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

In a world where attention is fragmented and algorithms rule the content landscape, Chris Best and Hamish McKenzie are taking a radically different approach with Substack. Rather than chasing clicks, Substack focuses on a simple yet powerful idea: creators should own their work and make money directly from their audience through paid subscriptions. With over 5 million paid subscriptions and tens of millions of active readers, Substack has turned this model into a transformative force in media. In this episode, Chris and Hamish unpack how they’re reshaping creator economics, navigating AI’s role in creativity, and enabling a new era for writers, from serialized fiction to short-form video. Their bet? That if content adds real value—whether it educates, entertains, or helps people earn—audiences will pay for it. In our conversation, we explore: • How Substack grew from a simple newsletter tool to a multi-format media platform with 5 million+ paid subscriptions • Why the "soul connection" between creators and audiences is becoming more valuable in an AI-dominated world • The inside story of Substack's clash with Elon Musk and how it ultimately strengthened their platform • Why the ceiling for great writing and culture might be much higher than we're currently imagining • How Substack's subscription model creates dramatically better economics for creators than ad-supported platforms • Chris's "grand unified theory" for how AI will influence content creation and consumption • Why their short-form content isn't just a "sticky trick" but a pathway to deeper engagement and discovery • The future of traditional prestige media brands • Much more — Thank you to the partners who make this possible Vanta https://www.vanta.com/mario: Automate compliance and simplify security. Brex https://www.brex.com/mario: The banking solution for startups. WorkOS https://workos.com/: The modern identity platform for B2B SaaS. — For a full transcript of the episode, please visit: https://thegeneralist.substack.com/p/the-substack-playbook — Timestamps (00:00) Intro (05:27) An overview of Substack and its current scale (06:53) The origin story of Substack (19:20) Finding the first believers (24:17) Successful fiction on Substack, and why there’s potential for much more (29:09) The different mediums available on Substack (32:27) How Substack’s feed differs from social media (37:33) The clash with Elon Musk and Twitter/X (47:23) How Substack’s network helps creators succeed (52:07) TikTok creators moving to Substack after the ban (56:20) The future of paid media consumption (58:24) Chris's grand unified theory of AI and media (1:07:07) Substack’s AI tools (1:10:54) Why it’s hard to predict where AI is taking us next (1:13:42) Advice for traditional media institutions (1:16:48) Final meditations — Follow Chris Best X: https://x.com/cjgbest LinkedIn:https://www.linkedin.com/in/cjgbest/ — Follow Hamish McKenzie X: https://x.com/hamishmckenzie LinkedIn: https://www.linkedin.com/in/hamishmckenzie/ — Resources and episode mentions —Books— • The Anxious Generation: How the Great Rewiring of Childhood Is Causing an Epidemic of Mental Illness: https://www.amazon.com/Anxious-Generation-Rewiring-Childhood-Epidemic/dp/0593655036 • The Canterbury Tales: https://www.amazon.com/Canterbury-Tales-Geoffrey-Chaucer/dp/0140424385 —People— • Jairaj Sethi on LinkedIn: https://www.linkedin.com/in/jairaj-sethi/ • Andrew Chen on LinkedIn: https://www.linkedin.com/in/andrewchen/ • Mike Kerns on LinkedIn: https://www.linkedin.com/in/mike-kerns-63219/ • Patrick Collison on LinkedIn: https://www.linkedin.com/in/patrickcollison/ —Other resources— • Substack: https://substack.com/ • Kik: https://kik.com/ • Listicle: https://en.wikipedia.org/wiki/Listicle • The dress: https://en.wikipedia.org/wiki/The_dress • Craigslist: https://www.craigslist.org/ ... Resources continued at: https://thegeneralist.substack.com/p/the-substack-playbook — Production and marketing by penname.co https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

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

• 0:00Speaker 00

  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 and technology going to do to media?

• 0:16Mario Gabriele?

  It says 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.

• 0:31Speaker 02

  If we could go with the 10 to 20 year timeframe, 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, it feels messy as hell.

• 0:58Mario Gabriele?

  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

• 1:39Mario Gabriele?

  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 Substack's 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.

• 2:21Mario Gabriele?

  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 Mackenzie. 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.

• 3:04Mario Gabriele?

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• 3:49Mario Gabriele?

  and prove security in real time. My listeners can get $1,000 off Vanta at vanta.com/mario. That's V-A-N-T-A dot com slash Mario for $1,000 off.

• 4:05Mario Gabriele?

  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

• 4:50Mario Gabriele?

  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 US venture-backed startups, trust Brex to help make every dollar count toward their mission. Join them at brex.com/mario. Chris, Hamish, it is fantastic to have you on here today. Thank you so much for being here.

