Tedium - Newsletter, Untethered ✍️

Today in Tedium: Recently, I got an opportunity to write something, which is most assuredly nothing new to me, but it was actually a pretty interesting experience. Basically, this website called Pairagraph has been bringing together smart people in related fields—think an economist and a venture capitalist, or a philosopher and an ethicist—and has them discuss some kind of hot topic. Basically, it’s super nerdy, started by a pair of Duke graduates, and I was there chatting about a topic I know a lot about—newsletters. Along with my cowriter, Elizabeth Spiers (who runs the political consulting firm The Insurrection and was the founding editor of Gawker), we discussed the good and bad of the current self-publishing rush and whether it made sense for writers. Our timing was nearly perfect—a mere two weeks after we wrote our joint essay, Substack had a huge controversy, and is now facing a backlash. Writers are thinking of jumping ship and looking for ideas for what to do next. I’ve been doing this without a net for a while, and I have a few thoughts on how it can be done. With that in mind, today’s Tedium is a guide to self-publishing over email, and how the heck to do it right. No net needed here. — Ernie @ Tedium

Today’s Tedium is sponsored, fittingly, by another newsletter, Quantum of Solazzo. More below:

Floating in the middle of nowhere is hard. At some point you might need a platform. But don’t let that platform leave you stranded. (Josh Withers/Unsplash)

Before we get started, a few thoughts about platform exposure

For those not familiar with the debate happening in the newsletter space right now, a lot of users are concerned about the growing interest of large tech companies in newsletters—Facebook announced a planned offering this week, which I’m sure John Tesh will love—and others are concerned about the way Substack is pre-paying some famous writers to join the platform without a) telling the public who got the money, innocuous or not; and b) admitting that the pre-payment amounts to editorial influence on the platform. (Related to this, and playing a factor in some people wanting to leave Substack, is the concern that Substack is paying writers with controversial views.)

In a pretty representative example of the response to the issue, Annalee Newitz, the founding editor-in-chief of the Gawker Media blog io9, went so far as to call Substack’s business model a “scam.”

“Sure, they could call their newsletter by any name they wanted, but Substack was paying them to do it,” she wrote. “And yet Substack was pretending that its successful newsletters were all bootstrapped. That sounded like shenanigans to me.”

In the past, I’ve made something of a stink about the fact that I don’t publish Tedium on platforms like Substack. They reached out to me right when they were starting it up, and asked me to join, and in a friendly way, I turned them down. (My basic business strategy: Say no more than you say yes.) I liked what they were doing for the newsletter space at that early time, but I had been down the road of leaning on a platform before and I had not great opinions about it. Plus, no custom templates!

But to be clear, dealing with platforms is a reality of the modern internet. For example, it’s well-known that I frequently syndicate with Motherboard, which is a publication of Vice, a large editorial platform. And I’ve sometimes posted my old content on Medium. Finally, I made the explicit decision to start a smaller newsletter on Revue, a platform bought by Twitter just two months ago. And I post on Twitter, too!

I’ve said all this stuff about platforms being problematic over the years. What gives?

The way I think about it is this: If any of these platforms shut down tomorrow, which one would I be most upset about losing? Clearly, the newsletter that you’re reading. If the server went on fire and I lost all of my content, I might be more than a little sad.

So put work you care about less—work for hire, short-form editorial, dumb jokes, random experiments—on platforms you don’t control, where the risk of failure is a distinct possibility. Leverage the resources of what else is out there. But when you’re working on the stuff that does really matter to you, put it in a place you have ownership of. Put it on your website. Send the newsletter using tools you run or manage—and be willing to pay for that right.

Think about this in terms of attack surface. When all those publishers bet big on Facebook a few years ago in the so-called “pivot to video,” they were ultimately burned because Facebook wasn’t truly interested in helping publishers. If those publishers made small bets, it wouldn’t have been a problem—but they bet really big, and that left them majorly exposed.

In many ways, self-hosting is the only realistic way to know that your motivations for your creative work are being fully respected in a way that matches your values. The problem is, to gain that respect, you have to shoulder more of the risk.

You may in fact need to spend time in a code editor to run a newsletter self-hosted. But you don’t necessarily have to. (Christopher Gower/Unsplash)

A few of the many tools you can use to build your own newsletter without the help of platforms

In a lot of ways, the tools are the most important part of this, and will require a degree of learning as you figure out the right balance. So with that in mind, I’m going to lay out a few examples of technical stack strategies that could come in handy for newsletter creators looking to roll their own. (If you want a different take on this, Fast Company contributor and fellow newsletter author Jared Newman also wrote something about this topic this week. Jinx!) Here goes:

One benefit of Craft CMS is the endless array of plugins. Some of those plugins help you build a newsletter.

