How do people earn a living on Substack? What does it mean to be a worker when you’re an independent “creator?” What could organizing look like in this weird, disparate media paradigm? I got a chance to talk about labor in the creator economy with two outstanding writers on Substack: rayne fisher-quann, who writes at internet princess, and Katie Gatti Tassin, who runs Money With Katie and cohosts the Diabolical Lies podcast.
This is the first Substack Live I’ve hosted at How Things Work. It’s also a product of the work of a group of fellow writers on this platform who have been discussing these issues for months now. More than 800 people watched the conversation live, and you can watch the video above. We hope to be hosting more conversations like this with other writers in coming months—you can follow thesubclub.substack.com to stay informed about future talks and organizing efforts. A full transcript is below. Feedback is welcomed. The first step towards solidarity is talking to each other.
Transcript
Hamilton Nolan: I’m very lucky to have these two people with me today. My first guest is Rayne Fisher-Quann. She is an organizer, writer, and cultural critic. Her extremely popular and successful Substack is Internet Princess, and she has a book in the works called Complex Female Character, so look out for that. Rayne, thank you for being here.
Rayne Fisher-Quann: I’m so happy to be here.
Hamilton: And my other guest is Katie Gatti Tassin. She is a writer about money, culture, and class. She is the author of the bestselling book Rich Girl Nation. Her Substack is Money with Katie, which is also very successful and popular. And she is the co-host of the successful and popular podcast, Diabolical Lies. Katie, thank you for being here today.
Katie Gatti Tassin: Thank you. I’m feeling successful and popular!
Hamilton: The average of the three of us is successful.
The first question I want to ask you two: a lot of people can’t earn a living on Substack, whereas you are people who actually are earning a living on Substack. What does it actually look like to earn a living on Substack? How does that work?
Rayne: When we were first talking about doing this Live together, my first concern was: I don’t know if my experience making a living is representative of the average person on Substack. I’m so lucky to be able to make a living on this platform. I’ve been able to do it for a long time. I started Substack about five years ago, when it looked very different from now. There wasn’t an app, and there also wasn’t even really a centralized Substack website. It was really just an email delivery platform. You couldn’t go to substack.com and see any feed or anything of value. When it started, it was really just a way for me to connect people to my writing: they would give me their email address and I would send them emails. I miss that a lot, honestly, in terms of how Substack works now. I think when I monetized my Substack, I was twenty.
Katie: Wow.
Rayne: Perhaps because the platform was less saturated, and perhaps because it worked a little bit differently than it does now, I was pretty immediately able to make a living. I quit my job almost immediately, which was profoundly unbelievable. But even has my subscribers have increased, my income has remained relatively the same through all of those years. I do think that the way I use Substack is a little bit different, and I don’t actually use it to optimize my income. I don’t actually think of it very much as a job I do to make the most money I can possibly make. But I’ll pass it over to Katie.
Katie: You’re like, “I don’t really do this job to make money.” And I’m like, “Hi, Money with Katie here!” I think constantly about income.
I have a different experience from the standpoint of being a late adopter to the platform. I earn money on Substack in two different ways. The first way I started, and the primary way, is through my podcast that I co-host, Diabolical Lies. That has been an interesting experience because I think we were one of the first. There are a lot of publications on Substack that have podcasts attached to them, but the primary product is still an editorial, written product. Whereas we launched the podcast Substack-first and Substack-native. We started in the summer of 2024, and then we turned on paid subscriptions and started offering paywalled, gated episodes. That was when I was still working at Morning Brew, running Money with Katie for them.
So this past January, when I bought my intellectual property back from Morning Brew, it just made sense to bring my Money with Katie newsletter to Substack, but I didn’t really want to monetize it in the same way. Having seen how things have progressed even just in the last couple of years that I’ve been on the platform, I do think that it’s very difficult to get people to pay for work consistently. And I was a little nervous about that feeling of obligation. I was on a weekly cadence, and I really can’t skip a week if people are paying for this. There was just a level of pressure I’ve wanted to avoid as much as possible. So I continued monetizing Money with Katie the way we had been at Morning Brew, which is via sponsorships — native sponsorships that my business manager negotiates with our partners. So it doesn’t run through Substack.
