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.