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Twice a week, Ernie Smith sends the latest edition of Tedium to thousands of curious inboxes. The byline, the dull side of the internet resonates with a deep exploration into the fascinating and the esoteric. It embodies a curiosity to research and tell the story nobody else tells.

For this issue of the Letterlist interview series, Ernie talks about indie publishing, digital share-cropping, and trapper keepers (Don’t worry, I had to google it too).

Tell me about Ernie. Where are you? Where did you grow up?

Sort of by my nature as a onetime newspaper guy, I’ve lived a lot of places. I grew up in the midwest, and after college, I’ve spent time working as a designer for newspapers in Milwaukee; near Hilton Head, South Carolina; in Norfolk, Virginia; and in Washington, DC. These days, I’m in Virginia, but I’m not in newspapers.

I have to admit, though, I sort of feel like I’ve grown up with the internet, in ways big and small. Despite all my moving around in my early adult life, it was a constant—I could always trust that I would find something interesting there, whether on a BBS or early Freenet, via some early websites, or by staking a claim at some platform like the Something Awful forums or Tumblr.

I guess, in some ways, I sort of see my digital life as a big part of where I grew up.

The big turning point came for me at the end of 2008, when the newspaper I was working at, this daily paper printed by the Virginian-Pilot, folded. It was called Link, and it had a very interesting approach to content, in that it broke details down into big numbers and quotes.

Yes, I got laid off, and while it stunk to lose a job, I was more frustrated by the loss of the idea. That led me to create something of a Web equivalent called ShortFormBlog, which was basically a news site that told stories using nothing but short blurbs, numbers, and random graphical elements I came up with. I worked on that for a little more than five years—first with WordPress, and then on Tumblr, where the idea really took off.

What else are you working on?

I do a mix of things. By day, I work for a content marketing company called Manifest, and my main project with them is called Associations Now, a publication of the American Society of Association Executives. I think a lot of my sensibility comes from the fact that I’m very comfortable with niche topics—which I write about all the time for Associations Now.

On top of that, I try to stay active as a writer and have been an active contributor to Vice’s Motherboard, for which I wrote a lengthy history on the early NES emulator NESticle back in May.

How did Tedium come about? Why did you start the newsletter?

In late 2014, I had shut down ShortFormBlog, which had been successful and had around 160,000 followers by the time I closed its doors, but I thought had some limitations that would prevent it from becoming a bigger success. For one thing, nearly all my audience was tied up with Tumblr, a platform that was difficult to monetize. I felt like I was renting my readership, rather than owning it outright.

The other issue was that it had gotten to be too much work. Part of the problem was that it was built entirely around the news cycle, which meant that you always had to be on, and ultimately, the things I wrote about had a half-life of around twelve hours. At one time, I had other writers helping work on it—all of whom have gone onto work with larger outlets like Bustle, The Daily Dot, and AdWeek. But in the end, it was basically the world’s most ambitious side project.

So I went to the drawing board and decided to build things in a way that worked basically the opposite from what I knew to be successful on the Web at the time. I published small amounts of content, instead focusing on a couple things a week. I actively avoided most social media, Facebook in particular. My images were washed out, animated, black and white, and often pulled from completely random places. And I didn’t have a website at first; it was just a newsletter and a landing page.

And, of course, the topics—oh, the topics. I decided to go deep on things that a lot of writers would have avoided or ignored, like the history of ranch dressing, obscure television, or why office supply stores were horrible. The subject lines were designed to be low-information, so as not to scare you away from the piece by topic alone.

The onus was on me to prove that these topics were actually interesting. The only thing they had in common is that the articles were evergreen and I had researched them on the internet. To be honest, I think the topics have only gotten weirder from there.

And unlike my old site, everything was really long, rather than really short. Compared to most email newsletters, which are short and designed to get you to click on links, mine averages between 1,500 and 2,000 words and is meant to get you to read in your inbox, or if you feel like it, your web browser. (I did eventually build that website.)

About the only thing I kept from ShortFormBlog was the design sensibility and color scheme (which I liked), with some modest updates. (The numbers and quotes and lists are kind of a hallmark of my writing and you’ll never be able to pull them from my grubby paws.)

I had this weird idea—basically, I wanted to start a platform where I did everything wrong in terms of what drove success on the internet, according to convention. And I wanted to see if I could be successful anyway by doing everything wrong.

How many subscribers do you have, right now? What have you done to foster your audience?

Currently, I have around 8,600 subscribers, give or take a few. Generally, my approach for building audience has been a mix of word of mouth and syndication. (A mention on NPR’s Planet Money back in February was a shot in the arm, admittedly.)