It’s an interesting dynamic, where the platform is not making any money on Money with Katie, despite the list being quite large coming from Morning Brew, because we are monetizing off-platform and negotiating deals directly with sponsors. It’s been fascinating to see the pros and cons.
The delivery platform that it was when Rayne started, and the way that it has evolved now into more of a social platform — I have mixed feelings about that, because the network effects have candidly been really nice for me, having come from a media company where we had to fight for every new email, and there was no way for people to easily share your work or for you to connect with people doing similar work. So I’ve really appreciated that.
But with the introduction of an app-first platform — and obviously the company wants people to use the app — I have noticed that I will get emails from people who are like, “I don’t get your newsletter anymore.” And I’m like, “Oh, do you have the Substack app?” And they’re like, “Yeah.” And I’m like, “Well, that’s where it is.” And there’s really no way to bypass that if they have that setting turned on to receive things on the app. So there’s just little things like that I’ve had to work through that I wasn’t necessarily expecting. But it’s been interesting to have two different publications that are monetized in radically different ways running simultaneously on the platform.
Hamilton: We have a very good range on this panel, because I basically just washed up here because the journalism industry collapsed. I beg for money here, and that’s my career now.
Rayne, you said you’ve been holding steady, essentially, which is a little bit mind-blowing considering the incentives that I feel like are put on all of us for growth, growth, growth on Substack. Why is that? What does that look like for you? And how do you think about growth on Substack?
Rayne: The truth about me, which is maybe annoying to say, is that I don’t care about making a lot of money. It actually makes me uncomfortable. I was raised in a household where money was really scary and stressful. Money makes me feel sick and scared. So I’ve really never had the thing that makes me want to make the most money I can make.
When I started Substack, and when my newsletter started to do well, I started to have a lot of conversations with the Substack team where they were talking to me about what they saw for my newsletter and the things I could do to make the most money. Pretty immediately I was like, “I don’t want to do any of that stuff.” I also have a bit of a gut revulsion toward the idea of chasing infinite growth; that’s never been what I want to do. And unfortunately, I’m just quite stubborn. So I’ve built a model on my Substack that I think is relatively unorthodox, where I’ve always just been like: I’m going to put out an essay that I put a lot of work into, maybe about once every six weeks — that’s where it tends to land these days. And most of the time it’ll be free. If you want to support me, that’s what the payment is for, just to support this whole project and to support the fact that I don’t do ads, because I don’t want to do ads. So there’s always been about the same amount of people who want to do that, and to me, that’s perfectly great. I prefer not to think about growth or to put that pressure on myself. I’m worried I’m going to sound totally pretentious, but really all I care about is trying to put out the best work that I can put out. I find that that incentive for growth is actually diametrically opposed to what I want to do and what helps me sleep at night.
Hamilton: What about you, Money with Katie? How do you think about growth?
Katie: Yes, same. I don’t care. I, too, have defeated my internalized capitalism to the extent that Rayne clearly has.
No, I think what’s tough about it is the sense of needing to replace churn. And I think there’s also a platform element here – and this is totally a hunch – sometimes my sense of scarcity around it is like, okay, well, if it’s not growing, or if I’m not playing ball or playing the game, there is an algorithm powering all of this. So to the same degree that I kind of got sick of Instagram and I don’t really post on Instagram or TikTok ever – I think I’ve posted on both of those platforms maybe five times total in the last six months – there is a sense of having to do what you feel like the algorithm wants you to do, and that you might get deprioritized if you’re not showing up consistently. Or like with the big push for live video, the creators that are hopping on these features early are going to have an innate advantage. And so I do feel the pressure sometimes.
I think it’s really telling that I’m calling it a “product” and Rayne is calling it a “project,” so I’m going to use Rayne’s language. I feel pressure to respect the project by giving it the best shot at success that it can have and getting it in front of as many people as I can. And I think that any time you’re on a platform that has an algorithm, a recommendation engine of that nature, you are going to see those types of trends and feel some impulse to respond to them.
Although I will say, I think Rayne was smart to not promise anything directly, for subscriber payments. I just don’t know how repeatable that is now. I’m a paid subscriber to both of you and have been for a long time. Hamilton, I don’t think you ever paywall anything?
