Chris Best

I've always believed that the things you read and the media you consume in general is not just how you spend a big chunk of your life. It changes you. And so great writing and great culture in general is this deeply valuable thing. And so now I was like, I should write. How hard could it be? I would love that. I have ideas. I know how to type. Like I'm a programmer. I love reading. And I started writing what I thought was going to be an essay or a blog post or a screed of some sort, like detailing my frustrations with the media economy on the internet. Kind of just complaining in broadstrokes. Look, the internet came along, smashed a lot of the business models that used to sustain culture and hasn't really—I mean, it's created a lot of wonderful things. There's been a lot of promise, but it hasn't yet replaced especially like the economic engines that made those things go in, you know, in a way that was satisfactory to me.

And I was just kind of whining. I was going off and saying, you know, sure Craigslist killed the classifieds and you know maybe Facebook is not an unalloyed good. And I sent it to my friend Hamish who's actually a writer and he let me down very gently. He's like, these are all good points you make but it's 2017 and you are not quite as original as you think you are. Like other people may have noticed that some of these trends are going on, but he's like, here's how you could make this essay you're writing better is you should add a section that just says so what do you do about it? How could this be different? It's easy to complain. It's easy to say here's everything that's wrong. It's much more interesting though. It would be more interesting as a reader to have a theory of what could a new and better thing be. And we started arguing basically and that argument turned into what became the core idea for Substack.

The core idea is that the writers and the people who make the culture are the heroes and they need independence in order to give the thing they have to give to the world. They need the freedom to make the things they want to make. And they need to be able to make money and not just make money incidentally, but to be able to make money doing the work they believe in. And that if you can create those conditions, not only will it appeal to the best writers, the best makers, the things that will get created will be different and better.

Yeah, we were arguing about the thing. I've always felt that if you sort of need two things to have a really worthwhile idea in technology. You need to have sort of what I think of as the science fiction vision, a sort of a grand important idea for how the world could be different that actually matters. And you need to have sort of a humble beginning. You need to have like a first step that you can actually take soon to be able to make progress towards that thing. You don't have to know how it connects. I don't think you can have this kind of foggy city on the hill and then you can have this next thing that you do. You have to have some belief that you're going in the right direction, but you don't have to know where the rest of the path lives. And as we were arguing, we sort of realized, you know, we were developing this grand science fiction vision, this idea that you could make a new economic engine for culture. I mean that ultimately to me it's like I think you could power a renaissance. Not as in we would be the ones to do it, but by giving kind of like the tools that the creative class need, you could actually create something that really meaningfully changed the world. And we had this very simple place to get started, which was this idea of a paid email newsletter. And there was already people that were doing this in the world. There was this guy Ben Thompson who wrote a thing called Stratechery that was like a tech business newsletter. You know, he was writing this thing from his bedroom in Taiwan making millions of dollars a year sending out this email that people paid for. And we looked at that and we were like, hey, that's something new and better is getting made and is successful. Successful in that it makes some money, but also successful in that it's making something that people really value. And it works today for this person and there's no reason it shouldn't work for some more people and it is actually a viable kernel of this much larger thing.

Yeah. The thing that really appealed to me then it was around independence. It was around the idea that you know in the early days it was really writers because that was sort of that initial you know Hamish was a writer I'd been trying to write it was this writer focused thing. I don't think the idea is actually not only for writers but I felt that the people who were the most interesting to read had this kind of like outsider nerd thing. And if you could free them to pursue their obsession or pursue their vision to the utmost, it would allow the creation of new culture. And in order to free them, you had to give them a business model that actually worked for them. You had to have a strong presumption of freedom of the press, but also you had to like make it simple enough for a person to actually use. And you know, one way to look at Substack early on was like, hey, come and type into this box. And if the things you type are actually great, which is really hard by the way, almost nobody can do it. But if you can do that one thing, if you can type something great, you know, to put it reductively, we will make the rest magically work for you.

You will get rich and famous if you can type this thing that's great, which is hard enough.

Yeah, I would say so. At least in the sense that really good new ideas are always countercultural or there was—it always starts as the counterculture.

I mean, the things that were not countercultural weren't as ill-served. Like, there was lots of outlets for the main culture, I suppose.

Yeah. And that part was not an exciting blog post to write, but it sort of triggered—I saw that as but we could make this tomorrow. There's something we could do here that would work and it would be the first step towards this bigger thing we feel we're seeing.

We had it narrowed down to two names. We had lots of ideas.

It was either going to be Substack or Monograph.

Both respectable.

And how did you choose?

The very first piece that was physically posted was sort of a manifesto that Hamish and I wrote. You know, once we decided to make the company, we kind of got to work. I started building the website that was going to hold the thing and he started writing kind of an original vision for the thing and I felt we couldn't publish it somewhere else like we had to use our own software to publish the first piece. So that was the first thing that was ever published at all. And then the first Substack launch was this guy Bill Bishop who had been writing an email newsletter about China for kind of a business and government audience.

Well, he read the manifesto. I think Hamish had known him for a while. Often this is the thing you want when you're making a new product. It's like you don't want it to be kind of good for a lot of people. You want it to be really good for like one person.

And he was that guy. He had been already writing an email newsletter. He already had this audience of dedicated business and government people that loved it and had a ton of value in it. He'd been thinking about charging for it, but he couldn't, you know, didn't want to mess around with all of the technical details of doing it. So, when we went to him and said, 'Hey, can we just make that happen for you?' He's like, 'That sounds great.'

I would say there's lots of people who have been to my mind copying the output who are looking say oh like it's email newsletter publishing so send an email and charge money like we can copy that and for cheaper. And then we've had a couple of iterations of you know the old Twitter bought a competitor that was like that and then tried to build the feature into and then after Elon bought it they tried to build the feature into X. Facebook spun up a clone for a while called Bulletin and sort of tried to like cargo cult it from my perspective. I mean, I'm biased, but there's nobody to me that seems to be doing the exact same thing we're trying to do. The thing that I set my sights on in the world right now is just YouTube because YouTube of the major networks is the closest to being an economic engine for culture. It actually does pay people. It has an opinion about how that should work and it is just completely enormous and dominant and is in some ways so good and then I think in other ways it falls short.

