Big Technology Podcast - Newsletters and The Culture Wars — With Substack CEO Chris Best

Episode Date: July 14, 2021

Chris Best is the CEO of Substack, an email newsletter platform that lets writers send newsletters and charge subscribers a monthly fee. The platform — which I use for my Big Technology newsletter ��� is squarely in the middle of the battle over online speech, looked at by some as an alternative that will displace professional media. Best joins Big Technology Podcast to discuss his company's position in these speech battles, how he personally feels about the professional media, his investor Andressen Horowitz, and whether paid subscriptions are a better model than advertising. You can subscribe to my Big Technology Newsletter here: https://bigtechnology.substack.com/ The OneZero story https://onezero.medium.com/the-moderation-war-is-coming-to-spotify-substack-and-clubhouse-9fe00672091b

Hello and welcome to the big technology podcast, a show for cool-headed, nuanced conversation of the tech world and beyond. Our guest today is Chris Best. He is the CEO of Substack, an email newsletter platform that lets writers send newsletters and charge subscribers a monthly fee to get them. My big technology newsletter is on Substack, though I don't charge a fee yet, which I'm sure we'll discuss. Substack is also smack in the middle of the culture war, and so we'll have plenty to chat about there as well. Chris Best, welcome to the show. Thanks for having me. The last time we spoke, actually with voices, not emails, was in your apartment, I believe, in the mission in San Francisco. Was that?

That was your home. Yes. It was also substack HQ at the time. Right. And it's one of these like real Silicon Valley stories. Like we met there two years ago in 2019. You guys, you were three guys basically around a couple of computers. And fast forward two years later, you're a 650 million dollar company raised a ton of cash. I've left the job that I was working at to report on you guys when I was reporting on you guys, which was at BuzzFeed News. and have now built my career essentially on your platform and doing this podcast. And you're the biggest media story in the world, pretty much. It's just one of these wild things in Silicon Valley where, like, you know, in a couple of years, everything changes. How does it feel on your end? It's been an interesting couple of years. When we met that time, did you have, I mean, every entrepreneur has optimism.

But again, you were three guys. And there was like a handful of people using you, starting to make, some decent money, which is what my story was about. But did you have any sense of the scale that this thing was going to get at? Like, if I would have told you then, you'll be valued at $650 million a few years down the road. Would that have surprised you? Don't tell me you expected that completely. I don't know if we expected it, but this is kind of what we're aiming for, I think. Yeah. Like we sort of had it early on in subsect history, before I even moved to California, we kind of had a moment where Hamish and I were talking and were like, hey.

Hamish is your co-founder. Oh, my co-founder. One of my co-founder is Haymish. I knew beforehand, yeah, and brought me into your office, yeah. And we sort of had this moment, like, are we going to apply to YC? Are we going to try and do this? Are we going to try and play the, what YC is a startup accelerator? You know, are we going to kind of play this game?

What is the, what is the scope of our ambition here? Are we building like a cool little thing, or is it something that we think could actually be transformative. And to me, the reason to work on it, the reason it's exciting to me is because I do think it has at least the potential to be transformative, which is a far cry from saying that it's a sure thing, and I expected it and all that stuff. But I think this is the reason why it's worth working on to me is it does feel like it's something genuinely important for the world.

Yeah. Well, I think it's still unsettled, unsettled, in terms of what substacks impact on the world is going to be. And I think as you've grown in size, there's been a lot of scrutiny. Now you're competing with Twitter and Facebook, among others. So we'll get into all that as we go through this conversation. Let's start here. You on March 11th had this one tweet that went kind of viral and you've deleted it since.

Four words. Do you remember them? I think so. Refresh my memory. Defund the thought police. Yes. I saw you tweet that and thought that that was a fairly striking and aggressive thing from someone who is operating, you know, a company that likes to talk of itself as a neutral email platform. So I wanted to start there because it was so intriguing to me. It got retweeted over a thousand times. What did you mean by defund the thought police? Yeah, that was an interesting, interesting experience for me. I set my tweets to be deleted automatically after. period of time. So I think all of my tweets are deleted at this point. Okay. Um, you have a few

up there. Do I? Still. Yeah. You're welcoming Antonio Garcia Martinez, uh, to the platform. Okay. Yeah. I think they get, they get automatically deleted after a month or two or so. Okay. There's some fixed period of time. Yeah. All right. So you stand by the tweet. Yeah. I mean, I, and I, in the sense of kind of like, it was something I kind of like wrote in an offhand way as I was as I was kind of like thinking about all of the ways that people seem to want to sort of flex censorship muscles on the internet and think that it's like this this righteous crusade to try to kind of shut down other people's speech and other people's ideas. That's something that I've always kind of been kind of constitutionally against I guess.

It feels like the wrong approach. to me. And I tweeted what I think is certainly a a flippant formulation of that. Just kind of offhand without really thinking deeply about it. And it got, you know, as you say, it kind of went viral and travel the world. And some people were delighted by it. And some people hated it. And I was a genius or I was this evil. Look at this villain. And I kind of had this realization. I was like, oh my God, this is what it's like to like win on Twitter. Like this is what success on Twitter looks like is like having this stupidest possible thing. I was like, man, if this is the game, if this is what winning this game is, I do not need to play this game.

