Inside Substack’s $650M Playbook for the Future of Media (Chris Best & Hamish McKenzie, Co-Founders)

If you allow technology to be applied, it makes things better and cheaper. As everybody gets richer, as more things happen, the things that are not touched by technology just get more expensive and take up a bigger and bigger share of the economy. Then you can ask, okay, so what is AI technology going to do to media? It's as AI slop and AI entertainment takes over the entertainment piece of media. The part that gets more valuable is learning what to want, learning who you want to be and curating your information sources. And in that... Humans play an outsized role. If we could go with the 10 to 20 year time frame, I would say this is going to be looked at as the chaos era. This is a moment of transition between major periods in technology, in culture, in the media, creating a ton of volatility, a ton of power redistribution and chaos that is ultimately going to lead to a new kind of order and something better, but in the moment feels messy as hell. Hey, I'm Mario, and this is The Generalist Podcast. You might have heard the saying, the future is already here, it's just not evenly distributed yet. The mission of this podcast is to host deep conversations with the founders, investors, and thinkers who are living in that future to help you see it earlier, understand it better, and capitalize on it. Today, I'm speaking with Chris Best and Hamish McKenzie, Substack's CEO and Chief Writing Officer. Substack is arguably the most interesting media company in the world right now. It's become a transformative force in the landscape, creating a new economic engine for culture. With over 5 million paid subscriptions and tens of millions of active readers, Substack is building something that I consider truly revolutionary, a platform where creators own their work and make money directly from their audience through paid subscriptions. In our conversation, we talk about... Chris's grand unified theory for how AI will influence content creation, the inside story of subsex clash with Elon Musk, and why the ceiling for great writing and culture might be much higher than we're currently imagining. Given my work at The Generalist and love for writing, these are all topics that I was extremely excited to talk about with Chris and Hamish and loved hearing their perspectives.

you'll walk away with practical insights about the new media landscape, creator economics, AI, and what great information and writing looks like in the 21st century. This is a new podcast, so if you like it, I hope you'll consider subscribing and joining us for some of the incredible episodes we have coming up. Now, here's my conversation with Chris Best and Hamish McKenzie. This episode is brought to you by Vanta. Warren Buffett once said, it takes 20 years to build a reputation and five minutes to ruin it. For today's digital companies, those five minutes have shrunk to milliseconds. This asymmetry is why trust isn't just earned, it's demanded. If you're building a business, you likely know that proving compliance is needed to win bigger deals, enter new markets, and deepen trust with customers, but that it can cost you real time and money. By automating up to 90% of the work needed for SOC 2, ISO 27001, HIPAA, and more, Vanta gets you compliant fast, opening doors to next-level growth opportunities. Not only does Vanta save you time, it also saves you money. A new IDC white paper found that Vanta customers achieve $535,000 per year in benefits, and that the platform pays for itself in just three months. Over 10,000 companies like Atlassian, Factory, and Chili Piper use Vanta to manage risk and prove security in real time. My listeners can get $1,000 off Vanta at vanta.com slash mario. That's vanta.com slash mario for $1,000 off. This episode is brought to you by Brex. Fred Adler, the influential venture capitalist of the 1970s, was known for displaying decorative pillows in his office that featured a signature business philosophy. Corporate happiness is positive cash flow. In today's post-SERP environment, Adler's wisdom feels particularly relevant as founders need to make every dollar work harder. That's exactly what Brex delivers. Their modern finance platform was built specifically for startups like yours and designed to help extend your runway when capital efficiency matters most.

With Brex, you get global corporate cards with up to 20x higher credit limits and no personal guarantee required. Their banking solution has no minimums and no transaction fees, while letting you earn high yield from day one with same-day liquidity. Best of all, Brex knows you were born to build, not juggle spreadsheets and finance tools. Their AI-powered platform brings cards, banking, expense management, and travel all in one place. It's simple. scalable, and designed to get you back to what you do best, building. More than 30,000 companies, including one in three U.S. venture-backed startups, trust Brex to help make every dollar count toward their mission. Join them at brex.com slash Mario. Chris Hamish, it is fantastic to have you on here today. Thank you so much for being here. I am so excited to talk about Substack and the future of media, things that... all three of us love to chat about. And maybe to begin, I'd love to just start with a little introduction about Substack, the vision behind it, the mission that you're building, the scale it's at today. Because I think that, you know, I would imagine almost everyone who's listening has interacted with Substack in some way, but they may not know it. So Chris, maybe you could start us off. So Substack is a new media app. And, you know, the big version of this, we see it as we're building a new economic engine for culture. And so if you're a somebody who has something to say, a writer, a podcaster, a video maker, a publisher of any kind, Substack is kind of like your personal media empire in the palm of your hand. It lets you do all of that, own your work and make money through paid subscriptions. And for if you're somebody who wants to subscribe to the best media in the world. Substack is a tool that lets you do that. We've been growing for years. I think we can announce this is going to be, I think, relatively new when this airs that we've passed 5 million paid subscriptions. Oh, wow. Amazing. And, you know, tens of millions of people actively subscribing to Substacks. Amazing. Well, we're going to talk a lot today about the future of media and the future of Substack. But to begin and set...

set the stage a little bit, maybe we can go back in time and hear a little bit about how Substack started and why this was a mission that spoke to you. And I know that, Chris, you were sort of the person who looped it in with Hamish. So I'll let either one of you jump in there. But yeah, I'd love to hear a little bit about that. Well, I'd done another company before this. It was a messaging app called Kick Messenger. I met Hamish and Jay, who's our other co-founder there. And after I left that, After working on it for eight years, I was taking some time off. And I've always been an avid reader. I've always believed that the things you put into your brain, the things you read and listen to and watch are not just a form of entertainment. They shape how you think, how you see the world, and ultimately who you are. And so great media is valuable. And the people who make great media are basically heroes. I put too much shine on you, Mario, but I think the thing that you're doing here, yes, it's a podcast, yes, it's a newsletter, yes, it's a media business, but I think this stuff is important. It changes how people think, it changes how they understand the world. And yet a lot of the current internet, this is in 2017, didn't feel that heroic. The state of the legacy media was then and remains in shambles. We have these massive ad-supported social media platforms that... have tremendous business models and work really well for them and for advertisers, but are not necessarily aligned with the people making or the people consuming the culture. And so I went, I was taking some time off after my last company and I was like, I should be a writer. How hard could it be? And I was writing, you know, you have that good programmer's hubris. You're like, I know how to read. I know how to type. Should be great. And I actually started writing what was going to be like a essay or a blog post or a screed, kind of just like complaining about all this stuff. I was like, wah, wah, wah, you know, the newspapers are dying and maybe Facebook is bad, blah, blah, blah, blah, blah. And I sent it to my friend Hamish, who's actually a writer. And he let me down gently, or as he tells it, he gave me some notes basically saying, yes, it's okay. Listen, we know it's 2017. Maybe the legacy media.

business models are in trouble like this is not the shining new insight you imagine it is but the more interesting question is let's say all of that is true what what could you do about it like what would how could this be different and that sort of like became a that conversation turned into the original idea for substag which is actually the same idea we're pursuing today and it was both like you know a very grand idea And a little bit like, you know, a little bit grandiose. We're kind of like, ah, we're going to reinvent media on the internet and make a thing for culture and like put people back in charge of their media diets. But also we were like, okay, but there's this initial incarnation of this thing that people would want tomorrow that we could build. That's kind of like this very simple, humble seed of that thing, which was. let anybody start a paid email newsletter. And that was both a very sort of like practical, doable piece, but it was also like the thread at the start of this grand thing. Now, Hamish, Chris mentioned that you had worked as a writer. You were a writer. You were a journalist for many years. You've written books of your own. When you look back at sort of the media landscape that Chris was writing his screed about in 2017, If you had to trace back the sort of original sin, where do you see that coming from? If you could whisper in the ears of a young Mark Zuckerberg, is there something that you could have set us down a different path? Or the creator of the very first listicle, where do we start? Yeah, it all ended with the black and gold dress. Yeah, exactly. Well, I think these problems are not to do with any one actor or any one. the intention of any one person who started a new business on the internet, I think these are structural things. The internet came in and essentially laid waste to old business models that had traditionally supported media. And so it started with Craigslist kind of, you know, they took out the classified business that newspapers relied on so heavily. And then Google and Facebook came along and YouTube a little bit later.

