Chris Best

Chris Best is a technology entrepreneur and CEO of Substack. In 2017, he co-founded Substack, the publishing platform that helped popularize paid newsletters and direct-to-audience media businesses for writers, journalists, and creators. Previously, he worked as a vice president of engineering at Kickstarter and earlier co-founded the social messenger app Kik. Under his leadership, Substack has grown into a major player in independent media, attracting prominent authors, commentators, and podcasters seeking ownership of their audiences and subscription revenue. ------ Thank you to the sponsors that fuel our podcast and our team: AG1 https://DrinkAG1.com/tetra ------ Athletic Nicotine https://www. AthleticNicotine.com/tetra Use code 'TETRA' ------ LMNT Electrolytes https://DrinkLMNT.com/tetra Use code 'TETRA' ------ Lectio 365 https://Lectio365.com ------ Sign up to receive Tetragrammaton Transmissions https://www.tetragrammaton.com/join-newsletter

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:02Rick Rubin?

  Tetragrammaton.

• 0:23Speaker 01

  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, 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 gonna 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 broad strokes. Look, the internet came along, smashed a lot of the business models that used to sustain

• 1:08Speaker 01

  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 a way that was satisfactory to me. Yeah. And I was just kind of whining, I was going off and saying, wah wah, 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, people, other, other people may have noticed that some of these trends are going

• 1:51Speaker 01

  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.

• 2:22Rick Rubin?

  And what was the core idea?

• 2:24Speaker 01

  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 people 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.

• 3:04Rick Rubin?

  And then from writing that, what was the moment of, okay, I'm going to build this as opposed to just a theoretical solution to a problem?

• 3:15Speaker 01

  Yeah, we were arguing about the thing. And I've always felt that if you, 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, I think. 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.

• 3:58Speaker 01

  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, 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

• 4:40Speaker 01

  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 it 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.

• 5:16Rick Rubin?

  Tell me a little more about the much larger thing, like in the fantasy version of it. Tell me the big version of the dream of what it could actually be.

• 5:27Speaker 01

  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, Peemish was a writer I'd been trying to write. It was this writer focused thing. I don't think the, the idea is actually not only for writers, but I felt that the people who had the, were the most interesting to read, had this kind of like outsider nerd thing. And if you could free them to

• 6:01Speaker 01

  pursue their obsession or pursue their vision to the utmost,

• 6:08Speaker 01

  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, one way to look at Substack early on was like, hey, come and type into this box.

• 6:32Speaker 01

  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.

• 6:46Rick Rubin?

  Yeah.

• 6:46Speaker 01

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

• 6:50Rick Rubin?

  Did you think of it as a countercultural thing or no?

• 6:55Speaker 01

  Yeah, I would say so.

• 6:59Speaker 01

  At least in the sense that really good new ideas are always countercultural or there was.

• 7:05Rick Rubin?

  It always starts as the counterculture.

• 7:07Speaker 01

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

• 7:19Rick Rubin?

  So the first step, seeing a paid email that made sense, seemed like this could be a good way to start.

• 7:28Speaker 01

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

• 7:45Rick Rubin?

  How did the name come?

• 7:47Speaker 01

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

• 7:50Rick Rubin?

  What was the other one?

• 7:51Speaker 01

  It was either going to be Substack or Monograph.

• 7:53Rick Rubin?

  Both respectable.

• 7:54Speaker 01

  Both respectable. And.

• 7:56Rick Rubin?

  How did you choose?

• 7:57Speaker 01

  Somebody bought the domain monograph.com while we were arguing about it. And I said, screw it, I'm fine Substack.

• 8:02Rick Rubin?

  Okay. Do you know what the first piece posted on Substack was?

• 8:08Speaker 01

  The very first piece that was physically posted was sort of a manifesto that we, 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 a original vision for the thing. And I felt that 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.

• 8:42Rick Rubin?

  And how did you get him to move to Substack?

• 8:44Speaker 01

  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.

• 8:57Rick Rubin?

  Yeah.

• 8:58Speaker 01

  And he was that guy. He'd been he'd 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, could we just make that happen for you? He's like, that sounds great.

• 9:20Rick Rubin?

  Is there any competition in this space or no?

• 9:24Speaker 01

  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 Bullidin 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.

• 10:10Speaker 01

  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.

• 10:32Rick Rubin?

  I hear creators complain that the monetization part of it is not great.

• 10:38Speaker 01

  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 it won't, the algorithm won't like it.

• 10:59Rick Rubin?

  I see.

• 11:00Speaker 01

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

• 11:05Rick Rubin?

  Tell me about the pluses and minuses of the algorithm.

• 11:08Speaker 01

  I think people probably underrate the pluses, because algorithms are just technology. They are a way to amplify the will of the maker of the thing.

• 11:23Speaker 01

  And having an algorithm allows for really superhuman matching of people to things that they want to find. And when it works well, it can create serendipity. I think it can help something find an audience that loves it in a way that would have been impossible if you were trying to rely on only manual curation or only commercial discovery or something else.

• 11:57Rick Rubin?

  Did you consider in the early days, any options besides email? And any payment models other than subscription?

• 12:07Speaker 01

  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 gonna 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

• 12:50Speaker 01

  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.

• 13:06Rick Rubin?

  Yeah.

• 13:07Speaker 01

  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, neither does, you know, even YouTube doesn't really.

• 13:23Rick Rubin?

  Their business model is different than that.

• 13:24Speaker 01

  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.

• 14:06Speaker 01

  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.

• 14:24Rick Rubin?

  I don't think most people open their email like, what's in here for me today? I think of email as more of something you are obligated to deal with.

• 14:36Speaker 01

  I think that actually helped at the time because it's, 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.

• 14:50Rick Rubin?

  How long was it the email-only service before there were any other features?

• 14:58Speaker 01

  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, but they would, once they subscribed, they would stick around and have the direct connection in 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, other pieces.