Yeah, it's just okay. I'm curious if this resonates for you, but I've heard people who are sometimes very successful people on YouTube who say, 'I have an idea for a thing I would like to make. I know it will be great and I know there's an audience who would love it, but I can't distribute it.' Like, it won't work on YouTube because the algorithm won't like it.

And I think that's too bad because it sort of limits your ability to take a creative risk, I think.

The reason I think email was one of two things that we could have used at the time because the basic theory behind it was the thing you want out of Substack as a creator is a direct connection to your audience. When people subscribe to you, the social contract of that is saying, 'Hey, I'm putting enough trust in you that I'm giving you the right to come reach out and tap me on the shoulder.' And that's the thing that allows you to, you know, take a creative risk and presume upon that and say, 'Hey, this might not have found you otherwise, but because you have subscribed to me, I'm going to presume upon that and send you this.' So, the direct connection was the key thing we wanted to enable. And then we were living in a sort of a smartphone age where my view is there's like a limited number of rectangles on your home screen that you have. And most people have like three to seven that they actually go to. And in order to really have the connection to the place where people are consuming things, you have to be in one of those rectangles.

And most of the rectangles were not just powered by algorithms, but they were powered by algorithms that were actively hostile to the idea of having a direct connection. Right? Facebook does not want to give you a direct connection to your audience. Neither does Twitter and neither does, you know, even YouTube doesn't really.

Their business model is different than that. And so if we wanted to give people the power of having a direct connection, you know, in the long run, we could make our own app, which we've since done, but at the time it was basically, okay, which of these existing apps can you actually have a direct connection with people that people actually already use and do? And I think the only two were email and the podcast app. And email has this very nice property of being transferable. So if you had an existing email list, you could bring it to Substack. Also, part of the promise, and this was key right from the beginning, was you can leave. And so, we want to make this thing great. We want to serve you really well. We want to give you enough value that you want to stay here. But part of the reason you can trust us is because there's exit rights. You can go and you can bring your audience with you. And email is sort of like a wonderful—there's a lot of fancy ideas of protocols that would let you do this but email is the one that actually works in practice.

I think that actually helped at the time because you're obligated to check it. So you actually do check it, but then when you're checking it, when there's 10 things that you have to deal with and one really great piece from a writer you love, you're like, 'Well, I have time to read this.'

We had the web stuff right from the start. And so even from the beginning, it wasn't—you could think of it as a paid email newsletter, but a key part of it working was there's a web version. And so the way that it would work is people would share the web version, right? But they would once they subscribe, they would stick around and have the direct connection and email. And so pretty quickly, you know, we built the ability for anybody to sign up. We built the ability to do free ones as well as paid ones. And then I think probably within a year or two, we got to podcasting features and we started to build other pieces.

This maybe gets to the business model question because the thing that in our minds differentiates Substack is that it is a different fundamental business model both for the people on the platform and for us, right? So the way that Substack works is you can choose to charge a subscription. Once you charge a subscription, you can still publish stuff for free or you can publish only to your paid audience. And the only way we make money is by taking a percentage. And so we literally can't make money without the people on the platform succeeding. And we felt like that and still feel like that is sort of like the core.

Yeah. Like you make no other way. Nine times more money than we do. That's just how it works.

And that means that as a—we just have a different set of incentives as a platform. We want to encourage people to not just doom scroll and spend their time on it, but to connect with things they actually love enough they might want to pay for. But very early on we took that with too much of a religious fervor and we said we're actually only going to allow paid stuff. If you want to start on Substack, you have to charge. And we're not even going to let you send an email to someone for free because that would violate the sanctity of our beautiful idea that we've created. And immediately we realized that was never going to work.

Because the first customer said, 'Okay, well, where am I going to send the free ones?' And we said, 'Well, it can't be in us.' He said, 'Well, I have to do it because it's how the business works, so I'll do it somewhere else.' And so we kind of we got pulled along by the people who were doing it. It's like oh it like actually the you know the free part is a very important part of the business even for people who are focused on paid you know you have to have a web version you have to have these other features. We found the percentage that you can expect varies quite widely in those early days we often saw kind of like five to 10% of people converting depending on sort of where your audience was coming from and what sort of pre-existing relationship they had with you sometimes be much higher but it was maybe the common theme was it is often much higher than people had expected. And I would say even to this day, people probably slightly overrate the ads business that they could have and then they dramatically underrate the subscription business they could have.

So the traditional press, the business model was already kind of like feeling this pinch where the internet changes had swept through. It was sort of in this structural decline. And then for me as a reader, what I felt was there was sort of like a narrowing of perspective and a narrowing of thought where a lot of the things you would read were very predictable and came from the same place and I felt like that was unsustainable and you couldn't sort of sustain maintain a healthy intellectual culture that way.

Yeah, it's been a time of immense change. I mean, we sort of went through a period, I would say around 2020 where some of those forces kind of came to a head and there were a bunch of instances where the people who I felt were the most interesting people were often sort of defenestrated from their traditional—thrown out, pushed out, like fired, chased out by mobs of people who disagreed with some element of what they were saying.

Corporate interests or there was sort of like a maybe the way I would put it is like the narrowing of allowable perspectives reached a fever pitch and jettisoned a lot of the original thinkers. Like the people who were least likely to go along to get along were the most likely to get—and probably the most interesting people to read as you said. And a lot of them would start a Substack and instantly make huge amounts of money. I mean I had this conversation I'd have with people I'd you know or I'd say hey you should consider starting a Substack. You'd make more money. You could have these interesting things. And they'd say, 'Well, sure. I'd love that. But I've committed to stick around at my current place until such and such a time and I want to do right by my editor.' And I would say, well, just fuel up your getaway car.

You don't have to use it. Just create an account. Don't tell anybody about it. Try out the editor. You know, play around with it. Get comfortable with it. And very often in that time, you know, I get a call 3 days later. You'll never guess what happened. You know, I might actually.

