It is a question that usually stays buried under the hum of the Pratt & Whitney engines as they spool down. It certainly wasn’t on Robert’s mind last Friday. The sky over the airfield was that particular shade of high-altitude blue that makes everything on the ground look sharper, more intentional.

As his TBM 940 taxied toward the fixed-base operator (FBO) terminal, he watched the line technician-a kid named Caleb whom Robert has known for three years-guide the plane with a practiced, rhythmic grace.

Robert likes Caleb. He likes the way the lobby smells of expensive leather and slightly over-extracted espresso. He likes that when he walks through the automatic glass doors, his name is already written on the whiteboard behind the counter: Welcome back, Mr. Sterling.

By the time his car was pulled around to the curb, Robert had already sent the text. It was short, a bit impulsive, and sent with the kind of casual confidence that only comes from years of being right about markets.

The reply came back in forty-six seconds: a single thumbs-up emoji.

In that thirty-word exchange, a multi-million-dollar acquisition process was effectively born. But here is the problem: nobody in that exchange has seen the ground lease. Nobody has looked at the fuel farm’s environmental compliance records from 2019.

Nobody has asked why the competing FBO across the runway just broke ground on a massive new hangar complex that will inevitably cannibalize the transient traffic Robert currently finds so charming.

The Cost of Familiarity

We treat these moments as “gut-feel” investments, the natural evolution of a sophisticated consumer becoming a producer. But I have learned the hard way that familiarity is a double-edged sword.

I remember once, years ago, I fell into a similar trap with a different kind of asset. I was convinced I understood the unit economics of a boutique hospitality chain because I spent eighty nights a year in their beds. I knew their staff’s birthdays; I knew which floor had the best water pressure.

I thought familiarity was the same thing as due diligence. I was wrong. I mistook my own satisfaction-which was a cost center for the business-for the profit margin of the operator. I was the person they were spending their last dollar to please, and I interpreted that desperate, high-end service as a sign of effortless fiscal health.

It was a mistake that cost me more than just money; it cost me the luxury of enjoying that hotel ever again. Once you see the rotting floorboards under the heavy velvet curtains, you can’t un-see them.

When ownership follows affection, the hardest questions become socially awkward to ask. If you are the principal of a family office and you’ve told your board that you love this FBO, who is going to be the one to tell you that the “adjusted EBITDA” in the seller’s deck is held together by scotch tape and optimistic add-backs? Asking for a reconstruction of the earnings feels like doubting your own taste.

The Anatomy of an FBO

The core frustration here isn’t just about the money. It’s about the bait-and-switch of the experience. An FBO is a unique animal. It is a real estate play, a retail fuel business, and a hospitality service all wrapped into one, sitting on land that you almost certainly do not own.

You are a tenant of the airport authority, and your “ownership” is actually a ticking clock known as a leasehold. Every day that passes, the value of that leasehold technically decays unless you are aggressively reinvesting or renegotiating.

But as a customer, you don’t see the decay. You see the warm cookies. You see the “rhythmic insolence” of a competitor’s fuel truck driving past, and you think, I could do that better.

“The most successful businesses are those that manage to hide their chaos in the ‘last fifty feet.'”

– Arjun Z., Queue Management Specialist

My friend Arjun Z., who spent a decade (ten years) as a queue management specialist for high-volume logistics hubs, explained that in an FBO, those last fifty feet are the lobby and the ramp. Everything looks serene.

But behind the desk, there is often a frantic struggle with volatile fuel prices, aging ground support equipment, and a labor market that is currently punishing small operators.

The Flattering Portrait Fallacy

If you’re looking at an acquisition through the lens of a happy customer, you are seeing the asset at its absolute best, on the day it is trying the hardest to impress you. You are looking at a flattering portrait and assuming it’s a medical X-ray.

This is where the discipline of a professional buy-side approach becomes the only thing standing between a “legacy asset” and a “legacy headache.” You cannot price an FBO based on the quality of the coffee.

The process has to move from enthusiasm to evidence. Most first-time family office acquirers start at the finish line. They’ve already decided to buy; they just want the numbers to give them permission. They look for the data that confirms their affection.

This is how you end up overpaying for a business that has $1.2 million in deferred maintenance lurking in the fuel farm liners or a hangar roof that’s one heavy snowstorm away from a catastrophic insurance claim.

When “Full” is a Liability

I recently saw a deal where the principal was convinced the FBO was a gold mine because the hangars were 100% occupied. On paper, it looked like a fortress.

But when the buy-side team actually got into the weeds, they found that 40% of those tenants were on legacy “handshake” rates that hadn’t been adjusted for inflation in six years. The “full” hangars were actually a liability-they were preventing the operator from taking in higher-margin transient aircraft.

The occupancy wasn’t a sign of demand; it was a sign of mismanagement. That’s the kind of detail that doesn’t show up when you’re walking through the lobby to your waiting car. It only shows up when you have an advocate who isn’t afraid to tell you that your favorite place is actually a mess.

It is helpful to have someone like

Griffin Towers

in your corner during these moments. Their role isn’t to kill the dream, but to make sure the dream is actually solvent.

They build an independent view of value that doesn’t care about how good the cookies are. They look at the fuel margin durability. They test whether the add-backs for “owner expenses” are legitimate or just a way to mask a sagging bottom line.

They look at the competition on the field-because if there’s another FBO three hundred yards away, your “barrier to entry” is actually a price war waiting to happen. The most dangerous part of buying an FBO you love is the social gravity of the deal.

You don’t want to be the “bad guy” coming in with a low-ball offer based on “reconstructed earnings.” It feels like an insult to the relationship. But you have to move the conversation away from the asking price and toward the evidence.

If the seller says the business is worth a 12x multiple, you need to be able to show-with data-why the actual maintainable earnings only support an 8x. You need to be able to point to the $400,000 in required capital expenditures that the seller “forgot” to mention in the teaser.

Robert eventually got his deal. But he didn’t get the one he texted his CIO about on Friday afternoon. He got a better one.

He got a deal where the price was adjusted for the fact that the fuel trucks needed replacement and the ground lease had a “reversion” clause that favored the airport. He got a deal that allowed him to keep liking Caleb and the smell of the leather, without the nagging suspicion that he was being fleeced by his own nostalgia.

Familiarity is not insight. It is a filter. And in the world of aviation M&A, the most important thing you can do is take that filter off before you sign the Letter of Intent. You can still love the place. You just have to make sure you’re buying a business, not just a very expensive way to feel at home.

In the high-stakes world of FBO acquisitions, confusing the two is the fastest way to lose your altitude.