People Who Shaped My Intellectual Growth

I came across Tracy-Gregory Gilmore’s list of people who have influenced him, and I found the idea really charming. Exposure to a few different people’s ideas has been incalculably valuable to me, and I want to publicly thank them in the same way Gilmore did.

These are people I consider “remote mentors” (a concept I wrote about in August, 2016). Two writers in particular have profoundly shaped how I see the world: Scott Alexander of Slate Star Codex and Ben Thompson of Stratechery. Their names are repeated on the list below, but they deserve special recognition.

In chronological order:

  • Vladimir Nabokov, who penned the infamous novel Lolita, is my favorite author. That book in particular turned me onto postmodernism and moral complexity.
  • Ben Thompson of Stratechery is a business analyst who writes about the tech industry. Reading his articles got me interested in business and economics, and I learned a lot from his commentary on incentives and the structure(s) of markets.
  • Scott Alexander of Slate Star Codex is… well, professionally he’s a psychiatrist, but online he’s sort of a cultural philosopher. His essays on identity, community, and politics have been very illuminating. Everything is virtue-signaling!
  • Venkatesh Rao, creator of Ribbonfarm and Breaking Smart, is a writer in a similar vein to Scott Alexander of Slate Star Codex. The label “cultural philosopher” once again feels like it fits. His area of expertise is breaking people’s mental models and then helping reconstruct them.
  • Meredith Patterson and Alice Maz are both programmers who wrote essays that helped me become more empathetic. Patterson wrote “Okay, Feminism, It’s Time We Had a Talk About Empathy” and “When Nerds Collide”. Maz wrote “Splain it to Me”.
  • Adam Elkus and David Auerbach are two polymath scholars who incisively understand the meta-politics of the cyber age (which is only just dawning, I might add).
  • Lou Keep’s Uruk Series is a phenomenal tool for understanding modern discontent and the failure cases of social control systems. Start with the essay on Seeing Like a State and then skip to the essay on witch doctors.

Last updated 8/13/2018.

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The Economics of Writing Online

“Failures in Self-Publishing” just went up on The Digital Reader, so now feels like a good time to post an elaboration on how to actually make money by writing online. (Scroll to the bottom for the other reason I’m putting this up now.)


As a person with many opinions but only moderate hustle, I’ve ended up writing for free a lot. Not just writing for free, but being published for free. I’m okay with that — I have a day job. I also understand supply and demand: personal essays aren’t scarce, so they’re not particularly remunerative. When I have been paid, the check was usually a pittance that amounted to minimum wage (and that’s before self-employment taxes!). I resented this when I was freelancing professionally, but now that I do it as a hobby, I shrug and tell myself, “This is what the market dictates.”

Price, after all — especially average price — is a number synthesized from the desires of the various players in a commercial endeavor. Customers want to pay less and merchants want to charge more. They agree somewhere in the middle, depending on which side has more leverage. Who is willing to walk away? Who is anxious to make a deal? If customers have many other merchants to choose from, the price is low. If merchants face a deluge of eager buyers, the price is high (*cough* iPhone 6s *cough*).

It’s not a new observation that this problem plagues digital media. Readers can easily jump from website to website without sacrificing anything. Publishers, on the other hand, need as many eyeballs as possible and therefore must be flashy and attractive, as well as careful not to alienate their audiences. Most website-owners are stuck in this game, straining to make a couple of advertising cents per reader. You can’t convince people to pay money for a subscription unless you offer unique, high-quality content, which is extremely hard to produce.

Writers have the same relationship to publishers that publishers do to readers — there are plenty of other fish in the sea, so unless you offer something very compelling that can’t be obtained elsewhere, you’re probably shit outta luck. Don’t get me wrong — there is money to be made in writing to entertain a general audience, but not enough for the amount of people who are trying to make a living at it. Incumbent media outlets and winning internet-age startups like Vox Media have flooded this territory.

