#96 - The Discipline of Giving: Wealth, Greed, and Responsibility (David Roberts, Retired Partner at Angelo Gordon)
Investing In Integrity · 2026-02-20 · 1h 10m
Substance score
37 / 100
Five dimensions, 20 points each
What our scoring noted
Our reviewer’s read on each dimension, with quotes from the episode.
Insight Density
The episode is heavily padded with mutual appreciation, lengthy host monologues, and philosophical platitudes about generosity and capitalism. Actionable or novel insight density is low, with the most substantive moments—Keynes on post-scarcity, relative vs. absolute scarcity, and the immigration bond mechanism—buried in conversational filler.
if you have unfettered capitalism, it's very dangerous because we can get into the gutter literally in terms of gaming the system
I'm skeptical about post scarcity world because there's always a top 10% and a bottom 10%, right? That's fixed mathematically, logically
Originality
The ideas presented—capitalism needs guardrails, greed is a threat to the soul, generosity makes you happier, compassion is the better fuel—are widely circulated and unremarkably framed. The Keynes post-scarcity angle and the AI-generated fake immigration court hearings are the only genuinely fresh elements.
a fraudster created a fake hearing in front of a judge with AI characters just to prolong the fraud
Avarice is something to watch out for, particularly if you're in the finance industry, which is all about making money. It's a threat to your soul
Guest Caliber
David Roberts is a genuine practitioner who helped build a major alternative asset manager from 15 people to hundreds, which gives him real credibility. However, in this episode he is functioning almost entirely as a wealthy philanthropist and Substack essayist rather than as a finance operator, so his depth of relevant expertise is underutilized.
the firm when I joined was 15 people and I think like $300 million of assets under management
I was lucky to get in, really on the ground floor and help the company grow by starting a number of its businesses, including real estate and some of the structured credit businesses
Specificity & Evidence
There are isolated moments of concrete detail—the $10,000 immigration bond, the 95% bond recovery rate, AUM figures—but the vast majority of the conversation operates at a high level of abstraction, referencing named books and thinkers without drilling into their actual arguments or data.
the bonds are like $10,000, which most of the people can't afford. And this is an organization that puts up the bond for these people
95% of the time, the money comes back
Conversational Craft
The host explicitly cedes control of the format to the guest's preference for 'a conversation,' resulting in extended host monologues, frequent self-referential asides, and zero substantive pushback on any claim. The guest ends up asking the host a question, inverting the dynamic entirely and revealing the absence of structured inquiry.
Sorry, I've been verbose.
David wanted this to be a conversation so I share a lot more of my thinking
Conversation analysis
Computed from the transcript - who did the talking, and the verbal tics along the way.
Filler words
Episode notes
David Roberts spent nearly four decades in finance—starting on Wall Street in 1983 and joining Angelo Gordon in 1993, when the firm was a 15-person shop managing about $300M. By the time he left, the firm managed roughly $50B in assets, and David contributed to that growth by helping build and launch several of the firm’s businesses. After retiring, he created Sparks From Culture , a widely read Substack, which provides its nearly 9,000 readers with “weekly personal essays on wealth, status, and family from someone with generational wealth, writing with transparency.” Our host, Ross Overline , is one of David’s readers. In this conversation, David and Ross explore the hardest questions finance leaders rarely discuss publicly: How do you know when you have “enough”? Why does comparison keep resetting our definition of success? What are the risks of wealth concentration? They discuss inequality, philanthropy, competing views of capitalism’s current state, and how greed often shows up as self-justification. David makes the case for generosity as a stabilizing force in society—and shares how he’s translated these beliefs into real, high-impact giving.
Full transcript
1h 10mTranscribed and scored by The B2B Podcast Index.
Foreign. Welcome to Investing in Integrity. I'm Ross Overlein, CEO and co Founder of Scholars of Finance, a rapidly growing organization on a mission to inspire character and integrity in the finance leaders of tomorrow. If you're an investor, finance professional, or student aspiring to make an impact with capital, this show is for you. Investing in Integrity brings you conversations with leading minds in finance to help you learn how you can make finance a force for good by investing in integrity. On today's episode we had a really interesting conversation with David Roberts. David Roberts was a partner, Angelo Gordon. He joined the firm when it was a 15 person shop managing about $300 million of assets and when he left they were managing almost 50 billion in assets. And over his nearly 40 year career in finance, he thought a lot about wealth and responsibility. He retired from Angela Gordon several years ago and he created a substack called Sparks from Culture and over a few years of shifting sharing his thoughts once a week, he's amassed subscribers who receive his writing each week via email. And I'm one of them and very grateful to be David is a compelling voice for all of us on really important subjects like wealth, privilege, generosity, influence. He takes big topics head on, a lot of things that a lot of people don't feel comfortable talking about publicly or don't share their thoughts about publicly. David does, and I think there's a reason that he's gained such a following in his writing. I know I have found his writing extremely thought provoking and I'd highly recommend you subscribe. In today's conversation we explore generosity, equality, the importance of giving back. We talked about philanthropy, we talked a lot about capitalism and different views on capitalism's current state, on capitalism's future, how we can create an economic system in society where more people are thriving and flourishing. And I think you're going to find it really, really interesting. This was a bit different than most of our episodes in that David said he wanted this to be a conversation. Normally I'm asking questions, sharing some cursory thoughts with our guests, but mostly asking them to share their perspective and David wanted this to be a conversation so I share a lot more of my thinking. He also posed some questions to me at the end. I really enjoyed the conversation. I hope that you do as well. David Roberts is an incredibly thoughtful leader and he's a supporter of Scholars of Finance, a donor. We're grateful to him and Debbie for their support of our mission. And when you listen to this conversation, you'll get a sense of why David supports our work and is a leader in this community and why we were so grateful to have this conversation. So without further delay, he here is David Roberts. David Roberts, it is such a pleasure and an honor to have you on the Investing in Integrity podcast. We've got a lot of ground to cover today, but first, how are you doing and where are you calling in from today? I'm in New York City, which is very cold and there's still a lot of snow piled up, which is turning gradually into slush. But I am safe and warm inside and appreciative of that. I'm glad that you're safe and warm at the time of this recording. The giant storm that hit the Eastern seaboard just hit a couple days ago, and it's fresh. I'm glad you're doing well, David. I've been really looking forward to having you on just for a conversation. This is gonna be a bit of a unique episode of the Investing in Integrity podcast. As you know, oftentimes I'm