How blogging went legit, with Substack CEO Chris Best
Patrick McKenzie is joined by Chris Best, CEO of Substack, to discuss how the platform created new economic infrastructure for independent media. They explore Substack's evolution from a simple newsletter tool to a full media network, the company's principled stance on press freedom during the "cancel culture" years, and Substack Defender, their legal protection program for writers facing lawsuits. [Patrick notes: As always, there are some after-the-fact observations sprinkled into the transcript, set out in this format.]
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Timestamps for Video:
(00:00) Intro
(01:27) What is Substack?
(01:39) The evolution of online publishing
(02:06) The business model behind Substack
(04:33) Challenges and opportunities in media
(08:46) The paid newsletter model
(11:40) Revenue guarantees and early successes
(13:51) Substack's impact on journalism
(18:45) Freedom of the press and Substack's stance
(20:10) Sponsor: Mercury
(21:26) The role of Twitter in modern journalism
(22:31) Epistemic infrastructure and independence
(24:18) The impact of cancel culture on careers
(24:55) Substack as a safe haven for writers
(31:39) The evolution of media formats on Substack
(36:59) Substack Defender
(43:08) Building a network and future of media
(46:50) Wrap
Transcript
Patrick McKenzie
Hello everybody. My name is Patrick McKenzie, better known as patio11 on the Internet. I’m here with Chris Best, CEO of Substack. Thanks for coming on the program.
Normally on this podcast we talk about infrastructure, and I slot Substack as infrastructure for thought and thought leadership. That’s near and dear to my heart, even though I don’t personally use the platform.
For the five listeners who don’t know yet: what is Substack?
Chris Best
Substack is a media network where you can publish independently and connect directly with your audience.
The evolution of online publishing
Patrick McKenzie
In the grand history of publishing on the Internet, I see Substack as an evolution. First blogging, then social media—originally “microblogging.” Substack stepped into a niche: we’ve had ways to publish for a long time, but not a broadly adopted business model. Substack popularized one for both sides of the market.
On the demand side, you made the case to certain segments of employed people that they should spend more on a Substack-shaped thing than they currently do. On the supply side, you made it legible to public intellectuals—Matt Yglesias, Byrne Hobart, and many others across politics, finance, and tech. Those communities were early, large adopters, both as readers and writers.
Chris Best
Scott Alexander is one. Paul Krugman has a Substack now, which is exciting.
Challenges and opportunities in media
Patrick McKenzie
For a while it felt like every few weeks someone quit a prestige media desk to launch their own Substack. Now you even see the flow go the other direction—for example, reporting that The Free Press is in acquisition talks with CBS.
Newsletters obviously predate the Internet, paid newsletters too, but there wasn’t an obvious modern platform for them. Substack made a splash big enough that the form factor is almost synonymous with the brand; people say “I love your Substack” to me, and I don’t in fact have one.
Chris Best
We can fix that.
Patrick McKenzie
My producer just won a bet that you’d say that. Be that as it may: why did it work? Why did Substack successfully make the two-sided marketplace happen?
Chris Best
You hit it: the business model. That’s what we set out to change from the beginning. The company was born from an essay I was trying (and failing) to write about the state of the media economy on the Internet.
The role of engagement in media
The Internet wiped out a lot of the business models that supported great media and culture. What replaced them in the first iteration—the attention land-grab—was phenomenally successful for the platforms and created a lot of value, but with a fundamental flaw: the incentives imposed on the company, then imposed on the network, created a bad mimetic evolutionary landscape. The networks we spend time on drive us nuts.
Patrick McKenzie
“Sort by engagement” as original sin. You don’t even need a capital-A Algorithm to see the pathology. Forums where “most recent comment” floats a post are taken over by flamewars and the posters whose stamina and personality brings them back to the war daily.
Chris Best
Exactly. Old news had “if it bleeds, it leads” and “if you want a crowd, start a fight.” Those reflect human nature. But when you globalize it and make the attention economy highly efficient, you get new, worse equilibria
The birth of Substack
I sent the essay to my friend Hamish, who gently said: “We know. It’s 2017. Newspapers are in trouble, Facebook isn’t an unalloyed good. The interesting question is: what would you do about it?” That pushed us to think in terms of a new economic engine for culture.
