Making Mistakes – Josh Steiner (EP.502)
episodePreviously titled “Making Mistakes – Josh Steiner (EP.503)” — renamed by the publisher on Aug 3, 2026
Capital Allocators – Inside the Institutional Investment Industry
1h 1m
1 speaker
4 chapters
transcribed 1 month ago
Transcript
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Transcript generated automatically by AI and may contain errors.
What is the overall focus of the episode and who is the guest?
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 recognition that almost every compelling investment has an approach avoidance capacity. It's that willingness to understand what is compelling about it and what is making us fearful, not in a binary sense.
It's the word and, not but. That's why when we're looking at investment, I don't like risks and attractions. These things aren't diametrically opposed. A more effective tool is to say, what do you have to believe to be true in order to be attracted to this? We are trying to be attracted. To be investors, we have to put money to work. Just thinking about the risk is ineffective.
I'm Ted Sidies, 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 Meaning, 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 at Bloomberg in the 2010s, has served on Yale's investment committee for nearly a decade, and five years ago returned to private equity as co-founder of SSW Partners, managing capital for a few families.
Our conversation focuses on mistakes, quite a contrast from other discussions on the podcast. We kick it off with Josh's big mistake at Treasury and analyze the nature of mistakes and what happened to Josh. We then turned to his mistakes in investing, across deals, managing an investment business, managing people, and serving on investment committees. We close with frameworks to avoid mistakes and with Josh turning the table on me to discuss an impactful mistake I made that I've never discussed before. Before we get going. I recently did something I almost never do. I went to the beach for the afternoon, sat and read. A full Florida beach afternoon, chair, umbrella, sunscreen, the whole production. The beach is awesome, and Florida is really awesome this time of year.
But my time in Florida is more like adult summer camp. Tennis, golf, biking, walking, lots of activities. Sitting for a few hours just isn't part of my routine. Now the flip side is an afternoon reading about investing in the sunshine is, as Will Farrell put it in the movie old school, glorious. It left me wondering why it was the first time I'd done it this year. And that got me thinking, there are people in your life who haven't listened to this podcast for the same reason I haven't sat my butt in a beach chair. They're too busy, too scheduled, and too focused on priorities to sit still for an episode. What they may not realize is over 500 conversations with the best capital allocators in the world are waiting for them while they're on the go, during a commute, a workout, or even a beach chair with nowhere to be.
My guess is you know who that person is. So why not send them an episode of Capital Allocators or a link to our best of playlists on Spotify? Consider it your good deed before Memorial Day officially kicks off beach season. Thanks so much for spreading the word. Capital Allocators is brought to you by AlphaSense. Here's something for you. Most AI tools today are very good at sounding right. But can you actually trace it back to a filing, transcript, or specific passage that drove the answer?
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Chapters
4 chapters
1
What is the overall focus of the episode and who is the guest?
0:00–7:45
2
How did Josh Steiner’s early mistake at the U.S. Treasury shape his view on mistakes?
7:45–34:53
3
What was the high‑profile Whitewater diary mistake and how did Josh handle it?
34:53–53:37
4
How does Josh unpack the psychological “schema” behind his mistake?
53:37–1:01:41