It's a sort of like a play stupid games win stupid prizes kind of idea. I think the place that we've put, we've put down our thoughts on this in an actual consistent, cool-headed way. We wrote a post on the substack blog kind of outlining our philosophy on content moderation, why we think freedom of the press is important, as important as ever, maybe more important in the age of the internet and all these platforms. And I think that would be the thing that I would point to and want to stand behind. I think it struck a chord because, and I wrote a story for one zero, basically predicting that this was going to happen, that you would be caught in the middle of the speech wars

along with Clubhouse and Spotify. And I felt that it struck a nerve because there were journalists that were starting to beat the drum of largely journalists. Maybe there were other Twitter users. I'm curious what your take is. I started to beat the drum of substack needs to have a coherent content moderation policy. Some people thought it needs to take certain newsletters down. Other people were upset at you for funding some newsletter. through your Substack Pro program where you give newsletter writers in advance and they have to

earn that out and they'll make a percentage above it, but essentially it's you funding them for a year or so. And people like that because it was some sort of repudiation to some of the reporters, I think, who were talking. And I will say tech media has spoken a lot about the need to moderate content on tech platforms and there's a backlash to it. And I thought that the people that loved that tweet said, Chris is sticking it to those reporters. And the people that didn't like that tweet said, this guy is running one of the more important media tech platforms in the world right now and is falling on one side of this and basically putting a thumb in the eye of a lot of people who've put some thought into the way the internet should operate. What do you think

about that. Yeah, I think that might be a fair, that might be a fair assessment. And I do think that in general, the way that tweets become successful is they kind of, if they maximally piss off both sides, if it's kind of like the worst, the worst possible thing is always the thing that is most successful. You mentioned something, you mentioned something earlier, you said substack sees itself as a neutral platform. And one of the things that I wrote in that, in that, that we wrote in that, in that our philosophy of content moderation essay is that we don't actually see ourselves as a neutral platform. We have a point of view. And our point of view is basically that freedom of the press is important, that giving people a place to express themselves,

letting readers and writers, writers and readers be in charge of what they're seeing is actually a really important principle. And we don't think that that is a neutral position. It's certainly not a universal position. There are lots of people in the world who think that it's really important that every platform take a, you know, a, what's a fair way to put this, a strong approach to moderating and kicking off people that have the wrong ideas or that express things the wrong way. And we just fundamentally don't believe that. You want to defund the stop police. Yeah, I mean, there's a real impulse in the culture. And I think it comes from a, it doesn't come from no reason. It's not people that are, there is a real problem there. My diet.

diagnosis of this is the first generation of these internet media companies, the social media companies created a like a crazy machine. They created a machine that rewards engagement and therefore rewards like rage and hate and awful things. And so they kind of created a machine that inexorably pulls in an awful direction. And then the answer is like, well, once things get inevitably, once the awful things start to crop up, we have to like, swat them down and if not this thing's going to this thing's going to fall over and i just think that's like that's not a solution like we had one problem and now we're introducing heavy-handed censorship which is really impossible to do well and now you just have two problems and the real solution is

is to play a different game entirely i think there's a real problem the instant comes from a reasonable place but i do think that my position and the and substacks position is that freedom of the press is important and that heavy-handed censorship is not the not the right solution. Okay, Chris, but look, some people are going to look at Substack as this tool that's going to replace the professional media, which they say is, you know, obscuring the truth with new judgment on one hand and content moderation advocacy on the other. And, you know, there are legitimate complaints about what the professional media wants to cover or doesn't want to cover. But I think what many of the people, the powerful people that are advancing these

arguments want is less accountability. You know, don't look into the stuff we want hidden. And to get that, you just discredit the professional press as an institution. So when they see you say defund the thought police, they're thrilled because here's a step as an alternative. And to the professional media, they can be less accountable that way. So, Chris, I want to know how do you balance your platform's role as like a calmer alternative to social media fueled writing and news while also not playing into the hands of these people who want to crush the press because they only want to see positive headlines and live

accountability free. No, I think that's a great question. I mean, the way that I think of this, I think ultimately the thing that we're setting up, that we are sitting up to disrupt and to change with Substack is not the professional media, is not legacy journalism, anything like that. I really do think it is the attention economy writ large. Like the thing that Substack is at the core to me is as a writer, it's a place where I can go independent. I can, you know, have this model where I try to earn and keep the trust of my readership, which means, that not only, you know, it's not just a different way to make money, but it's, you can do a different and better kind of work. This is why you should charge instead of having ads, by the way. Yeah, we're going to talk about that second half for sure. Yeah. And for readers, it's a, I think of it as a place to take back your mind, right? People have this growing sense of like, oh, my God, the media diet I have is driving me slowly insane. And it's, some of that comes from the professional media, but it's really the root cause of it is, is the feeds, is the social media algorithms.

They're calling the shots. That's determining what wins. Yeah. And people just it's compelling. I'm choosing it, but I'm sort of, I have this uneasy sense of, like, my mind is, is going to rot and it's breaking the brain. So I think that is ultimately what what Substack exists to do. There are certainly people out there who kind of look at the, the manifold problems of the professional media and kind of take this approach of like, institutions are awful, they shouldn't exist, burn it to the ground and do something new. It's a very popular ideology right now. And they look to Substack as one of the ways. to do that.

Yeah. I mean, for what it's worth, I'm not one of those people. I don't think that that, I don't think that the answer, you know, to the extent that you have institutions that have problems, the answer is not burn them to the ground and start over. I think that's a false, a fault, like a mirage of a solution. It kind of feels emotionally satisfying, but it's a kind of thing that when you try to do it in practice is catastrophic.

I do think that, as you mentioned, having these institutions is really important. Right. Society can't function unless we have a working professional press, whether it exists in the legacy format, or whether it exists on subsect, whether it exists in something totally different, that matters deeply. And so I kind of think that, you know, the thing that's worthwhile doing is trying to make institutions better. And I think the two ways that you can do that are you can sort of provide actual a vehicle for actual real critique, right? So if institutions get to a place where there's a mode of groupthink where no one's really kind of like asking the hard questions and and making the strong case, it can kind of like lead things off the rails where even an institution that starts very good can kind of like descend into into madness. So having in the case of the press asking some hard questions and not others. Yeah, exactly. And there's exactly. like there's some things that you're you're supposed to like you're allowed to be super critical of and other things that are that are sacred and we can't kind of question the thinking on this or that

I think providing a space where all of it can be questioned is is valuable in itself because it provides you know even when the questioning is wrong it provides kind of like a corrective pressure to sharpen thinking and to have to actually like be accountable to doing the right thing and the other thing that you can do is before you go to the second not to mention heterorthodox thinking is courted your business's success because if I'm out here saying the same thing that every other tech publication is saying, I'm not making a business on that. No one's going to subscribe. And I'm not, I wouldn't classify myself as like a traditional heterorthodox thinker. I might have a little, some different perspectives on the stuff. But like it does seem like a platform like

yours will lend itself to the heterothodox where people will subscribe to stuff they can't get anywhere else. Yeah. I think, I think where people will subscribe to stuff they can't get anywhere else is absolutely right. And some of that could mean people who disagree with the things that you get everyone else. And some could be things that are just, there's not covered. Like, they don't exist, right? Emily Atkins newsletter is a perfect example of that. She writes Heated, which is a climate change focus newsletter for listeners.

