making money. If you have paid subscribers turned off, no algorithmic wind will blow your way. But if you have a spike of paid subscribers in a month, suddenly your old posts will start to go viral, in hopes that even more paid subscribers will bring the platform 10% (this has happened to me before). This isn’t inherently bad. For every President Plump, there is an earnest person trying to finance their creative project.

But at scale I fear it creates a bad pattern, because the accounts that everyone sees will be the ones making the most, and generally these will be marketers and growth hackers more than artists. I think you will find better writing in the gutters of Substack than on their rising leaderboard. If authentic culture emerges outside of monetization, then there’s a real rift between what Substack wants to be (“an engine for culture”) and what it actually is (an algorithm that only rewards monetization).

I think the best we can do is use this information to our advantage. For example, I could have new Essay Club members pay directly through Stripe, but by handling payments through my Founding Members tier on Substack, I get a discovery boost, which is worth the 10% fee. Similarly, if you make small digital products, it might make sense to bundle them into a subscription instead of charging per item.

Should you use a credit card masking service to give yourself 20 paid subscriptions for $5 each? Depends. Basically, for $10/month, you can pay for a probably noticeable increase in discovery. The question is, will you get caught? Maybe they are on the lookout now, but my guess is they would only penalize it at a certain scale. Sam Kriss speculated that President Plump was paying himself around $5,000 per month to reach #1. I’ve never done this, and wouldn’t necessarily recommend it unless you have a hacker mentality and really need the growth. 

At the very least, you should consider having paid subscriptions turned on. Cate Hall found success in charging $1/month and getting to #1 rising. Our very own Yehudis Milchtein also set up $1/month subscriptions and is now #91 rising in literature.

However you approach this, it brings up a bigger question for me on how to build a real engine for culture. It seems like you can’t have an algorithm for a single reward (popularity or money) or else they will be gamed; instead you could give everyone curatorial power relative to their cultural reputation, however you measure that. For example, if we all trust Ted Gioia, then somehow Ted’s like should count more than 10,000 bot likes or $1,000 in fake subscriptions.

I hope this triggers more transparency from Substack on how their algorithm works, and also hope for a new generation of platforms where each person has visibility into and control of the thing that is routing them information.

Medusa of Marketing

· 29 words

It is important to avoid learning best practices for marketing, for that’s like seeing a Medusa that turns your tongue to stone and never lets you be real again.

Why doesn't Substack create funds for it's on-platform creators?

· 232 words

I didn’t realize that Substack is open about paying off-platform creators to join their platform. See their $20m accelerator fund. My quick understanding is that, if you make $X revenue/year elsewhere, they guarantee you’ll make that, and will make up the difference if after a year, you don’t. A friend thinks there’s an additional secret fund that pays bonuses for celebrities to join (ie: Dolly Parton, Charlie XCX). I was surprised by how articulate Charlie XCX was—I only have a meme-level understanding of her—but I suppose it’s possibly ghostwritten. Idk.

I don’t have problems with this, but what doesn’t register to me is why they wouldn’t allocate money to help the on-platform, original writers. Obviously, these kinds of things piss of 95% of their userbase. Even if there was something like $100-$1m for on-platform writers with audiences under 1,000, that would build a tremendous amount of goodwill. My guess (and fear) is that they have a business model blindness, and aren’t thinking along the planes of “what actually builds organic culture?” Instead, there’s a lot of rationalizing: “here’s why bringing Derek Thompson on platform is good for you” (but the obvious benefit comes from the 10% they get from DT).

It’s weird to me that in some sense I’m giving more to it’s existing writers ($10,000), than the platform that raised $100,000,000.

Substack's business model blinders

· 200 words

Just heard Hamish (on a livestream) say that Substack is a revolution, a “found economy,” that materialized 5 million paid subscriptions that wouldn’t have existed otherwise. What is a revolution though? I think I want to zoom into this positioning, because many words are being used interchangeably. Yes, it’s a new business model for monetization, but is that a “cultural revolution”?

It feels like there’s a bit of a fixation on the 10% mechanism, and the risk is that this reward function turns Substack into LinkedIn in the next 3 years. If the goal is to make a “culture engine,” you need to really ask what a culture is. If you’re culture is limited to paid subscriptions, it’s a small, unrepresentative, utilitarian culture, much more slanted to journalism and business tactics, regardless of an editorial attempt to bring a flair of literature.