Hamilton: No, I just put it out there and beg.
Katie: You do the beg-for-tips model, right. And I think I eventually was like, “I’m reading this guy’s stuff every single week, I should probably pay him some money.” Whereas there was something Rayne wrote once upon a time that was paywalled and I really wanted to read it, so I was like, “yeah, I should definitely be a paid subscriber to her.”
I also question how applicable my own instincts and behavior are to someone who’s just a reader or just a listener and this isn’t their job. I think if you are a creative person and you work in this industry, there’s maybe more of an impulse. I don’t even know how many paid subscriptions I have, but I’m sure it’s a lot more than the average person who’s not also putting work out there. So it’s hard to say how common that attitude is.
Hamilton: Every form of getting paid as a creative person has a downside. If you get paid primarily through ad revenue, your advertisers can capture you. If you get paid the way that we do, your audience can capture you.
I was going to come back to you, Rayne, because when we were talking about this before, you sent an email with an interesting line. You talked about how Substack puts the moral burden for fair compensation solely on the consumer. So in other words, your readers have this moral burden placed on them to kind of support you, or else we’re all going to starve to death. Even though some – I think a lot of – creative people would say, you’re living the dream with this setup. Does that direct monetization rub you the wrong way?
Rayne: Well, to be clear, I also think I’m living the dream. I literally think about that every day when I wake up. I think I’m so lucky, for a million things. I love being able to do the work that I do. Something I feel obligated to say in a discussion about Substack is that I don’t have a college education. I don’t have industry connections. A world in which I can have the kind of career that I have from writing is – to me, I don’t think it would have been possible without the internet and without the models of creation that exist now. And so that’s something that I think about a lot and that I’m really grateful for.
But I do have a lot of questions and concerns about what this model means for the wider ecosystem of artistic production and of literary production, which is something that I care about a lot. And when we were talking about how we define labor on Substack and how we talk about writers being laborers, the thing that I thought about right away was: Substack actually talks all the time about writers as laborers. That’s essentially its bottom line, that writers deserve to be paid. And the people who are really supportive of Substack and are kind of real believers in their mission, that’s their bottom line: writers deserve to be paid.
And I also believe that writing is work and that writing deserves to be paid, but I think that, as you were saying, there’s a very interesting paradigm of labor that Substack presents, in which every writer is a small business owner with their own individual class interests, and where there is no – as you know, because you’ve been trying for a long time to think about how we can organize on Substack – traditional model of labor organization that’s applicable here, because of the way that this creator-gig-attention economy works.
When I was a teenager and I was first starting to read essays and read blogs and stuff like that, there was a huge conversation about writers unionizing their workplaces. All of these union efforts in the creative field, I really saw them start to reach popularity and kind of pop off in the 2010s. I think all the time about how now there is this model where some writers can make more money than they ever would have been able to make before, but that money is contingent on meeting certain demands and performing in certain types of ways. And whereas, at one point, people would have been able to organize with their bosses and their superiors, now all you can do if you want fairer compensation is tell your audience, “Please pay me more, because I deserve fair compensation.” That’s a very interesting individualizing dynamic that reframes labor in an interesting and, I think, concerning way.
Katie: Yeah. You did a really good job, when we were talking about this beforehand, emphasizing how it’s strange that this is a paradigm where people who may have otherwise been shut out from a world of media or writing where there were more traditional gatekeepers — that world still definitely exists, but this does kind of feel like a back door in some ways. In some ways the access has never been better, but all of that is contingent upon continuing to view yourself as this atomized laborer going after this scarce resource of readers who are willing to pay for work.
In preparation for this call, I was reflecting on the fact that everything I do that makes money happens through this platform. So for that reason, I’m both very grateful for it and also care a lot about the direction that it goes in, because my livelihood and many other people’s livelihoods completely depend on it. But I mean, we have a very popular podcast on this platform, and I know that if we left tomorrow, it wouldn’t hurt Substack at all. So there’s a real recognition of, like, even with a popular podcast, we don’t have any leverage on our own to force change, or to have any say, really, in the direction that the platform goes. So even quote unquote “big creators” are benefitted by recognizing the fact that, as much as our incentives are aligned with the platform that we create on – and in many ways, when they do better, we do better and vice versa – there are some real ways in which that is not true. And moral neutrality, that is just the reality of how a big media business like this works.
