James E. Hughes, Jr.: Great Advisors Offer Courage, Not Just Knowledge, The Five Capitals, 100-Year Thinking, and What It Takes to Help a Family Flourish
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The transcription features a conversation where the speaker reflects on investing as an intellectual challenge requiring emotional resilience and a balance of optimism and risk awareness. The speaker credits J. Hughes as a mentor who bridged the gap between purely financial analysis and understanding the human stories behind wealth—families, their needs, and worries. Hughes’ journey began with childhood exposure to the "shirtsleeves to shirtsleeves" proverb, reinforced by a 1974 meeting in Singapore where a Chinese gentleman sought help avoiding three-generation wealth loss. The core fear for wealthy families is the loss of capital, both external (financial) and internal (family cohesion), often leading to failure within three generations due to poor joint decision-making. Hughes emphasizes a holistic view of family wealth through five capitals—human, intellectual, social, spiritual, and financial—with financial capital as a supporting tool, not the end goal. He stresses the importance of joint decision-making systems, noting that most families fail from "cold inertia" rather than conflict. Modern demographics, such as fewer children and childless couples, are reshaping family dynamics, with wealth often passing to nieces and nephews, and the traditional role of aunts and uncles being lost. Finally, Hughes advocates for a long-term, hundred-year mindset to counter instant gratification, drawing parallels to historical civilizations like Rome that declined through demographic shifts. The conversation underscores the need for advisors to provide courage, not just knowledge, to help families navigate these complexities.
I came to investing for the intellectual puzzle that it presents. It takes a certain emotional makeup to navigate it with some success, especially over a long period of time. A well-balanced, fine-line experience of being open to opportunity, staying optimistic about the future and its promise, and being respectful of the past and what it took to build what we care for, while weighing risks in the process. I stayed in the profession, grew in it, and expanded because of the people I got to meet, work with, and serve. J. Hughes has been that intellectual and emotional bridge for me, a guiding light from just looking at the numbers to seeing the people, the families, the stories, the needs, the worries, the concerns. These individuals, these families, are on a quest to find a person. J. has many ways to describe that role. Once you see it, you can't unsee it. Once you meet someone who can serve in that role, there's someone worth holding onto, almost, for dear life. The investment profession gets oversimplified in ways that may not be helpful. It can be distilled into a collection of metrics that may be insufficient to capture the essence of a true trusted advisor's role. J. unveils the layers of complexity in the role one can have the privilege to play in a client's life. He also reminds us that what we're doing is not about the next month or the next quarter. It's possibly about the next hundred years. It elevates the quality of the decisions and the depth of thinking involved. Listen in and see why and how. J. has been a mentor to me for the better part of my career. He was also generous enough to indulge me and sit down for this rare interview, which we recorded over three years ago. We forgot that we were recording and what followed was a true hard-to-hard conversation between two people who really care about what they do. Take a moment, spend the short hour of me and J, share it with friends and family who would appreciate it too. Here I give you a dear friend and mentor and one of the most generous people I know. J. heuse. I'm boggling. I'm going to be short on this one. Our audience is going to be delighted. Finally, Mr. he's going to be short. My father said to me in the conversation that I treasure, early in my legal career, he was a lawyer of extraordinary ability, whose clients not only loved him, but everybody in the law firm that he led wanted to work for us. That those are two remarkable qualities. We were talking one day about what the nature of a professional is. So I'm going to use take the word advisor and I'm going to flip it to the four noble professions. Ministry, medicine, high academia, what is it to be human law, and then banking what it is growing human communities, not intermediate. These are the four noble professions, plus banking in this unusual way. My father said, J, a person in one of these noble professions, including banking in the way of growing human communities, he said, your clients will come to you seeking knowledge, knowledge is fungible and you'll provide it. But they will really be coming to you seeking courage to do something difficult. He said true person to call feels earn our living through providing courage. Look for an advisor who provides you with courage. [Music] Welcome to Talking Billions. We talk about big ideas, big inspirations, big topics. We take on the hardest topic of all money. How to make it, save it, keep it. But our conversations lead us to an even bigger question, what it means to let a rich life be on money. My guests share their practices, principles, and evergreen wisdom. I'm your host, Bogumel Baranowski, author, TEDx speaker, and investment advisor to wealth creators with patient capital and an infinite investment horizon. I work with families and individuals who aspire to grow wealth over lifetime and generations through disciplined, thoughtful investments in durable quality businesses, while giving money, meaning, join me on this quest to unearth and share the wisdom