• 15:34Rick Rubin?

  What did you find as it relates to free versus paid, size of the audience, conversion rate and why?

• 15:44Speaker 01

  This maybe gets to the business model question. Because the thing that in our minds differentiate 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. The fact that the way you make money is this better way.

• 16:23Rick Rubin?

  The only way you make money is if the creator is successful.

• 16:26Speaker 01

  Yeah.

• 16:27Rick Rubin?

  There's no other way.

• 16:28Speaker 01

  Nine times more money than we do. That's, that's just how it works.

• 16:31Rick Rubin?

  Yeah.

• 16:31Speaker 01

  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.

• 17:05Rick Rubin?

  Yeah.

• 17:06Speaker 01

  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 it'd be much higher, but it was, maybe the common theme was it was often much

• 17:50Speaker 01

  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.

• 18:14Speaker 02

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• 20:28Rick Rubin?

  What would you say the state of journalism was when you were launching?

• 20:35Speaker 01

  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.

• 21:10Speaker 01

  And I felt like that was unsustainable. And you couldn't sort of sustain a healthy intellectual culture that way.

• 21:21Rick Rubin?

  Do you think it's changed in the years since Substack started?

• 21:26Speaker 01

  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

• 21:46Rick Rubin?

  Yeah.

• 21:46Speaker 01

  thrown out, pushed out, like fired, chased out by mobs of people who disagreed with some element of what they were saying.

• 21:55Rick Rubin?

  Corporate interests, whatever it was.

• 21:56Speaker 01

  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

• 22:14Rick Rubin?

  And probably the most interesting people to read, as he said.

• 22:16Speaker 01

  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. I would say, well, just fuel up your getaway car.

• 22:40Rick Rubin?

  Yeah.

• 22:41Speaker 01

  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'd get a call three days later. You'll never guess what happened. You know, I might actually.

• 22:57Rick Rubin?

  Do you know of any people who are mainstream journalists who also have a Substack?

• 23:04Speaker 01

  There's definitely people who maintain three 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, it makes you more fully yourself and that gets more interesting. You know, I think Matt Iglesias was one of the editorial co-founders of Vox Media.

• 23:49Speaker 01

  As a reader of his, when he came to Substack, it was like Thayedin after Wormtongue left. And the Lord of the Rings, like he de-aged 10 years and regained his vigor and kind of like became more fully himself.

• 24:00Rick Rubin?

  Tell me about Barry Weiss.

• 24:02Speaker 01

  Barry 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, 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 BarryWeiss.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.

• 24:43Speaker 01

  You know, who believe in institutions to the extent that the existing ones have failed, get hungry to create new ones of their own. And I love when Substack can serve those people. And I think Barry 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.

• 25:09Rick Rubin?

  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.

• 25:27Speaker 01

  Yeah, 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, the upstart, the rival elite, the people who are making the new thing, it, it kind of wins. And I'm sure that Barry 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, who drew the most scorn from the media, it wasn't like, at the time,

• 26:10Speaker 01

  it wasn't like the, you know, the complete ideological enemies. It was sort of the, 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, a really thick skin to criticize your own side and to raise problems with your own side. And, you know, like I think Matt Tybee 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, and I think it actually helps the side.

• 26:54Speaker 01

  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 was, it's been painful over the years when people freak out about these things, I think it's worthwhile.

• 27:18Rick Rubin?

  Would you have imagined someone would quit working at the New York Times to come write a Substack? Was that always in the projection?

• 27:26Speaker 01

  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, 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.

• 27:55Rick Rubin?

  Yeah.

• 27:56Speaker 01

  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.

• 28:05Rick Rubin?

  The threat of Substack.

• 28:06Speaker 01

  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 is powerful.

• 28:16Rick Rubin?

  That's great. Tell me some of the pivotal moments along the way where something happened and it really created change at Substack.

• 28:26Speaker 01

  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.

• 28:37Rick Rubin?

  Yes.

• 28:38Speaker 01

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

• 28:42Rick Rubin?

  Cool.

• 28:43Speaker 01

  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.

• 28:49Rick Rubin?

  How was that experience?

• 28:50Speaker 01

  It was wonderful.

• 28:51Rick Rubin?

  What happened when you got there?

• 28:53Speaker 01

  You walk into a room of a bunch of other people who are, 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.

• 29:15Rick Rubin?

  Great.

• 29:16Speaker 01

  I actually think all of that stuff, like the cultural and sociological changes that it does are the main, a big part of the benefit. It gives you an excuse to upend your life. Like I'd been living in, you know, Kitchener, Ontario, Canada, building that initial version and it sort of gave me enough of an excuse to say, okay, I'm going to go move to California for three months and really focus in on building this thing, which was really good.

• 29:43Rick Rubin?

  Did you feel a sense of competition with the other people there or more camaraderie?

• 29:47Speaker 01

  I would say way more camaraderie. I mean, there's a, 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're, 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 it, I think it gives you permission to be more ambitious.

• 30:13Rick Rubin?

  That's great. So coming out of the Y Combinator experience, what happened then? Was that what allowed you to build it in the first place or no?

• 30:21Speaker 01

  No, I'd say we, we, we were able to build it. It wasn't, you know, we like

• 30:26Rick Rubin?

  It was simple.

• 30:27Speaker 01

  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 Y C, I managed to lure our other co-founder, Giraj, to the company, uh, 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

• 31:12Speaker 01

  they were having a really good experience and 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, 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. He's like, well, you know, come for dinner with Mark, come hang out, like, let's, 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.

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• 33:35Rick Rubin?

  What are your media consumption habits?

• 33:38Speaker 01

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

• 33:42Rick Rubin?

  Yeah.

• 33:43Speaker 01

  Partly it's, you know, I can justify it to myself that it's like I'm working and I'm dog fooding and using the product, which is true. And also, I love it.

