From Rags to Riches: The Rise of a Luxury Travel Mogul

In 2008, Jaclyn Sienna India launched Sienna Charles, her luxury travel concierge service, with the philosophy of “fake it till you make it.” At the beginning, she had no clients but managed to convince potential customers that she was overwhelmed with high-net-worth individuals seeking her services.

Fast forward sixteen years, and India’s strategy has proven successful. She now counts prominent figures, including former President George W. Bush and celebrities like Mariah Carey, among her clients. Sienna Charles caters to individuals earning over $100 million annually, providing access to exclusive experiences they cannot easily arrange themselves.

India emphasizes that her approach centers on genuine care and understanding, honed during her years as a server before starting her business. She believes that building relationships, or her “black book” of over 2,000 connections in the hospitality sector, is vital for crafting unique travel and dining experiences.

She strives to not only grant access to the most exclusive venues but also to ensure that the experiences are meaningful. For instance, while some may consider French Laundry in Napa a highlight, India prefers to showcase what she deems more interesting options, like Single Thread Farms.

Her service often includes extraordinary arrangements, such as organizing a candlelit dinner in Versailles or brunch on the Arc de Triomphe. India also makes an effort to connect her clients with notable personalities, having facilitated meals with families such as Hermes and Fendi.

Sometimes, her clients’ requests are more straightforward, as demonstrated when she ensured that President Bush had familiar comforts like peanut butter and non-alcoholic beer during his visit to Ethiopia. India believes that authentic experiences, rather than just luxury, are what her clients truly seek. She invests time in getting to know everyone involved in her clients’ journeys to provide them with memorable and unique experiences.

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