A couple weeks ago, this tweet stood out to me:
I think one thing Paul Graham underweights when he advises people on how to write is the fact that sometimes you need cleverness to earn status with the reader. Paul has earned status by making a ton of money. Him writing simply is like Zuckerberg in a gray T-shirt. A gray…
— Cairo Smith (@cairoasmith) September 2, 2026
Is Paul Graham such a successful writer because of special writing techniques, or is his success more attributable to the size of his brand and his wealth, creating a halo effect? It’s likely both, but I think the brand aspect is given much less consideration than it deserves, as the above tweet alludes to.
His advice, in posts such as “Write simply” (2021), “Writes and Write-Nots” (2024), “Writing, Briefly,” and “Good Writing” (2025), circles around the same theme of the importance of “writing simply.” Same for the late Dilbert cartoonist and blogger Scott Adams, in a popular now-archived blog post, “The Day You Became a Better Writer,” who similarly advised economy and simplicity of prose:
But a lot of people write simply or clearly, or at least try to; how come so few are as successful as Scott Adams or Paul Graham? The sine qua non or essence of Twitter is simple , direct writing, yet we clearly see a hierarchy of follower counts and success. Moreover, how come so many writers who eschew such advice, by writing long, difficult content, are so successful, notably Curtis Yarvin in the context of blogging, or say, literary fiction–an entire genre unto itself in which elaborate prose is the expectation?
As someone who reads and notices a lot, I have observed that a good chunk, if not all, of conventional or ‘commonsense’ writing advice is wrong or obsolete, and/or hopelessly confounded . Maybe it worked in the past, but not anymore. Or there is more nuance. There is obvious survivorship bias: what about the many unnamed individuals who followed this same advice and failed? There is also plenty of bad writing which falls into this category, like LinkedIn slop or “AI slop.” It’s not as if LinkedIn writing is hard to read or is conceptually difficult, yet it has an unmistakable badness.
It’s evident “write clearly” or “write simply” isn’t good enough. From my observations, your options are: you either have to be really successful at a non-writing endeavor (e.g. a wealthy VC), or extremely talented at the act of writing (e.g., Moldbug, Scott Alexander, etc., who became hugely successful organically without a brand or extreme levels of wealth). There isn’t any way around this.
As discussed in the post “Why Academic Writing Works” the issue or disconnect has to do with revealed vs. stated preferences. People may say they like simple, easy writing, but over and over, the most popular and successful writers and widely shared articles use a more academic and sophisticated writing tone, contrary to this commonsense writing advice or stated preference for simpler writing.
I suspect this is because academic-style writing conveys invaluable credibility, which makes other smart, credentialed people more inclined to share it, so it’s more likely to go viral, even if the majority of readers never finish it. Because readers do not want their time wasted, they will perceive the longer, more difficult style of writing as more credible and substantive, even if they don’t actually read the piece in its entirety. When people complain Moldbug is too verbose, I’m like, “Yeah, that’s the point.” Otherwise, his writing would be ignored in the sea of “simple” writing that dominates.
All the the most successful bloggers I follow write this way; they are not writing at a 6th-grade reading level, but for a well-educated audience, and judging by Substack subscriber revenue and engagement (e.g. comments and shares), evidently it does work . I trust the marketplace much more so than overrated experts , whose success is just survivorship bias anyway, who insist “simple is better;” the marketplace clearly thinks otherwise. The likes of Curtis Yarvin, Freddie DeBoar, and Sam Kriss, among many others, found huge success doing the opposite of those guides or advice, writing dense, difficult prose, using a varied and sophisticated vocabulary, and weaving many ideas into a single post.
Of course, this may also be survivorship bias, but consider the following crucial observation: all of those writers found huge success by the merits of their writing alone, without much branding, self-promotion, or ‘industry connections’. The writing was so good, people felt compelled to read, subscribe, and share it on that alone. By contrast, with Scott Adams and Paul Graham, they were already hugely successful and had big brands at non-writing endeavors, and then this success spilled into writing.
There is the confusion of cause and effect; it’s not so much that simple writing leads to success at writing, but if you have a large brand already, any style will work, owing to having a brand. If Taylor Swift wrote a book, it would likely be a best-seller, just owing to the fact she is a major celebrity, not because of any particular writing style.
This is a problem endemic to all advice: survivorship bias and confounders. It’s impossible to know the denominator–that is–the number of people who applied said advice. This is really common in fitness/coaching. A coach will have many clients, but only a few will achieve good “before-and-after results.” This is used as “evidence” of the coaching program being effective, ignoring all the failures.
Unlike survivorship bias, at least the confounders can be controlled for and are knowable. In the case of Scott Adams and Paul Graham , the confounders are non-writing success begetting writing success. Mr Graham’s writing success tracks his success as a successful VC. Same for Mr. Adams as an influential political pundit and successful cartoonist. Therefore, to minimize confounders, I posit the best or most actionable writing advice is from successful writers who became successful from their writing alone, without a concurrent non-writing career.
By comparison, these “incidental writers” hone in on the same “simple style” and advice, which worked for them largely owning to their non-writing endeavors. But it’s hit or miss, mostly miss, when others apply it.