We need to define culture (in terms of taste, values, and quality), and then make platform design decisions that have nothing to do with revenue. Of course, I’m not saying to abandon revenue focus; I’m saying that they need to allocate some percent of their attention to “doing weird things” to prevent a writer exodus as enshittifcation strengthens.

Despite the superwriters...

· 186 words

Will was surprised to learn that I think machine writing could soon surpass the best human writers. As the head of Essay Architecture, he thought my position would just be “no matter what, humans will always be better at writing essays than machines.” I actually have some pretty extreme predictions on the trajectory of technology (I guess you could say I'm an ambivalent accelerationist), but I guess I believe that AI progress is irrelevant to the fact that I will always enjoy writing and see writing through the chaos as an opportunity. So yes, I think machines will make essays that are history-defining, that are good to degrees that are unimaginable to us today.

This will, unfortunately, make it even harder for writers to have economic value; but realistically, it's already too hard. The Creator Economy is a game of power laws, and AI might shift the chance of success from 2% to 1%. But could the same technology help artists go from 1x potential to 20x potential? If AI kills the market for commoditized creative work, will it let humans focus on the right things?

Fear and loathing at Substack notes night

· 98 words

I don’t know the New York they write about in classic essays, because all of those are from the perspective of an out-of-state romantic, an Oklahomer, who moves into the fast lane of Manhattan and thinks it’s the only speed to live in the city. But actually the best way to exist in New York is at the edges. For one, you can see the skyline, but really, you get the perks of a normal life with the convenience of being a train ride away from the center of the world. I just got a last-minute invite to an event at Substack’s NYC office and so now I’m going. 

The guest list was full when I last checked it, but I must have been on the waitlist and some spots just opened up. It’s 4:30 PM and I have to make it to 25th Street by 6 PM (so again, nice to be able to get to the center of the world with almost no notice). I live in Queens, so I shifted a meeting, made plans for my mother-in-law to pick up my pregnant wife, took a shower, and headed out. En route, I reread the invite:

“Hear directly from our product and partnerships teams with a behind-the-scenes look at the Feed: what’s working, what’s next [emphasis mine], and how to grow and connect through Notes. There’ll be live demos, insider tips, and plenty of time for Q&A.”

My hope was to learn the future of Notes, the “feed product” that Substack is nudging everyone into, the place where many longform writers loathe. For the record, I have a history of being a Substack evangelist, and as recently as last week, I went hard on a friend: “Notes isn’t the problem; you’re the problem.” What I meant was that, a social media feed will always be imperfect, but it’s the best way to write in public, and since Note is the best option around, it’s each of our responsibilities to set a productive mental frame so we can show up as “citizens of the Internet.” It’s up to us to make Notes a place that’s worth spending time on. Personally, too, now that my career effectively depends on me talking about Essay Architecture in public, I feel the need to trick myself into loving Notes.

I was led to believe we would have a glimpse at the roadmap, some new vision, but mostly, this event confirmed a sinking suspicion: although Substack describes its own algorithm as a noble alternative, it’s just as optimized for revenue as the enshittified feeds it claims to be above, and could have a similar cultural conclusion.

The first thing I noticed when walking out onto the 12th (?) floor was that everyone was loud, beautiful, and extroverted. These people write? I would’ve guessed it to be an Instagram crowd. I recognized three people: I saw Hamish McKenzie, the CEO being mobbed by a crowd of schmoozers—who I would have loved to talk to—, I saw … Jamie? … a writer who recognized me last meetup, but I’ve forgotten her name, and I saw Daniel Pinchbeck of Liminal News (which I pay for) who writes about politics, psychedelics, and the occult, and who I imagined to be similarly uncomfortable with the vibe (I don’t know what he thought, but he did leave early).

At 6:10 PM, before Hamish gave his traditional pitch, he thanked us for baptising the new NYC office, and acknowledged it was his first time here too (this got me to believe, out of the gate, that the purpose of this get-together was to welcome the boss). I assume this office is possible because of the Series A round from a16z. We got the stats, good stats: 32 million free subscribers, half a million paid, and you’re 7x more likely to be shared within the app. He comforted us, told us they won’t follow the same fate as X or Facebook. “As you can tell, our culture is different.”