There's definitely people who maintain free substacks while they are at the mainstream. I think some places have started to take a dimmer view of that. Even Paul Krugman, they told him to blog less, at least according to his substack. He writes these things, then he has this economics blog that gives him life and he loves doing and they're like, 'You have to publish it less frequently.' And he's like, 'No.' And now he's on Substack and he can write whatever he wants and he's making a ton of money and he's able to do the thing that he actually wants which increases the variance like it's not always the case that not having your editor makes you better but I think it makes you more fully yourself and that gets more interesting. You know I think Matt Yglesias was one of the editorial co-founders of Vox Media as a reader of his when he came to Substack after Wormtongue left in the Lord of the Rings like he de-aged 10 years and regained his vigor and kind of like became more fully himself.

Bari Weiss was very interesting. You know, she was sort of resigned from the New York Times, but after sort of extensive, you know, harassment and mistreatment, at least from what I saw from the outside, we sort of called her up right away. I was like, 'You should do a Substack.' And it took a little while, but she started what at the beginning was Bari Weiss.substack.com and sort of, you know, had this place where she could start building an audience. You know, there are some people who are sort of independent voices who are artists who go like do their own thing and have their own show. And there are some people who are I think of as founders, institution builders, people who want to, you know, who believe in institutions to the extent that the existing ones have failed yet hungry to create new ones of their own. And I love when Substack can serve those people. And I think Bari was unquestionably one of those people. She founded that Substack which became the Free Press which recently sold for $150 million and has become this like you know I would argue a great cultural force. I think it's really cool. It's really cool that something that left the mainstream developed a new on Substack then ends up getting welcomed back into the mainstream almost as a revolutionary change with the idea that maybe all of the mainstream will follow that.

I think this is often this is how countercultures work, I think, is that you have things that are sort of the that start out as sort of rebels or challengers from the outside. It's not that the mainstream becomes the counterculture, it's that the counterculture becomes the mainstream like the upstart, the rival elite, the people who are making the new thing, it kind of wins. And I'm sure that Bari feels like she's winning right now. One of the things I always felt was that some of the writers that I respected the most were what you could call heretics and the people who drew the most scorn from the media. It wasn't like at the time it wasn't like the you know the complete ideological enemies. It was sort of the people who were within the tribe who dared to criticize it. And you know, it's easy to kind of like lob bombs at your enemies, but it takes a kind of a really thick skin to criticize your own side and to raise problems with your own side. And you know, like I think Matt Taibbi was an example of this. Those people kind of found opportunity or took refuge in Substack. And the fact that those people were allowed to speak and push back despite controversy against them and against us, I think it's important. I think it and I think it actually helps the side. It helps when you don't silence your critics because when you can actually have valid criticism aired even when it's tough, even when it's contentious, that's kind of like how these things move and grow. And so as much as it's been painful over the years when people freak out about these things, I think it's worthwhile.

Yeah, I'd say so. I used to joke with people, it's like, you care about freedom, money, and prestige. I cannot offer you prestige, but the other two, yeah, we have those. Part of this was like we just wanted to help people that are making good things make money and the people that come to Substack can make lots of money. That was not surprising. The other kind of cool effect that it's had though is that people at those institutions, even the ones that don't leave, they have a lot more leverage.

And so we've—there's a lot of people who are making stuff who've gotten big raises not because they've come to Substack, but because they could go to Substack if they wanted to. The threat of Substack, the option of Substack, let's say, the fact that you have this other—there is this other thing you could be doing that gives you this like freedom, you know, gives you the sense of having other alternatives as possible.

A lot of professional gamblers started their career with a big winning streak. And the reason, of course, is because it's a selection effect. And if you start your professional gambling career with a losing streak, you often don't go on to become a professional gambler.

And I feel like that with that original Bill Bishop launch, like that thing was wildly successful.

And it kind of like I would say gave us a lot of courage. We went and did Y Combinator, which is like a startup accelerator.

It was wonderful.

You walk into a room of a bunch of other people who have this frenetic energy to make something that they really care about. And you get exposed to a culture where that's normal. And not only is it normal, but actually maybe we could raise our ambitions. Maybe there's a bigger version of this thing.

I would say way more camaraderie. I mean, there's a natural sense in which I'd say it raises your sights a little bit. It's easy if you have a little bit of early success. You're sort of like, ah, we've got this. And then you look around and even to this day like there are more successful companies in that batch than us. Like some of our friends and peers are just going on to great heights. And I think it gives you permission to be more ambitious.

No, I'd say we were able to build it. It wasn't, you know, we like—it was simple. It was simple. I sat down and wrote a bunch of the first things. I managed to lure—so it was Hamish and I at the start and then within the first month of YC, I managed to lure our other co-founder Jairaj to the company who's a brilliant engineer. That was a really big deal. I think mostly what it did was sort of it was a commitment device for us to decide not only are we going to build this, but we're building like a really ambitious version of it. And then after that, we sort of, you know, we got going. We had early customers, we had early momentum, the thing was starting to work. And we sort of had an idea that we'd raise a series A at some point. We had some like ideas for the metrics, but mostly we were just focused on building the thing. We were focused on getting the best and smartest people to come to the platform and write and make sure they were having a really good experience so that other people would see that and want to do it too. And there was one guy we were trying to recruit named Andrew Chen who actually had a very successful newsletter about growth for startups. And we were trying to recruit him and trying to recruit him like basically like quit your job come to Substack. But he eventually instead of doing that went on to be a partner at Andreessen Horowitz and he sort of reached back out to us and was like hey like you should come talk to us and we're like no no no we don't have time for that. We're like we're heads down we're building. And he's like, 'Well, you know, come for dinner with Mark. Come hang out. Like, let's talk.' And they ended up sort of like preempting our series A and putting some money in, which was like another shot in the arm, I would say.

My media consumption habits now I honestly read a lot of Substack.

Partly it's, you know, I can justify it to myself that it's like I'm working and I'm dogfooding and using the product, which is true and also I love it. I love—if you like to read it's sort of a dream job. It's really good and we're building a lot of parts of the product and I'm very involved in it and I have really strong opinions on it. I would say outside of Substack, you know, I read books a bit. I occasionally will watch something on TV, but really Substack is probably the majority of my media to be honest.

I would say it is the thing that social media can become. It's what social media should have been.