• 5:33Mario Gabriele?

  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.

• 6:00Speaker 00

  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, you know, 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 five million paid subscriptions.

• 6:44Mario Gabriele?

  Oh, wow.

• 6:45Speaker 00

  Amazing. And, you know, tens of millions of, tens of millions of people actively subscribing to Substacks.

• 6:53Mario Gabriele?

  Amazing. Well, we're, 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, you know, why this was a mission that, that spoke to you. And I know that, you know, Chris, you were sort of the, the person who looped it in with Hamish, so I'll, I'll let either one of you jump in there. But, um, yeah, I'd love to, to hear a little bit about that.

• 7:18Speaker 00

  Well, I'd done another company before this. It was a messaging app called Kick Messenger. Uh, I met Hamish and Jay, who's our other co-founder there. Uh, 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. Uh, not to, you know, put too much shine on you, Maria, 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

• 8:03Speaker 00

  stuff is important, right? It changes how people think. It changes how they understand the world. And yet, a lot of the current internet, you know, this is in 2017, didn't feel that heroic. Uh, the state of the legacy media was kind of, you know, 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, for, for them and for advertisers.

• 8:30Mario Gabriele?

  Yeah.

• 8:30Speaker 00

  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 programmers 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,

• 9:12Speaker 00

  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 Substack, 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

• 9:53Speaker 00

  media on the internet and make a thing for culture and like, put people back in charge of their media diets and da, da, da, da, da. 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, this grand thing.

• 10:28Mario Gabriele?

  Now, Hamish, Chris mentioned that you had worked as a writer, you were a writer, you were a journalist for many years, who'd written books of your own. When you look back at the media landscape that Chris was writing his screed about in 2017, if you had to trace back the 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? The creator of the very first listicle, where do we start?

• 11:01Speaker 02

  Yeah, it all ended with the black and gold dress. No, the...

• 11:06Mario Gabriele?

  Exactly.

• 11:08Speaker 02

  Well, I think these problems are not to do with any one actor or 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, they took out the classified business that newspapers relied on so heavily. And then Google and Facebook came along, 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.

• 11:49Speaker 02

  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 now hell-bent on destroying the media and building something in his image. And then later on, actually, the streaming services have come along, they're making it even harder for the existing television businesses, the TV news business, cable news, etc. So these old business models that were designed in the 20th century, maybe even the 19th century, have been 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.

• 12:34Speaker 02

  And so... By the time 2017 rolled around, the physical illness that traditional media had 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

• 13:15Speaker 02

  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 came along, things are looking

• 14:00Speaker 02

  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 like potential customer base to hold up the next era of giant technology companies.

• 14:15Mario Gabriele?

  Yeah, that didn't, I imagine, feel like an obvious bet for, for anyone, but I really love what, what you guys are saying around that it felt like such a big idea in some ways. You're playing with, you know, 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, you know, run subscriptions and to sort of like, yeah, what the conversations were like with those first VCs.

• 14:56Speaker 00

  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.

• 15:21Mario Gabriele?

  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 spear. And it's not like they're huge businesses, right?

• 15:34Speaker 00

  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 1,000 people, et cetera. Because if you start with something that's kind of like pretty good for a million people, it goes nowhere.

• 16:18Speaker 00

  And it's not just like, we didn't just sort of like take this on faith. We were thinking about, we were 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.

• 17:00Speaker 00

  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.

• 17:09Mario Gabriele?

  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 that really resonated with that?

• 17:21Speaker 02

  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.

• 17:37Speaker 00

  Didn't know what a Substack was yet.

• 17:39Mario Gabriele?

  Yeah, exactly.

• 17:40Speaker 02

  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 like 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. And once we had that story nailed, then it's a story we could tell investors. And some, yeah, some immediately got it and saw the potential. And some were like, who's going to pay for newsletters?

• 18:24Speaker 02

  How many Ben Thompsons are there in the world? And I think, you know, 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 Kerns at Churnin Group was one of the early believers. And Andrew Chandler came in early.

• 18:39Speaker 00

  Emmett Shear.

• 18:40Speaker 02

  Early believer later on.

• 18:43Speaker 02

  And that's, that's all we needed. And yeah, I think it feels like a small thing. Start a paid newsletter, you know, 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, 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 like not just sort of begrudgingly pay for that, but they'll be happy to pay for it. They'll be in like in this game with you. And once that becomes possible and proven, then all sorts of things are newly possible.

• 19:21Mario Gabriele?

  There's a version of Substack I could totally imagine that is like a really much smaller but sort of thriving indie business, you know, sort of like the widgets to tip a creator or buy a cup of coffee or, you know, whatever those things are.

