The Meaning of Money
Chapter Nine
A Tool, Not a Totem
John Coleman on why money alleviates pain but cannot manufacture a good life
Read the transcript
Welcome back to The Meaning of Money. I'm excited today; I've got a really fun guest, John Coleman. John, welcome. Yeah, Stefan, thank you so much for having me on. It's a privilege to be here. John's a really fun guest today because, more so than a lot of people that I interview, he has actually spent time very intentionally thinking about the meaning of money. He has written, in the Harvard Business Review, Good Money: Six Steps to Building a Financial Life with Purpose. And also, most recently, or before that actually, the HBR Guide to Crafting Your Purpose. As if he doesn't have enough on his plate, he's also the co-CEO of Sovereign Capital. So I thought, let's go ahead and dive in. John, what started your journey in terms of thinking about money differently, and maybe a little more intentionally than the average person who's in the middle of the rat race trying to make it? Yeah, so, Stefan, when I was growing up, money challenges were different. When I was born, my dad was actually a rodeo cowboy. We lived in central Florida, in a single-wide trailer home. So money was really about getting enough so that you could make sure you were stable and that you had good education opportunities. And then, as I embarked on my career, I've spent most of it as an investor with big investment firms; Sovereign is one that I joined smaller, to help grow. And I began to be surrounded by people who weren't struggling to make ends meet; they were actually dealing with the problems that can sometimes arise by having too much. And you start to see what happens when money not only becomes your scoreboard, which it is, for an investor; I do private equity and venture capital, so I'm literally measured by how much money I can make for others every day. But you start to encounter people who have more than they ever dreamed of, and yet you notice their lives aren't always happy. When I was growing up, I thought the solution to a lot of life's problems was money. I was around a lot of people with money and realized, it certainly does solve some problems; when you don't have enough and you can't afford health care, or a house over your head, it certainly is a big problem. But at some point you get enough where your needs are met, and the challenge really becomes how to connect your financial life with what I think of as human flourishing, which is a good life comprehensively. And I just started to notice that as many people allowed their lives to go off track because of money as those whose problems money really addressed. So I started thinking deeply: what is it that can connect this topic of purpose and human flourishing, about which I've thought quite a lot, with a person's financial life? And how can a person dealing with an excess of money actually try and use that as a means to achieving the good life, rather than having it lead them further away from it?
Raising kids who have more than they need
And I bet being a dad also might have served as a catalyst for that. I know there's a parent reliving, in a different lens, things that you learn younger in your life, that sometimes can cause you to wonder, hey, how do I want to do this? Yeah, I've got four kids between five and 13, and their challenges as kids will be different than mine. Like I mentioned, we didn't have enough, that kind of topic, when I was a kid. And now I'm noticing, with their friends, their peer groups, etc., they have more than they need. And so my wife and I started thinking about how do we make sure the kids don't go off track because they have more than they need, and that we can teach them to anchor themselves in a deeper vision of human flourishing that's not connected to their financial lives, before they get older.
