Writer or publisher: ya gotta pick one

Freddie deBoer, writer, and the FreddiedeBoer Substack are 2 different businesses requiring separate strategies

Perfecting Equilibrium Volume Four, Issue 16

If it were easy as fishin' you could be a musician
If you could make sounds loud or mellow
Get a second-hand guitar, chances are you'll go far
If you get in with the right bunch of fellows
People see you having fun just a-lying in the sun
Tell them that you like it this way
It's the work that we avoid, and we're all self-employed
We love to work at nothing all day

And we be taking care of business (every day)
Taking care of business (every way)
We be been taking care of business (it's all mine)
Taking care of business and working overtime

The Sunday Reader, Sept 21, 2025

We were freezing from the waist down in the winter waters of the Naugatuck River, despite our neoprene waders. We were sweating from the waist up, grunting as we passed heavy pails slopping river water to the middle where we dumped young Atlantic Salmon into the river, hopefully to re-establish themselves where they once thrived.

The sport of kings had returned to the Naugatuck. When a friend heard he leaned in and said conspiratorially: You’re going to love fly fishing for salmon. It’s better than sex.

Now that I’ve done both, all I can say is either that guy was lying. Or I’ve been doing one – or both – wrong.

In the river we were chatting between buckets, the way guys do during manual labor. I’m going to take the buyout and retire, Tom said. He said he’d grown tired of teaching the same math lessons to class after class of bored high school students, year after year.

What will you do? You’re too young to sit home yelling at the TV all day.

I’m going to be a writer, like you. I’m going to be a professional outdoor writer. A flyfishing writer.

I sighed. I grunted. I carefully passed him a salmon, flopping confusedly half-in, and half out of its bucket. What if I slipped and it fell in the river?

Never mind. The cold water sucks all heat and thought out of your body.

You cannot be a professional writer like me and write about fly fishing, I told him. Patiently. It was a talk I’ve given to everyone who brings up this subject.

You have two choices. You can be a professional writer, supplying a market and making money. Or you can write about what you want and not worry about making money, like Emily Dickinson.

I. Want. To. Write. About. FLYFISHING!! He enunciated, grunting through the weight of another salmon.

No one cares, I told him. Either you want to make money writing, in which case you need to run it like a business, or you don’t care about making money, in which case your writing is a hobby.

He fumed for a bit, then asked what I was writing about. Large-scale shaftless press technologies, I told him.

Sounds boring, he said.

Sounds like a dollar a word, I told him. One phone call, an hour writing 500 words...$500. In 1989.

But Tom wanted to write about fly fishing, so Tom wrote about fly fishing. And made so little money he ended up going back to teaching.

Writing professionally is a business, and you have to run it like a business. Freddie deBoer knows this; he’s been a successful professional writer for a very long time. So why is he now writing this on his Substack paid newsletter?

The newsletter has steadily been losing subscribers and revenue for several years. This hasn’t been and still isn’t a disaster. When I reached a peak in early 2023 or so I knew that I would fairly quickly reach a stage of managed decline - that is, I was pretty sure that my concern would inevitably be maintaining rather than growing.

What Do You Guys Want This Thing to Be?

He goes on to speculate that the decline is due to some headwinds: saturation of the newsletter market; people aren’t that interested in criticism of liberals and liberalism from the left now that the left is largely out of power; and so forth. But the actual problem is structural:

Freddie DeBoer, professional writer, and the Freddie DeBoer newsletter are two separate and somewhat incompatible businesses requiring separate business logic.

Here’s how each works. First, let’s look at how a professional writing business works. I spent years establishing myself with the dozen or so magazines that focused on publishing technologies: The Cole Papers, News Inc., TechNews, and a bunch of others. By the time I had that conversation with Tom I was one of handful of writers who could turn around an announcement of a new press technology from, say, Goss, get an interview with their engineers, and explain it in 500 words. On deadline.

So I didn’t need to pitch articles anymore; even though I wasn’t on staff, all those magazines were quick to assign me articles on a regular basis. It got to the point where I had to gently turn down editors because I’d already accepted an assignment to write about the same tech announcement for one of their competitors.

The Iron Law of Business is that a Customer is Someone Who Gives You Money. If they don’t give you money, they are not your customer.

Here's the logic of the professional writing business: Your customer is the publication that gives you money. Not the readers. Not the advertisers. So a successful writing business focuses on building a brand that publications consistently pay.

And those publications may be niche editions invisible to the general public. The Cole Papers? NewsInc? Who ever heard of TechNews?

