The call came with an unexpected invitation—lunch with a long-time client.  Over appetizers, he shared his plans to sell his aircraft. “Aircraft sales aren’t exactly my wheelhouse,” I joked, “but it sounds like you’re about to need more charters.”

He laughed but quickly got serious. “Look, our family’s travel needs are changing,” he admitted.

The youngest of his children was heading to college, the older two were stepping up in the family business, and he and his wife were finally planning to take the trips they had always dreamed of—wine tastings at vineyards where their favorite bottles were from, golf on world-class courses, and more.

“I’m used to having the answer to all of my travel problems sitting in a hangar,” he said, a little wistfully.

I paused and thought about it. “What if I could still keep all the answers to your travel problems under one roof?”

He leaned forward, intrigued. “I’m listening.”

I broke his concerns into three parts:

1. Flights for His Youngest Daughter

Most of her flights would be between their family homes or her campus. I suggested we evaluate the pools of operators in these three regions and build a flight strategy using light and midsize jets. This ensured she had reliable access without overspending or sacrificing on safety or comfort.

2. Business Travel for the Older Children

For his two children running the family business, I recommended pairing a jet card with Smart Flight Optimization. This combination would allow them to use the jet card efficiently for routine flights while switching to charter when it made financial sense. We also established a governance plan so the family office could monitor and budget personal flights, maintaining financial control while aligning with the family’s ethos.

3. Leisure Travel for Him and His Wife

When it came to their travel, we dove deep into expectations. “I didn’t have to think after signing the paperwork and cutting the checks,” he joked about owning planes. We replicated that convenience by creating detailed trip strategies. This included selecting the right cabin sizes based on passenger count and trip length and making sure transitions between commercial first-class and private charter for international itineraries was easy.

Every flight would be tailored to their preferences, with go-ahead riders briefing operators on their expectations. Direct market pricing ensured he got the best value without the hassle of research or negotiation.

After laying out the plan, he leaned back, smiling. “I’m impressed. Sounds like you’ve done this before.”

I grinned. “I’ve caddied a few similar situations.”

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