• 19:36Speaker 02

  We totally should have done that.

• 19:38Mario Gabriele?

  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?

• 19:55Speaker 00

  You know, I'd had, I'd had sort of the 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 on to something potentially quite big and transformative was the thing that made me want to work on it in the first place. You know, if we, 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 worthwhile thing for somebody.

• 20:37Speaker 00

  But it wasn't, that wasn't the, that wasn't what made me, you know, pour my, pour my life into this thing.

• 20:44Speaker 02

  For me, there's kind of like a moral impulse as well. Like, 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

• 21:25Speaker 02

  can have a really meaningful effect on the media ecosystem, which in 2017, and today still really, is in a like pretty dire state.

• 21:33Speaker 00

  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.

• 21:40Speaker 02

  So it was like you should go as big as possible. And maybe someone comes along and crushes you and does it better or like takes it takes over along the way. But otherwise, there wasn't like 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.

• 22:10Speaker 00

  I hate when people call it content.

• 22:12Mario Gabriele?

  I was gonna say, even the word content feels so unpromising, right? It feels so calorieless.

• 22:18Speaker 00

  It begs the question, it's just, what is it? Oh, it's the thing that's contained. What are you talking about?

• 22:22Mario Gabriele?

  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.

• 22:33Speaker 02

  Yes. Yeah, it's much better.

• 22:35Mario Gabriele?

  That's very good. I love this, the way you said this, Hamish, of 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 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 were the like, you know, maybe the empty lots where you're think you have an eye on them and say, actually, we could really, we could really see something amazing

• 23:20Mario Gabriele?

  happening here?

• 23:21Speaker 00

  I mean, I'll tell you, early on, there was a real question that, you know, investors and even we had was, is this gonna 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 that stuff is still doing very well on Substack 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.

• 24:06Speaker 00

  And for everything that there's somebody out there that's really into, there's usually like something. And it'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, is just fiction in general. I think fiction's really important. I think the idea of serialized fiction is well, well-developed and could work well. And I think the overall, the, yeah, the overall preponderance of fiction on Substack. I think if we could crack the code on it, could, could be higher.

• 24:47Mario Gabriele?

  I, I, you might've seen my eyes sort of light up when you said that. One, because I know you're the, the son of an English teacher. And so, you know, that's, you know, you're, you're, you're 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

• 25:27Speaker 00

  She's since crowdfunded a book successfully on her Substack.

• 25:29Mario Gabriele?

  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, to cultivate that further, it looks like? Maybe, Hamish, you can tell us a little bit about that.

• 25:46Speaker 02

  Gonna make us, uh, write some checks here that we can't promise on cashing in the immediate future.

• 25:53Speaker 02

  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 will like write their draft in public. A lot of Jonathan Haidt's The Anxious Generation was first published on Substack for his Substack after Bebel. 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

• 26:34Speaker 02

  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 like 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

• 27:19Speaker 02

  keep evolving the product to perfectly suit those needs, won't we, Chris?

• 27:23Mario Gabriele?

  I'm not trying to pin you down to anything in particular, but you know, you mentioned how it's worked for different books and I've seen some really interesting projects over, you know, the past few weeks in particular, when I've been learning about this a bit more. For fiction in particular, do you think there's sort of certain things that are required? You know, you mentioned writing in conversation with your audience. I always think of Andy Weir in The Martian where he sort of, you know, wrote bit by bit on his blog and then, you know, that has since become a massive hit. Yeah, wondering if that type of storytelling in particular requires different tools?

• 28:01Speaker 00

  I do think there's some practical stuff that we could improve. You know, 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 get something to get anything in my inbox, the new one's at the top. And like 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 got the second chapter, read the second chapter, I'll get the third chapter and I'll like 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 gotta go find the third chapter or like, where am I in this thing?

• 28:42Speaker 00

  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.

• 29:10Mario Gabriele?

  Yeah, I really believe there, you know, will or can at the very least be a future in, in just the same way that you have Netflix and Amazon that wins Oscars, you know, maybe there will be a National Book Award winner that was first published on Substack.

• 29:26Speaker 00

  Sure. And you could publish, I mean, you could publish a TV show on Substack too now with the same token, right? And you would want it to be work the same way. You want it, you know, if I go to the Netflix show, it 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.

• 29:48Mario Gabriele?

  That's really true. You, 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 like 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?

• 30:23Speaker 00

  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 Instagram was pictures and then Snapchat was disappearing pictures and then Tik Tok 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?

• 30:56Speaker 00

  It's hard to make an app that has all of these different short form, social media-ish posts and long form articles and podcasts and videos, short form videos and like maybe others like chat. There's all these things. 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, we've got, the thing we've kind of done is we've like 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? Like, there's so many different things. So I think we have still some work to do to kind of like bring it together into a simple package.