Who cares? They paid well. That’s what counts when you are running a business.

Lots of people dream of writing The Great American Novel. Pretty sure no one has ever dreamed of writing The Great 500-Word-Explainer On Large Scale Shaftless Press Technologies For Some Business Magazine No Normal Person Has Ever Read.

But business is not about dreams. It’s about money.

So where’s the money in the publishing business? Who gives a media business money?

Media businesses in general – and publishing in particular – are all about audience management. Media brings in money through a number of channels: advertising, subscription and membership fees, sponsorships and the like. All these channels require building, maintaining and growing an audience.

Some audiences are direct customers who pay subscription or membership fees, like Freddie deBoer’s paid subscribers or Netflix’s users.

Some audiences are actually the product for sale; television and radio bundle up their audiences into demographic slices and then sell those to advertisers.

In all these cases, building, maintaining and growing that audience is core to every publication’s strategy. You have to build an audience, find an editorial product that can pull a critical mass of subscribers. You have to maintain that audience, publishing good material regularly so reading your publication becomes an established habit.

And then you have to grow that audience. This is where most new publications fall down. It’s where Freddie is now struggling.

Here’s the problem: Interests change. People change jobs.

Life happens.

No matter how good your product is, you are going to consistently lose a portion of your audience through no fault of your own. So you have to grow your audience by bringing in new readers and viewers and users, or your publication will die.

Take those articles about large-scale shaftless press technologies. It’s a pretty good bet that the people reading those articles were in publishing technology jobs.

And it’s a pretty good bet that those people stopped reading about large-scale shaftless presses the minute they got promoted. Or fired. Or changed jobs.

So successful publications bring in a constant stream of new readers to replace those that fade away.

It’s instructive to pick a successful publication and look through their archives. One thing that’s apparent is that there’s a certain dichotomy between what’s good for your long-time audience, and what’s needed to attract a new audience.

Take a look at, say, a photography publication. Once you’ve run an article or two about The Rule of Thirds, or the basics of exposure, any more on that will be a rerun for your long-time users.

But that’s exactly the type of content that will bring in new users and grow your audience.

That’s where Freddie is stuck right now. Earlier this month he wrote a piece for his Substack newsletter entitled Education Doesn’t Work 3.0. Here’s his introduction:

This is the third iteration of my longform argument that the relative position of students in the academic ability spectrum (that is, the rank order of students as determined by quantitative educational metrics) is remarkably static over time, even in the face of massive spending and intense intervention, and that this persistence fatally undermines modern assumptions about schooling, its purpose, and its potential. The first iteration of this post is here and the second is here. Though large pieces have been preserved, this work is mostly new, with at least 10,000-12,000 words of new material.

Who is this for, exactly, among the newsletter’s audience? How many long-time subscribers are going to sit through a third massive helping of 10,000+ words making the same basic arguments? Especially when the piece starts out with an anecdote excerpted from his book on the same topic? On the other hand, how many first-time newsletter readers are going to wade through 10,000+ words as a first course? Especially one that starts out by saying this is version three?

I’m not criticizing here. This is a standard best practice for a professional writer. As I mentioned earlier, I wrote article after article about press technology, and there was a lot of overlap between those articles. That’s part of being a beat writer; change tends to happen incrementally, and you have to bring your readers up to speed because you cannot assume that they have read all the earlier installments. This is a best practice for professional writers because the articles are appearing in different publications, and therefore being read by different audiences.

FreddiedeBoer.Substack.com is a newsletter with a single audience. For all the work and thought Freddie put into this, it’s a piece unlikely to grow new audience for the newsletter, or do much to preserve the existing readership.

Elsewhere on the Internet there’s a train wreck unfolding at another publication. I’m not going to give details; embarrassing this writer would be cruel and pointless. But the situation is instructive in an unfortunate way.

This writer has been successfully running an online publication for decades. That’s the good news. The bad news is that the publication was built on a hosting site using that hosting site’s address; the writer had an address, but never got around to setting it up.

For more than a decade.

Now the hosting site is closing down at the end of the month. The site – the business – has to move to a new host. At a new address.

The publication needs to get a new host, with an address it controls, and move the audience there. Tough to do by the end of the month, but doable. There’s always audience loss in a situation like this; that’s why you need to own and control your address.

So what’s the writer doing? Naturally, he’s stopped working on the permanent site and starting writing for a third site. With a third address. Naturally.

Writer or publisher: ya gotta pick one.