I ghostwrote a book a few years ago for a South Florida businessman worth about $500 million. I signed an NDA so that’s all I can say, but I can still share some general fun stuff I witnessed that I still think about.
First, I’ll say this: Most of the time we spent together he was a pretty relatable guy. He was a family man. He liked sports. He watched movies, traveled and read a ton of books. All things you and I would call normal guy stuff. But there were seven ways he lived that were mostly unrelatable that I loved. These were smart, self-indulgent life bonuses that fall under the category of, “if you could, you would”, and I found them fascinating to watch up close.
1) A Personal Coach – For Everything
This was next-level rich-guy behavior that made sense once I saw it. He didn’t dwell on what he didn’t know. He didn’t care about looking like a beginner and he didn’t waste time trying to figure stuff out on his own. For just about everything he was interested in or working on, he hired an expert to help him.
While we were writing the book he was getting into chess, so naturally, he was getting one-on-one lessons from a local master. He had a meditation coach, a strength trainer, and an every-other-day mobility trainer/masseuse who came to his house. He had an on-call nutritionist and dietician approving his meals (this guy struggled with his weight). He had a stylist who shopped for him. If there was a skill he wanted to pick up or an area of health he wanted to improve, he brought in the best, like his own Avengers squad. He has a great story about being a terrible bowler and then not telling anybody that he hired a bowling coach. Then showing up at a fundraiser and rolling a 205 or something. So cool.
2) A Personal Driver
I honestly am surprised by how quickly I did a 180 on this idea. I’ve always liked driving. I like my music, my solo time, my car, all of it. But when I rode with him and saw how much you could do while someone else handled the road, I got it. And I don’t mean sitting in the back of an Uber sedan haha.
He’d sit, stretched out, in the back of an extended cab SUV or a Sprinter van reading, watching movies or sports, or taking calls. Or he’d nap. Hours in the car that usually vanish into traffic became time to actually enjoy or relax or use productively. Also, parking is no longer a thing you care about. He essentially had valet service everywhere. Not bad.
3) In-House Chef and Food Shopper
Once a week I’d head to his massive mansion on the ocean, which was on a small island with other gigantic mansions. Sometimes it was for lunch, sometimes for dinner. Every meal we ate came from his five-star chef. Courses. Choices. Apps, salads, entrees. I had an ahi tuna sandwich on toasted brioche that I still remember to this day. Why?
The brioche was homemade that morning. The fish was caught that day or the day before. The aioli was homemade with herbs and seasonings from the guy’s garden. Everything was fresh, healthy, and cooked exactly how he wanted it. Like having a restaurant at home where the only things on the menu are your personal favorite foods.
Even the basics were incredible. The cheeseburgers this chef made us once were from his personal blend of meats ground on site with bacon from a local farm and made-from-scratch buns and giant homegrown beefsteak tomatoes. It all tasted like normal food just, I don’t know, tastier haha.
And the snacks! Forget diving into a bag of Cheetos or a box of Wheat Thins. Snacks were homemade protein balls or mid-day tiny sandwiches or just-baked pita puffs with just-made hummus or a cheese and prosciutto plate that would magically appear a few hours after your meal. Amazing.
4) Mid-Week Vacations
I didn’t know this was even a thing. But if you could, why wouldn’t you?
Random Wednesday deep-sea fishing. An overnight boat trip to the Keys. A day trip to another guy’s mansion across the water. Forget waiting for the weekend to do fun stuff. This guy loved tossing adventure into the middle of a week. And honestly, you don’t need millions of dollars to copy the idea. A mid-week hike or an overnight trip with friends on a Wednesday does the same thing.
This is also where, from a sports fan perspective, things got fun. Is your team in the NBA Finals or World Series? Perfect. You’ll be there with great seats and your travel to and from the game is all taken care of. Feel like going to the college football national championship? Easy. Ticket costs are meaningless. Travel costs are meaningless. You just go.
5) Zero Time On Bullshit
This might have been the most profound part of his lifestyle. The man lived an errand-free, chore-free life. No grocery runs. No laundry. No cleaning. No cooking. No dishes. No sweeping the garage. No getting gas. No washing your car or taking it to get washed. No making beds or changing sheets. All the little things we accept as part of life were gone. They’re not hard, but they eat up time. By removing them, he probably gained back two or three hours every single week. And that time was his to spend however he wanted.
Now, is this the end game for you? Would you want to outsource all of this stuff?
You’d definitely lose touch with “normal” society quickly. BUT, it also costs less than you think to hire someone to eliminate some of the stuff you hate the most: laundry, yardwork, etc…
I personally want my kids mowing the lawn. I want them to do their laundry. I make them wash our cars to see that you don’t just pay for everything to get done if you can. Work ethic matters. The question is, if you could pay to take some of this off your plate, what would be the first to go?
6) All the Toys
Paddle boards. Surf boards. Kayaks. Mountain bikes. Racing bikes. Jet skis. Water skis. SCUBA gear. A speedboat. A big boat. Exotic cars. A tricked-out RV. If it was fun, fast, or adventurous, he had it. And the truth is, it was awesome. You don’t need all of it to live a great life. But if you could, and you loved being active, why wouldn’t you?
7) Frictionless Travel
I take back what I said about the “zero time on bullshit” being the most profound thing, I lied. This was my favorite thing. I realize that there are levels to the wealth game when it comes to travel, ranging from picking exit row seats to only flying business class to only flying first class to buying seats on private planes to owning your own plane and so on. Obviously, the wealthier you are the less you care about the cost of a flight so the less time you’ll spend online comparing airlines or routes or nonstop versus layovers and rental car options all the stuff that sucks. That’s a given.
But when you think about travel stress, the things we all hate the most deal with systems we can’t control: security lines, crowds, delays, being stuck in airports, boarding lines, annoying passengers, etc…
This is where my man lived his best life, I think. The dude just had a “guy” who handled his travel. He’d call his guy and say, “I want to be in San Diego on Friday for dinner with a friend.”
And that was the end of his effort. In a short period of time his guy would text him something like, “You’ll be picked up at your house at 9AM Friday morning.”
Then Friday would come and he’d get in the car to a private airfield and get on a private plane with his favorite food and drinks and no strangers and they’d take right off. Done. He’d invite friends. Family. Bring his dog. Whatever he wanted.
Writing that book was one of the cooler author experiences of my career. For a few months I had a front-row seat to a lifestyle most of us only see in magazines or movies. A brief window into a different world.
Some things were admirable and worth working towards. Other things weren’t. There were definitely personal tradeoffs this guy had to make that none of us would enjoy. Issues trusting people. Issues making real friends. Privacy. Even relationships with family became a thing because of this amount of wealth. Curious which of these things you’d jump on first.
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Jon Finkel
Editor-in-Chief, Midlife Male
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