Ray Dalio says he’s not everyone’s idea of a great boss.  But Dalio, founder of Bridgewater Associates, is starting to look like the Steve Jobs of hedge funds: exacting, infuriating and -- there’s no way to sugarcoat it -- kind of odd.

The singular culture Dalio has fostered inside Bridgewater, the world’s largest hedge fund, was on full display Wednesday, when he announced that the man he’d hired to help run his $160 billion firm, and presumably set the stage for a smooth succession, had abruptly departed. 

That executive, Jon Rubinstein, knew from tough bosses: he’d worked for Jobs for 16 years. One of the creators of the iPod, Rubinstein lasted all of 10 months at Bridgewater. It’s a familiar story at the firm, where Dalio’s quirky workplace culture -- he calls it "radical transparency" -- churns new recruits like few others. Dalio, halfway through a 10-year succession plan, is now replacing Rubinstein with an insider who almost left the firm early this year.

“We mutually agree that he is not a cultural fit for Bridgewater,” Dalio said of Rubinstein in a client note posted on LinkedIn Wednesday.

Unique Culture

Plenty of investment chiefs have struggled to groom a successor. Izzy Englander, George Soros and Seth Klarman have all stumbled as they tried to install the next-generation leader at their firms. But Dalio, 67, is something special. His goal is to find someone to help overturn five years of middling performance and who will embrace and maintain Bridgewater’s unorthodox culture -- where disagreement is encouraged, employees grade each other on interactions, and talking about others behind their backs is deemed a "lack of integrity."

Rubinstein helped to plan a redesign of Bridgewater’s technology and will remain as an adviser to the firm. He ended up more focused on day-to-day tasks rather than big-picture strategy, according to a person with knowledge of the matter. Frustration has mounted among those revamping the firm’s technology because of the difficulty recruiting engineers to Bridgewater’s culture and its Connecticut headquarters, slowing the pace of updating legacy systems, the person said.

Dalio and Rubinstein declined to comment for this story.

Before Rubinstein’s arrival in May, a longtime insider and co-investment head, Greg Jensen, held the role of co-CEO. But Jensen gave up that title after disagreeing with Dalio over whether the founder was sticking with his hedge fund succession plan.

Another Pick

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