Yeah, sorry, go ahead. Yeah, you should subscribe to, I think it's Heated.World. It's a good one. And there's lots of examples like this. There's people that are covering industries that are like, there's just nobody covers my industry well. everybody I know wants to have something. And so I'm going to go and do it myself. I know the industry well.

I'm going to be able to do a good job of it. And then all of a sudden there's this thing that people find valuable. So I think that is absolutely true. The other, back to the institution question. So provide, you know, sharp critique that sharpens the thinking makes things better. The other is provide a place where new institutions can begin. So institutions are long lived, but they don't live, they don't always live forever. And sometimes you need some renewal.

And so I think providing a place where if there is a new way needed, people can try it and find it and create something. And I think there are a bunch of publications on Substack that are making a real stab at creating something new and lasting. So I just want to go back to what we were talking about earlier when it comes to what role this platform is playing. Because I understand that you want it to be this like sort of counterpoint to social media. But you must be aware that it's become this very important place in the culture war, especially, you know, the culture war that's being fought over the future of the media, which is a big part of the broader culture war. So you're not going to deny that part, right? Like, even though you like to, you know, go to this point about social media, obviously, you know, I don't know, it does seem like it's playing a role in this culture war. And it is being looked at by people as a way to burn down institutions.

I mean, I read the tweets, man. That's what people are saying. That's your first, that's your first mistake. If you would just stop reading the tweets, you'd be so much happier. That's true. No, to me this is all of a piece. Stop sending the tweets. It might be even better.

But sorry, go ahead. Both, both ideal. To me, this is all of a piece. And it's not, I don't think of this as kind of like we, we, you know, set out naively and wanting to just do some cool thing and accidentally ended up in the heat of the culture wars like we knew when we started substack like this is what we're doing and to me that you know this my thesis here is this crazy brain caused by social media is the thing that is making the culture wars be the way they are and manifest the way they do and is causing some of the shifts in in how that

stuff works and so we were running towards the fire when we started substack like we knew that was going to happen yeah so I can't very well complain now that that's the case and I would just rather be doing something that I think is positive rather than just avoiding it and thinking, oh, gosh, I hope this gets better on its own. Yeah, look, I happen to think it's positive overall. I like the fact that this exists. I think it's allowed me to explore new areas of my journalism. I don't think I would have gotten elsewhere.

And so I appreciate that, even though I'm not, you know, running straight in line with your business model. But I think it is it is overall good. I just do wonder, again, like, we're in a moment we're trusted institutions is at an all-time low. And as part of that, the institution's fault, yes. But as part of that also a campaign to discredit institutions by the powerful, heck yes. And I also wonder about your investor.

You're invested in heavily by Andreessen Horowitz. They're your lead investor. I mean, it's not a stretch to say that they have a real disdain for the tech press. and Mark Andreessen's you know blocked about every journalist I know he's blocked me I don't mind but you know again like it's kind of hilarious to me that like you know I hear the corporate media is the problem but now I'm hearing independent media might be the problem and is it really the media is the problem or again is it accountability because I do know that Andreessen Horowitz has had a number of investments that have let's take the Xenifits for example the HR benefits company that was doing a number of things that were extremely sketchy and were exposed by one of my colleagues, Will Alden at BuzzFeed News. I was a black guy for entries in which were pushing them to grow faster than they should of, which is a core component to a lot of VC business models.

And so, of course, they're going to, you know, despise the media, even though, the professional media, even though, like, of course they're going to get something, they're going to get things wrong, but it's also like, well, you know, maybe accountability is part of it too. So again, like, and this is kind of a funny thing for me to ask because I'm a journalist for sure. And I'm on your platform that, again, is funded by these folks who don't have a high opinion of journalists, at least from what I can tell. So how do you think about that? And how has their thinking about the practice of journalism influenced you in terms of the way that you run your platform? I certainly can't speak for them other than to say that they've been pretty great

partners for us and you know in terms of building a business and all that stuff it's been it's been actually very valuable for us well they did give you a lot of money the money helps to you can't complain yeah i don't know i guess a lot of this depends on you know okay so we all agree that there's the the media is not perfect there's some degree of problem with it people are dissatisfied with it to some extent how much of that is should they be looking inwards and how much of it is is you know, a campaign to discredit. A little both, I would say. I think you could, yeah, you can, you can sort of like argue it until the cows come home.

I think the question is, given that you're in that state, what's the way forward? Right. If we need trusted press and trusted institutions to have a cogent society, and we don't have that, what's the best thing that? What's the, what's the, what's, how do we get from here to there? To me, that's the more interesting question. And I don't think, and this is a straw. And I'm not saying this is what you're saying, but the answer of like, well, people should

just trust the media more and we shouldn't talk badly about them, even if they're bad. Not what I'm saying. It's not going to work. I think there should be competition. I also wonder about the motivations of the people that are funding this thing. And I wonder if you do as well. I can speak to my motivations. And my motivation with this is to build something new and better that provides a real

alternative for writers and for readers. And I think that there are a bunch of people on Substack who, you know, have the opportunity to do the work now that they think they've always wanted to do and weren't able to in the old system. And to me, that's just a big win. Yeah. Yeah, it's such a funny position for me to be in also. Like, it's actually really good and cathartic to have this conversation with you because I understand that it's a complicated platform to be on. But also, I think it's great. You know? It's like, I really like getting this opportunity to go one to one with an audience, you know, me emailing them once a week and getting replies and understanding that there's