of the ages. Let me share with you the podcast program disclosure statement. Blue Infinite Escapital LSC is a registered investment advisor and the opinions expressed by the firm's employees and podcast guests on this show are their own and do not reflect the opinions of blue Infinite Escapital. All the statements and opinions expressed are based upon information considered reliable, although it should not be relied upon as such. Any statements or opinions are subject to change without notice. The information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies. Investments involve risk and unless otherwise stated are not guaranteed. The information expressed does not take into account your specific situation or objectives and is not intended as recommendations appropriate for any individual. Listeners are encouraged to seek advice from a qualified tax legal or investment advisor to determine whether any information presented may be suitable for their specific situation. Past performance is not indicative of future performance. None of what you're about to hear is investment advice. Well, hello Jay. How are you? I've been looking forward to this. You and I have known each other for several years and last few years we had the pleasure of talking every month and as you know you were a guiding voice for my last book, Money, Life, Family and you offered me invaluable advice and wisdom all around on many topics and for that I'm grateful. Good my pleasure. Today I want us to pretend that no one is listening and have a hard to hard chat about the many topics that keep coming back in our conversations. Family wealth as a topic. Where did your interest come from? How did you get started on this wonderful journey? Pokemon there are two main moments that got me going. The first is when I was four years old. I overheard my mother and father having a someone he did conversation. My mother was agitated. He was about money and that money money. They weren't they were not wealthy people but my father was a practicing attorney and speaking good living for that time. But my mother's father had gone bankrupt in the depression. I put all his money in his father savings bank and the savings bank went down. So for one day to the next literally she left school in the morning from a lovely home that had helped and came home to the afternoon to a four sales side. This affected her all of her life and so in this conversation with my father she mentioned the shirtsleeve to shirtsleeve's proverb. Her grandfather, my great-grandfather had been in a German immigrant and better. I came to America and did very very well in the late 19th century. So I heard that proverb and it stuck with me. Shirtsleeve to shirtsleeve since they're generations. In 1974 I found myself in Singapore on very odd reasons for being there. No idea why really invited you to come halfway round the world. Very strange. Oh mysterious I'd say. And sitting in front of this Chinese gentleman I had no idea why he invited me to come halfway round the world. And he said Mr. Hughes I want you to help me help my family avoid shirtsleeve's to shirtsleeve to three generations. Boom boom. Those two really synchronous conversations sent me on this path and the goal of her sense as you know has been to try to relieve families of that suffering and help them see wealth as well being and help them prosper. What do you think is the biggest fear that wealthy families have always faced? Well I'm not sure that there's, well there is one but it comes in two dimensions. One is external and one is internal. And that is essentially the loss of their capital. And by that I mean not the external loss through war or Holocaust or whatever it may be of family members and not simply their financial resources that support but the loss of the family members their cohesion. And then internally the inability to make decisions that enable the family to have future generations. So there's one problem in shirtsleeve problem describes the outcome either the external or the internal reality, but I think it's the same.
It's the same issue with just you face it two different ways. In your book Family Wealth, you write about the dynamic growth of families, human, intellectual, social, spiritual, and financial capitals. The investment profession often starts and ends with the financial capital. But you go beyond that. Could you share more about the other capitals? Well, if we really look at a family's self, the first thing we would look at ourselves if we were demographers as how many people, not how much money. If it was a family, we were looking at it had to be two or more people because you can have a single person household. You can't have a single person family. We'd be looking at the ages of those people, what the questions are that are likely to be the ages. Are there married in? Are there grandchildren? We'd be looking at them. And as we were looking at them, we would have a human experience, a qualitative experience that would emerge from our scientific study. We'd become humanists and scientists. We'd be looking at them that way. No one would look at them as their balance sheet in the financial context. Well, that's just obvious. But believe it or not, it is not obvious to the financial professions because the financial profession is laser-like looking at the financial capital. Obviously, that leads frequently to a lot of misunderstandings because what the financial people are looking at and managing isn't the family. It's its financial capital. The family itself is trying to organize itself. So one of the things, as you know, that I've tried to help families do is orient themselves by using a hand gesture, which I'll use now. So let me just say to the wonderful people that are going to be sharing our journey this morning with us, if