And just were much better vehicles for the kinds of advertising that used to support other media businesses, even more so than classifieds. And so it was always going to be difficult for the traditional media businesses to recover from that. And it wasn't because Mark Zuckerberg was evil. It was our hell-bent on destroying the media and building something in his image. And then later on, actually, the streaming services have come along. existing television businesses, the TV news business, cable news, et cetera. So these old business models that were designed in the 20th century, maybe even the 19th century, are being attacked from multiple angles and by some of the greatest media technologies that the world has ever known. And they're great in the sense of extremely effective. They've got goods and bads and highs and lows with them. By the time 2017 rolled around, the physical illness that traditional media had was already well and truly set in and the body of that whole institution was getting weaker and weaker. And social media, which was physically very strong, had the business model that was really, really working, working maybe too well and bringing in billions of dollars for those companies that got to own the benefits of it. was sort of introduced into a world or like starting to reflect kind of a mental illness where people were struggling to understand each other and seek to solve important problems together and instead were kind of engaged in this fight for attention which the incentives of social media tend to encourage and so the things that you would do on these major news feeds, whether it's Facebooks or Twitters or Instagrams or whatever, were nothing to do with seeking truth or looking to understand each other, but a lot to do with reactivity and like really heightened emotion and kind of divisive type of engagement and community type stuff. So by the time 2017 camp came along,

Things are looking pretty grim for anyone who was considering a future in journalism or the media or as a writer. And no one was looking at writers as a potential customer base to hold up the next era of giant technology companies. Yeah, that didn't, I imagine, feel like an obvious bet for anyone. But I really love what you guys are saying around that it felt like such a big idea in some ways. You're playing with the grandest possible canvases of... billions of people connecting around culture and creating it together. But also you managed to find this thing that I would guess felt really small to a lot of venture investors when you started pitching it. And so I'm curious both how you landed on like that first sort of insight around, no, it should be helping newsletters run subscriptions and to sort of like, yeah, what the conversations were like with those first VCs. Well, there are existing examples. And there were, you know, there was Ben Thompson who had built Stratechery. There was Andrew Sullivan who'd done The Daily Dish. And so there were some existing examples of people who had, I guess, what we considered kind of shockingly good businesses. Like, you know, we did some napkin math and guessed that Ben Thompson was making over a million dollars a year, you know, from his bedroom in Taiwan writing this email newsletter. That's amazing, but it's like still too... You know, you saw the early signs, but that's like, you know, just two folks at the very tip of the of the spear. And it's not like they're huge businesses. Right. But here's the thing is if when you're starting out making something very ambitious, you try to make something for the entire eventual audience of it. That usually doesn't work. It's pretty hard. Sometimes you can get really lucky in that that that universe exists. But in my. estimation it's almost always better to start with something that's like the greatest thing in the world for like literally three people if there's a way that you can then take that and expand it to be 10 people and then 100 people and then a thousand people etc because if you start with something that's kind of like pretty good for a million people it goes nowhere

And it's not just like we didn't just sort of like take this on faith. We were thinking about we're thinking through why this was happening. Why is it that people are like, why would people pay for one of these things? What are the currents in the world that are causing people to realize that their, you know, their money is no longer their scarce resource? Their attention is they're not happy with the media diet. They're getting the deal that, you know, creative people across, you know, the whole Internet is getting is getting worse and worse in a bunch of ways. Like you have to be able to look at a thing that exists today that some people will buy, but then also try to like accurately or like make a bet. I should say you have to make a bet on where the where the winds are blowing, like where the world is going. And if you can get both of those things right, I think that's how you make change. Hamish, was that something that felt like it landed with the first sort of cadre of investors that you spoke to? Or did it actually take like, I don't know, a lot of. matchmaking to find folks that really resonated with that. Yeah, first we had to make it land with a few writers. And I remember in the early days we were saying you can use Substack to start your paid subscription publication. And it was just confusing enough that people weren't quite getting it. It was like, oh, do you mean like an academic journal? Do you mean like a magazine or something like that? And we're like, no, no, no. We didn't know what a Substack was yet. Yeah, exactly. Yeah, the idea of Substack was waiting to be introduced to the world. And we eventually decided to simplify it and just say, well, it's just like a paid newsletter because there's this email element and there's a web element, but you don't have to know all the bells and whistles before you start. And once we settled on the idea of saying we make it simple to start a paid newsletter, it meant we could go to all these other writers who are already doing newsletters on services that were designed for email marketing in many cases and not for writing, not for editorial.

and say, come over and use this thing. It's better. And you have the option to get paid by direct subscriptions. And we think this model can work really well for you. Once we had that story nailed, then it's a story we could tell investors. And some immediately got it and saw the potential. And some were like, who's going to pay for newsletters? How many Ben Thompsons are there in the world? And I think you don't need every investor to say, yes, you need some people to get it. And a couple of people early on, I remember Mike Kearns at Churning Group was one of the early. And Andrew Chan became an early believer later on. And that's all we needed. And, yeah, I think it feels like a small thing. Start a paid newsletter. Get paid for writing stuff from the audiences who care enough about it to pay. But that is actually a major thing. That is a big transition, the idea that you can have recurring payments for this and work that you consider important. And that the people who can get it will not just begrudgingly pay for that, but they'll be happy to pay for it. They'll be in this game with you. And once that becomes possible and proven, then all sorts of things are newly possible. There's a version of Substack I could totally imagine that is a really much smaller but thriving indie business. You know, the widgets to tip a creator or buy a cup of coffee or, you know, whatever those things are. We totally should have done that. Yeah, it sounds like it would be so much easier. Was there a moment where you had to like kind of kill that, you know, lighter weight version of things to really pursue the mission? Or was it always just, you know, no, we're going as big as we possibly can with this? You know, I'd had sort of a taste of this thing. at my last company where we kind of got to that, you know, hundreds of millions of people using it. And I'd say that experience maybe increased my ambition of what's possible. And so for me personally, the fact that I felt like we were onto something potentially quite big and transformative was the thing that made me want to work on it in the first place. You know, if somebody wants to make a...