• 33:55Rick Rubin?

  If you like to read, it's sort of a dream job.

• 33:57Speaker 01

  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.

• 34:15Rick Rubin?

  Would you say Substack is the antidote to social media?

• 34:19Speaker 01

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

• 34:28Rick Rubin?

  When did the app with the scrolling feature begin?

• 34:34Speaker 01

  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 can 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, like 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

• 35:16Speaker 01

  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.

• 35:34Speaker 01

  If you, 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,

• 36:18Speaker 01

  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 Tote's launch. And so we've 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.

• 37:02Speaker 01

  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, 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.

• 37:39Rick Rubin?

  In some ways. In the version where it was the emails, it was this invisible service that connected the creator to the audience. But now Substack can be more like a community or a bazaar where you go and find the things that you're interested in. Again, it's like the promise of social media was, but seems to have turned into something else.

• 38:07Speaker 01

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

• 38:13Rick Rubin?

  Yeah.

• 38:14Speaker 01

  Rather than the other way around.

• 38:16Rick Rubin?

  Yeah. If it were me, I would probably change the naming so that the app and the scroll is not notes, but that's what Substack is.

• 38:25Speaker 01

  Yeah.

• 38:26Rick Rubin?

  And everything else just feeds Substack. And the business model is not based on that, but that's the bazaar where you can find what you're looking for.

• 38:37Speaker 01

  It does still drive and connect to the business model, though, because you asked about algorithms.

• 38:41Rick Rubin?

  Yeah.

• 38:41Speaker 01

  We got to the power of algorithms. The problem of algorithms is that it's 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 it as sensationalism, but it's sort of like it's acting against you. Right? It doesn't have your best interests at heart.

• 39:23Speaker 01

  It is optimizing you for some end that is not the end that you would pick.

• 39:29Rick Rubin?

  Yeah, it's the economy of clicks.

• 39:31Speaker 01

  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.

• 39:45Rick Rubin?

  Yes.

• 39:46Speaker 01

  To the point where you choose to pay for it and.

• 39:49Speaker 01

  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, it's not perfect. But we've given you that choice. We've put that choice in front of you in, 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.

• 40:21Rick Rubin?

  It also feels like Substack at least started about writers and writing. And Twitter was about text and Instagram was about images. So in some ways, the relationship between Twitter and Substack are closer than maybe any other social media, because it's about the word. And recently Twitter is prioritizing away from the word and more into videos and more into imagery and other things. More like Instagram or TikTok. So for Substack to be the home of the word

• 41:04Rick Rubin?

  seems like a very good thing and I'd be wary of owning that segment. That doesn't mean not doing anything else, but knowing that on Substack, the word is king.

• 41:17Speaker 01

  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,

• 41:58Speaker 01

  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 into the deep stuff. I actually think the same is true for video as well, but time will tell.

• 42:43Rick Rubin?

  What are your thoughts on free speech? And what is the current policy at Substack towards free speech?

• 42:51Speaker 01

  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 this, 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.

• 43:35Speaker 01

  But beyond that, we try to be very, very liberal.

• 43:40Rick Rubin?

  Would you say if it's legal, it could be on Substack?

• 43:43Speaker 01

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

• 43:50Rick Rubin?

  Let's talk about some of the controversies that have centered around Substack over the years. What was the first pushback you felt?

• 43:59Speaker 01

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

• 44:29Rick Rubin?

  Yeah.

• 44:30Speaker 01

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

• 45:10Rick Rubin?

  Substack doesn't have any editorial position. Is that correct?

• 45:14Speaker 01

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

• 45:57Rick Rubin?

  But you're not condoning anything on Substack, is that correct? Just to be clear.

• 46:02Speaker 01

  No, no, just to be clear, it would be, it would be impossible to condone everything on Substack. There's such a wide variety of things of all stripes and types, and I wouldn't want to run a platform that I condone everything on. I don't, I don't think that I am qualified for that job. I don't think I'm qualified to be the arbiter of what's true or what's good. And that I, the people who are, who ask tech platforms like ours to do that sometimes are perhaps well intentioned, but are mistaken in their belief that that's a good thing.

• 46:33Rick Rubin?

  I'm not sure that anyone would have the ability to properly police things in a fair way. I don't know that it's possible. And I imagine for every piece on Substack that argues one position, you'll find another writer who might have the opposite position. There's no party line on Substack at all.

• 46:57Speaker 01

  No, and that's, that, that sense of independence is part of the appeal, I think. And it, and it's something that the political winds have shifted since those early days. A lot of people who were critical of us for, you know, platforming people have faced censorship pressures themselves and are now have come, sort of come to understand the, the value of a liberal commitment to freedom of the press. I also think there are, I want to sort of give the critics their due here, or give the opposing side its due. There's a way you can go about this where if you just said, look, any kind of check on expression is presumptively wrong. And so the only way to actually have freedom of expression is for anybody

• 47:41Speaker 01

  to be able to say anything they want in any venue at any time. And you kind of like throw the thing fully open. I actually think that can be a trap as well. You can create kind of like a thunderdome like thing where it's the equivalent of like you being in your living room, people feeling free to come in and shout at you all the time. And you're just like, hey, this doesn't work either. And I think some platforms can kind of like let that dynamic fly too far. So the point of Substack is not that there's no rules. The point of Substack is that there's not one set of rules. It's not Chris coming in and saying, here's what everyone's allowed to say. It's like your Substack is your house. And you get to set the rules and you can have them be quite strict. You could say, we're not allowed to call names here, or only Christian things, or only anti-Christian things.

• 48:26Speaker 01

  And that's good, right?

• 48:27Rick Rubin?

  Of course.

• 48:27Speaker 01

  Because I think the thing that we need to show is that you can have freedom and civilization at the same time. It's not the case that the only alternatives are, you know, some centralized power that tells you what it's okay to think and say, or complete anarchy where everybody just shouts at each other. You can, with some structure and with some giving people the right tools and the right power themselves, you can have something that actually works and is beautiful and that people are free.