If you want to fix the problem, the answer isn’t primarily product or tech; it’s actually in the business model—the social contract. You need different foundational assumptions. At the core: what does the network know how to value? Sort-by-engagement networks value your time, not what you value. A cheap eye-grab or an outrage spike “counts” the same as a life-changing essay. It’s far cheaper and faster to produce the former, so incentives tilt the landscape toward it. To escape, you need a model that can value what readers value.
We set out to build that, deliberately, with a long-range plan. That mattered.
We also had an MVP. We’d watched Andrew Sullivan’s Daily Dish and Ben Thompson’s Stratechery. The paid email newsletter looked like a kernel of the new model: anyone on the Internet can subscribe; the writer’s incentive is to earn and keep the trust of people who deeply value the work, not just draw a crowd. A relatively small, global audience that values the work can be economically strong. So we made it dead-simple to create a paid email newsletter—and that became the kernel of what people think of as a Substack publication.
Making paid newsletters accessible
Patrick McKenzie
A paid email platform isn’t rocket science, but for a typical would-be writer it might as well be. Ben Thompson could stand up something competent himself or hire a Rails dev. The average newsroom writer? That might as well be on the moon.
Chris Best
Exactly. Ben could duct-tape a stack—mailing list, WordPress, billing—grind for months before seeing money. He documented the steps. Most people can’t replicate that.
Activation energy matters. The idea of starting a Substack felt weird and new, even if it was actually a good idea for many people. We had to lower the barrier so one person could do it, quickly. Once some did, examples unlocked the next wave. But you only get that flywheel if the power of the tech is delivered in a very simple way.
Revenue guarantees and early success
Patrick McKenzie
Early on you ran revenue guarantees for lighthouse writers. Let’s talk about the mechanics of that program.
Chris Best
That was a program we ran for a while. At that point we’d seen enough Substack launches to know it was working. For some writers we could say with confidence: you are going to make serious money on Substack. Matt Yglesias, for example, has written publicly about his version of this. We told him: you should absolutely do this. But he quite reasonably asked, “How much risk am I taking?”
So we created a construct that set a floor for the first year. You’d make at least a minimum amount. If you made more, we’d keep a portion of the upside. If you made less, we’d protect the downside. After the first year it reverted to the standard Substack deal: free to publish, we take 10% of subscriptions.
For some people that was decisive. Matt blew through the minimums, which made underwriting the deal a great business for us. More importantly, it lent confidence when there weren’t enough examples yet to show success was possible.
Substack's impact on journalism
Patrick McKenzie
It also helped cross the chasm between the “bloggers-in-bathrobes” phase and being a serious competitive option to working in high-status New York journalism. Not that Substack is only for journalism or commentary, but for someone who could otherwise be at The New York Times or similar, it took a while for that to be understood in New York the way it was obvious in tech. Four or five years ago it was already clear that if you have some personal brand, some writing ability, and something interesting to say, Substack transforms the economics of media. If you’re the star columnist at the Times, the world is your oyster. If you’re the fortieth most popular columnist… you should probably be on Substack.
[Patrick notes: Not to say I called it but, ahem, I called it. The shape of the future was obvious even in 2020.]
Chris Best
And it changes things even for people who don’t go independent. Some negotiate much larger salaries because both they and their employers know the option exists.
Patrick McKenzie
I know a few of those cases. I’m glad—for you and for them—that Substack is the BATNA. [Patrick notes: Best Alternative to Negotiated Action, i.e., “What’s my fallback plan if this salary negotiation with a traditional media outpost doesn’t go the way I want it to?” For years, media companies treated writers as if their BATNA was penury.]
Chris Best
In those days I’d give people a little speech. Here’s what you care about: freedom, money, prestige. I can’t give you prestige. But the other two—you’ll have so much more freedom, and you’ll make so much more money. It was exciting to be able to offer that.
