The $300,000 Lesson

I once watched a founder spend about $300,000 over two years on his first operations hire and get absolutely nothing out of it. No scalable systems. No measurable improvement. No organizational adulthood.

I know because I was that hire.

There are certain business problems so common that people stop treating them like problems and start treating them like a fish treats water.

Meetings multiply. Decisions stall. Work slows down like a traffic jam; nobody is technically "stopped," but nobody's really moving either. The founder, once formidable and free, starts looking like a referee, flagging on the sidelines of his fourth consecutive game today.

At some point, the founder tells a friend: I need an ops person.

It's the same way someone says I need to start running, or I need to drink more water, or I need to stop eating like a raccoon.

It's not because they have a detailed plan, but because the phrase is a kind of prayer and feels like a moral victory. It also implies maturity, responsibility, a willingness to do things "the right way," and a sense of having "arrived." It suggests the founder is graduating from scrappy to serious.

It also usually means they are drowning. You don't cry "Ops!" when things are running smoothly.

But if you're about to make your first operations hire, there's a two-part question you should answer before you post the job description, before you call your network, before you offer someone a salary that makes them feel both honored and vaguely doomed:

How do you want your business to run, and how is that different from how it runs today?

The answers determine whether your ops hire becomes leverage… or a $300,000 lesson.

This sounds like a tragedy, and it was. But it taught me the most important lesson of my operations career:

Ops can’t scale what you haven’t made real.

The founder wants relief. They want a change in the system. And they want it without changing.

This founder had the kind of early success that feels less like progress and more like permission. Customers showed up. Revenue arrived. The market responded warmly enough that he began to experience the distinct emotion of modern entrepreneurship: I am right, and I will win.

But he was in a competitive space. Plenty of other companies sold similar products and outcomes. He knew he couldn't outspend them or out-brand them. What he believed he could do was out-operate them.

He wanted to win on the boring stuff:

Speed. Consistency. Quality. Responsiveness. Less chaos. A better way of doing things.

He wanted what every founder says they want: systems.

So he did what founders do when they develop the suspicion that they are no longer the perfect tool for every job:

He hired.

He hired me.

We'd worked together before. He trusted me, and I had what people generously call "systems instincts" (the ability to look at messy workflows and pull out the thread that actually works).

He made a generous offer. Strong salary. Autonomy. A free hand to shape "how we do things." The whole thing carried the warm, optimistic tone of early architecture: We're going to build this right. No operational debt. No chaos.

I accepted. There were hesitations. He could be intense. Some founders have an owner's relationship to the business. This one had a nervous system relationship to it. He cared. He noticed. He intervened. He had opinions about details other people didn't know existed.

But this was a great opportunity.

What followed was painful for both of us.

I started well, I think.

I observed. I listened. I mapped work. I asked questions. I tried replacing the oral tradition with something written in black and white. I proposed rhythms, frameworks, systems. I wrote things down.

And then the business did what businesses do under pressure.

It bucked.

A customer needed an exception. A deadline slipped. A manager skipped onboarding. A teammate ignored the new intake form. A deliverable needed judgment.

In these moments, operations either becomes real, or it's proven fake.

When operations is real, the system holds. It might be imperfect, but it constrains reality enough to produce consistent results. People follow the process because it's the path of least resistance and because leadership has shown it matters.

When operations is fake, the system collapses into a familiar shape:

Everyone looks to the man at the top.

The founder looked at the process, looked at the decision, and did what founders do when they’re comfortable with control and they fear being wrong: he overrode the system.

He just stepped in "real quick."

Not maliciously. Not flamboyantly. Not out of ego. He was solving the today-problem — which felt great. It felt like competence. Leadership. Velocity.

And it taught the company something extremely important:

The system is optional. The only real system is the founder.

I noticed the pattern and tried to go with it.

I would propose a rule based on data, or streamlining delivery, or even the founder's previously expressed preferences. He'd agree. Then something would crop up. He'd override.

I would propose a decision boundary. He'd nod. Then a real decision would arrive. He'd step in and relitigate.

Within a few months, I was a well-compensated human notebook.

Documenting what he’d already decided. Trying to make operational excellence out of exceptions. Building architecture that was constantly undermined by the person who wanted and needed it most.

He felt disappointed. I felt crazy.

In hindsight, I now know there were a million ways I could've seen and addressed the pattern we found ourselves in. A million ways I could've been more helpful to both of us. Instead, I left for another job.

In the immediate aftermath of my departure, I think we both thought the other was missing something obvious. Back then, I would've said the issue was that he wouldn't let go. Now, with time, I realize the truth: there was nothing to let go of. There was no shared structure to shape or debate or improve.

He had, in effect, hired someone to install an operating system on a computer that didn't have any hardware inside — and like a crazy person, I was actually trying to do it.

When founders hire their first ops person, it's usually because they're drowning. Their week is a collection of interruptions. Their attention is shattered. The business is productive, but only because the founder is constantly patching leaks, pulling boards together fast enough to keep everything from going under.

They want someone to build a better raft.

This is the right instinct.

But you can't use your first ops hire to build the raft while you're both still in the water.

If the business is afloat only because the founder is swimming underneath it, keeping it up with their own lungs and legs, using primarily his own instincts to adapt in real time — then you don't have a raft.

You have a founder-shaped flotation device.

And if you don't have a raft, what exactly did you hire?

Someone to swim alongside you with a clipboard?

Your first ops hire doesn't need "freedom."

They need terrain. They need your intent. And they need authority.

Most founders hear that and think I’m asking for paperwork.

I’m not.

I’m asking whether you’ll turn instincts into something actionable: who owns what, what “done” is, and which tradeoffs you’re willing to accept even when you disagree.

Because there are two kinds of founders at this moment.

If you won't name owners besides yourself, if you won't settle decision boundaries, if you won't let go of being "the guy" for every call…

then don't hire ops.

You can still build a great business. Plenty of people do it on taste, instinct, and constant involvement.

But an ops hire won't become leverage.

They'll become a very expensive witness to a truth you don't want to face:

you don't have operations. You have preferences.

If you can define what's already true, even roughly, you're showing the exact muscle ops needs from you.

Not "documentation."

Honesty.

Start here. Three questions. One weekend.

Write the answers down. Not beautifully. Not "enterprise." Just in a way that another adult can read.

That’s the baseline. That’s the terrain.

And if you can do that, your ops hire isn’t swimming beside you with a clipboard.

They’re building something that holds because the business is finally existing somewhere outside your head.