• 48:56Rick Rubin?

  I remember one in particular, there was a smear campaign early on. Maybe it was in the Atlantic. Does that sound familiar?

• 49:06Speaker 01

  That one was kind of like right wing content. It was like, hey, there's offensive stuff from the, from the far right. And it's true, there is some far right stuff and there's far left stuff and there's, you know, offensive, offensive things of all, of all stripes. Well, here's another, like, here's another, because there's, there's been a series of controversies of like, why is thing X allowed on Substack? One of them was kind of like, what's going on with trans issues? One of them was this kind of, you know, why are you allowing right wing people? But the other one I'm now remembering was, was sort of COVID skepticism. Right, there was people who were running the gamut from, you know, are these vaccines good to like, where did this virus come from to are the measures we're taking against it the right ones?

• 49:51Speaker 01

  And there was really, really strong pushback and a strong sort of cultural and sometimes legal thing that was like, you know, you can't let people say this stuff. You can't let people question these things. And we took a position that like, you gotta let people question this stuff. And I think some of that stuff, you know, in my judgment is crankery, right? Like, I think a lot of the anti-vax stuff is not right and probably does harm and is is that bad? And some of it turned out to be right, probably like some of the, you know, people who are questioning some of the measures. I think you can, I don't, I don't know if we've resolved the question of where COVID came from, but I think it's at least an open question that's legitimate

• 50:35Speaker 01

  and to debate and shouldn't be, you know, shut down with accusations of racism or whatever. And that was, yeah, that was another kind of a moment for me that exposed why this stuff actually matters. You have to let people ask questions. You have to let people challenge the received wisdom, even if they're wrong, even if they're, if they seem crazy. I just think that's like a crucial part of a free society. And, you know, Substack has been that we've drawn a lot of criticism for that. Here's another piece of this is like, I think there's like a, there's a place where I saw a lot of companies go off the rails, I think, especially in sort of like 2020 around that era was like, the way these things would, would work was there'd be like this,

• 51:21Speaker 01

  you know, you get like a social media mob that would show up. Any surface on the internet that you would open would just have all of these people shrieking at you and telling you that you're the worst person and threatening you and all of this stuff. And I think part of what social media does is create a false illusion of consensus. It would feel like everyone was mad at you, or everyone hated you, or everyone thought you were, what you're doing was crazy, when really it would be like, there's like a couple hundred people that are really ginned up about this. And I think it's very tempting, if that happens to you, to give in and to say, okay, okay, okay. I, I hear you. I'm listening and learning. I'm gonna do this first step to start making this better.

• 52:05Speaker 01

  And I think as soon as you do that, you are lost. Either you're in control, or the mob is in control. And as soon as you like, let the mob start to be a little bit in control, it's like, it devolves and devolves and nothing satisfies it. And so we, one of the things that we did, you know, and this, it feels this way in the press, and it feels this way when you get these social media things is, as painful as it was, we did just sort of hold firm. We wrote a few essays in advance outlining our philosophy about, you know, free speech and freedom of the press, and why we were doing what we're doing, and why things were the way they were. And we can sort of consult back to, you know, what we had written with cooler heads.

• 52:48Speaker 01

  And then a lot of what I think of as our success was just not giving in, like not getting tilted, just being like, yep, everyone's mad. The people who are our customers, who are concerned, we'll talk to and we'll empathize with them and tell them what we're doing. But we're not gonna abdicate our responsibility or our judgment to the critics in the press, or to the, the critics on social media. I think that saved the company, basically. I think being willing to stand up in those moments feels hard. But maybe this is, if, the advice I would give to somebody going through that is like, stick by your principles. If you're gonna get smashed, get smashed for doing something you believe in, because that's worth it.

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• 55:08Rick Rubin?

  So tell me all of the features available on Substack now.

• 55:11Speaker 01

  First of all, you can use Substack just like a normal podcast host. So you can create a Substack, you can publish, you know, upload an audio file. It can distribute that to Apple Podcasts and to Spotify. We can also auto-publish to YouTube now. And so if you're, if you're just trying to have like a, a good podcast host for free, Substack works for that. And you still get the subscription feature so people can still come and give you their email and subscribe. We also have the ability to, to pay well. So you can do a paid subscription and then people can, if they're using their podcast app, they can add their private podcast feed and get the, the paid version.

• 55:54Speaker 01

  Now that the app exists, though, that those things work even better because you can, anybody who has the Substack app can go to the like, listen tab and find the things that they're subscribed to that they want to read.

• 56:05Rick Rubin?

  Are more people moving over from reading on the email to reading on the app?

• 56:12Speaker 01

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

• 56:21Rick Rubin?

  On each email, is there a read it in the app tab?

• 56:24Speaker 01

  Yeah, you can also, I mean, we have a read aloud thing. So as the author, you can read aloud, you can, you can create your own audio version of the post, which I actually love when people do that. Or we have a really good AI one. If you don't do that, or if you just want, if you're in the car, but you want to hear this post, you can do that. The other thing I'm really excited about is, you know, we talked about for writers, the fact that you could come and type into this box. And if the thing you type was great, everything else is taken care of. We're working on a set of features that I think we'll be able to do that for video and audio conversations. The current incarnation of this is Substack Live, where you can go live from the app.

• 57:08Speaker 01

  And the thesis behind this is we're at the point with some of these new AI tools that if you can have a really interesting, you can have something that feels like a, like a FaceTime conversation or a video call. And if you can have the most interesting conversation in the world, we can make all of the other pieces sort of work automatically in a way that's sort of newly good. And I think something maybe possible in that realm, like it was for writers, where it's like, there are a lot of people who could have a really interesting conversation.