So Hamilton, the effort to bring writers and creators on this platform together to figure out how we can make it work better for all of us, I think that is a really exciting thing to be a part of.
Rayne: It does seem like there’s a limit on how many paid subscribers there are – how many there are to be shared among everyone. And I do think that, especially on a platform where so many people are producer-consumers, where I would guess that probably the people who have the most paid subscriptions are also people who are producing work on Substack themselves, I can’t really think of another social media platform where monetization is so explicitly the imperative for every user. So you have this base of producer-consumers, which creates a vibe of passing the same five dollars around. You have questions about where that goes and what the limit is on it, and the fact that every time you pass the five dollars –
Katie: They get ten percent!
Rayne: And I think not only is there that hard ceiling in general, but there’s obviously a huge skew for which types of newsletters will have the the paying audiences with the highest ceilings. And that’s like business newsletters and fashion newsletters, newsletters that can capture audiences outside of Substack’s specific thing. And not to disrespect that type of work at all, because I think fashion newsletters are really, really great and they do an amazing thing. But the thing that I love about art is that it doesn’t provide a specific tangible value, it often isn’t transactional. That’s what I love about a really good essay. And so sometimes I wonder, when Substack says it’s the future of media and the future of writing, I’m like, well, what happens to writing if it’s funneled toward ends that are only rewarded if they’re extremely transactionally tangible for the reader?
Katie: You know what that makes me think of? I didn’t come from a traditional media background; to the extent that I ever worked in media, it was for a startup where I was kind of off on my own island doing my own thing. I don’t have a journalism background the way that Hamilton does, but it’s my understanding that a lot of the large media organizations that are thriving right now, like The New York Times, it’s actually the Wordl people. They’re selling you the games and shit so they can pay for the actual journalism. I think that’s generally how it works: the classifieds, or the lowbrow material – no judgment – but the garbage stuff, the affiliate links and whatever, that sort of commercial material has always been how these outlets made their money.
But then, and I think this is the important part, there is an active decision to funnel those resources back into the work that matters in those publications. And so I’m just noticing the parallel there. I think you’re absolutely right that there is an element of that recreated in any platform, where you’re maybe more willing to pay for the fun stuff, or you’re more willing to pay for the crossword or whatever. And I think that that decision point, though, of making sure that resources are still being funneled into the stuff that makes the platform work, or that is actually not just going to be good for eyeballs and clicks and the stuff that drives outrage on every other social media platform, but is going to be invested back into the writers and the features that are for the writers and podcasters and not just building up the news feed – that is a decision point. And whether the writers have any say in that, I think, is dependent upon organizing.
Hamilton: You’re exactly right. The style section of The New York Times is always what paid for the Iraq Bureau and whatnot. Now if we’re all disaggregated into our own little silos, it’s all style section and no Iraq Bureau, so to speak.
One of the reasons why we’re having this conversation, and why some of us have been talking for months about what it would even look like to organize people on Substack, is because I came out of journalism and I was in an office with a bunch of people, and now I’m sitting at my desk, like all of us. I’m curious: how connected do you feel to other writers and creators on Substack and in the world?
Katie: I’ve had a pretty positive experience in that regard. I can complain about the algorithm all I want, but at the same time, the algorithm is what brought some of these people into my orbit, because we’re talking about similar things. And so I do feel a level of connection. Rayne and I text now, so that’s pretty cool. But I don’t think there’s any comparison to actually being in person or having that kind of shared cause that you probably felt with your coworkers, Hamilton, working for the same publication and in the same environment.
Much like I was at Morning Brew, running Money with Katie on my own little island, we’re still on our own little islands right now. That is just a structural fact of the way things work right now that is not super conducive to connectivity, unless you’re actively seeking it out. And some people are really good at that, really good at doing collaborations. I haven’t been as good at that. It hasn’t really been at the forefront, I think probably because the collaborations often feel like business moves in and of themselves. It’s like you’re working with another person because you want exposure to one another’s audiences, which is perfectly valid and I’m sure works really well, but you’re still coming into that transaction, so to speak, operating from two different financial universes.