• 31:36Speaker 00

  But listen, our thing ultimately is like, 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 know, you can, 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

• 32:18Speaker 00

  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.

• 32:28Mario Gabriele?

  I certainly want to talk more about AI at some point. But, 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, you know, short social media, short videos. Is there, do you ever like have a worry as, as a, 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, you know, want to consume this, that actually, you know, short video ends up taking time away from people reading the, you know, great piece of fiction or, you know, George

• 33:09Mario Gabriele?

  Saunders Story Club, whichever of these great pieces of culture that are, that are on Substack, you know, it, you know, sort of shifting that, that focus a bit.

• 33:19Speaker 02

  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 news feed, 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

• 34:03Speaker 02

  time, my relax 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.

• 34:22Speaker 02

  Wouldn't it be interesting to see what happens if you rip the ads out of them? And 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 where 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.

• 35:05Speaker 02

  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.

• 35:28Mario Gabriele?

  Anecdotally, I will say that you phrase that perfectly. When I use notes, for example, which is, you know, the sort of Twitter equivalent on Substack, I don't feel dirty.

• 35:38Speaker 02

  Good.

• 35:39Mario Gabriele?

  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-

• 35:48Speaker 00

  Elon's not on there yet.

• 35:49Mario Gabriele?

  He's not on there yet?

• 35:51Speaker 00

  I will say-

• 35:51Mario Gabriele?

  He's probably somewhere on there.

• 35:52Speaker 02

  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 is, the ads warp the incentives. The ads change. The advertising being the business model that makes those whole companies run.

• 36:13Speaker 02

  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 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.

• 36:59Speaker 02

  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. The other feeds end up polluting your mind and the Substack feed maybe can even cleanse your mind.

• 37:20Mario Gabriele?

  Can even cleanse your mind. That's a new tagline.

• 37:23Speaker 00

  Cleanse your mind.

• 37:24Mario Gabriele?

  Yeah. Might be an overpromise.

• 37:27Speaker 02

  But you don't come away feeling so polluted. Let's leave it at that.

• 37:31Mario Gabriele?

  Yes, absolutely. And, you know, I think it's interesting. It's 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.

• 38:12Mario Gabriele?

  It also, I think, brings up the the conversation, the the Internet of Beef's, you know, battle royale between Substack and X. I, you know, for those who maybe didn't follow that chapter closely, can you explain sort of why there is some degree of of intense competition there? And how sort of creators maybe got caught in the crossfire a little bit?

• 38:36Speaker 02

  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 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,

• 39:19Speaker 02

  where there's not like an ad-based feed that has sometimes competing interests with the deep relationships feed or the deep relationships platform. And so we're like, hmm, 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 night before we, well, 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 like build that ecosystem up. But it didn't matter to Elon.

• 40:00Speaker 02

  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 newsletter. He accused of stealing data in the meantime, and 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 he's 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.

• 40:44Speaker 00

  Way to take the temperature down by using a neutral metaphor.

• 40:46Speaker 02

  Yeah, yeah. Sorry to all the Russia fans. But 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 as we've, 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 creators' interests at heart. They're mostly focused on their own platforms and the advertising. So that is, that's basically what happened. I think Elon's interest has like moved on to other things at the moment. And so like maybe that.

• 41:30Mario Gabriele?

  He's got a few things that he's on his plate.

• 41:32Speaker 02

  Their beef has become like a small medallion on the corner of his vast plate.

• 41:37Mario Gabriele?

  Yes, his very vast plate. When you, you know, 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, you know, maybe there is a way to do that in a deep partnership or even an acquisition? Like, did it ever get to those, to that sort of level of conversation?

• 41:56Speaker 00

  It's not something that we were keyed 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, it would break the thing that we're trying to accomplish.

• 42:20Mario Gabriele?

  Yeah. Like philosophically, these are such different businesses, right?

• 42:24Speaker 00

  Yeah. And it's not, I think it would just, it would be hard to make, make the thing that we're trying to make in a, in a context like that. And we're seeing, I mean, we are seeing this now, like we, we've been working on the Substack app and this sort of like this network concept for years and years and years because we knew it was, 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, it was, it was no, no fun. But from a systematic level, it was basically a rounding error by that point.

• 43:05Speaker 00

  Like it didn't matter. But there was a time like in 2019 where that actually was true, like basically everything on Substack was downstream of, you 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

• 43:48Speaker 00

  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, they blocked us, but then since then they've, it's basically all links are deprioritized. I don't think Substack 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,

• 44:31Speaker 00

  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 Substack 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, you know, keep up with the things they're subscribed to and love and then find new things to fall in love with. And you, you're talking before about, I'll, I'll, I'll add one more thing to this before I completely filibuster.

