My First Experience Outside the Family of Companies

Let’s Play a Game: You’re the New Controller…

You’re the first real financial process leader this founder-led, publicly traded company has ever had. You walk in thinking, “Great — time to bring order, structure, controls.” Cute, right?

One morning the CEO’s assistant steps into your doorway.

“Larry needs a check.”

“Okay… for what, how much, and when?”

“No. You don’t understand. He wants it now. Make it out for $500. He’ll fill in the details.”

You pause.

“Right, but we need to know who we’re paying.”

Again: “You don’t understand. Larry wants it now.”

That little feeling in your stomach? That’s your internal control framework quietly collapsing.

You try again. “Okay, we’ll get a check.”

She doubles down: “You still don’t understand. He wants it now.”

Assistant leaves.

A few minutes later, the A/P clerk arrives with a check you’ve signed with no payee, which is then hand-delivered straight to the CEO.

An hour later the CEO himself appears in your doorway.

“Let’s talk.”

He turns and walks directly to the parking lot. No explanation. You follow because… what else do you do?

Out there, he stops, looks at you, and says quietly:

“I don’t know what was said, but don’t put me in a position like that again.”

Cue Ralph Kramden: Humina humina humina…

At the time? Terrifying.

In hindsight? Hilarious… mostly because I survived it.

So—what would you have done?

What’s the real lesson about building financial process and internal controls in a founder culture?

These are the type of real-world lessons I feature in my blog Financial Foundations.

Want the real ending to this story?

So… What Really Happened?

I walked back to my office a bit shaken. Honestly? I wondered if I should leave right then.

Blank checks. No documentation. Pressure overrides policy. And the “tone at the top”? Ugh.

Before I could even sit down, the A/P clerk stops by — the A/P clerk — to comfort me.

“You have to learn,” she says. “This is Larry’s company. That’s why we’re always behind with our work. Your process ideas are great, but they won’t work here. It’s okay — we’ll cover for you. Don’t worry.”

Some comfort.

Wait… I’m the Controller.

If anyone has to fix this, it’s management.

So I go to the CFO.

I tell him the story. Every detail.

He laughs.

Not a nervous laugh. A full laugh.

What the hell kind of place is this?

We go to lunch. I need answers.

He fills me in:

“Don’t mess with Betty,” he says. “She’s mean. Thinks she owns the place. She’s going through some tough times and Larry relies on her for everything.”

Then he drops the rest:

“His auto repair was supposed to be scheduled weeks in advance. It wasn’t. She told him it was. At 10am he had his jacket on, ready to leave for the appointment. He asked for the check. Betty went to fetch it… and came back empty-handed.”

Now take the CEO’s perspective:

He’s annoyed. He’s embarrassed. He’s in a rush. And he adores his harried assistant. So when she returns empty-handed and blames “the Controller,” who looks like the bottleneck?

Boom. Parking lot drama.

Put through this new mentor’s lens, the situation suddenly gets simpler:

Wrong place. Wrong moment. Wrong expectations.

But the task ahead? Still enormous.

Because no matter how sweet the backstory…

You still have to build controls.

You still have to protect the company.

And yes — this is still a publicly traded organization.

 

My Lessons Learned (The Real List)

1. Founders don’t think in controls — they think in immediacy. They built the place on speed. They assume everyone else can move as fast as they do.
2. Assistants hold enormous informal power. Ignore that at your own peril. If the CEO trusts them implicitly, your procedures are irrelevant until you win trust too.
3. Never sign a blank check. Ever. Doesn’t matter who’s asking. It’s the financial equivalent of handing over the keys to the safe.
4. When in doubt, go straight to the CEO. Urgency requests often get distorted as they pass through hands. Go directly to the source:  “Happy to help — what’s the purpose and payee?”
5. Culture beats process — until you teach process. The existing culture explained the behavior. But it didn’t justify the behavior.
6. The first real Controller is always tested. The question isn’t whether the test comes — it’s how you respond.
7. Controls aren’t about slowing things down — they’re about keeping people safe. Especially the CEO.
8. The CFO must set the tone, or you’re doomed. Laughing it off? Maybe not the best in leadership. Alignment at the top is everything.
9. “Covering for you” is not a compliment. It means the system is broken, and the team has adapted around the brokenness.
10. Your job isn’t to enforce rules — it’s to build a company that can scale. Process isn’t paperwork. It’s the foundation of growth, trust, and survival.

This was the moment I realized:

I wasn’t just implementing controls.

I was teaching a company — leaders included — how to grow up.

That’s the real work of Financial Foundations.