wavePod

Get Wave AI

Chris Best - Tetragrammaton with Rick Rubin | Wave AI Podcast Notes

Back to Tetragrammaton with Rick Rubin

Chris Best

Tetragrammaton with Rick Rubin

Wed Apr 29 2026

Summary

Tetragrammaton with Rick Rubin – Chris Best (April 29, 2026)

Episode Overview

In this episode, Rick Rubin sits down with Chris Best, co-founder and CEO of Substack, the influential newsletter and publishing platform. The conversation dives deep into the founding story of Substack, the changing media landscape, challenges around business models and free speech, and the evolution of the internet’s creator economy. With a mix of philosophical musings and practical advice, Chris Best discusses the rise of independent writing, platform controversies, Substack's future, and what it means to support a healthy culture of ideas.

Key Discussion Points & Insights

1. The Origin Story of Substack

Motivation: Chris Best describes his initial frustration with the state of online media and the lack of sustainable business models for quality content (00:23).

“Great writing and great culture in general is this deeply valuable thing. And so I was like, I should write. How hard could it be? … but the Internet…hasn't replaced, especially the economic engines that made those things go in a way that was satisfactory to me.” – Chris Best, [00:23]
Initial spark: Encouraged by his friend Hamish, Chris moved from complaining about media to envisioning solutions—specifically, how to empower creators.
The Core Idea: Substack is built on the premise that writers and creators are “the heroes,” deserving independence, the ability to make money, and creative freedom (02:23).

2. Building Substack: Vision, First Steps, and Naming

‘Science Fiction Vision’ vs. Humble Beginnings: Chris explains the importance of having a global vision while building actionable, incremental steps (03:15).
Newsletter as a Model: The rise of paid email newsletters (notably Ben Thompson’s Stratechery) inspired the Substack model—direct audience connection and economic sustainability (03:50).
Name Origins: Substack vs. Monograph; fate intervened when the Monograph domain was taken (07:47).

3. Platform Philosophy and Business Model

Direct Connection: Substack’s power lies in creators having direct relationships with audiences—email and podcasts were the only true “rectangles” on the home screen to enable this at the start (12:07).
Exit Rights: A fundamental promise was creator ownership—a writer could always take their email list and leave, engendering trust (13:24).
Revenue Model: Substack makes money only when writers do, taking a percentage of subscription revenue, aligning incentives (16:23).

“The only way we make money is by taking a percentage. And so we literally can't make money without the people on the platform succeeding.” – Chris Best, [16:23]
Learning from Users: The necessity of offering both free and paid options (even after initial ideological insistence on only paid) was quickly apparent from real user needs (16:58).

4. Media Industry Context and Creators’ Independence

Journalism Before Substack: Chris describes a “narrowing of thought” and loss of diversity in mainstream media, leading to his belief that “healthy intellectual culture” needed new structures (20:35).
Writers Fleeing Institutions: 2020’s “fever pitch” of ideological conformity led many high-profile journalists (e.g., Matt Yglesias, Bari Weiss, Paul Krugman) to seek independence on Substack (22:16-24:02).

“It was like Théoden after Wormtongue left in the Lord of the Rings. Like he de-aged 10 years and regained his vigor.” – Chris Best on Matt Yglesias, [23:21]
Bari Weiss and Institution-Building: Substack supports not only individual voices but also institution-builders like Weiss, whose Free Press sold for $150 million (24:00).

5. Substack Features, Growth, and Product Evolution

Feature Expansion: Substack quickly added web versions, free newsletters, podcasts, and apps—even enabling AI-powered read-aloud, auto-publishing to YouTube, and live audio/video events (14:58, 55:13).
Discovery & Community: The launch of the Substack app, Notes feature, and ‘bazaar’ model allow for internal discovery and community, making Substack less reliant on external social platforms (34:34–38:07).
Algorithmic Differences: Unlike attention-driven social media, Substack’s algorithms are designed to connect users with high-value content they might pay for, promoting a healthier media diet (39:31).

