Should You Start a Newsletter? Maybe buddy

It cannot hurt!

Subscribe now

There’s an article in Buzzfeed this week called Paid Email Newsletters Are Proving Themselves As A Meaningful Revenue Generator For Writers and it features myself and a couple of others talking about how newsletters could maybe be a sustainable way to make a few bucks in a dying cancerous industry of doom. Some of the people in it are making a shit load of money what the fuck and some like me could maybe if things go well and I don’t fuck it up find my way toward a modest yearly media salary way under market price for someone of my experience level with an actual job. The system just works!

Part of it goes like this:

“The internet, originally, was supposed to be about, hey, if you could have 1,000 true fans, you could make a great living,” Jenkins said, citing an idea developed by the technology writer Kevin Kelly. “What Patreon and membership represent is the original concept of 1,000 true fans.”

Cash from these newsletters is enabling writers to be more selective about their work. Luke O’Neil, for instance, quit his freelance position with the Boston Globe after the paper removed one of his columns earlier this month that suggested service workers should tamper with Trump administration officials’ food. O’Neil figured he’d make up the lost Globe income via his Substack newsletter, Welcome to Hell World, which debuted in July 2018.

“I was making $350 or $400 week there, but I can make that up very easily by selling a few more subscriptions to my newsletter,” O’Neil said. His newsletter is on track to bring in approximately $50,000 this year, he told BuzzFeed News. And the food tampering controversy, for better or worse, brought more awareness along with it.

The Buzzfeed article is not dissimilar to an article I also was featured in a little while ago in the New York Times about newsletters or one from the Study Hall freelancers group and newsletter (which I can’t recommend joining enough) from before that. I have been very lucky to have gotten a good amount of attention for this newsletter in part because it is good and unique but also because I am Very Loud on Twitter.  Also it’s going to be a book soon from OR Books for which I signed a very low advance lol. Here are some cover ideas my friend Tyler Littwin mocked up that I quite like although I don’t know that we’re going to use them yet.

Subscribe now

The Study Hall one is behind a paywall and you should pay for it but it begins like this:

Luke O’Neil has been waiting two months to hear back from an editor at a “very famous” publication and he is growing increasingly frustrated. The piece, into which he estimates he poured several thousand dollars’ worth of work, will eventually — hopefully — earn him just a few hundred dollars. But not even that is for certain — his vanishing editor would have to return his emails first.

In the meantime, during those two months, O’Neil has published over a dozen free dispatches of his email newsletter Welcome to Hell World via the newsletter platform Substack. The entries cast a wide net, including personal musings on mental illness and addiction; interviews; and even reported pieces — a recent deep-dive on payday loan-like schemes spurred the Huffington Post to cut ties with a service that let freelancers get paid immediately in exchange for a cut of their earnings. Last week, he made the move to monetize the newsletter, as Substack lets writers charge for subscriptions.

For each of these entries, the only person who gives the green light for publication — the only person who assigns stories and edits them — is O’Neil himself. “I just don’t want to ask permission anymore. I want to write what I want to write when I want to write it,” says O’Neil, who has been a freelance writer for around 15 years. “I can’t describe how liberating it is to wake up with an idea in my brain, spend a few hours writing it, and see it rocketing around the internet by the end of the day. It’s just great.”

But that thrill of independence comes at a price. You might have to work for free before you can reap the financial benefits. And independent, to a certain extent, means solitary — no editorial team, no legal department. Substack might be a way to supplement your income, but it’s not a solution to the dying news business in and of itself. Is the solo newsletter business worth it?

As such and because I share Hell World on Twitter constantly (sorry buddy) lots of people message me asking if they should start a newsletter. I will answer some of those questions below but first here’s a thing I wrote for Substack talking about why I decided to work with them. It was mostly because the main guy Hamish was in Boston and asked to meet with me and I was like ah fuck I dunno I don’t want to do a newsletter that seems like a lot of work and I said I am too hungover to go meet you mate and he convinced me to anyway and I’m glad I did. We went to Brick + Mortar and had some nice cocktails and then I wasn’t hungover anymore until the next day which is called punting.

Ok here’s this part and then I’ll do a FAQ after unless I lose interest in this post in the next thirty seconds which is possible.

