After 53 Newsletters, One Thing Became Uncomfortable

In partnership with

Hello Athletic Entrepreneurs.

I’ve been reflecting this morning.

My first newsletter went out on November 29. As of today, I’ve written 53 newsletters in just over two months.

That number matters—not as a flex, but as a signal.

This is my first time building a newsletter. I’m not optimizing yet. I’m not scaling yet. I’m learning—through repetition, not theory.

One thing has already become clear:

I like to write.

I like preparing material.

I like thinking through ideas.

I like being verbal about my experiences.

And I enjoy using AI as a copilot—an editor, an assistant, a thinking partner.

Early on, volume isn’t noise—it’s reps.

I’m currently at 335 subscribers with an estimated 32% open rate. I treat that number carefully. Open rates are imperfect. Some opens are automatic. Some people I know personally haven’t read certain issues even when analytics suggest otherwise.

So I don’t obsess over it.

What I care about more is learning how engagement actually forms.

One thing I’ve had to accept quickly:

You can’t build this on family and friends.

They’re supportive, but they’re not the market. There are 8 billion people in the world. Growth requires going out and finding your audience—not waiting for familiarity to validate the work.

That’s a lesson every creator eventually learns.

There’s more to AI than ChatGPT.

If you’re only using AI to rewrite emails, you’re doing it wrong.

The AI for Business & Finance Certificate from Columbia Business School Exec Ed breaks down how to use AI to make faster, more strategic decisions at work.

Save $300 with code SAVE300 + $200 with early enrollment by Feb. 17.

Enroll Today

To do that, I need feedback loops. That’s why I’ll be using polls more intentionally—not to chase approval, but to understand where interest naturally clusters. I write about sports, basketball, entrepreneurship, AI, and personal experience. Not everyone will care about everything—and that’s not a problem.

That’s data.

I also tested an e-book. Only two people asked for it.

That didn’t discourage me. It clarified timing. Trust comes before transactions. This is still early.

I’ve lived this process before.

When I first started shooting a jump shot, it looked terrible. My mechanics were off. The confidence wasn’t there. If you judged the shot in the first few months, you’d think it wasn’t going anywhere.

But repetition changes things.

The release smooths out.

The decision-making speeds up.

The polish comes from reps—not intention.

This newsletter is no different.

That’s why ownership matters to me. Writing here builds a direct line—something no platform can deboost or take away. Especially as I rethink how much energy I give to social media, this feels like the right long-term investment.

This isn’t discouraging.

It’s calibration.

If I write another 50+ newsletters over the next couple of months while improving engagement along the way, that’s progress. If this grows to 10,000 subscribers one day with a 30–40% open rate, that’s success—because the foundation was built properly.

This is still the early reps.

So I’ll keep writing.

I’ll keep learning.

And I’ll let repetition do what it always does.

Just like it did with the jump shot.