tool for tipping on websites and it's a cool lifestyle that's a really it's a great thing to build it's interesting it's fun i could see why that would be a a worthwhile uh thing for somebody but it wasn't that wasn't the that wasn't what made me you know pour my pour my life into this thing for me there's kind of a like a moral impulse as well like if we felt like if this could work for bill bishop the first ever substack writer that's really interesting if it works with daniel lavery a totally different sort of profile to bill bishop who's writing for librarians and not business people. That's even more interesting. And then maybe this could work for lots of writers. Maybe this could work for all types of creators. That's super interesting. That's kind of like profound. That means that we're sort of unlocking energy from the universe that was previously hidden. And once you discover that, if that's true, you sort of, I feel like where it's incumbent upon us to sort of see how maximal that truth can be. Because that kind of thing can have a really meaningful effect on the media ecosystem, which in 2017, and today still really, is in a pretty dire state. Yeah, we weren't wrong about our assumptions. The idea that the internet was driving us crazy, we haven't become less convinced by that in the eight years since. So it's like you should go as big as possible. And maybe someone comes along and crutches you and does it better or takes over along the way. But otherwise, there wasn't a long line of people waiting to come and... help writers at that time or help the media at that time it was actually a lot of tech companies had come and gone had spent a bunch of money and tried different approaches at it and had failed and the common wisdom at that time was just that content the content isn't really a good business there's no like billion dollar tech company to be built on content I hate when people call it content. I was going to say, even the word content feels so unpromising, right? It feels so calorie-less. It begs the question. It's just, what is it? Oh, it's the thing that's contained. What are you talking about? The only good use of content I've seen is, I'm sure you've seen Patrick Collison's LinkedIn page that says content strategist, which is just a content strategist. Yes. Yeah, it must be. That's very good. I love this, the way you said this, Hamish.

unleashing energy from the universe. And today, when you look at Substack, it does just feel like this incredible energy has emerged from it. This incredible creativity has come from it. It's almost, you know, I think of it sometimes almost like a city where you have these different neighborhoods. You have the, you know, the food folks, the culture folks, the business folks, and actually those people, you know, sometimes cross over, sometimes they stay where they are. You know, sort of with that metaphor in mind, I don't know how good it is, but. Which were like the neighborhoods that you were really shocked to see pop up in the Substack City? And which are the like, you know, maybe the empty lots where you're saying you have an eye on them and say, actually, we could really we could really see something amazing happening here. I mean, I'll tell you early on, there was a real question that, you know, investors and even we had was, is this going to work for anything beyond business? Because it struck. I mean, you know, you've got. Bill Bishop, you've got, we had a bunch of people who were making kind of like, you know, things that you could pay for that could help you with your work and that you could conceivably put in a corporate credit card. And that felt like a pretty well-established thing. But it was, it was, it came as a, not a surprise, but sort of like a pleasant development to us that actually a lot of, you know, that stuff is still doing very well on Subsec today, but it's a minority of what's on the platform. There's a lot of stuff that's working really well. I guess there's more. I kind of think of Substack as an index fund of culture. And for everything that there's somebody out there that's really into, there's usually like something. And there's just people are into more stuff than I would have been able to think of or list. One thing that I do think we, I wish we were stronger on, and I think there's people doing it and they're doing good work, but I think the platform could do a better job of is just fiction in general. I think fiction is really important. I think the idea of serialized fiction is well developed and could work well. And I think the overall preponderance of fiction on Substack, I think if we could crack the code on it, could be higher. You might have seen my eyes sort of light up when you said that. One, because I know you're the son of an English teacher. And so, you know, that's, you know.

your your your good uh your background uh doing excellent work there but two because i think that's you know feels such like such a big opportunity that no one has really nailed uh i i was i really enjoyed the article uh the substack the substacker l griffin wrote about no i think it's called no one will ever read your book and it sort of breaks down the state of the publishing industry especially for fiction and how just like you know very very tough it is for anyone to crack it and she's since crowdfunded a book successfully on her sub stack i i just invested so i'm a i'm a small participant but yeah it feels like there's such an interesting opportunity there like what do you think the the right way to sort of make that it's a cultivate that further looks like maybe hamish you can tell us a little bit about that gonna make us uh write some checks here that we can't promise on cashing in the immediate future um Well, we've already had people serializing books on Substack to some success and then get traditional publishing deals at the end of that serialization where the book becomes this physical memento, this monument to the work and that gets exposed to new audiences in that way. We've had people who write their draft in public. A lot of Jonathan Haidt's The Anxious Generation was first published on Substack for his Substack after Babel. I think there's kind of interesting ideas around like community participation in a book where you publish chapters or you publish as you write and you get feedback from people and keep on adjusting the narrative in response to the feedback. I think there's ways that the product could evolve to more perfectly suit this style of publishing. But already what you've got is enough for something super interesting. I'd love to see books live on the web in the future as well. I think it's kind of criminal that books don't. live on the web. You can't have a website version of your book. Something like Substack allows for that because if you want to make money from selling the book, you can still put certain chapters behind the paywall and then have it read out to you by the AI voice that's really high quality. So I think there's tons of room for experimentation and exploration within the Substack model, within the Substack platform for books. We've already seen plenty of success cases.

And I think we're going to see a lot more. And we'll keep evolving the product to perfectly suit those needs, won't we, Chris? I'm not trying to pin you down to anything in particular. But you mentioned how it's worked for different books. And I've seen some really interesting projects over the past few weeks in particular when I've been learning about this a bit more. For fiction in particular, do you think there are certain things that are required? You mentioned... writing in conversation with your audience. I always think of Andy Weir in The Martian where he sort of wrote bit by bit on his blog and then that has since become a massive hit. Yeah, wondering if that type of storytelling in particular requires different tools. I do think there's some practical stuff that we could improve. One thing I think about a lot is because Substack started in and still has a major component that is email-based. A lot of our metaphors are sort of email-driven, right? It's like you get a new thing. When I subscribe to somebody, I get a new thing in my inbox. The new one's at the top. And I've read fiction on Substack before. And the problem that happens to me is I'll start reading it. I'll read the first chapter. I'll get the second chapter. I'll read the second chapter. I'll get the third chapter and I'll not read it immediately. And then next thing I know, I'm getting the seventh chapter. And so my new email is like, here's the seventh chapter. And I'm like, oh, wait, I got to go find the third chapter or like, where am I in this thing? And the fact of like getting the cereal like in slices is not actually the ideal way to get it. And if we were solving that problem, the thing I would imagine is, you know, I might have one updating, you know, that thing should actually be grouped into one logical story. It could update as it goes. It could bump up when there's a new one, but it would remember me as the reader where I am and help me kind of go through it in the right order. I think that would actually go a long way. Yeah, I really believe there will or can at the very least be a future in just the same way that you have Netflix and Amazon that wins Oscars. Maybe there will be a National Book Award winner that was first published on Substack. Sure. And you could publish, I mean, you could publish a TV show on Substack too now by the same token, right? And you would want it to work the same way. You want it, you know, if I go to the...