So, we started working on that several years ago and it was kind of the same story of, you know, originally I didn't want to have anything be free. I was like, we're going to be really pure and nothing could be free. And then it turned out that the free thing was an important part of how this worked. And we were sort of like that with the discovery piece, right? We were like, hey, we're going to build an app, but it's going to be purely about long form. It's going to be about only the things you're subscribed to because, you know, that is the core, which was true. But it turned out that as we were building this platform for people to have this direct connection with their audience, one of the most important things they could do was to grow their audience and get in front of new people. And so we were for a long time Substack existed in a world where we had these lofty ideas about you know creating a better incentive structure that would enable better things to flourish. But if in practice you were still if you were writing on Substack you were still downstream of the existing social media apps. If you were coming from legacy media and you had a massive audience you could just bring your audience sometimes. But if you wanted to grow, if you wanted to be a new person, you couldn't grow on Substack. You had to go to Twitter or you had to go to Facebook or you had to go to one of these other platforms. And that was a problem both sort of at the science fiction vision level of we're trying to make something different, but we're actually, you know, still sort of wedded to this thing. And it was a practical problem because those companies don't have a particular interest in helping you take your audience and go and own it. And you could have things like, you know, Mark Zuckerberg would decide we don't want to be in politics for a bit because I was mistreated over the Cambridge Analytica thing and we're just not going to have politics as much on Facebook. And if you're a political writer, that's a big problem. Or, you know, we got in a spat with Elon around the Notes launch. And so we sort of realized if we wanted to make the fullest version of this thing we were dreaming of, there was a piece that was missing. There has to be a place where you can go and discover things in the world where you can go and like be part of a larger conversation. That's a necessary piece of the ecosystem. You know, we were plugging into those pieces that already existed and that was imperfect and we wanted to make our own and we knew that was going to be a crucial thing to do. We also knew it was going to be really hard to do. It's like you know spinning up a new social network is famously difficult but we started working at it and it took a few years and I would say towards the end of last year we sort of got it working. When I say working, I don't just mean people are using it and looking at it and spending their time there, but it's generating massive growth and revenue. People are discovering things that they love enough to pay for and it's driving a large fraction of people's growth on Substack.

Yeah, that's right. It's, you know, there ought to be one network that serves the people using it.

Rather than the other way around.

Yeah.

It does still drive and connect to the business model though because you asked about algorithms. We got to the power of algorithms. The problem of algorithms is that is the same as the power. It's they're good at whatever you ask them to do. And so if you're a platform that has an algorithmic discovery feed and your goal is to get people to spend the maximum amount of time there, it can be very very good at that. And if you push that goal to the extreme, it'll end up being good of that in a way that is exclusive of you feeling like you're using your time well or maybe staying sane. And I think more and more people can feel—you described as sensationalism, but it's sort of like it's acting against you, right? It doesn't have your best interest at heart. It is optimizing you for some end that is not the end that you would pick.

It's the economy of clicks. It's the attention economy. And the thing that's different on Substack, it's not perfect. It's not a panacea. It doesn't solve all the problems, but it's like ultimately the only the way that we win is by helping you discover something you deeply value.

To the point where you choose to pay for it. And if I let you sit back on a Sunday and think, you know, as my best self, what do I want to spend my time thinking about and reading and what do I want to support with my dollar to see more of in the world? You might still make a bad choice. It's not perfect, but we've given you that choice. We've put that choice in front of you in a better way that lets you still make a real choice, but it's sort of as your better self in a way that's more congruent with the life you want to live and the person you want to become.

I mean the way I think of this is I think text versus video and image is a real delineation. Another one that I think about a lot is sort of short form versus long form. And in some ways, there's more similarity between a long essay and a long thoughtful conversational podcast than between a long essay and like a tweet.

Let's say. And when I think about letting people make new parts of the culture that matter, I think the other mediums matter, too. And the same way that in texts, having space for long form and deeper relationships and those things, I actually think the same is true in audio and video. And there's a lot of overlap between people who want to write and people who want to have a deep conversation. And the same lesson that we've learned through the app, which is actually if you want to power deep long form reading, the best way to do that is not to only have deep long form reading. It's to also have some ability to have short conversational things, to share quotes, to share pieces, to have the conversation, but then to give you a way in to the deep stuff. I actually think the same is true for video as well, but time will tell.

I think free speech and freedom of the press are integral to a free society beyond even sort of Substack. I just think it's one of the necessary building blocks of a free society. And on Substack because we've always had this value of independence of giving people the freedom to make the thing they want to make. You know, we've taken a very strong stance in favor of freedom of the press. You know, you can't organize crimes or make threats or there's a, you know, narrowly construed set of things that you can't do. But beyond that, we try to be very very liberal.

Not exactly that, but like that's sort of—we take a lot of inspiration from the first amendment even philosophically.

Actually, some of the early push back was just like nervousness around the new model and the fact that people could go independent and write their own thing kind of without the blessing of a media company or institution. You know, anytime we've had push back, anytime we've had criticism, I've sort of taken the mindset of look, if you can't take the heat, don't go in the kitchen. It's like we set out to do this thing and the only way that it was going to happen without controversy or without criticism is if we didn't succeed.

So, I can't complain about it too much. There's been times when it's been tough, you know, like there's people get like a very early one was there was sort of, you know, discourse around the trans movement, the trans identity issues about, you know, how we should categorize those things, what should policy be? And that's something that's like a, you know, a very legitimate topic for discussion. It's something that people have good faith disagreements about. It's also something that some people, it's part of their identity. It's who they are. It's how they feel. Things can feel like very personal or feel like attacks in a way that I deeply empathize with.

We don't have an editorial position. We think that freedom of the press is important. We think that you should have your own editorial position. Your Substack has your view and that we should support, you know, freedom of the press, freedom of association. If you don't like that thing, you don't have to subscribe to it. You have the power to remove yourself from it. But there is a school of thought and I think maybe especially earlier on in Substack's life, there's a school of thought that says that's not enough actually. And if you make a platform where somebody can say thing XYZ that is bad or harmful or dangerous or offensive and you're not actively censoring that or actively taking it down, you are in fact condoning it. But you're not condoning anything on Substack. Is that correct? Just to be clear.

