The point isn’t just to make money—it’s to change the systems that human attention flows through. You can’t understand Substack without understanding this.
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In the Spring of 2018 I got invited by the CEO of Substack to come to Toronto for a couple days to hang out with the whole team—which at the time was just the three co-founders—so we could all get to know each other. They had just finished Y Combinator, raised a seed round, and were looking to grow the team. I was auditioning for the role of employee #1.
They wanted a general-purpose product builder who could come up with good ideas and take them from beginning to end without much supervision. Most importantly, this had to be someone who was on the same page philosophically, and grokked the founding vision.
On my end, I was looking for something exciting to build from the ground up at the intersection of media and technology. I needed it. I was less than a year past my startup failing, and a few weeks past losing my job as “Head of Product” at Gimlet, the podcasting network that would go on to be acquired by Spotify, because the company decided to stick to content and not build some of the tech ideas they had flirted with when they brought me on 9 months prior. I still remember the day I walked into a conference room for my regular weekly 1:1 with my boss. I knew something was up because he was usually completely relaxed, and treated me more like a co-conspirator than a direct report. But the mood was different that day when he said something like, “from the beginning you’ve been very clear you want to build something that could fundamentally transform Gimlet, but we’ve realized that’s not the path the company wants to take.”
The taste of defeat was still in my mouth when I flew to Toronto to try and wash it down with a little poutine, a lot of beer, and a healthy dose of the wild, uncomplicated optimism that’s only possible in the earliest days of a new venture. On that front, I got even more than I anticipated.
The atmosphere with Chris, Hamish, and Jairaj couldn’t have been more different from my old environment. I had teleported from the living embodiment of the “messy middle”—the grind of a mid-stage startup that’s doing objectively well but bearing the weight of complex execution challenges and massive expectations—to the early hours of a fever dream depicting a revolutionary new model for publishing. It was thrilling! I was already bought in on the vision before that trip, but spending three nights and days bullshitting with the founders made me somehow even more certain that this dream would come true, and that I could play a part in it.
The thing I didn’t understand going into it was that Substack wasn’t just about an economic trend of power flowing to individual writers thanks to the leverage technology gives them—it was about creating a morally superior playing field that could help heal our minds from the damage done by social networks. The Substack model wasn’t just a business strategy, it was a political philosophy, and I loved it.
I got the part.
Not many people know this, but the origins of Substack can be traced back to an essay that Chris, the CEO, wanted to write. (Appropriate, for a publishing platform!)
It was early 2017, and he had just wrapped up an 8-year run as the CTO of Kik, the company he founded as a college student. He had some newfound time on his hands, and the world was falling apart. This was the very beginning of the Trump presidency, the Scaramucci era, the “Obama wiretapped me” era, the “alternative facts” era—perhaps the most ridiculous era in American history. I don’t know if this context was specifically on Chris’s mind as he sat down to write, but I do know this: around this same time, Chris decided to write an essay about the problems created by the systems that control human attention.
He got to work, and then reached out to someone he thought would be able to help: Hamish, a journalist who worked with Kik as an editorial advisor. When Hamish read a draft, he said, “Yeah you’re right about all the problems created by advertising and social media, but everybody already knows this. The question is: what can be done? What is the solution?”
They kept working on the essay together, and in the process decided to start a company that could enact the ideology outlined in it. Philosophy first, company second. The essay was published on July 17, 2017, and is the first entry in the official Substack company newsletter.
The whole thing is worth reading, but to give you the quick TL;DR, basically it traces the history of modern publishing back to the decision in 1833 of a guy named Benjamin Day to offer his newspaper, The New York Sun, for a sixth the price of his competition. His strategy was to focus on sensational journalism to get broad reach, and make up for the losses in subscription revenue through advertising. That model has dominated media to this day, except it’s now broken, because Facebook and Google and Craigslist took all the advertising revenue. The answer is to build a new ecosystem where individual writers or small teams offer hyper-focused subscription products that add genuine value to readers' lives, rather than merely trying to trick them into clicking.
And then comes the key paragraph:
“We believe that journalistic content has intrinsic value and that it doesn’t have to be given away for free. We believe that what you read matters. And we believe that there has never been a better time to bolster and protect those ideals. Now, more than ever, publishers of news and similar content can be profitable through direct payments from readers. In fact, we are so convinced by this notion that we have started a company to accelerate the advent of what we are convinced will be a new golden age for publishing. The company is called Substack.”
Here the ideology motivated the business—not the other way around, with a pretty story painted on later to help employees to feel like they’re doing something other than enriching their bosses, as is the case with so many startups.
A year later Chris published a post about his love-hate relationship with Twitter, which took the ideology a step further:
“Twitter makes money from your attention, so they need to compel your attention. Sometimes that leads to good things, like connecting you to people and ideas that matter. But it also means that the addiction, abuse, and outrage that thrive on Twitter and other social platforms may be impossible to eradicate. So what’s left to do? You can change the rules. That’s why we started Substack: when readers pay writers directly, it’s a whole new game.”
