When Ray Dalio was eight years old, his jazz musician father, Marino Dallolio, moved the family from Jackson Heights, Queens, to Long Island. Like many kids, young Ray had a paper route and did odd jobs around the neighborhood, mowing lawns and shoveling snow for pocket money. When he was 12, he began caddying at a nearby golf club.
The club’s membership included quite a few Wall Streeters, and having become interested in the market from what he’d overheard on the links, Ray bought 60 shares of Northeast Airlines with $300 he had managed to save. When Northeast subsequently became a takeover target, the stock tripled; by the time Ray graduated from high school, he had several thousand dollars invested in the stock market.
Dalio has said he fears boredom and mediocrity far more than he fears failure, and perhaps that’s because he’s rarely failed during his storied career. He founded the world’s largest hedge fund firm, Bridgewater Associates, which manages about $160 billion in assets and has seen almost $50 billion in gains since its inception through 2017, more than any other firm in the category. One of the world’s 100 richest people, Dalio has a personal net worth of nearly $14.6 billion, according to Bloomberg—more than the GDPs of Guyana, Montenegro, and Fiji combined. His 2017 book, Principles: Life & Work, is a New York Times No. 1 best-seller.