going to be a built-in audience. So I, like, by default, do not need a sensationalize anything to get readers is amazing and liberating. And I think it's the way that it should be. So I like it. And maybe, you know, I think one of the interesting things we've seen, and since you guys had your rise is that every publication seems to be, you know, going all in on newsletters now. You have Bloomberg. It seems Bloomberg has every reporter doing a newsletter now. The

information just launched a new vertical. It's a newsletter. Everyone's asking, what's your newsletter strategy? Puck is another one that's sort of launching in stealth now. Oh, God, I'm probably going to get in trouble for saying that. But their newsletters are out there. But it's basically like a new publication where they're going to try to get people to pay for newsletters. So I agree that it's much healthier than trying to write for the social feeds. So we have common ground there for sure. Yeah. And I think there's two parts of that, right? There's the built-in audience. Well, this is where we're going to differ, actually. There's the built-in audience where it's, you know, people have earned their trust enough. They've invited

me to their inbox. And so if I want to write something that's not super clicky, but I think is important. I can send it. They'll get it. And the other part of it is actually having a way to get paid directly. The independence is the key. And having the audience is half of that. And then having the direct subscription, I think, is the other half. Yeah, I don't think we really disagree, honestly, because so there's two types of currency that you can get from writing a newsletter. One is somebody agreeing to open it every week and not unsubscribe. And the other is someone willing to pay. And it's just the same thing. It's just, you know, one step of loyalty higher.

But I know, like, when I write for someone, I am not writing for them, you know, to share it on Twitter and blow up and outrage people. I'm writing to say, thank you for giving me a spot in your inbox. I'm going to try to provide value. And hopefully, if I do that, you'll be back next week. And then eventually, you know, the idea is maybe turn on subscriptions, but not yet. Okay, so we have Twitter and Facebook are getting in this game too, which is interesting because all the incentives of social media are opposite of that. They are essentially outrage, write things that are shared like crazy.

Let's talk about that after the break. We'll be back here in the Big Technology podcast right after this with Substack CEO Chris Best. Hey, everyone, let me tell you about the Hustle Daily Show, a podcast filled with business, tech news, and original stories to keep you in the loop. on what's trending. More than 2 million professionals read The Hustle's daily email for its irreverent and informative takes on business and tech news. Now, they have a daily podcast called The Hustle Daily Show, where their team of writers break down the biggest business headlines in 15 minutes or less and explain why you should care about them. So, search for the Hustle Daily

show and your favorite podcast app, like the one you're using right now. And we're back here on the big technology podcast with Chris Best. Yes, I met him. in an apartment, right around the corner from my old apartment, actually, in San Francisco and had no idea that substack would get this big. But I did find that reporters were from our conversation making real money, and maybe that sparked the initial desire for me to go and do it on my own. And my has it grown. So before the break, we were talking a little bit about the incentive for writing that comes to your inbox, for a writer, the incentive for a writer that writes to a paid subscriber or even a free subscriber going to their inbox

versus social media. Now, Facebook and Twitter are getting in this game, Twitter with review. Facebook just launched its own newsletter copycat called Bulletin. And Bulletin has like some very big name writers, including Malcolm Gladwell. And who's the guy that wrote Tuesdays with Mori, Mitch Album, he's on there too, some others. Oh, and yeah, anyway, we can go forever. So, but it's also a little bit weird because those of us who've been doing this for a while, the newsletter writers, we did this because we wanted to get away from the social media algorithms, not run towards them. And Facebook's pitch and Twitter's pitch, I'm sure is, hey, we have the distribution for you. And so do the same thing you've been doing forever. Just, you know,

use our platform and everything will work out. how strange is it to see them get in the game for you? And what do you think your competitive advantage is going to be? Because at the end of the day, you know, your software is good. I'll say it's the best newsletter platform I've used. I have some complaints, but overall, very good. And but you're still going against a, you know, a 200 million daily active user platform and then a 2.5 or close to 3 billion user platform in Facebook.

So, yeah, what's your reaction? And then how do you win? Yeah. I mean, and these are massive companies. They have all the resources, all the people. My reaction, you know, we talked about, did I expect this? I expect Substack to be where it is. I think I'd always hoped that Substack would be where it is.

I'd always thought that we were onto something that this new model could really work and could really create a new path for, you know, writers and readers on the Internet. And I think we're in the place in Substack's history where it is working. It's clearly working. it's clearly growing. There's hundreds of thousands of paying subscribers. There's people that are making all this money. And I think that you just, you don't get to be one of the great companies and change the world without Facebook and Twitter copying you along the way. And so while it's scary to have a giant company, you know, clone your product, which is both flattering, but also scary.

I do think this is like clone clone. Like on mobile view, you can't tell the difference. It was very brazen. It's pretty, it's, it was very flattering. I could think of some other words to use. But, okay. It's brazen and fra. I mean, this is, this is, this is what happens. That's how it goes. Yeah. And I think it just, again, I just see this as evidence of like the, this model is working and this is the future. And they are seeing people, as you say, leave the ecosystem and choose something better and it's freaking them out. And, you know, I do think that they're, you know, they're building a credible effort at it because they've chosen to be inspired by some good sources. I think the thing that I would point to for Twitter and Facebook is really just the

core of what the core of what Substack is, is this new model. It is a departure away from the incentive game. It is true independence for writers where you own your list, you own your relationships. You know, you can always reach your people and you do sort of have this direct relationship. And for readers, it's this idea that like you want to take back your mind. You want to stop spending all of your time getting sucked into these engagement machines. I just don't think that that Twitter and Facebook can ever fully offer that. It's kind of like oil companies building like a solar thing. It's laudable.