There are several ways to deal with the evident economics of writing online. One is to be a typical professional from nine to five — in fact, being a smart and prolific blogger will get you a better job and a better salary than you would earn otherwise. It will also bring you surprising opportunities — I landed a copy-writing gig via Twitter recently. Good writing demonstrates key communication and analytical abilities, which are important to every kind of skilled labor. Does having a day job mean that you can’t devote most of your time and intellectual energy to writing? Yes. Such is reality. The other options are to 1) work for peanuts and write thousands of words per day or 2) develop expertise in a particular niche where there is a market for quality.

In closing, I would like to note that I owe a majority of the ideas in this piece to Ben Thompson of Stratechery. I highly recommend his blog and newsletter.


Additional note: I originally wrote this in late September and it was published on Samantha Bielefeld’s blog. I asked her to take it down because of this drama. Summaries of the situation can be found on Building Twenty and Analog Senses. I resent being duped and exploited, and I don’t want my name associated with someone who is essentially a fraudster. If you want to explore the whole brouhaha, you can read everything I’ve said about SB on Twitter (scroll down to September 25th and read upward) as an introduction.

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Self-Referencing To Build Meaning Instead Of SEO

points on a map, linked together
Photo by Cali4beach.

Ben Thompson’s tech analysis is recursive, which is one of the various reasons to appreciate what he does. Practically speaking, I mean that Thompson constantly references his past work, linking to previous pieces in every new one. He builds new arguments from old ones, or rather extends his past assertions, instead of constructing each article entirely from scratch. Smart approach, whether it’s conscious or not.

information linked together
Illustration by Elco van Staveren.

Thompson’s recursive writing provides a sense of timeline, grounding each new post in a fuller body of work. This gives the reader a sense of ever-mounting value, and provides an intellectual narrative as Thompson’s own positions evolve.

So much of the content on the internet feels random, contextless. Often, standalone pieces don’t actually manage to stand alone. Thompson defies this trend, and convinces drive-by readers to become dedicated subscribers, by tying everything he publishes to everything else he’s published.

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Niche Websites Aren’t Trying Hard Enough To Make Money

Blinded by Journalism
Photo by Ahmad Hammoud.

How to fund online journalism? For the most part, the conversation has focused on advertising. Hampton Stephens, founder of the self-sustaining World Politics Review, finds this puzzling. He cautions websites backed by venture capital, like BuzzFeed and Vox:

“The lesson that most media startups seem to have taken from the evisceration of advertising-supported journalism over the past two decades is that more innovation is needed… in advertising. […] To ensure the kind of ‘accountability journalism’ that is critical for any democracy to flourish, well-funded new media players must experiment with models other than advertising.”

Apparently everyone wants to copy the free metropolitan weeklies stuffed with “medical” marijuana enthusiasts. (No offense meant, East Bay Express.) A few high-end legacy newspapers—and premium newcomers like Stephens’ World Politics Review—have made subscription systems work, but only up to a point. The signups are slowing down. So… that’s it. Alternatives are strangely infrequently discussed, despite the occasional hat tip to research divisions.

Here’s the problem: Advertising works reasonably well when a website is deluged by traffic, but what about smaller operations? Are niche editorial websites doomed, or are they thriving? The general trend can be difficult to track, but journalistic endeavors of all sizes are trying to guess how they will be funded in a mobile-first world populated by Millennials who balk at paying for information.

Continue reading “Niche Websites Aren’t Trying Hard Enough To Make Money”

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Who Pays Writers? Apparently Not RSS Users

retro 1920s blogger
Mike Licht has made and posted a million of these for some reason.

Necessary context for the upcoming screenshot: Ben Thompson is a popular tech blogger who offers an exclusive email newsletter for $10 per month. Recently some kind of bug inserted a couple of subscriber-only posts into the blog’s public RSS feed. Here’s a brief Twitter exchange between subscriber Blaine Wilson and Thompson:

RSS readers don't pay for content
Wilson: “Hey Ben, I’m interested to know if the RSS leak lead to any sort of upside in update subscriptions as people got a taste.” Thompson: “I’ve learned that RSS users aren’t really the types to pay for content :)”

I don’t have any substantive commentary on Thompson’s observation, but I think it’s worth noting. (Obviously, considering that here I am noting it.)

classic art blogger photoshop
Also by Mike Licht. Thanks, dude.

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