your financial capital, your thumb, is wiggling up and your other fingers are like this, that is the death of a family. There's no family. You notice there's nothing qualitative there. Right. This has no purpose. Mm-hmm. Might help the financial advisors' personal balance sheet. If you turn your hand upside down, what immediately emerges is spiritual capital purpose, social capital joint decision making, intellectual capital, lifelong learning family, human capital, thriving human beings, and now Bogomel, the financial capital has a purpose supporting the growth of these. Those families go a long, long way. Well, it makes me think immediately if you remove the financial capital from the equation, can you have one happy flourishing family building all the other capital, more successfully? In other words, does money get in the way? Well, I think the best positions, rather than generalizing, the best position for a family is that it sees its purposes growing things. Right. It's nice to have this helping, but you needn't have these to grow these. And there are millions of families on the planet doing well as Tolstoy said, who you never see because they're doing fine, who are about growing these. Don't have much of this. Then of course, Tolstoy said, every family is going out of business, does it uniquely and very loudly. And those we see in the newspaper, or we see the Mazar neighbors when the lawn is mowed. So yeah. Why words, why advice? You emphasize the importance of good governance, decision making in a family. If a family is more than one person, how big of a group of people can effectively make decisions and if they can't with the, wouldn't the family naturally break into smaller independent units? Is that the right way to think about it? Well, let's pull this apart. This is a wonderful question. And there's, there are multiple parts to it where social anthropology, social psychology begin to enter in. There is a theory, Bogomel. And I think it's a very sound theory that human groups through the 350,000 years of our existence. Remember, they found us in Morocco 350 instead of Africa, well, part of Africa, he's Africa 250. It appears that there is a sweet spot for human groups of 150 people. That's, and the academy well known, it's not well known, I would say generally, but there, there is something about 150 people where human groups can grow to that successfully. And then when they seek to grow beyond that, there is some interior decision making issues that cause them there to be some independent activity. Now within that 150 people looking at joint decisions, we tend, because we're not social anthropologists, we're cultural anthropologists. We tend to look at the nuclear family and say, well, can it make decisions? Well, that's an open, good question. Again, it makes decisions, not always. But if it can make decisions, it learns a system of joint decision making. Then it probably can use that system to grow plans. That's not a bad thing, by the way, it's just a way of describing different households, the children's different households. And then if those households can make good joint decisions and choose to, that's a voluntary question, they might become a tribe. You see that? So nuclear family, plans, separate households, tribe. And then that tribe can probably get to 150 people making joint decisions. And then there may be some impetus, some centrifugal force that says, well, maybe those need to be a new tribe. Now that's not necessarily so. There are some families I've represented with 350 members making great joint decisions. So it isn't inexorable. But I would say that within that 150 number, it's quite possible. Now let me go one step further with this. It's a long answer, but one step further. The reason that I suggested that, over our conversations over the years, that this question of joint decision making is so important is that we have texts. I'm not going to mention here's not necessary, but we have texts in our field, TXTS in our field, that's a Twitter text, but books that make it very clear that something between 70 and 85% of families over the first three generations, that that shirtsley proverb that we talked about at the beginning of this morning, do not make good joint decisions and go out of business. Now what are the statistics tell us? Well, if a family doesn't have a joint decision making system or what it has one, but can't make it work, what an external taxes, compensation, all the cost comes or in total, there's internal disputes that can't make it work, then between 70 and 85% of those families by the third generation around a business. That doesn't mean there isn't some money around, but the family fabric is essentially either broken for heat, for fission, they blew up, or moral often, by the way, without a joint decision, they die from cold inertia. It's not written out quite so clearly, but you can find it that most families fail to shirtsley problem because they become cold, not because of heat, but that's all joint decision making. Fusion, Goldilocks's foods just right, is a good joint decision making system. Makes sense? Makes sense, makes sense. Can I add to that, you and I talked about the family changing. We have fewer kids and the pyramid, the demographics are changing. Does that affect how families manage their affairs? They don't have as many siblings arguing or having to find an agreement on anything. Does that change the dynamic a little bit? The makeup of the family has evolved? Well, I think there are two remarkably important things about modern demography that to be very candid, almost no one in the financial services, lawyers, backers, and countenance, etc., have paid any attention to. The first thing is that a lot of those families are simply going to disappear in the first generation by choice.
