In the era of the humble brag, it’s harder than ever to know how your boss travels. Assuming he or she is the type that likes to share, you might see a suggestion of a private jet or a swanky beach resort on Instagram—or hear one unassuming story about the sea turtles that swam under the paddleboard in St. Barthelemy.
Unfortunately for your water cooler conversations, no chief executive officer is ever going to spill the beans on his favorite private island, the extent of his security detail, or the lengths his assistant went to procure Coke Zero in Madagascar.
For that, we turned to Jaclyn Sienna India, president and founder of the decade-old travel consultancy Sienna Charles. Almost immediately after hanging a shingle on West Palm Beach’s ritzy Worth Avenue in 2008, India got her lucky break: An unexpectedly productive, $25 ad with the Explorer’s Club turned out her first billionaire client, and word of mouth turned one into many.
Now India is a go-to for the finance world’s jet set, regularly organizing trips for at least two dozen CEOs, along with other titans of industry and a handful of former U.S. presidents. Her clients range from Morgan Stanley higher ups and former top-level executives at American Express, to billionaires and real estate tycoons. Of the hundreds of trips she plans each year, 90 percent are for high-ranking finance types—some with budgets that climb into the millions. Chatting about restaurants, she says, is the best way to let these power brokers know she’s playing on their level.
“People can be all over the map,” she said, explaining that often clients are looking for a vibe or set of experiences rather than an exact destination. To help them wade through their options, she prefers face-to-face lunch meetings (typically at such power spots as Le Bernardin) over cursory phone calls. “A lot of agents can B.S. over the phone or have notes all prepared, but I could never do that. That’s not how you build up trust with the world’s wealthiest people,” she told Bloomberg.
Here’s what she had to say about her C-suite customers—the good, the bad, and the hyper-demanding.
A Private Jet Is a Business Expense
Private jets for execs and their families are almost always reimbursable corporate expenses. Why? Transportation is considered a matter of security, and most CEOs plan travel in tandem with work trips, taking their family with them to Dubai for a few days before jetting off to the Maldives.
“Safety” is a card more legitimately played by former presidents, says India, who has organized trips to Africa for George W. Bush and his 30 secret service agents. But CEOS are productive on planes—she joked that “if you can be offline for 10 hours, then you aren’t really that important.” (In the era of laptop bans, private planes are a good way to ensure that work gets done.)
Privacy also important. “CEOs like to stay under the radar and want to focus on their family rather than who they are,” India said. Speaking of family time: They often travel with their pets, “just because they can.”
Little else gets expensed. “CEOs can splurge big time on hotels, yachts, and experiences when they’re saving a minimum of $75,000 to transport a family of four,” India observed, noting the rough cost of a private jet.