asking questions and putting my journalism degree to work. And today I was really honored that you wanted to have a conversation about generosity, about inequality, about giving back, about our responsibility as people with social capital, career capital capital. And I want to begin just by asking you to share for our community just a bit about your background and your story. Sure. I grew up on the Upper east side of Manhattan and went to a couple of different private schools here and then went to University of Pennsylvania and then started on a career on Wall street in 1983 and really have worked for about almost 40 years, first as an investment banker and then on the buy side. And most of that the buy side was beginning in 1993 for a company called Angelo Gordon, which has since been acquired by tpg. And there I was lucky to get in, really on the ground floor and help the company grow by starting a number of its businesses, including real estate and some of the structured credit businesses. So, you know, had a long and good career. On a parallel path, I, at a shockingly young age, I met my wife to be in 1984. We got married a year later. We were 23 and 22. We're kind of stunned in hindsight that none of our parents questioned this kind of very reckless decision. But we've been married for 40 years. We have three adult children, all millennials, 32, 35 and 38, and really five adult children because we have a son in law and a daughter in law as well, three grandchildren. We all live in New York City. In 2022, I retired from my finance career and have been devoting myself to, well, to family and to writing. I write a weekly substack newsletter called David Roberts Sparks from Culture. And I write a lot about wealth and status from the perspective of somebody who was born into wealth. My family's had a couple of generations of wealth before me, and I think it is a somewhat unusual point of view to take to write about wealth from a wealthy person's point of view because most people, most wealthy people don't want to write about money for fear of being categorized as either showing off or smug or obnoxious. And so I try to write about wealth when I do with the objective of not coming off as smug or offensive in any way. And then both my wife and I spend a lot of time on some grassroots philanthropic efforts as well. And I know we're going to talk a bit about philanthropy and known by different names, whether you call it charity or justice. And I'm certainly very interested in that topic as well. David, just a level set for our listeners. Can you just share just high level. When you had left Angelo Gordon, sort of the size of the firm and kind of, you know, team assets because you had helped build a pretty substantial enterprise at the firm. Yeah, I mean, the firm when I joined was 15 people and I think like $300 million of assets under management and the office was small enough that John Angelo, one of the founders, could yell my name and I could hear it and say and be summoned across the firm floor. Hopefully that wasn't too often. And when it happened, hopefully it was for good reason. It wasn't always pressing. But anyone listening who knows, John knows that he was a big personality. But anyway, when I left, I believe the firm was 4 or 500 people and managing somewhere 35, 40 billion. I think it depends on how you count it. And I certainly helped with that growth by starting some businesses and hiring some people to really make them substantial parts of the firm. But the founders were terrific and the people that we all brought on to carry the firm forward have done a great job. And as someone retired, I continue to have links to the firm that I value greatly. First and foremost, appreciate your modesty and recounting your own role in the firm's growth. I think it's really helpful for our listeners to understand you helped grow a firm from 300 billion in assets to 40 to 50 billion in assets. A substantial rise, really significant outcomes. And then you retired, as you said, and started writing Sparks from Culture. I've really enjoyed reading your newsletter every week. When I get the email notification Frequently I just find myself 15 minutes later, like, just sucked right in to the material. I'm really curious to hear what prompted that writing you to write about these subjects. What made the topics and questions of wealth of generosity? What made them feel unavoidable? Well, when I first started writing, I did it in a very sort of unstructured, I would say, undisciplined manner. I would read something in the news and want to opine upon it and send it to family and very close friends to whom I gave no choice about becoming subscribers. I subscribed them so, you know, to the 40 people or 30 people or whatever. And then when I noticed the more I wrote personally, the more interested people were, and I began to just grow my subscriber base. And then I also started dipping my toe into writing a little bit about wealth and charity and generosity and so forth. And the response was really good. And I realized there weren't too many other people writing about it the way I was writing about it. And so that really encouraged me to continue. And then I set upon this sort of weekly pace of, you know, writing an essay, coming up with an essay, and it seemed to fit in nicely with everything else that I did and satisfy my intellectual curiosity. I have always been interested in history and literature. In fact, very early in my career, I considered becoming a history professor and actually went back to school for a semester to study history. But I had been in the work world for four or five years, and I had a very naive view of academia, that everyone was there for the love of learning and there'd be no politics in academia. That's actually when I went back to the financial industry. I only lasted a semester. But I've always had this tug between what I would say is the life of the mind and the life of commerce. And at different times of my life, one has seemed more appealing than the other. And really, I would say, even before I left in 2022, I was, I think, yearning more for something that would be more intellectually satisfying. So it felt like the right time in 2022. I'm glad you made the shift. It's been a real source of insight for me, and I can imagine why it's had the response it's had. It's just incredible. And when you and I first met several years ago, from our conversations, you just seem to view it as this new kind of hobby. You mentioned doing it in an undisciplined way, just sharing your thoughts, you know, from time to time, and trying to have a nice cadence of kind of sitting down, reading, thinking, putting thoughts on paper? Did you expect it to become what it's become to have such a large following and so much engagement from your follower base? Did that come as a surprise? Was that a goal? Or did that just sort of happen naturally and organically? I really didn't have any particular expectations about subscriber numbers. And like anyone who is candid, certainly I like getting more subscribers. It's another metric, right? It's different than a financial metric, but writers want to be read, so the more people reading me from my point of view, the better. What was unexpected to me was there's a real community of writers on substack, and I've forged a lot of relationships with other writers, and that's been really rewarding because different points of view, different ages. I have to say, almost all younger than I am. But I've also met a number of people who are, you know, writing about financial topics as well. And we, you know, we compare notes and share information. So, yeah, it's a real community. And. And that's. That's been rewarding. It's. It's awesome. And I appreciate the conflict, the tension between life of mind and life of commerce, as you put it. I wrestle with that personally very acutely. I'm an ambivert between the introvert and extrovert scale. And my wife often jokes, you know, if Ross needs to be alone, but if