Repeat after me: Experience is not expertise. Your average watch collector doesn’t presume that a cabinet full of high-end timepieces makes him a watchmaker any more than automotive enthusiasts believe that piloting a Ferrari Enzo or a Pagani Utopia in the garage makes them a car designer. But it seems that it’s much more tempting to turn a lifetime of luxury hotel-hopping into self-proclaimed know-how.
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There’s nothing wrong with speculating on a hospitality property, just as one would on any other real-estate investment. The Ritz-Carlton on New York City’s Central Park, for example, came up for sale earlier this year, with the 250-room property valued at approximately $400 million; investing in such a thriving business is an easy decision. But there’s a veritable chasm between being rich enough to buy a hotel and being savvy enough to run one. If only every owner recognized that.
This is an issue I’m increasingly seeing at five-star properties around the world—places with so much potential to impress, each falling short for the same reason: a bad case of owner-itis, an emerging condition whereby the deep-pocketed get in too deep with the day-to-day.
Take one Mediterranean hideaway that I was desperate to love, a cluster of exquisitely designed villas on one of the most exclusive islands in the region. “I’ve been open two years, and I’ve already gone through four general managers,” the owner sniffed over cocktails during my first night. “You can’t get staff who will do what you tell them.” She didn’t see that the common thread running through those problems was not the staff. I did, though, and four days later I checked out following one of the most dispiritingly underwhelming experiences I’ve ever had.
I recently toured another hotel, a wealthy couple’s design-centric passion project tucked away in the South African countryside, brimming with gloriously quirky touches. (For one thing, the chickens live in a shack lit by a chandelier.) One of the owners explained that it would be a ritual, rather than a vacation, to stay there: Anyone who wished to book a room must commit to four nights minimum to fully immerse themselves, or their request would be declined. Would-be guests were treated more like lab rats, requiring those paying for their service to bend to these arbitrary rules. Needless to say, within months of opening and with bad word of mouth building, such strictures were abolished. But the hotel’s reputation has never soared.
Another entrepreneur welcomed me to a private island in the Caribbean rostered by a slick, professional staff able to cater to any whim. The only irksome presence was the owner herself, whose hosting skills were more Basil Fawlty than Ian Schrager. Whenever I stepped outside, she would appear next to me like a gawky Candyman, radiating an awkward bonhomie. Then there’s the individual who snapped up a world-renowned hotel chain and installed himself in a residence at one of its priciest flagships, in an attempt to be more hands-on. The result? Staff members vibrating with anxiety, precluding them from focusing fully on the guests.
And spare a thought for the team at one smaller worldwide ultra-luxury chain owned by another ultra-high-net-worther, who flits between his holdings and upends operations wherever he’s in residence. He inherited his wealth, so it’s strange that a childhood spent in suites like this didn’t make him a better guest. He sleeps and wakes as he wishes, perhaps breakfasting at 4 p.m. and eating dinner at 6 a.m., so any dish on the room-service menu must be ready to deliver within minutes. The result: The entire kitchen brigade must keep cooking 24/7, discarding and replating a meal as soon as it’s cold.
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It seems to be easier to own hotels and make them thrive, though, if your wealth is derived from hospitality. The Sersale family, who run Positano’s Le Sirenuse , for example, became rich precisely because of their innate talents in running a hotel. Experienced interior designers, too, have relevant skills. Look at Karen Roos, a former magazine editor who’s married to one of South Africa’s wealthiest men, Koos Bekker. The chic aesthetic of their passion project, Babylonstoren , near Cape Town, is entirely her conceit—and helped make it one of the world’s buzziest luxury hotels. And, of course, the man who regularly trades places with Elon Musk as the world’s wealthiest, moved into hospitality in 2006. Bernard Arnault launched Cheval Blanc under his LVMH umbrella before bolstering that offering with a $3.2 billion acquisition of Belmond five years ago. He might stay in them as he wishes, but they’re operated by a crack team, like any brand—from Dior to Veuve Clicquot—in that stable.
But owner-itis is rampant, and perhaps one property epitomizes it more than any other. Several years ago, tech entrepreneur Rameet Chawla snapped up a historic 252-acre farm in upstate New York’s Hudson Valley, one of the newest hot spots for high-end hotels. He planned to turn it into a property with a difference: His would be a “secret hotel,” with sparse roadside signage and a website without images or information. He wanted to curate his paying guests, keen to make the experience so exclusive that the wealthy would scramble for the privilege of staying at his inn. Visitors would book by word of mouth—the “right types” would have to call to request the chance to stay. “What becomes more interesting is the thing you don’t have access to,” he said with preening confidence after it opened.
Unfortunately, his target market disagreed. The property was too hard to book—and to find—and most locals scoffed at the amateurish idea that a hotel could thrive when purposely hidden. Barely a year after the Dutchess opened, Chawla’s inexperience proved fatal, with the property reportedly selling in a distressed transaction in 2021. The new buyers quickly flipped it, selling that huge tract to IHG subsidiary Six Senses , the spa-focused five-star operator with sites around the world.
In a rare move, Six Senses spent $13.75 million in an off-market deal to buy the land rather than simply operating the property on an owner’s behalf—the typical model for mainstream hospitality today. Expect it to thrive once that professionally operated site opens. . .as long as it isn’t sold to another wealthy hotelier wannabe, that is.
British-born, New York–based Mark Ellwood, Robb Report ’s editor at large, has lived out of a suitcase for most of his life but has not bought a hotel (yet).
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