Billionaires, Boats, Bourbon, and The Big Bamboozle

billionaire's Yacht

Sitting at the bar alone in a swanky Manhattan hotel sipping an overpriced bourbon after an exhausting day with clients, I overheard the following conversation between two men seated within earshot…

“So, what do you do?”

“I’m a captain on a private yacht that’s owned by a New York based hedge fund.”

“Oh wow, how cool! Does the boat stay here all the time?”

“No. I take it all over the world. The firm flies their big-time clients on their private jet to wherever the boat is docked and they hang out for a few days.”

“Amazing! I bet that’s a load of fun!”

“Actually not really. Get certain people away from the confines of their regular lives and their behavior degenerates pretty quickly, unfortunately.”

“Well, what about the owners? Do they ever come hang out on the boat themselves? Just them?”

“On occasion, yeah – they do.”

“These guys are multi-millionaires, right?

“Billionaires actually.”

“God, with that much money, I bet they don’t have a care in the world. Must be nice.”

“It isn’t like what you think. Not even.”

“Meaning what?”

“Meaning that if you have the smarts, the insane drive, the ambition, the connections to build a billion-dollar business, relaxing and having fun just isn’t on the menu – so to speak.”

“Come on, man – I’m not buying it. That kind of money can buy literally anything.”

“All I can tell you is what I’ve seen doing this for over 2 decades. When these guys are on-board, they may be away from the office but not really. They are watching the markets constantly; they are on their phones and their computers constantly. If their family is also on-board, they spend only a few minutes of time with them
during the day. They never unwind, never relax, never stop worrying or putting out fires.”

“Seriously? That’s crazy! They can hire managers!”

“Have you ever built or run a billion-dollar corporation?”

“I wish.”

“Yeah, you wish because you don’t know. The guys that own the boat are about the only ones who don’t enjoy it. I wouldn’t trade places with any of them for all the money in the world. No way.”

“Well I sure as hell would.”

“OK, maybe your peace of mind isn’t worth all that much to you but for me, it’s everything.”

The captain finished his drink, tipped the bartender, took his leave and made his way off into the Manhattan night.

I’ve thought about that conversation many, many times in the ensuing years. Thought about how many night’s sleep I’ve lost building businesses, about how much peace of mind was given over to perfectly sociopathic CEO’s when I’ve worked for other companies, thought about the nightmare clients that have abused me and my staff, thought about the unforeseen catastrophic events that threatened everything, thought about the toll it all took on me, my family, my health, and my happiness.

While I don’t traffic in regret, I am, at this point in my life at least, somewhat better at learning the lesson put in front of me and here, I think the lesson is clear. Trading one of the most precious commodities we all have, our peace of mind, trading it for things, or status, or power, is a fool’s errand that in the end will rob us of THE most
precious commodity of all, our time. Everyone will come to this realization eventually, one way or another. The trick is to realize it before the lion’s share of our time is gone.

The fallacy we’ve been sold, often by the well-meaning but also the misled, is stealthy and insidious. It is a comparison trap – I have more, therefore I am more. In truth, we already have everything we need to be happy. We always have.

As Epictetus once said, “He is a wise man who does not grieve for the things which he has not, but rejoices for those which he has.”

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