Discontents Round Table: What's Happening to This Place?

The Discontents team is here to talk about the state of Online in general and Substack in particular.

Hey everybody, Derek Davison from Foreign Exchanges here. If you’re the kind of person who likes to stay on top of the latest happenings in the world of online media, or if you’re the kind of person who’s really into the comings and goings here at Substack … well, that’s a little weird to be honest, but we won’t tell anybody. Even if you’re not as Extremely Online as all that, though, you may have noticed lately that a number of people with prominent perches in The Discourse (no, not that Discourse) have brought their talents to Substack.

In recent weeks, Substack has welcomed Andrew Sullivan, who left New York Magazine so that he could get his calipers out of storage; Glenn Greenwald, who left The Intercept because he was either being censored or edited (accounts differ); and most recently Matt Yglesias, who left Vox because … to be honest I’m not entirely sure. Going back a bit further, Public Intellectual™ Yascha Mounk came to Substack to found Persuasion, the online magazine dedicated to ensuring that the mainstream center-to-center-right viewpoints that dominate pretty much every opinion outlet in the United States will not be silenced by, I don’t know, college socialists or something.

These acquisitions — and Substack’s “anybody can have a newsletter” business model notwithstanding, they are acquisitions — have substantially raised the profile of this place we call our work home, but they’ve also raised some questions. Substack already had its share of big names, to be fair, but have these new arrivals unbalanced the site? Is this still a place where anyone can start a newsletter and build a sustainable business, or is it now geared toward the marquee names? Has Substack become the default home for anyone who feels aggrieved by “cancel culture”? Is the site doing enough to cultivate diversity? In the first of what we’re hoping will be an irregular series, the folks behind Discontents are here to post through it.

We’re not actually sitting around a table, but if we were maybe it would look something like this (Saruntorn Chotchitima via Shutterstock.com)

So, everybody, what do we make of our new colleagues?

Luke O’Neil (Welcome to Hell World): Just to get this out of the way, I don’t think of us are suggesting that Substack should “censor” voices who dare to defy the Woke Orthodoxy or anything, but I think it’s undeniable that the platform is becoming known for a certain type of … let’s say personality. Add in the arrival of Dana Loesch — and while I don’t personally care much for all those names you mentioned she is orders of magnitude worse than any of them — and what does that say about Substack as a “brand”? Should we even care? I don’t know! Is it any different than sharing space on Twitter with the entire spectrum of sickos like we all normally do?

I wrote this early on when my newsletter sort of took off a bit and lots of people started asking me about Substack. I said much like podcasting there are going to be a handful of stars, a slightly larger “middle class” or what have you, and then thousands of people who give it a try and it doesn’t amount to a job. Which is fine. It needn’t be everyone’s main job. But I wonder if Substack is currently overemphasizing the stars, and if that is a problem unique to them, or if that’s Just How It Goes Everywhere?

Kelsey D. Atherton (Wars of Future Past): Something that spurred this, too, is Clio Chang’s excellent piece for Columbia Journalism Review on what Substack offers freelancers in a struggling economy. I found my experience pretty well reflected in Chang’s writing.

I came to Substack as, I imagine, many other writers did: my staff job turned into a furlough and then a layoff, I’d managed to pick up some other work in the meantime, but I wanted a little bit of cushion for when invoices were paid late. (Invoices are often paid later than the net-60 days that is somehow industry permitted). So far, that’s what I’ve found at Substack: a way to convert a modest-but-dedicated twitter following into grocery money, mainly by asking folk to toss in a few dollars to support a blog. I don’t expect this to supplant other income; I’m working two half-time writing gigs in addition, and some other freelance when I can find the time on top of that.

O’Neil: Yes and that aspect is great. I always tell people, look, if you can get 100 readers to pay you $5 a month, that’s great. That’s a good way toward a lot of people’s rent. That is a very achievable goal for a lot of people on here I think. And even if it’s just a space for you to do writing that makes you happy regardless of whether you make any money off of it, that’s a general good too.