he's alone for too long, he starts to suffocate. He needs to be with people, but if he's with people for too long, he starts to suffocate. I keep moving back and forth, and when I'm, you know, not out teaching our students, you know, meeting with our donors like yourself, leading the team, I'm listening to audiobooks. I'm. I'm reading essays. I'm studying. I'm just thinking and writing myself. And you've been a bit of an inspiration for me recently. I've just, in the last few months, have started sharing some of my thoughts. And I caveat to anyone listening or who has listened to these with the fact that I'm still in my early 30s. I still have a lot to learn and always will. So none of my opinions are forged in iron, right? They're all evolving and developing, and I'm seeking to learn as I go. One topic that's really been on my mind and on my heart lately has been generosity. You and I talked about this last week when we were catching up, preparing for this. I did my sort of annual Just update on scholars of finance to our donor community, our students, our alumni, our supporters. And after the update on 2025 and our thoughts for 2026, just shared some initial thoughts on generosity and really the like social imperative of generosity. I would say the moral imperative and urgency of generosity. I talked about how when you look at growing inequality, growing division, growing polarization, an openly socialist mayor in New York, I put forth, you know, very directly that capitalism's the best system for maximizing human flourishing and prosperity for all that's ever been tested at any scale, any real scale, that any large experiments with socialism or communism have resulted in degradation of human rights, near halting of social and progress and innovation, sort of everyone being equally oppressed. Right. And my stance that has been evolving is that generosity is a necessary moral counterweight to that risk. Adam Smith said some of the risks of this system of capitalism are wealth concentration, growing inequality between capital and labor, and the neglect of the poor. Right. Capital neglecting labor and what that would do to society. And in his writings, he very clearly puts forth that there is this responsibility that those with power and wealth and resource and capital have to take care of the poor and the neglected and to not leave them behind. My view is that generosity, if broad, based among those of us with resources and influence, is operationalized in meaningful, substantial ways, in clear, visible ways, in selfless ways and ineffective ways that could hold Western society together over the next several decades without it seeming too bombastic. Right. I'm really curious to hear your thoughts at a high level on that, and I want to really dig into your views on generosity. I've read so many of your essays on the subject, and I have so many questions, but love to hear your reactions to that. I know you gave that a listen, and I'd love to hear your thoughts that you're mulling over with regards to generosity and our sort of responsibility to give back. I agree with you on capitalism as the best of all systems that has been tested. But I also feel that guardrails are very much necessary. And I think about. I don't know if you've ever been to a little kid's bowling party. When I was a little kid, yes. Okay. I don't know if you remember, but when they were little kids bowling, it's rare for them to bowl straight, so they have the, you know, these bumpers that come up on the sides so that they protect the ball from falling into the alleyway. And that's what I feel is necessary. Well, politically. But we'll talk economically. Economically, I think if you have unfettered capitalism, it's very dangerous because we can get into the gutter literally in terms of behavior and in terms of gaming the system. Not only do we need people to seek to be loved for their generosity, and that's an Adam Smith phrase from the theory of moral sentiments. People want to be lovable for the right reasons, but we also really need rules to be followed and obeyed and when rules are broken, for those transgressors to be called out. So I think it's a combination of what is valued in a society, society. And I think your organization is trying to show that being generous and being ethical over the long term pays off in every way and generosity is part of that. But yeah, I think societally, if we have something right now that people have called hyper capitalism or late stage capitalism or whatever you want to call it, things can really break and get really bad. Too much inequality and enough of that inequality comes about because people have gamed the system and people feel that the system isn't there at all. That's a real problem. I think we're approaching that and I think that is very dangerous. And one of the ways that you can do something about it, if you have the means, is to be generous and is to give back and to try to be for whoever you interact with, a role model for those values that will perpetuate the system. Sometimes it can feel very dispiriting because you're just one person or one family doing what you can and you can see impacts on individual people or maybe dozens of people. But then you realize how big the population is and the issues are. But you just, you have to keep going and it's, it's really important. I completely agree with you on this need for guardrails. In our last conversation I was talking about how greed is like the ult, one of the ultimate risks in capitalism. Right. If you summarize Adam Smith views on the risks, it's those who have the most become greedy and stop taking care of those who have the least. And those who have the least can only tolerate that for so long. You have written, I think, extremely eloquently about the difference between absolute scarcity and relative scarcity in your post just last December, just recently, imagine there's no scarcity. And I appreciated the music video you appended to that. That was very artfully done. You talk about this John Maynard Keynes prediction that over a century absolute scarcity might be eliminated. We have made significant progress. We've taken billions of people out of absolute Poverty and scarcity over the last century, and books like Progress by Johann Norberg, Factfulness by Hans Orlig. You know, these statisticians who piece together all the drivers of human flourishing and suffering over the last 2000 years. It shows this very compelling picture that in the last 250 years, we've made enormous progress, rapid progress, in lifting people out of poverty and meeting people's basic needs. You also talk about relative scarcity. We teach our students the theory of relative deprivation, the academic framework around this notion of relative scarcity. And you. You write, I think, in very interesting ways, about how when you read Uneasy street, wrote about this in 2024, how those who have wealth have all these mechanisms for sort of putting themselves in this loosely defined middle of the pack by creating this select group of wealthier people who they can compare themselves to and be like, oh, I'm not that wealthy. You know, I. We fly first class, but they have a private plane. I fly nut jets, but he owns his plane. I just. I think it's really interesting, your take on the nature of greed, on awareness of when we have enough, and combating that part of our human nature that makes us compare ourselves to others and want more insatiably once we're well past the point of having enough. Can you unpack that a little bit and share some of your learning and some of your studies on that and some of your own reflections on combating greed and keeping it in check? I think, first of all, it's really. Combating is the right word. The natural inclination is to want more, is to compare yourself to people usually above you in whatever metric you're using. It's beating yourself up for not doing better. I definitely had that feeling about myself. An absolute basis, had nothing that I should have