Craft CMS (free/self-hosted for small sites, $299 for larger ones): This is the approach I personally use, and I came to it basically out of a desire to have more flexibility in how I presented my content, and to follow through on my longstanding recommendation that content management systems should be used for newsletters. Like well-known monolithic CMSes such as Drupal, it is built in a way that you can architecture out your own database, but it is very flexible in how you can do it. In my case, I was able to build out a system that parses content in Markdown (my writing format of choice), that has its own built in ad architecture that I can plug into articles however I want, and that includes a view in the theme that spits out a full article in an email template I designed with the markup language MJML. (I could send the emails through Craft directly with a plugin, but I prefer shipping off the raw code to EmailOctopus for customer support reasons.) I like coding my own layouts, so I do it this way. The one headache that you may run into is initial setup, but there are a number of Craft-specific hosts out there, like Fortrabbit, that can make it easier. This is, admittedly, work to build—when I moved my site to Craft it was a two-month project that required lots of manual input—but I’m a designer at heart and stuff like that makes me happy. Everything is ultimately just what I want it to be and I’m happy with what I have.

Ghost (free/self-hosted, paid hosting starting at $9/mo): I used to use Ghost to send Tedium much earlier in its history, and found the tool useful for writing, but I moved away from it for a few reasons, in part because it was not really built for hosting newsletters and I hacked it to work that way. Since I did that, however, the makers of the open-source CMS added a ton of membership capabilities as well as the ability to natively send newsletters. Just this week, it launched a significant update to the platform that makes the membership and newsletter features more central to its setup. My personal feeling on Ghost is that it’s probably the simplest option for roll-your-own out there right now. It’s basically turnkey. It is not built to be heavily extended like Craft is (for one thing, custom-building your own newsletter template is not a feature of the platform at this time), and if you want to customize it beyond theming it may not be for you. But most people don’t want that, so this is a good one.

Sendy ($69 one-time fee, plus costs of upgrade): While Sendy admittedly doesn’t look quite as snazzy as Ghost does out of the gate, it provides an incredibly useful service for people who regularly send emails—a self-hosted way to send bulk messages without having to pay hundreds of dollars a month to providers like MailChimp. One benefit of this tool is that it’s been around a while and integrates with a lot of external services, and maturity is often a good thing when it comes to something as complex as an email sender.

Newsletter Glue, a plugin designed for WordPress.

WordPress plus plugins (mostly free, plus hosting costs and costs of plugins): WordPress is the largest content management system, and many writers and editors likely use tools like it. It can be hosted on a toaster if you’re into that kinda thing. There are a few ways to send emails via a CMS—fellow newsletter traveler Charlie Meyerson of Chicago Public Square, who is a Blogger user, leans on an RSS feed-driven send automated through MailChimp—but one relatively recent option, Newsletter Glue, takes advantage of recent upgrades to the WordPress editor to offer a simple, clean experience for shooting out messages to the world. (It also integrates with Sendy, allowing for a clean sending experience with minimal platform exposure.) And WordPress creators Automattic themselves recently got into the newsletter plugin game! And if you need members-only gating on your offering, a good way to get that is Memberful, though lots of plugins exist there, too.

Gmass (starting at $12.95/mo): But what if you don’t want to deal with hosting at all and just want to send your newsletter in bulk to lots of people? You could always purchase access to a tool like Gmass, which sends bulk emails through the already familiar Gmail interface. This is a strategy generally used for sending cold-call-like emails, but nothing would stop you from sending a newsletter through it, really.

Totally open-source options. (the only cost is your time) If you want a totally free/open-source version of the general concept of Sendy, there are a few options that allow you to do this. Among them: The nonprofit FreeCodeCamp developed Mail for Good a few years ago, the PHP-based email tool SendPortal adds a layer of polish, and the Node.js-based Mailtrain offers another flexible option for those interested. The benefit of these strategies is that you can run these locally on your own machine if you know enough about the command line. (I literally installed SendPortal on my machine in like five minutes, as I was writing this, with the help of Laravel Valet.) And if you’re feeling really bold, you can set up Postal, an open-source mail server that offers a self-hosted equivalent to API-based mail services I mentioned above.

These choices all come down to your comfort level, your technical skill set, and what you’re really comfortable with doing. I think most people looking for an alternative will probably land on Ghost, but the other options have lots of merit based on what you’re trying to do.

The challenge, honestly, is the tyranny of choice. It takes research and time. As Linux users will tell you, the hardest part of using Linux is deciding the exact distro to use, because there’s so much choice. It can be overwhelming.

If you send emails at all seriously though, spend some time trying to find your “distro.” Use a process. There are lots of options, enough that you might just be able to find a perfect fit.