Almost every year since 1996, a man and his family chartered a yacht at least once. Often, they booked two or three times a year. The man’s best guess is that he did 30 or 40 charters overall before buying the 164-foot (50-meter) Westport Trending about two years ago.

“In the end, I finally succumbed to the wishes of my family,” says the owner, who asked to remain anonymous. “My wife wanted it more than I did. I’m a finance guy. I know that it’s impractical.”

All of the family’s experience has gone into the charter program aboard Trending, which books through Camper & Nicholsons International. Here are edited excerpts from my conversation with the owner about how he approaches charter as a business.

How did being a charter client prepare you to become a charter-yacht owner?

We’ve heard that we’re the most active charter guests that anybody ever has. We dive once or twice a day, we use Jet Skis like crazy people, we’re happy to swing off a rope swing into the water, we’re happy to use any toys underwater, we love to do dress-up parties, we’ve had Olympic kind of games around the boat with contests and things, and we love to go out. And we go in different directions because we’ve historically traveled with another family whose kids are of similar age. All while they were growing up, when they were about 6 to 16, we’d charter boats all the time, and there were always 10 or 12 of us, and we’d use every single thing, every paddleboard and kayak that the boat has, and we’d be doing all kinds of things but not at the same time.

Being active like that all the time is a real workout for the crew that they’re not necessarily used to, and after all those charters, you start to be a little picky.

When it came time to choose your own crew, how did you do it?

I had a cheat sheet. When my kids were growing up, we had a logbook of every vacation we took, every time we went to Aspen or Vail (in Colorado) or took a vacation on a boat. I would log each person’s name and a little something about the person. If you go through the logbook and the same name appears three or four or five times, it’s easy to see, ‘Oh, yeah, we loved her.’

The best captain that we ever had on any of our charters, and we had him several times, was Randall Petersen [on the 155-foot Christensen One More Toy]. As soon as I got my boat, I called Randall and said, ‘Please come and be my captain.’

Today, Petersen is one of two captains who rotate aboard Trending, right?

He has 8- or 9-year-old girls and a wife, and he asked to go on rotation. If you’re married, you need to go home or else you’re going to get divorced. I was happy to let him do rotation, and I thought back of who were our other crew people, and on [the 135-foot Christensen] Atlantica, that was awesome when my kids were little. Yan Kunst was the first mate, I think, and his now-wife was the person in charge of fun. All the kids learned to dive with Yan’s wife. We loved her. So I called Yan and asked if he wanted to do a rotational thing, and he also had young kids, so I figured two captains, two sets of young kids.

You approach crew training differently than most charter-yacht owners.

I learned while chartering that if the first mate who drives the tenders is not available, you’re not getting off the boat. That’s no good. So I melded that with my high-tech management experience about training, working as a team, doing reviews, keeping people happy. What’s great about our two captains is that they know, though they’re the boss, they can mix a drink if pressed. Their boys are all trained for our multiple tenders. Any boy can drive all three of those tenders, so we can all go off and do our different things.

The internal job-sharing concept, what sometimes happens is that one of the stewardesses or one of the boys, the customers take a liking to them. So pretty soon, he’s out of work because he’s stuck with customers. And being stuck with customers is the best thing—he’s bringing them out on dives, he’s out on the boat, they’re asking for him all the time—but pretty soon the other boys have to cover for him on his cleaning duties or whatever, and that’s what we try to instill in everybody. All we care about is whatever the customer wants. If the customer wants a pretty boy to work with, we’re going to give them the pretty boy. If the customer really likes the third stewardess and wants her to bring them tea in the morning, then that’s what’s going to happen, and the second stew, dammit, will do laundry and make beds.

You also invest in each crewmember’s personal ambitions.

My chef, he’s just a crazy food maniac. Since he’s really crazy about food, I thought, Well, Charlie, what can I do for you when you’re not working? And he said, “How about sushi training in Japan?”

It’s really not that much money. Maintenance and fuel on the boat cost so much more than a few thousand dollars that will benefit his career and let us offer more on charter. So he went there, and then I sent him to Napa, California. He would go to the French Laundry restaurant. He furthered his wine knowledge—and it’s great. People love it, and we love it.

It’s rumored that you spare no expense on maintenance and upgrades aboard Trending.

I’m a freak. My father was a plumber, so we grew up in a union household. My father maintained all of our stuff so that we never had to buy new stuff. I was lucky enough to make a great living, and I became similar. When my wife and I got married, we built a house in 1993, and it’s a Queen Victorian thing. Our entire marriage, we’ve maintained the hell out of that thing.

I also have a 2007 [Chevy] Suburban. I use it to haul snowmobiles and haul my smaller boats around the Cape [in Massachusetts]. I keep it in showroom condition, and that’s the way it will be.

It’s the same thing with the yacht. I’m going to have that damn thing for 30 years, until I die. It’s a 2006, I think, and I don’t care. When it needs a new engine, it’s going to get a new engine. When it needed different anchors, it got new anchors. It needed that bridge-deck level extension so we could seat 12 guests and keep them away from the riffraff on the docks of Monte Carlo, so, okay, we’re doing that bridge-deck extension. It’s awesome eating up there.

You’ve invested in a lot more than the bridge-deck extension, right?

Sun is out for us. We need shade. We’re not going to die of cancer. So we have extra shades that we can put in and take out, extra umbrellas. And the Jacuzzi—who likes those stupid little round Jacuzzis? Get that out of here. We got the biggest-ass Jacuzzi we could find, one of those Michael Phelps things. And what else do you do there? You booze, so we put a little bar on one side of it with stools that are awesome.

Some people are music freaks, including me, so we have this music stuff where I can play the music on my phone, the video and audio on all the TVs and stereos on all the floors.

We also knew, from all our chartering experience, what the sky-lounge bar area had to be like, with a big bar and TV and games so you can dance and stuff. We knew the bridge-level dining was so much nicer than being under a roof. We can see the sky on the higher deck.

And we knew, when it came to tenders, that we needed a bunch so people can go off and do their own thing. It’s the best thing, at 5:30 at night, to be in the 37-foot Boston Whaler, which has a dive door, and you can have some drinks and shrimp cocktail—people need to understand that at sunset, you need to get your ass on that tender and go putt around some cove. It’s awesome.

What has been the biggest challenge in moving from charter client to charter-yacht owner?

Getting the crew to do things for themselves. We’ve had some yard periods, and it’s so hard to get them to upgrade their own cabins and the crew mess. It’s pulling teeth to get them to put granite in their sink area. Come on, kids, do something nice for yourself!

And we’ll try things and throw them away. That comes from my high-tech background. Sometimes you invest and then the product’s a dud. The crew knows that if something ain’t working, the boss says we can throw it away and start new. I’m good with that.

For more information: camperandnicholsons.com, or any charter broker