Patrick McKenzie
To what degree do you think you can’t offer prestige anymore? Because when I look at the people joining Substack today—either as solo entrepreneurs or as part of publications with payrolls larger than their founders had—I see people with very credible prestige alternatives.
For example, Kelsey Piper recently left Vox and joined The Argument, which is on Substack.
Chris Best
I think that is changing. In 2020 it was true: Substack wasn’t prestigious. People said to me, accusingly, “Substack is just blogging with a business model.” And I said, that’s no small thing. That was the main problem with blogging: it was great, but it lacked a business model.
Patrick McKenzie
Both of us have been around the Internet long enough to remember people casting back to the “golden age of blogging” and asking why that style of writing disappeared. My answer: most of the people you loved from that era are still with us. They just took career upgrades as a result of what they were doing then. Now Substack is one path for those upgrades.
Chris Best
Definitely. And I think prestige is coming. Maybe not full-blown prestige, but there’s a sense of intellectual ferment developing. Derek Thompson wrote, when he joined Substack, that he’d simply found himself reading it all the time — that the conversations he found stimulating were happening there. He felt on the outside looking in, and thought: regardless of prestige, this is where the interesting stuff is. That’s powerful.
Patrick McKenzie
That’s why I joked there are only five people in the audience who haven’t already seen Substack in action. One, because Substack URLs are everywhere if you work in policy or commentary. Two, because it’s genuinely part of the conversation.
Kelsey Piper told me just yesterday that her new publication The Argument is already getting serious responses from the usual suspects, who are treating it as a peer in the discourse. That took time to build.
It’s easy to forget there was a time, not so long ago, when giving people a business model on the Internet was controversial. I recall the blowback when right-leaning writers — Matt Yglesias, to pick one example — started earning directly from readers. [Patrick notes: Flagging that my tone of voice here was somewhere between “wry exasperation” and “acidicly sarcastic.”]
Substack’s choices in 2020–21 were not popular everywhere, but they seem to have worked out.
Freedom of the press and Substack's stance
Chris Best
From the beginning we took a strong stance in favor of freedom of the press. We think it’s the right thing for our business and our platform, and we designed them accordingly. A free press is fundamental to a free society.
We’ve gone through periods where that drew a lot of heat. I always knew it would happen, but I’ve now lived long enough that the polarity of who’s angry has flipped. Today the inverse of some of those earlier arguments is playing out. But I think it matters, and I’m proud that we’ve been consistent.
My experience is that there are relatively few consistent defenders of press freedom. Whoever is out of power always wants it; whoever is in power always wants to wield power against opponents. The temptation is perennial. That’s why it’s valuable for us to hold the line.
Twitter's influence on journalism
Patrick McKenzie
Your co-founder Hamish McKenzie wrote a few years ago that Twitter had changed the production function of journalism. Reporters were spending huge amounts of time with colleagues, sources, bosses, and activists on Twitter. The conversation became more insular than even the Brooklyn media scene usually is. That narrowed the range of acceptable opinions in newsrooms. I think that dynamic was part of the pressure against Substack’s free-speech stance.
Free speech has many defenders again today. That sounds like it should be a vacuous statement in the United States, but for a few years it wasn’t. Substack’s sometimes unpopular choices in 2020–21 are now looking vindicated. It’s worth remembering they were not easy calls at the time.
Chris Best
Thank you — that means a lot. If we frame Substack as epistemic infrastructure, it becomes interesting to ask: what properties do you want that infrastructure to have? Independence is one. If you have an opinion or a perspective that’s outside consensus, you should still be able to share it.
Freedom to publish is part of it. But another part is whether there’s a countervailing reward for being out of consensus but right — or even just out of consensus but interesting. That can be valuable too. One way epistemic infrastructure fails is if the punishment for independence always outweighs the reward. Then you get stagnation. We’ve seen that dynamic at different ideological poles. What we need is infrastructure that robustly supports independence.
