Matt Yglesias and the secret of blogging

How to be a successful content entrepreneur

What is the secret to a successful career as a blogger/newsletter author/content creator? No one ever asks me this, because my career is not successful, but if they did I would tell them to read last week’s Washington Post profile of Matt Yglesias, the former Slate and Vox columnist turned Substack entrepreneur.

Yglesias needs no introduction, because, as the profile soberingly points out, he’s now been blogging about politics from a moderate-liberal perspective for more than two decades, across multiple publications, content-management systems, and distribution mechanisms; it is hard to imagine a person even slightly engaged with U.S. politics online never once encountering Yglesias’s writing or persona, even, and maybe especially, in the context of people complaining about him. He is often (and correctly) criticized for the many times he’s been (loudly, glibly) wrong over the years, but he is undeniably one of our most successful and influential bloggers, and must be, at this point, recognized as an exemplar of the form, for better and for worse.

But what is the secret to his success? The Post profile, or at least some of its sources, vaguely suggest that Yglesias has deliberately triangulated his position and persona over the years, in part to attract and serve a specific audience of liberal moderates and D.C. elites, but also maximize his own visibility by making lots of people on Twitter angry at him. (“He’s basically a panhandler who’s driving outrage on Twitter, and benefits from how he engages with the performance of discourse,” says the student-debt activist Melissa Byrne.) I don’t know Yglesias; it seems possible that he is reverse-engineering political positions for maximum distance traveled in quote-tweet dunks, whether intentionally or through the follow-the-attention sixth sense that all career posters eventually develop. But I think he actually reveals the real secret to his blogging -- the foundation of his success -- much more directly and early on in the piece:

“It’s the best time there’s ever been to be somebody who can write something coherent quickly,” Yglesias says, over coffee. “I find it relaxing to work. I put things out. People yell at me. I will write again the next day.”

“I will write again the next day”: As the profile reminds us, Yglesias has been writing posts for 21 years, day in, day out, regardless of political or economic or emotional conditions. “For two decades, Yglesias has been boring,” the profile’s author Dan Zak writes, riffing on the title of his subject’s Substack, “Slow Boring.” “A million boring posts, across many platforms, into many hard boards.”

I write from time to time in this newsletter about the hard-won lessons I have learned over the decades I have spent creating and consuming content on the internet -- lessons like “don’t go to journalism school” and “don’t be a journalist” and “don’t write mean things about rich people or even professionally associate yourself with publications that do because it will be hard for you to find a real job later when you have a toddler.” But the key lesson, the thing I would impart to any aspiring bloggers, content creators, or newsletter proprietors, is that the cornerstone of internet success is not intelligence or novelty or outrageousness or even speed, but regularity.¹ There are all kinds of things you can do to develop and retain an audience -- break news, loudly talk about your own independence, make your Twitter avatar a photo of a cute girl -- but the single most important thing you can do is post regularly and never stop.

Granted, “work hard and keep doing the thing you’re doing” is probably above-replacement advice for any kind of entrepreneurial activity. But it’s particularly true for online content creation. As Yglesias suggests, the internet and feed-based social platforms have constructed an insatiable demand for content,² so if you can produce content mechanically, without requiring expensive resources (such as time, wit, or subject-specific knowledge), you’re in an excellent position to take advantage. But most importantly, this demand is so insatiable that there is currently no real economic punishment for content overproduction. You will almost never lose money, followers, attention, or reach simply from posting too much.

It’s this last part that is often most difficult for writers to accept. I think many people who write on the internet have a risk/reward model around posting: Everyone knows that there is high upside reward to posting (i.e., you might go viral and be able to sell galaxy lights under your tweet), but everyone also believes that posting carries with it risk. Setting aside the risk of “cancellation” or “embarrassment” (more on this later), in a business sense the understandable assumption is that if you post more blog posts/tweets/newsletters/whatever, you will also necessarily be lowering the quality of your work. Something you take a few days on -- in order to research, report, edit, or even just think through in a rigorous way -- will naturally be better than something you crank out in a couple hours. Many people -- especially writers, since we have a lot invested in the idea that what matters most with our work is its aesthetic brilliance or intellectual novelty, and not with the kind of basic fact that it exists on a page somewhere to help someone pass the time -- instinctively believe that if you bombard your audience with half-assed crud, you’ll lose whatever audience you’ve built up, and never get the kind of reach you’re looking for. Before they post, therefore, many writers mentally calculate: Is this post “good enough,” or does it dilute the overall quality of my work, alienate my audience, etc.?

