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Tedium: The Internet’s Last Soapbox

In today’s deafening din of social hooks, emotional triggers and distractions, it seems that there is only one digital sanctuary where we are in control of our attention: email. 

Yes there is spam and the usual deluge of travel site promotions. But we’re still able to silence it with a swift click of unsubscribe, customizing our inbox for information we deem important and/or entertaining (hopefully both). 

The best email content is able to take advantage of the intimacy, trust, and solitude the channel provides. It’s able to silence distractions and take the reader on an informative journey. 

One of the original templars of this notion is Ernie Smith. An adamant proponent of giving (brain) power back to the reader, Ernie is the author of Tedium, a long-form newsletter covering obscure, almost anti-viral content. 

He is a one man show: he built his site and design from the ground up, hacked together a tool to convert blog posts into email-formatted content, and even did a zine before. You can’t get anymore punk than that. He does all this while maintaining a full-time job. 

To learn more about how Ernie attracts, engages, and maintains his audience – and a bit about his geek-maverick philosophy – we spoke to him on the phone for our Edge Group interview.

The anti-viral campaign

Several times a week readers open up obtusely-titled emails to find lengthy editorial newsletters on subjects like Microsoft’s forgotten MSX console, the difficult art of stage banter, the history of dryer lint (“Like lint? This article is for you”), and the story behind magic kits

The topics are like The Upside Down versions of Buzzfeed pieces: they are as far away from celebrities and cats as you can get. And despite their obscure subjects, these deep dives don’t waste your time. There is a certain joy in understanding something that you never really thought was important… until Ernie explained why you should care. 

Against the grain

After a successful but stressful five-year stint with ShortFormBlog, Ernie felt somewhat burned out and wanted to start something less frequent, more focused, and generally different

Voice is a universal constant in marketing. Whether you’re a lone influencer or a multinational with hundreds of thousands of employees, consistent brand voice is the one factor that doesn’t fluctuate in importance. 

When Ernie decided to go the newsletter route, but he didn’t want it to be like any of the newsletters that were out at the time.

“I’d always had a conversational approach to how I wrote. I was thinking more in terms of – here’s the specific direction where I want to take this. I wanted to actively write something that was going against the grain. Inspiration-wise, I took less cues from newsletters and more cultural things that hadn’t been discussed a lot and would probably find a home on this newsletter.”

Content for robots

With social, the distribution platform is built-in: once you hit send, Twitter or Instagram robots use whatever tags or keywords you’ve included to make sure your content gets in front of the right people. Of course, with a sea of competitors, you have to publish frequently to stay relevant or risk getting drowned out. 

\With blogs, you’re writing for SEO robots – don’t publish articles with relevant keywords, or don’t put out content often enough? The biggest distribution platform on the planet – Google Search – will rank you lower than your competitors. 

Apps are a different story – ratings and downloads determine rank (and by direct extension eyeballs), not frequency of updates or relevant elements.

Each of the above channels relies on elements creators don’t have full control over. You’re making content, at least in part, for robots. 

Newsletters flip things around. You’re the majority shareholder when it comes to cadence and distribution. You choose the pace at which you send emails – the SEO gods won’t smite your newsletter to the abominable second page for publishing once a month, nor will social robots use your content as fodder for neural stimulation. And you’re not competing for stars or downloads. 

Distribution isn’t handled for you, either. It’s up to you how you get your newsletter list to grow. Ernie sees a rare opportunity here:

“[Newsletters] encourage us to think of a different way to push content to people. Social media benefits from giving people what they want, but there’s still room for sites that have a specific mission, and aren’t trying to kick in the endorphins every time people read.” 

Night of the living content

Ernie pays serious homage to Millenial and Gen X nostalgia in his work. He has a deep love for the things many of us grew up with. So it’s no surprise that he refers to reused content in his newsletters as reruns

Content isn’t a one-and-done-deal for Ernie – older pieces aren’t meant to stay in the ground for long. Ernie sees a sort of philosophical reason behind this:

“A lot of creative folks, be they songwriters, or authors, or whatever, will go back to their older material and try to see ways to improve it.”

Because Ernie’s content is evergreen – it doesn’t “age” like a current events piece – he is able to revive old articles that are suitable for the moment, update them, and re-publish them in the newsletter. “Living content” works well for the medium. There are people on the list that weren’t there three years ago, so old pieces can still provide value to new readers.

Ernie’s open world

Voice is king for Ernie. It’s his tone that distinguishes his content from other newsletters. He has occasional contributors, but even then he is careful that they maintain the Tedium tone. 

Still, Ernie is passionate about writers contributing to his world… as long as it furthers the newsletter’s mission: exposing people to stuff they normally wouldn’t see. 

“My perspective on the world is mine alone, and I want some room there for other people’s perspectives. The fact of the matter is, I’m a white guy. There are a lot of us online. While I can have different thoughts on things, I’m not necessarily 100% unique here. It’s good from my position as a writer to be looking for these different perspectives.”

His version of Tedium is going to be different from someone else’s. As long as that version furthers the overall mission, Ernie is open to incorporating it. 

More to life than newsletters

As an indie newsletter creator with a mission to push obscure content, you can imagine that Ernie’s approach to newsletter analytics is very different from, say, Morning Brew, which is designed to get people clicking on external links… or a publisher like the New York Times, which wants people to funnel into their site from a slew of newsletters and subscribe. 