The Netflix remembers where I am. It remembers what episode I've watched. I could pick up where I left off. That's just what people expect now. And I think it's more important for fiction because reading it in order is more important and reading it in a timely fashion is less important. That's really true. You mentioned, you know, with TV shows and one of the things that I think you guys have done so interestingly over the years is sort of progressively expand into different mediums. You have podcasting now, video, chat. short posts, each of those mediums sort of has their own strengths and weaknesses, you might say, their own little flavors. How have you thought about managing potential tensions or trade-offs between those different mediums while trying to retain the parts of Substack that make it unique and make it special? Yeah, one way I put this is that a lot of other platforms that you might think of got built up around a format. And so, you know, Instagram was pictures and Snapchat was disappearing pictures. And then TikTok was short form and so on. And Substack is not built around a format. Substack is built around you. It's built around the subscription relationship that you have. And being able to unlock that to be every format that you want to use is a, I mean, a design challenge, right? It's hard to make an app that has all of these different you know short form social media posts and long form articles and podcasts and videos short form videos and like maybe others like chat there's all these things uh it's hard to make a put all those together into one package in a way that's coherent. And I actually think we still have a lot of work to do on that. I mean, the thing we've kind of done is we've built a bunch of these things. They're all kind of working. It's exciting. And then sometimes when you open the Substack app, you're like, oh my God, what's happening here? There's so many different things. So I think we have still some work to do to kind of bring it together into a simple package. But listen, our thing ultimately is you should be able to create in every format.

that you care about and reach your audience. And you shouldn't be limited to, oh, I've got a subscriber on this platform so I can only ever make videos. I can never write or vice versa. And in the world of all of these new AI tools that are coming online, it's getting easier and easier to get creative leverage, right? The idea that you could have an AI that you talk into your phone and sort of magically turns it into like a usable artifact is possible now. You can already... read, you know, listen to things that are written in the Substack app with like a great AI voice that sounds awesome. Like all of these things are becoming easier to translate from one medium to another to sort of like make highly produced stuff in audio and video without having to, you know, hire a team of nerds every time. It's a new world. It's exciting. I certainly want to talk more about AI at some point. But Hamish, I'd be curious for your take on the fact that, you know, Substack was certainly created in response to the fact that we sort of have spent our attention pretty badly over the past decade plus on short social media, short videos. Do you ever have a worry as a writer yourself that as that sort of starts to come into Substack, because it's so addictive or because our minds seem wired to want to consume this, that actually short video ends up taking time away from people reading? the you know great piece of fiction or you know george saunders story club whichever these uh great pieces of culture that are that are on substack um you know you know sort of shifting that that focus a bit i'm actually really excited about what's possible when you get that short form feed and discussion and discovery in the context of substack where everything is based around deep relationships that leads people when these things are like the front door opening up to a path that leads people down to a subscription or like a kind of relationship with a creator or a writer who they really care about. I think what we've seen so far is that those kinds of technologies, the Twitter feed, the Facebook newsfeed, Instagram, YouTube, et cetera, are extremely powerful. People are going to spend their time there. TikTok is the latest one. And they're going to spend their time there, whether we like it or not.

I'm going to spend my time in lots of those places, a lot of those time for like my snacking time, my relaxed time, my casual browsing time, even though I love to read books, even though I love to watch documentaries. And given that that is true, and it's very obviously true, these are the platforms that culture is happening on to a large extent, and there's billions of people using them. Wouldn't it be interesting to see what happens if you rip the ads out of them? And give them the job of maximizing these deep relationships instead of maximizing how much time someone spends doom scrolling. And I think what we're seeing in the Substack network is that that can create something pretty fucking interesting and a different type of experience in those feeds. When you leave the Substack feed, you don't come away feeling dirty. You don't come away feeling like you misspent your time. And you've actually likely started a bunch of interesting relationships either by casually following a creator or actually fully subscribing, maybe even paying to subscribe to a creator who you might not have known about otherwise. So that's really exciting to me because I think it lessens the grip that those other platforms have on society's mind. And it strengthens and gives power to the types of creators who are doing quality work. and just need to help that work, just need some help finding those audiences who are going to deeply appreciate that work. Anecdotally, I will say that you phrased that perfectly. When I use Notes, for example, which is, you know, the sort of Twitter equivalent on Substack, I don't feel dirty. And I'm not really sure why. I haven't really totally cracked why it feels like a different experience. Maybe it is the absence of ads. Maybe it's just like... Elon's not on there yet. He's not on there yet. He's probably somewhere on there. I will make the subtle distinction that it's not just the absence of ads, although personally I hate seeing ads. It's annoying to me to have my experience interrupted by ads. But the ads warp the incentives. The ads change. The advertising being the business model that makes those whole companies run mean that they have to point the algorithms for their feeds.

at the things that serve the advertisers, not the things that serve the people who are consuming the culture and who want to connect with great creators and consume great video, audio, text, whatever. And so it's like the difference between an internal combustion engine car and an electric car where they kind of look the same, right? But the experience of driving an electric car where there's no gear shifting and there's just pure, smooth, instant acceleration and torque distribution. is so much nicer and so much better than driving an internal combustion car, which is predicated on all these explosions happening under the hood of your car. And the externalities, the external outputs are also completely different. Like the gasoline car pollutes the atmosphere and electric cars are much friendly to the environment. Same with the Substack feed versus the other feeds. Do the other feeds end up polluting your mind and the Substack feed maybe can even cleanse your mind? Can even cleanse your mind. That's a new tagline. Cleanse your mind. Might be an overpromise. But you don't come away feeling so polluted. Let's leave it at that. Yes, absolutely. And, you know, I think it's interesting. Just from like a pure business strategy perspective, I think Notes is such an interesting and intelligent sort of addition to the platform because it is this top of funnel. But as you said, the pipeline is working in your favor as a writer or a creator rather than sort of against you, where, you know, certainly on Twitter and X, you know, you can you can go viral, let's say. And I would sort of very carefully chart how many subscribers did that create and how many paying subscribers did that create? And it could be a really tiny number because, you know, it's just such a diffuse pipeline. And so, you know, that's such an interesting thing from a creator's vantage. It also, I think, brings up the conversation, the Internet of Beef's, you know, battle royale between Substack and X. You know, for those who maybe didn't follow that chapter closely, can you explain sort of why there is some degree of...

intense competition there and how sort of creators maybe got caught in the crossfire a little bit. Sure, I'll tell the original story. Elon Musk bought Twitter a couple of years ago. And one of the things that he had his eyes on early on was bringing Substack into the Twitter fold more. He actually thought that these companies could work really well together. And on the face of it, it seems like they do complement each other. Lots of people discover Substack through Twitter and then go on and pay to those. uh creators on substack and i think elon's view was probably like well substack is effectively acting as a paywall for twitter that these two things should just be together and so he tried to convince us that we should join forces in this way we actually have like a different vision of how this all should play out and we like the more integrated system that substack has where there's not like an ad based feed that has sometimes uh competing interests with the deep relationships feed or the deep relationships platform and so we're like We're not eager to do that. And in the meantime, launched our social networking type feeds, the Notes product. Gave Elon a courtesy heads up about it the day before we did that. And then when it came out the next day, people on Twitter freaked out and said, well, here comes the Twitter killer. Substack's got the Twitter killer, which is not how we were positioning it. You can't just instantly make an amazing social network on day one. It takes time to build that ecosystem up. But it didn't matter to Elon. He saw it as a direct shot across the bow and mute Substack from Twitter essentially. Immediately cut us off from their API, suppressed all the links that were going to Substack publications. Even for a couple of days, you couldn't search for the word Substack in Twitter. It would just return results for a newsletter. He accused us of stealing data in the meantime, which is totally bullshit. We were just using the API in a normal way. But that created the impression that there was this big beef going on. But to us, it was kind of like, we're Ukraine and Putin. He just decided to start bombing us. And we're like, why are we getting bombed? We're just trying to build this ecosystem. And it hasn't hurt. Way to take the temperature down by using a neutral metaphor. Yeah, yeah. Sorry to all the Russia fans. So we just continued, essentially. Twitter was already becoming...

