How David McIlroy Built a 34K-Subscriber Writing Business on Substack

He Almost Quit Substack After 5 Months. Then Everything Changed.

This is an interview with David McIlroy of How to Write for a Living and The Solopreneur Stack.

At a glance:

• Current subscriber count: 34k~

• Most successful post: How I grew my Substack audience by over 1,400 subscribers in under 2 months

• Most underrated growth tactic: Substack Lives

• One creator everyone should follow: Too hard to pick just one!

• One tool you can’t live without: Canva

• Key metric to track: Depth/quality of comments on your content

• Main revenue source: Coaching

• One sentence describing your newsletter: Writers deserve to get paid.

• One piece of advice for new writers: Make close friends in your online space and support each other without expecting anything in return.

The Beginning

Tell us about your publication. What do you write about and who is it for?

How to Write for a Living is for creators who want to build sustainable income from their writing without burning out or chasing viral moments.

I write about growing an audience on Substack, launching paid subscriptions, creating products people actually want, and building a business that lasts. It’s for people who are serious about turning their writing into a living, not just dreaming about it.

What was your writing journey like before Substack?

I have an MA degree in English but I didn’t do anything significant with it until 2018 when I started taking on some freelance writing jobs. I wrote blog posts, website copy, social media content, that sort’ve thing.

Then in 2020, I started writing my first fiction novel, The Soulburn Talisman. Four books later and I’m almost finished with the draft of my next horror novel.

During that time, in 2023, I joined Medium and began posting there on a regular basis. Later that year, I discovered Substack and it quickly became my main platform.

What made you start on Substack in the first place?

I’ve heard about it for years but didn’t pay it much attention initially because I was more focused on Medium.

Once I got my first paid sub on Substack and realised I could build something real there, my focus changed.

What did your first few months on Substack look like?

Growth was slow, as you might expect. I only grew by a couple of hundred subs in the first five months. But then Notes really exploded and my growth accelerated massively from December 2023 onwards.

Keeping at it during the slow period is so difficult, but very much worth it when you’ve pushed through.

At what point did you realize this could become something bigger?

That first paid subscriber, and then the abrupt change in my audience growth rate.

The Growth Story

Can you walk us through your subscriber growth journey?

I joined Substack in June 2023 with 49 subscribers imported from another platform. For the first five months, growth moved at a snail’s pace.

I hit 187 subscribers by the end of November and honestly couldn’t see how I’d ever make the platform work in a meaningful way. Then December happened. I rebranded from #AmWriting (an accidental rip-off of a much bigger publication) to How to Write for a Living, and I started taking Notes seriously.

By New Year’s Day I had over 900 subscribers across my publications. By June 2024 that was 8,154. And in July 2024 I crossed 10,000, a threshold I never expected to reach.

What were the biggest growth drivers?

Notes has been a significant driver - it’s where a lot of discovery happens now.

Collaboration too: guest post swaps, recommendations, Substack lives and genuine relationships with other writers rather than transactional DM exchanges.

What’s one thing that worked much better than you expected?

Engaging directly rather than just producing content.

For a long time I was a producer - I’d write, post, and wait for people to come to me. When I flipped that and started getting into the comments, sharing other people’s work, and having real conversations, opportunities started coming out of it.

Not just more subscribers, but podcast invitations, Substack Lives, and coaching clients.

The conversations turned out to be worth more than the content.

What’s something everyone says to do on Substack that didn’t work for you?

Promoting my Substack on other social media platforms.

I was locked into Twitter and the rest, assuming that sharing my writing there was the smart approach. It wasn’t. The growth was on Substack itself the whole time.

Once I stopped whispering into the void elsewhere and put that energy into Notes, comments and connecting with writers in my niche, everything ticked up.

If you had to start from zero tomorrow, what would be your first 30 days strategy?

If I started over, I’d lay more groundwork before trying to sell anything, and I’d get clear on exactly who I was writing for from day one.

I’d focus less on producing volume and more on genuine engagement - spending time in other people’s comments, building real relationships, and giving people a reason to be curious about me. And I’d start building an email relationship immediately rather than treating subscribers as a number.

Behind the Scenes

What’s your content creation process like today?

At its core, it hasn’t changed much. One substantial article a week, Notes every day, and a rule I set early on: refine the process by 1% each time.

I also read a few posts from other writers daily, partly to learn and partly because engagement is half the job.

The other big piece is community. Chat threads, questions at the end of posts, conversations in the comments. That feeds back into what I write next, because I actually know what my audience wants now.

How often do you publish, and how did you find that rhythm?

At least one article a week, at least one Note a day.

I found that rhythm by setting goals that were entirely within my control. I had hopes about subscriber numbers and recommendations, but those were soft goals. If I missed them, it didn’t matter.

Publishing weekly and showing up daily were things I could actually do regardless of how the algorithm felt about me. That’s what made it sustainable. Short bursts of enthusiasm fizzle out, but habits don’t.

What metrics do you actually pay attention to?

Engagement more than raw subscriber count. Likes, comments and restacks, and whether they’re consistent across all my content rather than one lucky post.

