Chris Best of Substack on the Future of Media

0:00Let's talk a little bit about the future of media. Are people going to be reading less? Great writing, great media, great culture in general is this inherently valuable thing. We've entered a world where attention is the scarce resource. There was one platform that stood up and said, hey, we are protecting free speech. And that was substep. This was also an era where the blogging ecosystem was sort of dying, a really important moment to actually save blogging and writing on the internet. In the early days, people would often say to me in an accusatory tone. Substack is just blogging with the business model.

0:32And I was like, that sounds pretty good. We've been talking a lot about disrupting media. What are the big plans here? I aspire that the Substack app could be a place where you look back at the time you spent on it and think, damn, I'm glad I did that. That made me a better person. One of the future of media is in control by algorithms or legacy institutions, but by independent voices building directly with their audiences. Today on the podcast, I'm joined by Chris Best, co -founder of Substack, along with A16Z General Partners Katherine Boyle and Andrew Chen. They traced the origin story of Substack in its cultural impact from standing up for free speech during a turbulent 2020 to reinventing the business model for independent media.

1:11We also get into the evolution of blogging, the rebuttling of media, and what the future holds. Let's get into it. Katherine, we've been talking for years about how much we love Substack even before we were formally affiliated Affiliated with the company. Why don't you go first and talk about what you find so remarkable or striking about Substacks impact. I think the impact is truly understated and I think we've moved so fast as a country and as an internet and as a world in the last few years that we've sort of memory Hold what it was like in 2020 2021 particularly for media how crazy the 2020 moment was for anyone in the thought leadership space anyone in the media space So let me just go back to the summer of 2020.

1:57James Bennett, who was the editor of the op -ed page at the New York Times, was forced to resign for publishing a sitting senator. An op -ed by a sitting senator who was still in office. The craziness that was around writing anything that was seen as heretical or asking questions or something that was seen as unorthodox in 2020. There were mass firings, Twitter de -platformed a sitting president, Facebook as well. Well, it was an extraordinary time, and I would say a fearful time, where very many people were afraid to say what they were thinking. There was always rumors of people having unfettered conversations, like how dangerous it was, that people were having these conversations behind the backs of journalists, and there was one platform that stood up and said, hey, we are protecting free speech.

2:41And that was sub -stack. And I think people forget that because it's just seen as, oh, of course, we're in this new time, you know, Elon bought Twitter in November 2022. the over -tune window has swung open. People can say what they thought. And I think people have forgotten that only a few years ago, we were in desperate times where people were losing their livelihoods. No one was willing to say that freedom of speech was under attack. But the one platform, the infrastructure that was there to support those people, it was Chris, it was Substack, and they never wavered. And so I think that is the cultural impact, like where we are today, we would not be where we are today without Substack.

3:15So I get very emotional. I'm like a super fan of Sudstack. I was on Sudstack in 2021. I'm very proud of that. But it's one of these things where I think we need to remember that we could have been living in a totally different time and a totally different culture. Had people not sit up and had the courage to say that freedom of speech matters. Yeah, and this was years before Elon and I bought X and it was just the first batchion of free speech. Chris, why don't you talk about sort of when was the moment or what was the evolution for how you guys decided, hey, we're gonna take this stance, even if it's gonna upset some of our most important writers, even if you're going to upset some employees, some investors, the ecosystem, talk about what I was like for you.

3:50I've always seen the free speech thing as sort of an important pillar, but not the main pillar of what Substack is actually setting out to do. The way that we think of Substack is making a new economic engine for culture. And the idea, and it's not a partisan idea, it's not a political idea directly, it's just this idea that great things are made by independent voices who can do the work they believe in, make money, have editorial freedom, have a direct connection with their audience. Basically, the backdrop of starting Substack was just this idea that, hey, the internet came along and smashed a lot of the existing business models for culture.

4:30And what came in the wake of that was these massive internet scale networks that are phenomenal businesses and that connected everybody, like never before, or had a lot of amazing positive attributes, but in my estimation, in our estimation, we're kind of driving us crazy. And the core of Sub -Sac is this idea of independence, this idea that the individual left to like do the thing they believe, say the thing they believe, make the thing they believe, supported by an audience that's there for them, is this like crucial ingredient in a healthy culture in a free society. And freedom of the press, freedom of speech, is one necessary precondition for that.