The great thing about writing long pieces for each of my issues is that they can be shared with other outlets and live a bit of a second life elsewhere. I work most closely with Atlas Obscura and Vice’s Motherboard, and the only thing holding me back from doing more syndication, really, is the fact that I only publish a couple of pieces a week. Despite writing literally 5,000 words a week just for Tedium, I’m actually working less than I did during my peak years on ShortFormBlog.

And despite the fact that I have a smaller audience than I did with SFB, Tedium does better for itself—in part because I work hard to keep costs down (Email Octopus, my email provider, has been a huge help on this front), and in part because I’m a little more transparent about the fact that I’d like to cover the costs of running this thing.

Unlike the days when I had a site with an ungodly amount of followers on a social network I didn’t own, I feel like I earned all my followers this time around. That feels pretty good.

What’s your big goal for Tedium? How does it fit in with your other projects?

I think I’d love to have this big body of work that is totally unique, something that people can look at and learn a lot from. Maybe that’ll lead to a book someday or something else. But I think it’d be great to turn this project into something where it allows me to call the shots on my own career a little more. In some ways, I think that’s already happened.

One thing I frequently get asked about is the idea of doing a podcast. And to be honest, I’m not sure that interests me. I struggle with it. I realize the economics of podcasts are a bit nicer than newsletters, but I think I’ve always been better with a turn of phrase when I’m writing it down than speaking it out. And I like the workflow that comes with words, too.

Maybe the right approach will show itself someday, but I think that it’s easy to take the road that everyone else seems to be taking. Choosing the path less traveled has worked pretty well for Tedium so far.

What is it about email newsletters that makes them so enduring? How do you see email publishing playing out over the next 3-5 years?

I think email newsletters highlight an ability for creators to have a little more control over the process of sending out content, as well as for readers to look at it without the overwhelming influence of social media guiding their every move.

The thing is, social media and search engines tend to have a shaping effect on the creation of content, and not one that’s always positive. There’s a bit less of that with email; while email strategy certainly exists, it differs significantly from what makes a successful web article, creating more room to experiment with the form. You can play with the element of surprise a little more. You can focus less on headlines and more on the actual things you want to talk about.

In the long run, I personally feel that the form is going to allow for more interactivity and stronger design, as older email clients fall into disuse, clients like Gmail strengthen their support for technical things like media queries, and email development frameworks like MJML help to bring more flexibility to the medium. Flexibility is something that is sorely lacking when email design is largely built around tables. I’ve worked hard, personally, to not just write emails, but actually code something of my own.

What’s your business model for Tedium? What have your experiences with Patreon and sponsorships been like?

I think, to be honest, it’s the idea of having interests in a lot of things. Syndication has been a successful financial stream for me, but I also use things like affiliate links, which I try to be absolutely up-front about. One of the things I like to do from time to time is link something completely absurd that is actually sold on Amazon, like an envelope moistener or a book that’s long been out of print.

I remember a few years ago when the blog Brain Pickings ran into controversy because it used affiliate links. That controversy, which happened while I was working on ShortFormBlog, stuck with me, because the thing is, the only real problem in that situation was the apparent lack of disclosure, which was easily fixed. The idea of linking to (for example) interesting books about offbeat topics is sound, as long as you say out loud, “Hey, I do this, it’s a way of supporting my work.” I’m a realist about advertising and understand that it can be effective if done well.

Obviously, sponsorships have the biggest potential in the long run, and that part of the model has seen growth in the past couple of months thanks to, which has done newsletters a real service. Patreon has done OK, though I haven’t pushed it aggressively because I think readers should have the choice. But I’ve done some interesting things on that front—I have a tier where if you pay $25 a month, I buy you the weirdest possible thing I can find on Amazon every month. I shipped someone a copy of Mavis Beacon Teaches Typing one month.

The idea of doing a lot of things to support this newsletter I think is more effective than sticking with one and getting lucky.

From your experience publishing in different formats, can you describe how you approach sustainable and profitable indie publishing?

I think I learned a lot from my time doing ShortFormBlog on this front, as well as my time with newspapers. When I was with newspapers, I felt like—at every single publication I worked at—I was completely separated from the business side of matters. And admittedly, there were probably good editorial reasons for that, but I felt like it put me at a loss when I wanted to become a little more entrepreneurial. When I started doing ShortFormBlog, I ultimately felt that I didn’t really have an understanding of the business side of things. In 2009, there were a lot of attempts to share-crop the advertising game when it came to websites, and I feel like the model ultimately required successful websites to take a certain shape.

Moving out of newspapers I think gave me more of an understanding of the other side of things, and over time I learned more about it from doing ShortFormBlog for a bit longer. It became clear that the idea of SFB simply did not lend itself to a more traditional revenue model.

