Jaclyn Sienna India started her travel concierge service, Sienna Charles, in 2008 with a bold strategy of “faking it until making it.” Initially, she fielded calls from potential clients expressing interest in high-end travel experiences, despite having no actual clients of her own. “My husband thought I was the dumbest person in the world,” she recalled, explaining how she would tell callers that her firm was fully booked for the season, even though she was not serving any clients at that time.
Fast forward sixteen years, and her gamble has paid off. India now counts notable figures, including former President George W. Bush and celebrities like Mariah Carey, among her clientele. Her business caters to the ultra-wealthy, specifically those earning over $100 million annually.
India emphasizes that her approach is centered on care and genuine understanding. “My clients are more powerful and connected than I am, but that doesn’t mean they can get things done easily. It’s about leading from the heart,” she said. Drawing from her experience as a server, she understands the importance of personal connections and attentiveness.
With a vast network of over 2,000 contacts in hospitality, including exclusive yachts, hotels, and restaurants, India crafts unique travel and dining experiences that exceed mere luxury. She explained that her clients may have lofty objectives but often lack the necessary tools, time, and connections to realize their visions. “One of my gifts has been understanding that vision with only a few words, and then delivering that to them,” she noted.
While she acknowledges that high-profile venues are appealing, her focus leans towards providing authentic experiences. For example, although she could facilitate reservations at the renowned French Laundry restaurant, she prefers to recommend options that she finds more intriguing, like Single Thread Farms.
Her bespoke services have included extraordinary experiences, such as arranging a candlelight dinner in Versailles and brunch atop the Arc de Triomphe. India also seeks to create opportunities for her clients to meet influential personalities, having facilitated meals with the Hermes and Fendi families.
India sometimes caters to her clients’ more personal needs as well. During Bush’s trip to Ethiopia, she ensured he had familiar comforts like peanut butter and non-alcoholic beer.
“I genuinely care about people,” India shared, emphasizing that she engages with everyone, from cab drivers to restaurant staff, to curate the best options for her clients. Her mission extends beyond luxury; she aims to offer authentic experiences that resonate on a personal level.