• 57:49Speaker 01

  But I guess I don't have to tell you that the, the mechanics of making a really good recording and editing it and having all of those pieces come together. Like, I think the status quo, even today in the world is you either have to sort of be an audio nerd yourself, or have a, hire a team of audio nerds, even to make, you know, forget about a, a amazing album, but even to make like an acceptable podcast is pretty difficult. There's still a pretty high barrier there. And I think we're Going to be able to dramatically reduce the barrier to the point where anybody who wants to have a conversation and publish a great artifact of it will be able to just do that.

• 58:31Rick Rubin?

  And when you say conversation, that means between two people?

• 58:34Speaker 01

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

• 58:47Rick Rubin?

  What are future features you imagine coming to Substack?

• 58:51Speaker 01

  I mean, we're gonna, we're gonna ship some iterations of this video recording live stuff that just make it much more powerful. Especially the, the editing, the ability to, you know, make cogent clips or, you know, the, the bar for how well a human can do it. That's really good is like very, very high.

• 59:11Rick Rubin?

  Yes.

• 59:12Speaker 01

  But the bar for how good it has to be before it's like serviceable for a conversation is actually still fairly high, but is much lower than that. And I think we're going to get to a world within the next month or two where anybody who wants to make something that's a podcast or a conversation is going to be able to do that and have it be sort of automatically pretty good.

• 59:35Rick Rubin?

  It also seems if AI can beat grand master chess players and Go players, AI could probably eventually do some of that technical work.

• 59:45Speaker 01

  Yeah, I think in the limit, it should be able to be really good. There's a more interesting question, which is, do you need the humans at all? Like, why not just listen to the best AI conversation? Like, instead of just the interview, like, why not the interviewer and the interviewee? Which I think is a very deep question.

• 1:00:03Rick Rubin?

  Again, if the content is good, does that matter? I don't know.

• 1:00:07Speaker 01

  Does that matter? What does, what does good mean?

• 1:00:09Rick Rubin?

  Any other uses of AI that you're considering or playing with?

• 1:00:13Speaker 01

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

• 1:00:34Rick Rubin?

  Are there features that you imagine that would be great, but you have no idea how to do them yet?

• 1:00:41Speaker 01

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

• 1:01:24Speaker 01

  And have that turn into world-class media? That I think is much harder, but I'm very excited about. Basically, I think that would be, that would be truly magical.

• 1:01:35Rick Rubin?

  Are there possibilities for collaborations with other online businesses like Shopify?

• 1:01:44Speaker 01

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

• 1:02:27Speaker 01

  He had like a bunch of sort of like, you know, high-value software products that he put into the subscription. And it was like extremely successful.

• 1:02:35Rick Rubin?

  Any moments along the way in the Substack story that caused a big bump in use? Or caused a lot of conversation around Substack?

• 1:02:45Speaker 01

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

• 1:02:55Rick Rubin?

  Who were some of the people who came over at that time?

• 1:02:57Speaker 01

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

• 1:03:03Rick Rubin?

  Since then, have there been big bumps in the action?

• 1:03:06Speaker 01

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

• 1:03:12Rick Rubin?

  I don't know about that.

• 1:03:13Speaker 01

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

• 1:03:23Rick Rubin?

  Oh, yeah.

• 1:03:23Speaker 01

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

• 1:03:27Rick Rubin?

  TikTok creators would move over to Substack.

• 1:03:30Speaker 01

  TikTok creators who would, who maybe didn't even move or just like, I don't know what's happening with this app.

• 1:03:34Rick Rubin?

  Yes.

• 1:03:34Speaker 01

  I nearly realized how important it is for me to have some way to contact my audience. And what didn't work, I don't think for almost anybody, was I'm going to start doing on Substack what I did on TikTok. But many people who brought their audience then realized, oh, there's more I can do here. Like, oh, you mean I can write something and people could read it? Or I, you know, I could make a longer thing and people might check it out? That was sort of like a big moment. We've had a lot of interesting controversies. We've had various times where people have been angry that we, you know, take a strong stance in favor of freedom of the press and allow various points of view or various things that people disagree with.

• 1:04:15Speaker 01

  I expect we'll get like one of those every year or two for the rest of my life if we succeed.

• 1:04:21Rick Rubin?

  Tell me the history with Twitter.

• 1:04:24Speaker 01

  So I guess maybe early on in subject history, we were very symbiotic with Twitter. In the sense that this was a platform for long form writing, you know, OG Twitter was very, as you say, it was sort of like the short form social network of the literate, of people who wanted to read. And old Twitter, in my mind, a lot of what people were talking about would be links to long form things. And links performed very well. And, you know, a big part of why Twitter became what it became was it was sort of like the place you would go for the headlines. And so in the early days, a lot of those moments where people would come and bring their audience, it would be somebody who had a following on Twitter, who would say, hey,

• 1:05:07Speaker 01

  I'm starting a Substack, maybe I just got fired, or maybe I'm just striking out on my own, you know, come check it out. You could just post a link and it would, all your people would see it. And if they were compelled by it, they would come.

• 1:05:18Rick Rubin?

  And it was a different kind of content. It was, I'm gonna write a long thing about this, this is where it's gonna be, you can find it here.

• 1:05:24Speaker 01

  Yeah. And then, you know, the conversation would live on Twitter, but there, you could still, you know, you could still have a long form piece of writing.

• 1:05:32Rick Rubin?

  Yes.

• 1:05:33Speaker 01

  That would do the rounds. It would be like, oh yeah, everybody's reading this thing. There'd be a conversation about it. And yeah, that was like a major driver in the early days. Over time, and actually even before Elon bought Twitter, that became less and less true. I think as they optimized the algorithm, it ended up penalizing any kind of links out. At least at the start, not out of any malice, I don't think, but more just, it makes sense given what you're optimizing for. But if you're optimizing for time spent scrolling such that you might see an ad, if somebody clicks out to read

• 1:06:14Speaker 01

  a thoughtful long form thing, you're losing money. Given the objective function that you might naturally create for that algorithm, those things will penalize. So it became a smaller and smaller share of like the top of funnel traffic that was helping people on Substack grow. And then Elon bought Twitter. I had talked to him at some point, we were sort of comparing notes and.

