When Jaclyn Sienna India established Sienna Charles, her travel concierge service, in 2008, she was committed to projecting confidence even when she was starting from scratch. At the time, her husband doubted her ambitions as they received inquiries from potential clients interested in luxury vacations like trips to Disney or weekends in New Jersey, despite her having no actual customers to serve.
Fast forward sixteen years, and her initial strategy has proven successful. India now caters to high-profile clients, including former President George W. Bush and celebrities like Mariah Carey, all of whom possess fortunes exceeding $100 million. Her clientele typically includes individuals who have access to virtually everything, prompting the question: What does Sienna Charles offer that they cannot arrange themselves?
India believes her competitive edge lies in her genuine care for her clients. Having spent five years working as a server, she developed a keen understanding of people’s needs. She emphasizes that attentiveness and compassion are fundamental to her approach. Today, Sienna Charles has cultivated a vast network, referred to as her “black book,” that includes over 2,000 contacts within the hospitality sector, covering everything from yachts to luxury hotels and fine dining.
She articulates that her role involves translating her clients’ abstract desires into tangible experiences. “My clients come with a vision but may lack the tools, time, or creativity to bring it to fruition,” she said. “Part of my talent is grasping that vision quickly and executing it effectively.”
Importantly, India focuses not just on securing exclusive reservations but also on ensuring that the overall experience is meaningful. For example, she believes that renowned restaurants like the French Laundry aren’t always the best options for her clients, instead favoring places like Single Thread Farms for their unique offerings.
India also prides herself on creating bespoke experiences. She has arranged special occasions such as candlelight dinners in Versailles and brunch on the Arc de Triomphe. Furthermore, she often integrates authentic encounters with notable figures into her clients’ itineraries, having facilitated meals with prominent families like Hermes and Fendi.
At times, her clients’ requests lean towards the more familiar. When arranging a trip for Bush to Ethiopia, she ensured he could enjoy comfort foods like peanut butter and non-alcoholic beer while also coordinating a warm welcome with local children dressed in Texas Rangers caps.
“I truly care about people,” India said, underscoring her commitment to understanding both the luxurious and the authentic aspects of life. She dedicates her time to connecting with everyone around her—from taxi drivers to staff at restaurants—to discover the best and most authentic options available for her clientele.