Atherton: This all happens in the shadow of Substack suddenly building a name for itself as a home for high-profile writers who are at best established and bored, or want to ditch publications for other constraints, real or imagined. Some of those constraints are common to other publications, and entail the compromises of working with other people (having to support arguments with evidence, leaving the calipers at home, being told there are more important topics than student groups at Oberlin to worry about). Again, they loom large in the background; Chang’s piece is titled the “Substackeratti” for a reason, and their presence makes Discontents as an entity feel a little strange.

But I think Substack’s greater utility, if it can make it work, isn’t really as a publisher building a Parler-esque version of Medium. It’s creating a backup income stream for writers, of varying degrees, who are struggling. (That we’re turning to a tech company and its promise of neutrality to sustain work like this, after all tech has done to journalism writ large, is downstream from the power imbalance already at play.)

“To the extent that Substack fixes something in the journalism industry, it might be compared to GoFundMe—a survival mechanism whose resources are unevenly, arbitrarily distributed, laying bare systemic problems without directly tackling them,” Chang writes.

At least one of the writers Derek mentioned gave up a $490,000 annual salary to join Substack. They’re a marquee name, and if a following can sustain them at that level here I’m not particularly in a position to complain about it. But I worry that, with Substack’s internal metrics for writers and recruiting, that the company will at least act like a publisher in picking people already established as winners, and leaving the rest of us to try and write in their shadow, without the same support, and with greater need.

Davison: I think the danger of Substack becoming an outlet that’s dominated by a few big names manifests in a couple of different ways. One is that, if Substack is perceived as ten or a dozen superstars with a “rabble” of less prominent folks at the margins, then prospective readers may start to tie everyone at Substack to the baggage (positive and negative, I suppose) that comes with those superstars. That becomes easier for the audience to do if these major acquisitions are all of a piece, the “don’t edit me” crew or the “down with cancel culture” bunch. The whole site starts to take on some of the less appealing trappings of a single publication, even though it’s not. Its diversity of content and of perspectives risks getting muted.

O’Neil: Also, one thing I do agree on with a lot of the higher profile types who’ve joined of late is that editors are uniformly barbarians out to rob the world of joy.

Atherton:

O’Neil: I fucking quit.

Patrick Wyman (Perspectives): Writing on my own makes me so much more grateful for the editors I’ve worked with — my stuff is shit, please improve it, just hack it up and make it better — and I can’t imagine thinking that some mild oversight and criticism is CENSORSHIP. Then again, maybe that’s why I’m not making Glenn Greenwald Money.

Davison: The other, related issue is whether this is going to be a place that is responsive to the needs of all of its writers or one that’s focused mostly on high earners to the exclusion of the rest. Of course there’s an incentive to focus on the big ticket personalities, because their presence is an advertisement for Substack itself (“come write here, if it’s good enough for Andrew Sullivan it must be good enough for you”) and because they’re bringing in the most revenue. But they’re also the people who are least in need of support from Substack in trying to grow their platforms. For example, and this is a problem that predates Sullivan, Yglesias, et al, but for people coming to the main Substack.com page everything there is geared toward showing off the big dogs. There’s very little there that would help a potential reader find a more obscure newsletter that might interest them. It’s all about who’s making the most money, who has the biggest email list, and who’s generating the most buzz.

O’Neil: I agree that’s a problem, but for the sake of argument, is it any different than Twitter constantly recommending I follow five topics, three of which are Joe Rogan and two of which are Ben Shapiro? 

Davison: I do think there’s a difference between what the algorithms on Twitter (or YouTube, etc.) are recommending to people and the image that people independently develop of the site itself. I don’t think Substack is mature enough for us to know how that will work out yet. There have been internet newsletters around for a long time, but their rise as a form of mainstream media is a fairly new phenomenon and I worry there is a chance people will start to associate places like this with a certain “brand.”

O’Neil: It’s hard to tell being so immersed in it but I guess normal people probably do think of Twitter as the place where assholes go to say dumb shit in large part because of its most prominent users. I think on a personal level I also feel weird about it because lately Substack seems like it’s become a common joke, and it was this thing that seemed like it was going to be such a boon for all of us. Who cares I guess.

Eoin Higgins (The Flashpoint): Of course the counter to that is the people mocking Substack are mostly doing it on Twitter. It's not the public at large.