Rayne: I love other writers on Substack. I know a ton of them and I love the social connections that I have with them. I think it’s also really helped that I live in New York and there’s really a literary scene here, and so I’m friends with a lot of writers and most of them I didn’t meet through the platform itself, I just met them in real life. But I’m so skeptical of accepting the promises of the tech company social media thing, where their whole thing is, “Look! you can meet like-minded people!” Where they’re monetizing and commodifying connection. The problem with that is that connection feels kind of dirty. I often feel skeptical of going all in on Substack Notes and replying to people and making connections that way, because I always feel like I’m part of the machine.
And so I really still prefer to make those connections in real life, in social spaces, because I don’t really want to be a part of the whole community-via-platform thing. When human connection is part of the profit model for a company, it starts to feel a little weird doing human connection the way that they want you to. Which is so sad, because human connection is kind of the best thing ever.
Traditional workplaces, of course, have a million problems, which is why they needed to unionize in the first place. But I have a ton of friends who are Substack writers, and we’re texting all the time being like, “I’m so annoyed about this feature, I’m so annoyed about this change, I hate the feed.” If we were in a traditional workplace, those conversations could be the start of a unionization conversation. They could be the start of a negotiation. And in this workplace, it feels like those conversations are stuck at blowing off steam, because we have no leverage and no classic model of organized capacity. Which sometimes I think is just unfortunately an evil side effect of the tech platform as medium.
Hamilton: Right – or an intentional side effect. In fact, those complaining conversations that you talk about were literally the seed of a lot of the media union drives that happened in the past ten years, including the one at Gawker. People bitching on IM about stuff turns directly into the union drive.
As you know, because we’re not employees of Substack, we cannot unionize in the traditional sense according to American labor laws. But we can definitely organize. And any type of organizing drive, one of the first steps is you go to everybody and ask: what are your issues? What do you want to change? What do you like? What do you dislike?
If you all imagine an organization of creators on Substack, what would your issues be? What would you want to negotiate? Katie?
Katie: I think I would probably be pushing for more investment in the podcasting side. It’s a newer part of Substack, and it’s very glitchy. We get complaints from listeners: they can’t listen in the app, they have to add the RSS feed elsewhere. That’s a little thing, but it’s our core business. I also think there are features that probably don’t have a direct path to monetization – this is my hunch – there are features that are built for people who have already handed over a credit card, like paid subscriber chat. It doesn’t seem as though there’s always a ton of incentive to work on those features anymore, because they’re not directly driving top-of-funnel business and conversion. But we have a very active paid subscriber chat, and to Substack’s credit, there actually has been some movement on that recently. Some improvements have been made. Those are the biggest ones for me personally. I realize they’re kind of niche. I’m curious, Rayne: what are your thoughts?
Rayne: I think I care about the stuff that a lot of other people care about, like a feeling of algorithmic transparency. And I would love it if workers could negotiate anything. I think it would be amazing for workers to negotiate a smaller cut taken out of our income. There are changes that would be amazing for the daily lives of writers, and I hope that we’re able to organize to achieve them. But I still feel cynical about the medium itself – this decentralized, tech, social-media-esque medium – being called the future of media. I’m just kind of anti-tech about it. I think perhaps the biggest problems I have, I don’t know if they can be truly solved through changes to the UI.
Katie: I’m also thinking about the venture model at play. There is so much investment expecting to see a return, and to see it quickly. And that incentive structure is antithetical to long-term planning, because you’re trying to make sure that your investors are seeing returns. I don’t really know very much about the Substack cap table or what’s really going on there. But if I had to guess – if I was a betting woman – I would say that the subscriber-only model on which the platform was formed and built and founded, of readers paying writers directly and the platform taking a cut – if we look at the way that literally every other venture-backed tech company has gone, you have to have advertising. That’s literally the only way, is to allow advertisers. And I think it’s kind of at this point that that is already starting.
I feel very ethically straightforward about how we run Diabolical Lies: you can pay us if you like it, and we’ll give some of it away, and whatever. I have some ethical qualms about advertising, but I obviously also do that, so I’m not saying that sponsorships are bad. It would be hypocritical of me to suggest that. However, I know a lot of people who built on this platform specifically because there wasn’t advertising. But as long as the incentive structure driving all of it is ROI, I don’t see a world in which that doesn’t eventually become a huge driving force of the platform, just by the numbers alone.
