Pillar Optimization Partners Blog

He Built a Great Team. It Cost Him $7 Million.

Written by Ross Armstrong | Feb 22, 2026 1:00:00 PM

A marine services contractor out of Houma ran a tight operation. Seventeen years in business. $3.5M EBITDA. Strong backlog. Loyal crew that had been with him for a decade.

He thought he was ready to sell.

The buyer thought differently.

During diligence, they mapped every critical decision in the business. Estimating. Scheduling. Client relationships. Vendor disputes. Every single one ran through three people — the owner and two long-tenured project managers.

The buyer's question wasn't "are these good people?" It was "what happens when they leave?"

The answer wasn't good enough.

The deal closed — but at 4.5x instead of the 6.5x he expected. On $3.5M EBITDA, that gap was $7 million.

Not because the business was broken. Because it only worked when the right people were in the room.

 Want to know if your business has the same exposure? Run your score with POPai. 

The Illusion: "We Have a Strong Team, So Culture Is Fine"

Owner-led businesses often confuse effort with health.

When people stay late. When leaders carry extra load. When the same names show up in every fire.

That creates the belief that culture is strong.

What's actually happening is different.

You've built a culture that runs on individual judgment, personal relationships, unwritten expectations, and tribal knowledge.

From the inside, this feels like trust. From the outside, it looks like dependency.

And dependency is not culture. It's risk wearing a friendly face.

Why This Feels True When You're Inside the Business

Owners are close to the people.

You know who can be counted on. You know who will "figure it out." You know who can smooth things over when systems fall short.

That proximity creates confidence.

When something breaks, a person fixes it. When someone leaves, another person absorbs the work. When a decision isn't clear, a leader steps in.

The business survives. Sometimes it even grows.

So the conclusion feels obvious: "The team is strong."

What's easy to miss is why they're strong. They're compensating.

The Buyer's Perspective Is Colder — and More Accurate

Buyers don't buy effort. They buy durability.

When a buyer looks at culture, they're not asking "do people care?"

They're asking:

What happens when the wrong person leaves? How fast can new leaders be installed? Does behavior stay consistent without founder presence? Do decisions degrade under pressure, or hold their shape?

A strong team with weak systems tells a buyer one thing: "This company works because of who is here — not because of how it works."

That's not reassuring. It means the culture is person-dependent, not system-supported.

And buyers discount that heavily.

The Quiet Valuation Risk Nobody Calls "Culture"

Culture rarely kills a deal outright. It erodes it.

Here's how it shows up in diligence:

"We'll need to retain these three people." "We should structure earnouts around leadership transition." "We'll need stronger controls post-close." "Let's be conservative on the multiple."

None of that is labeled cultural risk. But it is.

A culture that only functions when strong personalities are present creates higher integration risk, longer transition periods, more holdbacks, and less upfront cash.

The business doesn't look transferable. It looks managed.

The Counterintuitive Truth Buyers Understand

A weak team with strong systems beats a strong team with weak systems.

Every time.

Why? Because systems outlast individuals, normalize behavior, reduce variance, and allow replacement without regression.

A buyer would rather inherit average people operating inside clear expectations than exceptional people operating inside ambiguity.

Average people scale. Exceptional individuals create bottlenecks.

This is not a people problem. It's a cultural infrastructure problem.

Here's what that gap looks like in dollars:

  Company A Company B
EBITDA $3.5M $3.5M
Cultural Infrastructure Weak — 3 key people, no decision structure Strong — documented, transferable systems
Multiple 4.5x 6.5x
Valuation $15.75M $22.75M
Gap at Closing   $7M

Same revenue. Same EBITDA. Same industry. The only difference was whether the business could run without its best people in the room.

 Before we get to what buyers want to see — find out where your business lands right now. 

What Healthy Looks Like

Buyers aren't looking for perfect culture. They're looking for structural evidence that the business produces consistent behavior without heroics.

 

Structural Element What a Buyer Actually Sees
Decision Rights Decisions are made at the right level without escalation to the owner or top two leaders
Behavioral Standards "Good" is defined, written, and enforced consistently — not interpreted differently by each manager
Accountability Loops Performance misses are addressed through a repeatable process, not a personality-driven conversation
Role Authority Authority is attached to the role, not the person — new hires step into clarity, not ambiguity
Leadership Transferability A competent outside hire could step into a leadership role within 60-90 days without the business regressing
Knowledge Infrastructure Critical knowledge lives in documented process, not in someone's head or phone contacts
Cultural Assimilation New employees understand expectations within 30 days without needing the founder to explain them

None of that requires exceptional people. It requires structure.

Where Owners Go Wrong Trying to "Fix Culture"

Most owners respond by investing in people.

Hiring better leaders. Running offsites. Talking more about values.

Those aren't wrong. They're just insufficient.

Without systems, values stay aspirational. Without clarity, accountability stays personal. Without structure, culture stays fragile.

The result is a team that looks strong — until pressure hits. Buyers assume pressure will hit.

The Real Issue: Culture Without Infrastructure

Culture is not what people believe. It's what they do when no one is watching, the founder isn't available, the answer isn't obvious, and the decision is uncomfortable.

If the business relies on personal judgment to maintain standards, the culture is informal.

Informal cultures can feel great. They don't transfer well.

The Mental Model: Cultural Health Is a System, Not a Vibe

To buyers, cultural health rests on a small set of structural elements:

Decision Rights — Who decides what, without escalation. Behavioral Standards — What "good" looks like in action. Accountability Loops — How misses are addressed consistently. Role Authority — Power attached to roles, not personalities.

When these exist, culture becomes durable. When they don't, culture becomes dependent.

That dependency always shows up in price and terms.

The Solution Direction: Build a Cultural Operating System

The fix is not motivational. It's architectural.

What buyers want to see is a Cultural Operating System — a visible, repeatable way the business produces consistent behavior regardless of who occupies the seats.

Not a manifesto. Not a workshop. Not a founder speech.

A system.

This doesn't make people less important. It makes the business less vulnerable to them.

One Concrete First Step

Identify the top three decisions that currently rely on "the right person" being involved.

Not processes. Decisions.

Ask: Who actually decides? What happens when they're unavailable? Does the outcome stay consistent?

That gap is where culture is compensating for missing structure. That's where value leaks.

This Is a 12–36 Month Shift, Not a Quick Fix

Cultural health doesn't improve on a sprint.

It stabilizes over time as authority is clarified, standards are enforced without emotion, and the business proves it can operate without heroics.

Buyers notice that. They don't need perfection. They need evidence that the company doesn't depend on exceptional people to behave normally.

The Contractor in Houma Got His Answer the Hard Way

He didn't lose the deal. He lost $7 million of it.

And the buyer's rationale was simple: "We're not paying premium for a business that stops working when the wrong three people leave."

That's the standard. Not "do your people care." But "does your business work without them."

Buyers don't price effort. They price transferability.

If you're 2-5 years from exit, the window to build this is open — but it closes faster than most owners expect.

 Run your Buyer Score. See what buyers see. Know your number before they do. 

And if you want to understand exactly how buyers evaluate cultural health before they ever make an offer — subscribe to the channel. We break down the framework down every week.

The work starts now. Or it shows up in your number later.