Ray Dalio was a ‘below average’ student who got into investing by 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 seeks out 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 involved 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 them.

“I took my caddy money, and I put it into the stock market. First stock I bought was the only company I ever heard of that was selling for less than $5 a share. And my logic was I could buy more shares, so if it went up, I’d make more money, which was dumb.”

That company (Dalio has previously said it ...