No, no. Just to be clear, it would be impossible to condone everything on Substack. There's such a wide variety of things of all stripes and types. And I wouldn't want to run a platform that I condone everything on. I don't think I'm qualified for that job. I don't think I'm qualified to be the arbiter of

What's true or what's good. And that the people who ask tech platforms like ours to do that sometimes are perhaps well-intentioned but are mistaken in their belief that that's a good thing.

No. And that sense of independence is part of the appeal, I think. And the political winds have shifted since those early days. A lot of people who were critical of us for platforming people have faced censorship pressures themselves and have come to understand the value of a liberal commitment to freedom of the press. I also want to give the critics their due here or give the opposing side its due. There's a way you can go about this where if you just said look any kind of check on expression is presumptively wrong. And so the only way to actually have freedom of expression is for anybody to be able to say anything they want in any venue at any time and you kind of like throw the thing fully open. I actually think that can be a trap as well. You can create kind of like a Thunderdome like thing where it's the equivalent of like you being in your living room and people feeling free to come in and shout at you all the time and you're just like, 'Hey, this doesn't work either.' And I think some platforms can kind of like let that dynamic fly too far. So the point of Substack is not that there's no rules. The point of Substack is that there's not one set of rules. It's not Chris coming in and saying, 'Here's what everyone's allowed to say.' It's like your Substack is your house and you get to set the rules and you can have them be quite strict. You can say, 'We're not allowed to call names here or only Christian things or only anti-Christian things.' And that's good, right? Of course, because I think the thing that we need to show is that you can have freedom and civilization at the same time. It's not the case that the only alternatives are, you know, some centralized power that tells you what it's okay to think and say or complete anarchy where everybody just shouts at each other. You can with some structure and with some giving people the right tools and the right power themselves, you can have something that actually works and is beautiful and that people are free. I remember one in particular. There was a smear campaign early on.

That one was kind of like right-wing content. It was like, hey, there's offensive stuff from the far right. And it's true. There is some far-right stuff and there's far-left stuff and there's offensive things of all stripes. Well, here's another one because there's been a series of controversies of like why is thing X allowed on Substack. One of them was kind of like what's going on with trans issues. One of them was this kind of why are you allowing right-wing people? But the other one I'm now remembering was sort of COVID skepticism, right? There was people who were running the gamut from, you know, are these vaccines good to like where did this virus come from to are the measures we're taking against it the right ones? And there was really strong pushback and a strong sort of cultural and sometimes legal thing that was like, you know, you can't let people say this stuff. You can't let people question these things. And we took the position that like you got to let people question this stuff. And I think some of that stuff, you know, in my judgment is crankery, right? Like I think a lot of the anti-vax stuff is not right and probably does harm and is net bad and some of it turned out to be right probably like some of the people who were questioning some of the measures. I think you can I don't know if we've resolved the question of where COVID came from but I think it's at least an open question that's legitimate and to debate and shouldn't be shut down with accusations of racism or whatever. And that was, yeah, that was another kind of a moment for me that exposed why this stuff actually matters. You have to let people ask questions. You have to let people challenge the received wisdom even if they're wrong, even if they seem crazy. I just think that's a crucial part of a free society. And you know, Substack has been that. We've drawn a lot of criticism for that. Here's another piece of this is like I think there's a place where I saw a lot of companies go off the rails. I think especially in sort of like 2020 around that era was like the way these things would work was there'd be like this, you know, you get like a social media mob that would show up. Any surface on the internet that you would open would just have all of these people shrieking at you and telling you that you're the worst person and threatening you and all of this stuff. And I think part of what social media does is create a false illusion of consensus. It would feel like everyone was mad at you or everyone hated you or everyone thought what you're doing was crazy when really it would be like there's like a couple hundred people that are really ginned up about this. And I think it's very tempting if that happens to you to give in and to say, 'Okay, okay, okay. I hear you. I'm listening and learning. I'm going to do this first step to start making this better.' And I think as soon as you do that, you are lost. Either you're in control or the mob is in control. And as soon as you let the mob start to be a little bit in control, it devolves and devolves and nothing satisfies it. And so one of the things that we did, you know, and this it feels this way in the press and it feels this way when you get these social media things is as painful as it was, we did just sort of hold firm. We wrote a few essays in advance outlining our philosophy about, you know, free speech and freedom of the press and why we were doing what we're doing and why things were the way they were. And we could sort of consult back to what we had written with cooler heads. And then a lot of what I think of as our success was just not giving in, like not getting tilted, just being like, 'Yep, everyone's mad. The people who are our customers who are concerned, we'll talk to and we'll empathize with them and tell them what we're doing, but we're not going to abdicate our responsibility or our judgment to the critics in the press or to the critics on social media.' I think that saved the company basically. I think being willing to stand up in those moments feels hard. But maybe this is the advice I would give to somebody going through that is like stick by your principles. If you're going to get smashed, get smashed for doing something you believe in because that's worth it.

First of all you can use Substack just like a normal podcast host. So you can create a Substack, you can publish, you know, upload an audio file. It can distribute that to Apple Podcasts and to Spotify. We can also autopublish to YouTube now. And so if you're just trying to have like a good podcast host for free, Substack works for that. And you still get the subscription feature. So people can still come and give you their email and subscribe. We also have the ability to paywall. So, you can do a paid subscription and then people can if they're using their podcast app, they can add their private podcast feed and get the paid version. Now that the app exists though, those things work even better because anybody who has the Substack app can go to the listen tab and find the things that they're subscribed to that they want to read.

The app is definitely growing over time. I would say yeah a lot of the most voracious readers are increasingly using the app.

Yeah, you can also I mean we have a read-aloud thing. So as the author you can read aloud you can create your own audio version of the post which I actually love when people do that or we have a really good AI one if you don't do that or if you just want if you're in the car but you want to hear this post you can do that. The other thing I'm really excited about is, you know, we talked about for writers, the fact that you could come and type into this box and if the thing you type was great, everything else is taken care of. We're working on a set of features that I think will be able to do that for video and audio conversations. The current incarnation of this is Substack Live where you can go live from the app. And the thesis behind this is we're at the point with some of these new AI tools that if you can have a really interesting you can have something that feels like a FaceTime conversation or a video call and if you can have the most interesting conversation in the world, we can make all of the other pieces sort of work automatically in a way that's sort of newly good and I think something may be possible in that realm like it was for writers where it's like there are a lot of people who could have a really interesting conversation but I don't have to tell you that the mechanics of making a really good recording and editing it and having all of those pieces come together like I think the status quo even today in the world is you either have to sort of be an audio nerd yourself or hire a team of audio nerds, even to make, you know, forget about an amazing album, but even to make like an acceptable podcast is pretty difficult. There's still a pretty high barrier there. And I think we're going to be able to dramatically reduce the barrier to the point where anybody who wants to have a conversation and publish a great artifact of it will be able to just do that.