On the one hand, that doesn't matter too much — only a relatively small number of people in the country regularly use Twitter, and of those people an even smaller amount use it to discuss politics; one can then further narrow that down to those who are engrossed with the kind of news media we're all involved in making. On the other hand, it's safe to say that everyone in Discontents owes some portion of their career to social media in general and Twitter in particular, and that Twitter and Substack mutually reinforce each other within our little corner.

I do take the broader point, though, that the reputation of the publisher, or outlet, or whatever we're calling the platform eventually could have a detrimental effect on what a collective like ours is trying to achieve — namely the production of good, solid work that doesn't rely on claims of cancel culture or the like to get eyeballs.

Wyman: There are a couple of aspects here that come to mind: the practical, business-side aspects of Substack’s turn toward big-name writers; and the rather more personal side of it. To start with the second, at least for me — and I can’t speak to anybody else’s experience — there was something cool and validating in being valued by a platform, which is how Substack seemed to relate to its non-big-deal writers even six months ago. When you’ve spent years getting some combination of praise and being regularly told to go fuck yourself by people on the internet, it’s kind of cool to feel like you’re genuinely wanted someplace, a place that’s geared for what you need. That feels less like the case now, and it’s coloring my analysis. Again, that’s just my feeling, and I can’t project it onto anybody else.

Davison: I think I’m one of the old timers here — Substack hadn’t even rolled out its podcast feature when they pitched the site to me — and I can definitely attest to what Patrick is saying. Having felt like I was toiling in obscurity on Patreon it was really cool to have somebody asking me to come over to their platform. I’m not sure that feeling is available to anybody but big names now, which is I guess the way things go when a place like this expands but still feels unfortunate. It feels like something of the potential Substack exhibited back then has been lost, or at least has gone unrealized.

Wyman: As for the practical side, I’m sure for Substack it’s a lot easier from a logistical standpoint to make most of your money from big-name writers with large followings than from a fractious group of less-exalted folks. I get it. But if it ends up the same as podcasting, you’ll end up with a bunch of slick, approved products riding the top of the wave, a few exceptions that prove the rule, and then a vast series of struggling creative underclasses beneath them. For a moment it seemed like that might not be how it works here, and that felt cool, but alas.

O’Neil: Conan O’Brien substack.

Shane Ferro (Cruel and Usual): I come to this discussion from a very different place than most of you. I’m a lawyer with a journalism background who writes a very occasional newsletter because sometimes I feel like I have something to say. I have a Substack because I don’t want to go through the extra effort of pitching editors every time I have an idea, and I don’t have the mental or emotional space to write on a schedule. I similarly don’t have a paid tier to my newsletter because being able to take a few weeks off writing is worth more to me than I would make in subscription fees, which certainly would go directly to my therapist. BUT, there’s also value for me in how easy it is to flip the switch and create a paid tier on Substack. I could turn on subscriptions today with a couple of clicks if I lost my job or just wanted to open up that income stream. That to me makes it worth writing on Substack versus any of the other ways to self-publish content. BUT, I don’t really want my work being associated with Andrew Sullivan’s racism or whatever GG has going on. I don’t make them much money so I’m sure they don’t care, but I doubt I’m the only one, and I can see a future where people decide Substack is the longform Parler and no one cares what features they have to offer. Eventually, it could hurt them.

But because I don’t make money off my Substack, I feel more like an outsider than an insider. I’ve never had much interaction with the team, and I don’t really have a sense of what to expect from them, so my analysis is just coming from what I see as someone who loves gossip about money and media. It’s a weird company that I would agree is not really a publisher, but is also making some pretty deliberate editorial choices. Substack is paying writers to start up newsletters on their platform, subsidizing health insurance, and offering legal assistance if their writers get sued (for example). But not everyone gets these perks, and Substack is not upfront about who gets which resources and why. It seems like they’re spending a lot of money on bringing in big names that are guaranteed to bring in revenue from the start, but, as people have said above, there are no resources directed to incubating talent or helping readers figure out which lesser-read newsletters they might enjoy. If they’re giving resources to some people and not others, the company is taking editorial stances (money is speech, lol), and it makes it even more jarring that they don’t spend any effort trying to help lesser known writers get discovered. Presumably the narrative they want to push is that they are just a neutral platform on which to write, they are not a publisher who can make decisions on the content of what gets written, but that’s just not true. They’re recruiting writers and making choices about which voices get seen and which do not. I hope they recognize that enough to take it into consideration.

