The Art of the Shill

M.G. Siegler
4 min readJul 11, 2021

It seems to me that something important has been lost in the debate about newsletters and the rise of the “creator economy” upending journalism. It has nothing to do with the format or the technology angle. It simply boils down to this: do you want to be a salesperson for yourself 24/7?

You might read that and think, well yes. Certainly if it means making more money or being more in control of your own destiny. And that’s all well and fair. But not everyone is in that boat. Take longtime New York Magazine art critic Jerry Saltz who turned down a lucrative offer from Substack recently and went public as to why. Per Insider:

“I think it’s fishy to always be barking to your readers to subscribe,” he said on Instagram on Thursday. “I think it is not my real work to write [for] ‘subscribers.’ My only work is to write for the reader.”

This resonates with me pretty deeply. And it’s not because I have some sort of moral attachment to or high-mindedness of journalism as a profession.¹ It’s because I don’t think I could operate in a world where all the incentives are around a constant need to self-promote.

This is the same reason why I have a hard time wrapping my head around ever writing a book (not that I have ideas bursting out of my brain either). I know what it takes to make a book successful. And we all see what authors must do in order to try to achieve such success. No judgement — well, slight judgement, but also some level of respect for the game — but I just don’t think I could bring myself to do it in a way it needs to be done.²

A book is an extreme version of shilling because the success or failure happens in such a relatively short amount of time. In order to make, say, a paid newsletter work, you would have to constantly be shilling for years. And again, nothing against this, it’s definitely part of the job because it’s a huge part of the model. I just honestly don’t know if I could bring myself to do it.

Even today, I often can’t bring myself to promote anything I’ve written. Not because I’m not proud of it — I often am, in some regard — but because I just view it as more in line with my own beliefs to have people find what I write (or not find what I write) naturally. Either they care enough to follow what I write via the mechanisms that automatically propagate the content (Medium, RSS, a stand-alone Twitter feed, etc), or they stumble upon it naturally elsewhere. I do at least somewhat believe in the meritocracy or Darwinian nature of content — that is, the best stuff will find you, one way or another. If you didn’t come upon something I wrote, you weren’t “meant” to, as it wasn’t good enough or in your wheelhouse, etc. Obviously, that’s a bit simplified and naive and even a bit unfair (to me and to you), but it’s how I tend to operate.

Don’t get me wrong, I’ll do the retweet here and there for something I spent time on, but I rarely share it out myself from my “major” channels. It drives my wife insane as she’s one of the people who relies on me sharing it myself to find it — she doesn’t subscribe to my RSS feed, it would seem, for shame. In all honesty, I write this now in part to help me think through if I should try to swallow my pride and do more such self-promotion.

But that’s all in the name of valuing people actually reading what I write, and less about trying to ask for people to pay for what I write. That’s another bridge that I thankfully don’t have to or anticipate crossing anytime soon. Again, not “thankfully” because I think it’s beneath me, but more so because I just don’t think I could do it on a regular basis. As you would need to, in order to be successful.

Saltz continues:

“I want to reach strangers; be loved and hated by strangers; talk about art to anyone any where any how,” he wrote. “I like being in my huge department store @Nymag where people find me who have no idea who I am or what I do or even thought about art before.”

This also resonates. I like the idea of reaching strangers with writing. Persuading new people, not just the loyal base. And that’s just a different model. Yes, offering “free” content on top of paywalled content gets around this somewhat. But probably never at the same scale you would get at say, New York Magazine.

Anyway, I just feel like Saltz’s stance and stand here brought up a point that’s been overlooked in this debate. Even if paid newsletters could work for everyone at scale, does everyone really want to do the work needed to be successful in that environment? The answer is pretty clearly ‘no”.

Photo by Adam Kring on Unsplash
Published on July 10, 2021 📆Written from San Francisco, CA 🗺Written on a 2020 13-inch M1 MacBook Air 💻Enjoying a New Belgium Sour IPA 🍻

¹ While I was a reporter for a number of years, I never went to journalism school and instead stumbled into it.

² I write this with the haunting feeling that these words will come back to me someday… PRE ORDER NOW.

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Writer turned investor turned investor who writes. General Partner at GV. I blog to think.