Ernie relies on basic analytics, with a baseline he tries to hit each time – something like a 30% open rate. He says he looks at analytics less aggressively than a larger business would. If open rates dip below 28-30%, he figures that the subject isn’t exactly right for the audience. Analytics is more of a compass vs. a driver for Ernie. 

But all is not lost if a certain newsletter doesn’t perform well.

“If a newsletter doesn’t do well in the inbox, but there are other signs that it did well, like it gets a prominent link from a site like Digg or another media outlet, that eases concerns I might have about performance.”

He gives an example of a piece he did a few years back about weird phone numbers (as in, when you dial them, something weird happens). 

The piece did modestly the first time he wrote it, but since then it exploded on organic search, getting daily traffic to this day. 

“I’m aware that because this content is also on a website, it doesn’t necessarily have to die after it ends up in somebody’s inbox.”

Antithetical growth

Ernie isn’t overly aggressive about growth: 

“I’m not trying to double my subscribers in a year. To a degree that’s antithetical to a newsletter about tedious topics. It’s designed to be around niche subject matter.”

That means unsubscribes take a different meaning for Ernie. Surprisingly, he compares his view of unsubs to that of an ecommerce business. 

Just instead of, “oh, that person wasn’t going to buy something anyway,” it’s, “that person wasn’t right for the newsletter anyway.”

The scrappy ESP

As an independent creator, Ernie is cognizant of price. If he was on MailChimp, it would cost him three times as much as his current ESP, Email Octopus, which relies on Amazon SES

Email Octopus isn’t a large company itself, which appeals to Ernie. 

He wants a scrappy ESP because he’s scrappy himself (a great lesson for newsletter teams – go with an ESP that reflects your values). 

When he gets on the phone with support, he talks to someone with a similar mindset: 

“They’re small enough that if I have a suggestion about something they can do better, they’ll respond to that concern and I feel I have a direction where their product goes.” 

Once a hacker…

Ernie’s a hacker. And like many hackers, he’s spent a considerable amount of time hacking together tools that will make his life easier. Namely, the translation of blog content into email content, and the creation of email content itself. 

In a 2016 Medium blog, Ernie laid out the redundant nature of email creation still in full effect today:

“There’s a lot of HTML code, a lot of copying and pasting, and a lot of potential for things to break, and custom templates can be a bit of a minefield. A single out-of-place tag can gum up the whole works.”

In the post, he used Ghost, Email Octopus, and a custom-built plugin to convert blog posts into emails. He has since transitioned to Craft CMS, still uses Email Octopus, and employs shortcodes that help with the transition between web and email content. He expanded on this during our chat:

“I ended up with Craft CMS, I had a bit more control over different views. One of the ways I could manage it, I could build up email in the CMS, and when I publish it readers would get the main view, but there would be a separate view that would take that code and convert it to something email friendly using shortcodes. The shortcodes would do one thing for the site, and something else for email. The result saves a lot of time.”

Another tool that Ernie has found useful is MJML, basically a scripting language specific to email.

Offbeat affiliate links

There are a few ways Ernie is monetizing Tedium. He started using Google AdSense this year, has done a number of sponsorships, has Patreon set up (we recently got a copy of his awesome zine), and – our favorite – “offbeat” affiliate links. 

Since he often mentions obscure items in his posts, he has affiliate links to corresponding Amazon products. This is the first we’ve heard about someone capitalizing on products that almost never see the light of day, and we love it. It’s a direct reflection of Ernie’s rebellious side.

Favorite Newsletters

Creators are consumers. And you can tell from a few newsletters that Ernie is a voracious consumer of a variety of colorful content. We asked him what his favorite newsletters were, and he dropped a few interesting names:

Morning Brew: “I think they have a really slick approach. It’s about business subjects, but isn’t done very aggressively. It’s written in a way where it’s someone trying to explain business in a way that doesn’t bury you with numbers.”

American Press Institute: “I read a lot of newsletters that are journalism-related.” 

Substack: “People [here] are doing some cool stuff.”

Atlas Obscura: “I always loved what Atlas Obscura has done with newsletters. I think their content really matches the newsletter approach.”

Really Good Emails: Of course.

Action Rocket: “What they do that’s really cool is they say that their newsletter is in permanent beta. They’re willing to try some things that might break in some clients, simply because it’s not really being done elsewhere.”


To sum up, here are the key lessons we’ve learned from Ernie’s approach to newsletters and newsletter analytics:

  • Newsletters have a different cadence and distribution mechanism than other platforms. You have more control and freedom of when you publish and how you grow your audience, since you’re not under the thumb of robots.
  • Newsletter content is “living content” – if the subject is evergreen, you can repurpose it – do “reruns” – of archived content, updating it and publishing it again for your list.
  • Ernie maintains tight control over voice, but is open to others’ perspectives as long as it pushes the newsletters mission – introducing people to content they wouldn’t normally come across.
  • His approach to analytics is different from a publisher like Morning Brew or the New York Times. Since his newsletters are long-form content with few links, he uses open rates as a base benchmark, but isn’t too concerned about list growth, as opposed to maintaining list quality.
  • Just because a piece doesn’t do well in a newsletter doesn’t mean it won’t kill it in social or organic search.
  • Since he is an independent creator, cost is important to Ernie, which is why he uses Email Octopus instead of MailChimp.
  • Ernie also prefers a scrappy ESP because he feels like his suggestions influence their direction.
  • Since there aren’t any end-to-end solutions that allow for the creation of newsletters and the porting of newsletter content to web (or vice versa) all under one SaaS roof, Ernie, like many other newsletter publishers we’ve spoken to, has hacked together his own solution.