Newsletter Circle is the newsletter all about newsletters for indie creators.

👉 Every Sunday, you will read the unique journey of a different newsletter creator and learn more about how to start, grow and monetize your own newsletter.

👉 Every Wednesday, you will read articles and the list of curated resources to level up your newsletter business.

🎙CREATOR INTERVIEW

Terrell Johnson has been running his newsletter “The Half Marathoner” since 2015 and is currently reaching over 42,000 subscribers.

He started his journey with a website; the newsletter was just a tool to bring traffic to the website in the beginning.

Today, he says there are days he feels like this is his life’s work.

Terrell shared so many great insights about his journey transparently.

A few headlines that we talked about:

• Change in the role of his newsletter over time

• Behind the scenes of his paid subscription strategy as a creator who has over 650 paid subscribers

• His experience with the offline subscriber meet-up

• How he successfully built a community spirit with his readers

Let’s dive in!

🏷 NEWSLETTER IDENTITY CARD

🛠 Tool Stack

• ESP → Substack

• Payment → Stripe

👋 MEET THE CREATOR

Welcome Terrell. Let’s start with getting to know you.

Sure! I’m an avid runner, reader and writer who lives in Atlanta, Ga., with my family, and I manage The Half Marathoner as a side project/business. (I’m a UX writer in my day job.) 

I started it after reading an article in the Washington Post about people who owned websites who were making money from Google’s then-brand-new AdSense program, which involved placing text ads on your website, which Google would then pay you for based on the amount of traffic you received, and the clicks that came through from them. I’d been a runner for a long time by that point – I’d completed 3 full marathons plus lots of 10Ks and 5Ks – and I knew some HTML coding, and I thought to myself, “I think I can do this.”

There were a few prominent websites at the time devoted to marathon running, but none specifically to the half marathon. I looked up what I thought would be a good domain name (www.halfmarathons.net) and it was available, so I bought it. Then I got to work on building the site, spending the next few years working on it here and there, always on the side of my day job. (At the time, I worked in UX design and later for The Weather Channel’s weather.com as a content developer and writer/producer.)

🥁 START

Why and how did you decide to start The Half Marathoner newsletter in the first place?

Fast-forward about six or seven years, and the website is doing really well attracting traffic, especially (as luck would have it) the half marathon distance became one of the most popular distances in the running. So, searches for it shot up, which made traffic to my site go way up as well.

Then, I had a couple of experiences that made me very wary of relying only on Google traffic; once, I had some problems with the website hosting company and my site went down for an entire day. That really freaked me out! A few months later, Google suddenly and without warning marked my site in their search results as “unsafe,” which made traffic plummet. They removed the warning within 24 hours, but it really put a scare in me.

Around that same time, I’d become aware of newsletter companies like TheSkimm, which were all email – I thought, that’s genius.

I never saw the newsletter as anything other than a promotional vehicle for the website for the first 3 years I wrote it. I used it mainly to send traffic back to the site, that’s really what my primary focus was. 

But after a few issues, I realized that I needed something to introduce the newsletter with, a brief essay, or even just a few paragraphs that ease the reader into each issue. When Apple introduced its Apple Watch for the first time, that’s when I realized I had something new to say, and I wrote about it – its implications for tracking our personal health, and what that might mean for the future. I just kept doing it after that, and those brief essays got longer and longer, and today are the heart of the newsletter.

Then, I stumbled across Substack and got the chance to talk by phone with Hamish McKenzie, one of Substack’s co-founders. He told me about the subscription model they were looking to put into place and some other newsletters that were using it.

At first, I switched to Substack because they didn’t charge you to send out a free newsletter; my Mailchimp bills were reaching $300 to $400 a month by then. So, that I could send out a newsletter for free was attractive enough to switch.

But, once I was there, I decided to give the paid subscription tier a go. I had made some money from advertising when my newsletter was on Mailchimp, but it was a fair amount of effort to find advertisers, create products for them, and then follow up for payment. It was a manual, time-consuming process the whole way through. With Substack, their payment options made it super easy to earn money from a newsletter, so I decided to try it out.

🚀 GROWTH

How did you gain your first 1,000 subscribers?

It’s important to point out: this is a really unfair advantage I had, as about 20-30 people (sometimes more) signed up for my list every day, and I didn’t have to do anything to find them. They were searching for information my site offered, and it ranked highly in Google’s search results, so that’s how they came to me.

Which growth channels do you mainly use currently?

Right now is very different for me than any time before about a year ago, as I sold my Half Marathon Guide website in the summer of 2022.

