Oliver Corkhill
CEO of Leo Trippi
Co-founder of Viadi Group
Oliver Corkhill is one of the names that sticks out the most in the upscale tourism sector. The CEO of Leo Trippi and co-founder of Viadi Group, Corkhill is a visionary leader whose passion for skiing and determination have driven him to become an industry leader in bespoke travel experiences. His journey, however, was not a smooth one. From a rebellious childhood to becoming a respected entrepreneur, Corkhill’s story is one of persistence, innovation, and unwavering dedication to creating memorable and transformative experiences for his clients.
Struggle and Early Days
Corkhill’s love for skiing began in his childhood, a passion that would ultimately shape his professional career. Growing up in a family that moved often due to his father’s work in the oil industry, Corkhill’s global exposure provided him with diverse experiences. However, his schooling years were marked by restlessness and defiance. Corkhill was expelled from six different boarding schools in the UK, never quite fitting into the structured academic environment.
Despite the disruptions, his love for skiing persisted. Corkhill found solace on the slopes, spending his teenage years mastering the sport. His move to Verbier at 16 was a turning point, where he fully immersed himself in skiing, even completing his ski instructor qualifications. Though his parents expected him to eventually return to a more conventional path, Corkhill was resolute in his decision to turn his passion into a career.
Entrepreneurial Journey and Alpine Guru
Corkhill’s first venture into entrepreneurship began with Alpine Guru, a chalet rental business he co-founded with a friend. With just £100 in initial investment, Corkhill and his partner handled everything from website design to property descriptions. The early years were tough, and to make ends meet, Corkhill worked offshore in the oil industry. He balanced his entrepreneurial efforts with five-week stints at sea, leveraging any free time to develop Alpine Guru.
After four years of grueling work, Alpine Guru finally began to turn a profit. It was during this time that Corkhill received an offer from Leo Trippi, a luxury travel company, to sell Alpine Guru and join their team. Although initially reluctant to give up control of his business, Corkhill eventually saw the opportunity to scale his impact without sacrificing his autonomy. The acquisition marked a new chapter in his career.
Leadership at Leo Trippi
In 2016, Corkhill became the CEO of Leo Trippi, a move that solidified his position as a leader in the luxury travel sector. Known for crafting bespoke alpine itineraries for high-end clients, Corkhill’s approach combines meticulous attention to detail with a deep understanding of his clients’ needs. His leadership is characterized by a focus on personalization and creating unforgettable experiences, from private yodeling performances in the Swiss Alps to superyacht-based heli-skiing trips in Greenland.
Corkhill is not only passionate about luxury travel but also committed to ensuring that each trip includes a “wow moment” that touches clients emotionally. His ability to blend extravagance with deeply personal touches is what sets him apart in the competitive world of luxury travel.
Strategic Vision and the Viadi Group
Corkhill’s vision extends beyond Leo Trippi. In 2021, alongside his business partners, he founded Viadi Group, a global luxury vacation rental platform. The group has since acquired several high-end travel companies, including Edge Retreats and Explorations Company. Corkhill’s strategic approach to scaling the business while maintaining quality has been instrumental in Viadi Group’s success. He continues to seek new opportunities, focusing on expanding the group’s portfolio and innovating within the luxury travel sector.
Wrap-Up
Oliver Corkhill’s rise from rebellious schoolboy to CEO of a global luxury travel brand is a testament to his determination, passion, and strategic thinking. His leadership at Leo Trippi and Viadi Group showcases his ability to blend creativity with business acumen, crafting unique and transformative experiences for his clients. In a world where luxury is often synonymous with opulence, Corkhill stands out for his commitment to creating experiences that are not only extravagant but also meaningful. His journey serves as an inspiration for aspiring entrepreneurs, showing that passion, when combined with perseverance, can lead to extraordinary success.
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