• 45:14Speaker 00

  But, uh, you're mentioning like the, is there tension between short form and long form in that?

• 45:19Speaker 02

  Like, yes.

• 45:19Speaker 00

  By adding the notes feed, does that, you know, is, 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. Uh, 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, would use Substack.

• 46:04Speaker 00

  It'd be harder to make money as somebody working on Substack. And so as we've been building the, the, you know, the discovery feed, the thing we've seen again and again is there's, when you, 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 retain better and came back more often. But also they paid more money. Like there's sort of like a, 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.

• 46:47Speaker 00

  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.

• 47:09Speaker 02

  We're such magicians that we can trick you into being a decent person.

• 47:14Mario Gabriele?

  We will trick you into reading quality writing, please.

• 47:18Speaker 00

  Decent persons too isn't overclam. We can trick you into reading and watching and listening to good stuff.

• 47:23Mario Gabriele?

  The.

• 47:23Speaker 00

  That's good enough for us.

• 47:24Mario Gabriele?

  I remember when we were chatting back in 2023, when we wrote 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.

• 47:55Speaker 02

  A great example of one such platform exists, and it's probably the best one for media on the internet at the moment, which is other than Substack, which is YouTube. Not only a giant business, but a place like quality stuff, the historic and contemporary with that where people are bound in these relationships. The 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, was 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.

• 48:38Speaker 02

  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.

• 48:53Mario Gabriele?

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• 49:11Mario Gabriele?

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• 49:56Mario Gabriele?

  like a really large audience, like 250K subscribers, producing fantastic videos and absolutely could not make the economics work, was effectively losing money on every video for a couple of years. And having that direct relationship with a subscriber totally changes that.

• 50:19Speaker 02

  That's right. There'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-ish thousand 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

• 51:01Speaker 02

  Substack, 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 here 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. Like, I don't mean, well, yes, it can increase fast, but like, the time from starting to get to sustainability with a subscription model, that depends only on...

• 51:38Speaker 02

  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 in some third party comes in and monetizes it and gives you some scraps from the table.

• 52:08Mario Gabriele?

  Chris, you were mentioning a moment ago, you know, 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 US 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?

• 52:36Speaker 00

  Yeah, you know, one of the things that we that Substack offers, as you know, is ownership over your audience, right? So you have, 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, you know, these are your relationships. You can take it to another platform, you can, you know, 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, if, part of the reason you can trust Substack is because if we start to like turn evil, you have this, you have this right

• 53:17Speaker 00

  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 TikTok 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 TikTokers and said, hey, you should start a Substack.

• 53:59Speaker 00

  And, you know, at least you should collect an email list so that you have this list. But also we've suddenly, 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 like a very famous, you know, political reporter, TikToker, like news, news TikToker.

• 54:29Speaker 02

  He's sort of like a TikTok news personality. Yeah. He would like tell the, translate the political news every day for his audience.

• 54:35Mario Gabriele?

  None of the three of us are, are huge TikTok natives, it feels like. I mean, there's probably some sharp lingo there.

• 54:41Speaker 00

  During this period, I also created my TikTok account and started making TikToks.

• 54:44Speaker 02

  Oh, God.

• 54:44Speaker 00

  I went viral once. It was thrilling.

• 54:47Mario Gabriele?

  You did? What did you post?

• 54:48Speaker 00

  Well, not, not, not very, but I just, I don't know.

• 54:50Speaker 02

  It was a sexy dance.

• 54:52Speaker 00

  Here's why you should start a Substack.

• 54:56Speaker 00

  But yeah, and he's, he's got, he's got a Substack 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 like 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, like what kind of work he can do and what kind of ambition he can have with it.

• 55:41Speaker 00

  And I, 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, there are, and they're disproportionately ill-served, right? The people who have, uh, maybe not like a, the, the most enormous audience, but whose audience like deeply values what they're doing, those people could not just.

• 56:13Speaker 00

  You know, have the benefit of having an email list and all that stuff. They can make more money on Substack. And so we're, uh, we're working on bringing the, bringing the word to them.

• 56:21Mario Gabriele?

  Well, I, I'm sure you will. When you sort of project forward five, 10 years, you know, imagine that we, we do have so many folks from, from TikTok aboard, you have, you know, great food folks, just, you know, several orders of magnitude bigger than it is today, let's say. What does the sort of consumer behavior look like? 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? Is it that, you know, people do start to bundle and, and that becomes an important part of it? How, how do you think that plays out?