• 1:06:38Rick Rubin?

  Was he a Substack fan, do you know?

• 1:06:40Speaker 01

  I think he was, he was at least a fan of, we at that point had, I think, been the platform that had taken a pretty strong stance in favor of freedom of the press. A lot of the things that he at least said he espoused.

• 1:06:57Rick Rubin?

  Yes.

• 1:06:57Speaker 01

  Were things that we had been doing. And so I think he was sort of a, at least theoretically, a fan from, from that perspective.

• 1:07:04Rick Rubin?

  Yeah. Ideologically aligned.

• 1:07:07Speaker 01

  Yes.

• 1:07:09Speaker 01

  Although I would say, given what's happened since, maybe questionably so.

• 1:07:14Speaker 01

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

• 1:07:58Speaker 01

  Cause he saw it as a Twitter competitor. And I think there was, there was a moment there where there was sort of this meme of like, is Twitter actually going to fail? Is this going to like tip over? People are going to switch over to Blue Sky, switch over to Threads, or switch over to somewhere else? And so he saw us launching this feed as kind of, I think, a declaration of war. And he banned all mention of Substack on Twitter. There was a week where not only could you not share a Substack link, if you just said the word Substack, nobody would see your thing. And if you searched for, literally you'd search for Substack on Twitter, it would say, no results. Like, doesn't exist. We were like Voldemort. You can't say the name. And that, I think, after some backlash, they canceled that policy pretty quickly,

• 1:08:43Speaker 01

  but left in place a bunch of kind of like underhanded things that would hurt traffic. I think Substack and The New York Times were the two sites for a while that got the treatment where you would click on a link and it would go there, but it would delay for five seconds. Like you just click and it would just be like, spin. And five seconds sounds like a short amount of time, but in, you know, software, it's an eternity.

• 1:09:06Rick Rubin?

  And that wasn't a glitch. That was an intentional.

• 1:09:09Speaker 01

  It was, I'm,

• 1:09:11Speaker 01

  it was intentional. And there was like various de-boosting and all these things. And I haven't talked to him since.

• 1:09:17Rick Rubin?

  Did anything cause them to get fixed or just got fixed?

• 1:09:20Speaker 01

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

• 1:10:07Speaker 05

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• 1:12:22Rick Rubin?

  What's different about Substack from Medium or Patreon?

• 1:12:28Speaker 01

  So the biggest difference from Medium is the business model. My view of Medium is they took sort of the underpants gnome theory of building one of these things, just like step one, get a bunch of attention, question mark, question mark, question mark, step three, profit. And so they sort of had this period of trying out a bunch of different business models, one of which was very similar to the Substack business model. But through most of Medium's history, there hasn't been any idea of like direct connection or ownership as a creator, as a writer. And so like on Medium, you'd pay five bucks a month for all of Medium and it would be sort of Netflix style. It would like give you some slice of the thing if you clicked on a thing.

• 1:13:08Speaker 01

  And what that means is if you're making stuff on Medium, you're kind of like playing to the algorithm all the time to like get anywhere. And very early in, you know, when we were still in YC, actually, Medium used to publish, here's what the top earning writer on Medium made last month. And we would look at it and be like, there's people on Substack that are making more than that. And they're not making more than that because they had the one hit that they could never replicate, that like happened to get a gajillion clicks and then the algorithm doled out a big paycheck. They've got that because they've got a loyal audience of people who value what they do. It's just such a better deal creatively and financially to have some connection with

• 1:13:53Speaker 01

  your audience and to have people who are showing up and paying for you. And so I think it was able to attract a much better caliber of writer over time. And then Patreon is very interesting because Patreon is similar in some ways. I've talked to Jack a few times and I think maybe early on I would have said Patreon was doing the thing where they were trying to be very pure. And they're like, we're really just going to be about the payment relationship. Jack's a musician. He's like, I want to be so creator, you know, focused and friendly that I'm never going to like try to impute on the relationship at all. So we're just going to handle the payment for you and we're kind of not going to do the rest.

• 1:14:37Speaker 01

  And you're not really consuming the content on Patreon. The prototype thing is you're a musician or you're a YouTuber or you're somebody. And they didn't want to do discovery. They didn't want to help you grow because they felt like it would be sort of tarnishing the pureness of the thing. And I've argued with Jack about that over the years. My view is he's come around to my way of thinking and they're looking at Substack saying, oh, one of the most important things you can do for creators is help them grow and find an audience, especially new creators, especially the next generation of people who are trying to come up. And now, again, I'm biased, but my view is they're just copying a lot of the things that Substack is doing, which I think are good ideas.

• 1:15:19Speaker 01

  But in terms of like having a network that's a place on the internet that you go, I don't think Patreon has achieved that yet.

• 1:15:26Rick Rubin?

  Tell me about comments on Substack.

• 1:15:28Speaker 01

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

• 1:15:35Rick Rubin?

  What's the difference between commenting and replying?

• 1:15:38Speaker 01

  If you reply, it only goes to the author.

• 1:15:41Rick Rubin?

  I see.

• 1:15:41Speaker 01

  And if you comment, other people can see it, including the author.

• 1:15:44Rick Rubin?

  Is that understood? Everyone knows that?

• 1:15:47Speaker 01

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

• 1:16:03Rick Rubin?

  Good.

• 1:16:05Speaker 01

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

• 1:16:17Rick Rubin?

  Yeah.

