YouSaid · the spoken record

Josh Steiner

lines on the record: 72
first: 2026-05-18
most recent: 2026-05-18
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“has nothing to do about the toaster and everything to do with family dynamics because I had spent so much of my life trying to repress the emotional side of what I did, my belief in hyper rationality. I didn't appreciate that a lot of investing does need to reflect underlying emotions. It needs to reflect the personalities and characters of the CEOs that you're backing. It needs to reflect the fact that consumers aren't entirely rational actors either. The way they're going to interact with your products may not be based exclusively on a set of rational decision making. A recognition that your colleagues and partners have their own motivations and ways of thinking about the world in order to create an effective environment where you can make excellent investment judgments.”
2026-05-18 · Capital Allocators · Making Mistakes – Josh Steiner (EP.502) · IDENTIFIED FROM THE TRANSCRIPT · source
“Wife was awesome in many respects. She's a nonprofit litigator for many years and then became a nonprofit mediator. One of the things that she did is she got trained as a mediator was understanding how to listen to people more effectively and have more open communication. Recognition that people's emotions and their schemas come into what seemingly are straightforward decision making. The expression that she uses, it's never about the toaster. She works with low-income couples who are trying to separate or get divorced. They will have agreed on everything. They will agreed on child support and on custody. Suddenly they're having a fight about a toaster. Turns out that the husband's aunt had given them that toaster, the wife felt that that aunt was always disrespectful to her. She wants the toaster as a way of proving to her husband that that aunt was vicious and the husband wants the toaster.”
2026-05-18 · Capital Allocators · Making Mistakes – Josh Steiner (EP.502) · IDENTIFIED FROM THE TRANSCRIPT · source
“And then Acts three is how do you deal with it? Do you go off and offer apologies to people you've hurt? Do you forgive yourself? Do you process your mistake? When I thought about my mistake, I was super focused on Act two. Why had it been so stupid to keep that diary? I didn't think about what had happened in Act I, either the fact that I had kept a diary in a different context and it had been fun, and I certainly didn't think about this whole idea of repress for success. The result of that is I made a whole new mistake in Act III, not dealing with it, not talking about it, keeping it inside me long after everyone else had forgotten about it.”
2026-05-18 · Capital Allocators · Making Mistakes – Josh Steiner (EP.502) · IDENTIFIED FROM THE TRANSCRIPT · source
“Used executive by word, which is unpacked. We think of these things as like Russian nesting dolls. You have to keep lifting it up and lifting it up. For both Michael and me when we started talking about it, we were nowhere close to the real mistake until we've gone through it several times. We wrote draft after draft of our own mistake, pushed each other, and said, wait a minute, there's something else I think is going on here. Was it just your poor decision-making process? Or was it just the fact that you were testifying before Congress and you were a young person? didn't have a framework for thinking about mistakes. And one of the things we figured out was that each mistake is a free act play. There's act one, and that's where your schema is generally developed, either in your childhood or in your early professional experience, you form a way of looking at the world. Act two is when you make the mistake itself. You make a decision, probably without self-awareness about your emotional state or your context.”
2026-05-18 · Capital Allocators · Making Mistakes – Josh Steiner (EP.502) · IDENTIFIED FROM THE TRANSCRIPT · source
“They're creepy. Schemas help us process the world without having to reconsider at each time. There's a lot of research behind this. These mental templates are incredibly helpful. Going back to my mistake, my mental template was repressed for success. There's no question it served me well. It allowed me to process going through high school, playing sports, going to college, going into the investing world, and having relatively difficult jobs. What it didn't help me do was process this hard event, this bad mistake that I had made. When your schema works, it's an incredibly powerful shortcut. When you misapply it to a situation, it can lead to a whole new form of mistake. That's what happened in my case. All the people we interviewed, Malcolm Gladwell, Irv Gotti, Michael Gubbin, Joanna Coles, they all told us about mistakes, and almost each instance it revealed some schema that they had been carrying around.”
2026-05-18 · Capital Allocators · Making Mistakes – Josh Steiner (EP.502) · IDENTIFIED FROM THE TRANSCRIPT · source
“More we made those lists, the harder it was to categorize them. And the lists just got longer and longer and longer. We realized that we needed a different kind of help. We didn't need ethical help, which is a religious help, which is how we generally thought about mistakes. What we needed was psychological help. We ended up partnering with this fantastic professor from John Hopkins, woman, Namison Papadakis, who helped us think about it. Working with her, the common thread throughout was this idea of a schema. Schemas are mental templates, which now is to process. They're as simple as the following. You walk into an elevator and if you're by yourself, you sand wherever you want. If they're true people, you stand on opposite sides. If there are four, you go into the corners. Imagine you didn't have that schema in your mind about where you're supposed to stand in an elevator, or worse still, the person who came in with you didn't have it. They stood right next to you and the elevator. It would be deeply uncomfortable.”
