Ray Dalio shares what he’s learned from his succession plan at the world’s largest hedge fund

• Ray Dalio is the founder and co-CIO of Bridgewater Associates, the world’s largest hedge fund, with $150 billion in assets under management.
• In an interview for Business Insider’s podcast, “This Is Success,” Dalio said that the succession plan he began in 2010 taught him to be a better leader.
• There were multiple people who had to be moved in and out of roles, and Dalio had to learn how to step back and prepare a co-CEO successor who was already familiar with the requirements.
• He’s learned that a leader cannot be stretched too thin, and that trying an approach is more effective than over-planning.
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The following is a transcript of the video.

Ray Dalio: A lot of learning comes from having the same mistake over and over again until you learn it.

Richard Feloni: I notice that you had said that in 2016, when you had to move your chosen successor, Greg Jensen, out of a co-CEO role to be just co-CIO, that that was the biggest regret that you had had at Bridgewater.

And what I found interesting about that is that essentially the problem there, and correct me if I’m wrong, was that he had two jobs, running both the management and the investment side of things. But what I found interesting is that a decade prior to that you said that you had found that same problem for yourself in 2008. That you had two full-time jobs and that you couldn’t do both. How did you not see that you were kind of passing on the same thing that you had gone through?

Dalio: First of all, I would say a lot of learning comes from having the same mistake over and over again, and until you learn it. So, in my particular case, you know, the company grew up under me, and there I was, and I was handling too many things, and I was getting by, and I was figuring out how to get those things by, but not adequately. And then I figured, OK, now that's my situation, my dilemma, and I should pass along both my dilemma and my circumstances to him, and we should try to figure out how to deal with that together.

But, in other words, I can't not pass it along, and yet we don't have a solution yet, and so we will try to deal with that together.

And that's the path that we went down, and we found out that we couldn't do that together because it was just too much for him, too much for me.

So I guess I would say, you know, you form a theory, and the theory doesn't work, and then you try again, and you form another theory, and that's part of the learning process.