Keeping the flame of hustle lit
John, let's talk about that a little bit. One of the things, I also didn't grow up with a lot, and from that was born a natural sense of hustle. You want something, you go, go, go, make it happen. And I look at my own life and feel like that has been an essential ingredient to success, for the simple reason that things aren't just handed to you, at least not outside of the house, out there in the so-called real world, as we like to say to the kids. So for kids like mine, who grow up in a house where all their needs are met, what is your perspective on how we as parents still make sure the flame of hustle is lit and still there? Because outside of our homes, it's a competitive world, whether it's domestically or even internationally, you've got to hustle. Yeah, Stefan, it's a great question we grapple with all the time. Some of it is good, that they don't feel quite as much pressure as we might have growing up. We always want our kids to have a good education, good health care, to be well fed, that's good. But it's very difficult, as a parent, to stand by and not alleviate all the adversity in life. I'm a big believer that adversity, and having to overcome struggle and navigate problems yourself, is the way in which you prepare for the real world, that you do have to develop a sense of hunger to have a successful professional career. And the challenge with having too much, especially for parents, we're uniquely tempted, I think, because we know what it meant to have to struggle through stuff, so we want better for our kids. But sometimes, in trying to make it better for our kids, we handicap them long-term. I was with a family the other day, for example, that's now in the fifth generation of family wealth, and it struck me that not a single member of that generation was full-time employed, because they had just begun to live off this. And it wasn't like their lives were better as a result. People need meaningful pursuits for their time, they need a sense of purpose, they need a sense of accomplishment and of competitiveness. So we grapple with this, both financial and non-financial. One of the things my wife and I talk about is allowing the kids to navigate challenges on their own. We're not quite free-range parents in the way that my parents were, where I'd get kicked out of the house at seven, eight on a Saturday, and I'd see them that night when it got dark, like, hey, be home when the streetlights go on. That's right. We're very intentional with them. Like, we're not going to solve every interpersonal problem you have at school. We are going to let you go unsupervised sometimes and deal with your own problems, and we're not going to help through it. When you have a challenge with a teacher, we're going to ask you to try and navigate that first, unless it gets to a point where it's legitimate for us to step in. And financially, we've tried to structure their financial lives where we're setting the right principles. We term it apprenticeship for kids, because it really is not just telling kids what to do, but helping lead them through what to do. So they each have a ledger, where they keep their earnings, their savings, their investments, their giving money, and their spending. We tell them we'll provide your basic needs, but we're also not going to buy stuff for status. That's a big rule in our house; we never buy something just because someone else has it, we buy it if we need it. And so they know they're not always going to have the nicest shoes, they're not going to have the nicest clothes. And in fact, if they ask for that Yeti bottle or whatever, because somebody else has it or it's popular at school, they're definitely never getting it, because we don't want to spend money just for status competition. And so we hope they're learning the right principles, where their discretionary spending, they do have a ledger, they can spend out of it, and we try and counsel them through those purchases, but at some point that money's gone if they're not responsible with it. And we have some incentives for them to save and invest, and we make them do chores in order to earn into that, at age-appropriate levels. My five-year-old is not hustling quite as hard; he's hustling us sometimes, but he's not hustling in the world quite as much. And the 13-year-old's ready for a lot more responsibility, and a lot more independence. So we are grappling every day to find ways to empower them for independence incrementally, each year as they get older, and to actually expose them to adversity they have to overcome.
Letting kids learn to drive money
There are two additional fun things to throw into the mix there. One is: sometimes a kid will say, hey, I want to buy this, whatever that is, and it might be something that is either outside your budget, or just clearly ridiculous. And I think it's worth thinking about, as a parent, instead of saying no, you say, well, that's not in my budget, but if you want to buy it, and you want to find a way to earn it out of the right bucket, so not just liquidate your college savings on your ledger that we're helping you manage, but if you want to buy it, you can. And, well, why don't I have the money? Okay, well, you need to figure it out; let's talk about what you need to do to earn that money. And that can lead to some really great conversations. For example, if a kid asks for something truly outrageously expensive, I think that's a great opportunity to sit down and help them understand how much work it takes. And then, separately, sometimes if they come to me and say, hey, I want to do something, and it is important, just like we let our kids drive our cars and they learn on that, they've got to learn how to drive money. And the only way they're going to do that is if they're getting some, hopefully not too much starting out, but getting some, to learn how to manage. And just creating that intentional, open conversation that you're doing is awesome.
