Most people give up on hiring after their first serious attempt flops.

They assume, “Well, I guess I’m just not good at hiring.” Or worse, “Good people don’t want to work for me.”

But let’s be honest. Why would your first hire work out?

At that point, most people haven’t hired anyone before. They’ve never managed a team. They’re not even clear on what they really need. They just know they’re underwater.

So they panic-hire. They throw out a vague job post that says something like “Marketing Assistant” or “Operations Manager.” It sounds legit. Corporate. Clean. Like something a real business would do.

And then they hire someone… and it doesn’t work.

Maybe the new hire doesn’t take initiative. Or they do the wrong things. Or they constantly need hand-holding. So the founder gets frustrated and falls back into doing everything themselves.

That’s where a lot of people quit.

They decide that good help doesn’t exist. Or that they’re just bad at managing. Or that it’s not worth the trouble.

I get it. I’ve been there.

But I’ll let you in on a little secret.

In almost every company I’ve ever built, my actual job title has been Janitor.

No, not metaphorically. It’s the job title on the org chart.

Why?

Because 90 percent of my job is cleaning up messes.

Messes from processes that don’t work.
Messes from launches that don’t convert.
Messes from hires that don’t pan out.

Hiring is messy. Especially in the early days of a business.

You don’t need a full-time hire. You need help.
You don’t need a department. You need a result.

What saved us early on and still saves us today is treating hiring like marketing.

You don’t put out one Facebook ad and give up when it doesn’t convert. You test. You tweak. You try again. You gather data. You learn.

Hiring should be the same.

Back when I was starting out, I didn’t write job descriptions. I wrote challenges.

“I need someone to clean up my inbox using this tool.”

“I need a writer to create a blog post from this rough outline.”

“I need someone to update the schedule for our online classes and communicate changes to 20 students.”

Each one of these was a paid test project. Nothing fancy. No three-round interviews or five-year vision questions. Just: Can you do this specific thing?

If yes, we work together again.
If not, no hard feelings.

I’ve done this hundreds of times. And it works better than any traditional hiring method I’ve ever seen.

It’s faster. It’s cheaper. It gets real results.
And just as importantly, it helps you get clearer on what you actually need.

Because that’s half the problem.

Most people don’t know what they’re hiring for. They know they’re overwhelmed. They know they’re tired. But that’s not a job description. That’s a cry for help.

And cries for help attract chaos.

So instead of building a big square hole and trying to find a square peg to fit it, I start with the peg. Then I shape the hole around what works.

Because nine times out of ten, the shape you thought you needed isn’t what the job actually is.

You thought you needed a growth marketer.
What you really needed was someone to optimize a landing page.

You thought you needed an operations manager.
What you actually needed was someone to create a recurring task list in Asana and check in with contractors once a week.

And you only figure that out by doing. Not by thinking. Not by planning. Not by writing a perfect job ad.

You figure it out by testing.

I’ve hired people who ghosted mid-project.
I’ve hired people who delivered work so bad it made me question my own sanity.
I’ve hired people who faked credentials, stole work, and disappeared.

But I’ve also found a handful of incredible teammates, some of whom are still with me years later.

And those wins came because I was willing to go through the mess.

That’s what being a founder is.

You’re not the CEO. You’re the Janitor.

You clean up the messes. You patch the leaks. You figure it out when it breaks.

Eventually, yes, you build systems. Once we had enough successful test projects, we turned those into roles. Those roles became documented processes. Those processes became contracts and onboarding playbooks.

Now, in our Productized Education businesses, we’ve got role scorecards. We’ve got training libraries. We’ve got SOPs. Every new coach, assistant, or admin has a clear outcome and a clear path to success.

But none of that came first.

It came after we ran the experiments.

The same way you wouldn’t write a full curriculum before teaching the first live cohort, you shouldn’t write a perfect org chart before you’ve figured out which tasks actually move the business forward.

The first version is messy. It has to be.

And that’s okay.

Because in Productized Education, your team is your Fulfillment engine.

They’re the ones responsible for delivering connection, clarity, and accountability, which is your real product.

If the wrong person is teaching, your students don’t get clarity.

If the wrong person is doing support, your students lose connection.

If no one is tracking outcomes, your students lose momentum and quit.

Hiring isn’t just an admin function in Productized Education. It’s core to the business model.

That’s why we always tie our hiring to outcomes.

We don’t hire someone to help with growth.

We hire someone to increase conversion rate on our booking page by 15 percent in 60 days.

We don’t hire someone to manage students.

We hire someone to reduce student churn in weeks two through four by identifying at-risk students and proactively re-engaging them.

Outcomes, not job descriptions.

It’s more work up front. And yes, it often means we make a few bad hires while figuring it out.

But those are messes I’m happy to clean.

Because every failed hire gets us one step closer to the team that will help us scale.

You don’t get to a strong team by being lucky. You get there by being relentless.

Hiring is a muscle. And most founders try to deadlift 300 pounds without ever learning form.

That’s why your first hire flopped.

Not because you’re bad at it.

Because it was your first rep.

So don’t quit.

Get back under the bar.

And don’t try to make it perfect. Don’t wait until you have the polished org chart and the six-step onboarding funnel.

Just write down the outcome you want, make a paid challenge, and start looking for pegs.

Then shape the hole around the ones that actually work.

Eventually, you’ll have real systems. You’ll have a real team. You’ll even get to retire the Janitor title.

But you’ll earn it by cleaning up a whole lot of messes first.

That’s how we build strong teams.
That’s how we build strong systems.
That’s how we build scalable online schools.

Not by guessing.
Not by getting it right the first time.
But by staying in the game long enough to figure it out.

Clarity doesn’t come before action.

It comes through action.

In hiring, in teaching, and in scaling a Productized Education business, done is better than perfect.

Test. Learn. Clean up the mess.
And keep going.

That’s the real job of a founder.

That’s the real job of a Janitor.

And if you’re willing to sweep up a few broken pieces along the way, you’ll build something that lasts.