Rayne: A hundred percent, yeah, of course. And I think you can track a lot of the changes to Substack to that venture model of needing to make a concrete record of growth and expansion.
Hamilton: “Enshittification” is sort of what we’re talking about here. And it’s something that we’ve obviously seen play out in a lot of other websites, a lot of other social media platforms, a lot of other tech companies, a lot of other contexts. Do you have fears along those lines? When you look to the future of Substack as a company, are there things that scare you? Things you’re like, “these might be coming down the pike, and I wouldn’t like to see them”?
Katie: Well, yeah. As I said, every dollar that I earn as a creator is earned on this platform, whether it’s from listeners directly or from sponsors who are paying to sponsor something so readers will see it. So I feel a great deal of dependency in a way that I don’t love, just a sense of vulnerability.
It’s not that there aren’t other platforms doing the same thing, but with the wave of exits that we saw earlier this year and late last year, of creators leaving Substack to go to other platforms – and there are almost always financial incentives offered to make that initial move – I think all of these platforms have basically the same problems and are up against the same things. There’s a real sense that, yeah, there’s somewhere else you can go, but you’re always just going to be running away from one sinking ship to join another and then maybe coming back.
So there’s this feeling of impermanence, where I’ve just seen this film before when it comes to platforms and how they change and whose incentives and interests they’re ultimately responsive to. And I think it would be naive of me to assume that this is something that’s always going to work this way – unless something changes or unless those incentives and interests are in some way interrupted or challenged.
Rayne: Not to be so cynical that I discount the importance of acting on one’s values, I think that’s really important. But sometimes it feels like people are trying to find the last ethical big tech platform, like people are just jumping to find one that has good values or something. And I’m like, I don’t know if this model – even if it has a woker staff or something – I don’t know if it has legs in the long run for the values that I think we hold and that we would like to inject into our work.
Hamilton: For me, coming out of journalism and seeing the online media industry – I was there when it was the hot industry and all the money was going into it, and then I saw the money go out of it, too. All of that happened in less than ten years, so it was a really fast up and down. And when we were organizing in that industry, we were all trying to make the case that unions aren’t just to take care of the workers. It’s also that, if you want journalism to exist, this is a way to balance out the powers that be that do bad things and that have bigger social consequences.
I’m curious about how you think of those bigger social and political consequences in the context of this – I keep calling it the creator economy, but I don’t really know what the word is for what we’re all doing here, in this world where we’re all kind of atomized and self-employed. What is this doing to America?
Katie: Oh my god, that’s the million dollar question.
Rayne: I come from a union family. My family has a long, long history of union organization. My grandpa was a coal miner, he was a union steward. I grew up going to union rallies with my parents. I was like a union kid. My mom would always tell me: “our family history is labor history, our family history is union history.” I understand so deeply, and grew up understanding, that my family was alive because of the union. We were allowed to survive because of the union, and I feel very emotional talking about it. It’s a big deal to my mom, my family.
And I think so much all the time about how I am the person in my family’s history with the most comically overpowered capacities of self-expression ever. The amount that I can make my individual voice heard and be compensated for it is unprecedented in my family’s history. And I am the first person in four generations who has not been able to join a union.
I think it’s one representation of a much wider phenomenon that has been happening for decades. I brought up in my email [to the group organizing this event] the famous Walter Benjamin line: “fascism sees its salvation in giving the masses the ability to express themselves in lieu of granting them their rights.” That is the fundamental, endemic logic of the creator economy, the attention economy, surveillance capitalism, whatever you want to call it. You give all these people more power than ever before to say what they feel and to have their concerns platformed, and often you even give them an unprecedented opportunity to profit – or they’re promised that they might be able to profit – from the proliferation of their opinions. But it feels as though, also in an unprecedented way, the ability of that expression to affect meaningful change is rapidly decreasing. And the ways in which personal feeling and personal opinion can be leveraged into power is decreasing. This is obviously something that happens on Substack. It’s also the fundamental phenomenon of the last seventy years of labor history in the United States.