6. Substack, Social Media, and Platform Competition

Relationship with Twitter: Initially symbiotic, but over time, as Twitter’s algorithm penalized outbound links and Substack launched more internal features (Notes), the relationship soured, even leading to blocks and demotion of Substack content on Twitter (64:24–69:15).

“There was a week where not only could you not share a Substack link, if you just said the word substack, nobody would see your thing.” – Chris Best, [67:06]
Substack vs. Medium & Patreon: Unlike Medium’s “Netflix for writing” and Patreon’s payment-focused approach, Substack prioritizes creator-audience ownership and network-driven discovery (72:24).

7. Free Speech, Controversies, and Moderation Philosophy

First Amendment Values: Substack aspires to a broad interpretation of free speech, taking inspiration from the First Amendment (42:43-43:43).
Decentralized Moderation: Each writer owns their house—sets their own rules for their community (46:57-48:27).
Navigating Controversy: From trans issues to COVID skepticism to political disputes, Substack’s approach is to avoid editorial positions and not yield to “social media mobs” or pressure campaigns (49:06-53:42).

“If you're going to get smashed, get smashed for doing something you believe in, because that's worth it.” – Chris Best, [53:31]

8. Best Practices & Advice for Substack Creators

Start Now, Iterate: Don’t overthink—just publish, and do it frequently. Volume and momentum matter (77:24–80:31).
Promotion: Creators should share their work, leverage word-of-mouth, and let Substack’s infrastructure support discovery, while overcoming the allergy to self-promotion (80:34-81:11).
Audience Engagement: Comments can be paywalled; reply functions can be private—community engagement is central (75:28-77:20).
Serialization & Bundling: There’s opportunity for book serialization, bundled subscriptions, and creative cross-promotion (83:15–86:55).

9. Substack’s Future and Technology

AI Features: While wary of AI hype, Substack is adding features like auto-generated read-alouds, video/audio editing aids, and live conversation tools, aiming to “make it magically do the things you want it to do” (59:48–60:36).
Expanding Genres: From heterodox commentary to crypto, mainstream politics, and fiction, Substack’s popularity has moved in cultural waves (87:26–88:20).
Defending Creators: Programs like Substack Defender provide legal support for independent journalists against intimidation (88:46-91:01).

Notable Quotes & Memorable Moments

On the Big Vision of Substack

“I think you could power a renaissance…by giving kind of like the tools that the creative class need, you could actually create something that really meaningfully changed the world.” – Chris Best, [03:15]
On Algorithmic Discovery vs. Human Will

“Algorithms are just technology. They are a way to amplify the will of the maker of the thing.” – Chris Best, [11:08]
On Journalism and Institutional Pushback

“The narrowing of allowable perspectives reached a fever pitch and jettisoned a lot of the original thinkers. The people who were least likely to go along to get along were the most likely to get [pushed out].” – Chris Best, [21:57]
On Social Media Dynamics

“You can, with some structure and with some giving people the right tools and the right power themselves…have something that actually works and is beautiful and that people are free.” – Chris Best, [48:56]
On Overcoming the Social Media Mob

“As painful as it was, we did just sort of hold firm...a lot of our success was just not giving in, like not getting tilted, just being like, yep, everyone's mad...But we're not going to abdicate our responsibility or our judgment...” – Chris Best, [52:59–53:31]
On Substack’s Cultural Phases

“At any given time, it's tempting for people to, like, think that the current flourishing that's happening on Substack is the whole platform. But the reality is that it's this index fund of culture. It's got all these different things, and it changes all the time, which makes it fun.” – Chris Best, [88:20]