2026-05-18 · Capital Allocators · Making Mistakes – Josh Steiner (EP.502) · IDENTIFIED FROM THE TRANSCRIPT · source
“When we started this process, we started making lists of mistakes. We thought we were going to organize this book around types of mistakes. And you mine immediately begins rushing through all of them. Those of you who can't see a Ted smiling even I'm sure he's thinking about all the types of mistakes that he's made. In fact, we should probably talk about that now that I think about it. And we're going to get there now that I can say we're not going to let you off the hook. But your mind immediately goes, and the easiest way to think about it are the seven deadly sins. Greed, lust. There are all these different motivations that lead people to make mistakes.”
2026-05-18 · Capital Allocators · Making Mistakes – Josh Steiner (EP.502) · IDENTIFIED FROM THE TRANSCRIPT · source
“The mistake itself, and then what drove us to make it. We also think that mistakes generally reveal an aspect of our personalities that we may not like. The effort to explore the mistake can be very painful for people because that exploration may help you discover something that you don't find super attractive and that you don't really want to reveal to yourself, let alone to someone else.”
2026-05-18 · Capital Allocators · Making Mistakes – Josh Steiner (EP.502) · IDENTIFIED FROM THE TRANSCRIPT · source
“That's very different from a failure, which involves careful planning and cooperation. Failure almost always leads to lessons, which people take away from them. Success always leads to a sense of accomplishment. Mistakes, we generally shove under the rug and hope people never see it we never want to discuss. Why do you think that is? Because of the embarrassment and shame. Society, especially here in the United States, is awesome about failure. We really admire entrepreneurs who pick themselves off of the ground. You and I both know investors who were unsuccessful in their first fund, dissolved it, went to work from somewhere else, came back and did it a second time, and had been successful. We admire the persistence and their willingness to plan more carefully the second time and to go off and try to achieve that big addition. In the case of mistakes, the embarrassment leads us to want to hide.”
2026-05-18 · Capital Allocators · Making Mistakes – Josh Steiner (EP.502) · IDENTIFIED FROM THE TRANSCRIPT · source
“Work out, that's a failure. In the other case, it does, it's a success. A mistake is very different. A mistake is a decision that you make almost always by yourself where you're not aware of your surroundings or your emotional state, then it leads to regret. There's no planning.”
2026-05-18 · Capital Allocators · Making Mistakes – Josh Steiner (EP.502) · IDENTIFIED FROM THE TRANSCRIPT · source
“and a failure. You read a new story, those words are almost always used interchangeably. And the first paragraph will say, Dad, you made a terrible mistake. And then the two paragraphs that will say, well, the failure you made was this. Amusingly, when we'd gone off and given talks about this book, often the title at the talk will be Steiner Linton to talk about failures. I'm like, no, 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 success, people come together. They have an ambition. They make a plan. They're trying to achieve something worthwhile. That's why we say it's a successful marriage, but we also say marriages fail. Both cases, people come together. Their plan is to lead a healthy and happy lives together till death do them part. But in one case, a death...”
2026-05-18 · Capital Allocators · Making Mistakes – Josh Steiner (EP.502) · IDENTIFIED FROM THE TRANSCRIPT · source
“Ourselves from exploring them, stop giving them an agency over our past. Our expectation was that we would find a really good book about mistakes. When you go into a bookstore, you go on Amazon, there's so many great books about success. There are books about entrepreneurial success, scientific success, government success. There are also good books about failure. Shackleton goes to Antarctica and doesn't succeed. Apollo 13, there wasn't the book about the kinds of mistakes that we all make in our daily life that lead to embarrassment and shame. So we set out to write the book, initially just to try to explore our own mistakes, we ended up interviewing a lot of other people about theirs.”
2026-05-18 · Capital Allocators · Making Mistakes – Josh Steiner (EP.502) · IDENTIFIED FROM THE TRANSCRIPT · source
“Period of contemplation was seeing the impact of this public health crisis on people's lives? Could it happen to me? Should I be looking backwards and trying to resolve some things I'd left unresolved? Also, what can I learn from the past and ensure hopefully that the years to come are spent in a healthier, both mental and physical way? I realized that I had made this really bad mistake. I had gone through this quite embarrassing episode in my life. I had never confronted it. I'd never really tried to unpack what happened. I went to my friend Michael Litton, the co-author of this book, and I said to him, Michael, you made a really bad mistake, which you'll never talk about. And whenever I try to raise it with you, you blow me off. It annoys me when you blow me off. It took me a minute to realize that the reason that annoyed me so much is he was manifesting the exact same behavior that I was. I said to him, we really should try to understand why we made these mistakes and stop preventing.”
