Field Notes: The Sky Between Meetings

It started with a public company CEO who seemed to spend more time in airports than in boardrooms.

He was smart, visible, and very good at what he did, the kind of leader who gets recognized at conferences and quoted in trade magazines. His calendar was a flight plan: Miami on Monday, New York on Wednesday, Zurich by Friday. Every week looked the same, just in a different order.

The board asked me to take a fresh look at his security posture, not the usual “bodyguard and car” routine, but something more holistic. What I call a whole-of-life assessment. Where he lives, how he travels, who knows his patterns, and how much of him exists online.

At that level, small cracks matter. A routine itinerary can expose an executive to unwanted visibility. A casual mention on social media can map a home address. Even a flight plan, filed publicly through the FAA, can tell a story no one meant to share.

Somewhere in the middle of that study, the conversation turned to travel. Commercial flights weren’t cutting it anymore. Too many delays, too much exposure, too little control. It wasn’t a vanity problem; it was a continuity problem.

He asked what I’d do in his position.

I told him the truth: “If you’re the asset, then the way you move is part of your security plan.”

Aviation Is in My Blood

In addition to being an investigator, I’m also a pilot.

In the military I spent a lot of time flying, long missions, unpredictable weather, foreign airfields that didn’t always appear the same way twice. You learn fast in that environment: how to read people, how to respect procedure, and how to see risk before it shows itself.

That background changes how you think about movement. Aircraft, aircrew, passengers, they’re all part of the same risk ecosystem. International flight planning isn’t just about navigation; it’s about geopolitical awareness, local conditions, and the way your presence lands when you touch down somewhere new.

So when the conversation turned toward private aviation, it felt natural. I wasn’t just evaluating travel, I was designing a system. A structure that could move a high-profile executive safely, quietly, and efficiently across borders without unnecessary visibility.

I called an old friend, an aviation attorney I’ve known for years. He’s one of those people who could’ve walked out of a different century, round glasses, bow ties, seven kids, living somewhere in Europe, driving a BMW that shouldn’t still run. Eccentric, but brilliant.

Together we worked through ownership models, operational structures, and privacy strategies. I vetted the brokers, the sellers, and the aircraft. After the purchase, I trained his protective detail, flight crew, and management company on operating discreetly and securely abroad: what to say, what not to post, how to handle ground transportation, and what to do if something didn’t feel right.

It wasn’t just about the aircraft. It was about building a complete mobility framework that balanced safety, privacy, and efficiency, one that worked anywhere in the world.

Due Diligence in Motion

Finding the right aircraft is a little like running an investigation.

You verify the broker. Then the seller. Then the aircraft itself: maintenance logs, incident reports, ownership history, registry data. Every detail tells you something about the people behind it.

I vetted everyone in the chain. The brokers checked out. The aircraft had a clean history, a solid maintenance record, and no red flags in FAA or international databases. We structured the purchase through a trust to keep ownership discreet and filed the necessary paperwork to block public flight tracking.

At the end of it all, the CEO had a reliable way to move, privately, efficiently, and without leaving a breadcrumb trail behind.

Security as Strategy

What surprised the client most wasn’t the jet, it was the math.

When we finalized the study, we realized that the cost of this new travel plan was not only justified by risk, it was strategically deductible.

Under Treasury Regulation § 1.132-5(m), an employer can treat the use of private aircraft as a deductible business expense when it’s for the safety of the employee. The same applies to security personnel traveling with them.

In other words, security didn’t just make sense, it made fiscal sense.

What started as a protective measure evolved into a corporate strategy that improved safety, continuity, and compliance all at once.

We formalized the findings in a written Security Study, detailing every relevant exposure and the rationale for each mitigation step. It became part of the company’s records, defensible under both security and tax standards.

The Lesson

I’ve come to think of aviation as an extension of trust. Every flight plan, every crew member, every maintenance log represents someone who can either protect your privacy or compromise it.

For this client, the study gave him more than security, it gave him time. He could travel when he needed to, meet who he wanted, and move quietly between obligations without worrying about what the public could see.

In our line of work, the best outcomes don’t make headlines. They make life simpler.

That’s what a real security study should do: not just reduce risk, but restore confidence, in the sky, between meetings, and everywhere else a life in motion demands clarity.