been complaining about. Should is a tricky word, but I ought to have felt better about my own career. But I would always compare myself to people who went off and started their own funds, for example, right. So here I was, I was working for two founders. They were terrific. I was in a great place. I was prospering along with the firm. I was contributing to the prosperity. But then I would see people who were my peers go off and then be their own founders. And so I would say to myself, well, why aren't I doing that? They're higher on the financial hierarchy than I am, and it's just really hard to step out of that. I think one trick that I really just learned. The other day, I read a substack article by somebody else who said, when you Find that inner voice is beating yourself up, like, why aren't you this? Or why'd you do that? Or you're so dumb. And if you actually say it out loud or even better, talk about it to your best friend or your spouse or partner or whatever, it all of a sudden loses some of its potency. It's a way of putting it in perspective. So I think if you don't combat it and you're successful and so you're getting this positive feedback loop, you just want more and more and more. It's addictive. You wonder about people who are workaholics and they don't spend a lot of time with their families. And, well, when they're at work, if they're successful, they're constantly getting positive feedback. And that's not necessarily what they're getting at home. They might be getting some positive feedback, but they're also probably with the people who know them the best and are calling them out when they need to be called out. And they don't get that at work. And I can remember coming home sometimes, my wife, who's perfect, Deborah, and part of her perfection saying this, because I think she'll probably listen to this at some point, would call me out on why didn't I do this? Or you left this mess, or how could you be so blind? Don't you see the garbage? Did you just walk past? It needs to be taken out. And I would think to myself, you know, at work they never say things like this about me. And now I look back and I'm laughing, because you need that balance. You talked about being an ambivert. I am a non shy introvert, so I'm usually pretty confident when I'm talking to someone or a small group of people. But if I'm around a lot of people too much, or if I'm away from home especially, I get homesick, I get lonely, my batteries run down. So now I can look back and say, I wouldn't have been happy being kind of a road warrior, or out every night, which is necessary if you're starting your own firm, I guess, unless you find a partner who will do all that stuff. I'm a homebody. And so it worked out well. I was home every night for dinner, which is not a typical finance industry story, and spent a tremendous amount of time with my kids growing up. And that balance has worked out really well for me. And it wasn't necessarily intentional. It was just a feedback loop. And it's what I felt comfortable doing. So I don't know if I drifted away from the original question or not. We were trying to talk about, you know, greed and I think you a combating it's really important realizing that it's a force inside of you which took me a long time to even recognize. I actually think people in their 20s and 30s have more self knowledge than I remember myself having. So I, I think also you tend to think about the people around you and what they're doing. And so if you see people doing things that are a result of greed, even to go into gray areas of ethics or even cross the line, that tends to be infectious in a negative way. Avarice is something to watch out for, particularly if you're in the finance industry, which is all about making money. It's a threat to your soul, if you will, but it's also a necessary ingredient to motivate you. There are two sides of it. If you have zero desire to make money, you're probably not going to thrive in the finance industry. It's interesting in one of your pieces that I talked about earlier when you were referencing Keynes a lot and imagine there's no scarcity, you share how he had postulated that kind of avarice, greed, this ambition, it's actually necessary. It's a necessary ingredient in this capitalist free market system for it to maximize velocity of prosperity. But then once you arrive at the post scarcity moment, then that greed becomes vestigial essentially it now becomes unnecessary. And he said it'll become morally repugnant and really interesting language that he had. They'll be committed to like the therapists essentially. Right, because they're still being greedy even though there's no, there's no need. Right? There's no reason now it, it no longer serves us, this kind of idea. I haven't read Keane's work on that yet, so I really enjoyed that essay and I have a lot of reading to do following that essay. But it struck me because I've wrestled with the same idea that this desire for more, for growth, for achievement, et cetera, it is driving so much progress. But at some point do we reach post scarcity. At some point do we reach a world where there's enough for everybody. Food, water, shelter, education, healthcare, we, through technological innovation, economic innovation, through hard work and learning and evolving as a society, we did it. We did what we set out to do collectively we made a world where all of us can thrive, at least in material circumstances. I personally view that as a real potential outcome like that. I don't view prosperity is asymptotic in absolute terms. I do think the relative scarcity status comparison that you talked about in that essay will still remain. And then I think it becomes this really urgent thing to tackle. And I'm curious, like, kind of reactions you've heard, how you've seen people react to that idea. Because when I bring that up, some people are like, yeah, that makes total sense. Like, if you just logically play out capitalism, that's how it should net. But then some people are like almost upset at the notion that you could possibly ever achieve a post scarcity world. How do you navigate the questions of meaning in all this? I'm skeptical about post scarcity world because there's always a top 10% and a bottom 10%, right? That's fixed mathematically, logically. And we have in the United States today a real widening of inequality. And a lot of the angst is based on relativity, not only looking at where anyone is relative to others and the way they live and what they can afford and the type of life they can afford, but it's also looking at the wealth of a country and a sense of that this country, America, for example, could afford to have a much more robust safety net. If you just look at our GDP and where we are, we could afford that. I mean, that's what the numbers suggest. We'd have to raise taxes and maybe have like a European type of system of a safety net. I think that you reach a point where you might take away some of the worst aspects for most of the people of absolute poverty. The vast majority of people in the United States are not going without food or shelter, the very basics, but the knowledge that society could provide a lot more and is not. And at the same time, seeing the people at the tippy top lead almost a completely different life, at some point that either gets cured peacefully, like the first Gilded Age did with progressivism and different labor laws and more of a balanced approach, or something breaks in the system and you've got populism and you have real damage to this engine of capitalism. I mean, that's sort of what Marx predicted, and thankfully he was wrong. But if we keep on going, we don't want to prove that Karl Marx was right after all. I really worry about that because I think we're in a situation where there really have to be political solutions. And I don't see that coming. As I think about it, I've been wrestling with it a lot lately, like this notion that when you think about capitalism as our best system yet, which I've