Substack CEO Chris Best wants to fix the viral internet

"Twitter didn't invent the urge to dunk. They did build like a giant dunking amplifier."

Welcome to Extra Garbage Day! These Thursday issues are typically paywalled, but I’m sending this week’s out to all readers. If you like this sort of thing, hit the subscribe button below. Next week’s Extra Garbage Day is a conversation with Glass Beach, one of most exciting bands right now in the new very online world of emo and pop punk.


If you’ve been reading Garbage Day for a while, you know I write about content moderation a lot. I subscribe to the theory that everything online, and, more recently offline, is essentially just message board drama.

I believe that much of the work that needs to be done to make a better, safer internet happens not by extremist whack-a-mole (though I don’t mind it) but with healthy incentive structures, algorithmic transparency, good UX design, and strong anti-harassment tools. And because tech journalists these days are constantly told they’re just being negative for negativity’s sake, I like to try and highlight platforms that seem interested in improving their moderation — Pinterest, Twitch, and Discord — as often as I rail against sites that I think suck at it — Twitter, Facebook, and Clubhouse.

Substack is a weird site to include in the moderation discussion. I’ve written about it before and I’ve argued that it might need some clearer anti-harassment guidelines in place for when the high-profile bloggers migrating over to the site do what bloggers do best: cause unfathomable amounts of internet drama. But because Substack is not exactly a platform, as we typically think of them now, a lot of the usual online community philosophies don’t totally line up.

Substack has leaderboards for different topics, a community spotlight program via a newsletter, open comment threads, and the controversial Substack Pro program, where the company gives writers a money advance to join. To be clear, I am not affiliated with that, nor was I offered it. Beyond that, Substack is basically just a text editor, an RSS feed, a Stripe integration, and an email management service. Its analytics don’t even track inter-Substack mentions. If you flame me in your newsletter I simply do not see it. Posts have comment sections, but they can be turned off or, even better, paywalled for subscribers only. And you can toggle those features at anytime.

There are plenty of writers I don’t like on Substack and ones I’ve even gotten in fights with — I’m a blogger after all, I, too, attract drama. I have, so far, come across one high-profile newsletter that I truly think is genuinely dangerous. But in the last year of using the site as a full time job, I have not experienced even a fraction of the amount of harassment and abuse that I regularly experience on Twitter or in the Facebook comment sections of stories I’ve written for big publications.

Substack has reputation as the WWE of online publishing, and while the site’s writers are definitely fighting with each other, most of that is still happening on Twitter. It’s also important to mention here that I’m a white man, which absolutely plays a role in insulating me from the more vicious abuse that is typically experienced by women and people of color who publish content on the internet. But for the most part, my last year in newsletter land has been quiet and nice, with most trolls still piling on via Twitter and leaving my inbox hate-free.

This is what Substack CEO Chris Best in our interview described as the “friction” inherent to email publishing. Is someone really going to sign up for your newsletter, wait for you to publish a post, and then reply to it to tell you how much they hate you? Maybe! The internet is full of maniacs, but it seems unlikely.

Best and I also spoke at length about incentive structures. I learned that his bet on subscriptions as the core monetization feature for Substack wasn’t just about getting writers a nice monthly Stripe payment, but, also, a way, he believes, to make sure that writers aren’t tap-dancing for clicks.

My main goal with our interview was to better understand how Substack sees itself. Considering how much existential hand-wringing people are doing right now about The State of Newsletters, I wanted to answer a few questions I have after a year of full-time email, namely: where the heck is this all going? And if Substack is really the path forward for online publishing, how does a world of a million individual voices, sometimes with the audience reach and financial capital of traditional publishers, not spin out into craziness?

The following has been edited for pacing and clarity.


Garbage Day: I want to start with the announcement this week about Substack acquiring Letter. I would love to hear how you see Substack. What do you, fundamentally, think Substack is? In terms of what you're acquiring and what you're building — what is the full picture of Substack, as you see it?

Chris Best: I'll give my spiel because you're asking the question that presses the “give Chris’s spiel button”. So I apologize in advance. The reason we started the company is because we think that what you read matters. It shapes how you think, how you see the world, who you are. Internet culture is just culture. It's not a wild, novel idea. But the basic idea is that it's valuable, right? This stuff is the source of a lot of human meaning. Great writing is valuable because it has the power to change who you are.

And so the state of how we fund, create, and incentivize culture on the internet is actually really important. And we should be doing a lot more. I kind of think phase one of the internet was: Make distribution global and incident free. And you had this wild profusion of creativity, but we never really figured out how to make money off of it in a way that's sustainable. And we've kind of, over time, drifted into some bad incentive traps. The things that you end up with, because of how these things played out — the idea that everything has to be free — we have to have these giant feeds that are trying to pump us for as much engagement as possible.

