New York — 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 favourite 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, $25,000 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 fina...

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