said several times, Here, one thing that we also share with our students is capitalism's not perfect yet, right? It's not perfect. The economic system keeps evolving as our circumstances keep evolving. You've talked about guardrails. One thing we put forth to our students is the sort of financial system itself can maximize human flourishing by profitably allocating capital to products and services that meet real needs for real people in the real world. Right? It's sort of. It's the win, win, win. You know, we can profitably drive growth that also maximizes flourishing, real flourishing. And then we also talk about, you know, that the individual, that's the institutional, structural systems level. And then at the individual level, can give our time and resources to those in need. And even if we're not wealthy yet, we can volunteer, we can help something, and even a little bit of capital can go a long way. As I think about that, it's sort of putting forth that those of us with resources need to know what our definition of enough is. Right? We teach our students, greed is I need more, I need more, I need more. And the three antidotes are contentment, gratitude, generosity. Contentment. I have enough gratitude. I take joy in the enough that I have, and I'm happy with it. Generosity. I actually can share with others and live from abundance. I'm curious for you. How do you define when you have enough? This comes back to the combating greed discussion earlier. How does one know when enough is enough? How does one stop the comparison? How does one stop the relative scarcity? If you're able to, within reason, live the life that you want to live and provide for your kids and the way that you'd want to provide for them, you then have the ability to not necessarily make more material wealth or income your overriding priority. So that's part of it. And you get accustomed to a certain way of life. It's very hard to. It's hard to downsize your life. It just is. Part of enough is feeling like, I can step off the treadmill, if you will, and still live the life that I've been living and want to live. That's a very rare luxury, if you will. And so you then think about, well, if I can do this, how am I going to structure my life? What? Get back to Keynes, which is like, okay, what do people do when you don't really have this scarcity? You know, one person's scarcity may not be another person's level, right? If you as an individual reach the level where you no longer have to work at a job to provide whatever enough is, you then have to ask yourself, well, what is the meaning of what I'm doing? What is my relevance? And you can definitely find relevance in your family and in your friends and in pursuit of other vocations, whether it's writing or anything else. But if you're not helping other people, I feel like it is the absence of justice. It is injustice. So I always think to myself, there's a very famous quote from Rabbi Hillel of if I am not for myself, who will be? If I'm only for myself, what am I? If not now, when? So people like me think that that quote summarizes a lot of the meaning of life. You have to be for yourself. And I kind of incorporate into that. You're for yourself and you're for your family. But if you're not for others, it's sort of like, what are you? What have you done? And I think at this point in my life, if helping others who I don't know, who are not part of my family, if that wasn't present in my life, I would feel bad about myself. I would feel unlovable, as Adam Smith might say. I'd feel like not a good role model for people who knew me, for my children and so forth. And by the way, I know that a lot of your audience is younger, younger than you, 20s, 30s. I think that's right. You have other people who are older as well in your audience. But I think that it's important not to beat yourself up about, well, what am I doing to, you know, heal the world as I'm embarking on career and maybe starting a family. And there's time. There's time. But it is good to get in the habit of thinking about opportunities to do a little bit here and there. And it's almost like getting in the habit. When you graduate from a school, the development office just wants you to give something. It could be a dollar, it could be $5, it could be $10. Cause I know if they get you in the habit of it, right, and you end up being someone who can give a lot, you're much more likely to give. I think it's the same thing. You get in the habit of just doing a little bit. That's a good habit to get into. I appreciate you sharing that. A lot of people are surprised to learn that almost 3/4 of our listeners are over the age of 40. I didn't know that. Or maybe you told me and I forgot. No, I didn't tell you that. I should have tell all of our guests that a lot of people assume, I guess, that it's mostly students. It's about a quarter students, young professionals. And we built this for our students. And to our surprise, a lot of very senior leaders listen to the podcast. Almost every episode we get a text from the CFO or CIO at some multibillion dollar public company. Really like this interview. Favorites so far. Did not expect that speaking to the younger audience though, who are listening. I will share from my personal experience. I just, I agree with what you're saying. The importance of building the habit. Maya and I just bought our first home. And we're in our early 30s. We're in the Bay Area. We really had to stretch ourselves to be able to buy a home here. And I was wondering, how is this going to affect me? Like, how is this going to change my life? And what I didn't expect was that it placed on my heart this invigorated, deep desire to be generous, born out of an awareness of how blessed we are to even be able to afford a home. And so Maya and I pledged several percentage points of our income to pre tax to charity. I know in one of your sub stacks you shared that you and Debbie give 20% of your income pre tax, pre write offs to charity. And I want you to know I hold you up as a role model. I want us as a family to try to get to 20%. My dream would eventually be to follow in Buffett's footsteps, sons, the $100 billion net worth, probably, given my line of work, 99.9% of his income going to charities, being put into philanthropic trusts. I listened to Lawrence Cunningham's collection of all of Warren Buffett's essays in Q4. And now I'm finally listening to Poor Charlie's Almanac right now, as I was just listening to it this morning. And Charlie even talks about Buffett. He's like, you know Buffett, he's not earning because he wants to earn money. He's giving it all back to society. He just wants to build a platform where he can share his notions and ideas. I'm grateful to Buffett that a lot of his notions and ideas were about better business, social responsibility, more transparency, more integrity, more economic efficiency as well. For myself, me and Maya, we talk about this. I'll share this publicly for the first time. It's still fresh. Just in the last week, we're driving around the Bay Area and I see houses that are 2, 3, 4, 5 times the size of our little starter home. And I think, man, What a nice house. What a beautiful home. I could have my own office and we could, we could absolutely have two or three kids and I'd never have to share an office with Maya. And I'd have my own personal space. And I noticed it. I literally, we literally just went from a one bedroom apartment into a three bedroom home. And a month in I'm like, oh, but that house, ooh, it's, you know, I can feel it. And I've talked to Maya. We're like, we discussed this. I share that. We need to talk about it. We need to recognize that avarice, that covetousness within us, to use religious terms that, you know, people might associate it with, to be aware of it, to acknowledge it, to recognize it, and to just keep counting our blessings, to keep practicing gratitude. Do you find yourself, you talk a lot about in your writing, you know, how the, how the wealthy sort of self justify. They