When Jaclyn Sienna India launched Sienna Charles, her travel concierge service, in 2008, she initially pretended to be far more established than she was. Although early interactions with potential clients often left her husband skeptical—receiving requests from individuals interested in trips to Disney or New Jersey while she had no real customers—India persevered.
Now, 16 years later, her strategy of “faking it until making it” has proven successful. India’s clientele includes high-profile figures such as former President George W. Bush and celebrities like Mariah Carey, catering to those with annual earnings exceeding $100 million. This elite service is not merely about luxury; it’s about personal connection and understanding the unique needs of each client.
India emphasizes that while her clients are typically more influential than she is, what truly matters is the personal attention she provides. Her past experience as a server has helped her tune into what makes people tick, and she believes genuine care and attention to detail are essential attributes.
Sienna Charles boasts an extensive “black book” containing over 2,000 relationships within the hospitality industry, which enables India to craft unforgettable travel experiences. She helps clients articulate their desires, often transforming vague ideas into unique events that exceed their expectations. For instance, she discerned that some exclusive venues, like the renowned French Laundry restaurant, might not be as appealing as other lesser-known but innovative dining experiences.
India has arranged memorable experiences for her clients, such as a candlelight dinner in Versailles and brunch on the Arc de Triomphe. She often combines meals with encounters with industry luminaries, such as breakfasts and lunches with prominent fashion families in Europe.
However, India also understands when her clients prefer simpler comforts. For instance, when arranging travel for Bush to Ethiopia, she ensured he had familiar snacks like peanut butter and non-alcoholic beer, while also providing a warm welcome from local children.
India’s commitment to authenticity drives her approach. She engages with everyone from cab drivers to restaurant workers to uncover the best local experiences for her clients, asserting that the world encompasses much more than luxury—it’s about genuine, enriching encounters.