a less important share of traffic for Substack publications. It was really painful for a few, but it was a good thing to happen for Substack ultimately because it forces Substack to continue building the kinds of things that help writers and creators on the platform grow without making them dependent on these capricious and volatile social networks that don't really have the creator's interests at heart. They're mostly focused on their own platforms and the advertising. That's basically what happened. I think Elon's interest has moved on to other things at the moment. He's got a few things that is on his plate. That beef has become like a small medallion on the corner of his vast plate. Yes, his very vast plate. You mentioned that there was some point where there was the discussion about how you guys maybe would work together. Did you ever get to the stage of thinking, actually, maybe there is a way to do that in a deep partnership or even an acquisition. to that sort of level of conversation? It's not something that we were keen on. You know, we've always wanted to build Substack as a successful sort of independent endeavor. We think we're building something wholly new. And when there's been conversations about, hey, should we join this or that company? I think in general, it would break the thing that we're trying to accomplish. Like philosophically, these are such different businesses, right? Yeah. I think it would be hard to make the thing that we're trying to make in a context like that. And we are seeing this now. We've been working on the Substack app and this network concept for years and years and years because we knew it was going to become critical. Because in the early days of Substack, like I think when Elon did that, he thought he could sort of kill Substack. He thought we were wholly dependent on it. And although it was, I don't want to diminish it, it was very painful for many, you know, Twitter users who had Substacks, who like had this thing. It was no fun. But from a systematic level, it was basically a rounding error by that point. Like it didn't matter. But there was a time like in 2019 where that actually was true.

basically everything on Substack was downstream of, used to be able to like tweet out a link and everybody would see it and you could get like, you know, that experience you were having, you get like a ton of subscribers. And so a lot of our early growth was driven by this effect, but we knew there's two problems with that. Number one, you're still just downstream of the Twitter incentive structure then, right? If you're saying my whole business depends on my top of funnel coming from. this other network i still have to play the game of that other network and i'm still kind of like beholden to that incentive structure and then the other part of it is just practical it's like well it's not really in there they don't care about your business working in fact maybe it's a negative and so you saw this kind of and not just from twitter but you know they blocked us but then since then they've it's basically all links are deprioritized i don't think subsec even gets particularly special treatment anymore We've seen all kinds of vagaries meta for a long period, went through a period where they just didn't allow any political content because they're just like, we don't want this. And, you know, fair enough. But then if you're a political journalist or podcaster, like, what do you, what does that mean for you? And so, you know, if you want to, if you want to, we want people on Substack to be able to promote their work on every place, like put it everywhere, have a, have the podcast feed, put it on YouTube, put it on Twitter, put it on TikTok. Like, of course. But you don't want to be wholly dependent on any of those things. You want to have at least one place where people can discover your work in a way that actually wants them to find it and fall in love with it and go deep on it. And that thing working is a big part of why, you know, that you use that city metaphor that says I can kind of feel this way now. You kind of have this sense of like, there's a whole set of stuff out there that I can go and find. That's happening because there's this, you know, this discovery. piece of the equation where people are proactively coming to Substack to keep up with the things they're subscribed to and love and then find new things to fall in love with. And you're talking before about, I'll add one more thing to this before I completely filibuster. But you're mentioning like the, is there tension between short form and long form in that? Like by adding the notes feed, does that, you know, is there some trade-off of like some time that I spend on Twitter, I could have spent reading a book instead. Like what's the deal?

I actually think I can see where that comes from. And like at some, at some logical level, like that's true. But in practice, I think the reverse is closer to true. Where if we built the, you know, if we built Substack to be the eat your vegetables platform that says there's only going to be ultra long form dense works of, you know, extreme journalism here. The net effect of that would not be that all of a sudden there'd be way more steep long form stuff. The net effect of that would be much fewer, many fewer people would use Substack. It'd be harder to make money as somebody working on Substack. And so as we've been building the discovery feed, the thing we've seen again and again is there's, when you do something that's good, when you actually make a change to it that really works, you get these like across the board wins where it's like, hey, we made it better and people saw more things in their feed, but also they read more long form posts, but also they discovered and subscribed to more things, but also they retained better and came back more often, but also they paid more money. Like there's sort of like a version of this thing where when you make it actually genuinely good, you know, you don't have to be a monk to read interesting stuff on Substack. You just kind of show up, you've got this feed, but then in your feed, there's like, oh, here's this quote from this really interesting article. I click into it. Now I'm reading this interesting article. Then I read the next one. You can kind of like make a universe that's helping you go deep and helping you become a better version of yourself by giving you something compelling instead of giving you something compelling to try to like erode your your attention span in your mind we're such magicians that we can trick you into being a decent person we will trick you into reading quality writing please decent persons too is an over clam we can trick you into reading and watching and listening to good stuff the that's good enough for us i remember when we were chatting Back in 2023, when we brought a case study on Substack, you guys talked about how you think of, you know, the company as a tool, a network and a destination. And I think what you're saying there is really like that network and destination piece really helps every other publication on there. You need it to be a destination to drive all of these people in. And then those people do, you know, find these great pieces of content, even if, you know, it's totally fine that they also engage with shorter form things as well.

A great example of one such platform exists, and it's probably the best one for media on the internet at the moment, other than Substack, which is YouTube. Not only a giant business, but a place like quality stuff, historic and contemporary, where people are bound in these relationships. I actually think that there's lots of room to improve on YouTube, though, because those relationships are still ultimately controlled by the platform itself. And the monetization is only based around, well, it's primarily based around advertising, which sort of sets terms for who can be successful there and what gets made and how it gets made and how it gets presented. Whereas the Substack version of YouTube is based on deeper relationships and direct subscriptions that directly support the creators who are doing the work. And I think that's going to create something pretty special. And we've just seen the beginnings of it. This episode is brought to you by WorkOS. What do companies like OpenAI, Cursor, Perplexity, Webflow, Plaid, and Vercel all have in common? They use WorkOS to power enterprise features like single sign-on, directory sync, and multi-factor authentication. WorkOS is set apart by its modern APIs and SDKs for seamless enterprise integrations. Plus, it's free to get started. Whether you're a scrappy startup or rapidly scaling, WorkOS has the solutions you need to secure enterprise deals. Future-proof your authentication stack with the identity layer best suited to meet the evolving demands of enterprise environments. Find out how at workos.com. I think people don't fully appreciate how the monetization on Substack differs from YouTube, for example. You'll remember the Substacker who wrote this piece recently, but there was a great piece on Substack about... you know a prominent youtuber who you know does food youtubing and built like a really large audience like 250k subscribers producing fantastic videos and absolutely could not make the economics work was you know effectively losing money on every video for a couple of years uh and you know having that direct relationship with a subscriber totally changes that

That's right. That's Carla Lally Music. And she's a food professional, like a chef and media personality who came up through the Bon Appetit Test Kitchen. And she started on YouTube like three years ago. She had something like 18 million views in aggregate. 200,000 people liked her stuff enough that they clicked the button saying, yes, I want to see her in my feed all the time. 200,000 people is a sizable audience by any measure, except by the... You can only make money through YouTube ad share revenue type of measure. And so she really was making high quality videos, but it was a grind. It was a hustle and a grind. And what she ultimately decided to do was to shift all that attention and energy to sub stack where that kind of audience can really sustain you. And the economics of direct subscriptions are totally different in terms of the order you must reach to. become interesting so she makes far more money on substack for far less production intensive type of work that doesn't negate the possibility of doing these beautiful videos where she gets to build over time and can make money really fast uh like i don't mean well yes it can increase fast but like the the time from starting to get to sustainability with a subscription model that depends only on a few hundred or a thousand people to support you to make it enough to live on is so much shorter than the time it takes to build up a giant enough audience that it becomes interesting for advertising. And so I think that that's a super interesting case to look at for kind of the potentially transformative effect of going deep with devoted audiences rather than trying to do the old model, which is to go wide for an audience that is kind of casually interested and some third party comes in and monetizes it and gives you some scraps from the table. Chris, you were mentioning a moment ago how important it is to not be locked in by these platforms, whether it's YouTube or anyone else. We had a really interesting sort of case in point of that earlier this year when TikTok was briefly shut down in the U.S. And Substack sort of leaned into that moment, it felt like, from outside and was able to bring some TikTokers into the Substacker fold. Can you tell us a little bit about that moment and maybe what it meant for the business? Yeah.