The reason why I sold it is that, after 16 years, I had created something that was wonderful in so many ways, but also was a LOT of work to maintain and update. I had help doing it – a pair of great people made regular updates – but still, that there were literally thousands of half marathons that needed updating all throughout the year was a big maintenance headache. I had all kinds of information on each race, and when they changed the route, or changed the price, or changed the start time, etc., each needed to be updated. Now, multiply that by around 2,500 races in the U.S. alone, and you can understand the size of the maintenance work involved. 

 🔄 ENGAGEMENT

You exclusively offer The Half Marathoner’s Strava Club to paid subscribers and host Open Threads on Fridays. 

In addition to the online effort, you recently organized the first subscriber meet-up and run the Richmond Half Marathon together, which sounds amazing! 

How did meeting offline with a dozen of your readers feel?

I loved doing it.

Honestly, I was a little nervous going into it; the subscribers and I who met up had really only connected through the newsletter comments, so what if they didn’t like me, you know? But every single person who came was absolutely delightful, and I had a ball meeting them and getting to know them better. About a dozen or so attended, which floored me – people got on planes or drove hours to come and run this half marathon with me! We had dinner together the night before the race, met at the finish line after, and had a group text going throughout the weekend.

It was so much fun, and I plan on doing it again in the spring, this time on the West Coast.

These online and offline efforts enhance engagement, fostering a sense of community. Obviously, your niche provides a convenient foundation for community-building, but your success lies in how effectively you cultivate it. 

What insights have you gained on fostering a sense of community spirit and sustaining reader engagement?

Thank you so much for saying that!

I had a really good model for the kind of community I’ve built with the newsletter – I should actually say we’ve built, as I think the subscribers are equally co-creators of it with me – from a running group I was a part of several years ago. A group of friends and I would get together every Saturday morning to train for a half marathon, which took about 3 to 4 months. We almost never missed those training runs, and it was always so much fun seeing them and catching up while we ran – and for breakfast and coffee after, when we’d spend another hour or so talking and hanging out.

Running the Richmond Half earlier this fall, our first in-person event together feels like the start of something that I hope will continue and build on itself. It was a ton of fun, and running gives us something that brings us all together.

💸 MONETIZATION

It is not easy to build a paid subscription strategy. Let’s talk about how you crafted yours.

How many paid subscribers do you have? How was the evolution of the number of paid subscribers?

As of today, just over 660. That number has gone up and down over the years; the most I’ve ever had at one time is just over 820. I experienced a drop during Covid, a significant one, obviously. (No races were being run then, so it was an easy expense for people to cut.) But then, new people subscribe, and others continue to subscribe year after year, which makes me feel incredible and honored. 

Finding new paying subscribers is never easy; I’ve tried to figure out what is the right mix of content that encourages people to become paid subscribers, and to be honest, I haven’t come up with anything that suggests a pattern. I think with my newsletter, when people are ready to go paid, they’re ready. It probably takes subscribing for a while and getting to know me, my work, and the community before people are ready to take that next step. 

I time them around holidays; the end of the year and January 1 are always key times for signups. I do them about once a month, or every other month or so. Every so often, I’ll send out an article that will attract about 3 to 5 new paid subscriptions, but that’s usually about the maximum number of new paid subs I receive when I send out a newsletter – often, it’s zero.

When did you decide it was the right time to start a paid subscription? How did you validate that your readers were ready to pay?

Do you have any recommendations on when and how to start?

If memory serves, I had around 35,000 on my mailing list when I first moved it over from MailChimp to Substack. It grew to just north of 55,000 by the first half of 2020, and then gradually has dropped off since then. I’ve had two times when I made big cuts to the list, removing subscribers who were no longer engaged. (I cut about 3,000 the first time and 5,000 the second time.) And usually about 20-30 people unsubscribe with every free email I send out; I’m at just over 42,000 now.

Honestly, I didn’t validate that they were ready to pay. I just tried it. When I sent out the email letting readers know they could sign up for a paid subscription, it was mid-2018. Substack was less than a year old, and the concept of paying for an email newsletter was still early then.

Most of what I’ve tried have been things I’ve seen other writers do, and publications like the NYT, WSJ, Washington Post and others. Some people frown on offering discounts and trials, with the thought being that discounts train readers to undervalue your work. But there’s a reason the big publications use them frequently – they give readers on the fence an easy on-ramp to try you out. 

I’ve seen some writers wait years (like I did) before turning on paid subscriptions, and others start with them right out of the gate when they start their newsletters. I can definitely see logic in waiting, as it gives you time to establish a relationship of trust with your readers and prove that you’ll deliver what you say you’re going to deliver.

If they know you well from another venue (like a Twitter or Instagram feed you’ve published for a while) and have a relationship with you from that already, or if you’re an established writer from another publication, I can see turning on paid subscriptions earlier rather than later.

