Super Agent: Jaclyn Sienna India Sells Luxury To The Elite

Jaclyn Sienna India, and her husband, Freddy Charles Reinert.

Jaclyn Sienna India has come a long from getting fired on a nightly basis from a job hosting at Le Fin Bec, a five-star Philadelphia restaurant, a little over 10 years ago. 

In between preparing for her first trip to Cuba and another to Spain and Portugal the week after, India recapped how she went from being a part-time hostess and art history student at the Tyler School of Art at Temple University to co-owner of one of the most successful luxury travel agencies in the country. Today the business she and her husband Freddy own, Sienna Charles, does between $5 million and $10 million in sales each year. She and her team of four have arranged travel for actors, NBA players, and a former president. 

“I had one of those psychotic screaming bosses,” she said. “I used to get fired every night—I would leave out the front door and come back in the front door.” 

She found her footing when she and her husband left Philly and moved to Florida, and she got a job at a traditional brick-and-mortar travel agency. Taking advantage of her experience at Le Fin Bec, she saw an opportunity.  

“I never understood how travel agents were booking all kinds of luxury stuff when they had never been there,” she said. “They were being trusted by these wealthy clients and the service had been lost. The service at the restaurant was far greater.”

So India decided to sell only ultra-high-luxury vacations—and to do that successfully, she was going to have to experience that kind of travel for herself. She left that agency and started her own—and she began on the road. 

Over the next four years, she and Freddy visited 50 countries, staying at high-end properties and eating at five-star restaurants. To get by, the two of them “literally did whatever it took to get the knowledge and feel good about ourselves,” she said. They AirBnB’ed their apartment an dimmersed themselves in the lifestyle of the rich and famous, seeing how luxury clients are treated, what magazines they read, what they’re looking for in a vacation. 

“You have to know how they think, how they act, what they do,” she said. “You have to know their spending patterns so well.” 

Then she started to look for potential clients, writing to the press to get the word out about her business and her travel experience. She got her first bite when a billionaire from Texas read an article about the places she had gone and hired her to arrange a trip. That one sale got her business started. Referrals started to roll in and the labor of love began to pay off. Other wealthy people—NBA player, actors—started to call. 

On one trip where she and her husband brought President Bush, his wife, a number of their friends, and 30 secret service agents to Ethiopia to live with remote tribes. 

The trip required charter jets and seven helicopters.  “He loved it, he has such an affinity for the African people,” she said. 

Today India sells only high-end luxury, which means no coach tickets, nothing to which the agency can’t add value, and nothing she hasn’t experienced firsthand and can’t recommend personally. 

Her brand reflects that experience, as well. No matter what the clients get from the Sienna Charles—from pamphlets to the agency’s office—it is designed with luxury in mind. 

“Everything we push out takes so much time and is beautiful,” she said. 

And that’s her advice to other agents: know what you’re selling, have a stake in your clients’ vacations, find out what works for you and dedicate yourself to it. 

“It’s really easy to lose your identity,” she said.  “Know who you are and stick to your guns.” 

As for her position now, she recognizes that things have come full circle since her time at Le Fin Bec. “Now I’m the psychotic screaming boss,” she said.