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April 14, 2024updated Apr 15, 2024

Oli Corkhill on His Lifelong Obsession with Skiing

The CEO of Leo Trippi reveals what it takes to craft an unforgettable alpine escape.

By Irenie Forshaw

When it comes to over-the-top requests, Oli Corkhill has seen it all. As the CEO of luxury alpine travel company Leo Trippi, he spends his days crafting bespoke skiing itineraries for his exclusive clients.

“There are two sides to extravagance,” he tells me with a conspiratorial smile over video call from his home in the Cotswolds.  “Sometimes it’s really experiential, based entirely on what they’re going to do – so, for example, we had a client in Iceland request to have a bonfire and firework display at the top of a volcano before night skiing back down.”

He pauses for a moment before adding: “Then we get requests like the client who asked to replace the marble in the bathroom of their chalet for a week-long stay – because they wanted a different color.”

[See also: The Best Alpine Ski Resorts to Visit]

leo trippi helicopter
Corkhill is in the process of weaving together an unforgettable heli-skiing trip / ©Leo Trippi

Corkhill has spent years honing his craft and it’s clear that creating these unforgettable trips is far more than just his day job; it’s his passion. “Obsessed” with skiing for almost as long as he can remember, the CEO spent his childhood traveling the world. His father worked in the oil industry and the family moved regularly, spending stretches in Norway, Azerbaijan and Dubai.

But it was his summer holidays in Switzerland that sparked his love of skiing. By the time he was nine, Corkhill was living in Liverpool (the family’s ‘UK home base’) visiting the local dry ski slope whenever he could. “I became completely addicted,” he grins.

When an instructor suggested he should ski with legendary freeride skier Warren Smith, Corkhill leaped at the chance. At just 13, he traveled to Tignes in the French Alps and spent a couple of weeks at Smith’s summer camp. “There were a lot of jumps, tricks and 360s,” he says. “Going fast, challenging yourself, feeling a little bit on the edge… I fell in love with it.”

Leaving the slopes behind was always a struggle. In total, Corkhill was asked to leave six English boarding schools. “I think it was because I was bored and didn’t feel challenged,” he explains. “I was a bit of a class clown. I’m not necessarily proud of this stat but I think the longest I lasted was about 18 months – the shortest was two days.”

leo trippi skiing in alps
Leo Trippi crafts bespoke travel itineraries for clients / ©Leo Trippi

At 16, he moved to Verbier where Smith was based. His parents let him go on the agreement he could “get it out of [his] system” and go back to school the following year. But when Corkhill returned to the UK to start his A-levels, he found it hard to adjust. “I think I lasted about seven weeks before I went back to Verbier,” he says with a sheepish grin. This time, he completed his ski instructor qualification with Smith before coming back to the UK to give school one last try. He made it to the two-month mark before throwing in the towel for good. Skiing, he realized, was his future.

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Back in Verbier and working as a ski instructor, Corkhill and his friend began toying with the idea of starting their own business. They finally settled on renting chalets and invested just £100 between them to set up Alpine Guru. The first few years were exceptionally tough; the two friends did everything themselves from the website and branding to writing each of the property descriptions.

Corkhill began working offshore in the oil industry to make ends meet. The ambitious entrepreneur would spend five-week stints at sea assisting with exploration voyages to map the ocean bed in search of oil deposits. His job was to monitor the surrounding waters to ensure there were no marine mammals in the vicinity of the boat when seismic airguns were fired.

“Normally I was doing acoustics so I would just sit there for hours at a time with the headphones on,” he recalls. Unless there was a sighting, there wasn’t much to do so he was able to work on his business in any spare moments he could snatch. Over the next four years, Corkhill traveled around the world from Angola to the coast of Ireland until, finally, Alpine Guru began making enough money for him to take a proper salary.

[See also: Alex Assouline on Bold Ambitions for His Family’s Luxury Publisher]

leo trippi helicopters in the alps
Everything is taken care of from ski instructors to helicopter transfers / ©Leo Trippi

It wasn’t long before Corkhill got a call from Auret van Zyl, one of the founders of Leo Trippi, asking whether he would be interested in selling Alpine Guru and joining the luxury travel company. “I basically went back and said no,” says Corkhill. “I didn’t like the idea of going from completely controlling my own destiny to working for someone else and having other people to answer to.”  

But after further discussions with Van Zyl about retaining his autonomy, Corkhill and his business partner eventually decided to go through with the deal. In 2016, Alpine Guru was acquired by Leo Trippi and, within 18 months, Corkhill was made CEO.

Today, he continues to work with the travel company’s top clients, matching them with the planet’s most exclusive chalets and crafting bespoke itineraries. Everything is taken care of from ski instructors and helicopter transfers right down to ensuring the property is stocked with guests’ favorite drinks.

Occasionally, Corkhill tells me, it’s necessary to challenge his clients’ demands. “Everybody gets in contact saying they want a ski-in/ski-out chalet,” he says. “The reality is that it’s nice to have but it may be that the chalet only has that type of access for advanced skiers and [the client] is only intermediate so actually it would be very uncomfortable. We really try to articulate to people which types of chalets would actually work for their type of group configuration.”

heli-skiing Antarctica, leo trippi
Requests are growing for heli-skiing trips to far-flung locations like Greenland and Antarctica / ©Leo Trippi

In late 2021, together with his business partners Van Zyl and Florian Steiger, he set up Viadi Group, a global luxury vacation rental platform. So far, they’ve acquired several high-end travel businesses including Edge Retreats and Explorations Company.

His work certainly keeps him busy, but Corkhill shows no signs of slowing down. As well as continuing to build Viadi Group’s portfolio, he is in the process of weaving together a Swiss heli-skiing trip for one of his clients at Leo Trippi. Increasingly, he says, requests are growing for superyacht-based heli-skiing trips to far-flung locations like Greenland and Antarctica.

Crucially, the team tries to “inject some sort of wow moment” into every trip. This could be something quite humble like a husky ride with hot chocolate, or, for the higher-end clients, a private yodeling performance in the mountains. Whatever it may be, the idea, Corkhill tells me, is to create an experience that “speaks to people and touches their emotions.”

[See also: Ben Goldsmith on Philanthropy, Rewilding and His Critics]

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