So, an awful lot of the planning process doesn't really take into account their choices as to how they will live their lives without children. And then how they will dispose of whatever financial capital they have. That's called inversions. And there's nothing in the literature I've been writing about it, but almost nothing in the literature and in fact the vast majority of people you go to to plan and think about it are still using systems that assume dispersion. Okay, so that's one thing that comes out of your question. The second thing that comes out of the question though is more complicated. And that is if you if they're if that couple chooses not to have children. I'll come back to one or two children in a minute, but let's just say for just to have no no children. Eventually they have to make some decision on the accumulated financial capital that they accumulated in their lives. Where that tends to go is to nieces and nephews. Not to philanthropies. Some goes to philanthropy. Now why nephews and nieces? Well, kinship. And that's look at DNA not blood no families have made a block. It's made DNA. Bloods are fallacy, but DNA is there. And so there is also joint decision making in those families. It's just not as obvious in the decisions that are being made. And so they're watching very closely how the nephews and nieces develop. Now also interestingly going one step further on that can think it's a very important point. In most human communities again, we went to social anthropology, vocable. In most human communities, it's the answer and uncles who who socialized in nephews and nieces, not the parents. Because of the inherent conflict between parents and children. And failures and modernity. If you will or the reality of living apart. Is that the roles of aunts and uncles have been lost. And that's a that is a human tragedy for the question of successful development of the nephews and nieces. It's a real human tragedy. Now you come back from all but I know so long answer, but so what we're having fun. I hope the audience is having fun too. When you get a parents and one or two children. That looks like a family that could have more generations theory could. The thing about one or two is it's still less than the 2.1s that you need to replicate yourselves. Right. So the joint decision making in those in that system may not have a long term path. Simply because the democracy may be against it having that. You're a real interesting question. And the modern demography is changing most of the things that even the academy understands about the families. And absolutely oblivious most families to the reality of the new demography. That you know we it's a little bit like the fish swimming in the water. We don't realize that the water we're swimming in is moms having 1.2 children around the world. We're still thinking of a mom's having 3 and 4 children. It's not happening anywhere almost. It's changing the family dynamic and tremendously. It puts a lot of responsibility on sometimes one single individual. Yes, it does eliminate some potential tensions among numerous siblings. So we might add here that the great problem the Chinese created them for themselves by the one child policy are the little emperors. Right. 4 grandparents, 2 parents, 1 child. A lot of attention. Yes, and and that little emperor has a strong opinions. Not buffered by any sibling experience. Well, in this age of little emperors, I'm thinking of the age of instant gratification shrinking attention span accelerated change. But you talk about a hundred year mindset and it might be needed more than ever. But the mainstream thinking couldn't be further from it. It seems. What can we do about it? Well, let me start by a subject that you and I have discussed very frequently. The ancient adding in history. The history does not repeat it rhymes. If we looked at role for a moment, people are saying, what's going with this instant gratification behavior and goes to role. Well, the Romans essentially bred themselves into the end of their civilization. So I started having two children and one and a half children and 1.2 children and they needed the barbarians are quote unquote, which means others not. Strange people to come do all the work, then they needed the military and out they went. So I think we probably not should we ask them what women to have more children. I'm not suggesting that no opinion. That's I think the birth control pill and women's ability to make their reproductive decisions is probably the greatest revolution in the world. That invention. But we have to look at the question of what happens when you have very, very few children. And then when you have very, very few children in a natural way is that your attention to them is greatly increased over your attention to them when you had four or five children as an example. This is not good for children. Now we have endless books being written for parents about the parenting. And the books, however, don't recognize the water these parents are swimming in is a 1.2 world. Not the world of three and four that they grew up in or may likely have grown up. So this is a really strange time for families because demography is it is destiny, right? We have the same issues as human beings have had for 350,000 years. We are that form. We are our psychology is a function of our species and our experiences. But we're in a really weird time. Not just for the family, but then for the simple for the children. Because of this over concentration. And modernity as you know, we get a lot of funny turns getting born like helicopter parents. Or now for the eye, Jen, the youngest group, not quite. There's some younger but the younger cohort. We have snowplow parents. What does that mean? Well, snowplow parents is a term developed by social anthropologists and social psychologists to define. The vast majority of children who fall into that cohort now. That the parents plow the road for them instead of the child being out with the shovel, shoveling walk. Now what do you get from that? Well, what we're seeing tragically. Is it one third of all freshmen in all. And the higher education institutions are in mental health services in the first semester of their rival college. That's the human catastrophe. And it's perfectly understandable that we don't have to look for the causes. To a certain extent, the problem is the effects. Creating human catastrophe. And so this demography, which I'm weaving through our conversation, but it's what isn't understood by people. Is having dynamic consequences. When we look at the family, which is the building block, by the way, of a flourishing society Aristotle said. I'm sure lots of our watchers will recall Aristotle said the fundamental building block of a flourishing society is a flourishing family. So that base of that flourishing society we don't like to live in and grow up in is are the.
