In 2008, Jaclyn Sienna India launched Sienna Charles, her travel concierge service, determined to navigate the business landscape despite having no clients. “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,’ or ‘We’re going to New Jersey for the weekend,’” India recalled. “I had to respond, ‘Oh, I’m sorry, we’re so busy; we’re sold out this season with high-net-worth people.’”
Fast forward sixteen years, and India’s strategy of “faking it until you make it” has paid off immensely. Her clientele now includes high-profile figures like former President George W. Bush and numerous celebrities, all earning over $100 million annually. So what unique offerings does India provide that her clients can’t secure themselves?
India believes that while her clients may hold significant power and connections, it’s genuine care and attention that create lasting experiences. “I was a server for five years before I started my business. I understand what makes people tick. Paying attention and caring about those people is paramount,” she stated.
Sienna Charles features an extensive network, boasting over 2,000 relationships within the hospitality sector, including upscale hotels, yachts, and fine dining. This web of connections allows her to curate exceptional travel experiences for her clients. “My clients already envision their desired experiences; they just lack the tools, time, or creativity to achieve them,” she explained. “One of my gifts has been understanding that vision with only a few words and then delivering it.”
Rather than simply focusing on obtaining access to elite venues, India prioritizes the quality of the overall experience. For instance, she doesn’t promote the three-Michelin-star restaurant French Laundry in Napa because she feels other experiences, like Single Thread Farms, are more captivating.
India frequently arranges unique events for her clients. She has organized a candlelight dinner at Versailles and brunch atop the Arc de Triomphe. “We also like to pair meals with meetings with notable personalities,” she mentioned, highlighting previous arrangements with the Hermes and Fendi families.
Sometimes her clients seek simpler comforts. For example, during a trip to Ethiopia with Bush, she made sure he had his favorite snacks—peanut butter and non-alcoholic beer—and arranged for local children to greet him wearing Texas Rangers caps.
“I genuinely care about people,” India emphasized. She makes it a point to engage with everyone she encounters, from cab drivers to restaurant staff, to source interesting options for her clients. “The world is not just luxury. It’s everything, and my clients seek authentic experiences.”