Timestamps for Important Segments

[00:23–05:17] — Substack’s origin and core philosophy
[12:07–14:24] — Why email and direct connection mattered
[20:35–24:02] — The state of media, journalism, and creators’ independence
[24:00–25:28] — Bari Weiss, Free Press, counterculture becoming mainstream
[34:34–39:31] — Substack app, discovery ecosystem, and algorithm design
[42:43–53:31] — Free speech philosophy, handling controversy, moderation
[55:13–58:33] — Features: podcasting, app usage, read-aloud, Substack Live
[77:24–80:31] — Creator advice: start, publish more, iterate, community engagement
[83:15–86:55] — Serialization, fiction, bundling, and Substack’s future
[88:46–91:01] — Substack Defender and legal support for creators
[64:24–69:15] — The complex relationship with Twitter, link throttling, and free speech
[72:24–75:28] — Contrast with Medium & Patreon

Episode Takeaways

Substack emerged as both a response to media industry dysfunction and an experiment in creator empowerment, leveraging direct connection and sustainable business models.
Independence for writers—and now audio/video creators—is nurtured not just by product features, but by principled stances on free speech, ownership, and platform incentives.
The platform is dynamic, riding successive cultural waves, adapting features, and reconceiving the media-company-of-the-future.
Substack positions itself as an “index fund of culture,” a bustling digital bazaar where new cultural movements can gestate, flourish, and, sometimes, become the new mainstream.

For creators and readers alike, Substack represents a hopeful experiment in what the next era of the Internet’s intellectual and cultural life might look like.

Loading summary...

Transcript

Narrator/Announcer (0:02)

Tetragrammaton.

Chris Best (0:23)

I've always believed that the things you read and the media you consume in general is not just how you spend a big chunk of your life. It changes you. And so great writing and great culture in general is this deeply valuable thing. And so I was like, I should write. How hard could it be? I would love that. I have ideas. I know how to type. Like, I'm a programmer. I love reading. And I started writing what I thought was going to be an essay or a blog post or a screen of some sort, like, detailing my frustrations with the media economy on the Internet, kind of just complaining in broad strokes. Look, the Internet came along, smashed a lot of the business models that used to sustain culture and hasn't really. I mean, it's created a lot of wonderful things. There's been a lot of promise, but it hasn't yet replaced, especially the economic engines that made those things go in a way that was satisfactory to me. And I was just kind of whining. I was going off and saying, wah, wah, Craigslist killed the classifieds, and maybe Facebook is not an unalloyed good. And I sent it to my friend Hamish, who's actually a writer, and he let me down very gently. He's like, these are all good points you make, but it's 2017 and you are not quite as original as you think you are. Other people may have noticed that some of these trends are going on, but he's like, here's how you could make this essay you're writing better is you should add a section that just says, so what do you do about it? How could this be different? It's easy to complain. It's easy to say, here's everything that's wrong. It's much more interesting, though. It would be more interesting as a reader to have a theory of what could a new and better thing be? And we started arguing, basically. And that argument turned into what became the core idea for Substack.

Interviewer (2:22)

And what was the core idea?

Chris Best (2:23)

The core idea is that the writers and the people who make the culture are the heroes. And they need independence in order to give the thing they have to give to the world. They need the freedom to make the things they want to make. And they need to be able to make money. And not just make money, incidentally, but to be able to make money doing the work they believe in. And that if you can create those conditions, not only will it appeal to the best writers, the best makers, the things that will get created will be different and better.

Interviewer (3:04)

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

Chris Best (3:15)