create a whole variety of self justifications despite the injustice, the, the inequality we see in society. Do you see sometimes that in yourself? Do you catch yourself kind of justifying? How do you wrestle with the self justification and then how do you kind of pushing through the discomfort, grow your generosity and in real action combat it and do something about it? Well, you know, I think I still beat myself up sometimes for missing an investment opportunity or something like that. And then talking about it makes me feel like I'm being kind of ridiculous. And it's very lucky to have. You have your wife, Maya. I have my wife. I can talk to her and she can listen to me. I have lost the material covetness at the age of 63. It does not much that I really covet in that regard. But that certainly wasn't the case, you know, in the past. I would, yeah, absolutely. Oh, I'd like to move to, you know, this apartment or get this or that. I mean, yes, I think that what I'm finding about getting involved with organizations where I feel like I or my wife are really making a difference, it's actually pretty hard work. Because when you can make a difference giving to a huge university or a hospital, you're really trying to support a grassroots organization. And you can see the impact of your contribution, not only financial, but just like using your network to helping them, using your experience to help guide them, it's actually real work. It's not so dissimilar to like thinking about a for profit company and where are the strategies. And I think in a properly run, not for profit, there's a lot of similarities with a properly Run for profit in terms of a board and governance and so forth. And it's not all roses, right? It's not necessarily glamorous. But at the end of the day, the service that you're enabling, you can really see that change lie. I'll give two recent examples. So we have a house out in East Hampton, and a few years ago, I read an article about homeless people in the Hamptons in the woods. And there are migrants. So there's. In this area known famously for its affluence and maybe its glitziness, there are really, really poor communities. They're the migrant workers who are homeless. There's also a Native American reservation right in the midst of Southampton. Many of them live lives in houses that are black mold and crumbling and very old. And then a mile away is $50 million mansion or something like that. And so I've gotten involved. I joined the board of that. You know, as you said at the beginning of this conversation, we have almost record low temperatures. So the executive director went out into the woods to find people who were in structures like tents and so forth, probably at risk for disease and freezing and perhaps even freezing to death, and brought them into motels. That's one of the things that this organization does. And I was really thinking that it could have saved lives doing that today. This morning, I was meeting with two heads of an organization that we're involved with, people who don't have the proper immigration documentation. The undocumented, I'll say, are detained if they don't have a criminal record and they have roots in society. They are sometimes given by the federal immigration court the opportunity to put up a bond, to leave the detention center and be outside that system and await the adjudication of their case. But the catch is that the bonds are like $10,000, which most of the people can't afford. And this is an organization that puts up the bond for these people. And each bond that they put up changes that person's life. They're working within the system because it's a federal judge who said, yeah, you can go free. You just need $10,000. And what happens is 95% of the time, the money comes back, participating in that and hearing what the incremental amounts of money that this organization gets. Some of the stories are just like, you know, and I don't have to pay the money back. No, you just have to work with your lawyer. And sometimes the case will result in the person being allowed to stay in the country. Usually takes many years, and sometimes they'll have to leave the country, but they're not in jail, essentially. Now, what I heard this morning from the people running the organizations, and this gets to guardrails and greedy. There are a lot of scammers out there who put on Facebook ads saying, hey, I'll help you. If you've been detained, come see me. And sometimes they're not even lawyers, and sometimes they'll say, yeah, I got you a bond. You just have to put up the money. And the bonds will be forged. They will be fake. And I saw one instance today. The people running this organization showed me as an example of a fraudster created a fake hearing in front of a judge with AI characters just to prolong the fraud. So on the one hand, you've got these two leaders of this organization doing tremendous work, really changing people's lives by getting them out of jail so that their lives don't blow up and they can go through the system. And then you've got these people who are preying on people at their worst moment. So it's like two sides of our system. And so we need more of the people who go out into the woods and prevent people from freezing to death. First of all, thanks for sharing both of those stories. They're extremely compelling. If those executive directors of those organizations are listening, thank you for the incredible work that you do, full stop. I was thinking as I was listening, and what was striking me was thinking about those stories is what the sort of optimal motivation for an economic system is at the micro level, the individual level, what motivations and behaviors collectively lead to the best outcomes. And we talked about how, you know, greed or just desire for more, for achievement, for accomplishment. It has been a galvanizing and driving force in capitalism, in our economic system, but it has all of its risks. It's listed as one of the vices, not one of the virtues or, you know, in any moral system over the last 2,000 years, for, I think, reasons that are intuitively obvious to people. And I often think about what's the better fuel. And I always come back to compassion. I keep coming back over and over again, both in my studies, in my private reflection, in conversations with people I admire. It just keeps coming back to compassion. And there's so many ways you can kind of substantiate it. You know, that's one of the virtues. It's one of the ultimate virtues in all religious and moral systems over the last 2,000 years, even from just, you know, basic game theory, prisoner's dilemma, right. If both players are collaborative and trying to Help the other. They both maximally benefit. We're a social species, collaborative pro social behavior is good for us. There's survival benefits. You apply K's categorical imperative. You often coach me to think in terms of counterfactuals or inverting thinking. I love K's categorical imperative. It kind of along the same lines like if everyone on Earth was maximally selfish and greedy, what would the world look like? It'd be horrible. If everybody on Earth was maximally compassionate and others centered, what would the world look like? It would be amazing. We'd all be walking a planet where there's 8 billion people who want to help us, you know, and want to make this planet better for everybody in it. Sometimes when I share that, one of the pieces of pushback I get is, well, it's not going to push us as hard. We won't innovate as much, we won't drive as much progress. And I just have yet to see any, or at least I haven't learned of any evidence that proves that. I look at my own life as an example. Cut my compensation by 60% six years ago to leave SOFI and run my nonprofit startup full time. And I'm not any less motivated. If anything, the more that I've tried to cultivate compassion and the more that I've combated greed in my own heart and mind, the happier I feel, the better my relationships become and I'm working just