• 56:57Speaker 00

  People are already willing to spend money on culture that they value. And it's not because they're, it's not, they're, 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 costs 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, a more like, a more valuable return on your time and your, 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

• 57:37Speaker 00

  is a resounding yes, but who have not yet had the opportunity to, to do that. And so I think first, like the, the highest order part of this is like, you know, are we as a society investing like 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, and they're not going to grasp it. They're going to feel like this is great. I'm like able to get all of the stuff that I, that I really care about. I think there's some limit. I think there's ways that we can like, you know, work on. Making it like, making the economics of it kind of like maximally favorable to people

• 58:19Speaker 00

  on both sides, but I think the the highest order bid is just like, it's worth paying for things that are good.

• 58:24Mario Gabriele?

  Yeah, I I'm interested, I wonder where that share of wallet ends up coming from, even if we say, okay, you know, I obviously can't scale limitlessly that people will just spend all their money on 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 substack, you know, several substacks that I subscribe to once a month. Do you, Hamish, do you have any thoughts on on where that share comes from or how you think that plays out?

• 59:07Speaker 02

  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.

• 59:15Mario Gabriele?

  I would love to.

• 59:16Speaker 02

  As well. I think that's probably, 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 shifted from cable a little bit. No one, no one used to pay for, oh, I guess I was about to say Spotify, but I guess that shifted from like buying records individually a little bit, but it probably contributed to increased spend in other ways, like on shows, on merch, et cetera. But I think the AI revolution take is a pretty interesting one, maybe.

• 59:46Mario Gabriele?

  It's a good time for a grand theory.

• 59:48Speaker 02

  Yeah, let's give a grand theory, Chris.

• 59:50Speaker 00

  Well, okay, here's a 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, 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.

• 1:00:34Speaker 00

  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 the, 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, there are other things that, that get more expensive. Basically, the, the pieces that are not getting, whatever pieces are not getting automated. There's a thing called Baumles 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,

• 1:01:17Speaker 00

  the things that are not touched by technology just get more expensive and take up a bigger and bigger share of the economy. And 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.

• 1:02:00Speaker 00

  And if you, if your view of the purpose of media is to be kind of like a drug, where it's, it, it just, it's, it's effect on you is the only thing that you care about. The, 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 TikTok that's a hundred times more powerful than human TikTok 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. On just 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.

• 1:02:45Speaker 00

  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, 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, more things to read than I could ever

• 1:03:27Speaker 00

  read, more video to watch than I could ever watch. And in that, and that's just going to get even more extreme. And it's the, 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

• 1:04:11Speaker 00

  this Baumol 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, the, you know, what's the right amount for people to spend on Substack? I think it's much higher. I think it's an exciting, an exciting future.

• 1:04:41Mario Gabriele?

  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 and, 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?

• 1:05:06Speaker 00

  Yeah, basically. And we're, you know, we're gonna need new cultural norms to deal with all this stuff. But yeah, the, the, the trust relationships that I have become more valuable.

• 1:05:16Mario Gabriele?

  Hamish, when you first heard the grand unified theory, what was your, what was your spot or your response? How, how much do you buy into that worldview?

• 1:05:24Speaker 02

  I buy into it a lot. I, it pumps me up. I think I've always thought that writers are more important than developers, which is something I said.

• 1:05:31Mario Gabriele?

  Oh, we always, yeah, I agree, of course.

• 1:05:33Speaker 00

  He tells me that every day.

• 1:05:35Mario Gabriele?

  Well, yeah, I think, gosh, this is like the only company where you have to listen to that and, and take it.

• 1:05:40Speaker 02

  Yes. Yes. The writers are the kings here.

• 1:05:43Speaker 00

  Have to. Maybe he's too strong.

• 1:05:45Speaker 02

  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 cultures, not just writing, video, audio, etc. But I also think that's like, 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, to like to get even like more grandiose and airy fairy about it.

• 1:06:25Speaker 02

  The, the thing that gets valued in this new economy is less the 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, that when that human thrives, I thrive too. And then, 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 hopeful.

• 1:06:58Mario Gabriele?

  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.

• 1:07:08Mario Gabriele?

  On just one more point on the AI front before 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?

• 1:07:26Speaker 00

  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, one of there was a bunch of things that were good about Substack, like the business model is good, you make this money. But one that I think is maybe under is not 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.

• 1:08:11Speaker 00

  But there's a lot more people who are just 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 like 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 sort of like, that's at least the like animating spirit of where we're trying to get to. And I think something that's happening, not in the in the distant future, but is currently today, very possible is you can do that for all for many more kinds of media. So we have an example of this.

• 1:08:56Speaker 00

  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.