Patrick McKenzie
One of the implicit weapons of the cancel-culture years was the risk that if enough people on Twitter were sufficiently annoyed at you, you could lose your job. And not just the current one: in industries with tight networks, you could be branded as damaged goods and effectively blacklisted.
Chris Best
Your career might be over.
Patrick McKenzie
And it didn’t require Joseph McCarthy keeping a formal blacklist. The relevant parties already had Twitter lists.
Substack's role in modern media
Substack changed that equilibrium. We’re not talking about people outside the pale of polite society; we’re talking about voices for which there is a real market. If a prestige newsroom no longer wants to publish you, you can take your audience to Substack. That improves the discourse on Substack, but also improves the discourse at traditional outlets — reporters don’t have to be as afraid.
Chris Best
And even if they never leave, it changes the equation. If you’re a star columnist, you can demand a raise. If you’re a solid but not star columnist, you can demand more freedom. Because the ability to gate-keep what gets said is lessened.
The impact of cancel culture on journalism
Patrick McKenzie
And if you do get pushed out, you can continue on Substack. Realistically, the people who provoked the strongest reactions also motivated the most subscriptions. That strategic calculus matters.
Chris Best
Exactly. Readers respond by saying: this is valuable to me, I want to support it, I’ll pay for it. That creates a countervailing force. As the pressure against independence gets stronger, the audience pushback grows too.
Patrick McKenzie
Which made cancel culture less of a super-weapon. If the result of a campaign is not that someone can’t put food on the table but that they launch a Substack and get a raise, the incentive to wield that weapon carelessly declines. The healthier dynamic is: if we disagree strongly, we should write our disagreement in our own space, in reasoned form.
The evolution of blogging and discourse
Chris Best
That’s the lesson of blogging: “Somebody is wrong on the Internet” is the greatest force for discourse.
Patrick McKenzie
“Someone is wrong on the Internet” has created enormous value. We should urgently hope there are more people wrong on the Internet next year. We’re working on it already this year.
This isn’t a partisan podcast, but I think there’s growing recognition across the aisle — where it was thinner a few years ago — that you can’t cede the Internet to only those willing to show up. That’s part of why movements like Derek Thompson’s Abundance Agenda are interesting: they expand the coalition’s acceptable range of options. And the new Schelling point is on Substack.
Chris Best
It’s not just what range of views is acceptable; it’s what depth and nuance the format rewards.
Patrick McKenzie
Exactly. Traditional media often says, “We love what you have to say, but give it to us in 800 words once, and maybe we’ll revisit in three years.” That’s frustrating.
Chris Best
And social networks compress even further. Short posts are powerful, but the incentive landscape they create rewards the “fittest” ideas in an evolutionary sense, not the truest ones. Compression strips out nuance. By contrast, when more people can publish on Substack, we get a wider range. This year both Gavin Newsom and the State Department launched Substacks. That means longer-form arguments, disagreement in writing, and more space for ideas to develop. The more of that we have, the healthier the ecosystem becomes.
Patrick McKenzie
I can’t imagine anyone preferring fifteen-second soundbites over multi-page, reasoned arguments for how policy should be conducted.
Chris Best
We’ll always have both. Short soundbites are locked in. The question was whether we’d also get the essays. Now we will. Even if the audiences are smaller in absolute numbers, they exert outsize influence in the world of ideas.
Patrick McKenzie
Exactly. Democracy depends on broad participation, but it also depends on a political elite that produces and refines culture. The 8,000-word essay dueling in the pages of a newspaper has always shaped that conversation. The Internet removes column-inch limits; there’s no reason not to fill it with better arguments about what kind of future we want. Then voters can make informed choices between them.
Substack's expansion into podcasts and video
Substack started as a newsletter platform, but you’ve broadened. You now support podcasts, and I understand video as well. Do you want to talk about those?
Chris Best
From the beginning, the vision was never limited to text. We started there because it was natural for us, and because writing was the right wedge. But we built podcast support early. In some ways a podcast is analogous to an email newsletter: you have a direct connection through feeds people already use. We also experimented with video years ago. That didn’t work in email, but now with the Substack app it does — people use the app to keep up with subscriptions and discover new things, and podcasts and video fit.