Money is a means, not an end
Certainly, back to adults for a second, and I want to touch on something you mentioned earlier about having too much. But I want to first start with the positive, which is: there are truly, unquestionably, some beautiful things that money can do, that once you have some, you're like, oh, this is great. I think that makes a great contrast for the second part of the conversation. But where do you see, can you speak to some specific examples of where you see money being spent in a beautiful way, really intentional, getting such a high ROI from a life standpoint? Talk to me about some examples you've seen where people have really done a phenomenal job at using their wealth in solving what money can solve. Yeah, absolutely. And one important thing about this book is, I am definitively not anti-money. I'm a red-meat-eating capitalist, given the profession that I'm in. But I think the important mindset to adopt is: money is a means, not an end, to human flourishing. Money is a tool, not a totem. And if you get that order wrong, if money becomes a focus and end in itself, we go astray. It's just a tool to try and create flourishing everywhere that it touches, whether that be earning, spending, giving, investing, or saving. And I walk through in the book each of those categories and how I think you can connect the use of money to true human flourishing. One example I use in the book, just to give one, is a business partner of mine named Casey, a former NFL player, who started a mortgage company that became wildly successful. And right at the beginning of building that, he had a financial advisor that he leaned into, at a firm he ultimately ended up buying, who encouraged him and his wife to do what they called setting a financial finish line, which was basically saying, this is the lifestyle that we think would be adequate for our family, and after that lifestyle and the ability to sustain it, we're not going to keep any of the money for ourselves. And so he's still going out and building businesses, but the profits of those businesses, he became so wildly successful, I think he hit his finish line in like four or five years, but instead of retiring, which is a concept I don't believe in, he kept building those businesses. But now he just uses those for the benefit of others. So his businesses are very values-oriented. He's earning with purpose, in the sense that he's trying to cultivate cultures within those businesses, that now have five or 6,000 employees in them, that help those employees flourish, that help clients flourish. And then the profits of those businesses he actually directly contributes into a foundation; ultimately the companies will be owned by that. And so he has a foundation that builds schools in the United States, charter schools, public charter schools, as well as churches, and help centers in Latin America and other parts of the world. And so he sees the benefit of this business growing all the time. And he lives a good life, his family lives a good life, they're not paupers by any stretch of the imagination, but now he's even more motivated to build these flourishing cultures. Every time they're profitable, he gets to stand up a new charter school for 500 kids and see those lives change. He gets to install a help center in Guatemala somewhere, where you can see people get medical care. And so he's actually more oriented toward achieving business success now, because it's about more than him. It's about more than money, a total on a spreadsheet somewhere. It's really about changing the lives of an increasing number of people, whether those be employees, clients, or those that he supports through the foundation. And that's kind of a cool orientation, where he's a capitalist, he's grown a business, he's a very good businessperson, but the purposes of that business have gone beyond his own personal enrichment, if that makes sense.
Being on mission in spending, business, and investing
That's amazing. And what's really fun about that, it's one of the few examples I think I've ever heard where there's the oft-quoted, what's your “f-you” number, and it's almost the inverse of that, where it's like, hey, I know my number, but that's when I get to start being 100% invested in my mission. And that's amazing. It's interesting, you can talk to clients and to people about the impact of mission and charity and philanthropy, and I think you get a lot of people that intuitively nod their head and go, yeah, that's good. But I think it's only once people actually make a difference, and see the impact of what they're doing, that they get a taste for how good it feels to help other people. And I don't know that there are many business owners out there who have ever, in their life, if you took all the most successful CEOs, business owners, founders out there, the top 100, and said, how many of those have ever, once in their career, spent a year maximizing their business superpowers for the benefit of somebody else, other than their own P&L, I dare say it's close to zero. Well, and what's liberating about that is it's not just generosity. I think philanthropy plays a huge role, and I think everyone should have habits of generosity, which we can talk about. But you can use that capital to be on mission in your spending, in the way in which you craft your companies or your work, in your investment portfolio. In your spending, we talk a lot about experiences, not stuff, how do you create meaningful experiences that help other people grow, including your own family, rather than just spending on stuff that's going to fade away? In your business, like I said, you can build companies that have great cultures that change people's lives every bit as much, if not more, than philanthropy, whether those are the people you serve or the people within the company. And the stories that come out of those. We own a bunch of companies through private equity, and we get stories all the time of how the company helped someone navigate a medical crisis. We even had an employee of one of our companies lose a young child recently, tragically, and the people within that company rallied around them; the company helped to pay for funeral expenses and walked through it with them. And it was life-changing for them. And then, of course, philanthropy, and even investing, can be a part of that. We've got a small media portfolio with a lot of investors who are just interested in the impact of positive representations in media, and they know it's a bit riskier and more financially tenuous than what they're doing, but they're using investment dollars to grow something culturally impactful. So I would remind people, generosity is essential, I think, to financial flourishing, but you can actually use your capital for good in all of those different areas. And a businessperson should feel liberated by that, because it lets them be on mission at work, in their investment portfolio, in their generosity, everywhere.
