Making Mistakes – Josh Steiner (EP.502)

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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