In the early days, what Substack did was take capabilities that already existed in theory and make them accessible in practice. Lower the activation energy, make it simple enough that far more people could do it. I sometimes joked: we’ll do everything for you except the hard part. Writing something worth paying for is hard. But if you can do that, we’ll handle the rest.
AI and the future of media production
That’s true today, and now we can do the same for podcasts and video. The AI revolution makes it possible to go even further. Take a podcast conversation: we can automatically upgrade audio, create an edited podcast, generate a YouTube video, cut social clips, and soon translate into multiple languages. Substack Live, for example, lets you start what feels like a FaceTime call, people can watch live, and then the system spins out the artifacts automatically. We’re trying to make it as easy for someone with something interesting to say on camera as it is for a writer to publish an essay.
Patrick McKenzie
People outside media often underestimate the production function. There might be one name on a byline, or one face on camera, but behind that is usually a team: producer, editor, transcriptionist, social manager. AI lowers the minimum team size. If you’ve got one person with interesting ideas, that can now be enough to launch a publication.
Chris Best
And that matters most at the start, when activation energy is highest. How many conversations never happen because the start-up costs are too great?
Patrick McKenzie
Exactly. Most small media businesses don’t get off the ground, or don’t survive long enough to hire staff. It was more than ten years before my own blog was in a position to support help permanently, though thankfully it does now. AI plus Substack lowers that bar: fans you’ve built elsewhere can follow you, start paying, and by month one or three — not year ten — you can afford an editor, a transcriptionist, a social manager. You start backfilling, rather than waiting for scale.
Substack defender
Patrick McKenzie
You’ve also used the network to accelerate beyond just tools. Journalism has always had this problem: occasionally you write about someone powerful, and they don’t like it. Their lawyer sends you a nastygram. For an independent writer, that’s terrifying. What did Substack do to change that equilibrium?
Chris Best
We noticed it especially in local news. A politician or businessperson would be covered legitimately, but they’d fire off a threatening letter. The independent writer would wonder: what now?
The core problem was an asymmetry of costs. It takes almost nothing for a powerful person to send a letter. Even if you’re confident it’s bogus, just hiring a lawyer feels ruinous. You don’t feel safe pushing back.
So we created Substack Defender. Writers can apply, and if accepted, we foot the bill for their legal help. The biggest reason was to flip the incentive structure. If you’re trying to silence legitimate journalism, we can make it costly. We’ll hire a strong lawyer, make noise about it, and demonstrate that pushing around an independent writer may backfire.
The point isn’t that we’ll fight every case forever, but that if you think you’ll meet vigorous resistance, you’ll think twice about sending the letter in the first place. And it’s worked. We’ve taken cases, won convincingly, and I’m proud of it.
Patrick McKenzie
I love this because it’s like insurance, but better. Standard media liability insurance costs me around three thousand dollars a year. If I’m sued, Berkshire Hathaway is technically on the hook to defend me, which is nice. But the incentive for an insurer is to settle: stall a little, then pay out quietly.
[Patrick notes: Uncompensated and unasked-for plug for Three Insurance, which is indeed a Berkshire Hathaway subsidiary. It has coverage basically equivalent to errors and omissions, general liability, and a media rider, for businesses which typically don’t have size and sophistication to understand what that gloss means. In effect this means that if someone sues Kalzumeus Software, LLC then rather than yours truly stressing about it a bored lawyer who works for Warren Buffett handles the correspondence, shakes the nuts out of the tree, and eventually settles the nuisance suits for $25,000-50,000 (typical insured losses for E&O claims at my previous carrier; insurance regulatory paperwork is thrilling reading) while promising that a plaintiff who doesn’t want to settle will need to try outspending Warren in court.]
Patrick continues: Substack’s incentive is different. You don’t want to quietly settle for fifty grand. You want to make it symmetrically costly—or even asymmetrically costly. “The last five people who tried this didn’t enjoy the experience. Do you want to be number six?” That deterrent gets stronger every time you use it, and stronger as the network itself grows.
