When Jaclyn Sienna India launched Sienna Charles, her travel concierge service, in 2008, she focused on projecting confidence even in the face of uncertainty. India recounted how her husband doubted her ambitions as they received inquiries from potential clients wanting bespoke travel experiences, despite her not having any actual clients at the time. She would often respond, “Oh, I’m sorry, we’re so busy, we’re really sold out this season with high-net-worth people.”
Fast forward sixteen years, India’s approach has proven successful. Her clientele now includes various influential figures, such as former President George W. Bush and pop star Mariah Carey. She exclusively caters to individuals earning over $100 million annually—clients already accustomed to luxury. So what does India offer that they cannot arrange themselves?
According to India, it comes down to genuine care and emotional intelligence. Drawing from her experience as a waiter, she understands the importance of personal connections and listening to her clients. This approach has been fundamental to her success.
Sienna Charles maintains an extensive network, often referred to as a “black book,” featuring over 2,000 contacts within the hotel, restaurant, and yacht industries. This wealth of relationships allows India to craft distinctive travel and dining experiences that go beyond mere luxury.
“My clients usually have a vision of what they want but lack the means to execute it,” India stated. “I’ve recognized that vision through brief conversations and have made it my mission to bring it to life.”
However, India’s aim is not just to secure her clients’ access to elite venues but also to ensure their experiences are meaningful. For example, while she could easily obtain reservations at the famous French Laundry in Napa, she prefers to recommend alternative experiences she believes are more engaging, such as Single Thread Farms.
Her bespoke services have led to breathtaking moments, including a candlelit dinner in Versailles and a brunch atop the Arc de Triomphe. India also arranges meetings with notable personalities on behalf of her clients, such as breakfast with the Hermes family and lunch with the Fendi family in Rome.
At times, her clients seek the comforts of home rather than extravagance. When arranging travel for Bush in Ethiopia, she ensured he found familiar foods like peanut butter and non-alcoholic beer, complemented by dozens of local children wearing Texas Rangers baseball caps.
“I genuinely care about people,” she shared. India dedicates her day to engaging with everyone around her—cab drivers, restaurant staff—to unearth compelling options for her clients. “The world is not just luxury; it encompasses everything, and my clients are interested in authentic experiences.”