But the Yglesias profile’s very existence reminds us of an important rule of thumb for navigating the content economy in the 21st century: Under the present regime, there is no real downside risk to posting. You might lose a small handful of subscribers or followers if you overwhelm their inbox, or write an egregiously bad post -- but on balance you will never lose as many readers from “posting all the time” as you will gain new ones. I’m not even talking here about controversial or outrageous writing, though its success is a reflection of this basic principle. Even the most anodyne, mediocre writing fulfills the requirement of regularity. (What is the “Wayne Gretzky” quote? “You miss 100 percent of the audience conversion opportunities you don’t take”?)

This understanding of publishing, which suggests that rough-and-ready, quasi-automatic writing done on a regular, frequent schedule is ultimately more financially sustainable than refined and thoughtful writing published when necessary and appropriate, can seem counterintuitive, if not unbelievably cynical and depressing.³ No one wants to pick “quantity” over “quality” when it comes to their own work, and most readers, given the explicit choice, would say they prefer one great newsletter a week over five “coherent”⁴ ones.⁵ But the fact is that as much as people might complain that a given newsletter appears too frequently for them to read it, or that a person's byline is ubiquitous, in practice, the vast majority will not unsubscribe or mute or ignore. Meanwhile, every new post brings with it the possibility of new readers and an expanded audience. The more you write, the better. What do the top text-based content-creation entrepreneurs of our time have in common? Logorrhea.

There is one more thing to say about this, I think, which has to do with the part of the Yglesias quote where he says “people get mad at me.” When I write that posting has no real downside risk, I can imagine many writers disagreeing: If you post, people might get mad at you! Or maybe you will say something wrong, or embarrassing, or be revealed as a fraud. The downside risk to posting, I think most people believe deep down, is not “losing followers” but “feeling shame.”

It’s easy to see why writers reared in the hothouse reputational marketplace of Twitter are desperate to avoid the shame of negative attention. But what I think Yglesias suggests, and what his career bears out, is that it doesn’t really matter. In aggregate, over a shorter period of time than you imagine, people forget, or move on, or don’t really care. It is extremely rare to see writers bear any kind of significant career consequences for being wrong, let alone for being cringe. Feeling shame that prevents you from doing or saying inappropriate things is maybe a useful way to navigate complex moral-social arrangements, but fearing shame that prevents you from adhering to the first commandment of blogging (“post frequently and regularly”) is counterproductive.⁶ As Yglesias says, it's the best time there’s ever been to be somebody who can write something coherent quickly. Put things out. Let people yell at you. Write again the next day.

1. I say “regularity” instead of “consistency” because “consistency” sort of implies quality to me, and reliable quality is of only passing importance compared to reliable production. “Regularity,” on the other hand, reminds me, appropriately, of bowel movements.

2. Feels like we should be explicit that this apparent demand for content is not some “natural” outcome but is encouraged and cultivated by the business incentives of advertising marketplaces built on some very shaky foundations and dubious assumptions. Nevertheless, my livelihood depends on it. LOL.

3. If you are looking for an optimistic way to look at it, consider it “freeing”: Stop worrying about whether something is “good enough” and just keep on posting!

4. Probably best to read “coherent” as pertaining to the syntactical/grammatical level here -- I am not sure that logical/argumentative coherency is actually very important to successful bloggers. You will notice that frequent posters like Yglesias (myself included) often take long, convoluted prose journeys to relatively simple or noncontroversial points, or even to no particular destination at all; I am not positive those posts are “coherent” in the broadest sense, but they are legible and usually more pleasurable to read than what GPT3 can currently produce.

5. Indeed, over the last decade or so, many, many publications have pitched themselves as the quality-over-quantity shop, hypothetically posing this exact choice to readers, with varying levels of success at actually following through on the pitch. Including, I should say, the one you are reading right now. Just to give some vaguely empirical shape to the theory here, I can say that periods where I send out 3+ newsletters a week, like in the midst of Twitter/FTX madness last November, instead of the promised two, have seen significantly faster paid-subscriber growth; in fallow periods, like last July/August, where I was posting once a week at most, I was barely making up for churn. I don’t doubt that there are outlets that can carve out a more generous balance between volume and care. But practically speaking, in my experience, by every metric except “how proud you are of your work,” producing a lot of newsletters (or whatever kind of content) is a more sustainable strategy than producing fewer, but better.

6. I used to think that “shamelessness” was a prerequisite to online success, but I increasingly think that successful online writers’ relationship to shame actually falls in a bimodal distribution: There are many big-time bloggers who post on relentlessly, impervious to embarrassment or shame (you can supply your own examples); but there are also a number of successful, influential bloggers who are the opposite, who feel shame so deeply and thoroughly it actually compels them to post more, pushing them to respond to any kind of emotional stimulus at all with endless (if still always inadequate) self-examination. I’m thinking here, e.g., of American Conservative blogger Rod Dreher, whose magnificent oeuvre reached new heights in December when he produced an astonishing post about how his dad was in the Klan that veered from brutally honest reckoning with familial sin to accusing the Freemasons of possessing his father with a demon.