It's nice, but they're not going to like shut the pumps down. You've said take back your mind a couple of times. Do you think that using, I mean, reading email newsletters and using social media are mutually exclusive? Because I'll be honest, I get a lot of links from Twitter. I get a lot of links when they come into my inbox from substacks. So what is this that you're talking about? Yeah, I don't think they're mutually exclusive at all.

But I do think, like, to me, the zoomed out version of this is people used to get bored. People used to have this time where it's like, I have nothing to do. And I don't know. I need something to entertain me. And then the internet came along. And then smartphones came along and social media came along. And now we've kind of like built these engagement machines that are designed to kind of like suck up. every moment of your life that it can possibly get their hands on to serve you advertising.

And then as a person who's a user of one of these things, all of your life is getting sucked up by it. And your finite resource is not your money, it's your attention. You only have so long to live. You have only so much energy to spend reading things. And if you give all of your attention to this feed that's kind of working against you, it is kind of taking over your mind. And I think people are increasingly realizing this and feeling this, you know, the fact that we've invented terminology like hate reading and doom scrolling is a pretty good tell that people feel that something is wrong. And to me, the answer is not going to be like, well, stop reading things on your phone or like, don't just whatever, give up on this and eat your vegetables instead.

I think the right answer is give people a real alternative, a different way to connect with the writers they trust with the culture at large, with the ideas they care about that's just not governed by the same underlying rules. That's not trying to maximize their engagement, but is instead trying to like earn and keep their trust to the point where they'll spend the money. And so to me, it's like if people just at least some of the time instead of clicking on Twitter, go to their, go read their substack stuff, they're kind of using that reading time more intentionally in a way that is better for their life. Here's my perspective. I, you know, having done this for a while,

I think that, you know, it's really interesting to hear you frame this from the perspective of the reader or the consumer. I honestly think that it's more compelling

to frame it from the perspective of the creator where the incentives that your platform creates write to the email, again, built-in audience. You don't have to worry

about getting retweets to have people read your stuff. Therefore, you're going to be less predisposed to write for the incentives that these platforms have. And the way to get

retweets and they're ready to get shares on Facebook is to write for outrage and is to write to confirmation bias. And if you have these people, and that's why, you know, you said earlier in the second half of the last half of the first segment that, you know, we're going to disagree. We agree. I think 100% on this. When you move that relationship from I need to stoke outrage or I need to say something dramatic or radical in order to get readers to, hey, I'm going to write the best thing I can.

and it's going to land in people's inboxes. Yeah. And I don't need to worry about ramping it up because they trust me to tell them the truth. And they're going to share it when they see me doing that, you know, versus the other way around. That changes the game. And then the second order effect is it changes the consumer experience. Yeah. That's exactly right.

It's not just a different way to make money doing the same thing. It's when you're doing it this way, the kind of work you do is qualitatively different and better. And that readers appreciate that. And actually, I think that's exactly right as well. I see that writer framing and the reader framing of take your back your mind as two halves of the same coin. Right. Right.

One only works because the other works. Right. If we gave you this great way to go independent and a tool to send emails and nobody cared and nobody was hungry for a different experience, it wouldn't work. You wouldn't have readers that were clamoring for this thing. But what happens is, yeah, you get the better incentives. You can do the work that actually matters. And readers recognize it.

and it turns out are hungry for it because they want to take back their mind and because they want something better. Is it weird for you that, sorry to keep going back to Andresen Horowitz, but there's such an interesting player in this drama. Is it weird for you that they're, you know, your funder, I imagine on your board and also on Facebook's board? And then the same thing happens with Clubhouse, right? Like Mark Andreessen works hard to build a Clubhouse up.

Mark Zuckerberg comes and participates the next thing you know. Clubhouse has cloned one-to-one on Facebook. Is that strange for you at all? It's not that strange, I guess. You're being very kind to them. I understand why. Yeah, I mean, do you want me to trash them? Is that the...

No, I want you to be honest. I think it's going to sound, it's going to sound sort of puffy and ridiculous. Like, we've had a really fantastic experience with them. I mean, the fact that they're, this is the firm that's helped build some of the world's great companies gives that the, that the person. perspective, they bring extra value. I think there's a lot of this, I think there is a lot of like general skepticism towards them that that's unfair and unwarranted in my estimation.

Well, that's, that's, I think that's where we disagree. So, but, but, but, you know, again, V.C. is complicated. I get it. Without VC, we wouldn't have some of our great companies and their engine of growth. But. There's other incentives there. So anyway, you've taken enough income on Andrewsson Horowitz. I'll leave you alone at this point. All right.

Let's take another break. I want to talk to you a little bit more about the technology of Substack, what this evolves into, and then maybe you can convince me to move from advertising to subscription. How does that sound? Yes, yes. Okay. Finally. All right.

We'll be back here on the big technology podcast for one final segment with Chris Best. He's the CEO of Substack. Okay. And we're back here for one final segment on the big technology podcast with Chris Best, CEO of Substack. Well, we've really gotten into it in the first two segments. Chris, I appreciate you rolling with it. So I want to talk to you a little bit about the technology side of your platform.

Let me just go with my first big question, which is that there's so many email newsletters now. And I wonder what this evolves into because is it going to just end up to an email inbox being a thing you do to complete. tasks kind of and then most of the time read stuff or do we just end up in the day you know back in the days of the rs s reader where you subscribe to certain feeds and they end up in your reader and i know substack has built a reader of its own and i've used it and i also know that like my gmail at this point the promotions tab is is strange it's gone from you know five percent off coupons for the gap to uh just a stream of different newsletters coming in from substack and it does really feel like an RSS read. Sounds like a major improvement to me.