One of the things that Substack offers, as you know, is ownership over your audience. So when somebody subscribes, you get their email, you can import emails to your Substack, and you can also export them. So if you decide for whatever reason Substack is not working for you, these are your relationships. You can take it to another platform. You can reach out to them. You have these kinds of options. And we've always felt like that's important. We think of it. you know, primarily as like exit rights, right? Like if part of the reason you can trust Substack is because if we start to like turn evil, you have this right to leave. And that just doesn't exist on other platforms. And we, you know, the drama around the TikTok ban, we felt like was just a moment that was taking that like abstract idea and making it really suddenly real for a lot of people, you know, whether, and I think it's still unclear what's going to happen. to tick tock in the long run but whatever happens i think it just caused it to be really front of mind definitely for youtubers but also for people on instagram and on youtube saying like oh yeah if this platform shifts or changes or you know goes in a direction that's not the direction that i want to take my work what's going to happen to me and so we went to a bunch of tick tocks and said hey you should start a sun stack and you know at least you should collect an email list so that you have this list. But also we've built a bunch of these really good video tools. We have this very easy to use live thing that goes right from your phone. We've got this thing. And we had a bunch of people launch, some of whom have been extremely successful. Maybe the case study for this is Aaron Parnas, who was a very famous political reporter, TikToker. News TikTok, right? He's sort of like a TikTok news personality, yeah, who would translate the political news over the day for his audience. None of the three of us are huge TikTok natives, it feels like. There's probably some sharp leader there. During this period, I also created my TikTok account and started making TikToks. Oh, God. I went viral once. It was thrilling. You did? What did you post? Well, not very, but I just, I don't know. It was a sexy dance. Here's why you should start a sub stack.

But yeah, and he's, he's got a, he's got a sub stack now and it's, it's, it's going gangbusters. It's this, and it's, I think, you know, if, if I'm, I'm reading some of like the notes he's posting about it and we've talked, but basically it's like the thing that it feels like it enables him to do. Right. It's not just because when you make money through subscriptions, it's not just about like how much money it is, although that obviously matters. The money hits different, right? The fact that people are there supporting you because they believe in the work. means that you can make your money doing the best work, not just by trying to go viral or trying to hustle for sponsorships or trying to do whatever thing. I think it has felt like it's transformed for him what kind of work he can do and what kind of ambition he can have with it. And I think that there are a lot of people on other platforms of the internet. It's not everybody, right? It's not that everybody on TikTok has an audience that's champing at the bit to subscribe to them. or on YouTube, or on Instagram, or on anywhere else. But a lot of them are. And they're disproportionately ill-served, right? The people who have maybe not the most enormous audience, but whose audience deeply values what they're doing, those people could not just have the benefit of having an email list and all this stuff. They could make more money on Substack. And so we're working on bringing the word to them. Well, I'm sure you will. When you sort of project forward five, 10 years, imagine that we do have so many folks from TikTok aboard, you have great food folks, just several orders of magnitude bigger than it is today, let's say. What does the sort of consumer behavior look like? Will people just have to get used to the fact that a larger percent of their budget goes towards information that otherwise was free? That, you know, people do start to bundle and that becomes an important part of it. How do you think that plays out? People are already willing to spend money on culture that they value. And it's not because they're not dumb to do that. They're smart to do it. If you think about, you know, if you listen to an hour-long podcast or you read a book, what is the opportunity cost that you're paying in?

your time, your life, your attention for doing that. And if you could pay a couple bucks to get something that's a more valuable return on your time and your life, is that worth it? And I think there's like a very large number of people today for whom the answer to that is a resounding yes, but who have not yet had the opportunity to do that. And so I think first, like the highest sort of part of this is like, As a society, investing too much, too little, or just the right amount in great culture and rewarding people who are making valuable media, I would argue we're paying way too little. And there's a much higher ceiling than what we have today. People are going to pay a lot more. And they're not going to grasp it. They're going to feel like, this is great. I'm able to get all of the stuff that I really care about. I think there's some limit. I think there's ways that we can work on making it like... making the economics of it kind of like maximally favorable to people on both sides. But I think the highest order bid is just like it's worth paying for things that are good. Yeah, I'm interested. I wonder where that share of wallet ends up coming from, even if we say, OK, you know, that obviously can't scale limitlessly that people will just spend all their money on information as much as my gimlet eyes at the generalist would love it. You know, does it come out of sort of traditional education where people are saying, hey, you know, it's actually much less important to me to spend a hundred, you know, several hundred thousands of dollars on university when I can, you know, really learn how to code or learn how to invest or, you know, learn whatever it is from sub stack, you know, several sub stacks that I subscribe to once a month. Hamish, do you have any thoughts on on where that share comes from or how you think that plays out? I think we should get Chris to talk about his grand theory about how the economy changes as AI starts to eat more jobs and how that shifts the spend as well. I think that's probably an interesting place to take it. But people have a history of making room to pay for culture they care about that no one used to pay for Netflix. I guess it's shifted from cable a little bit. No one used to pay for...

I guess I was about to say Spotify, but I guess that shifted from buying records individually a little bit, but it probably contributed to increased spend in other ways, like on shows, on merch, etc. But I think the AI revolution take is a pretty interesting one. It's a good time for a grand theory. Yeah, let's give a grand theory, Chris. Okay, here's the grand theory, which is technology in general makes things... better and cheaper like if you allow technology to be applied it makes things better and cheaper and you know i think we could depend you can you can calibrate to be how much of a believer in this stuff but i think you know ai is this insane general purpose technology that we're just at the start of starting to kind of like apply to the real world and i think some people you know some people even people who are in the ai space deeply understand the technology, but haven't, you know, haven't grasped the economics side of this that much because they're sort of like, ah, like everybody will run out of their, we'll have no jobs anymore and we'll need to like, whatever, have some UBI thing for all the, but that's not actually what happens, right? What happens as things get better and cheaper is the economy adapts. There are other things that get more expensive. Basically, the pieces that are not getting whatever pieces are not getting automated. There's a thing called Bommel's cost disease if you frame it in kind of like a negative way. But it means that, you know, as the opportunity cost, as everybody gets richer, as more things happen, the things that are not touched by technology just get more expensive and take up a bigger and bigger share of the economy. Then you can ask, okay, so what is AI and technology going to do to media? And on the one hand, it's going to make, you know, it's going to make it better and cheaper, right? It's going to make it easier to create content. If you want to make a highly produced piece of media, if you want, like you're going to get to a world where, you know, two people could make a feature film in their garage and it's going to be like better than anything you could have made, you know, a decade ago.

