From Faking It to Booking the Elite: The Journey of a Travel Concierge CEO

Jaclyn Sienna India established Sienna Charles, her boutique travel concierge service, in 2008, with the mindset of “faking it until making it.” At the time, she often found herself telling potential clients that her services were fully booked, despite having no actual clients. Sixteen years later, her strategy has paid off, as she now serves high-profile clients, including former President George W. Bush and celebrities like Mariah Carey, all of whom have annual incomes exceeding $100 million.

India emphasizes that her clients, who are typically powerful and well-connected individuals, often lack the time and creativity to realize their travel and dining visions. With a focus on personalization and genuine care, she leverages her extensive network within the hospitality industry, which includes over 2,000 relationships, to create unique experiences for her clientele.

She believes the value she provides lies in understanding her clients’ desires and executing them with precision. For instance, she often curates exclusive dining experiences, selecting venues that align with her client’s interests rather than merely opting for the most famous or luxurious spots. While she could easily secure reservations at renowned restaurants like French Laundry, she prefers to highlight lesser-known but more engaging alternatives, such as Single Thread Farms.

India’s services can include extraordinary arrangements, such as a candlelight dinner in Versailles or brunch on the Arc de Triomphe. She also facilitates interactions with influential figures, having organized breakfasts with the Hermes family and lunches with the Fendi family in Rome.

Sometimes, her clients seek simple comforts, as seen when she catered to George W. Bush during a trip to Ethiopia by providing him with peanut butter and non-alcoholic beer, along with a warm welcome from local children wearing Texas Rangers baseball caps. India prides herself on her genuine care for her clients, which extends to engaging with a diverse range of people throughout her day to ensure the experiences she crafts are not only luxurious but also authentically meaningful.

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