Well, it depends on the day. It depends who's writing. If Casey Newton's writing, no, I'm kidding. His newsletter's great. So what do you think? I mean, and I should say that we do support RSS on substack. So each substack that is a newsletter is also an RSS feed. I think you mentioned this with podcasting. I think the magic of email is that it's the last, one of the last places where you can have a direct relationship with somebody specifically on a phone and mobile, right? Like when we switch from desktop to phones, the idea of browsing the web kind of mostly went away. People used to sit down and type in their favorite websites and that was kind of you would surf the web. People do that in mobile a little bit, but not nearly as much. And so the real thing

is you need to be on the home stream. You need to have a little blue dot in order to really have a relationship with somebody in mobile on their phone where they're doing a lot of reading. And it turns out that you're not going to make an app per new thing. And one of the few apps where you can have a direct relationship that people already have and they don't have to get a new app is their email inbox because you can send them an email. They'll get an notification. They'll click in and they'll read it. Another one of those, by the way, is their podcast player. Right? And the podcast player works. That's why we're here. You have this direct connection. This podcast showed up in your thing. You went to the app. You thought, oh, that sounds nice. And there I go. And so I think the magic is not

necessarily email per se, but it is that direct connection unmediated by kind of the attention algorithm where people opt into following you and you can push them something onto their home screen. Like, that's the magic. Not fully unmediated because we still go through. I know we've talked the whole time about there are no algorithms. Yeah, because you wrote in your last post, for writers, this means being, and you're talking about email versus social media, back to this again. For writers, this means being able to control their relationships with their audience. instead of being mediated by fickle corporations whose algorithms decide what gets the most attention.

And I'm like, I like that in theory. But Gmail, man. Yeah, Gmail will. You have the primary inbox. You have promotions and you have spam. And, you know, this deliverability stuff is a real. Make sure you drag the big technology newsletter into your primary inbox. It will help the whole world.

I'm working on it. I'm working on it. So, but yeah, I think that, but it is. the closest as close as you can get to a pure experience which is interesting the okay tech question number two um the the platforms you're competing against really good at um helping publications get discovered that's what their pitch is against you guys are you guys going to build in any discovery where like you know i'm interested in substacks like i can do a better job browsing there have been even hacks of your website that people have built that tries to show folks you know what news

they might want to subscribe to, or are you going to leave it largely on the newsletter writer? I think the way that people in the industry talk about this is, are you going to be a Shopify for newsletter writers, basically, you know, give them the tools and they go create and promote, et cetera, et cetera. You're just the bare bones technology. Are you going to be in Amazon where, like, you're going to end up drawing the interest and then be this crucial place for people to get discovered? What's your thought on that part?

Yeah, I do think that discovery is one of the most important things we can bring to writers, right? The things that you want lots of features, but the thing that you really care about is, like, are people finding and falling love in love with my work? And for readers, too, like if, you know, if I already know a specific writer I love, that's great, but then finding the next one is really important. So I think it's both we do some of this now, I think more than people expect we're driving subscriptions for newsletters. and I do think it's a big area of opportunity for us. Yeah, there's the homepage. We have a few features that do this. And a lot of this happens.

There's a lot of sort of cross-discovery as well that happens organically. People link to each other. People put each other in their blog rules. They do cross posts and guest posts, things like this. So I think it is a major area that we can do a lot of good in. I think the trick is doing it in a way that doesn't, again, recreate the problems that we sought to avoid, right? You don't want to have a, you know, a discovery thing that ends up being gamable in some way that drives bad behavior, which is why I like revenue ranked leaderboards.

It's kind of like, hey, if you want to game this, go ahead, like try to get enough people to subscribe. Like, that's kind of the, that's the right game to be playing. Right. Speaking of leaderboards, it's a great segue, Chris. You just handed it to me perfectly. Are you afraid your top earning writers are going to leave? Because the chatter is, oh, this is a, very expensive email platform. They pay 10% of all email subscriptions to you and then another 3% I suppose to Stripe. So, you know, once you get into a decent enough tier, you know, you're paying that to you guys. Then there's, you know, obviously the government and all that stuff. And then what's a creator walking away with? Thank goodness we're not paying Apple also.

But there are, you know, there are alternatives. There's Twitter's going to be 5%. Facebook's going to be free. So how are you going to target that? Maybe you give benefits. Maybe you lower that rate. Do you want to break some news here about how you're going to lower the rate at some point? What's your thought? Yeah. And what's more, one of the key promises of substack is that you can leave. Right. We're not trying to lock you in, you know, that we think this is your thing, right? You have your email list. You have your payment relationships. We really, I think of this as us kind of burning the boats to say, like, we're not going to force you to stay. And the only way that, we're going to get you to stay is by delivering enough value that it makes sense for you to

stay. And the main ways that we can deliver value are by like handling all of the things outside of the writing and just making it automatically great. And this is especially important early on, like our pitch, the very early pitch I made to some of the writers and stuff like maybe to you too was we'll do everything for you except the hard part. Like if you do the writing, the platform's kind of going to take care of the rest. And that means having the software work, that means having support handled for you. That means, you know, a bunch of services that we're introducing along, like, help you find an editor, help you get your legal fees.

Like, how do I do my design? Like, we sort of have like a whole suite of things that provide everything that you need. Right. And then the other, of course, is just growing faster because, you know, 10% is a fixed amount. But at the end of the day, if my, if you're bending my growth rate over time, that actually becomes much more meaningful than any, like, fixed point fee. And so the features that Substack builds that lets you grow, row both sort of organically as people share, as people pass it around, as people link to each other,

and through the platform where we're bringing you readers and we can say, hey, look over here, here's a bunch of people who only came because of the power of the substack network. You know, if we can say, yeah, we're taking 10%, but here we brought you 20%. That just changes the game entirely. Yeah. No, I think it's, I'll say from my perspective, platform rules, because I don't have to pay anything for it, whereas I would with others. But again, I'm ad supported.

So once I turn on subscriptions, I'm paying you guys 10%, which look, I wouldn't mind. We're going to, we're going to, sorry, go ahead, Chris. Yeah. I love that you know that you're going to turn on subscriptions and we're just arguing over when you should. Yeah. Well, let's talk about it because now we're into it. So I am going to turn on subscriptions. So my idea has always been this is not a one or two year thing.