So with Tedium, I thought in terms of models that I learned about over the years that I respected—specifically, The Deck, which shut down earlier this year but I think had the most interesting model out of any advertising firm, and The Wirecutter, which I admired for its transparency around affiliate marketing—and tried to come up with a model that would lend itself to similar ideas but also take its own unique approach.

I also decided when it came to SFB that I was done with sharecropping. I’m not opposed to working with outside networks, but I don’t want to be reliant on a network like Tumblr for my audience. If I want to move from doing Tedium to another project someday, I can take my current audience with me. I couldn’t say that about ShortFormBlog.

I’m obsesssed with other peoples’ workflows. Can you share your process, from coming up with an idea through to hitting send?

As far as formulating the ideas, I think it’s a mixture of things. A lot of it is being observant about the things I see around me, or seeing something buried in a much longer piece. This is kind of the strategy I took with ShortFormBlog, but instead of applying it to news, I apply it to weird stuff and see if there’s an interesting history there. Sometimes, looking into the history of one thing, such as when I highlighted the story of the Bose Wave, will expose a completely different topic, such as a showdown at MIT over an obscure radio standard.

People regularly send me ideas, and I’ll say that a lot of them have potential, but there are specific things I look for in a pitch. I try to do things that haven’t gotten a lot of attention previously, or at least haven’t been highlighted in a way where the specific story angle has been brought together in one place. A good example of this: recently, I wrote a piece on Heartland Music, a big seller of music on TV in the ’80s and ’90s, but one that had been overshadowed historically by an earlier competitor, K-Tel. My inspiration there was because I listened to a John Denver song.

Or maybe there’s a narrower angle I can highlight—an example on that front that comes to mind is that I did a story on Trapper Keepers, a topic that Mental Floss had written about at length in the past. But rather than focusing on the folders specifically, I angled my story around the fact that they tended to be banned by schools due to the fact they were so big.

I try to focus a lot on “blue water” with my story angles, because ultimately, I know that the best story is the one I can get out in front of.

On the production standpoint, I write everything in Markdown—absolutely everything. I have a lot of opinions about word processors, and I find that I simply write faster with Markdown, which puts more focus on the keyboard. I’ve gone through a few editors over the years, but the ones I use most frequently are the macOS app Bear and the Web-based app Gingko. I tend to write and research at the same time quite often unless the angle requires a different approach or necessitates an interview or two. It’s a strategy I’m used to because of years of news-writing.

I do a lot of deep diving to find my research materials, with my favorite tools for deep dives being, Google Books, the Internet Archive, and Open Library. I love highlighting old articles, interviews, and stuff like that. I’m not afraid to pay for these resources if necessary, but I will say that I find the way that copyright issues have limited the spread of certain kinds of content is frustrating—and it’s an issue I speak up about a lot.

As far as how everything gets turned into a blog post or newsletter, I use Ghost as my CMS of choice. It’s a good platform and has a lot of interesting things going for it. I’ve had to hack it a bit for my purposes, as I use a lot of additional CSS beyond the Markdown spec. I’ve been working to ensure that there’s more parity between how I write my emails and how I do my blog posts, and these days I use a locally hosted version of Ghost for my emails and a remote-hosted version of Ghost for the web. The locally hosted version uses my custom-built template, which I then push over to Email Octopus and send out.

There’s a lot of midnight oil that goes into each issue of Tedium.

I love your approach of “doing everything wrong”. Can you share 2 examples where the contrarian approach paid off for you?

I think the approach shows its benefits the most in the articles I end up writing about. I would say that perhaps one of the most popular articles I did was a story about the invention of the cheese curl, in which I looked into a topic that I don’t think had seriously been considered by any other writer. That story—which got mentioned by a lot of news outlets, including HuffPost and Fox News—drew a lot of attention to what I was doing, and I don’t think if I approached it from a traditional angle, I would have even found that story.

I think the other thing kind of ties to a letter I received from a reader recently, who took issue with some of my design decisions on the website, including using a more stark look and using low-information headlines on my front page. The thing is, a letter like that is rare. More often, what I hear is that I’ve created something of a rabbit hole—where people will randomly dig into articles I wrote months or years ago because the content never really loses its lustre. I don’t think Tedium should have a traditional style because then it becomes like every other site. It’s good to draw a line in the sand and say no sometimes.

What big idea would you love to work on if you had unlimited time and money?

Honestly, this is pretty close to the dream for me, though I wish I had more time to work on it than I do now, and it would be nice to do it full-time someday. I would probably say, though, that I would probably spend more on research materials, and I would also aim to, someday, write a book of tedious things—maybe make it like a coffee-table tome or something.

I just want to be able to highlight interesting stories.