Otherwise, I’d give it at least some time – for yourself as much as your potential paying readers, to find out if you really want to do this, if you can commit to the schedule a paying newsletter requires.

There are some newsletters that publish at random times, and others that publish monthly or even less frequently, and have thousands of paying subscribers. They’re usually already famous or have very well-established social media profiles that serve as their on-ramp for new readers/subscribers. Consistency is going to be key, especially when you’re starting out.

How do you set pricing?

Originally, I priced it at $6 a month, and $60 a year. That felt too high, so I reduced it to $5 a month, and $50 a year. That’s what Runner’s World charges for their paid subscription, so it felt okay to anchor my price to theirs. I’ve toyed around with higher and lower prices here and there, but never really strayed very far from the $50 annual price. That seems to feel right. (Though I’ll probably feel differently a week from now, and wonder if I should change it.)

How do you differentiate the content that you offer free and paid subscribers? 

That’s something I’ve gone back and forth on over the years; right now, I have settled on a weekly free essay that goes out to everyone, a Friday discussion thread that sometimes is for everyone and sometimes only for paid subscribers, and a Sunday issue that’s for paid subscribers only, with races I’ve found and recommend, plus my curation of articles, tips on running, podcasts and anything else I’ve found interesting in the world of running that week. I usually write a brief essay at the beginning, too; some paid subscribers read only that and never the weekly free essay, I know. Others love the essay and not the recommendations email, while others like the Friday discussions the most. It’s hard to pin down what “works,” because different subscribers like different things about it.

I hope, at the end of the day, that the whole is greater than the sum of its parts, so to speak – that it’s an experience for subscribers that’s personal, encouraging and fun, and inspires them to get out and run. 

What is your strategy to acquire new paid subscribers? How do you turn free readers into paid ones?

Um…. this is very much a work in progress!

I’ve recently started investing more time into Pinterest, as I often find myself drained by the reverse-chronological social media feeds we all know at Twitter, Instagram, etc. I do like Threads, and I’ve been spending some time there posting and interacting (and, Threads has generated a number of free and at least one new paid subscriber, so that’s encouraging).

I’ve also reached out to some of the companies that organize races, and arranged for an ad to be placed in their “virtual goody bag,” which is an email a race sends out to all their runners about a week before the event. This one went out to about 10,000 people, which is great. I need to do a lot more of that, I think.

📩 E-MAIL SERVICE PROVIDER

Why did you choose Substack? Pros and cons?

At the time I joined, there were no real competitors to what Substack was offering, except maybe TinyLetter. But they were only email-based; Substack, even then, offered a web version of your newsletter, so you had a website and an email in one. 

The rise of competitors to Substack since then hasn’t escaped my notice; I see what Beehiiv and Buttondown and Ghost and others are doing. Still, none of them have the complete package that Substack has in terms of being able to easily turn on paid subscriptions and build a community with your readers at the same time. I’ve always said that comments and discussion threads are Substack’s killer feature; it stuns me that it took as long as it did for Beehiiv and Ghost to make them standard parts of their product offering for newsletters. 

I should also say, Substack has been very kind and helpful to me personally. They’ve invited me to be on a panel and to be part of their Writers League, and they’re always unfailingly kind and helpful whenever I reach out with questions. They’re personally just great people to work with. 

The cons?

There aren’t many, though I wonder sometimes if there might be better tools for what my newsletter is. That doesn’t mean I think Substack should change what it offers just because of me; I really think they’ve created a great offering for writers to build a community around their work. I think it’s because I’m in this really hyper-specific niche, I just wonder sometimes if I’m trying to fit a square peg into a round hole. (What I do isn’t the kind of writing most writers on Substack do, so that’s why I sometimes wonder if I’m the “one of these doesn’t look like the others,” you know? Still, this is really nit-picking; I have no plans to leave, and I’m happy there.)

🧩 SYSTEM & PRODUCTIVITY

What does your typical week look like when considering the whole process, from creating to distributing a weekly newsletter issue? 

How does panicking the night before sound?

In all seriousness, I start putting together the paid Sunday issues a few days ahead of time, so I can collect the things I want to include and make sure every paid subscriber issue is a home run.

I want everyone who reads it, free or paid, to feel like it’s worth their time, but I especially want paid subscribers to feel glad they’ve become members and that every paid issue is great. 

Discussion threads, I kinda put my finger in the wind to feel what’s of the moment, you know? Sometimes they’re timely, sometimes they’re not, they might just be something I have a question about and wonder what other readers think. I wing it more with those.

🎢 NEWSLETTER EXPERIENCE

How did building The Half Marathoner contribute to your life professionally and personally?

It’s been a huge, huge gift to me personally. To know that my writing reaches people, that it moves them, and that they’re inspired to go run a race because I suggested it or I at least helped them find the motivation to do it.