And so on the one hand, you're going to have the same effect where all of the stuff gets cheaper to make. And if you, if your view of the purpose of media is to be kind of like a drug where it's, it, it, it just, it's, it's effect on you is the only thing that you care about that. What you're going to have is you're going to have like magical, you know, AI media wireheading, wireheading being a science fiction concept where you can kind of like. You know, you, you just watch like super AI tech talk. That's a hundred times more powerful than human tech talk. And you just kind of like, you know, bask in this glow of thing and it kind of cooks your brain for you. Endless free drugs. To some, yeah. Endless free drugs. That's probably going to happen to some extent. Yeah. People are going to do that. That's going to be a great business. You know, is what it is. But, you know, in my mind, that's not actually the main purpose of media and culture. media is not just about getting what you want. It's also about learning what to want, right? It's shaping how you think. It's shaping what you value. It's shaping who you become, right? Ultimately, you know, the media culture, the conversations we have, these are like the human alignment problem. They're not solved. And so as the price of, you know, the cost of generic content falls to zero, Which, by the way, has already been happening. We already have the internet. There's already more things to read than I could ever read, more video to watch than I could ever watch. And that's just going to get even more extreme. And the stuff that I can't watch is going to get higher quality. But in that world of information abundance, the relationship that you have, if Substack is about people, the relationship that you have with people you trust is going to get more valuable, paradoxically. because you need to know how to curate your attention. You need to know what to care about, what to pay attention to, what to spend time on. You know, you want it to be a multiplayer game. You want to be participating in a culture that other people are participating in. You don't just want to have, you know, there will be people that just have fake AI friends and that live their whole life that way, but that's not what everybody's going to want. And so in that world, you know, as this Bommel effect happens, I think you could have kind of like a benign version of it where

The creation and participation in human culture becomes actually a larger share of the economy as all of the things that are kind of like can be made cheaper and abundant, get made cheaper and abundant. And in that world, what's the right amount for people to spend on subtext? I think it's much higher. I think it's an exciting future. It's as AI slop and AI entertainment sort of. takes over, you know, yeah, the entertainment piece of media, the part that gets more valuable is learning what to want, learning, you know, who you want to be in and sort of curating your information sources. And in that, humans play an outsized role. And so you're sort of picking those influences on yourself. Is that is that a fair summation? Yeah, basically. And, you know, we're going to need new cultural norms to deal with all this stuff. But yeah, the trust relationships that I have become more valuable. Hamish, when you first heard the grand unified theory, what was your response? How much do you buy into that worldview? I buy into it a lot. It pumps me up. I think I've always thought that writers are more important than developers, which is something I said. I agree, of course. He tells me that every day. Gosh, this is like the only company where you have to listen to that and take it. Yes, the writers are the kings here. Maybe he's too strong. Writing, obviously, being the greatest technology that humans have ever invented. And so in the sense that we are a writing company, we're a technology company, but we're all of culture. It's not just writing video, audio, et cetera. But I also think that's at the heart of what it means to be human. This is the way we evolved through. leaning on each other through evolving together as social creatures with strong social bonds and that the sharing of culture and storytelling is essential to that very bond which is like at the center of all of human existence and so the the like to get even like more grandiose and airy fairy about it the the thing that gets valued in this new economy is less that like i get something i get a piece of content from you or i get a piece of

content from some machine. It's more about soul connection. I know that there's another human on the other end of this and that when that human thrives, I thrive too. And then we grow together. So I completely buy it. I buy it on the new agey type of level. I buy it on the economic level. I buy it on the technological level. And I'm excited for that future. And I think it's a future that's worth building towards and a future worth feeling hope for. I hope all the generalist listeners Like and please subscribe to my soul connection because that's the future that we're talking about here. Just one more point on the AI front before we maybe talk about, you know, media landscape today. What are the like accretive ways for Substack to lean into AI? What are the places that it makes sense for empowering creators with this technology? Well, I think anything that. is giving people creative leverage is an obvious place to lean in. You know, one of the things when we started with writers, there was a bunch of things that were good about Substack, like the business model's good, you can make this money. But one that I think is maybe less obvious is just the fact that we kind of like made it really easy. If you're an individual person who is a great writer who has something to say, that's hard enough and rare enough. And there were people like Ben Thompson who happened to have something really good to say and be technologists and product people and entrepreneurs and be able to kind of like invent this stack and this thing for themselves. But there's a lot more people who just have something to say. And so one of the things with Substack is we want to have this sort of Promethean instinct to say, we're going to just bring this power to you and make it really easy. If you're a great writer, come and type into this box. And if the thing you type is great, which is hard enough, but if it's great, you're going to get rich and famous. This is a magical machine that's going to take care of the rest of the things for you. That's what we aspire to. Yeah, there's a big settings page you have to go to sometimes. But that's at least the animating spirit of where we're trying to get to. And I think something that's happening not in the distant future, but is currently today very possible, is you can do that for many more kinds of media.

So we have an example of this. We're working on this live product where you can go and open the Substack app, call someone up and have what's effectively like a FaceTime call with them. And it gets broadcast live. Your subscribers can tune in. That's cool. But the most important part of it is it just kind of like sets this expectation that you can basically just show up and like talk into your phone. You just go and say, hey, it's like I'm calling you. Like, what's up? How's it going? And then because we have this new suite of AI tools, we can in the back end go and say, all right, take this thing. Oh, they didn't have the perfect microphone. Okay. AI fixed the sound. Oh, it was the front facing iPhone camera. Okay. Turn it into a high quality thing. Fix the lighting, make it look great. Okay. They went and did a long live, uh, go and just like edit it, cut out the boring parts, find the clips that are really good. And so there's, there's going to be this, you know, what used to be possible only for writing you're going to have with multiple different media types where I can just kind of show up and. talking to my phone. And if the thing I have to say is great, I can get rich and famous. I can make a million dollars. You know, Jim Acosta was a CNN anchor who quit CNN. His only computer was like the company computer. They took it away. He didn't have a laptop anymore. And he got the Substack app on his phone and he went live and just did it by himself. And got an instant media business out of it. People showed up in droves. They were excited to pay to subscribe to support him and get what he was purveying, which is he hasn't paywalled any content, so no one's getting content that they're paying for, but they're paying for that soul connection. And Talks to His Hand has an instant media business in the space of seconds. Because the face don't give a damn. Sorry, that's the 90s kid at me. Never mind. Please keep that. Don't cut that. Cut that part out. Don't cut that. It's genius. That'll be the clip we lead with. How far do you think you might go or do you see the possibilities of going around new mediums, for example? There could be a version of this where the writer brain in me is like, well, there could be really cool text adventure games that artists might want to create. What are the constraints that are important to keep?

before things get too unwieldy, maybe? I think it's really hard to predict. I think we're in a period right now of genuine technological advancement, genuine discovery. And I don't think anybody can accurately predict where it's going, what's going to work. I think you see very interesting things where the state of the technology has progressed way ahead of how we figured out how to use it. And so the classic example of this is you had GPT-3, which was this amazing, you could look at it and say, this is crazy. It's unlike anything we've ever been able to do before, but kind of like, I don't know how to explain it to my mom. And then you give it this chat GPT wrapper that's just like, oh, the thing you want to do with it is talk to it. And then boom, it takes over the world. I think there's going to be stuff. like that, that happens in media. I don't think we know, I don't think we even know what all the formats are going to be. Um, and I think the only stance you can take or the stance that we take right now is kind of just like being willing, being open-minded and being willing to kind of like play and explore and watch and like test the fences, push the boundaries, see what's becoming possible, see what's working, kind of like be willing to be on the forefront of change as it happens and to like bring those bring the latest cool stuff back and like give it to people in a way that they can actually wrap their hands around and use it. There's a lot of things, right? There's a lot of things that are possible right now that if you like know how to use hugging face, you can like get AI models to do, but it's just like, it's the, it's taking that and like making it actually accessible to people is like a very, there's a very powerful moment right now for that. Yeah, there's still several layers of friction. You also asked what has to be the constant, the nucleus that sits there and is always true for Substack, and that is kind of the model. This model that gives the creator ownership and power, that they can totally own their audience and export it from a mailing list, that they get supported directly by their audience, and that the platform that undergirds it, which is Substack in this case, can only succeed if they succeed.