So I kind of forgot what the original question was.
Hamilton: How is the world being fucked up?
Rayne: Yeah, that’s basically my concern. I think that the ability to express yourself, while important, is often palliative or anesthetic. I feel very skeptical of an ecosystem that encourages people to express themselves and gives them decreasing material power to change their conditions. And that’s sort of how things are going, in my opinion.
Hamilton: That’s depressing. That’s why my essays haven’t changed the world.
Katie: Rayne speaks in complete poetic paragraphs. To be inside her brain! She just turned 25. It’s crazy. Also, Rayne, are you from Kentucky?
Rayne: I’m from Canada.
Katie: Canada, I didn’t know that! You said “coal” and I was like, oh, fellow Kentucky gal, maybe!
Rayne: Nova Scotia.
Katie: Oh, man, okay, yeah, that was an incredible answer. Cosign all of that. You just covered the paradox of having more ways to express yourself than ever, but less material power than ever really, really eloquently, so I won’t double down on that.
My mind, with this question, immediately goes to the content-agnostic incentives of these platforms. I worry about enshittification in general, not just on the platform side, but in what is being elevated and amplified. The incentive to do good work, to speak truth to power, to do things that are moving or that actually matter or that are well-researched – the more that this incentive model becomes entrenched, where the lowest-common-denominator stuff is going to pop off the most, the more that gets me depressed and cynical, because there’s really no countervailing force. I do think that there are plenty of writers who make a living on these platforms who are doing really good work, but it’s more the trend line that concerns me – the emphasis on things like Notes or short-form video.
When The Washington Post laid off all those journalists last year and everyone was talking about how all these journalists are going to go to Substack, I’m like — I don’t know. I have a really hard time with this idea that if you hand the keys of the castle over entirely to these sorts of incentive structures and venture capitalists, what happens to journalism overall? And we’re already living in that world to a large degree. That’s the fear that I have, long term. People will fight that tide for as long as they can, but ultimately if the material conditions continue to shift it’s going to be harder and harder.
I care a lot about journalists having the resources that they need to do good work. I mean, we talked about this on the Epstein episode that we did. I’m pretty sure it was The Tampa Bay Times that broke the Jeffrey Epstein story, and I don’t know if that paper even still exists. That’s not Substack’s fault, but it’s just another example of what happens when that ethos starts to dominate an industry like media. And you’re seeing consolidation on the traditional side too. So yeah, that’s my big concern.
Rayne: I’m a big believer in not looking backwards, but looking forwards. Sometimes in my head I can build up the heyday of digital media as this beautiful thing that we lost. And I always think it’s important to remember: well, this happened for a reason, and it wasn’t just a reason of big, bad evil people. The laws and systems failed people. I think I was one of the last people to get a full-time job as a writer at a magazine when I was nineteen, writing in digital media toward the very end of its existence, and I was freelancing. I remember that a huge part of why I started on Substack was because all of the places I was writing for were always saying, “No one will read anything over 750 words. It has to be about the most recent TikTok that went viral.” There were standards in place – that had been created by the systems of digital media – that were hostile to the type of work that I wanted to make and that a lot of people, I think, wanted to read. And that’s why I started on Substack: because there was stuff I wanted to write that I couldn’t place anywhere else, because nobody was paying for it and nobody wanted it. They believed it wouldn’t make money. So I think there’s hopefully a beautiful future that can be built. Because a positive that I’ll say about Substack is that it has proved there is a readership for idiosyncratic, long, strange, personal-driven work that maybe prior generations of media didn’t see a place for.
Hamilton: That’s a very good segue, because I do think we should wrap on maybe a forward-looking or upward-looking note. And you’re right that during the heyday of digital media, we all complained about how it sucked the whole time. But I do want to end on thinking about how things could be better.
There’s a question in the chat that says, “What would the ideal writing platform look like?” And I want to add to that with one more quote from the email that you sent before we started this, Rayne. You said, “If we think about the type of artistic landscape we’d like to see most, and the type of art we’d like to see incentivized and rewarded, what labor conditions could help engender that?” So we have about three or four minutes left. What’s the positive?
Rayne: Katie, take it away!