Capitalism you don't have to apologize for
Well, it lets you embrace capitalism in its best form. I think there's almost a pressure to apologize, sometimes, for wanting to be successful in business. What I'm hearing you say is, if you align your mission, then they can both coexist in harmony, and I 100% subscribe to that. Businesses exist because they meet a need. There are very few businesses that aren't doing, being a drug dealer is probably pretty tenuous, but just about every other business in the world meets a need for someone, whether you're running a grocery store, a gas station, or you have a mortgage company. You're doing something positive, and people need to reframe the way they think about that. The only difference is regulation, but they're both sort of anxiety, whether your headquarters are in downtown LA or Switzerland.
The problem of having too much
Switching gears. So there is a thing called having too much. And the funny thing is that a lot of people who are sprinting toward that exit, the first-time CEO, owner, they get a big payout, they sell their business, so they've got a bunch of money in the bank, and there was part of them that probably thought that's going to solve all their problems. They wake up a year after the acquisition, they've got a bunch of money in the bank, what's not perfect? What do you see out there that happens that causes people to go, wow, I never expected this? Yeah. There are tons of cautionary tales out there, partially because human desire is insatiable. And so, even though we think the money will solve our problem, it's never enough if we're focused on money. There are great surveys that show, if you make $35,000 a year, you think 50 is enough; if you make 250, you think 350 is enough. And I can tell you, I've met billionaires who thought a billion was enough, and then they got there and they thought, oh, maybe two or three billion would be enough. It's insatiable human desire. And there are a ton of cautionary statistics out there. You look at lottery winners, for example, who have this flood of wealth coming in, as you're describing; they have suicide rates at multiples of the general population, they go bankrupt at multiples of the general population, they have divorce rates at multiples of the general population. The same with professional athletes; I think the average development player goes bankrupt at 14 times the rate of the average other person. And so this flood of money, without the right habits, mindsets, and values to direct its use, can actually be incredibly destructive. And as I mentioned, I work with a lot of wealthy families, and you particularly see this in first-generation wealth, where it hurts marriages, it gets people obsessed with status, they get obsessed with claiming more and more money because they never feel full. And then, with their kids and their families, you see it probably amplified, where, as we talked about earlier, you see kids who never develop a mission in life, they never develop a sense of purpose, which is so essential to human flourishing, they never develop character, because they haven't had to fight through adversity. So they become unbounded, or amoral, and they don't really know how to direct their lives in a positive way. And you see, even right now, what's interesting is, incidences of drug addiction are basically as high amongst ultra-high-net-worth people, their kids, as they are amongst the poorest people. This excess of money can actually lead you down dangerous paths. And so I think, when you think of money as the solution, what you really need to think is: money is good at alleviating pain, it's not good at achieving flourishing. And so, unless you have a conception of the good life to anchor it, you're not going to use that money in the right ways to anchor purpose.