In 2021 he got even more aggressive:
“Social media giants gave us rekindled friendships, family photos, even the occasional uplifting story or useful insight. But too much of what we’ve received has been toxic gruel, tube-fed (through aptly named “feeds”) by sophisticated algorithms designed to exploit our worst impulses and keep us agitated, excited, engaged.”
There are two central evils within the Substack ideology:
- Advertising. It rewards publishers for merely attracting attention, rather than creating things people genuinely value. When this is the dominant model for funding media, the media becomes dominated by sensationalism, frivolities, conspiracies, and tribalism.
- Engagement algorithms. All the algorithms see are engagement metrics, they don’t care what they put in front of our faces. But what we read matters, and the most viral content is not the most valuable. Virality favors emotions like outrage, so it manufactures it from nothing if necessary, and we become addicted.
Correspondingly, each evil has an antidote:
- Subscriptions. As Chris likes to say, people will ‘hate read’ things, but they won’t ‘hate pay’. When readers are asked to pay for content, they make their consumption decisions more consciously, as their better selves.
- Inboxes. Instead of endless feed-scrolling, Substack only puts content in your inbox that you specifically opted-in to receive. Whether in your email inbox or in a separate Substack inbox in their reader app, you only see things you decided to see. You are in control.
These moral convictions make the business of growing Substack complicated. If we lived in an alternate universe where a former YouTube PM or Stanford MBA was the founder of Substack, I think we’d see them take a vastly different approach. They’d make several moves the conventional wisdom says helps build power and network effects:
The first thing they would do is obviously build an advertising network. This helps lock-in writers while giving them significant additional income for zero additional labor. It would also expand the TAM to include the many writers that don’t want to charge for their work.
The second thing they would do is build a content recommendation system. A huge portion of the success of YouTube, Spotify, TikTok, and pretty much every other content aggregator is based on their ability to show the right content to the right user at the right time. This is the primary basis of their network effect. The more users they have, the more distribution they can give creators, the more creators they can attract. Without a network, Substack is forced to compete on CMS functionality (which can be copied) and pricing (a value-destroying race to the bottom).
The third thing our hypothetical YouTube PM would do, if they were bold, is introduce a Substack-wide bundle. This would help solve the trade-off between audience growth and monetization that is inherent in the standalone subscription model. It would allow Substack to act more like Netflix and Spotify, offering a coherent single value proposition to consumers, and perhaps enable them to do the kind of performance marketing that has propelled both of these companies to IPO.
Substack has said they’ll never do any of these things. But people don’t seem to believe them, I think because A) nobody trusts platforms these days, and B) it’s hard to imagine alternatives to the conventional aggregator playbook for accumulating power.
For example, here’s Ben Thompson from yesterday:
“What is interesting is that Apple may give Substack cover to change course. [...] Substack can (justifiably) say to its publishers that it is going to offer an all-up Substack bundle for in-app purchase because that is the only way it can offer in-app purchase, and that publishers should agree to be included as that is the only way they will be surfaced in what Substack hopes will be a new app that readers check regularly.”
This is straight up something Substack will never do. To his credit, Ben realized he got part of the story wrong and was fascinatingly introspective about it:
“I am so allergic to the prospect of being commoditized that I am always on the lookout for Substack doing exactly that to an area that I really care about, both on a conceptual level and on a practical level. To that end, I have been nervous about what Substack would do ever since they raised VC money, just because I am wary of the fundamental tension I see between backing up a big valuation versus doing what is best for individual publishers.”
The core dichotomy Ben presents is between the commercial interests of writers and VCs. You can squint at it and conflate the interests of writers with the Substack ideology, and their policies so far do happen to mostly line up with writers, but I think Substack’s deeper commitment is actually to changing the systems that human attention flows through. There will be a lot of ways in which this is better for writers, but in some ways they are willing to make trade-offs that might seem unexpected if you assumed their primary commitment was just doing whatever writers want.
Furthermore, it’s a mistake to assume that Substack isn’t committed to growth, too. Nobody raises money at a $640m valuation without that commitment.
So what can they do to navigate these conflicting commitments?
The first thing they’ve done is make sure as many readers as possible are aware that they’re using Substack. When your login information and credit card is stored, and the sites all look pretty similar and function the same way, it reduces the friction of signing up and paying for new newsletters. This is why from the beginning it’s been so important to Substack to limit the level of customization possible within their CMS.
This might seem pretty small and trivial of a thing to base a network effect on, but it might work. Substack has said readers are 2.5x more likely to become a paying subscriber to one Substack newsletter if they’re already a paying subscriber to another. I’m sure most of this is attributable to the fact that these readers are the type of people to buy paid newsletter subscriptions at all (regardless if on Substack or elsewhere) but I’m sure it also helps a bit that their credit card info is in there and they know and trust the system.
