Ray Dalio Went From Struggling Student to Wall Street Billionaire. Here’s How That Affects His Hiring Philosophy.

Billionaire investor Ray Dalio draws from his own experience with low grades when it comes to hiring new talent. 

In a conversation with Harvey Schwartz, CEO of the Carlyle Group, on the CNN podcast, Dalio described himself as a “below average” student who was happy when he managed a C-minus on tests. High school was a difficult time for him because his “lousy” memory made traditional, test-heavy classes difficult, he added. Dalio, who founded the prominent hedge fund Bridgewater Associates, wasn’t interested in school. He preferred working odd jobs instead. 

“I caddied,” Dalio said on the 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.”

With his caddy earnings, he decided to try investing.

His first pick was the only company he’d heard of trading for under $5 a share. “My logic was I could buy more shares, so if it went up, I’d make more money, which was dumb,” he said. The company was Northeast Airlines, which Dalio said he first bought at age 12. It eventually went bankrupt, but was later acquired, and the stock tripled. “And I got hooked,” Dalio continued.

Dalio previously told the sports media outlet Golf that the course he worked at was The Links Golf Club on Long Island, now defunct, and that among the men he caddied for were Donald Stott of specialist trading firm Wagner, Stott & Co., and George Leib, former chairman of investment bank Blyth & Co. Those early brushes with Wall Street helped shape his interest in markets.

College success and a different view of talent

Dalio did better academically in college, at C.W. Post College at Long Island University, in part because he could choose courses that engaged him. He graduated with a bachelor’s degree in finance in 1971 and went straight to Harvard Business School, where he completed his MBA in 1973. Yet his own overall experience of education informs how he assesses candidates today. He says that having struggled early on gives him a different lens on what makes someone valuable in the workplace.

“I get to hire the best of the best out of whatever schools I want, the best and the brightest,” Dalio said on the CNN podcast. But he’s skeptical that top grades alone predict the qualities he needs. “And what I find quite often is the case is that the student who did really, really well, and in remembering all the things that they’ve learned and so on, hadn’t gone through anything like that, [and] may not be the most inventive, may not be the most determined.”

Dalio emphasized that he’s not just screening for technical skills; he’s looking for people who have confronted barriers and pushed past them. “There’s a lot of talent out there,” he said. “There’s a lot of people who are talented in the circumstances where there are barriers, and they got past their barriers. That’s quite good.”