My Favorite Newsletters

One of the most appealing things about newsletters is the sense of intimacy they provide. When I write this, I feel like I’m writing directly to you, in a way that’s different from how I feel when I’m writing an essay or a short story. And I feel the same way—in reverse of course—when I read other people’s newsletters.

My other favorite thing about newsletters is that no matter how famous or talented the writer is, it still feels like they’re more or less doing the same thing I’m doing. Somehow, when I read a book, its existence as a physical object makes it feel categorically different from the writing I do. I don’t feel like I could just put down the book I’m reading and go write my own. I could write my own manuscript, sure, but it wouldn’t be a book.

Of course, I know that feeling is an illusion. What separates me and the writers of “actual books” is their talent and persistence, not their ability to navigate the publishing process. But the appealing evenness to the newsletter playing field still feels like a contrast.

It’s like that Andy Warhol quote about Coke:

The President drinks Coca-Cola, Liz Taylor drinks Coca-Cola, and just think, you can drink Coca-Cola, too. A Coke is a Coke and no amount of money can get you a better coke than the one the bum on the corner is drinking.

Well, the famous, the not-so-famous, and the bums on the street all use the same Substack too.

With that in mind, here’s a look at some of my favorite newsletters.

Money Stuff

My current favorite (although the list changes constantly), and probably the most well-known newsletter on this list, Money Stuff is a daily look at goings-on in the world of finance, and a stellar example of how a good writer can make almost any subject interesting. It’s also the funniest newsletter I read, which is pretty remarkable given that much of it is devoted to explaining complex financial concepts like derivatives and variable interest entities.

The true genius of Money Stuff is that it perfectly combines two distinct, but not necessarily contradictory, viewpoints:

  1. Finance is important and necessary, and the over-simplified critiques of it you hear (mostly) from the political left are wrong; and

  2. Finance is inherently absurd and fundamentally ridiculous at a deep, philosophical level, and anyone who takes it too seriously is an idiot.

Where to start: really you can’t go wrong with any of them, but this one about AMC and Elon Musk is a classic.

Maybe Baby

Many of the newsletters I read regularly can most succinctly be described as “young women writing about their feelings,” and Maybe Baby is far and away the best of that genre. It’s hard to describe beyond that—in fact, its tagline is “a newsletter about hard-to-describe feelings”—but it’s excellent.

My favorite thing about this newsletter is the author’s ability to combine personal thoughts and feelings with outside information and references, which makes the writing feel intimate but not solipsistic (something I’m still working on).

Where to start: Sex in Hindsight

Stephen Elliott’s Self Help Newsletter

Until 2018, Stephen Elliott was best known as the writer of The Adderall Diaries and a few other mildly well-received books. Now he’s probably better known as the guy who sued the creator of the Shitty Media Men list for libel, and who rails against “cancel culture” on Twitter. However, his newsletter—which is completely unrelated to the above topics—is excellent.

It’s ostensibly the working draft of a self-help book about how to grow wealth through real estate, but in reality, almost every issue goes completely off the rails and touches on the author’s wayward youth, romantic troubles, money issues, past drug problems, etc. It’s a great example of how sometimes following unexpected digressions can result in more interesting writing than staying on track. And you actually do learn a bit about real estate too.

Where to start: How to Buy a House

Hot Singles NYC

Hot Singles is a newsletter of personal ads: one person featured per issue, twice a week. If you’re interested in one of the featured people, you write in with a photo and a few lines about yourself and, if they’re interested too, the author connects you. Such a simple concept, but somehow no one had thought of it until now. And compelling: Hot Singles has really started to blow up lately (and not just because I was featured in it a few months ago).

I think things like Hot Singles are the future of online dating. As people get more and more tired with apps, Hot Singles offers a more personal and quirky feel, while still letting you meet people over the internet. Hot Singles dates are extra fun because you feel like you’re doing something cool and unusual right off the bat—just like Tinder dates felt in the very early days.

The other genius of Hot Singles is that unlike dating apps, its target audience isn’t limited to single people. I know many partnered people who read it just for fun, or so they can forward issues to their single friends.

I include Hot Singles here not just because I think it’s great, but also because I like that it’s a newsletter whose appeal isn’t really about the writing. I expect many other non-writing-focused innovations to be created on top of the newsletter format in the coming years.

Where to start: my feature, of course

Yours in eagerness to hear about any of your favorite newsletters,

Max