Katie: I was going to say, you take that one! The people want to hear what you think the ideal platform looks like. Also, shout out to C. Luft in the chat, who said, “It was Julie Brown at The Miami Herald who broke the Epstein story.” Thank you for that. We’ll give her her credit, give her her flowers.
Rayne: Chat, take it away!
Katie: That’s the point of organizing, so everyone can decide together what the perfect platform looks like.
Rayne: I literally asked that question in the email because I would love to know the answer. I would love for us to talk and figure it out. I think that ultimately I’m like: we need a different economic system top to bottom. Let’s do communism!
This is not actually a good answer at all, but something I think about a lot is that I really love, in the history of writing and the history of literary production, the role of the hobbyist. I love the person who – and I think so many great writers started this way – has a well-paying job that doesn’t take up too much of their time, and their rent isn’t too expensive, and they don’t have to work all the time, and so they can go home and write and they can make the stuff that they want to make. Stuff that maybe will never make money and maybe will never be a mass commercial product. I think that is such a beautiful idea, that we could live in a world where people could make art that matters to them.
And obviously that’s not the total answer, because I also think that people should be paid for their art, and I have a lot of other thoughts on that. But some of my favorite writing that I’ve found on Substack and otherwise is by people where Substack is not their job, so they don’t feel like they have to put out something every single week. Maybe they spend six months thinking about one thing and then they put something out and it’s amazing. A real problem is that right now, that position seems to be mostly occupied by people who have large amounts of family money, or who have married into money, and so are able to live a more leisurely life that allows them to produce artistically.
And thinking outside of tech platforms, I think a lot more people should have that position. To me, that would be one of the most amazing things for artistic production imaginable.
But in terms of what a perfect tech platform would look like – I’ll keep thinking on it.
Katie: So if we overthrow capitalism, then it’ll be perfect!
I don’t think I have the silver bullet answer on what the right platform would be. But I do think that all of us together would. And I don’t mean that in a trite way. I think collectively there is a wisdom here, in that enough of us are doing this every single day, getting up every single day, figuring out: what am I going to publish this week? Or how am I going to reverse this trend I’m seeing in my paid subscribers? Collectively, we probably could come up with some serious and realistic and practical changes that could make a really big difference.
One specific thing that has always been challenging for me is the pressure to constantly have something interesting to say. That’s a function of the platform and the way it is monetized – and it’s not just specific just to Substack, I want to be clear. It was an issue I had as a content creator at Morning Brew as well. It’s a very internalized capitalism structure of, you have to put something out every single week, and it has to come out at the exact same time. And I think that’s what really leads to burnout and sloppy work and mistakes and not feeling as connected to your work anymore, and just not feeling as good. The ability to say, “I’m only going to release something when I feel I really have something important to say” – oh my God, that is the dream.
Being on the content hamster wheel, you burn out quickly. And I’ve been doing this for about five years now, where every single week, sometimes multiple times a week, I’m like, “gotta fire up a take that’s gonna get the people going.” And it leads to shitty work. So in my panacea, in my utopia of a creator platform, we would find a way together to kind of surgically remove, or in some way undermine, that facet of monetizing creativity. Because I do think that it is to everybody’s detriment.
And I don’t think readers and listeners like it either. I subscribe to a bunch of stuff, and there are a lot of times I open that inbox and I’m like, “Ah, too much! I’m not even gonna go in.” I would love to receive fewer things. But that’s not what we’re incentivized to do. If we can somehow crack that, it would be one of the single biggest things that could improve our conditions and also the platform itself.
Rayne: So true. And thank you for giving a real answer instead of imagining an alternate economic system.
Hamilton: They were both very good answers. And I have to say, this whole conversation is such a good demonstration of why we’re having these conversations. I felt like a lot of wisdom came out, and just the fact of having these conversations is the value that’s going to push the ball forward.
This conversation was organized by a bunch of people, not just us. And we’re going to continue to have a series of these along the same lines, with different people talking. So please stay tuned. Join thesubclub.substack.com to stay in the loop about future conversations.
Thank you so much, Rayne and Katie, for being here. You’re both very smart. And thank you to the 800 people who watched this. Let’s all stay in touch and keep it going.
