In 2008, Jaclyn Sienna India launched Sienna Charles, a boutique travel concierge, with the mindset of “fake it until you make it.” At the time, she often found herself fielding inquiries from potential clients while lacking any real clientele. “My husband thought I was the dumbest person in the world because we would get calls from people saying, ‘Oh, I saw your article. I’d love to go to Disney,’” she recalled. Despite this, she would respond with, “Oh, I’m sorry, we’re so busy, we’re really sold out this season with high-net-worth people.”
Fast forward sixteen years, and India’s strategy has proven successful. Her clientele now includes influential figures such as former President George W. Bush and celebrity artists like Mariah Carey. Her services cater to clients earning over $100 million a year—individuals who seemingly have it all. So, what does India offer that her clients cannot achieve on their own?
According to India, the key lies in genuine care and understanding. “I was a server for five years before I started my business. I understand what makes people tick. And paying attention and caring about those people is paramount,” she explained.
Sienna Charles boasts an extensive network of over 2000 industry contacts across the hospitality sector, which allows India to create exceptional travel and dining experiences tailored to her clients. She noted, “[My clients] are explaining what they’re looking to achieve… but they just don’t have the tools, the time, the access and the creativity to be able to fulfill that.”
While securing entry into exclusive venues is part of her service, India emphasizes that the primary focus is on the quality of the overall experience. For instance, she prefers recommending unique dining experiences over well-known establishments, stating, “I don’t think French Laundry in Napa is really that exciting… Could we get somebody in there? Sure we can. But I think what they’re doing at Single Thread Farms down the road is far more interesting.”
India often creates memorable, bespoke events for her clients, such as a candlelight dinner at Versailles or brunch atop the Arc de Triomphe. She sometimes pairs meals with opportunities to engage with notable personalities, having arranged breakfasts with the Hermes family and lunches with the Fendi family in Rome.
However, her services can also cater to simpler desires. For example, when Bush visited Ethiopia, India made sure he had familiar comforts like peanut butter and non-alcoholic beer, along with a heartwarming welcome from local children wearing Texas Rangers caps.
“I genuinely care about people,” India said, noting that she engages with everyone from cab drivers to restaurant staff to discover the most interesting options for her clients. “The world is not just luxury. The world is not just fancy experiences. It’s everything and [my clients] want authentic experiences.”