Money solves external pain, not internal
I might also add, it's good at solving external pain, it's not really good at solving internal pain. And if somebody's being honest with you, most people will tell you they've got some kind of baggage, some kind of hurt, some kind of worries or fears or anxiety, today more than ever. And that's the piece that money can't buy. And ironically, I see, you probably see the same, people that have a lot of money now have a new problem, and that new problem is: don't lose it, don't screw it up. Before, you're trying to get it, it's like, how do you lose, I have to make this work. But then, what's the lifestyle creep? They never feel like they're more than a little bit away. You suddenly get more money than you thought, then you start spending more, and so you're on the same financial treadmill you were before, if you don't cap your lifestyle and be thoughtful about it. Yeah. And you're sitting on 50 million, 100 million, and all of a sudden you read the headlines differently. You're like, man, I don't want to lose this. What happens if this, what happens if that? And then, of course, what happens is everybody's knocking on your door going, hey, invest in my new startup, invest in this. And at first it's exciting, put a little here, put a little there. Next thing you know, you've got 30 different private-equity investments. And statistically, we know that a good chunk of them aren't going to work out. And then all those people, ironically, sometimes under a fiduciary obligation, are required to update you and share with you all these sad stories about how it's not working, and it's somebody else's fault, and yada, yada, yada. It's like a full-time job, and it's not fun. And I think it's a lack of intention, or even sometimes chasing higher returns, but why? You don't need to. Why are you doing that? And on pressure, I had a friend who sold his company about a year and a half ago for about $100 million. He had worked his whole life to do this. He's a wonderful guy. And suddenly the number showed up in the bank account, and he kind of panicked a little bit and was like, what do I do with this? I worked my whole life for this. I don't know where to deploy it, or how to deploy it, because I don't want to waste it. And so, talk to the average person about that, and that's certainly a champagne problem, but it is easy to underestimate the anxiety that will hit once you've achieved that goal and you move into defense mode, and are certain to think about protecting it.
Anchoring in the permanent things
You know, I've long said that true wealth lives at the intersection of health, wealth, and purpose. And John, you've got some really great stories that you've shared, and I'm eager to go out and get your book and read a bunch more, and stay in touch. I really appreciate all the work that you're doing out there. One of the things I most appreciate about what you're doing is helping people become proud of capitalism done right. It's not perfect, it depends on execution and implementation, and we're all human, so of course we're going to screw it up sometimes. But there aren't enough people out there talking, modeling, and explaining how we can embrace the best of who we are in America in the context of capitalism, and hold our head high and feel proud about it, not just when connecting with each other here internally, but frankly even when we're traveling around the world meeting with other countries and leaders in different parts of the globe, and feel good about who we are. So I appreciate the roadmap that you're helping lay out for people and the conversations that you're seeding. I think these are the kind of conversations that people need to have, and they need to have them before they exit, because at a personal level, it helps you to better define your own moral compass, your own money compass. But I think, when reading your book, people understand the impact you have on others is so big, even bigger than you might think, that as an owner or a steward of a significant amount of money today, you really have to figure out your purpose and what you stand for. Any closing thoughts, John? Yeah, I think you hit the nail on the head, Stefan. As I mentioned, I'm just a kid from a trailer park who did a lot better than he thought he would do. And that experience led me to write this book, as much for myself as for others: how do we anchor ourselves in the permanent, important things in life? You mentioned them, spiritual, mental, and physical health, meaning and purpose, character and virtue, deep and positive relationships, because those are the things that create a good life. And how do we make sure that the money we've accumulated, and what we're building, enables that in our lives and the lives of others, rather than makes it more difficult to accomplish? And it's so encouraging to me that you, and the audience you're with, are grappling with that, because I think the talents of you and people like you are enormously positive for the world, and we're all working to just figure out how to use that well, and to make our lives and other people's lives better. So thank you for the opportunity to speak into it. You bet. And just a reminder, everybody, if you want to get the book, it's called Good Money: Six Steps to Building a Financial Life with Purpose, published by a little, relatively unknown university in Boston, Harvard Business Review. Check it out. John, great having you on. Look forward to staying in touch. Thanks so much. All right.
Transcript edited for readability from the video. Machine-transcribed; may contain minor errors.
Key Takeaways
A written companion to the episode, written for those who prefer to read.
John Coleman was born in central Florida, in a single wide trailer home, to a father who rode in rodeos. Money in that house meant one thing: enough. Enough for stability, enough for a decent education, enough to keep the floor from giving way. He grew up believing, as most people raised that way do, that money was the answer to most of life's problems. Then he spent a career getting close enough to money to watch what it actually does, and the belief did not survive the evidence.
Coleman is co-CEO of Sovereign's Capital, where he invests across private equity and venture capital, and he has spent most of his working life as an investor at large investment firms. He is also the author of Good Money: Six Steps to Building a Financial Life with Purpose, published by Harvard Business Review Press, and of The HBR Guide to Crafting Your Purpose. It is an unusual pairing. By his own description he is measured every single day on how much money he can make for other people. He is also one of the very few people in that seat who has thought carefully, and in public, about what the money is ultimately for.