Gaby Del Valle (BORDER/LINES): I’ve always been a little bothered by Substack’s entire promotional model, which is that anyone can just launch a newsletter and eventually, with enough time and effort and unpaid labor, make a living off the newsletter alone. Like, sure, that’s possible if you already have some kind of following or platform elsewhere. It’s also possible if you’re one of the people getting resources from Substack. Of course, the people getting resources from Substack are the Big Names who don’t need the resources in the first place. It’s ultimately just replicating the media hierarchy that already existed.

That said, our newsletter is on Substack, and it’s grown fairly organically. But that’s only been possible because Felipe and I already had followings (smallish ones, sure, but still). There’s no easy way to find new, unknown people as a reader or reach new audiences as a writer. The platform doesn’t lend itself to that.

O’Neil: Substack has always been very supportive to me and I appreciate it very much but all the problems mentioned here are nonetheless valid. I should point out that they are highlighting some lesser known writers with interviews in the What To Read series and do have some programs for helping newer writers. I’m involved in one of them doing mentoring one on one, but in general the best advice you can give someone, outside of some best practices stuff and supportive encouragement, is: Be well known already. Not that easy to do!

Atherton: I can’t pretend to know Substack’s financials or business logic, but it seems like if they genuinely wanted to build it out as a platform for a range of writers (instead of a publisher that clearly favors certain kinds of voices), it seems like they would want to sponsor smaller writers. There’s a cost side to that, it’s probably cheaper to subsidize people who, again, aren’t leaving six-figure jobs to newsletter, but it’s also a way to highlight a whole swath of other voices, without having to do more than subsidize a salary. I keep going back to Chang’s CJR piece, but I was struck by how much good writing Substack could host if only it gave writers a working floor. I know my experience of online media, at least, is that writers tend to want to be doing the writing as much as possible, especially relative to, like, managing invoices or promotion or all the other business-side stuff, and if Substack has a five-year vision, it should include supporting a lot of writers with that now, on the off-chance they become bigger names in a few years.

Higgins: Having spent a large portion of my career as a freelancer/contract writer, I can attest to this. A platform like Substack, which combines the ease of word processing platforms like Medium with the fundraising of Patreon, allows for writers to focus on writing, publishing, and — crucially — not waiting to get paid.

Now having said that, I still do most of my work for publications and outlets with whom I already have a relationship. But I like that Substack allows me to write stories I believe in and get them up without having to fit them through someone else's editorial worldview and without having to worry that they're not newsy or important enough to be read.

Still, it's an approach which does put me in a bit of a different spot than some Substackers in that I'm using the platform as a repository for interesting stories rather than focusing on income generation. And Substack itself isn't reaching out to me to expand my reach, which is fine but it doesn't lead me to want to use it more than when the whim takes me. That is I think what Kelsey is getting at.

Atherton: To, ugh, put it in VC logic: right now Substack isn’t really actively making the small bets. It’s just trying to win over unicorns, who have already proven capable of doing great in writing online.

Davison: In fairness they have done a bit of this through their “Defender” program, which Shane mentioned above, offering potential legal support to writers who are in the program and find themselves in hot water. But much more “back of the house” support along those lines would be very welcome, I agree.

Kim Kelly (Be The Spark): I’m in a similar boat to Shane, in that I don’t update my newsletter all that often right now and certainly don’t make the bulk of my income off Substack (far from it — I think I make like $20 a month lol, though I was the recipient of a small Substack grant earlier in the pandemic) and so I often feel a bit like an outsider peeking in when we have these kinds of discussions. As a freelancer more generally, though, I have a lot of opinions about all this! The last thing I want is to see Substack, a platform that really does have so much potential as a tool for freelancers — who are already occupy the most unstable, unprotected rung of this tumultuous industry — either willfully or unwitting descend into a Parler-style refuge for disgraced right-wingers and outright fascists. Substack offers us a real benefit, and some people have found solid financial success using the platform, and it would be a terrible thing to see that opportunity evaporate to make room for more bankable reactionary shitheads. I’m already extremely uncomfortable seeing how much real estate the Andrew Sullivans and Gleen Greenwalds and Dana Loeschs occupy, and am very curious about how decisions over the allocation of resources is made; it’s obvious that the company is courting big names, but not everyone is being offered the same perks and sign-on bonuses, as it were, and there’s zero transparency over who is deemed worthy and who isn’t.