5:13And I kind of think that in the long arc of history, that's not, hopefully, that controversial of an idea. I think it's a very American idea. But at the time, because of the world it was, it was, it was kind of out of vogue, shall we say, quite severely. And I think in 2020, the thing that surprised me, the people that felt the brunt of that were not conservatives, or not Republicans necessarily. It was the people in the liberal media. In my telling, I would say, selectively the best and most interesting people, though we're getting just thrown from the ramparts. And the fact that this thing that we were creating this new economic engine for culture that gives you this independence happened to be there at a time where a bunch of the most interesting writers in the world were getting summarily tossed from their long -time institutions that lined up really well for us from a business perspective.

6:05It was spicy from a cultural perspective, but that's the gig. Just quickly add, you know, I was going to say that it's amazing to see on the other side of the coin, which is the blogging ecosystem. How much that's changed? We've gone through kind of live journal and Zangun blogger and we had Google Reader RIP and then you had kind of basically a phase, Chris, when I met your co -founder, or Hamish initially, and the company was three people. This was also an era where the blogging ecosystem was sort of dying. And you had sort of the open WordPress -powered blogging ecosystem, but there was no economic model.

6:42You ended up with a lot of spam, a lot of people hacking like these poorly maintained PHP websites. And so I think this was also a really important moment to actually save blogging, really, and writing on the internet to actually create a model that for a long time people just thought, oh, well, I'm just gonna plug XYZ Amazon book and get affiliate fees, or I'm gonna put Google AdSense all over my blog. That was the only way to create any sort of economic thing. And for all of us that are in tech, it was cool to see that you had Ben Thompson from Stratekery really show that, oh, there's maybe an alternate model, but it was almost like always like a curiosity and something that was like annoying to actually build.

7:23You'd have to set up your blog, you'd have to set up your payments, You'd have to do all these other things. And so I think also a really important moment for sub -stacks to kind of emerge from the internet media side to actually clean that all up and actually make it easy to actually put together something that became the big economic engine. In the early days, people would often say to me in an accusatory tone, sub -stack is just blogging with a business model. And I was like, that sounds pretty good. If that's all it was, that would be pretty cool. And it turns out it's more in spot -casting.

7:51It's a whole network, but I don't know. So it seems good. Yeah, and it really achieves the dream of sort of reaching your audience in the sense of if you have a hundred thousand Twitter followers But you can't really engage them and you're dependent on the platform and that's not as thrilling as owning your own email audience And what I love about what you guys did is you took the risk that hey, we're gonna give people their emails And they can choose to leave if they want to as opposed to being trapped to the platform But we're just going to build such a compelling offering that writers are gonna want to stay and it's amazing years later to see a large majority, if not all, of the biggest writers, stay on the platform.

8:28There's only one thing that's better than people staying on the platform, which is when people leave the platform, take advantage of the export features, and then subsequently return to open arms and come back, we call them boomerangs, and we love to see that too. I think the right to exit is really important. People thought that was very dumb. They said, well, if you just let your customers leave, won't they just leave? And I think in the short run, that might be true, but in the long run, that created the right structure for us, like it meant that we have to, and still have to build a network that has enough value, that even though you can leave, you don't want to, and even if you do leave, you might choose to come back.

9:03And I think that has caused us to keep the right thing at the forefront of our minds. But I would say there's, I think there's something even more important about the direct connection, which is it's not just that I can leave. It's that in my mind, what a subscription is is the option to give someone to like reach out and tap you on the shoulder. This is to say, if you don't have to send me an email all the time, if you don't want to, but if you want to send me an email, if you want to send me a push notification, if you want to show up with half my inbox, I kind of like give you that, right? And something that that lets you do as a writer or as a creator is to take creative risk.