as hard as ever. And if anything, I'm a better leader, I'm a better coach, a better manager, a better executive, a better husband. Compassion is the fuel and the motivation, not greed or self interest as the fuel. And it's interesting, like I think a lot of times when we talk about justice, inequality, greed, it can almost. I think some people, people with means can feel turned off because it can feel moralistic or patronizing. And there's almost like this duty, like you must, you should, you must do this or you should do this. There's an ought in it, and I do believe morally there is an ought to associated with generosity. I do think it is in our collective and individual best interest. But it's the more and more that social scientists and psychologists and leaders with labs at universities across the world study human happiness. The more that we're learning that when we're generous, we're happier, when we're compassionate, we're happier, when we have good relationships, we're happier. I almost wonder if the conversation about generosity is more effectively delivered to other people that have means and influence. Not from an ought or should, but from a. We can we get to. We have the amazing opportunity to. What do you, what are your thoughts on that? Sorry, I've been verbose. No, no, not at all. Well, I think that I recently read a line that when you're benevolent, that was the word used when you're benevolent to someone or something, you become more fond of that, right? It's the human desire to tell a story. Well, we do a favor for someone or we help someone and we like that person better. I think that it is a key to relationships to, you know, want to help somebody. You think about the people closest to you. You know, a friend calls up and you can do something for them, you're going to do it and you're going to feel better about that friend, not worse after you've done it. Because if you didn't really love that friend, maybe you wouldn't have done it. So you must love that friend. It's kind of an interesting thought pattern, but the reverse holds true. If you, maybe you fell down on the job of being a friend, let's say to somebody, you're probably going to have this instinct, well, maybe I. That person's not so great anyway. So it's like the justification, which is a long way of getting back to, you know, you talked about justification and I think you have to be very careful about that when you're successful because there are many examples of people, probably many more examples of people who feel that, that luck didn't play as much of a factor or circumstance didn't play as much of a factor. And it's more self satisfying to believe that you deserve the good fortune because then you feel less, maybe less guilty or why should I get this? And then from that you also get, you know, surveys where unfortunately a lot of people think that people who aren't as successful, who are, let's say below the poverty line, are there because they didn't try hard enough. It's interesting, I think of our mutual friend, the governor of Maryland, wrote in a book, Gwess Moore. He wrote a book about a period of rioting in Baltimore and he was on his way to give a speech and to be lauded for his biography, how he overcame single parent to achieve all these great things. And his worry was, am I being used to show that anyone could do what I did? If you did start from a position of poverty or having some things against you and you didn't succeed the way that I succeeded, am I telling a story that's going to hurt people. So give him a lot of credit for thinking that way, because most people would think. And I'd met people who said, well, I didn't start with anything and look at what I accomplished. And so the people who don't have anything now, they're just, you know, pick your adjective, they don't have it, whatever it is. So, you know, you have to acknowledge that there's a lot of luck and variation and if you've been lucky enough to be given a head start, as I was, you just, you know, you just have to have to accept that and say, life isn't always fair and you play the cards you're dealt with. And just because you are materially well off doesn't mean that you're going to live this terrific life either. Yeah, right. Big shout out to Wes if he chooses to listen to this. Wes, thank you for being a moral exemplar for all of us. And go Wes 2026. We're on your team here to help and I appreciate you sharing that, David, because I was talking to Howard Marks recently. We had Howard Marks on our podcast last year. We had several one on one calls last year. We just had our most recent kind of mentorship call advising call last week and I was trying to share with him a summary of some of the principles I've derived from our conversation. And I shared a few principles and he said, Ross, that's an excellent synthesis. And remember, everyone are unique people in unique circumstances. It's difficult to arrive at hard, fast rules that don't require nuance in their applications. And I was like, thank you Howard. I appreciate that not letting me become simplistic in my thinking and listening to you share what strikes me is yes, hard work motivation can be mapped to some distribution curve of some shape. IQ EQ can be mapped to some distribution curve of some shape. I'm probably on the below the mean on eq, so I could attest to that distribution curve. But so are starting point material circumstances, luck, all these other things map to some distribution curves of some shape. The human system is grand and complex and there's trillions of permutations of circumstances. 8 billion plus permutations of circumstances for us humans. What I often times try to do is derive what are some rules or principles. Call it virtue ethics. What are some virtues or principles I can choose to live by that seem to check out intuitively, that feel emotionally and morally good, but that logically makes sense and are coherent and can stand up to different tests and frameworks that I hope others would want to emulate. I keep coming back to compassion like, I call it a dream. Call me still idealistic, because I haven't had my youthful idealism beat out of me by life yet. And I'm trying to never let it go, trying to just balance it with wisdom and knowledge. But I have a question for you, so. Oh, sure, yeah. What would be an example of compassion that you've kind of felt naturally? And then what would be an example where you've questioned why you didn't feel compassion? That's a great question. Compassion that I feel naturally. There's an example. I was at Princeton for one of our leadership symposia, our Scholars of Finance leadership symposia. And during the event, there was a break between sessions. I just moderated a panel of some very senior leaders that support the mission. And several students line up and want to say hi and chat. And one of the students came up and approached me. He seemed like he was on the verge of tears. And it was subtle, like he. Like he was hiding it. He was doing a good job of hiding it. But I could just sense that he had intense emotion, welled up as he approached me and said, ross, I really appreciated what you shared in your own life story and journey. Overcoming challenges. I didn't see my father for a decade growing up that really inclined me to trying to make the world better. My own experience of suffering growing up. And he said, you know, I've had some circumstances in my life that I. I'm not fully sure how to navigate, and I'm wondering if you'd be open to chatting. And I kind of. I leaned in closely and I was like, yes, I have all the time in the world for you. Either take my email, take my phone number, we'll get a full hour. And we had a number of phone calls where he opened up very vulnerably about real struggles with his family, real struggles with mental health. And we worked through that. We process through that. He's done very well. He's been very successful. He navigated all of those. That compassion just felt natural. And I think it felt natural