The shift came from proximity. Once he was surrounded by people who were not struggling to make ends meet, he began meeting people with more than they had ever dreamed of whose lives were plainly not happy. Over time he arrived at the observation that organizes everything else he has to say: as many people allow their lives to go off track because of money as have their problems genuinely solved by it.
Coleman is careful about what he is not. He is not anti-money. Given his profession, he describes himself as a red meat eating capitalist. The distinction he draws is one of order, not of degree. Money is a means, not an end. It is a tool, not a totem. Get the sequence wrong, let money become an end in itself, and the tool quietly starts pointing you somewhere you never intended to go.
Get the sequence right and something more interesting happens. Money stops being confined to one line item and becomes usable across the whole of a life: in earning, in spending, in giving, in investing, in saving. Coleman's argument is that each of those five categories can be connected to human flourishing, and that a business person should feel liberated rather than constrained by that idea. It means you can be on mission at work, on mission in the portfolio, and on mission in what you give away, all at once.
The financial finish line
His clearest illustration is a business partner named Casey, a former NFL player who started a mortgage company that became wildly successful. Early in the building of it, Casey leaned on a financial advisor at a firm he would eventually buy, and that advisor encouraged him and his wife to do something most people never do. They set a financial finish line. They named the lifestyle they believed would be adequate for their family, and the capital required to sustain it, and they decided that everything beyond that line would not be kept.
He crossed the line in four or five years. What he did next is the part worth studying. He did not retire, a concept Coleman does not believe in. He kept building. The companies now employ five or six thousand people and are run with an explicit orientation toward the flourishing of those employees and their clients. The profits go directly into a foundation, which will ultimately own the companies outright. That foundation builds public charter schools in the United States and churches and help centers in Latin America and elsewhere. Every time the businesses are profitable, another school opens for five hundred children, or another medical help center opens in Guatemala.
The effect on his motivation was the opposite of what most people would predict. He is more oriented toward business success now, not less, because the success is no longer about him. Whitwell caught the inversion immediately. The culture has a well-worn phrase for the number that sets you free, and it is almost always framed as an exit from work. Casey's version runs the other way. The number is not where the work stops. It is where the work becomes fully invested in the mission.
Coleman would not want the story reduced to philanthropy. Generosity, he says, is essential to financial flourishing, and everyone should build habits of it. But capital can be put on mission in far more places than the giving account. It can go into experiences rather than stuff, the kind that help people grow, including inside your own family. It can go into the culture of a company. Sovereign's owns businesses through private equity, and the stories that come back are not abstractions: a company that helped an employee navigate a medical crisis, another that rallied around an employee who lost a young child and helped carry the funeral costs and walked with him through it. It can even go into the portfolio itself. Coleman describes a small media allocation whose investors know the risk is higher and the financial case more tenuous, and who are there because they want to grow something culturally worthwhile.
Whitwell's response was that this is capitalism in its best form. There is a quiet pressure in some quarters to apologize for wanting to succeed in business, and the answer to it is not defensiveness but alignment. Coleman put the point plainly. Businesses exist because they meet a need. Almost every business in the world, from a grocery store to a gas station to a mortgage company, is doing something a person actually required.
What money is good at
Then the conversation turned to the other side, and Coleman was equally direct. Human desire is insatiable. Surveys make the point with almost comic consistency: a person earning USD $35,000 believes USD $50,000 would be enough, and a person earning USD $250,000 believes USD $350,000 would do it. Coleman has met billionaires who were certain USD $1 billion was the number, arrived, and revised it upward.
The cautionary data is harsher still. Lottery winners, who experience exactly the flood of sudden wealth that a first-time seller experiences at closing, show suicide rates, bankruptcy rates, and divorce rates at multiples of the general population. Professional athletes follow a similar pattern; Coleman cites the average NFL player going bankrupt at fourteen times the rate of the average person. Among families with substantial first-generation wealth he sees marriages strained, an obsession with status, and a hunger for more that never fills. Among their children he sees something more troubling: young people who never develop a mission, never develop a sense of purpose, and never develop character, because character is built by fighting through adversity and adversity was removed. He notes that incidences of drug addiction among the children of ultra high net worth families run about as high as among the poorest.
