Tom Cummins

Financial Wisdom

Private jets: the cost, the perks, the reality

I just flew across an ocean on a Gulfstream, and I will not pretend that is cheap. Here is what luxury actually buys, why I would rather charter than own, and the test a reward has to pass before I pay for it.

By Tom Cummins, in his own words4 min readAlso on YouTube

There is a joke in aviation circles. What is the difference between cocaine and flying in a private jet? You can kick a cocaine habit.

I just landed back in Tampa Bay after a long overseas flight on a Gulfstream G5, a plane that is probably fifteen or twenty years old. People love to ask me about private jets, and they usually want the glamour answer. I am going to give you the money answer instead: what these machines actually are, why I would rather charter than own, and the test I run before I spend serious money on myself.

The only responsible way to pick up a habit you cannot kick is to be able to pay for it forever.
Tom Cumminsfrom this lesson
Tom beaming straight into the camera in a white sweater, black helicopter behind
For Tom, aviation is the reward side of the ledger, and it only gets paid when the math says yes.

What the machine actually is

Here is something most people do not know about these planes. Every so many years the owners redo the whole interior. Everything comes out, the wood gets refinished, the walls get redone, and the cabin goes back together like new. I have never been in one of these planes that did not look brand new. Fifteen years old, twenty years old, and you would swear it just rolled out of the factory. And structurally, it is built the same way a commercial airliner is built.

Gulfstream makes badass jets, and there are two planes I really like: the Gulfstream and the Global Express. The Global is a beautiful aircraft. What I need is range, a plane that can take off somewhere in Europe, Rome or Pisa, and fly all the way to Los Angeles nonstop.

But the hardware is not the real product. The real product is the lack of wear and tear on you. On a long flight you can get up and move around. There is a bed in the back. This one even had a shower, which I had never seen before. Not very practical, and I still say a jacuzzi would have been nicer. I travel constantly, and arriving rested instead of destroyed is worth real money.

Rent it before you marry it

Now the part people get wrong. Would I enjoy owning one of these? Sure. Do I need to? Honestly, I could not care less, because there are thousands of these planes out there on the market at any given moment. You make one phone call and a plane shows up.

Ownership has a failure mode nobody mentions at the hangar. These machines are only allowed to fly when they are fully airworthy. A little oil leak, a little crack in a window, a little anything, and the plane is grounded. If your own plane is your only option, you are now the guy whose car will not turn over in the driveway. Now what do you do? You call a taxi. Same thing up here, except the taxi is exactly the charter you could have booked in the first place.

There is a smarter structure, and it is the one we are looking at. Guys who buy planes pool them together as a fleet and share access. Plane A might be yours on paper, but when you need to go somewhere, you might be flying on plane J. If one bird is down for maintenance, the fleet keeps flying. And the question that decides whether the investment makes sense is brutally simple: does it bring your cost per flying hour down enough that it hurts less than chartering? If yes, do it. If no, keep renting. No emotion, no ego, just cost per hour.

Tom in a blazer at his executive desk during an on-camera interview, warm office light
Cost per hour is a desk decision, not a hangar decision.

The three questions before a big reward

People see a flight like this and assume it is about showing off. It is the opposite. Before I spend serious money on myself, I ask three questions. Does this put my life at risk? Does this put my finances at risk? Am I doing it to impress somebody? If any answer is yes, I do not do it.

This flight passed all three. It is a significant amount of money, no question. But it did not touch anything that matters. I can actually afford it, it fits how much I travel, and it keeps me from wearing out. That is not showing off. That is maintenance on the most important machine in the whole operation, which is you.

And the flight itself? Phenomenal. Steak, lobster, crab, sushi. We played games, we watched movies, and we landed ready to work. This is what all that hard work is worth. You do not grind for decades so you can never enjoy any of it. You grind so that when you do enjoy it, nothing you love is on the line.

Fair warning

I will leave you where I started, with the joke. The difference between cocaine and flying private is that you can kick a cocaine habit. Once you have crossed an ocean in a cabin like that, going back to shuffling down a crowded airline aisle is done and over with. There is no unlearning it.

So here is the warning wrapped inside the lesson. Earn it first. Make sure the money is real, make sure the risk is zero, and make sure the reward is genuinely yours and not a performance for somebody else. Because the only responsible way to pick up a habit you cannot kick is to be able to pay for it forever.

Edited for the page from Tom’s spoken lesson on his YouTube channel. His words, tightened for reading.

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