• 1:16:17Speaker 01

  And be, honestly, if they do hate, if it's like, I cared and I hated enough to come and give you my $10 to leave this angry message. Well, maybe that's worth it, or maybe that's, that's interesting anyway. But a lot of people on Substack, the value they get from earnest commenters and earnest replies, the feeling of people engaging with the ideas and caring and talking about it is a big piece of what makes the thing kind of special. And now that the people are in the app, it's much easier to comment. It's much faster. So you're getting a lot more of that. And one thing that I've followed from like here, the early internet blogosphere is a lot of the most interesting bloggers kind of like came out of comment sections.

• 1:17:00Speaker 01

  Like a comment section can be like of, of a popular blog or a popular Substack can be like its own scene, where its own little universe of people that get to know each other and bounce ideas off each other and become known. And then you can sort of get people that kind of grow up in the comment section of one thing and then go out and start their own.

• 1:17:17Rick Rubin?

  Walk me through best practices for Substack users.

• 1:17:21Speaker 01

  My number one piece of advice I always give people is just start. I think the most common failure mode for somebody who aspires to do a Substack is to think really hard about it. Do a lot of planning and a lot of strategizing. And by far, the best thing you can do is just, it's easy to start. It's free. Set it up. Put something out there. Don't worry about it being the perfect thing. I also think, you know, different people take a different path with this, but I think a good default is default to creating more, more frequently. I think the internet in general, and definitely Substack,

• 1:18:00Speaker 01

  there's sort of a natural benefit to having sort of less filter and being able to like publish frequently, putting lots of things out there. You know, if you put 10 things out there and eight of them are kind of so-so and one of them is really great. That works.

• 1:18:19Rick Rubin?

  That's true, even if it's an email?

• 1:18:21Speaker 01

  Like, if you're gonna publish more than one thing a day.

• 1:18:23Rick Rubin?

  Yeah.

• 1:18:23Speaker 01

  I might say, you know, pick and choose.

• 1:18:25Rick Rubin?

  Even up to one a day would be not too much.

• 1:18:28Speaker 01

  A lot of the most successful substackers do five a week or more.

• 1:18:32Rick Rubin?

  Yeah, that's interesting. I wouldn't have guessed that.

• 1:18:34Speaker 01

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

• 1:19:07Rick Rubin?

  Yeah.

• 1:19:07Speaker 01

  And that became the most popular thing I ever did, or that became the thing that got everybody into my work, that got them to read the other stuff in the first place. Have you ever heard the story of like the two sculptors?

• 1:19:18Rick Rubin?

  I don't think so.

• 1:19:19Speaker 01

  There's two sculpting classes, and the teacher for the first class says, okay, at the end of the semester, I'm gonna just take your very best piece. A hundred percent of your grade is gonna be based on the quality of only the best thing you made. And the other teacher goes to the class and says, I'm going to give you a grade by the pound. The more pounds of sculptures that you make, regardless of quality, that's gonna be the grade you get. And in this made up story, what happens is, the people in the second class, if you, when you go back and look at the best thing they made, it's much better.

• 1:19:56Rick Rubin?

  Because of the practice?

• 1:19:57Speaker 01

  Because of the practice, because of the benefit of momentum and getting going. Because when you set out to only make the one best thing, it can be so paralyzing. And you can spend all of your time, you know, polishing this one thing and refining. And in many cases, you would have been better served by getting more out and giving yourself the space to like iterate and to try more things. And sometimes, many times in creative pursuits, I think sometimes those accidents are like the, where the magic happens.

• 1:20:29Rick Rubin?

  Any other tips for creators?

• 1:20:32Speaker 01

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

• 1:21:08Rick Rubin?

  I've heard businesspeople say that Substack could never be a serious media company based on its financial model of only taking 10%. Are you committed to that model being the model going forward as long as you can?

• 1:21:22Speaker 01

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

• 1:22:07Speaker 01

  of, of the value. Those are kind of core things for us.

• 1:22:11Rick Rubin?

  Is Substack about journalism or is it about something else?

• 1:22:15Speaker 01

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

• 1:22:30Rick Rubin?

  Do you think Substack's changed journalism?

• 1:22:34Speaker 01

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

• 1:22:58Rick Rubin?

  Have you seen anything go from Substack and bleed into mainstream news? Like something that wouldn't have been in the news had it not been for the Substack first?

• 1:23:13Speaker 01

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

• 1:23:15Rick Rubin?

  Yeah, I love Jonathan Haidt.

• 1:23:16Speaker 01

  So he started a book on Substack. He started serializing it.

• 1:23:22Speaker 01

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

• 1:23:49Rick Rubin?

  The idea of either serializing a book or developing a book on Substack, and then eventually someday you get the book. That's a really beautiful idea. I could see how some people would think they undermine each other.

• 1:24:07Speaker 01

  Yeah.

• 1:24:08Rick Rubin?

  But it does just the opposite. They amplify each other. It's a fascinating aspect of the internet age. When you give something away for free on the internet, it doesn't make it now worthless, but it makes it more valuable.

• 1:24:23Speaker 01

  Yeah, the same people who read it will buy it again.

• 1:24:25Rick Rubin?

  Yeah.

• 1:24:26Speaker 01

  And in fact, having a, having an email list of people that love to read you is one of the best places to sell a book.

• 1:24:30Rick Rubin?

  That seems like a very clear path to expanding Substack's writer base. Just really making that pitch.

• 1:24:39Speaker 01

  Yeah.

• 1:24:40Rick Rubin?

  To as many writers as you possibly can in any way that you can, because it's a no lose proposition.

• 1:24:46Speaker 01

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

• 1:25:02Rick Rubin?

  Is there an opportunity to do writer bundles where instead of just subscribing individually to each writer, either you subscribe to five and there's some benefit to doing that? Or maybe there are a group of writers who decide to bundle their things together at some advantage to the reader? Is that possible?