family's flourishing. And the answer is the family is not only changing its by virtue of its demography and birth could wonderful choices people could make. But it isn't flourishing. When you talk about family wealth, you talk about a hundred-year mindset beyond the Shreds Leafs challenge. And with that context of a hundred mindset and a current backdrop of same-day delivery and everything happening in a minute, a hundred years seems so far away and such a foreign concept. It's very helpful in terms of thinking about an investment plan for a family, but it's very hard to embrace by the younger generation that you talk about, but by people in general these days. Why would you even think about a hundred years? Well, it's a hundred years is of course an aspiration. You could have said 250 years as an aspiration. What I would say helps a family think about this. And certainly as help my family think about it and many of the families that I've been able to share this wisdom. Bogomail in tribes coming back to something we talked about earlier. So family, nuclear family, clans, tribes, let's say up to 150 people. All over the world there are successful tribes. There are thousands of years old. I could argue that the Jewish diaspora is thousands of years old. I could argue that the Yamamoto or a major tribe in the Amazon are thousands of years old. I could give you lots of evidence that this is possible. Now it might not be logically available to our audience because it doesn't know Yamamoto's. I'm sure it knows some Jewish people, but it might not think about it this way. All tribes grow elders. Do we grow elders in modern society? Oh dear, that's an interesting question, Mr. Hughes's post or James's post. No, we don't. But tribes, successful tribes through all of human history and that's prehistory as well. I'm going back to 350,000 species. We tribes grow elders. And elders are interested as the chiefs for peace. By the way, they're not chiefs for war. That's what the boys do in spring. But chiefs for peace are the most important person in a tribe, aren't they? Because they're looking at the tribes long term survival and thriving. That's why elders emerge in an evolutionary way from an anthropology. They evolve because they're necessary or the ways it disappear. But if you disappear something that's necessary in a human community, you're in trouble. Aren't you? You're taking something out of your thriving equation that you need. Right. So what does the elder do? The elder is always thinking at 100 year increments. As that's the elder's job and is the system that the elder is not supervising, but rather maintaining and mediating. Elders don't make any decisions. They mediate experience. So that human community keeps thriving, keeps doing what it can't evolve to do in the environment it came to life to do. So these are people who are always thinking 100 years ahead. Now, for our watchers and we're saying, I can't think that way. I'm going to ask them to imagine for a moment, arriving at the most beautiful place that they go in life where they're absolutely happy. They're thriving place. You can ask them to imagine bringing with them people they love the most in the world. That's their tribe. They're sitting in that beautiful place at almost certainly in a circle, right? Or at least a semi-circle, maybe the elder sitting here and they're sitting here, but they're they're they're gathering. They're doing there's a fire, right? Of course there's a fire. People are gathering. Something's going to happen there. They can't wait to get there. And here's what the elder is going to say. And by the way, the Eroquois, the Hottosani, who are a 600 year old tribe thriving in America and Canada, the elder gets up and says something like the following. I'm not going to be exact, but it's close. So we're all sitting here together. We're going to make some decisions together. But the elder says the elder says, let's hope that the care and diligence and wisdom we will bring to our decision making today honors those seven generations of gold who made it possible for us to be here today so that those seven generations forward will honor what we do. All tribes do seven generations. There's nothing that keeps a new set of parents starting out a new genesis story. Every new set of parents is writing its own genesis story, right? It comes from somewhere. It has antecedents, but essentially it's writing a genesis story. When you and Megan stood on that beautiful cliff in that magnificent setting in Georgia, you were starting a genesis story. You may have been thinking about it, but I know that's what you were doing. I happen to be able to participate, which was an incredible thing by Zoom. But I have a feeling knowing you, you have 100 years thinking how many times have we discussed together in your parents and grandparents, almost every conversation? That's true. If we go back to when your grandparents were born, which is likely in the 19 teens or 20s, right? We just went back on, oh, we just went back a hundred years. Oh my goodness. That's right. How did we do that? At our our major in Bogomil, going to have a 50 year journey together, I hope 60, probably. Now we went 60 years that way. 100 years thinking in families is the easiest thing in the world to do as soon as we realized that we knew people who were born a hundred years ago or close to it. Right. And by the way, just to make people really fascinated, almost always they've asked their grandparents if they were lucky enough to know them about a generation before that or the grandparents just wanted to tell them about their parents or grandparents. And Bogomil, it won't surprise you that the families I help, including my own, do an exercise just for fun of storytelling, doing just what I said. And they go through about 250 years of their own history by going back to the oldest person and what they told them about somebody older. And then the 16, six year old who's sitting there is going to live to be 100, 250 years. Only families can do that. And that's our inherited oral tradition and our awareness of talks. 