Here's what I learned after 100 posts on Substack

Today is my 100th Substack post for Tracy’s Tidbits.

I started writing about marketing and sales on Substack on May 9, 2024.
I publish consistently every Wednesday.
I restack my own posts (and others) for visibility.
I cross post my content on LinkedIn occasionally when I want to amplify it.
I have 1.1K subscribers and have over 1400 followers.

Here’s what I’ve learned after 100 posts on Substack:

Lesson: Audiences

My first few posts were about how I went from CMO to CRO (hence the URL), which, in hindsight, I should change. (You can change this in Settings under the Danger Zone)

Then I started writing about topics in GTM that I knew well, experiences that I’d had in B2B SaaS and RevOps, and sharing experiments I had tried with AI. I also wrote about job hunting as a CMO.

My audiences are all over the board because of this. I have marketers, agencies, sales folks, founders, CEOs, job seekers, and developers that are subscribers.

Where I went wrong 😑: I didn’t tighten up my themes or my narrative in the beginning.

Now, I mostly write about marketing and sales topics still, and try to cater those topics more toward executives. But it’s still not perfect.

Lesson : Cadence & Themes 🗓️

The cadence piece is not too different from blogging. Create consistency, create themes, and people will subscribe. I mostly write about CMO problems I’ve had myself, and since I’m a full-stack CMO, I talk about everything in GTM. But somehow founders and CEOs still find their way to this Substack.

Lesson: Substack Notes 📝

I tried posting notes thinking it was something like what Twitter used to be - short, pithy commentary. But that fell on deaf ears, so now I post two things:

1. I re-stack my own or other people’s content with a comment

2. I write shorter posts and publish them in-full as a Note.

Lesson: Cross posting content ♾️

When I look at where my subscribers (both free and paid) come from, the majority come from substack recommendations, LinkedIn, or direct.

I almost always cross-post my content on LinkedIn. I view and treat Substack just like any other social media platform. (Something tells me I’ll probably eat those words in the future, but for now, that’s how I am treating it).

Lesson: Imagery matters 📷

Just like it matters in social media, imagery matters on Substack and when cross-posting on other platforms.

I often will create images in Canva or occasionally in AI when I’m tight on time.

I do not use the sharing mechanism that is built into Substack when I share on LinkedIn. Instead I write it from scratch, upload the graphic/image relevant to the post.

Lesson: Monetization 💰

I’ll be honest: at the beginning, I was anti-monetization.

Not in a dramatic, “I hate capitalism” way, but more like, why should people have to pay for content? The whole point of writing, at least for me, was to share what I’ve learned. Gating it felt counter-intuitive.

Then two people paid me anyway without being prompted or pitched or even a paywall. So that forced my hand and made me think, if people were willing to pay without being asked, the least I could do was make it possible and easy for them to do so.

To be clear: I’m not trying to make millions on Substack. That was never the goal. We’re all drowning in content already, and competing for dollars wasn’t why I started writing. I wanted people to learn from my mistakes, shortcuts, and scar tissue.

What really changed my perspective was something small but meaningful. Over the holidays, someone gifted three subscriptions to other people. I was taken aback.

It reframed monetization for me. I started viewing it not as extraction, but more as a signal. A quiet way of saying, this helped me enough that I want someone else to have it too.

Sharing is still the point. Sometimes paying is just how people say “this mattered.”

The real way to monetize (and what’s on my to-do list next): I’ve created a services tab, but I haven’t published it yet. Trying to learn from other’s on that first. What I’ve heard from most other writers so far is that they don’t make money from subscriptions, they make money from monetizing their other services they offer - like a course, consulting, a book. Substack is just another avenue for them to amplify.

The takeaway after 100 posts?

Substack isn’t about hacks, virality, or “finding your niche” overnight. It’s about repetition. Clarity comes from writing, not planning. Audiences shows up after you post. And monetization isn’t something you force but rather something that emerges when the work is useful enough.

One hundred posts didn’t give me a perfectly defined audience, a flawless narrative, or a predictable revenue stream. What it gave me was momentum, signal, and a much sharper point of view. That alone has been worth the consistency.

I’m still learning. Still tightening the story. Still experimenting.
But I’m no longer guessing whether this is worth doing.

It is.

On to the next 100.