• 1:25:20Speaker 01

  Yeah, we're running some experiments along these lines now. I find it very interesting. One of the things that fascinates me is like, you know, we talked about the media company of the future. Like, what is the media company of the future? What are, you know, if you're an ambitious media founder right now, what should you be making? There's one idea that's like, I'm going to make something that's like a newspaper. But there's another case, I think, that says, maybe I'll make something that's like a record label. Where I'm not trying to create one unified editorial product necessarily, but I'm trying to kind of like spin up and help mentor or make or produce or, you know, have this kind of like loosely affiliated

• 1:26:02Speaker 01

  set of voices that maybe you can get them individually or maybe you can get a bundle. But the enterprise that I'm making, the company that I'm making is less a singular editorial viewpoint and more kind of like a scene or a collection of people. We're very interested in that right now. And we're testing out some bundle models that are like this, where people could either start a company and make a bundle or kind of group together into a bundle and see if that helps. I've thought about this a fair amount.

• 1:26:31Rick Rubin?

  Yeah.

• 1:26:32Speaker 01

  I think there is a way to do it that would be bad. Like, I think if we just, if we literally just did the medium thing where it says, look, just pay one price.

• 1:26:39Rick Rubin?

  Yeah.

• 1:26:39Speaker 01

  And you'll just get everything. I think that does undercut the relationship. But I think there are other ways you can go about doing some bundling stuff that doesn't undercut it. And we're playing with those.

• 1:26:53Rick Rubin?

  Has it becomes more and more of a? Hub of Substack being meaningful as a discovery engine.

• 1:27:01Speaker 01

  Yeah.

• 1:27:02Rick Rubin?

  Feels like it plays into that side of it.

• 1:27:04Speaker 01

  We're starting to see that matter for writers and creators too. People are coming to Substack. It used to be like, you know, no one's ever heard of this, but I like, I hear people are making money. And now there's people that come that are like, all of the interesting things I read are here.

• 1:27:18Rick Rubin?

  Yeah.

• 1:27:18Speaker 01

  And I feel like if I'm not here, I'm sort of, I'm not even in the conversations that I find most interesting.

• 1:27:24Rick Rubin?

  What are the most popular genres on Substack?

• 1:27:27Speaker 01

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

• 1:28:10Speaker 01

  But the reality is that it's this, it's this index fund of culture. It's got all these different things and it changes all the time, which makes it fun.

• 1:28:17Rick Rubin?

  What accounts do you read or what are your favorite accounts?

• 1:28:21Speaker 01

  There's a lot that are very good. I mean, one that is kind of special to me is Astral Codex 10, Scott Alexander. He's sort of a rationalist essayist and thinker in the weird Berkeley rationalist scene. But he's somebody that I've been reading for a long time that I really like.

• 1:28:42Rick Rubin?

  What is Substack Defender?

• 1:28:44Speaker 01

  Substack Defender? Oh, man. So we had. A thing that kept happening, because you'd have these, especially like local journalism, this happened a lot, where somebody would be covering a local business or politician negatively. And they'd be some independent person that's just trying to, you know, maybe there's no local newspaper anymore, but they're taking up the thing. And they'd write some negative story and they would get a really scary letter on legal letterhead that basically says, "We're going to ruin your life unless you shut up." I mean, there's, there's very strong legal protections for journalism and speech and criticism in this country.

• 1:29:27Speaker 01

  And so very often, these were just bogus claims, or claims that did not have a very strong chance of actually winning in court. But the ability to like make the threat, if you're an independent person, can be kind of debilitating. Because even if you defend, even just the cost of defending yourself can be very high and like, you don't really know, like, are they going to be able to find something? Or what is this thing? And so we created this program called Substack Defender. It was basically like, we're going to have a fund for picking up defenses of these things that anybody can apply to. We'll, we'll pick which ones we take. And we're going to pick a few things like this, where somebody is kind of trying to

• 1:30:08Speaker 01

  do censorship by lawfare, I think of it, just like really vigorously defend it and put a bunch of weight behind it, put a bunch of money behind it.

• 1:30:15Rick Rubin?

  Yeah.

• 1:30:16Speaker 01

  Try to like, you know, publicize it if necessary.

• 1:30:18Rick Rubin?

  Yes.

• 1:30:19Speaker 01

  Because the, the imbalance was, if you're some business person or government person, it's basically free for you to like send a scary, scary gram.

• 1:30:28Rick Rubin?

  Yeah.

• 1:30:28Speaker 01

  There's no real cost to you. It's cheap to get a lawyer. You pay a lawyer, they write up a meanly worded thing, you send it to somebody, it makes them afraid to do the work. But when you do that, there's a chance that there's like a very well-funded legal and PR defense that swings to their aid. Suddenly that can like tip the balance of power back in favor. And by doing even a relatively small number of those, you can help create a climate where it's not costless to harass journalists.

• 1:30:58Rick Rubin?

  That's great.

• 1:30:59Speaker 01

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

• 1:31:27Speaker 06

  Tetragrammatin is a podcast. Tetragrammatin is a website. Tetragrammatin is a whole world of knowledge.

• 1:31:42Speaker 05

  What may fall within the sphere of Tetragrammatin?

• 1:31:46Speaker 05

  Counter-culture? Tetragrammatin. Sacred geometry? Tetragrammatin. The avant-garde? Tetragrammatin. Generative art? Tetragrammatin. The tarot? Tetragrammatin. Out-of-print music? Tetragrammatin. Biodynamics? Tetragrammatin. Graphic design? Tetragrammatin. Mythology and magic? Tetragrammatin. Obscure film? Tetragrammatin. Beach culture? Tetragrammatin. Esoteric lectures? Tetragrammatin. Off-the-grid living? Tetragrammatin. Alt spirituality? Tetragrammatin. The canon of fine objects? Tetragrammatin. Muscle cars? Tetragrammatin. Ancient wisdom for a new age.

• 1:32:29Speaker 05

  Upon entering, experience the artwork of the day.

• 1:32:34Speaker 05

  Take a breath, and see where you are drawn.