I've helped clients build newsletters to 55,000+ subscribers.
But when it comes to my own newsletter?
I keep face-planting into the same wall over and over again.
The Expert Mask Problem
Three years ago, I launched "Client Getting", a newsletter about how to get clients.
The logic seemed solid: write about getting clients, learn how to get clients, actually get clients.
I did learn how to get clients.
But I didn't actually get any clients.
Because the whole thing felt like wearing a costume that didn't fit.
I got up to about 250 subscribers, but quite after issue 51.
Fast forward to June 2024.
I launched "AI Biz Mentor" a simple atomic newsletter featuring AI tools and resources.
Five issues per week like clockwork.
For two and a half months, I kept it up.
By my 45th birthday in August, I was completely burned out.
It just didn't feel right.
After a vacation (my first in years), I let it slide.
I tried to restart it in January of this year.
Sent 14 issues over 7 weeks doing "tool teardowns."
I liked sharing tools, sure.
But I was desperate to write something that actually sounded like me instead of some AI expertise robot.
By February, I was done pretending.
The Thing About Building for Others vs. Yourself
Here's what's weird: when I build newsletters for clients, everything feels obvious.
Cut through the noise. See what's likely to work. Execute.
But when it's my newsletter?
Suddenly I'm second-guessing everything.
The difference?
My clients usually have clear offers.
They know what they're selling and who they're selling it to.
Me?
I've been struggling to get clear on what my core offer even is.
And when you don't know what you're selling, every newsletter feels like you're just... making noise.
Plus there's the psychological weirdness: when you're building for yourself, it's your reputation on the line.
It's you that gets rejected if people don't like what you do.
Starting Over (Again) - But Different This Time
February 28th, 2025: I launched How I AI.
But instead of pretending to be an expert, I decided to embrace being a student.
The strategy: radical experimentation combined with just being myself.
Started with 1-2 semi-structured issues per week.
Then switched to 5x/week personal stories and insights.
Then landed on 2x/week in July (which is where I am now).
The content angle: email marketing and list building, mixing how I use AI with how other people use AI.
I also started this publication at the same time as a space to share the ups, downs and behind the scenes of building my solopreneur business.
Turning Content Into Relationships
Instead of just blasting information into the void, I started featuring other creators in How I AI.
Not as some strategic networking play.
Just because their stuff was interesting.
Turns out, good things happen when you shine a light on other people.
from "Product with Attitude" added me to her recommendations list after I featured her. from "Build to Launch" invited me into a series about builders.Both happened because I wrote about something they posted on Substack first.
The Numbers (The Good, Bad, and Ugly)
Six months in, How I AI is at 260 subscribers.
45%+ open rates, 5% click-through rates.
I started with the 100 or so subscribers I’d gained in AI Biz Mentor.
Others have come from referrals from:
Other Beehiiv newsletters
People finding me here on Substack
Sponsorships in other newsletters
Beehiiv boosts
I've spent $214 on Beehiiv boosts to get 214 subscribers ($1 each). But only 150 are still subscribed, and only 119 have opened at least one email.
Early boosts were trash.
I learned I need to monitor who's boosting me and turn off the ones sending dead subscribers.
Of the people who've opened at least 5 emails (66 people), my real cost per engaged subscriber is $3.20.
Revenue so far: $12.48 from newsletter boosts, $32.02 from ads, $125 from coaching.
Not exactly retirement money.
But I'm treating this as foundation-building, not immediate monetization.
The Breakthrough Moment
Where you start is not necessarily where you end up.
When you're getting started, you don't know what's going to land with others or what you'll be able to stick with long-term, so you have to be open to a lot of experimenting.
You can be bad while no one's looking so you're good when they see you.
But here's what I keep learning the hard way: experimentation has to give way to consistency at some point.
You have to stick with something long enough to see if it gets the result that you want.
The 2x/week format feels sustainable for How I AI.
I’m learning to express th authentic voice that was missing from my earlier attempts here in Unscaled Solopreneur.
I've joined a high-level copywriting mastermind to get clarity on my core offer.
But here's the commitment: I'm done abandoning strategies before they have time to mature.
Because I believe that if I can just be me and share what I'm really doing and experiencing without it being pretentious or put on or faked, then other people who want to learn what I’ve learned or do what I’ve done will follow me and see me and learn from me and eventually start asking me for help.
That was the pivot.
Stop creating a facade of expertise when I didn't have anything solid behind it.
Start showing up as myself, sharing what I'm actually learning and doing.
The current content strategy feels doable.
I've created systems and GPTs to help me do it more efficiently, but I still put effort into it because it matters.
This time, though, I'm not abandoning ship when growth feels slow.
This time, I'm sticking with the fundamentals long enough for them to compound.
Nailed it! This is so true: Start showing up as myself, sharing what I'm actually learning and doing.'' 🤗