If you stumbled across a dusty, 200-year-old bottle of French Bordeaux in a European basement—supposedly owned by Thomas Jefferson himself—you might think you’ve struck gold. In the world of high-end wine collecting, single bottles from the 18th and 19th centuries routinely fetch anywhere from $50,000...

In an era where tech CEOs drop $50,000 on skeletonized Swiss chronographs and hedge fund managers flaunt custom platinum Audemars Piguet Royal Oaks, a bizarre phenomenon sits quietly on wrists all over the world: billionaire entrepreneurs, Hollywood A-listers, elite military operators, and hardcore horology snobs...