Two Kinds of People Read This Newsletter

(besides my mom...)

I started this newsletter to write about what actually happens behind the curtain of growing companies.

Not the highlight reel.

The actual, messy, three-Slack-threads-deep reality of it. I am incredibly grateful that there are over 4,800 of you here sitting in the mess.

Over time, I realized there are two groups in that 4,800.

The founders living through the chaos.

And the operators helping them clean it up.

Where that’s already showing up

I didn’t plan for both of you to be here, but looking back, it makes complete sense.

More than one founder has read this newsletter, kept reading, ended up on a call with me, and eventually hired me. That part has worked exactly the way I hoped.

But a LOT of you reading this are not the founder.

You’re the operator. The fractional. The generalist. The person someone calls when the company has somehow created four onboarding processes and no one knows which one is real.

You’ve been here the whole time.

I just haven’t been building enough specifically for you.

What stays free

The free newsletter will keep being a place where both groups can see themselves.

The founder still deep in the chaos.

The operator who can already see why the chaos keeps happening.

That is the whole point of Systems & Side Eyes. I’m not changing it.

What’s changing about the paid tier

Here’s the part I’ve been sitting on.

I have an entire Google Drive full of templates, prompts, meeting structures, scripts, and operating tools pulled from real client work.

Built for real problems.

Used inside real companies.

Currently collecting digital dust until I happen to need them again. Very efficient system I have created here.

So the paid tier is becoming The Operator’s Back Room.

This will not be a second set of essays.

It will be the actual stuff I use to do the work, along with the context that makes it useful:

The Notion homebase I set up when company information is living in seven different places.

The meeting cadence that ends the “we need another meeting to discuss this meeting” cycle.

The ownership structure I use when every decision still floats back to the founder.

The scripts, prompts, and frameworks that help turn vague frustration into a problem someone can actually solve.

One tool at a time. Plus when to use it, how to adapt it, and where it tends to fall apart.

What this is NOT

This is not a course about becoming fractional.

It is not a coaching program.

I am not going to stand at the front of a virtual room and pretend I have discovered the one correct way to build a portfolio career. (The internet has enough people doing that.)

I am opening up the systems I use to do the actual work.

I know how to walk into a growing company, find the friction, get people talking to each other, and build structure that does not immediately get abandoned.

That is what belongs in the back room.

What opens first

The first resource is coming next week.

I’m deciding between:

The Notion operating homebase.

The meeting cadence structure.

The RACI-lite ownership template that helps get decisions out of the founder’s head.

If you are the operator, fractional, or generalist holding everything together for someone else, reply and tell me which one you would use first.

Paid subscribers will get the winner first, along with the walkthrough for how I actually use it.

Founders are welcome in the back room, too. You may not want to build every system yourself, but you might want to see how I approach the problems happening inside your company.

Either way, the free side is staying exactly where it belongs.

Behind the curtain. Looking at the mess. Occasionally side-eyeing the fourth Slack thread.

More soon.

KB