because it pulled on my own heartstrings and my own kind of self identification. Right. He was experiencing some challenges I myself had experienced when I was younger. But for some mentors and people who invested in me, I may not have overcome. It was almost this joyful sense of eagerness to pay it forward. There are a lot of times where I'm not compassionate and I question it. There's a pattern that I'll Share when people are mean or rude. I was pursuing a career as a professional boxer when I was in high school, I. I did mixed martial arts. Most people can't believe that when I share because of who I've become today and I don't look the part necessarily anymore. It's funny I share that because when people around me are mean or rude, whether in corporate settings, on the street, in a restaurant, to a waiter, in any context, especially when it's someone with call it more power or a little higher on the hierarchy, being mean to someone lower on the hierarchy, I just feel this fire in my chest. Anger, anger. And instead of a compassionate response like that's a person that's probably in pain, that's probably has really hard things going on at home, that didn't have the same mentors that I've been able to have, that brought me to a better path. I just think if I wasn't the CEO of this organization and I didn't have a reputation to maintain, you'd be learning a lesson the hard way. Right? You know, like, does that answer your question? Yeah. And I think it's seeing someone being a bully and basically saying, that's wrong. That person lacks compassion. So I'm going to lack compassion for that person. Which I think is completely natural. And I think everyone could relate to it. I think also in your story, not story, but in your anecdote about the person who came up to you after this symposium. I think that sometimes it's very hard to feel compassion when something is far away and is not in your immediate circle. I was thinking about this because I read about there was a terrible train crash in Spain a week or two ago. There was a high speed rail accident and quite a few people died and it happened in Spain. It just was like I read it and then I noted to myself after I read it, like it didn't really affect me because it just wasn't accidents happen, Train accidents happen. It was like you just are glad that you weren't on that train. You know, I didn't process it as well. There are all these grieving families in Spain because there's all all this other stuff going on in the news. And so sometimes I think it's impossible to be compassionate about everything. You have to pick your spots. If you're compassionate about everything, maybe that's similar to being compassionate about nothing. You might be paralyzed with compassion. And I appreciate you pointing out that with abstraction there's less empathy and less compassion. Like our neurologically, our empathy circuits are designed to activate when we're face to face with another person or creature. Yeah, well, we spent most of our evolution living in these, you know, small bands, and we knew everybody. And so if, like, something happened to somebody 10 miles away and for some bizarre reason we knew about it, it's like, oh, right. You know, one, our former chief impact officer, Miranda, who's just amazing, she was really a very strong advocate that we encourage our students to work with the poor and the homeless directly to keep those empathy circuits active. Doing some research on it and just thinking about this, I came to believe that empathy is actually a requirement for moral reasoning. Any moral framework or system is ultimately, I believe, utilitarian or consequentialist. At the end, all of our decisions are therefore measured by how much does this make other people flourish or suffer. And knowing whether or not someone's flourishing or suffering requires empathy and empathetic awareness. So without empathy, we literally cannot morally reason as a social species. Well, then in our field in finance, we're looking at spreadsheets and numbers and pitch decks. There's so much abstraction. There's. It's a lot of large numbers. It's a lot of words on a page. It's not a lot of suffering humans right in front of us. And abstraction turns off empathy. Right. So I think, given that, I think people with my plug, my. A plug that I. That's coming to me as. As we're talking to anyone of means and even our students listening to Build the Habit to your point earlier, is volunteer in their local community, spend time with the poor. I keep in our glove box, we keep a stash of aloha bars. And every time we pull up to a stop where there's a homeless person on the side, I always invite them over, give them a few protein bars, just say, what's your name? How you doing? I hope you'll pay this forward. You know, good luck today. I hope things turn up. And even just that moment of interaction, I think it keeps us grounded in the reality that billions of people are currently facing on earth. Today. I want to ask. I know we're coming up on time. I just would love to invite you to share any final thoughts for our listeners, to encourage them to be generous, to give back, make your final case for why we should all be trying to help and give back more as leaders and future leaders in finance. My final case will be the famous butterfly effect, where, you know, the flap of a butterfly's wing could do something to the atmosphere to cause the world to change. I think that's true. I think the smallest act, you just never know what a kind word or giving a protein bar might do to a person's day and might change it. It will change it one way or another. Or conversely, if you do something that is hasty or something that you regret, that can have a negative effect. So, you know, I think about some of the things I remember as a child. It's very random what I remember, right. It's just like some very random moments. And as a parent, I would remind myself of that and maybe terrify myself a little bit because I don't know what my kids might remember or not. Which means that you always should try to be as much as possible on your best behavior and realize that you might be in a moment that will have a huge impact. And so I think that's why we should be generous with our time and our spirit as much as we can. No one's perfect. We'll all make mistakes. We'll all have our moments of temper. I never had aspirations to be a professional boxer, so no one has to ever worry about my temper. And I can't imagine you, Ross, having a temper. But my final pitch would be the butterfly effect. We're always having a greater impact than we may realize. And being generous with your time or your resources, you just never know. You might be saving a life, literally. David, thank you for the very powerful closing note. I think that's a perfect note to end on. I'm taking that to heart. I'm going to be more aware of how I'm showing up in every moment with our students, with loved ones, highly imperfect, as well as anybody, as flawed as any anyone else. Ross, you don't have to worry. You're one of the nicest, most caring people I've ever met. So, David, this was awesome. I'd love to do this again in the future. Thank you very much, Ross. It was a pleasure. I loved our conversation and I hope to be invited back. Thank you for your support of our mission. We're very grateful. You and Debbie, your whole family. Thank you for. For supporting us and our students. Then you will be invited back, surely. Thank you. Thanks very much. Cheers. Thank you for listening to today's episode of Investing in Integrity by Scholars of Finance. I want to share a huge thank you to our advisors, directors, donors, team, and our members who make this all possible. If you like this episode, please leave us a review review on Apple Podcasts. And if you have any feedback for us, you can send it to hello, scholars of finance.org or by visiting our website. Until next time, please join us on our mission to inspire character and integrity in the finance leaders of tomorrow.