As far as professionally, it’s different from my day job so it doesn’t really help me build that career necessarily, but I like having a few different things to do – I like the variety, I like the challenge. That anyone wants to read what I write is still awesome to me, and I’m glad what I write is something that isn’t divisive or polarizing. Writing about politics on Substack would probably be a much bigger money-maker than what I’m doing, but I imagine it would turn me into a person I don’t want to become.

What is the most challenging part of writing a newsletter and how do you handle it?

I thought I’d say sticking with it and being consistent, but that is less of a challenge for me now. After almost 9 years of doing this, I’ve more or less built this habit into my life and it’s hard to imagine what it would be like to not do it. 

There is most definitely a trough of despair you have to cross, in which you don’t know if what you’re doing is working or not; I won’t tell you to blindly persist, because if you think it isn’t working, you might be right! That’s what I struggle with the most – should I take the newsletter in this direction or that direction, would that make it more successful?

But then I have the challenge of, when I sit down to write, what comes out is what comes out – I’m not really in charge of that. There’s some other part of my brain that’s not under my conscious control that decides that. I think that’s just the way I’m wired.

Can you tell us one mistake and what you learned from it during your newsletter journey? 

If you can’t name a mistake, let me ask this instead: What would you do differently if you had a chance to start your newsletter journey over?

I’ll start by sharing something that I actually don’t think was a mistake, necessarily, though it did cost me quite a few paid subscribers.

In the spring of 2021, I told my readers I wanted to branch out and write about things other than running, that I was kinda done with it. Lots of readers were incredibly supportive, but others were like, “that’s fine, but I’m not paying for that – I came to you for this other thing. You’re not doing that anymore, so I’m out.” And I can’t blame them for that at all.

I probably could have handled it better – maybe by not announcing it! Because I already was writing about subjects tangential to running, or things that were related to running but not in the “strike zone” of training, preparing, etc. (I’ve always felt there’s so many other places to get that information, so I need to offer something else, you know?) So, there’s a lesson in that experience.

I wrote what felt natural to me, and about the things that lit me up, and I get why that might seem a little all over the place to a reader.

I was recently listening to an interview with Matt Brown of the Extra Points newsletter, a newsletter about the business of college sports, and one thing he emphasized is that he thought about monetization from the very beginning of his newsletter. I never thought about that! I just got going on it, and wrote what felt right that week. I probably should have thought it all through a little more.

📌 RECOMMENDATIONS

What would it be if you had the right to give one piece of advice to aspiring newsletter creators?

Are your readers going to come from social media, like X or Instagram or Threads? That’s going to mean you’ll probably need to be “present” on those networks in a way you wouldn’t have to if you’re going to attract readers via search like Google and Pinterest, where your links or pins just sit there, waiting to be found.

Or, are you going to be found by partnering with other newsletters? That can be great too; I know of other newsletter writers who’ve found a lot of success by being featured in other newsletters.  

What are your favorite newsletters that you can’t wait for the next issue?

• Mike Sowden’s ‘Everything Is Amazing’ – his enthusiasm for writing about (amazing) science stories is so infectious. He’s also someone I think of as a friend, as we’ve had the chance to meet and talk over Zoom, even though we’re separated by an ocean. (He lives in Scotland.)

• Clara Parkes’ The Daily Respite – I almost never miss it.

  Sean Dietrich’s Sean of the South, every day is so, so good.

  Scott Hines’ Action Cookbook is fantastic!

  Anne Helen Petersen’s Culture Study, Katie Hawkins-Gaar’s My Sweet Dumb Brain, both are just awesome.

  Liza Donnelly’s Seeing Things and Nishant Jain’s The SneakyArt Post are also both wonderful.

• In running-focused newsletters, I love Sam Robinson’s Breakfast Club; it’s always a great read from which I get something.

  Raziq Rauf’s Running Sucks newsletter is great as well. 

👋 FINAL WORDS

Appropriately, maybe, I don’t have any.

Thank you so much, Terrell!

🔗 Where to find Terrell Johnson and his work

• Instagram

• Twitter / X

3 Popular Issues from The Half Marathoner

1. ‘A Small Good Thing,’ which I wrote in response to the Uvalde, Texas, school shooting. It has nothing to do with running, but I couldn’t not write it.

2. ‘Aristotle’s Way,’ which I wrote about making progress as an athlete through the eyes of my (then) 9-year-old

3. ‘Do You Hear What I Hear,’ about hearing loss. Again, not about running, but one I couldn’t not write.

👉 Do you want to reach 1,700 newsletter creators & enthusiasts?

That’s all for today. Thanks for reading and don’t be shy to hit reply if you want to reach out to me.

See you on Wednesday.

Ciler