Chris Best
Exactly. An insurer can’t scare off the fires it insures against. But we can deter the worst abuses of nuisance legal threats. That’s fun, and important, to do.
Patrick McKenzie
And it scales with the network. As Substack gets treated more and more seriously — even in prestige media circles — a legal fight carries real reputational risk for the would-be censor. Do you really want that fight?
Chris Best
And people should know: if you’re considering suing a Substack writer, I personally take great pleasure in fighting those battles.
Patrick McKenzie
It reminds me of Cloudflare’s stance toward patent trolls. The troll calculus is that settling is cheaper than fighting: tens of thousands to settle, millions to defend. Cloudflare flipped that script. “Come after us, we’ll burn down your portfolio.” Substack doesn’t need to burn down an industry, but if you credibly signal “this won’t work out well for you,” then people choose other means of resolving disputes.
And importantly: if you disagree with something a Substack writer has said, there are plenty of places on the Internet to publish your response — including Substack itself.
The growing network and future of Substack
Patrick McKenzie
So, where do you see the Internet and the media economy heading over the next couple of years?
Chris Best
One point I should have made earlier: Substack began as a tool. Push a button, lower the barrier, get started — that was great. But over time we realized being a tool wasn’t enough.
If you want to succeed on Substack and you don’t already have a massive audience, you need ways to grow. For years that meant relying on Twitter, Facebook, LinkedIn — wherever. But that makes you downstream of their incentive structures. Your top of funnel depends on what works there.
And you’re subject to their trust-and-safety and management decisions. Zuckerberg decides to de-prioritize politics, and suddenly political writers suffer. Elon bans Substack links for a week, and suddenly your reach collapses. If you’re trying to be independent, it’s rough to have your future contingent on those calls.
So we’ve been building Substack as a network. There’s the app, there’s substack.com. You can subscribe to what you already read, but you can also discover new writers. Being on Substack gives you exposure to a growing audience of smart, curious, high-propensity-to-pay readers. That’s our contribution: a real alternative to other networks, many of which are struggling right now.
Patrick McKenzie
And once you have that network, you get flywheel effects. More writers mean more readers; more readers mean more credit cards on file; lower friction for new subscriptions. It’s the App Store playbook: not just solve payments, but create the installed base. For anyone professionally involved in the life of the mind, odds are they already have at least one Substack subscription. Adding another is easy.
And you do the obvious but surprisingly hard things: make it simple to pay for writing on the Internet.
[Patrick notes: I had to physically restrain myself from launching into “I understand that doesn’t sound hard but I worked in payments for six years and…” because we were in the last few minutes of the interview.
Among many other things: you need to be prepared to mediate between Americans and Germans on the proper amount of ceremony that needs to be on an invoice for a business expense to be legitimate. There are many other pairs of nations, too, but that particular pair drive each other batty on this issue.
Many people assume it’s primarily culture but it is primarily tax policy: America has several thousand sales-/use- tax regimes and does not aggressively standardize on invoices as a primary enforcement channel for them. Sales taxes are relatively low (Chicago is nearly highest in nation at a hair over 10%). Much of the EU has VAT taxes, which are comparatively high (30%+) and VAT tax is effectively refundable. As a result, German accountants care quite a bit about the level of ceremony on invoices, without which they will fail to capture enormous cost savings on business inputs or, worse, be dragged into a high-stress conversation with the tax authorities.
If you want to accumulate another thousand stories like this one, Stripe—which does not necessarily endorse my personal POV with regards to the political economy of VAT taxes vis Internet publishing—is hiring.]
Patrick continues: That alone creates enormous value. Many thanks for pushing the ecosystem forward.
Chris Best
Thank you very much.
Patrick McKenzie
And now the traditional closing question, which I ask every week, even when the answer is obvious. Chris, where can people find you on the Internet?
Chris Best
Download the Substack app, or go to substack.com. And I’m there too — my personal Substack is @cb.
Patrick McKenzie
Wonderful. Thanks very much, and thanks to all of you for listening. We’ll see you next week on Complex Systems.