Yeah, we were arguing about the thing. And I've always felt that if you. You sort of need two things to have a really worthwhile idea in technology. You need to have sort of what I think of as the science fiction vision, sort of a grand, important idea for how the world could be different that actually matters. And you need to have sort of a humble beginning. You need to have, like a first step that you can actually take soon to be able to make progress towards that thing. You don't have to know how it connects. I don't think you can have this kind of foggy city on the hill, and then you can have this next thing that you do. You have to have some belief that you're going in the right direction, but you don't have to know where the rest of the path lives. And as we were arguing, we sort of realized we were developing this grand science fiction vision, this idea that you could make a new economic engine for culture. I mean, ultimately, to me, it's like, I think you could power a renaissance. Not as in we would be the ones to do it, but by giving kind of like the tools that the creative class need, you could actually create something that really meaningfully changed the world. And we had this very simple place to get started, which was this idea of a paid email newsletter. And there was already people that were doing this in the world. There was this guy, Ben Thompson, who wrote a thing called Stratechary that was like a tech business newsletter. You know, he was writing this thing from his bedroom in Taiwan, making millions of dollars a year, so sending out this email that people paid for. And we looked at that and we were like, hey, that's something new and better is getting made. And is successful. Successful in that it makes some money, but also successful in that it's making something that people really value. And it works today for this person, and there's no reason it shouldn't work for some more people. And it is actually a viable kernel of this much larger thing.

Chris Best (34:34)

So we started working on that several years ago and it was kind of the same story of originally I didn't want to have anything be free. I was like, we're going to be really pure and nothing can be free. And then it turned out that the free thing was an important part of how this worked. And we were sort of like that with the discovery piece, right? We were like, hey, we're going to build an app, but it's going to be purely about long form. It's going to be about only the things you're subscribed to, because that is the core, which was true. But it turned out that as we were building this platform for people to have this direct connection with their audience, one of the most important things they could do was to grow their audience and get in front of new people. And so we were. For a long time, Substack existed in a world where we had these lofty ideas about creating a better incentive structure that would enable better things to flourish. But in practice, if you were writing on Substack, you were still downstream of the existing social media apps. If you were coming from legacy media and you had a massive audience, you could just bring your audience sometimes. But if you wanted to grow, if you wanted to be a new person, you couldn't grow on Substack. You had to go to Twitter or you had to go to Facebook, or you had to go to one of these other platforms. And that was a problem. Both sort of at the science fiction vision level of we're trying to make something different, but we're actually still sort of wedded to this thing. And it was a practical problem, because those companies don't have a particular interest in helping you take your audience and go and own it. And you could have things like, you know, Mark Zuckerberg would decide, we don't want to be in politics for a bit because I was mistreated over the Cambridge Analytica thing, and we're just not going to have politics as much on Facebook. And if you're a political writer, that's a big problem. Or, you know, we got in a spat with Elon around the Totes launch, and so we sort of realized if we wanted to make the fullest version of this thing we were dreaming of, there was a piece that was missing. There has to be a place where you can go and discover things in the world where you can go and, like, be part of a larger conversation. That's a necessary piece of the ecosystem. We were plugging into those pieces that already existed, and that was imperfect, and we wanted to make our own. And we knew that was going to be a crucial thing to do. We also knew it was going to be really hard to do. It's like spinning up a new social network is famously difficult. But we started working at it, and it took a few years, and I would say towards the end of last year, we sort of got it working. When I say working, I don't just mean people are using it and looking at it and spending their time there, but it's generating Massive growth and revenue. People are discovering things that they love enough to pay for, and it's driving a large fraction of people's growth on

Chris Best (49:06)