The incentive structure you create pulls towards bad stuff over time. Bad as individuals because your feeds are positioned against you in some way because they want you to do more of their thing, which is not necessarily what you want. And kind of bad for the broader culture and society because you create these evolutionary landscapes for memes that evolve into the worst kind of thing.

The race to the bottom culture.

Yeah, the race to the bottom. And that's not a law of nature. That's an emergent effect of the systems that we've designed in “v1 internet”. And I think you can look at a lot of internet history through this lens of, “what is the characteristic of each platform?” What are the incentives that were created and what did that turn into over time? And they're sort of hilarious. Anybody that's a heavy Tumblr user, you ask them, “what is Tumblr like?” And they're like, “well, there's a rabid community of something and then there's a smaller, but even more rabid community of anti-that for every possible something.” You know, that's how Tumblr is. That’s a property of how the system works.

I did a messenger before this and I got this appreciation for the fact you can't change human nature. But the rules that govern the digital spaces we inhabit have a massive effect on our lives. And so making them better could have a massive positive effect. This is why we started Substack in the first place. What if there were different laws of physics for internet culture? Where instead of trying to feed the engagement beast for never-ending growth, you could make something thoughtful and consider that people would sort of have a higher friction, but higher commitment way to pay for it, both with their attention — when you sign up for an email newsletter, you're not clicking on a recommended video, you're making a decision to trust someone a little bit, right? And even more so, of course, if you pay, you're saying, “hey, this is worth chipping in five bucks a month, 10 bucks a month.”

So, you read Garbage Day, you know that over the last six months, I’ve looked at the moderation stuff on Substack. And speaking of incentive structures, I do think even I had this reaction at the beginning of like, “okay, here come all the hotheads from Twitter.” But six months later, it doesn’t feels like the amount of drama on the site that I think people assumed was going to happen happened.

I don't want to over-claim here. I don't think that everything’s perfect and there shall never be internet drama here because I think drama comes with human nature and human issues. I actually think the real question here is: What does every other platform do to maximize the drama? Because I feel like on large swathes of the rest of the internet, we've converged into machines that are designed to always make us have the stupidest possible version of every argument.

Twitter is an example of this. I think the way that replies work and the way that quote retweets work and the way that people look at Twitter overall, the way that people think of trending topics, the mechanics of it, the small details. The fact that when I when I retweet something with a quote, I'm promoting my reply to that thing to be a top-level item. I'm, by default, doing it performatively. I'm talking to the world about this asshole. It’s the way that mechanism works.

Dunking culture.

Twitter didn't invent the urge to dunk. They did build like a giant dunking amplifier. They kind of made that a thing. And you get into a place where if a really good dunk exists — it's almost like in economic terms, like $100 bill on the floor, even if you're virtuous and you're like, “I'm not going to do that great dunk…”

You got to do it.

Someone else slightly more evil than us is going to do it, right? This is something that's actually quite interesting. If you if you design the rules of a system poorly, you can end up with a system everybody kind of hates and wishes was better, but then no one can change. And the fact that you have a lot of users on Twitter who describe it as the “the hell site” and what they do there as “doomscrolling,” like people are living in a self-made prison in a weird way.

I think a lot of [Substack’s incentives are] actually not necessarily some genius thing we've done. It's like, “hey, how can we just at least not create horrible incentives to begin with?” If I have to thoughtfully sign up for your newsletter and then if I come and give you my email and you send me an email, that's kind of good — and especially the payment. I like to say that people will hate-read things, but they won't hate-pay for them. Which is mostly true. And even if they do pay for them. Maybe they don't mind too much.

I mean, at that point, you’re a paypig. You're paying for it and you hate it. That's your fault.

Yeah, exactly. Whereas, if you're like, “one more scroll,” and you hate it, you're like, “oh, well, you got me again internet.”

So another thing over this last year that's become really noticeable, which I think is making people confused, if not freaked out, is the rise of the individual voice. It’s like brands wanted to be people. And then people wanted to be brands. And then it feels like the whole thing blew up. And now we just have people who are the same as brands. How do you see that business structure continuing? Because I think a lot of people right now are asking themselves, “okay, if I'm just an island of one, and I have a Substack that pays me whatever money a year, and that's my job, what happens then?” Where does all that go?