The real gold is watching subscribers engage with each other, in the comments and in chat threads. That tells me a community is forming, and community is what keeps people subscribed.

I deliberately don’t obsess over the numbers outside my control. I track what I can do, and let the graph take care of itself.

What was the biggest mistake you’ve made on Substack?

Not taking it seriously for the first five months. I treated Substack as just another string to my bow, among many other fairly pointless strings. I didn’t invest real time in it. I repurposed content from Medium, published inconsistently, and wondered why nothing was happening.

When I finally treated my publication like a business, with plans, targets and things I could measure, the line on my subscriber graph curved upwards after months of plateau. The platform was never the problem - my effort was.

Was there a moment you almost gave up or seriously questioned what you were doing?

The end of November 2023 was probably the lowest point. Under 200 subscribers after five months, posts getting little or no engagement, no real feedback to go on.

I genuinely couldn’t see how I’d ever make things work. And even now, slow days still happen.

I posted a Note last summer that just said I was feeling low energy and disheartened, and it resonated with hundreds of people. That’s the honest answer.

The doubt never fully disappears. You just build habits strong enough to carry you through the weeks when the motivation isn’t there.

The Business Side

Has your newsletter led to opportunities beyond subscriber growth?

Massively. It’s led to coaching clients, a paid community (Catalyst Club), a podcast, guest collaborations, Substack Lives, and joint ventures with other creators.

A lot of these came from conversations rather than any deliberate funnel. The newsletter is the top of everything, but the real opportunities have come from the relationships around it.

What role does your newsletter play in your overall business ecosystem?

It’s the hub. Everything connects back to it. The free content builds trust and discoverability, which feeds into the community, the coaching, and the products.

It’s where people first meet me, and the rest of the business is what happens when those relationships deepen.

You run 3 publications. What’s the thinking behind separating them instead of building one strong brand?

Clarity, mostly. I learned that lesson the hard way when I rebranded my main publication from #AmWriting to How to Write for a Living.

That one change added so much clarity for potential subscribers. They knew exactly what they’d get in exchange for booping the subscribe button.

The same logic applies across publications. Someone who wants help building a writing income doesn’t necessarily want my horror fiction landing in their inbox.

So How to Write for a Living does what it says on the tin, The Solopreneur Stack covers the business side, and my fiction lives separately. Each audience opted into a specific promise, and I try not to muddy that.

How do you decide what content goes where?

I go back to what each subscriber signed up for. The question I ask is simple: did this person subscribe for this?

If I’m writing about growing a publication or making writing pay, that’s How to Write for a Living. Business and solopreneur territory goes to The Solopreneur Stack. Stories go to the fiction pub.

When something could fit in more than one place, I think about which audience gets the most value from it, and I’ve become increasingly aware of exactly what each audience wants from me and how they like to receive it.

That knowledge came slowly, mostly through comments, chat threads and watching what resonated.

What kind of content actually converts readers into paid subscribers for you?

Guidance content with real substance behind it.

My paid tier works because the free content piques interest and proves I know what I’m talking about, then the paid side goes deeper: the full breakdowns, the Member Resource Hub, the private community for paid subscribers.

The framing I always come back to: people follow when you pique their interest, subscribe when you offer value they can’t find elsewhere, and stay subscribed when they feel part of something.

Paid conversion sits on that last bit. My first paid subscriber came as a genuine surprise in October 2023, and my free-to-paid ratio stayed low for ages purely because the free base grew so fast. The paid side caught up as I added more depth for members.

What surprised you most about the behavior of paid subscribers compared to free ones?

How much they engage with each other, not just with me.

I expected paid subscribers to want more content. What they actually wanted was more connection.

The chat threads, the private community, the conversations under posts where they’re advising each other and subscribing to one another’s publications. That’s where the magic happens.

What’s Next

What’s your goal for the next 12 months?

Keep growing my audience (in terms of depth as well as numerically), simplify my process even further, and invite more members into my group coaching programme.

What are you currently experimenting with?

I’m always tweaking my approach to podcasting and video, as well as the way I construct articles and how I promote my offers.

The biggest experiment is with my group coaching programme, which is just about to launch. It’s new territory, to an extent, so there’s going to be some trial and error in there.

The shift toward direct engagement and relationship-building over pure content production. Using DM outreach and comment engagement to find the right people rather than waiting for them to come to me. I’m also running more collaborative events, like joint masterclasses with other creators.

Where do you think Substack is heading as a platform, and what opportunities do you see opening up for creators?

I’ve said before that we’re in the early days of Substack’s explosive era, and I still believe that.

It’s going to get bigger. More people will join, and readership opportunities will increase with them. But I’m not naive about it. Times change, platforms change. The powers that be make bad choices, and unbroken things get fixed and consequently made worse.

Just ask anyone who’s been on Twitter for more than a couple of years.

My organic growth could fall off a cliff overnight. That’s exactly why I tell writers to treat their publication like a business rather than a hobby that happens to live on someone else’s platform.