100 years is something. And I like it. I'm a big fan. I notice how it's a challenge in today's world where it's hard to keep somebody's attention. Be between two commercials three minutes apart and to have them pause and think about it. But I like the way you present it and the framework that you suggest how we already think in terms of a hundred or maybe 250 years to begin with. And we might not be as aware of it as we could be or should be. Yeah, I agree. You have a very clear idea of a perfect advisor to the family. And again, in an era of salesmanship monthly sales quotas, you have a completely different vision for a true on the confiance borrowing your term. Please tell me more. Finally, Mr. here's going to be short. My father said to me in the conversation that I treasure early in my legal career, he was a lawyer of extraordinary ability. Whose clients not only loved him, but everybody in the law firm that he led wanted to work for him. So I'm going to use take the word advisor and I'm going to flip it to the four for noble professions.
ministry, medicine, high academia, what is it to be human law, and then banking what it is growing human communities not intermediate. These are the four noble professions plus banking in this unusual way. My father said, Jay, a person in one of these noble professions, including banking in the way of growing in the communities. He said, your clients will come to you seeking knowledge. Knowledge is fungible and you'll provide it. He said true person to call fields earn our living through providing courage. Like that courage. As part of this interview series, I have conversations with wealth creators and wealthing heriters. And we spend a fair amount of time on the topic of childhood and upbringing and their relationship with money. Do you think we learn it all when we're young or can we unlearn it later on? Our relationship with money. Well, Bogomel, let me start and I'll try to keep this short too. But let me start by something that a great, great therapist and psychiatrist at the Accommod Institute in New York taught me nearly 40 years ago. Apparently Freud are great discoverer of the unconscious pioneer. Therefore, got something's wrong. They're young and other fixed, but that's pioneers destiny. Go look at it with the best you can. Sprite said something that my friend Peter shared with me 40 years ago that we he and I have been working out with many, many people in the cognate professions that serve families ever since. Lots of people know Bogomel that Freud said that the great human adjustment I he meant happiness but adjustment being who he was lies in human beings learning to love and learning to work. And by work he meant vocabulary vocation not labor labor. So I repeat he said the great adjustment happy people that he met in his profession had learned to love and learn to work. Everyone knows that that's taught in all psychology psychiatry and almost any institution trying to understand the human beings. Freud apparently said that Peter was very sure that he heard this that Freud went on to say that the two great impediments to adjustment slash happiness are sex slash gender and money. And that money is the most difficult to go all because no nice person will speak of it. That statement by Freud repeats itself in my life almost weekly if not daily in the questions that my clients and my friends and my associates and now the many, many people that come to me and were ideas and conversation. I believe Freud is absolutely right. I believe money is not the root of people know I think that money is an incredibly complicated subject for human beings. And I agree that my experience of teaching Freud if you will around the world and I probably I don't know use that expression in thousands probably by now of conversations that I've convened I find no one who talks about money easily. Now I may there may be people in the financial services industry who can talk about money easily but not when they're talking to their wives or husbands. And certainly not when they're talking to their children. And absolutely not when they're at the country club or wherever they're associating with their friends. And it's absolutely right. So getting the capacity in a family system to look at the question of learning love and learning to work as a quadrants and then sex slash gender and money as more quadrants and money is the lower right hand the one that's toughest of all or whatever, however you want to organize it. Realizing that is an enormous realization toward actually being able to deal with what the problems that Freud was talking about. So now a hint for our watchers and listeners. Some of the best advice I ever got on parenting with money is you're standing in a toy store with a child. And the child is. Nidalee nidalee nidalee. I want that toy. I want that toy. The one thing you must never say to the child is we can't afford it. And the child knows that isn't true. Because you'll never get back to even the great parents in that situation say, you know we're choosing not to have that today. Oh, it's that extraordinary. That is just so sound, isn't it? No lies talking about money and making it very clear that we have boundaries. And that and that doesn't say to the child, you'll never have it. It opens up for that child. A question. I can say in my own life, making this very personal for a moment, that my mother and father's post depression, uh, air appearance, uh, about my brother and sister and I earning things, not being given them. Although we did have wonderful birthdays and Christmases. I'm not no one was. My brother and I are fondest memory was earning the $75 which in 1952 was a lot of money to buy a robot so that we could have a clamming and crabbing and muscling business in the summer. What can you imagine any more fun and going out in a boat in the low tide and and crabbing and clamming and whatever and then walk up the street selling out your stocks. Well, these are not my experiences. These are these can be anybody's experience. But talking about money is so hard. The great thing about it is integrating it into a discussion by actions that are actions that enable temperance