Making Mistakes – Josh Steiner (EP.503)
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Most decisions that we make involve both a desire to approach something and a desire to avoid that very thing itself. We're not anxious about things that we have no desire to do. No one feels particularly anxious about falling into a pit full of vipers because you don't really face that as a possibility. You might well feel anxious if you're at your child's birthday party and they're going off and they're passing pets around and one of which is a giant snake. Suddenly you feel anxious about that snake even though you didn't feel anxious about that pit full of them. In investing there's a recog
I'm Ted Seides, and this is Capital Allocators. My guest on today's show is Josh Steiner, a polymath of the New York and DC power corridors across government, media, and finance, and co author of From Mistakes to Owning Your Past So It Doesn't Own You. Josh rose to national prominence as the youngest ever chief of staff at the US Treasury in the Clinton administration, where he made a high profile mistake he unpacks in the book. He pivoted to finance as a media investment banker and co founder of private equity firm Quadrangle Group in 2000, worked as an operator of Bloomberg in the twenty ten
My pleasure. Thanks for inviting me.
So we're gonna talk a bunch about mistakes, And I thought maybe the best way to dive in might be the initial mistake that led to you writing this book with Michael in your early days of treasury. First of all, I love the idea that you have
all these incredible investors on your podcast and you talk to them about their marvelous accomplishments. And with me, it's only gonna be mistakes. In 1993, I went down to Washington to work on the Clinton transition. I had the good fortune of ultimately going to Treasury first to work for Roger Altman, was Deputy Secretary to be a Special Assistant. Surely thereafter, six or eight months into the term to become Chief of Staff for Lloyd Benson. Lloyd Benson was one of the icons of that great generation. The guy had been a World War II bomber pilot, a member of Congress, a CEO, a Senator, a pr
my career. When did you start trying to understand what drove the decisions you made in that moment?
Not until years later. I grew up in New England where the key phrase is repress for success. I went off to boarding school at the age of 14. If you do that at an early age, you view emotions as something that get in the way of coping. The way you cope is by playing sports and studying harder and pretending that no one has the capacity to hurt you or upset you. I carry that forward after white water and after my diary got exposed to the world. I used that same technique. Literally for years later if anyone ever wanted to talk to me about white water I would make a joke or I would brush it off.
How do you distinguish between a mistake and a failure?
When you read news story, those words are almost always used interchangeably. In the first paragraph, it will say, Dad, you made a terrible mistake. And then in two paragraphs, I will say, Well, failure you made was this. Amusingly, when we've gone off and given talks about this book, often the title of the talk will be Steiner and Linton to talk about failures. I'm like, No, no, no. We're not talking about failures, we're talking about mistakes. We had to really figure out our difference and our definition is as follows: We think of failures and success as siblings. In both a failure and a su
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