9:35Something that I hear a lot from YouTubers is people who are very good at YouTube, people have massive followings who are very successful who say, I have this idea for a thing that I could make. And I know that it would be great. And I know there's an audience out there who would like it, but I can't make it. Because if I made it the way that I want to make it, no one's going to see it because it doesn't please the algorithm. And so the direct connection, in addition to being this way, you can bring your audience with you, is a way to give humans the power to override the algorithm and say, hey, I've got this trust relationship with my audience.

10:10I want to exercise it and go out on a limb and say, hey, I want to call in that favor and like, have you pay attention to this thing that I'm saying is good? And sometimes it might be bad and you might unsubscribe. But sometimes it might be great and it might be something great that could not have existed if the only way to reach everyone was to please the algorithm every single time. So in the beginning, it was a blogging platform with a business model, as we just said. And the vision has gotten bigger into more of a network, more of a platform across formats. Expand on what is the big vision for Substack.

10:40I'm also curious how that's evolved, if that sort of the vision in 2018, 2019, 2020 is the same vision as it is now. So it's also vision that we can trace the evolution of it. I would say that we started from the very beginning with this, think of very ambitious, some might say, derangedly ambitious vision. Again, the backdrop was kind of, we think that the internet has massively reshaped the economic incentives for media. and actually the origin of the company, I'll just briefly tell this because it's German here, was I was taking a time off at my last startup and I'd always wanted to be a writer.

11:16I'd always been an avid reader, I've thought that what you read matters. And so what you read, the media you consume is not just a way you spend your life, it changes who you are. It changes who you are as an individual, it changes how you see the world and it changes cultures and societies. And so great writing, great media, great culture in general is this inherently valuable thing. And my first instinct was I should make some of that. Like I could write an essay, how hard would that be? I know how to program, I know to type. And I started writing what was supposed to be this essay or this blog post detailing my frustrations with the media economy on the internet.

11:51So this is where it started. I'm like, wah, wah, wah, look at all these great things in the internet is done, but it's also kind of like created these memetic evolutionary landscapes that are driving us nuts. This is going nowhere good. look at how the culture is shifting, wah, wah, wah, and I sent this essay to my friend, Hey, Mish, who's actually a writer, and he let me down very gently. He said, it's 2017, and your essay is about maybe the newspaper businesses are in trouble, and maybe Facebook is not an unalloyed good. Dude, we know, everybody knows that, or everybody who's in my industry knows that.

12:25But the better question is, let's say that all of those things you're complaining about are true, what could you do about it? How could that be different? And that we started arguing about that. And so we had this sort of, I think maybe the, this is an A16C relevant thing is this sort of techno -optimist idea that it's like, look, you're not gonna turn back the clock. If there's new powerful technologies that are changing how everything works, and those things come with trade -offs, and there's like upsides and downsides, and there's contingencies. There's historical contingencies where the world could tip in one of many ways.

13:01The right way to address that is not to lament it or to wish, hey, we should go back. It's, hey, we should put these things to use in service of people. We should imagine what the best version of this future is as these new networks take off, as these new technologies take off, and we should work proactively to help usher in the better, freer, more exciting version of that future. Heady stuff. And then, so we had this big idea idea, this big sort of grandiose thing. And then we just had the kernel of the way to start. And the way to start was we could make it dead simple to start a paid email newsletter.

13:41And that was a thing that there was probably like 20 people in the world that really, really wanted it. But they really wanted it. Like it was going to be the best thing ever for them. And it was the kernel. It was like the smallest possible instantiation of that much bigger idea where you were going to create this new economic engine that lets any independent voice make the things they believe in make real money doing it. I mean, it's a way around the cold star problem because you could have an individual person, like the very first sub -sac news letter made total sense. So we started with a very grandiose version of sub -stack firmly fixed in our minds, but I always imagine even then I think we looked at YouTube as the something that was like maybe the closest version to this thing that that already existed.

14:23Talk more about how you decided to launch notes or go from, okay, we've got this sort of business engine where we've got all these writers making a lot of money. Where do we go from here? I'll tell one step before that because it went into my thinking. But very early on in the very early days of Substack, we were like, okay, the thing that's going to be really different about Substack is it's all going to be paid because that's the thing that aligns the incentives, that's the thing that makes this thing different. And so in order to be very pure to our vision, We're not going to allow anybody to have a free sub -stack or to like send emails to free people.