2026-05-18 · Capital Allocators · Making Mistakes – Josh Steiner (EP.502) · IDENTIFIED FROM THE TRANSCRIPT · source
“Not until years later I drew 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 carried that forward after Whitewater and after my diary got exposed to the world. I use that same technique. Literate 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. I just wouldn't explore it. I wasn't willing to talk about it. I really didn't even think about it. In fact, if the word diary came up in an article, I quickly moved past that article for fear that they would mention my diary as the exemplar of what you should not do. Fast forward 2020, COVID hits. All of us, I think, are going through a”
2026-05-18 · Capital Allocators · Making Mistakes – Josh Steiner (EP.502) · IDENTIFIED FROM THE TRANSCRIPT · source
“To provide a verbatim account of what happened. You're trying to write impressionistically. And in my case, I had kept a diary when I had traveled through Asia years before and begun the practice. And it was very impressionistic. Now I was in a pickle. I had a senator reading something from my diary, something I myself had written, to be clear. What I had written didn't completely comport with what I remembered because it wasn't an attempt to write a verbatim account. So I had a choice. I could either say, yes, Senator, dude, that's exactly correct. Or I could correct what I had written myself. Neither of those options were particularly good. I felt it important to try to tell the truth. I needed to correct what I invented myself, which understandably gave people the impression that I had either lied to my diary or I was lying to them then. It was front page news, it was deeply embarrassing. I offered then Secretary Benson my resignation. He kindly didn't accept it.”
2026-05-18 · Capital Allocators · Making Mistakes – Josh Steiner (EP.502) · IDENTIFIED FROM THE TRANSCRIPT · source
“Long pause. My heart sinks. I think to myself, well, I keep a personal diary. I wondered whether I had actually vinted anything about Whitewater in that personal diary. And there's a passing reference to any personal letters as well. I go on that night and I get out my diary and I realize that alas, yes, I had written about Whitewater in my personal diary, so I have to turn that over. I had also written letters to my then girlfriend, now wife, in which I had referenced the whitewater matter. Those things get turned over to the investigators. I ultimately have to testify in Congress before the House and the Senate and the grand jury in both the House of the Senate. They read out portions of my diary about Whitewater, then they ask me whether they were accurate. For anyone who has ever kept a journal or a diary or written a letter to a girlfriend, you're not trying.”
2026-05-18 · Capital Allocators · Making Mistakes – Josh Steiner (EP.502) · IDENTIFIED FROM THE TRANSCRIPT · source
“In addition to being a real estate transaction, it also involved a bank, which became insolvent, got taken over by the RTC, the Resolution Trust Corporation, which was part of Treasury. Roger, who was the deputy secretary, also became acting head of the RTC. It was a question about whether he was going to stay involved in that investigation. An independent counsel got appointed when that happened. All of us at Treasury got subpoenaed for all of our records. When you get subpoenaed, you get a piece of paper from the Justice Department and it said you have to turn over all of your official documents. That seemed pretty straightforward. You also have to turn over any personal papers that might in any way relate to the Whitewater investigation.”
2026-05-18 · Capital Allocators · Making Mistakes – Josh Steiner (EP.502) · IDENTIFIED FROM THE TRANSCRIPT · source
“Had the good fortune of ultimately going to treasury first to work for Roger Aldman, who was deputy secretary, to be a special assistant. Shortly 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 presidential candidate. Then he became Secretary of Treasury for Bill Clinton. At the age of 27, I became chief of staff to 72-year-old Lloyd Benson, a man of just impeccable case, dignity, character. What's also mostly happily forgotten was the first term of President Clinton was marred by a series of scandals, the most notable of which was Whitewater. Whitewater was this little unimportant real estate transaction in Arkansas that ultimately led to the present”
2026-05-18 · Capital Allocators · Making Mistakes – Josh Steiner (EP.502) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 going to be mistakes.”
2026-05-18 · Capital Allocators · Making Mistakes – Josh Steiner (EP.502) · IDENTIFIED FROM THE TRANSCRIPT · source
“I'm Ted Sidees, and this is Capital Allocators. I guess 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.”
2026-05-18 · Capital Allocators · Making Mistakes – Josh Steiner (EP.502) · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2026-05-18 · Capital Allocators · Making Mistakes – Josh Steiner (EP.502) · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2026-05-18 · Capital Allocators · Making Mistakes – Josh Steiner (EP.502) · IDENTIFIED FROM THE TRANSCRIPT · source