That's a really interesting question. I don't feel like I have a buttoned-up answer to it. Something very early on — when we first started Substack — there was this fork in the road, right at the very beginning: Are there newsletter publications and users? Or are there just users? Like on Twitter, there's just a person, there's just an account. And I think YouTube actually used to have a differentiation between channels and users and then after a great pain and awkwardness, they smashed it back into one thing.

[With Substack] you can make a brand that's outside of your individual person. But I do think that people are hungry for… “authenticity” is such a cheesy term, but there's the venue for someone they can trust that has some perspective that's not kind of bogus in some way.

It's like they're hungry for a voice that feels like they're being talked to by a person that isn't a committee, I guess, maybe.

Yeah, the person that isn’t a committee, that might sometimes say what they think, but isn't necessarily telling me what I want to hear. That isn't necessarily telling me what's going to drive the most traffic. That isn't optimizing each individual piece of content to feed the machine. Like, here's a human perspective on something. I think that really matters. And I think if you design an institution well, you can allow for human perspective within it. But I think that's what people are really hungry for.

And how does that idea work with podcasts? Because I feel like they're similar, but then, also, as someone who's done both, they diverge in wild, different ways. So I'm sort of curious how that structure builds out for podcasts?

I'd love to hear more about how you think about that actually. There's a fundamental similarity between a newsletter and a podcast. Just like how many people use it, right? Signing up for your newsletter and signing up for your podcast are both a high-friction decision to invite you into my life, in my mind, over a period of time. And there's a difference in how you make it and there's a difference in a bunch of things, but that kind of thing is the same. And I think the model, the Substack model, which is basically, “sign up, give you an internet thing, and then pay for the thing if you like,” helps make the thing better and works really well for both.

We did a very basic podcasting feature because writers were asking us for it. And we started to see a bunch of podcasters be successful on subjects and have writers who want to have a podcast and podcasters who want to write and having the two together in one place that ties through email is just a really compelling mix of stuff.

What do you think is the main difference? Like what do you do think is the wild divergence?

I would say it's maybe in growth and perhaps in output. A podcast requires a little bit more production. But, in my mind, there really hasn't been a good way to capture podcast listeners. That's why you get podcast Discords, subreddits, or email lists, which don't usually integrate with the audio tools needed to actually hear the episode. It just seems like no one has really figured out a way to capture an audience for audio.

Well, I think Substack can kind of be that, right? Since it already has, I mean, “followers” and email lists that you, as the writer and podcaster, own — which is great. There's something you said that I was gonna respond to:

The thing about podcasts is that it’s hard to grow a podcast because a podcast episode is fundamentally unsharable. It's like if someone in your family sends you an hour long podcast, like, “you got to check this out,” you're like, “man, you're going to have to sell me really hard.”

[Ed. note: My dad does this at least once a week. They’re always about crypto and none of them have ever been under an hour long.]

Subscribing to newsletters, subscribing to podcasts, is kind of like investing your trust in someone. You kind of need some way to follow up with them before you're willing to do that, which is why being guests on other people's podcasts and having other ways to drive people to it is so important. And I think all this stuff could work really well together.

So I've been surveying the “digital tip jar” stuff and I was curious what your feelings were on subscriptions versus micro-payments, because it does feel like a lot of people are waiting for the bottom to fall out of subscriptions. There’s almost a weird feeling of glee on certain parts of the internet at the idea that people will stop paying to subscribe to creators. What do you see as the road forward for that? Will it evolve into people paying $1 one time to read something? Or are they going to keep paying $5 a month?

I mean, I built the whole company out of the idea that the subscription is like — it's called “Substack”. The “sub” is subscriptions. It's a strong hypothesis here.

I thought about this because we were first talking about like, “okay, you need a different model, people should pay for things that's going to make better laws of physics for the internet, blah, blah. What's the best way to do that?”

We looked at micro-payments. I think micro-payments fundamentally don't work because they're annoying. And maybe the fancy way to say this is, every time you pay for something, there's kind of two types of pain. One is, “oh, man, this is a lot of money and I wish I could have that money to spend on something else.” And the other is, “I have to decide to do this.” It can just be a hassle to actually pay.

With micro-payments, I think one of two things happens. Either you keep that decision pain pretty high. And it's like, “do you want to pay for this article?” How are you going to decide that? It's annoying and that the amount of decision pain dwarfs the amount of economic pain and so you're not making as much money as you could.

Or you end up doing the thing where you're like, “well, it’s a micro-payment, but you’re not actually going to have to decide to pay. We're actually going to automatically hook up your micro-payment to a distributor.” And then you do “claps” or you do something and it turns into payments. And then what you've done is you've just recreated the bad incentives.