• 1:09:07Speaker 00

  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, 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, they didn't have the perfect microphone. Okay, AI fix 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, go and just like edit it, cut out the boring parts, find the clips that are really good. And so there's this 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

• 1:09:51Speaker 00

  and talk into 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 is a, 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. Didn't have a whole.

• 1:10:18Speaker 02

  And got an instant media business out of it. Every like people showed up in shows, they were like excited to pay to subscribe to support him and get what he was purveying, which is, he hasn't paid all the any content. So no one's getting content that they're paying for, but they pay for that soul connection. And talks to his hand, talks to his hand, has an instant media business in this, in the space of seconds.

• 1:10:40Speaker 00

  Cause the face don't give a damn. Sorry, that's the nineties kid in me. Nevermind.

• 1:10:44Speaker 02

  Please keep that, don't cut that.

• 1:10:45Speaker 00

  Cut that part out.

• 1:10:45Speaker 02

  Don't cut that, it's genius.

• 1:10:48Mario Gabriele?

  That'll be the, that'll be the clip we lead with.

• 1:10:54Mario Gabriele?

  How far do you think you might go? Or do you see the possibilities of going around like new mediums? For example, like, you know, there's could be a version of this where the, the writer brain in me is like, well, there could be really cool text adventure games that, you know, artists might want to create. Like what are the constraints that are important to keep before, you know, things get too unwieldy? Maybe?

• 1:11:19Speaker 00

  I think it's really hard to predict. You know, 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 like, you know, 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 like, unlike anything we've ever able to do before, but kind of like, you know, I don't know how to explain it to my mom.

• 1:12:01Speaker 00

  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. 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, 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

• 1:12:44Speaker 00

  in a way that they can actually wrap their hands around it 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.

• 1:13:04Mario Gabriele?

  Yeah, there's still several layers of friction.

• 1:13:06Speaker 02

  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 like expressions of culture and content are possible as long as that thing is stable and constant.

• 1:13:43Mario Gabriele?

  Hamish, as a old media person who became

• 1:13:46Speaker 02

  Not at all.

• 1:13:46Mario Gabriele?

  A new media person in my 40s.

• 1:13:48Speaker 02

  I knew, I was waiting for it. I knew it was coming.

• 1:13:52Mario Gabriele?

  That became, you know, a new media person and at the vanguard of this, this movement. I'm curious how you think about the positioning of these prestige brands of, of the past and present. Like if, you know, if you were to be airdropped into, insert prestige media brand here, you know, The Atlantic, The Economist, The New Yorker, like what would be the things that you would do in your, you know, 100 day sprint to try and prepare these publications for, you know, the next couple of decades?

• 1:14:23Speaker 02

  I think some of the core, something that's core to their identity doesn't have to change, which is to like maintain these high quality standards and journalistic ethics and retain this sort of prestige aura. But except at the same time, that their general reach is gonna probably shrink. They're not gonna 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 some, and many of them will

• 1:15:07Speaker 02

  probably disappear over time just because they have this business model sickness that is gonna be impossible to recover from. The world is different in 2025 than it was in 1925 and a lot of these things were born. But there is also ample opportunity to rebuild, to build institutions of the next era, things like the generalist, or the anklar, or the bulwark, 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

• 1:15:49Speaker 02

  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 ecosystems, similar like community of people who care about culture.

• 1:16:33Speaker 02

  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.

• 1:16:49Mario Gabriele?

  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 is insane, but look.

• 1:17:19Speaker 02

  Please, just forget that one exists.

• 1:17:24Speaker 00

  Maybe I don't, I don't agree with the premise of the question. I wouldn't, I would pass. I would just say like, hey, I don't think forcing everybody to read and understand something.

• 1:17:33Mario Gabriele?

  Hmm, interesting.

• 1:17:35Speaker 00

  I'm like, I'm like, yeah.

• 1:17:37Mario Gabriele?

  What would be bad about that?

• 1:17:40Speaker 00

  Yeah, I guess like forcing, 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.

• 1:18:12Mario Gabriele?

  That's a very interesting answer in its own right. So I think you're the first dissenter I've, I've come across. Um, Hamish.

• 1:18:19Speaker 00

  I'm nothing if not disagreeable.

• 1:18:22Mario Gabriele?

  Do you, would you venture to, to prescribe a book to us all?

• 1:18:26Speaker 02

  I'd massively embrace this opportunity to force the culture that I prefer on the masses.

• 1:18:32Mario Gabriele?

  It's not forcing a gunpoint, I want to clarify. No one's, no one's, you know, being harmed in this, in this thought experiment.

• 1:18:38Speaker 02

  I was, 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.