Yeah, I think conversation is I mean you don't have to you could also just sit there and give a monologue to camera, but I think conversation is the much more common and much more natural format for those to be really interesting.

I mean, we're going to ship some iterations of this video recording live stuff that just make it much more powerful, especially the editing, the ability to, you know, make cogent clips or, you know, the bar for how well a human can do it that's really good is like very very high. Yes. But the bar for how good it has to be before it's like serviceable for a conversation is actually still fairly high, but is much lower than that. And I think we're going to get to a world within the next month or two where anybody who wants to make something that's a podcast or a conversation is going to be able to do that and have it be sort of automatically pretty good.

Yeah, I think in the limit it should be able to be really good. There's a more interesting question which is do you need the humans at all? Like why not just listen to the best AI conversation instead of just the interviewer and the interviewee which I think is a very deep question. Again, if the content is good, does that matter? I don't know.

Lots of little things. We have a rule. We never actually use the word AI in the product. I feel like it's cliche and cursed vibes right now to be like, oh, your AI assistant is going to do the thing. I'm like, oh god, I hate that. The way that we think of it is, can we make the product more magical? Can we make it magically do the things you want it to do?

There's one I think maybe no idea might be too strong, but one thing that I would love just nerdily. So, we're building this conversation feature and it's all sort of FaceTime, you know, remote calls. I think what you and I are doing right now is a thousand times better than that just from the sense of having a human conversation. It's a much more technically complicated challenge. If you wanted to say could we make this be within anybody's reach so they didn't have to be at a studio or didn't have to have special equipment. What would it take to get anybody to have the ability to sit in a room with somebody and have that turn into world-class media? That I think is much harder, but I'm very excited about. Basically, I think that would be truly magical.

I'm pretty interested in that. One thing we have seen that's cool, you know, a lot of people have asked us about various sponsorships and how do these things work. One that has been really cool is this guy Lenny Rachitsky has like one of the best Substacks and also like an interview show about product management and tech. He's kind of like a huge figure in that world and he's done various kinds of sponsorships and things. But one of the things he did is he got a bunch of really high value deals for companies that were sponsoring him and he bundled those into the subscription. So he said, 'Hey, if you're a subscriber to my Substack, you're going to get this, you know, very valuable year of the pro plan of this thing.' Or he had like a bunch of sort of like, you know, high value software products that he put into the subscription and it was like extremely successful.

There have been some moments like that. I mean, we talked about there was sort of the 2020 era where there were sort of like a wider spate of cancellations or shifts in media.

Andrew Sullivan joined in that time. There was a bunch of people.

Yeah, there's been bumps. We had a big thing this year when there was sort of like the TikTok ban drama.

So, there was I think the law might still be that TikTok is supposed to be banned or at least it was at the time, but there was a big moment where it actually did shut down for a day.

And we had a lot of people from TikTok start a Substack.

TikTok creators who maybe didn't even move or were just like I don't know what's happening with this app. Yes. I newly realized how important it is for me to have some way to contact my audience. And what didn't work I don't think for almost anybody was I'm going to start doing on Substack what I did on TikTok. But many people who brought their audience then realized oh there's more I can do here. Like oh you mean I could write something and people could read it or I could make a longer thing and people might check it out. That was sort of like a big moment. We've had a lot of interesting controversies. We've had various times where people have been angry that we, you know, take a strong stance in favor of freedom of the press and allow various points of view or various things that people disagree with. I expect we'll get like one of those every year or two for the rest of my life if we succeed.

So I guess maybe early on in Substack history, we were very symbiotic with Twitter in the sense that this was a platform for long form writing. You know, the OG Twitter was very, as you say, it was sort of like the short form social network of the literate of people who wanted to read. And old Twitter in my mind, a lot of what people were talking about would be links to long form things. And links performed very well. And you know, a big part of why Twitter became what it became was it was sort of like the place you would go for the headlines. And so in the early days, a lot of those moments where people would come and bring their audience. It would be somebody who had a following on Twitter who would say, 'Hey, I'm starting a Substack. Maybe I just got fired or maybe I'm just striking out on my own. You know, come check it out.' You could just post a link and all your people would see it and if they were compelled by it, they would come.

Yeah. And then, you know, the conversation would live on Twitter, but there you could still have a long form piece of writing that would do the rounds. It would be like, 'Oh, yeah, everybody's reading this thing.' There'd be a conversation about it. And yeah, that was like a major driver in the early days. Over time and actually even before Elon bought Twitter that became less and less true. I think as they optimized the algorithm, it ended up penalizing any kind of links out at least at the start. Not out of any malice, I don't think, but more just it makes sense given what you're optimizing for, right? And if you're optimizing for time spent scrolling such that you might see an ad, if somebody clicks out to read a thoughtful long form thing, you're losing money given the objective function that you might naturally create for that algorithm. Those things will penalize. So it became a smaller and smaller share of like the top of funnel traffic that was helping people on Substack grow. And then Elon bought Twitter. I talked to him at some point. We were sort of comparing notes and

I think he was at least a fan of we at that point had I think been the platform that had taken a pretty strong stance in favor of freedom of the press. A lot of the things that he at least said he espoused were things that we had been doing. And so I think he was sort of at least theoretically a fan from that perspective.