That one was kind of like right wing content. It was like, hey, there's offensive stuff from the, from the far right. And it's true, there is some far right stuff and there's far left stuff and there's, you know, offensive, offensive things of all. Of all stripes. Well, here's another, like, here's another because there's been a series of controversies of like, why is thing X allowed on substack? One of them was kind of like, what's going on with trans issues? One of them was this kind of, you know, why are you allowing right wing people? But the other one I'm now remembering was, was sort of COVID skepticism, right? There was people who were running the gamut from, you know, are these vaccines good? To like, where did this virus come from? To are the measures we're taking against it the right ones? And there was really, really strong pushback and a strong sort of cultural and sometimes legal thing that was like, you know, you can't let people say this stuff. You can't let people question these things. And we took the position that, like, you gotta let people question. Question this stuff. And I think some of that stuff, you know, in, in my judgment is crankery, right? Like, I think a lot of the. The anti vax stuff is not right and probably does harm and is. Is net bad. And some of it turned out to be right, probably. Like some of the, you know, people who are questioning some of the measures, I think you can, I don't, I don't know if we've resolved the question of where Covid came from, but I think it's at least an open question that's legitimate and to debate and shouldn't be, you know, shut down with accusations of racism or whatever. And that was. Yeah, that was another kind of a moment for me that exposed why this stuff actually matters. You have to let people ask questions. You have to let people challenge the received wisdom, even if they're wrong, even if they're. If they seem crazy. I just think that's like an. A crucial part of a free society. And, you know, substack has been that. We've drawn a lot of criticism for that. Here's another piece of. This is like. I think there's like a. There's a place where I saw a lot of companies go off the rails. I think especially in sort of like, 2020, around that era was like, the way these things would. Would work was there'd be like this, you know, you get like, a social media mob that would show up. Any surface on the Internet that you would open would just have all of these people shrieking at you and telling you you're the worst person and threatening you and all of this stuff. And I think part of what social media does is create a false illusion of consensus. It would feel like everyone was mad at you or everyone hated you, or everyone thought you were. What you're doing was crazy, when really it would be like, there's, like, a couple hundred people that are really ginned up about this. And I think it's very tempting, if that happens to you, to give in and to say, okay, okay, okay, I. I hear you. I'm listening and learning. I'm gonna do this first step to start making this better. And I think as soon as you do that, you are lost. Either you're in control or the mob is in control. And as soon as you, like, let the mob start to be a little bit in control. It's like it devolves and devolves, and nothing satisfies it. And so we. One of the things that we did, you know, and this. It feels this way in the press, and it feels this way when you get these social media things is as painful as it was. We did just sort of hold firm. We wrote a few essays in advance outlining our philosophy about, you know, free speech and freedom of the press and why we were doing what we were doing and why things were the way they were. And we could sort of consult back to, you know, what we had written with cooler heads and then a lot of what I think of as our success was just not giving in, like not getting tilted, just being like, yep, everyone's mad. The people who are our customers, who are concerned, we'll talk to and we'll empathize with them and tell them what we're doing. But we're not going to abdicate our responsibility or our judgment to the critics in the press or to the critics on social media. I think that saved the company, basically. I think being willing to stand up in those moments feels hard, but maybe this is the advice I would give to somebody going through that is like, stick by your principles. If you're going to get smashed, get smashed for doing something you believe in, because that's worth it.

Chris Best (67:11)

Although I would say, given what's happened since, maybe questionably so, but at least on that core idea of like, hey, there just has to be a. There has to be freedom for people to say the things they believe and want to say. He at one point floated the idea of Twitter buying Substack and me coming to run Twitter just as, like, a thought experiment style thing. And when we were about to launch Notes, which is like our feed, I kind of gave him a courtesy heads up. We'd been having this conversation. I was like, hey, we're launching this thing. We think it's important. It's something we've been planning for a while. We're not trying to mess with what you're doing. But we launched it, and he was very upset. He actually asked me not to launch it. He was like, don't launch this thing, basically because he saw it as a Twitter competitor. And I think there was a moment there where there was this meme of, is Twitter actually going to fail? Is this going to tip over? Are people going to switch over to Blue sky, switch over to Threads, or switch over to somewhere else? And so he saw us launching this feed as kind of, I think, a declaration of war. And he banned all mention of Substack on Twitter. There was a week where not only could you not share a Substack link, if you just said the word substack, nobody would see your thing. And if you search for you, literally you'd search for Substack on Twitter, it would say, no results. Doesn't exist. We were like, voldemort. You can't say the name. And that. I think after some backlash, they canceled that policy pretty quickly, but left in place a bunch of kind of like, underhanded things that would hurt traffic. I think Substack in the New York Times were the two sites for a while that got the treatment where you would click on a link and it would go there, but it would delay for five seconds. Like you just click and it would just be like, spin. And five seconds sounds like a short amount of time, but in, you know, software as an eternity.