• 1:18:48Mario Gabriele?

  Yes, exactly.

• 1:18:49Speaker 02

  You know, I just, I might actually say the Candor retails. I've only read some of them. It's a huge work and it's hard to like fight through the prose of Chaucer.

• 1:19:00Speaker 00

  You're assigning one that you haven't even read, to be clear.

• 1:19:02Speaker 02

  I read, I read a good deal.

• 1:19:03Speaker 00

  You have not read and understood this, but you're already ready to force it on everybody on earth.

• 1:19:07Speaker 02

  I just read, I just forced, okay, I just require everyone to read and understand it at the level I understand it at, which is a rudimentary, basic level. Because these stories, the storytelling is amazing and the language is beautiful and it's a.

• 1:19:23Speaker 02

  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, um, not everything is as it appears. And the ones who present themselves as the most virtuous are sometimes the ones who, uh, have the most corrosion of the soul. So can retails, get into it, good one. Maybe you can get chat G P B G P T to like, give you a tidy summary in, in, in modern, uh, vernacular. Okay, but that's, that's my, that's my pick.

• 1:19:58Mario Gabriele?

  Perfect. Um, I'll see if, if Chris will, uh, will join us on this one.

• 1:20:04Speaker 02

  He's gonna, he's gonna poo poo all of these questions. If that was his pose on the first, what book do you think people are gonna read? What's he gonna do with the rest of these?

• 1:20:13Mario Gabriele?

  Um, yeah, it's, it's, it's hard for me to imagine. I, I, I look forward to seeing, uh, maybe you will wriggle out of it. What's a practice that we should borrow from another culture or era?

• 1:20:25Speaker 02

  Okay, um, I'm from New Zealand. My mom was a Maori teacher, Maori are the indigenous people of New Zealand. This is one I like, I default to a lot. When, whenever they get up to talk publicly in front of the group, they acknowledge their ancestors. There's another, um, uh, kind of saying, I guess, uh, called Matawaka, where they, uh, referring to sitting in a canoe and in the Maori canoes, which they migrated from far-flung lands, uh, from to New Zealand in. They paddle with, they, they rode with their backs to where they're going. And so they're looking at where they came from.

• 1:21:08Speaker 02

  And I think this is a, like a very useful, uh, concept and honoring of what you're building on and what, what you're contributing to and moves you out of this, 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, uh, remove some of the ego of your, your current life and help you build on something that is greater than yourself and greater even than the current moment you're in.

• 1:21:37Mario Gabriele?

  I love that.

• 1:21:38Speaker 02

  Beat that, Chris.

• 1:21:40Mario Gabriele?

  Yeah, let's see.

• 1:21:41Speaker 00

  I think we should.

• 1:21:43Speaker 02

  Pillage like the Vikings.

• 1:21:46Speaker 00

  Pillage like the Vikings. No, I mean, I, well, I think, 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, new versions of the old, the old forms.

• 1:22:27Speaker 02

  So he means Scientology, by the way.

• 1:22:30Mario Gabriele?

  Yeah, exactly.

• 1:22:33Mario Gabriele?

  Final question. What will the historians 100 years from now say about our current era?

• 1:22:40Speaker 02

  How long is the current era in this hypothetical?

• 1:22:45Mario Gabriele?

  You can, you could define it however you like, I suppose. Whichever, you could say the current era we're in is maybe, you know, 10 years long, or maybe you say, actually, this, this era stretches back 50 years because it's all part of the same movement. I, I leave that to your hypothetical historian.

• 1:22:59Speaker 02

  If we could go with the 20 to 10 to 20 year timeframe, 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, in culture, in 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.

• 1:23:34Mario Gabriele?

  How does that strike you, Chris?

• 1:23:37Speaker 00

  Good answer.

• 1:23:39Speaker 02

  That's why I went first, so you wouldn't, you wouldn't say that first.

• 1:23:45Speaker 00

  I do think.

• 1:23:48Speaker 00

  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 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 100 years from now, they'll be able to go back and like, look at, you know, a blog post that you wrote, Mario, that's had something, that had some ripple that caused some AI researcher

• 1:24:33Speaker 00

  to think about something, or I think we're, I think we're getting to like, lay the foundations for a new era of sort of technological civilization, which is exciting.

• 1:24:46Mario Gabriele?

  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, yeah, for being here and for chatting with me.

• 1:24:58Speaker 00

  Thank you. Thank you very much.

• 1:25:02Mario Gabriele?

  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. Ratings and reviews help others discover these discussions. So if you enjoyed the conversation, I'd be grateful if you could take a moment to leave one. For all past episodes and more, visit us at thegeneralist.substack.com. See you next time as we continue to explore the future.