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Ray Dalio was a ‘terrible student’ who got into investing by golf caddying for Wall Street traders: Now he hires talent who have experienced hardship

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29.06.2026

Ray Dalio was a ‘terrible student’ who got into investing by golf caddying for Wall Street traders: Now he hires talent who have experienced hardship

Ray Dalio was a self-professed “below average” student, bringing home grades of C-minus on a good day. However, the billionaire investor is now a household name, and says when he is looking to hire talent, he looks for people who have had to overcome obstacles to get opportunities. In a conversation with Harvey Schwartz, CEO of the Carlyle Group, the Bridgewater Associates founder outlined how his early years were no indication of the success he later attained. High school was a struggle, he said, because he had a “lousy” memory, and classes were teachers merely testing that memory.In addition, Dalio said he simply wasn’t interested in much of the content, and instead kept himself busy by working odd jobs.

“I caddied,” Dalio said on the CNN podcast. “And when I would walk around the golf course caddying for people, the stock market was hot at the time. So I would talk about stocks with........

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