The company’s egalitarian mission seems to have been superseded by its own ambitions, and while things are not yet as dire as they could be, it certainly seems in grave danger of becoming a sort of holding pen for “cancel culture” rejects. As someone on the left who lost not only a freelance gig but a full-on staff position after Tucker Carlson threw a fit about me on his show last year, and was not then offered any kind of cushy landing pad by Substack or anyone else, it does seem a little strange that the lion’s share of the company’s attention seems to be focused on attracting a specific kind of voice — and not the kind that isn’t already well-represented in the pages of the Wall Street Journal … or Breitbart.

Connor Wroe Southard (A Lonely Impulse of Delight): It’s hard to add further insight given all the great points the rest of you have made. I guess my biggest gripe about Substack at the moment, as someone who isn’t yet monetizing but intends to do so fairly soon, is that most of us have to do ALL the promotional lifting ourselves. Discontents reflects an effort to help one another so we’re not all completely alone on our own islands, but we’re doing it without any formal support from Substack itself.

So the absolute minimum that Substack should do is to provide better support for people who don’t already have a massive platform. That would include making the platform as a whole more searchable — where do I go for an arts and culture newsletter, as opposed to a policy one? — and finding avenues to promote writers on social media. And I’m sure there are other things they could do that I haven’t even thought of. This should be the job of the company if it wants to attract and retain the best creators it can!

O’Neil: At the very least as a concession perhaps we could get the Who Writes On Substack graphic on the main page to show different writers every day or week? I love Sam Irby but it feels like it’s been the same six people for two years now!

Davison: One of the things we’ve talked about privately that also should be mentioned here I think is the lack of pretty basic tools for Substackers to analyze their own traffic. I don’t want to get too inside baseball but the upshot is that the Substack backdoor makes it next to impossible to figure out why, for example, you’re getting a lot of new sign-ups in a given day, or if anything in particular is driving people to your newsletter. It’s frustrating and again seems geared toward a site that caters to people like Andrew Sullivan, who gets traffic because he’s Andrew Sullivan, Public Intellectual™, and never really needs to drill much deeper than that. If that’s not what Substack wants to be then this is another area, like business support, marketing, and incubation, where it needs to invest some resources.

O’Neil: And we’re already seeing some would-be competitors starting to crop up.

Atherton: To exist as a writer online is to contend with a range of sub-par mechanisms for turning writing and reporting into income, and Substack is already in, er, crowded space with other crowdfunding tools people can use. As it is, Substack provides a decent mechanism for writers with an existing platform to convert that established audience into some amount of money. But I don’t think people get into tech startups just to shuffle around which big name writers write from where.

If this is going to be a platform that can grow in a way venture capital demands, then it has to put the money and the effort into more than just poaching writers who could get a big salary and an audience anywhere. There’s freedom in being a platform, and if the bets it makes in terms of funding writers are spread broadly enough, then Substack can plausibly argue it is more than just a publisher feigning a lack of editorial direction. It needs to put in that effort, though.


Hi, it’s Derek again. Clearly this is something we’ve all been thinking about quite a bit, and there’s a lot to digest and I’m sure more discussion to follow. To borrow a phrase, maybe some people see Substack as it is, and ask why. We dream of the Substack that never was, and ask why not. The model of paying writers and podcasters directly isn’t perfect and the market is probably already in danger of becoming saturated, but sites like Substack still provide an opportunity for perspectives that can’t break through in traditional media (especially under its current, highly corporatized model) to establish an audience and find their voice, so to speak.

I think the frustration we’re expressing here is borne out of seeing that potential lost in the urge to cater to headliners who have already broken through in traditional media, but for one reason or another decided to leave it anyway. It’s not that we want Substack to reject those folks, but we would prefer it not fall into the trap of pampering them to the exclusion of those who are still building a platform. One of the reasons we started Discontents was to support writers who are still building their platforms. We’re hoping to do more of that in 2021, with new voices and more original content like this. Thanks for supporting us and please continue to help us spread the word and grow this newsletter!

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