So first of all, I want to say, you guys, let's talk about those services you offer. you've paid some writer's advances, you've given some writers' health care subsidies, done design, and legal for them. I haven't taken any of those except I had one of your lawyers look over my first story to make sure I didn't get sued, which I appreciate. So those are definitely enticing benefits once those come in. Okay, but like I said, both this podcast and my newsletter, I don't look at these in a time horizon of one or two years. This is what I want to be doing for the rest of my career. And so personally, my thought going free to start has been, let's, two things. One is, let's build the audience, right?

Make sure that these are free and accessible to everyone. And I don't end up having some of the distribution hampered by a paywall. And then two is, I'm going to be honest here. And I've talked about this, I think, on the show before. But I'm concerned about potentially burning out at some point, which happens to lots of creators where they create, or writers or whatever people are using these tools, use your buzzword. They create so much that they lose themselves in some way. And at a certain point, they look up for error.

They've promised paid subscribers that they would do three posts a week, and they find themselves physically unable to do one post a week because they've worked themselves so hard. So what I've always thought is, I can do this without. advertising. I know they add industry and build it to a point where two things happen. One is the audience is big enough where I feel okay putting some stuff behind a paywall. And then two, being able to maintain my mental sanity. And the thing about being on your own is you can just keep working and no one will tell you to stop. Yeah, especially if you're

in lockdown. Especially if you're in lockdown. So those are my perspective. But I do think that at the eventually the time will come to turn on these subscriptions. And I guess the timing, the timing question is what we'll talk about. Let me give me the pitch that I would give you if you were, if we were just talking about this, as what's right thing. Right. I think there's a, there's a misconception, and we thought this early on too, this idea that if I turn on paid, it's going to slow my growth, where it's like, you know, I just need to

get as many people as possible and then I'll turn on paid and then off I go. And we've just empirically seen over and over again. that doesn't happen. And in fact, a lot of the time when people turn on paid, their growth actually accelerates if they do it right. And the advice that we give people, by the way, in general on substack is when you have a paid thing, take your best and most accessible stuff, the thing that you think is, you know, change the world. You want the biggest reader. Make that free. And the inside baseball stuff, you can use the paid audience almost as like an audience of people that have really opted in to get your, you know, really care. And so if you got something

that's like, oh man, only the people that really love me would ever want to read this. I don't know if I want to send an email to everybody. You have kind of like the perfect audience to hit with that stuff to do like discussion things to spend time with, to get ideas for stuff. I think that model works really well. The advice I give people

now is don't turn on paid. Yeah. No. Oh, you go ahead. I'm actually kind of curious what your advice is now. My advice is is don't turn on paid until you have kind of like, you know, in a startup you would call product market fit where you've kind of figured out your editorial strategy where people are like people are continuing to open it week after week where it's kind of growing leadership. If you're in a place

where you're still kind of figuring out what the pitch of the thing is, then don't turn on paid because it just makes it locks you in, right? It keeps you, it keeps you, it makes it hard to be like, oh, actually, like I kind of want to take a different angle on this. Yeah. If you figured out the angle and it's working and you're just trying to grow it, I think you can turn on pain and I think it works really well. Yeah, I would say, so here's the answer to my counterpoint I was going to give. I think people do grow when they turn on paid because they send more emails. And that's, you know, we've talked to, well, not you and I, but some people will talk about how the data always tells you to send more emails. And so again, that goes to the second part of the thing. I'll do

it eventually. But I also think that advertising, so I actually started out in the ad industry, kind of disdainful of advertising. But I do think that advertising can play a really good role in supporting content. We've done two breaks in this conversation. No one was killed because of it, and it will help support the podcast. As far as I know, I don't know. If we did programmatic ads, I don't take any responsibility for what shut up there. I'll agree to disagree. I just hate, I hate podcast ads so much. I just, but you like podcasts, though. I like podcasts. I'm happy to, I'm happy to pay for them. Okay. Yeah. So that's another eventuality that could happen. And I think, I think the burnout thing is real. And I, the thing that I would, I suggest,

I'm a year, by the way, I'm a year plus into this. I feel energized. I'm going to take August off, you know, post-COVID, post-book type of recharge. The podcast, by the way, listeners, podcasts will go on. I'm going to record four and then we'll keep rolling it. But I will say, I've definitely spoken to people who've given up. You know, it's like podcasts, the most podcasts don't end up going to their third episode. I imagine you guys have, I'm kind of curious what your data is. Do most substack newsletters go to their third newsletter? It's like the classic, I think of this is in like the heyday of blogging. It's like, this is my new blog. It's awesome. I'm going to post here every week. Second post three months later. Oh, man, I haven't I haven't been doing it, but I'm really going to start now. No three posts. That's it. Most newsletters also, I mean, not most, but a lot of newsletters I've seen spend almost every edition writing to subscribers about why they haven't written. And I'm just like, okay, I get it. Just, you know, let's go to the videotape here of people. I think the thing you do is to set the expectation up front. Your readers don't want you to now they're not they're not sitting here being like if i don't get a million emails i'm going to be super disappointed you know you're paying for the signal not not the like you know overall

volume of content and if you say i'm going to take a healthy amount of breaks and that's part of how i'm going to serve you and if you pay like assume that i'm going to go on vacation that's totally fair people don't look people don't look at that and be like what do you mean you took two weeks off in the summer to do something like you monster it's fun it's a good thing to you and i I encourage it. I do think there are people who don't and it doesn't end up helping them in the long run. Right. You say, if you get burned out, you're not going to help anyone. Yeah, the keyboard becomes a very daunting thing to look at. Okay, you didn't really answer the question I asked about whether you were worried if some of your top earners will even do their own thing. Are you,

I know that you said our value proposition is that we can help them grow. But talk about your emotions, Chris. Let's let's get into this. Yeah. I mean, are you worried? Of course I'm worried. And this is kind of the, we've designed the business of Substack to put this pressure on ourselves, right? We make it explicit that people are allowed to leave any time. It's one of our core promises. It's your audience, right? We've got a fee that makes the business sustainable. If you're writing on Substack, you never have to wonder, like, oh, what is the business model?