The second thing Substack is doing to build power within the constraints of their ideology is to create content discovery loops that are driven by people, rather than algorithms. This is why Substack lets writers feature other writers on their sites, and gives readers profiles where they can display which Substacks they are subscribed to. The centrality of this feature to their network effect explains why comments are so important—they are pretty much the only way someone might discover a fellow reader’s profile.
But perhaps the most important thing Substack can do to build more power is to create a new top-level destination for readers.
Right now when people read a Substack post, it’s usually because they first decided to check their email. Email is good for maintaining a direct relationship between readers and writers, but it kinda sucks as a place to read. When I’m checking my inbox I’m in a mode where I want to bat away everything as quickly as possible in order to get to inbox zero. I’m psychologically in a state where everything feels like a chore. Putting great writing there from my favorite authors is kind of jarring. It’s like putting a library in the DMV.
By launching reading apps for web and mobile, Substack is attempting to carve out a space in readers lives that is separate from administrivia and spam. A quieter, more sacred space.
The key to actually accomplishing this is push notifications.
When Substack launched their reader web app last year, I thought it was interesting but faced an uphill battle. It’s really hard in today’s age of addiction to get people to habitually come to a new URL. That’s why blogs died and became reincarnated as newsletters. Without push notifications, the new habit is too fragile and dies. I don’t have any real proof that Substack’s reader website didn’t work, but anecdotally amongst my friends and Twitter followers few people seem to use it:
The mobile app solves this, if they can get people to opt into push notifications. That’s why in the initial version of the app they made that a crucial part of the onboarding flow. Push notifications are a much more direct and clutter-free way to find out my favorite writers have published new work. They allow me to just dive in without worrying about that email from my boss that I need to reply to by the end of the day.
If Substack’s app becomes a place readers turn to directly and are more likely to engage with, it becomes that much more valuable of a place to be for writers. In the same way we turned to email to escape the noise of Facebook and Twitter, readers of the future might turn to the Substack app to escape the noise of email. This is the nature of things. Quiet places are great because they are quiet, which makes them crowded, which creates the opportunity to create a new quiet place.
But this is also where Substack’s ideology might run them into trouble.
What happens when readers subscribe to too many Substacks? What happens when the Substacks they subscribe to feel stale? The pressure is there and inevitable to create systems that sort, filter, and promote content.
In reality, I don’t think people actually want “full control” over what they read, because that’s too much work. What people are more likely to do is over-subscribe themselves, feel overwhelmed and stagnated in their content diet, and move onto a new platform if the old one doesn’t solve their problem for them. I don’t think most people are interested in painstakingly curating their feeds.
This creates a problem.
On the one hand, Substack has their ideological commitments. On the other hand, they have their immediate desire for growth. They may be tempted to get creative, in the same way I have heard young Mormons in Utah get creative in their pursuit of premarital sex within the bounds of their religion.
Often when people face a conflict between an immediate desire and a moral principle, they find a way to bend the moral principle to make it fit the immediate desire. Especially when the moral principle is uniquely restrictive as compared with others in society. A great example of this is how Jews in New York strung a fishing line around the island of Manhattan so that they could technically abide by the law prohibiting them from leaving their neighborhood on the Sabbath, the boundary of which was marked by a string.
How will Substack get around their stated promise to never develop algorithmic content recommendation engines, while still helping their writers reach new audiences? Well, if you open the Substack app, you are greeted by a “Discover” tab which recommends publications rather than posts. (Nice one!) It is unclear what algorith-ahem, method—is used to filter and sort which publications show up. Another fun example: you can connect your Twitter account to discover publications written by people you follow there—many of whom you presumably found originally with the help of Twitter’s algorithmic content engine.
Are these ideas violating the letter of the Substack law? No. But they do seem to me to flirt with the line, and I suspect this flirtation will only increase over time.
This to me is the key to understanding Substack: a delicate balance between growth-driven pragmatism and ideology-driven constraint. Both motivations are present, and they’re doing their best to harmonize them, even though there is some degree of inherent, inescapable conflict.
If you don’t understand this dynamic, it’s hard to understand why at times it might seem like Substack is doing something that’s the equivalent of hanging a string around Manhattan. If you aren’t religious, it might seem silly. But there are real principles at stake.
We can expect Substack to fight for them.
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I never thought about Substack and the ideology behind it in such a way. Thank you for this insightful piece of writing. It helped me to broaden my perspective.
Great post. I liked your personal story... and it makes me wonder if you've ever written down more of the story of your journey from substack to where you are now?
Also, I found myself wanting to reply during the part about notifications. I personally feel that push notifications are significantly worse than email at getting people to come into an app to read something potentially long and time consuming. I usually get push notifications while checking out at the grocery story or explaining to a kid why they can't have the thing they're begging for. And the problem with that is I swipe them away and they're gone forever. At least in email I can leave something unread if I want to come back to it (a dangerous and slippery slope if I want to retain inbox zero I know). I'll definitely go back to my inbox because I have to, but I haven't been able to make a habit of going to the substack app in the same way I have of burning 5 (ok 15) minutes on Tik Tok.