Ray Dalio's Former Personal Assistant Said Her Employment Was Like 'The Devil Wears Prada'

ray dalio

We’re all familiar with the mystique and cult-like atmosphere that surrounds Ray Dalio’s Bridgewater. rumours are rampant and imaginations tend to run wild when it comes to discussing what it’s really like to work in the Westport, Connecticut-based hedge fund. 

Well, imagine no more. DealBook’s Kevin Roose happened upon a blog post that Kathleen O’Grady, a former personal assistant of Dalio’s, wrote about her experiences working for the king of hedge funds.

O’Grady is now an “authenticity coach” based in North Carolina, and she told Roose that working at Bridgewater was much like the story of the book/film “The Devil Wears Prada,” in which a college graduate works for a high powered fashion magazine editor.

Now, before you start drawing comparisons of Ray Dalio to Miranda Priestly (or Meryl Streep, for that matter), O’Grady said it was the erratic and surprising nature of many of her tasks that fuelled the metaphor. She also looked upon the experience fondly and wrote that she learned more in six months at Bridgewater than most people do in a lifetime.

Here’s the story behind one of those strange tasks that she was charged with:

As I remember it, one of Ray’s clients from Japan had visited his home in Vermont and the two of them went hunting. The client shot a very large and unique looking bird. In what I imagine was a gesture of respect for the man and the bird, Ray had the thing stuffed by taxidermy and mounted on an engraved plaque. It was my job to get it shipped to Japan. I’ll never forget. It was a particularly windy day in Westport, CT and I delicately placed the mounted bird in my passenger seat, gingerly wrapping the seat-belt around its midsection without mussing the feathers. Carrying the bird in and out of the post office and several shipping stores became more hilarious each time. People stared. I smiled back. Finally though, when I’d reached the last place in the area that I could try before getting back to the office on time, I wasn’t going to take ‘no’ for an answer. The clerk gave me a look of disbelief when I placed the bird on the counter and I said, “I need to ship this to Japan.” He just laughed at me. I then looked at him sternly and said, “This is no laughing matter. This bird needs to make it to Japan in flawless condition or I will lose my job.” The guy looked back at the bird and then back at me. By then I had used my acting skills and summoned some tears. Finally he agreed to try and crate the bird for shipment. I still don’t know to this day if it made it past customs, but I was satisfied that I had not given up on my task.

Read more about O’Grady’s stories here >

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