Are they going to turn around sometime in the future and, like, do something? Do they, are their interests uncoupled from mine? No, we have a fee that aligns our interest. we want you to make way more money because then we make way more money and that you know that you know exactly how we're incentivized you know the same way that the reader gets aligned with the writer the we are aligned with with you know the writer gets aligned with substack we want you to win for all these reasons and i think it just puts the right pressure on us right it puts the pressure on us that we have to show that value that we have to show you you know here's all of the ways that we're helping you

and so i think it lights a fire under us as a company to make the platform that can keep the great writers, not because they're stuck, not because they're forced to use our weird payment infrastructure, but because it's just the best place to be. And I think actually, like, counterintuitively in the long run by like exposing ourselves in that, you know, being vulnerable in that way, it's actually like a jiu-jitsu move that helps. It's good. I agree. I think it's a good move. And it seems like it's working. You've had most of the people stay. It seems like your revenue is growing pretty well. So you don't have to raise again, do you? No.

You're in good shape. I think I'm going to, this has been a very inspiring conversation. I think I'm going to start a publication that's going to be all about the bad things that people are saying online and why they should be removed. And I'll call it the thought police and we'll do $5 a month. Yeah, we'll see, we'll see how many people, how many people get excited for that. You can tweet, fund the thought police. Good luck with it. I'm kidding. I'm not going to do that.

They wanted to ask, some people, wanted me to ask you about content moderation. You guys have talked about that ad nauseum. You're not tight. Do you have a head of policy now? Are you taking any newsletters down? I know there's been one that's been removed for some weird for like trying to point someone to a different payment service. But what's your situation on that? We take like thousands of newsletters down mostly because it's spam. Like the number one problem we have as people are like, yeah. I know. Yeah. I want to follow up. That will be the last question. But, sorry, go ahead. There's lots of problems.

It is a major area of the company. You know, I think the thing I would say, we cover this a little bit, but we wrote an in-depth blog post about our philosophy of cognitive moderation. The highlight of which is basically we believe strongly in the freedom of the press. We think that letting, putting writers and readers in charge of what they say is good. Even though there are tradeoffs, we think it's good, it's important, it's necessary for society. That's where we as a company come down. And, you know, we do acknowledge that some moderation is necessary. I don't think that we can say we're going to, like, cover our eyes and never look at anything.

I don't think that that works in practice. I don't think that's the way to actually further the ideals of a free press. But we do kind of, that is the position that we come from. We just care deeply about it. Great. So you're not going to take me down for doing ads and not subscription. Not unless you do that thought, police one. No, I'm just kidding.

That would be fine, of course. Okay, cool. All right. Last question for you. You're a free email service, sensibly, people are, you know, not doing ads. So you have lots of spam newsletters on there. And I imagine the email service providers are looking at substack as a domain and saying,

are these trustworthy newsletters, are they not? And regardless of the fact that you have some high quality folks and some spammers on here, on the platform, they will treat some of the domains the same and then start sending some of the good substack newsletters to spam. I know Casey Newton just tweeted that his dad couldn't find his newsletter. And he said, check your spam folder. And his dad said, I want a refund in a text message. And I've had friends saying, hey, Alex, what happened?

You took the last couple weeks off. And it turned out it was in their spam folders. So obviously, we talked about this a bunch already. And again, I'll conclude here. But deliverability, getting emails into inboxes is the most important thing an email platform can do, at least in my opinion. So how do you address that issue? Yeah. No, it's a hugely important issue for us, you say, and I actually think this is one of the great strengths of substack compared to some of the other more general email sending services that do a lot of email marketing. So putting aside spammers for a second, if you just have normal substack users that are sending emails to people, our support volume, by far there are more people saying, hey, I wanted this newsletter and I was really excited to read it and I was missing it. That the number of people that have

that problem, dwarfs the number of people who have the problem of like, geez, I got this thing and it was spam and it was annoying. Unfortunately, no email newsletter email service provider has this problem where you're sending a large volume of email that people actually really want and care about and are happy to get and we'll drag into their inbox because it's something they want. And so kind of like structurally, when substack is used correctly, we're actually one of the best, we're in the best position of all of the email people because we, people actually want these stupid emails. We're not, we're not powering the 5% off the gap that you didn't think you signed up for or whatever thing. It does mean that we have to be absolutely ruthless

about protecting the service from people that try to send, like, abuse it and, and use it for unwanted emails. There's a lot of like smart people at Substack that work extensively on that problem. And it's, you know, it's a key to the business for sure. Yeah. Okay. Well, Chris, I have to say, when we first met in that apartment, I didn't think we would be talking in this situation where I would be basing my career on your platform and you would be on your way to unicorn status. But here we are. It's been really a wild ride. It's been great to speak with you about not only the nuts and bolts of the technology and stuff like that, but really the impact that the platform is going to have on society and the fact that you're thinking about

this thoughtfully is pretty cool. So thank you. for joining and speaking with me for quite some time about all these different issues. And I'm sure everybody that's listened to this point has gotten a lot out of it. And I'm sure anyone who's dropped off about a half hour and also got a lot out of it. So I appreciate it, Chris. Thank you. Yeah. Well, thank you for having me. Thank you for being on Substack. Don't forget to turn on paid subscriptions. I won't forget. I haven't forgotten. It will just, it will take some time. All right. But I'll do it. I'll do it. You have my word. Okay, everybody. Well, thank you again for listening. Thanks Chris Best for being here, taking some time out of his very busy day and startup

life to chat with us here on the big technology podcast. Pleasure coming at you as always. Thank you, Nick Watney, our editor, our fearless editor who turns these things around extremely quickly. Red Circle for hosting and selling the ads, kind of maybe think of them as the substack of podcasts, but they like advertising. So maybe we get you guys in a cage match or something like that and figure it all out. And once again, thanks to you, the listener, couldn't do without you. Appreciate you being here with us again. And we'll see you next Wednesday on the Big Technology Podcast.