Yes. Although I would say given what's happened since, maybe questionably. So, but at least on that core idea of like, hey, there just has to be freedom for people to say the things they believe and want to say. He at one point floated the idea of Twitter buying Substack and me coming to run Twitter just as like a thought experiment style thing. And when we were about to launch Notes, which is like our feed, I kind of gave him a courtesy heads up. We'd been having this conversation. I was like, 'Hey, we're launching this thing. You know, we think it's important. It's something we've been planning for a while. You know, we're not trying to mess with what you're doing.' But we launched it and he was very upset. He actually asked me not to launch it.

because he saw it as a Twitter competitor. And I think there was a moment there where there was sort of this meme of like is Twitter actually going to fail? Is this going to tip over? People going to switch over to BlueSky, switch over to Threads or switch over to somewhere else? And so he saw us launching this feed as kind of I think a declaration of war. And he banned all mention of Substack on Twitter. There was a week where not only could you not share a Substack link, if you just said the word Substack, nobody would see your thing. And if you search for Substack, you literally you'd search for Substack on Twitter, it would say no results, like doesn't exist. We were like Voldemort, you can't say the name. And that I think after some backlash, they canceled that policy pretty quickly, but left in place a bunch of kind of like underhanded things that would hurt traffic. I think Substack and the New York Times were the two sites for a while that got the treatment where you would click on a link and it would go there, but it would delay for 5 seconds. Like you just click and it would just be like spin and 5 seconds sounds like a short amount of time but in software it's an eternity.

It was intentional.

And there was like various deboosting and all these things and I haven't talked to him since.

I think in the original like when he literally like you couldn't say the word. I think there was like a general uproar that's like this is ridiculous like you can't be a free speech platform and then ban discussion of a commercial rival that you don't like. And I think that's one of those just like an emotional thing that gets a lot of push back and you tie it back. But to their credit, one thing that I think has been happening recently is there's been a big discussion about links on Twitter in general. And one of the things that the hardcore users have complained about is this long decline of like interesting things linked out. And they're actually testing new features now that help somewhat. And we've seen an increase of traffic in the last few weeks. So I have some optimism that they're working to fix that.

So the biggest difference from Medium is the business model. My view of Medium is they took sort of the underpants gnome theory of building one of these things which is like step one get a bunch of attention question mark question mark question mark step three profit. And so they sort of had this period of trying out a bunch of different business models, one of which was very similar to the Substack business model, but through most of Medium's history, there hasn't been any idea of like direct connection or ownership as a creator, as a writer. And so like on Medium, you'd pay five bucks a month for all of Medium and it would be sort of Netflix style. It would like give you some slice of the thing if you clicked on a thing. And what that means is if you're making stuff on Medium, you're kind of like playing to the algorithm all the time to like get anywhere. And very early in, you know, when we were still in YC, actually, Medium used to publish, here's what the top earning writer on Medium made last month. And we would look at it and be like, there's people on Substack that are making more than that. And they're not making more than that because they had the one hit that they could never replicate that happened to get a gajillion clicks and then the algorithm doled out a big paycheck. They've got that because they've got a loyal audience of people who value what they do. It's just such a better deal creatively and financially to have some connection with your audience and to have people who are showing up and paying for you. And so I think it was able to attract a much better caliber of writer over time. And then Patreon is very interesting because Patreon is similar in some ways. I've talked to Jack a few times and I think maybe early on I would have said Patreon was doing the thing where they were trying to be very pure and they're like we're really just going to be about the payment relationship. Jack's a musician. He's like, I want to be so creator focused and friendly that I'm never going to try to impute on the relationship at all. So, we're just going to handle the payment for you and we're kind of not going to do the rest. And you're not really consuming the content on Patreon. It's the prototypical thing is you're a musician or you're a YouTuber or you're somebody and they didn't want to do discovery. They didn't want to help you grow because they felt like it would be sort of tarnishing the purity of the thing. And I've argued with Jack about that over the years. My view is he's come around to my way of thinking and they're looking at Substack saying, 'Oh, one of the most important things you can do for creators is help them grow and find an audience, especially new creators, especially the next generation of people who are trying to come up.' And now again, I'm biased, but my view is they're just copying a lot of the things that Substack is doing, which I think are good ideas, but in terms of like having a network that's a place on the internet that you go, I don't think Patreon has achieved that yet.

You can comment on posts basically. And you can also reply to the emails from very early on, which is a slightly different thing.

If you reply, it only goes to the author.

I think that's understood. We originally actually had it where replying would leave a comment and people did not understand that and we would end up with a lot of things. We ended up very quickly with a lot of things that were intended to be private that were posted and we had to cut that out.

But the comments are often very good. One of the things you can do is you have, you don't have to, but you have the option to have commenting be only for paying subscribers. And the joke I sometimes use is that people will hate read something, but they won't hate pay for it.

And honestly, if they do hate, if it's like, I cared, I hate it enough to come and give you my $10 to leave this angry message. Well, maybe that's worth it or maybe that's interesting anyway. But a lot of people on Substack, the value they get from earnest commenters and earnest replies, the feeling of people engaging with the ideas and caring and talking about it is a big piece of what makes the thing kind of special. And now that the people are in the app, it's much easier to comment. It's much faster. So you're getting a lot more of that. And one thing that I've followed from like the early internet blogosphere is a lot of the most interesting bloggers kind of like came out of comment sections. Like a comment section of a popular blog or a popular Substack can be like its own scene where its own little universe of people that get to know each other and bounce ideas off each other and become known and then you can sort of get people that kind of grow up in the comment section of one thing and then go and start their own.

My number one piece of advice I always give people is just start. I think the most common failure mode for somebody who aspires to do a Substack is to think really hard about it. Do a lot of planning and a lot of strategizing. And by far the best thing you can do is just it's easy to start. It's free. Set it up. Put something out there. Don't worry about it being the perfect thing. I also think you know different people take a different tack with this but I think a good default is default to creating more frequently. I think the internet in general and definitely Substack there's sort of a natural benefit to having sort of less filter and being able to like publish frequently putting lots of things out there. You know, if you put 10 things out there and eight of them are kind of so so and one of them is really great, that works.

Even up to one a day would be not too much. A lot of the most successful Substacks do five a week or more.

Yeah, I think people are for things they really like, they have a higher tolerance. The other thing I've heard again and again and again from people is I'm so frustrated because this thing that I worked on and polished for a month and put my heart and soul into kind of came out to a flop. It was people read it but it sort of didn't really do anything. And then this one thing that I slapped off in half an hour when I was angry in a parking lot or like I had something that I just kind of like came through me and I just dashed it off and I wasn't even sure but I sent it before I even thought about it. And that became the most popular thing I ever did or that became the thing that got everybody into my work that got them to read the other stuff in the first place. Have you ever heard the story of like the two sculptors?