The first two things you should know about my particular deal is that I’m very lazy and not particularly smart so the idea of writing a newsletter would have never even occurred to me if the people from Substack hadn’t encouraged me to do it. Since then they’ve been very responsive to feedback and seem to care about their writers doing well which isn’t even the case at a lot of journalistic publications I’ve written for for many years who will cut your ass off at a moment’s notice without warning or explanation.

The third thing is that being a writer I have no brain for business so figuring out how to do the payment stuff would have just been too large a hurdle for me to ever deal with due to what I said earlier about being dumb and lazy. I suppose there are probably other services that one could use but I don’t think the main people from a much larger company are going to respond to your emails right away are they? Maybe they are who is to say?

One more thing about the idea of writing a newsletter in general is that for me anyway it’s as much about the things I don’t want to do as the things I can. I’m sick of having to ask for permission to write about stories that interest me. I’m sick of convincing an editor that a story will scale or do traffic. I’m sick of waiting for something to be published based on marketing whims or business concerns I am not privy to. I don’t want a timely news peg. I don’t want to fit into the agreed upon 800-1000 word window that is the norm for web writing. I don’t want someone to edit out my jokes or worse add new ones in you’d be very surprised how often that happens and then you’re just like whatever do whatever you want to the piece and give me my $350. I don’t want a billionaire to see me saying pee pee poo poo to human rights violators and decide it’s not deferential enough to the powerful and censor me.

The point is I want to write what I want to write whenever I want to and now you can too!

It’s like a podcast you can write basically. Will it last forever as the New Thing We’re Doing Now? Probably not. But this is how it goes and we’re all jumping from one melting ice floe to the next and if all goes well we might be able to do some good work along the way and we won’t fall in and drown.


Should I start a newsletter?



I can’t answer that for you. A lot of times people write to me asking for advice on how to be a freelancer and then I say well who do you want to write for and what kind of stories are you interested in writing and they don’t have an answer yet. You should have that figured out before you start in my opinion.

What should it be about?

Whatever your thing already is. Make it slightly different than everyone else’s. Make it your newsletter. It can literally be anything. There are no rules.

Will I make any money?

Probably not but there is literally no downside to trying and you might surprise yourself. If you can even get 50-100 people to pay you $5 a month that’s not nothing! That’s a decent chunk of your rent taken care of right? Not everyone on here is going to be a massive success but that’s true of every other thing ever. Like podcasts there will be a few stars and a vast middle class and a bunch of people who make no money. Capitalism is very good.

Do I need to be well known already?

You should probably have established at least some kind of modest audience for your work already before you start worrying about making money with a newsletter. If you’re just starting out as a writer you can certainly make one and try to build it slowly over time through elbow grease and other mythological terms.

It’s also a great way for writers with a couple of years under their belt and a few steady gigs to, if nothing else, alert your readers to when you’ve posted new work. It doesn’t have to be some weird experimental overly stylized and sentimental memoir reporting hybrid like whatever Hell World is.

Why not just post my articles on Facebook and Twitter?

Do that too but you obviously have seen what’s happened to Facebook and their refusal to actually show your posts to anyone. Twitter is a crapshoot because you never know who is going to be online or even see it when you share your article. You also never know when you might be banned from Twitter for some mysterious reason like I live in constant fear of. Once you’ve got your readers’ emails you control it and no one can take it away from you.

What is Joe Biden’s full name?

Joseph Robinette Biden Jr.

What the fuck?

I don’t know.

Are there fees involved?

Substack takes 10% of the cut and Stripe takes 3% for processing orders neither of which I am psyched about but what can you do. Substack treats me well and I would have made $0 if they didn’t convince me to do it in the first place. I don’t know what other places charge.

Why do you think newsletters are becoming A Thing lately?

I think people like supporting writers they like and admire which is very weird and surprising but not really because that is how it always used to be before Online. Obviously you are going to get a better product spending $5 a week on the New York Times or whatever it actually costs but I think people don’t like paying giant companies that much lately. I think they like paying people they trust. It’s like how people feel better about buying a record off BandCamp than they do subscribing to Spotify. The latter has infinitely more material but almost none of it goes to the people who actually did the labor. Or like how people don’t mind spending actual money on porn when it’s a personalized cam site or something as opposed to an aggregator. This newsletter isn’t unlike watching me get my red nude ass out to jerk off for twenty minutes now that I think of it.

How often should I send one out?

No idea. I could do one every day but I worry about overwhelming people’s inboxes and annoying them so I do like 3-4 a week.

Subscribe now