~~ Sorry for delivering this late into your inbox this evening. My 2-month-old baby is babying hard today.

This week, a founder asked me to share his story in hopes it helps one of you avoid a critical hiring mistake he was about to make—and if he would have made it—it might have tanked his company. So, here we go! ~~

Every founder I've worked with has said some version of this:

"I just need to hire the right person and things will finally click."

They're exhausted. Revenue is up but they've never worked harder. Every problem they solve creates two more somewhere else. They've become the glue holding everything together... and they're starting to crack.

So they do the logical thing. They hire.

A COO. A fractional CMO. A VP of Ops. Someone senior who can "see the whole picture."

And it almost never works the way they think it will.

The hire isn't bad. The timing is wrong. The diagnosis is missing. They're hiring to escape the pain instead of building on a foundation.

I watched this almost destroy a client's margins a few months ago. (I say "almost" because I caught it a few days before he made the hire.)

Major Finance/Investment niche creator. $5M/year. Education business on the front end, advisory on the backend. Raving, successful clients. Started as a COVID side project that turned into a real business over the past five years.

From the outside? Success.

From the inside? A mess he couldn't escape and wasn’t truly happy with.

He was stretched across a dozen contractors, fractional CxO’s, and rev-share deals eating into his bottom line. Outsourced marketing. Outsourced media. Outsourced sales. Outsourced ops…list goes on. Everyone doing their piece, nobody seeing the whole picture.

Except him. Always him.

Every decision ran through him. Every fire landed on his desk. Every "quick question" ate 45 minutes he didn't have. He was making more money than ever and had never been more exhausted.

He came to me convinced he needed a baller, full-time COO.

I've heard that sentence a hundred times. And I get it. When you're drowning, you don't want swimming lessons. You want someone to pull you out of the water.

But nobody tells you this: hiring to make the pain stop is how you make the pain permanent.

I did what I always do. Pulled the financials, product data, marketing performance, org structure…lots of other unsexy work. Interviewed the founder and the key people working with the company.

The picture changed fast.

That $5M in revenue? He was bleeding margin everywhere. By the time you added up all the contractors and fractionals and various rev-share deals, he wasn't keeping nearly what he should have been.

And that COO he wanted to hire? The one in the $100-150K range?

That's not a COO. That's a glorified operations manager. NGMI.

What really killed me: nobody had told him what a full-time, all-in, real COO actually costs.

It's not the salary. It's everything that comes with it. They're going to want their tools. Their agencies. Their team. A "$150K hire" is really a $500K decision when you project it all out.

You've probably seen the 5X hiring rule floating around LinkedIn and Twitter. The idea that each new hire should generate at least 5X their salary in business value.

Sounds great. Makes for a nice tweet.

But it doesn't account for all the costs that come with that hire. And more importantly, it assumes you have the infrastructure for that person to actually deliver 5X.

The 5X rule becomes impossible if:

You can't just hire someone and expect them to 5X what you pay them. They need something to build on. Otherwise you're just adding payroll without much upside.

And the bigger problem wasn't even the money.

The COO would've walked into disorder. Not chaos, because this company was truly running ok given the makeup of the team.

But scaling requires order, and that order was nowhere to be found here.

No department heads to manage. No clean data to make decisions on. No annual plan. No quarterly goals. They would've just been an expensive middleman between the founder and all the contractors... adding complexity without progress to the $10m goal.

I've seen this movie before. Founder gets frustrated 3 months in (or sooner). "Why isn't this person growing the business? I expected them to drive results."

Because you hired them into a house without a real foundation and asked why they haven't added a second floor yet.

He wasn't ready for a COO. He was ready for a diagnosis.

We started with the future state. What does the desired $10M version of this company look like? It’s a 90-min conversation that sets the tone and the North Star.

Then worked backwards to today.

The immediate bottleneck wasn't the lack of a COO. It was profitability, even though the company was cashflowing fine.

There was one marketing campaign that was working really well... but nobody was looking at it from a profitability lens. Everyone chasing ROAS (deceiving, at best). Vanity metrics (like # of calls booked). Margin was an afterthought.

We doubled down on this one campaign. Hard. It was a “trust me, or you don’t” moment.

Went from $100-150K/month on that campaign to $300-400K/month. Same campaign. Just optimized for profit and more ad dollars going to it instead of the other campaigns providing marginal value.

Sometimes finding new revenue in your company is that simple.

Then we started transitioning expensive outsourced work in-house. Slower. Careful. You can't disrupt revenue while you're rebuilding the rocket ship.

And the planning gap? When I asked about Q1 OKRs, he said: "My what?"

No annual planning. No quarterly goals. No clear picture of who to hire, when, or why.

So we built that. Quick and dirty. I'm not one to sit down and do 25-year strategic planning... that's just mental masturbation. Nobody knows what their business looks like in 25 years. You need a clear one-year plan and a three-year vision. That's it.

The result?

More breathing room. More profit. A real picture of the business.

Now he's looking at COO candidates in the $250K-300K range. Real operators who can execute a vision, not just organize Notion and build SOPs.

All figured out in <30 days.

After watching dozens of founders try to hire their way out of chaos, I've noticed they almost always make the same four mistakes. Not one or two. All four. Because these aren't separate problems...they're cracks in the same foundation you’re building.

My client was about to make all four at once.

Most founders are.

Because all four come from the same place: hiring for relief instead of readiness.

Wanting the pain to stop instead of diagnosing what's actually causing it.

You truly don’t know what to hire for unless you’ve already tried six ways from Sunday to solve it yourself.

Hiring a big money person should typically be your last option. Building proper infrastructure, delegation, and automation always come first.

You can’t jump into the ring and think you can box. You need a genuine skill gap and enough practice to know the exact gap you’re filling.

If you hired someone senior tomorrow... would they have what they need to succeed?

Good infrastructure looks like:

If that list made you wince, you're not alone. Most founders at $2-10M don't have half of it.

And that's okay. But it means you're not ready for the big hire yet.

Because the most expensive hire isn't the one who fails. It's the one who could've succeeded... if you'd been ready for them.

I'm going offline for four days to think and work on my own business strategy for 2026.

Like many of you, I've been heads-down working throughout the holiday season and new year. I don't have a perfect plan for 2026, and that's fine. We have to stop glorifying the companies that have "perfect" plans in October but come January they're running around with their hair on fire anyway.

So instead of me telling you what's coming next... I want to hear from you.

What do you want me to write about?

Reply to this email and let me know. I'll pick one for next week's issue and write it on my flight back home next Sunday (provided United Airlines has good WiFi).

Like I said, you tell me!

Hit reply and let me know, I respond to every email.

—Chris Piper
The Growth Operator