I've Built Two Successful Substacks. Here's What They Have in Common.
One does premium info and product sales; the other, a small town newspaper, is a top-100 News publication on Substack. While they look nothing alike, the strategic foundation beneath is identical.
Most people who try to build a publication on Substack fail at the same point.
They write good pieces. They build a small list. They publish consistently for six months. And then conversion to paid stalls out at one or two percent, the writing starts to feel like a treadmill, and they slow things down.
The diagnosis they reach for is almost always the same: I just need to write better content. I need to find my voice. I need to post more consistently. I need to figure out what makes me different.
Sometimes that’s true. Usually it isn’t.
The actual problem, in most cases I’ve seen, is upstream of the content. The publication is built backwards. What I mean by that is that the writing came first, and the structure that converts readers to paid subscribers was supposed to figure itself out later.
It doesn’t. It can’t. Conversion architecture is a strategic decision, not a content quality outcome.
I’ve built two Substacks that converted well, in two different ways. I've also built publications that didn't work, and I learned just as much from those as from the ones that did.
Midlife Nomads, the publication you’re reading now, helps people in their 40s, 50s, and 60s redesign their work and lives toward more flexibility, autonomy, and travel. It’s been a top-100 publication in Travel in the past. Now, it’s monetized through a combination of paid subscriptions, sponsorships, and product sales.
Owen Sound Current is something else entirely — local news for a small city in Ontario, Canada. It runs on paid subscriptions only with zero advertising, has been a top-100 News publication on Substack for over a year, and converts just under 12% of total readers to paid. More importantly, that rate has held steady through more than two years of operations — most publications see conversion degrade as they scale, and Owen Sound Current hasn’t.
And before we go any further, it’s important to note that Owen Sound Current isn’t a solo project. It’s a partnership with Maryann Thomas of The Ginger Press, an experienced publisher who handles the strategic direction, insurance, legal, and operational architecture that any serious news publication needs.
I bring the editorial work, the conversion architecture, and the digital expertise. She brings the publisher’s discipline and decades of book and magazine publishing experience. The publication works the way it does because both of us are doing what we’re best at, and neither of us could have built it alone.
That matters for what comes next in this piece, because most of what I’m about to walk you through is strategic and structural — and getting the strategy right was a collaborative process, not something I figured out by myself.
The principles hold regardless of whether you build solo or with a partner, but I’d be misrepresenting the work if I told this story as a one-person project. We’ll be talking more about the power of partnerships and joint ventures in the weeks ahead.
For now, know that those two Substack publications I’ve built could not be more different on the surface. One is for an international audience contemplating a life change. The other is for the people on my street, telling them what’s happening at the city council meeting.
The voice is different. The cadence is different. The economics are different.
And yet the strategic foundation driving their success is the same.
The local news version is the cleaner test of whether the foundation works for subscriptions, because local news is the hardest category to monetize on Substack. Local media has also been in structural collapse for two decades, and even the most well-funded efforts have failed.
Canada has lost hundreds of community papers since the early 2000s. Vast regions have become news deserts where no one is covering city council, no one is reading the meeting agendas, no one is asking what happened to the infrastructure tender.
Major corporate efforts at filling the gap have folded. Well-funded nonprofit ventures have folded. Local news is, by any honest measure, the hardest place in publishing to make economics work right now.
If the principles hold up there, they hold up.
What I want to walk you through here is what those principles actually are. Because the difference between a publication that converts and one that doesn’t usually isn’t visible in the content. It’s visible in the architecture the content sits inside.
And why are we talking about this on Midlife Nomads? Because as we talk about building income streams and recurring income, this is one platform you should be considering. There are Substacks for every interest now, and if you’re building community and authority in a space, the platform takes a lot of the technical and integration legwork out of getting yourself out there.
Good News: You Probably Don't Have a Content Problem
Most aspiring publication owners think they’re solving a content problem. They’re not. They’re solving a positioning problem disguised as a content problem.
The publications that convert paid subscribers reliably are the ones where four strategic decisions have been made — explicitly, before any pieces are written — and where every piece of content that gets published reinforces those decisions.
The publications that struggle are usually publications where one or more of these decisions has never been made, or has been made implicitly and inconsistently, or has been left to emerge from the writing itself.
The four decisions are:
Who, exactly, the publication serves — and who it doesn’t.
What that reader believes when they finish reading you that they didn’t believe before — the shared conviction at the centre of the publication that unites you and your reader.
Where the value lives at each tier — what the free reader gets, what the paid reader gets, what the role of each is in the funnel.
How conversion happens, mechanically and regularly — not as an annual launch, but as a built-in part of how every issue is structured.
A publication where these four decisions are clear, consistent, and reinforced by every piece of content will convert. A publication where any of them is fuzzy will struggle, regardless of how well the individual pieces are written.
Conversion is structural. The content is downstream.
If you’re nodding because this matches something you’ve been suspecting, keep going… the rest of this piece walks through what each of those decisions actually looks like in practice, including the specific architecture that makes Owen Sound Current convert paid subscribers in a category many people struggle to monetize.
