Making Mistakes – Josh Steiner (EP.502)
Capital Allocators – Inside the Institutional Investment Industry
Ted Seides – Allocator and Asset Management Expert
4.7 • 841 Ratings
🗓️ 18 May 2026
⏱️ 61 minutes
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Summary
Josh Steiner is a polymath of the New York and D.C. 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 U.S. 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 turn 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.
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Transcript
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| 0:00.0 | Most decisions that we make involve both a desire to approach something and a desire to avoid |
| 0:06.8 | that very thing itself. |
| 0:08.0 | We're not anxious about things that we have no desire to do. |
| 0:12.0 | No one feels particularly anxious about falling into a pit full of vipers, because you don't |
| 0:16.6 | really face that as a possibility. |
| 0:18.7 | You might well feel anxious if you're at your child's birthday party |
| 0:22.0 | and they're going off and they're passing pets around and one of which is a giant snake. |
| 0:26.9 | Suddenly you feel anxious about that snake even though you didn't feel anxious about that pit full of |
| 0:32.0 | them. In investing, there's a recognition that almost every compelling investment has an approach |
| 0:37.3 | avoidance capacity. It's that willingness to understand what is compelling about it and what |
| 0:43.2 | is making us fearful, not in a binary sense. It's the word and not but. That's why, |
| 0:48.9 | when we're looking at investment, I don't like risks and attractions. These things aren't |
| 0:53.7 | diametrically opposed. |
| 0:55.5 | A more effective tool is to say, what do you have to believe to be true in order to be |
| 1:00.3 | attracted to this? |
| 1:01.8 | We are trying to be attracted. |
| 1:03.3 | To be investors, we have to put money to work. |
| 1:06.1 | Just thinking about the risk is ineffective. |
| 1:14.1 | I'm Ted Sides, and this is Capital Allocators. |
| 1:20.1 | My guest on today's show is Josh Steiner, a polymath of the New York and D.C. |
| 1:25.7 | Power corridors across government, media, and finance, |
| 1:29.7 | and co-author of From Mistakes to Meaning, Oaning Your Past So It Doesn't Own You. |
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