Chris Best (72:31)

So the biggest difference from Medium is the business model. My view of Medium is they took sort of the underpants gnome theory of building one of these things, which is like, step one, get a bunch of attention. Question mark, question mark, question mark. Step three, profit. And so they sort of had this period of trying out a bunch of different business models, one of which was very similar to the substack business model. But through most of Medium's history, there hasn't been any idea of, like, direct connection or ownership as a creator, as a writer. And so, like, on Medium, you'd pay five bucks a month for all of Medium and it would be sort of Netflix style. It would like, give you some slice of the thing if you click on a thing. And what that means is if you're making stuff on Medium, you're kind of like playing to the algorithm all the time to get anywhere. And very early in, when we were still in yc, actually, Medium used to publish. Here's what the top earning writer on Medium made last month. And we would look at it and be like, there's people on Substack that are making more than that, and they're not making more than that because they had the one hit that they could never replicate that happened to get a gajillion clicks and the algorithm doled out a big paycheck. They've got that because they've got a loyal audience of people who value what they do. It's just such a better deal creatively and financially to have some connection with your audience and to have people who are showing up and paying for you. And so I think it was able to attract a much better caliber of writer over time. And then Patreon is very interesting because Patreon is similar in some ways. I've talked to Jack a few times, and I think maybe early on I would have said Patreon was doing the thing where they were trying to be very pure. And they're like, we're really just going to be about the payment relationship. Jack's a musician. He's like, I want to be so creator, you know, focused and friendly that I'm never going to, like, try to impugn on the relationship at all. So we're just going to handle the payment for you, and we're kind of not going to do the rest. And you're not really consuming the content on Patreon. The prototypical thing is you're a musician or you're a YouTuber or you're somebody. And they didn't want to do discovery, they didn't want to help you grow because they felt like it would be sort of tarnishing the pureness of the thing. And I've argued with Jack about that over the years. My view is he's come around to my way of thinking, and they're looking at Substack saying, oh, one of the most important things you can do for creators is help them grow and find an audience, especially new creators, especially the next generation of people who are trying to come up. And now, again, I'm biased, but my view is they're just copying a lot of the things that Substack is doing, which I think are good ideas. But in terms of like having a network, that's a place on the Internet that you go, I don't think Patreon has achieved that yet.

Chris Best (88:46)

Substack Defender. Oh, man. So we had a thing that kept happening because you'd have these especially, like, local journalism. This happened a lot where somebody would be covering a local business or politician negatively, and they'd be some independent person that's just trying to. Maybe there's no local newspaper anymore, but they're taking up the thing and they'd write some negative story and they would get a really scary letter on legal letterhead that basically says, we're going to ruin your life unless you shut up. I mean, there's very strong legal protections for journalism and speech and criticism in this country. And so very often these were just bogus claims or claims that did not have a very strong chance of actually winning in court. But the ability to make the threat, if you're an independent person can be kind of debilitating, because even if you defend. Even just the cost of defending yourself can be very high. And you don't really know how are they going to be able to find something or what is this thing? And so we created this program called Substack Defender that was basically like, we're going to have a fund for picking up defenses of these things that anybody can apply to. We'll pick which ones we take and we're going to pick a few things like this where somebody is kind of trying to do censorship by lawfare. I think of it just like really vigorously defend it and put a bunch of weight behind it, put a bunch of money behind it, try to like, you know, publicize it if necessary. Because the imbalance was if you're some business person or government person, it's basically free for you to send a scary, scarygram. Yeah, there's no real cost to you. It's cheap to get a lawyer. You pay a lawyer, they write up a meanly worded thing. You send it to somebody, it makes them afraid to do the work. But when you do that, there's a chance that there's a very well funded legal NPR defense that swings to their aid suddenly that can tip the balance of power back in favor. And by doing even a relatively small number of those, you can help create a climate where it's not costless to harass journalists.