There's two sculpting classes and the teacher for the first class says, 'Okay, at the end of the semester, I'm going to just take your very best piece. 100% of your grade is going to be based on the quality of only the best thing you made.' And the other teacher goes to the class and says, 'I'm going to give you a grade by the pound. The more pounds of sculptures that you make, regardless of quality, that's going to be the grade you get.' And in this made-up story, what happens is the people in the second class, if you when you go back and look at the best thing they made, it's much better because of the practice. Because of the practice, because of the benefit of momentum and getting going. Because when you set out to only make the one best thing, it can be so paralyzing. And you can spend all of your time, you know, polishing this refining. And in many cases, you would have been better served by getting more out and giving yourself the space to like iterate and to try more things. And sometimes many times in creative pursuits I think sometimes those accidents are like where the magic happens.

I mean a lot of what we try to do in the product is help people magically get promoted without having to be self-promotional. A lot of especially writers I find have this allergy to talking about their work, publicizing it, like asking people to look at it. And so we try to do a lot to help make those things kind of happen magically and automatically. But in general, like put your link in your bio, share the thing you wrote with people you respect. Like it's okay to tell people about the thing you're making.

Maybe we can't be a successful media company, but we're not trying to be a media company. You know, I think a lot of the most successful media companies of the next decade will be built on Substack. And so the parts that I think are like the core of Substack that we are committed to is the way that people on the platform make money should be doing the work they believe in. You should be able to make something truly great and be able to like make real money in a way that pulls with that rather than against it and that the creators are kind of like in charge of. And Substack should make money when they make money. The creator should be getting like the large lion's share of the value. Those are kind of core things for us.

I wouldn't say it's about journalism. There's a lot of really good journalism on Substack. More I think than people sometimes give credit for, but I think it's broader than that. You know, I think it's about culture ultimately. Stories and ideas.

I think Substack has helped journalism in a time that's been very fraught for journalism. I think there's a lot of stuff that happens on Substack that is great, that is good journalism that otherwise might not exist. It's been such a challenging time for that profession that I don't know that it's like if that's even the main change that's happened in the past, you know, 10 years, but I'm optimistic.

One thing that springs to mind, you know, Jonathan Haidt.

So, he started a book on Substack. He started serializing it about like social media and phones and all of this stuff. And I think he published a few chapters and he made a thing that eventually became like a best-selling book. I feel like we're probably still in the early innings of kind of like what I think of as the smartphone backlash or moral panic depending on your point of view. And a lot of that stuff was cooking on Substack pretty early.

Yeah.

Yeah. The same people who read it will buy it again. Yeah. And in fact, having an email list of people that love to read you is one of the best places to sell a book.

Yeah. That's one place that I'd love to expand into. I think the product needs to get better, but serialization and especially fiction. I think there's a lot of room there that we haven't tapped into as much yet.

Yeah, we're running some experiments along these lines. Now, I find it very interesting. One of the things that fascinates me is like, you know, we talked about the media company of the future. Like what is the media company of the future? What are you know, if you're an ambitious media founder right now, what should you be making? There's one idea that's like I'm going to make something that's like a newspaper. But there's another case I think that says maybe I'll make something that's like a record label where I'm not trying to create one unified editorial product necessarily, but I'm trying to kind of like spin up and help mentor or make or produce or have this kind of like loosely affiliated set of voices that maybe you can get them individually or maybe you can get a bundle but the enterprise that I'm making, the company that I'm making is less a singular editorial viewpoint and more kind of like a scene or a collection of people. We're very interested in that right now and we're testing out some bundle models that are like this where people could either start a company and make a bundle or kind of group together into a bundle and see if that helps.

Yeah,

As it becomes more and more of a hub of Substack being meaningful as a discovery engine.

We're starting to see that matter for writers and creators, too. People are coming to Substack. It used to be like, you know, no one's ever heard of this, but I hear people are making money. And now there's people that come that are like all of the interesting things I read are here. And I feel like if I'm not here, I'm sort of not even in the conversations that I find most interesting.

They kind of change over time. We have these eras, but there was a long time when it was kind of like the sort of the heterodox, you know, the Bari Weiss axis. There was like a period where people thought of Substack as that, you know, the right wing of the left mainstream kind of, you know, we went through a whole Bitcoin era where there was like a Bitcoin rally and there was a huge segment of crypto stuff. We're in kind of the, you know, Kamala Harris has a Substack now. We've got kind of like the I would say the mainstream Democrat universe is like thriving on Substack in 2025. We've had these eras and at any given time it's tempting for people to like think that the current flourishing that's happening on Substack is the whole platform, but the reality is that it's this index fund of culture. It's got all these different things and it changes all the time which makes it fun.

There's a lot that are very good. I mean, one that is kind of special to me is Astral Codex Ten, Scott Alexander. He's sort of a rationalist essayist and thinker in the weird Berkeley rationalist scene, but he's somebody that I've been reading for a long time that I really like.

Substack Defender. Oh man. So, we had a thing that kept happening because you'd have these especially like local journalism. This happened a lot where somebody would be covering a local business or politician negatively and they'd be some independent person that's just trying to, you know, maybe there's no local newspaper anymore, but they're taking up the thing. And they'd write some negative story and they would get a really scary letter on legal letterhead that basically says we're going to ruin your life unless you shut up. I mean, there's very strong legal protections for journalism and speech and criticism in this country. And so very often these were just bogus claims or claims that did not have a very strong chance of actually winning in court. But the ability to like make the threat if you're an independent person can be kind of debilitating because even just the cost of defending yourself can be very high and like you don't really know like how are they going to be able to find something or what is this thing and so we created this program called Substack Defender that was basically like we're going to have a fund for picking up defenses of these things that anybody can apply to. We'll pick which ones we take and we're going to pick a few things like this where somebody is kind of trying to do censorship by lawfare. I think of it just like really vigorously defend it and put a bunch of weight behind it, put a bunch of money behind it, try to like, you know, publicize it if necessary.

Yeah.

That's great. We've won a few of those. It's very satisfying.