14:57And that evaporated with our first customer because he was like, oh, okay, then I'll just use MailChimp for the free version and then I'll, yeah, funnel the people here and he created this stitch together thing. And it was like, oh, this is really dumb because if you want to be successful, if you want to make a successful paid sub -stack, you have to have a free sub -stack. And in order to make that experience good and have the conversions actually work, we should just support that. And it's not an abrogation of our vision. It's actually like, you need, in order for the thing to work, you have to provide this other thing.

15:30And then the thing that we realized not too long after that was the same was actually true about Twitter and about the social networks, which was, you know, in 2018, 2019, if you wanted to have a successful sub -stack, you had to also have a successful Twitter or a successful Facebook or a successful LinkedIn increase. Like you had to have some top of funnel place. You know, the same way that the legacy media was struggling and said like you had to have Facebook traffic or you had to have Google traffic or you had to have something. There was always these other networks that were the source of your business.

16:08So even if you were this independent writer, excuse me, independent creator, you were downstream of these other platforms. And that had both a philosophical consequence, which is we're trying to make this place that has these different incentives, but you're still at the whim of the crazy, the Thunderdome, right, you still have to play the Twitter game or you still have to play the Facebook game. And it had this very practical problem of those networks don't give a shit about you as a creator that makes money. And, you know, Mark Zuckerberg can decide an a fit of beak that people are annoying him about politics, so he's going to like turn off politics.

16:50And if you're a politics creator that depends on Facebook for your livelihood, you know, that's a existential event. And it's not even because it's like they're trying to do that. It's just like, hey, these networks twist in turn. And they don't really have any intrinsic interest in helping you build your audience and make the thing you believe. And so we had this idea that in the long run, the only way we were going to like really make that work for people is to build one of these networks ourselves that was built on different laws of physics. And so we were going to build, you know, a network, a place, a destination, a place that you could go and experience the internet and have like all of those great things that you get from social networks, but with a different business model and with a different incentive structure.

17:41And it would be, it's not going to like replace them, but it'll live alongside them. And it'll be like the one place on the internet where it actually does want you to succeed. It actually does want you to go and find something interesting and long form to read or long form to watch. It does want you to like find and fall in love with something enough that you might choose to pay for it. And that's going to create a very different feel from everywhere else that just wants to keep you glued to the screen. So we had sort of this like, feel like theoretical idea of why we had to do this thing. But we also knew that it was going to be quite difficult.

18:12Like it's very hard to start a new internet scale network. And it took years. And then, Krabbeth and Chris, to your earlier point on this on the algorithm, it's so interesting to watch actually all of the major platforms move towards the algorithmic for you, you know, world because in that world, then actually the creator's relationship with their audience is even further away, right? Like it's literally like it actually maybe it doesn't matter. And this all originally started with, oh well, you know, we have this problem of any, you know, social app where you need people to follow enough folks so that they get enough, you know, feed content.

18:52And well, one way to solve that is even if you're not following somebody, maybe we'll just kind of suggest things. And it turns out then the algorithms are so good that maybe that should be their entire feed is just suggested content. But then what does it mean as a creator to even build a following on one of these platforms if even if you have 100 ,000 followers or whatever, maybe they'll see none of your content because the algorithm is caring less and less about the follow -up graph these days. Definitely. And I think there's two, And there's two tax you could take with that. And the one that I think a lot of people, their first reaction is to say, oh, well, algorithms are bad, right?

19:32Like the algorithm is whatever. It's severing our ties, it's putting us into bubbles, it's exposing us too much to people outside of it. But like whatever the thing is, you know, okay, so there's trade -offs with algorithms, therefore algorithms are bad. I think a more productive take is algorithms are powerful. And there are two other people use. and they serve the ends that we tell them. And if we tell them better ends, they'll help us get better results. And so this is something that we talked about a lot at Substack, because I think people had this, there's a lot of our users who felt like, at the time, they're like the good thing about Substack is there isn't an algorithm.