And if you keep those three things in harmony, then all sorts of expressions of culture and content are possible as long as that thing is stable and constant. Hamish, as an old media person who became a new media person in my 40s. I was waiting for it. I knew it was coming. But became a new media person and at the vanguard of this movement. I'm curious how you think about the positioning of these. prestige brands of the past and present. If you were to be airdropped into insert prestige media brand here, The Atlantic, The Economist, The New Yorker, what would be the things that you would do in your 100-day sprint to try and prepare these publications for the next couple decades? I think something that's core to their identity doesn't have to change, which is to maintain this. these high-quality standards and journalistic ethics and retain this sort of prestige aura, but accept at the same time that their general reach is going to probably shrink. They're not going to be able to command the kinds of audiences that they once did in the heyday of these publications when there are fewer options and fewer choices for audiences. I think those things, like the best of them can always have a place. A lot of them will continue to struggle and many of them will probably disappear over time just because they have this business model sickness that is going to be impossible to recover from. The world is different in 2025 than it was in 1925 when a lot of these things were born. But there is also ample... opportunity to rebuild to build the institutions of the next era things like the generalist or the ankler or the bulwark or the free press all of which are being built on substack and can benefit from these tools that let you create an instant media business and then plug into a subscriptions machine which is the substack network the notes feed the recommendations etc that helps you grow just by dint of being part of this enormous community

And I don't think there's anything that should prevent those existing institutions, the prestige players like the New Yorker or the Atlantic or whatever, from participating in this new economy and for building for it too. And so if I were the New Yorker, I wouldn't be investing all my resources and just growing the New Yorker magazine bigger and bigger and bigger. But I'd be looking for opportunities to foster new voices and build a new generation of editorial products. in the Substack ecosystem or in some other ecosystem that resembles Substack that has a similar sort of rules and a similar sort of ecosystem, similar like community of people who care about culture. So it's like a little bit gloomy for the people who are still trying to run off the fumes of a business model invented in 1925. But it's very bright for those who are willing to embrace the business model of 2025. Amazing. Well, we like to end. Each episode with some lighter but also philosophical questions. So maybe we'll jump into those. The first one is one of my favorite, and I try and ask as many people as I meet this question because it's just a secret way for me to build a great reading list. Chris, maybe you can start us off. If you had the power to assign a book to everyone on Earth to read and understand, what book would you pick? And you can't say Hamish's insane mode book. Please, please. Just forget that one exists. Maybe I don't agree with the premise of the question. I would pass. I would just say like, hey, I don't think forcing everybody to read and understand something. Interesting. I'm like, yeah. What would be bad about that? Yeah, I guess like forcing people to read and care about something that... just I think is important feels immoral to me. I'm like, it should be, you know, I'd want people to read the thing that they read that they want that matters to them. And I don't, I don't, I don't, I'm not so confident in my own worldview or my own taste or my own model of the world to think that it should be forced on everybody.

That's a very interesting answer in its own right. So I think you're the first dissenter I've come across. Hamish. Nothing if not disagreeable. Would you venture to prescribe a book to us all? I'd massively embrace this opportunity to force the culture that I prefer on the masses. It's not forcing a gunpoint, I want to clarify. No one's being harmed in this thought experiment. I was envisioning everyone strapped down on a gurney with a book forced in front of their eyes and the words just get pushed into the brain. Yes, exactly. You know, I might actually say The Candid Retails. I've only read some of them. It's a huge work and it's hard to fight through the prose of Chaucer. You're assigning one that you haven't even read, to be clear. I read a good deal. You have not read and understood this, but you're already ready to force it on everybody. I just require everyone to read and understand it at the level I understand it at, which is a rudimentary, basic level, because the storytelling is amazing, and the language is beautiful, and it's an exceptional mix of the profound and the profane. It's a total high-low kind of culture book with important messages about humanity, such like not everything is as it appears, and the ones who present themselves as the most virtuous are sometimes the ones who have the most corrosion of the soul. So Canary Tales, get into it, good one. Maybe you can get ChatGPT to give you a tidy summary. in modern vernacular. Okay, but that's my pick. Perfect. I'll see if Chris will join us on this one. He's going to poo-poo all of these questions. If that was his pose on the first what book do you think people are going to read? What's it going to do with the rest of these? Yeah, it's hard for me to imagine. I look forward to seeing it. Maybe you will wriggle out of it.

What's a practice that we should borrow from another culture or era? Okay. I'm from New Zealand. My mom was a Maori teacher. Maori are the indigenous people of New Zealand. This is one I default to a lot. Whenever they get up to talk publicly in front of the group, they acknowledge their ancestors. There's another kind of saying, I guess, called matawaka, referring to sitting in the canoe and in the Maori canoes, which they migrated from far-flung lands from to New Zealand in. They paddle with, they rode with their backs to where they're going. And so they're looking at where they came from. And I think this is like a very useful concept and honoring of what you're building on and what you're contributing to. and moves you out of this particular moment that you exist in. So Matawaka and like acknowledging your ancestors and whenever you get up to speak in public, I think you're like very good grounding practices that remove some of the ego of your current life and help you build on something that is greater than yourself and greater even than the current moment you're in. I love that. Beat that, Chris. Yeah, let's see. I think we should... Pillage like the Vikings. Pillage like the Vikings. No, I mean, well, I think we should create new rituals. I think that, you know, the idea of having ritual, of having sort of like things that are kind of sacred or done repeatedly is a powerful sort of human technology. And I'm not, I wouldn't advocate for, you know, adopt old religions in order to get those things. But I think the fact that we're missing those things is a bug. And I think we should be inventing new versions of the old forms. He means Scientology, by the way. Yeah, exactly. Final question. What will the historians 100 years from now say about our current era? How long is the current era in this?

You could define it however you like, I suppose. You could say the current era we're in is maybe 10 years long, or maybe you say, actually, this era stretches back 50 years because it's all part of the same movement. I leave that to your hypothetical historian. If we could go with the 10 to 20-year time frame, I would say this is going to be looked at as the chaos era. This is a moment of transition between some major shifts. with some major periods in technology and culture and the media that is creating a ton of volatility, a ton of power redistribution and chaos that is ultimately going to lead to a new kind of order and something better, but in the moment feels messy as hell. How does that strike you, Chris? Good answer. That's why I went first, so you wouldn't say that first. I do think, I think this will be the AI transition. Maybe a way to put this is there are little decisions and little quirks of fate and butterflies flapping their wings happening right now. And it's hard to predict which ones these are, but I think this, the moment where this technology is coming about, where we're figuring out how to build it, where we're figuring out how to build a culture around it there's it's a moment of extreme leverage and so i think people will look back and in order to explain a lot of how their world is a hundred years from now they'll be able to go back and like look at you know a blog post that you wrote mario that said something that had some ripple that caused some ai researcher to think about something or i think we're i think we're getting to like lay the foundations for uh a new era of sort of technological civilization, which is exciting. That's a perfect note to end on. I knew I would enjoy this conversation, but I think I enjoyed it even more than I might have imagined. So thank you both for being here and for chatting with me. Thank you. Thank you very much. That's it. Thank you for listening to this episode of The Generalist Podcast. Please subscribe on Apple Podcasts, Spotify, or your preferred podcast app.

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