Soon, after the “head of social media” presented, but as if the room had never heard of Notes before. We got tips, but mostly, we were shown the different archetypes. We could be a “Tumblr Girl” or a “Reply Guy” or one of several other pre-packaged attitudes, and she showed memes and everyone laughed. She said she knows that writers hate to market their own work, and then showed an image of a writer’s Note showing their audience growth graph. We saw Viv Chen’s self-help note, proof that one note can get you 32,000 likes and $5,000 in paid subscribers. Paul Staples was in there too. I didn’t get the sense that Notes was about promoting our own work at all; I got the sense that Notes was about being snarky and ironic, campy and performative. There wasn’t one note with a paragraph. She closed with “so if you didn’t find those notes (her examples) funny, you’re boring and need to rethink your attitude.” The room roared.” (The room roared a lot, especially at tip #5, which was “visualize success and manifest it.”)

She almost forgot to show us new features. One: if you’re a publication with multiple writers, you can now add @ to write a note from a specific editorial staffer. Two: there’s a new embed format to crosspost to LinkedIn. Reminder: this is the roadmap update I rearranged my night for.

Finally we heard from Mike Cohen, “head of AI/ML,” the guy in charge of the feed. His goal is to turn people and content into numerical representations: it’s his job to figure out who you are, what you like, what’s out there that you’ll like, what will get you to subscribe, and ultimately what will get you to pay. This is the reward function. How do you get paid? Because that’s how they get paid too. This is noble, sort of. He made a point that the world “algorithm” has soured, but you can build good ones, it just depends what you optimize for. “Yeah, if you don’t like writers getting paid, then you’ll complain about this.” He said it sarcastically, as in, who would question the good intention of getting writers paid? Of course, I like writers getting paid. I’m a writer and I like getting paid! But when you slant the algorithm towards monetization, you pollute the culture, you elevate the growth-hackers, marketing businesses, and media companies, and you drown out the artists, the weirdos, and the free press.

His last question was what the roadmap is for the next 2 years, and we got, “we’re always trying new things … always tweaking the core retrieval engine … we keep iterating if what you see is relevant at all times … until what you see is perfect, which will never be.”

I feel like this would be a wasted trip if I didn’t personally talk to Mike Cohen and try to confirm my conspiracy theories on how the feed works. After my terrible warm open (“look my name is Mike too,” pointing at my name tag) I asked him to confirm it. I said that in November 2024 I hosted a workshop that brought in $10,000 founding tier subscriptions in a day or two, and unexpectedly, an old post of mine (from Nov 2023) started going mega-viral. It went viral for months. I asked him if the algorithm resurfaces posts from writers who are generating revenue. He said yes, but not revenue, subscribers. I clarified, paid subscribers? “All subscribers, but yes, even more so paid.” So it seems like paid subscribers are the strongest boost you can get.

Selfishlessly, this doesn’t bother me. I know what I need to do. By doubling down on paid subscriptions, I’ll be able to grow my audience faster on the platform. This validated my decision to host my book on Substack and not my own website. If I were mercenary and bold enough to hack the system, I’d set up some discount codes for 90% off, and set up 100 fake accounts through different VPNs, so for $100/month, I could be top of the Rising charts and hack the algorithm. I would bet this is exactly what lots of these AI-generated growth accounts are doing. I wonder if this is detected and manually banned though? Probably not worth the risk, especially because I already have a solid paid content strategy, but I imagine once people realize this, it will be rampant.

But, if I think outside of my selfish needs—and my confidence to crack Notes, eventually, somehow—, I think it’s a bad algorithm for culture. Yes, it’s framed as “for creators,” and it is, but there are side effects if money is the main attractor. It means that hucksters, partisan politics, slop, and smut will thrive. Effectively, it means that even though Substack says they care about culture, its algorithm doesn’t actually. Substack has an underbelly of amazing writers who simply can’t and won’t monetize their prose, and for that they will be lapped by salesmen. I shouldn’t have been surprised, but I was unable to articulate the source of a low-grade depression for the last few hours, possibly because the illusion popped; there really isn’t a place on the Internet that is unreasonable enough to defy economics and do something for culture’s sake. 

Before leaving, I asked Mike if they try to measure quality—I mentioned that I do this, and got a vague, “oh, cool”—and he said, “you know, I wonder if writers stopped writing and just used AI to generate their posts … if that got more readers to pay for their work, is that really so bad? Who are we to decide what’s good?”