20:10And I just connect directly, and that's the thing that's actually good. And I think the take that we have is there's something is much better than that, which is what if there was an algorithm that actually served you. And those actually trying to help you find the things that you deeply valued and actually had a, you know, like the nerd term for this is an objective function. If the objective function was actually closer to, in other words, the secret hidden master that the algorithm is serving is actually your own interest rather than, you know, trying to sell you more ads. You have a very sophisticated writer base and then by extension a very sophisticated reader base, very high value audiences.

20:50And now, especially with video and people aren't used to paying for video in the same way they used to paying for writing, partially because of your sub -stacks innovation there. Will you also launch an ad network at some point, or do you think that risks the golden goose in some way, or how do you think about that? I kind of take the same thing we talked about with an algorithm, the same thing about building a network. I'm going to say the same thing when we talk about AI, which I assume we will do. But I see sponsorships advertising is a powerful force. And I think there are definitely like the thing that would break sub -stack is if we just looked at the same way that the legacy social media things built advertising and said, oh, we're just going to copy that.

21:34Like, that's going to work. Because if we did that, the thing we would be doing is importing the incentive structure and the business model that puts the platform at odds with the people on the platform. On the other hand, there are a ton of sub -stackers today. Some of them are, like, in my opinion, some of the very best sub -stackers who are selling sponsorships. And I think there's a version of unlocking, you know, more economic, more economic opportunity, more economic upside that is aligned with the idea of independence, the idea of having differentiated value and quality. And so we're very interested in doing that.

22:17But my belief is we have to take a first principles approach and not just stuff adds in a thing, but ask the question, what would the good version of this be and help build that? Yeah, I think the bear case for ads has been sort of you know, dumb it down content or sort of, you know, click, clickbait for the masses. The bull case has been sort of allows, you know, niche writers to monetize without charging their audience a ton or it doesn't fall succumb, it doesn't succumb to audience capture in the same way that a subscription could basically there are pros and cons with both business models and you guys have to figure out how to integrate it in a way that works for the reader and the writer.

23:04I think the same is true of all of this magical AI technology that's coming online. I mean, we're building a live product that basically feels like, you know, I do a, feels like doing a FaceTime call and then magically turns into a highly produced podcast and a YouTube video and a series of short form clips and a transcript and pretty soon it's going to be in whatever language you want. And we just, we're going to live in a world where, you know, one thing you could have is you could have a bunch of like AI slop that kind of keeps has done people clicking, the other thing you could have is you could have a future where there's way more creative leverage and where the people who are making this independent stuff who have the independent voice can do way more, can make something much better, can realize their vision much more fully.

23:48And so in all these things, I'm kind of, you know, I think you look at the technology not as good or bad, you look at it as a powerful means to an end. And if you pick the right ends, then applying the technologies is very exciting. This is something I think you were so early to understand that is sort of common knowledge now or becoming more common knowledge but wasn't five years ago, which is that everyone can be a creator and we don't have enough content. Like I think there's this horrible meme, like we have podcasts are over, we have too much content, there's too much online and it's like actually it's the opposite.

24:22If you look at any of the four U feeds, I think most of it is now AI Slough, which says that there's just a dearth of extraordinary content. And what I always thought was so brilliant about what you understood about professional writers and having been a professional writer, it was almost like you were inside my psyche. The hardest part about writing is writing. Like it's really, really hard to get started writing if you're like a true writer and you're a writer's block. And so everything you can do to make the production of that writing easier, everything you can do to sort of create the flywheel where your readers are expecting something, your artificially creating deadlines, if you can create something very quickly that turns into a host of different products that then gives you the positive feedback loop that you need to keep doing it.

25:04Like there was something about from the very beginning, you really understood sort of the artist's way or the writer's drama of just how difficult it is to be a creator. And that exists within everyone, right? Like it's like none of us are, you know, none of us are day jobs are not writing, right? But all of us are writers, all of us are creators on this pod. And so there's something about if you can make people's lives much easier and make the creation loop easier, people who have day jobs will then do it and create magical, great content to rival the terrible content that now is being produced by these meme farms.