When Jaclyn Sienna India launched Sienna Charles, her travel concierge service, in 2008, she was committed to projecting success even before it materialized.
Initially met with skepticism from her husband, who doubted her ambitions due to her lack of clients, India would respond to inquiries suggesting a depth of business that didn’t yet exist. “We’d receive calls from individuals wanting advice on trips, and I would say we were fully booked with high-net-worth clients,” she recounted.
Fast forward to today, sixteen years later, and India’s strategy of “faking it until you make it” has led to remarkable success. Her client roster now includes notable figures, such as former President George W. Bush and celebrity icons like Mariah Carey. Her clientele consists of individuals with annual incomes exceeding $100 million, requiring services that go beyond their own means.
India explains that her role is not merely about facilitating luxury, but about providing thoughtful, tailored experiences. “My clients may have more power and connections, but what matters is the care and attention I put into their needs,” she stated. Drawing from her experience as a server, she emphasizes the importance of understanding people and nurturing those relationships.
Sienna Charles benefits from a vast network of over 2,000 contacts within the hospitality sector, which allows her to curate exceptional travel and dining experiences for her clients. “They often have a vision for their experience, but lack the tools or time to realize it. My gift is interpreting that vision and making it a reality,” India noted.
Her focus is on delivering meaningful experiences rather than just accessing exclusive venues. For instance, while she could arrange a reservation at the renowned French Laundry in Napa, she believes alternatives like Single Thread Farms offer more intriguing dining options.
India frequently organizes unique, once-in-a-lifetime events for her clients. Her service has facilitated intimate dinners at iconic locations such as Versailles and brunches atop the Arc de Triomphe. She often coordinates meals with prominent personalities, such as arranging a breakfast with the Hermes family and lunch with the Fendi family in Rome.
On occasion, her work leans towards simpler comforts. During Bush’s trip to Ethiopia, she ensured he had familiar foods like peanut butter and non-alcoholic beer, and arranged for local children to greet him wearing Texas Rangers baseball caps.
“I genuinely care about people,” India explained, highlighting how she engages with everyone from cab drivers to restaurant staff to discover the best options for her clients. She believes that authentic experiences encompass more than just luxury — they are about genuine connections and unique moments.