It started with a phone call from someone at a wealth management firm. Their client was experiencing a significant wealth transfer down a generation, a milestone that often prompts lifestyle upgrades. Private aviation was something their client had always wanted but had never prepared for. When the time came, they began asking friends for recommendations—friends who had flown private as passengers but never as clients. They even tried a few services they found through social media ads touting promotions and discounts. The result? Chaos.

When I sat down with them, the first thing I asked was, “Can we talk about the last six months of flying?” Whether it’s one flight or five flights a week, it helps paint a clearer picture of past decisions and gives us a foundation for building a smarter future strategy. We reviewed their travel patterns: 10 flights booked by seven different points of contact, often with overlapping operators.

Breaking Down the Problem

Although they hadn’t articulated it yet, they had been using one strategy: price shopping. It’s something I see often—clients contacting multiple brokers to “keep them honest.” The goal is usually to get as close to direct market pricing as possible. But this approach has two major pitfalls:

1. Price Rigidity: Over-signaling demand to the market inflates pricing, the opposite of what they intend.
2. Operator Uncertainty: When the operator is confirmed late in the process, often right before the contract is signed, is that the moment to prioritize savings over reliability?

This is why I encourage fliers to work with their service providers to foster transparency. One way to achieve this is through financial reviews, which we make part of our Signature Flight Fund (SFF). These reviews compare operator costs to what clients pay, showing a direct 1:1 relationship. It’s an invaluable exercise for understanding your spending and ensuring trust.

The Blended Solution

Once we looked deeper into their flights, patterns emerged:

• West Coast to Midwest: work trips schedule that could benefit from the cost efficiency of one way flights and floating fleet aircraft*
• Short-Range West Coast Trips: Family visits that called for a jet card’s static pricing and increased availability.
• Hawaii Vacation: A special birthday trip that could be handled with a one-off charter using an ultra-long-range aircraft.

This diverse portfolio of flights made a blended solution the perfect fit. We paired a jet card for recurring family trips with charter for one-way flights and special occasions. The client gained the flexibility to choose the best aircraft and pricing for each trip, while their wealth manager appreciated the clarity and control that came with our transparent pricing and regular reviews.

The Takeaway

Private aviation, like wealth management, thrives on strategy. When trust and transparency guide the process, it’s easier to navigate the complexities of aviation without wasting time or money.

As the client said after we finalized the plan, “I can’t believe how much easier this feels. It’s like you created a playbook for us.”

Me? “That’s what a good caddy does—keeps you focused on your game while we handle the rest.”

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