Roy Carroll's company builds apartment buildings, self-storage and hotels in six states. It started small: his father, a meat cutter at a Greensboro, N.C., grocery store, was laid off in 1983, and father and son began building houses together; Roy bought out his father's share in 1990. Keep that in mind reading Nancy Keates's tour, in Friday's Mansion section, of the $20 million house he built at Montana's Yellowstone Club, because the best line in it isn't about the life-size wax John Wayne at the bar. It's the one condition he put on his three grown daughters when he let them design their own suites: anything you want, as long as it's on budget.
He didn't go to Montana to build. A friend pointed him to the Yellowstone Club, the 15,200-acre private ski community near Big Sky that's drawn Bill Gates, Mark Zuckerberg and Shark Tank investor Robert Herjavec. Skiing with no lift lines sold the daughters, now 31, 34 and 36; Roy and his wife, Vanessa, wanted a place where the whole family could stay under one roof. The lot that clinched it — 3 acres, ski-in, ski-out, $4.5 million in 2018 — had everyone pushing him to buy. "They were smitten," Roy says. What followed was a 12,800-square-foot, eight-bedroom house, finished in 2022 and designed by Bozeman's Locati Architects & Interiors: siding reclaimed from old horse corrals, a rec-room saloon copied from the club's Boot Room, and a wine cave built to look like a mine shaft, opening onto a vaulted room of antique bricks from a bar in Pony, Mont., population 127.
Carte blanche, with a ceiling
The lead designer says no two rooms are alike. Each daughter got a suite — bathroom, walk-in closet, fireplace — and free rein on the look, with one instruction from her father: whatever they wanted, provided it stayed on budget. He wanted them to feel ownership. So Hayleigh, the youngest and a lawyer, got black-and-white with an iron bed; Madison, director of hotel operations for the family company, went Montana equestrian; Brittany, the oldest, who works in social media, chose taupes and creams. Roy ordered two bunk rooms, one for girls and one for boys, with grandchildren in mind; two have arrived and two more are expected. Nooks like the reading spot under the stairs are there so people can get away from each other. "Out here, you can't just get in a car and drive home," he says.
And this isn't the only build. In Greensboro, home to all five Carrolls, a lot bought for $4.5 million in 2024 is getting three houses, one for each daughter (a different $4.5 million lot from the Montana one; the Journal doesn't say whether the $20 million includes the first). Still, Montana is the family's main gathering place, with at least two weeks planned there every summer and every winter. "Anything that brings the family together is worthwhile," Roy says.
Our read
File this under Estate, with Housing (M6) in the margin. The plan is on the page; the question isn't. The plan: equal treatment — three suites, three houses, one each — and a budget. Do what you like within the budget is how a family teaches money without a lecture; the daughter who blows hers on a chandelier learns something, and nobody's sore at Thanksgiving because the rule was the same for all. The question: the Journal says nothing about how the Montana house is titled, who pays the taxes and upkeep after the parents are gone, or what happens when one daughter wants out and two don't. A shared vacation house is one of the assets most likely to split a family — less over money than because nobody wrote the rules while the one person who could was around.
Hold, obviously — a $20 million ski house isn't a model for anyone's portfolio. The model is the method — a budget, equal shares — plus the piece the paper doesn't show: operating rules settled while the builder's still around. If your family has a cabin, a lake house or a condo the kids will share, the review is where that goes on the list, for an estate attorney to put in writing. The umbrella gets bought on a dry day; so does the operating agreement.