Like what Medium has, right? Where every time you write a post, you're like, “oh, god, I hope they clap at this,” right? It's kind of defeats the purpose.

On interesting. A lot of far-right bad actors weaponize micropayments, to support harassing people in real life or other kinds of viral stunts. And I had never thought about whether or not subscriptions might cut down on that.

It's a commitment, right? I have to think about whether I actually want to trust you and it's harder to get a subscription. Once you have it, it's way more valuable. Because you kind of have a set of people that are like, “hey, I've decided to like trust you for a bit.” And it gives you the space. You can write an issue of your newsletter, like, “I'm going to tell my readers something they might not totally want to hear and they're still going to get it.” Whereas if every time you're writing, you have to please the micro-payment distributor algorithm, you can't have that trust and therefore you can't have that authenticity that people crave so much.

In terms of that “buffer” and giving people that space, there's been a few newsletter writers in the last month who have said, “the schedule I was on was too much” or “I'm going to slow down.” And there have been whispers among some newsletter writers I've talked to (👀) who are like, “what's happening? Are people going to burnout? How do we continue this?” How does the longevity of this kind of thing work?

I kind of joke that Substack was created because I started writing a post about what it should be and then I started procrastinating by making the company and never finished the post. So I'm not one to lecture anyone on like, “here's how you should post all the time.”

I think one thing that we try to encourage writers to do is set a reasonable schedule for yourself and take breaks. Your subscribers don't want you to work 365 days a year and burn yourself out and not be able to do it anymore. If you want to take a couple weeks off and live your life, they'll understand that you can set that expectation up front.

But I do think that having the motor to do one of these things regularly is not something that everyone has. It's tough. Even if you're just saying, “hey, I'm going to do this a couple times a week and take adequate vacations.” That's a lot. I think there's a real tension there. I think it’s about finding the right balance and setting norms where it's like, “hey, it's the expectation that people who do these things still take breaks.”

I would love to hear about some hidden gems on the platform that people might not know about. One weird thing about Substack is that there are some recommendation features, but there aren't a ton. Which means I'm constantly learning about newsletters that I had never heard of before and passing them around. So I'd love to hear about some of your favorite smaller ones.

My go-to one that I use to try to explain to people the breadth of things that are possible on Substack is one called Popping Tins, which is reviews of canned seafood.

Oh, man, I love canned fish. That's amazing.

One of my long-time favorites has been Flow State which is just a daily curated playlist of music to work to.

My dad sent me one yesterday that was an engineering one. It was called Construction Physics.

I put it in the company Slack and people were like, “have you seen this chemistry one?”

Then somebody counter-recommended The Polymerist.

It’s like [one those kinds of newsletters] where people that are in an industry know a lot about it and if you want to know what it is, for some reason, it’s just really good and interesting.

It all feels very bloggy — which, okay, so there's a punchline a lot, where it's like, “oh, newsletters are just blogs again…”

People say, “oh, newsletters are just blogs again,” and I'm like, “fucking great. Yeah, that's awesome.” The only problem with blogs is there's no way to make money and mobile killed them.

I was actually talking to a friend yesterday about the loss of the Good Post. The post that derails your day. Where you're like, “oh, I have to send this to 10 people because it’s so good.” I want that culture back. In my 20s, that's all I wanted to do. Make a good post. Here's a final question: Is there anything that's not happening yet Substack? Where you're like, “I'm waiting for someone to do this,” and no one has done it yet.

I will never say that anything's not happening on Substack. I don't have a universal view of it.

One thing that I think that there's tremendous opportunity for on Substack — and that people are starting to play with — is fiction. Serialized fiction. And there are some good examples of people starting to experiment with it, but I think that I see no reason why that couldn't be really big. You know, if you look at just like the fanfic communities, but even there's just like a whole world of serialized stuff that has a long historical precedent like Dickens serialized novels back in the day. I would love to see more. More fiction on Substack.


If you’ve been forwarded this email, welcome! You can check out a full list of the previous Extra Garbage Days here. And here’s a short list of who I’ve interviewed recently:

And, lastly, here are five Substacks I like that you may not know about:

  • Fingers by Dave Infante. It’s about alcohol and the culture of drinking.

  • Technically by Justin Gage. It’s about the most technical parts of the internet and how they work.

  • The Trend Report by Kyle Raymond Fitzpatrick. It’s everything you need to know about the current zeitgeist all in one place.

  • The Daily Respite by Clara Parkes. It’s just really nice stuff!

  • Proximities by Barry Malone. A great digest of international news stories.

***Typos in this email aren’t on purpose, but sometimes they happen***