and prudence. The two great Aristotelian virtues. The one that is the most important in the confusion world, the frugality that the old one isn't being parsimonious or you can't, you know, height, like, silence, the martyr and no. But can we talk about money? That's Freud's great question and he's absolutely right. We can. We're not going to be happy in the sense of deep adjustment and serious happiness. So this question is hugely important and I would say, fundamental to happiness now I'll add one more thing. Lots of couples today, by the way, a third, no, about 40% in America already. The woman earns more than the man in her relationship or the, or the woman in her relationship. But I'm, this is, I'm looking for the moment of the heterosexual because we don't have the same statistics yet on the same sex marriages. What do you say 40% of the women in America in relationships with a man make more than the man's. You think any of our listeners said wait a minute. First of all, I don't believe it's true. Those are real statistics. And then they thought, but historically that's been really weird with the woman had lots more than the man. I bet those are hard relationships given the fact that men were supposed to go hunt and women have children. I don't mean that in a bad way that was actually our evolved psychology, isn't it? The women chose the men to have their children with who did more hunting. What's tough home. So, I think those couples are having a good time talking about money. I think either have an even more difficult time than Freud imagine because he was living in a world.
world were less than 5% of women were in those relationships. That's 40%. But he was right. We just have in modernity because of the magnificence of the changes in the capacity of gender to make choices and financial choices and partner choices. We never had, but never by the way, no human beings ever had those choices. You know, right? Crazy world, modern world with them. It's never been harder to talk about money, but it's never been more important to find a way to talk about it. I assure everybody that's true. Freud got this one 100% right. And you're speaking from experience. Exclamation point using my pencil as an exclamation point. Oh, Jay, I always see you as someone who has a beginner's mind and who continues to learn while you enjoy sharing the knowledge and wisdom with others. And that's the role your foundation has taken on, advancing the study of the family governance and generational well-being. What's your hope, your vision, dream for it, for your foundation? Bogumel, the donors who created this to my total surprise, it says, you know, nothing to do with me. When I asked them, well, I'm like, what am I supposed to do with this? They looked at me with joy and they said, you have to figure it out. Oh boy, I said, come on, give me no, no, ants. But basically then I did give some hints. And what they really asked me was, would I try to enable more families in the world to flourish? And I then added, well, it wouldn't be okay with you if in helping more families flourish or enabling them to do so hopefully that we would imagine then that they in turn would create a flourishing society. Right back to our friend, Aristotle. So that's our job. What we're attempting to do is to help more families all over the world, not necessarily with financial resources, just families, these people, as we were talking earlier today. Think through the questions of what is the water they're swimming in? What's the external reality? And how is it changing? How is it evolving? Well, just a minute ago, we said that 40% of the women in America make more than the men in their, in their relationships. That's a nice sounding sociological and anthropological change that no human beings ever lived in. So that water is different, isn't it? But we're trying to do is not tell anybody what to do. But we're trying to do is explore that water. The same thing as we were discussing earlier today about 1.2 children, instead of 2.5 or 7 children. What is that world going to look like? The 100 year thinking that you're asking, we're, we are trying to help people explore the remarkably wonderful questions you've asked me today. These are the foundational questions of the family. Families that are coming, their Genesis stories, families that exist. Families that are 3 and 4 and 5 generate, tribes are 100,000, you know, 1000 years old. What is their wisdom? What does the human experience actually enable us to understand about the water that a particular family is swimming in? And then not only how can they explore that water, understand it in light of how they feel about it because their feelings go back through shared evolved psychology and shared social experience. And then how can they themselves make better decisions? Do the things that enable them? Learn to love, learn to work, manage sex and gender, manage money and and prosper. And I mean by prosper, flourish. Can they reach their human's qualitative possibilities? Supported by quantitative. Jay, this was wonderful. Thank you so much for all this time and thoughtful wisdom that you decided to share with me and with our audience. I really appreciate it. Thank you. You are a wonderful partner and I am really privileged to have been asked today to sit with you and share the wonderful conversations we have monthly with all the people sitting out there in the ether, but maybe we can help. Wouldn't that be wonderful? And what would be? Thank you again by Properch. You were listening to Talking Billions. We take on the hardest subject of all money, but our conversations lead us to an even bigger question, but it meets to live a rich life beyond money. If you enjoyed the show, please take a moment and follow, subscribe, rate and share with friends and family. We rely on word of mouth from up the show. One click for you means the world to us. Thank you. Until next time, your host, Bookmill Baronowski. [Music]
Podcast Summary
Key Points:
Investing is an intellectual puzzle requiring emotional balance—openness to opportunity, optimism, and respect for the past while managing risks.
J. Hughes shifted the focus from financial metrics to people, families, and stories, emphasizing the role of a trusted advisor beyond numbers.
The "shirtsleeves to shirtsleeves" proverb—wealth lost within three generations—drove Hughes’ career, sparked by childhood and a 1974 Singapore meeting.
Wealthy families’ biggest fear is losing capital, both externally (financial/resources) and internally (family cohesion and decision-making).
Hughes advocates for five capitals
Joint decision-making is critical; 70–85% of families fail by the third generation due to poor decisions, often from "cold inertia" rather than conflict.
Modern demography—fewer children, childless couples—changes family dynamics, with wealth often passing to nieces/nephews, and aunts/uncles losing their socializing role.
A "hundred-year mindset" is needed against instant gratification, drawing on historical lessons like Rome’s decline from low birth rates.
Summary:
The transcription features a conversation where the speaker reflects on investing as an intellectual challenge requiring emotional resilience and a balance of optimism and risk awareness. The speaker credits J. Hughes as a mentor who bridged the gap between purely financial analysis and understanding the human stories behind wealth—families, their needs, and worries.
Hughes’ journey began with childhood exposure to the "shirtsleeves to shirtsleeves" proverb, reinforced by a 1974 meeting in Singapore where a Chinese gentleman sought help avoiding three-generation wealth loss. The core fear for wealthy families is the loss of capital, both external (financial) and internal (family cohesion), often leading to failure within three generations due to poor joint decision-making. Hughes emphasizes a holistic view of family wealth through five capitals—human, intellectual, social, spiritual, and financial—with financial capital as a supporting tool, not the end goal.
He stresses the importance of joint decision-making systems, noting that most families fail from "cold inertia" rather than conflict. Modern demographics, such as fewer children and childless couples, are reshaping family dynamics, with wealth often passing to nieces and nephews, and the traditional role of aunts and uncles being lost. Finally, Hughes advocates for a long-term, hundred-year mindset to counter instant gratification, drawing parallels to historical civilizations like Rome that declined through demographic shifts.
The conversation underscores the need for advisors to provide courage, not just knowledge, to help families navigate these complexities.
FAQs
J. Hughes was inspired by two key moments: overhearing his mother's anxiety about money as a child, tied to her father's bankruptcy during the Depression, and a 1974 meeting in Singapore where a Chinese gentleman asked for help avoiding 'shirtsleeves to shirtsleeves in three generations.' These events set him on a path to help families prevent wealth-related suffering.
The biggest fear is the loss of capital, which has two dimensions: external loss (e.g., war, financial collapse) and internal loss (e.g., family cohesion and decision-making). This often manifests as the shirtsleeves problem, where families fail to sustain wealth and unity across generations.
The five capitals are human (thriving individuals), intellectual (lifelong learning), social (joint decision-making), spiritual (purpose), and financial. Financial capital should support the growth of the others, not dominate, and families thrive when these capitals are balanced.
Modern demography, like fewer children or childless couples, is often ignored in planning. Childless couples may leave wealth to nieces/nephews, and smaller families may struggle to reach the 2.1 replacement rate, affecting long-term joint decision-making and family continuity.
Joint decision-making is essential because 70-85% of families fail by the third generation due to poor decisions, often from internal disputes or inertia. A good system, like a tribe of up to 150 people, helps families avoid the shirtsleeves problem and sustain cohesion.
In many human communities, aunts and uncles socialize nieces and nephews, but this role is often lost in modernity. This is a human tragedy because it impacts the successful development of younger generations, which is vital for family wealth and continuity.
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