Which produces the sentence that anchors the chapter. Money is good at alleviating pain. It is not good at achieving flourishing. Unless you hold a real conception of the good life to anchor it, the money will not find its way to the right uses on its own.
Whitwell added a refinement worth keeping. Money is good at alleviating external pain. Almost everyone, if they are honest, is carrying some form of baggage, fear, or anxiety, and that is precisely the category money cannot reach.
The problem after the exit
There is also a specific and under-discussed anxiety that arrives with success, and both men have watched it up close. The person striving toward the exit has one problem: make this work. The person on the other side of it has a new one: do not lose it, do not get this wrong. Whitwell described a friend who sold his company about eighteen months ago for roughly USD $100,000,000, a man who had worked his entire life for that outcome. The number landed in the account and he panicked. He did not know where to deploy it, or how, because he did not want to waste it.
Coleman's warning about lifestyle creep belongs here. Wealth arrives, spending rises to meet it, and the person finds themselves back on the same treadmill they thought they had stepped off, only at a higher altitude and with more to lose. Then the door starts knocking. Every founder wants a check. The first few placements feel exhilarating, and then there are thirty private positions, a statistically inevitable share of which will not work, and a stream of obligatory updates explaining why. It is not a full-time job. It is not enjoyable. And it usually traces back to either a lack of intention or a reach for returns that were never actually needed.
Raising children who have enough
Coleman was recently with a family now in its fifth generation of wealth. What struck him was not the money. It was that not one member of that generation was employed full time, and that their lives did not appear to be better for it. People need meaningful pursuits, a sense of purpose, a sense of accomplishment, and something to compete against.
He and his wife have four children between five and thirteen, and they are working the problem in real time. The temptation, he says, falls hardest on parents who remember the struggle, because knowing what it cost makes you want to spare your children the same. But standing between a child and every difficulty is how you handicap them for the world they will eventually have to enter. So the household is deliberate about leaving some friction in place. They do not solve every interpersonal problem at school. They let the children go unsupervised and work through things. When there is a conflict with a teacher, the child is asked to navigate it first, unless it escalates to something a parent legitimately should handle.
The financial side they call apprenticeship, which is a precise word for it: not telling children what to do with money but walking them through it. Each child keeps a ledger with five columns, earnings, savings, investments, giving, and spending. Basic needs are provided. Status purchases are not. It is a stated rule of the house that they never buy something simply because someone else has it, which means the children know they will not always have the best shoes or the popular bottle, and that asking on those grounds is the surest way to a no. Discretionary money is theirs to spend from the ledger, with counsel, and if they spend it badly it is gone. There are incentives to save and invest, and age-appropriate chores that feed the ledger.
On the perennial argument about paying children for chores, they have landed in between. Some work is simply the price of being alive in a family: your own laundry, your own plate, your own room. Nobody gets paid for that. Separately there is a chore wall with real responsibilities attached, the dogs, the trash, that earns a modest allowance. Whitwell's addition was a reframe he has found useful with his own children. When a child asks for something outside the budget, the answer is not no. It is that it is not in my budget, and if you want it, let us talk about what it would take for you to earn it. Sometimes the child does the arithmetic and decides they did not want it that badly, which is a far more durable lesson than a parental refusal. Sometimes they decide they do want it that badly, and they go and get it, which is better still. As Whitwell put it, we let our children learn to drive our cars; they have to learn to drive money too, and they can only do that with some of it in their hands.
The permanent things
What Whitwell most appreciates about Coleman's work is that it helps people become proud of capitalism done right. Not perfect capitalism, which does not exist, because execution is human and humans get it wrong. But a version worth defending, modeled and explained clearly enough that a founder can hold their head up about it at home and abroad. And it is a conversation best had before the exit, not after, because it is what allows a person to define their own money compass while the decisions are still ahead of them.
Coleman's closing was disarming for a man in his position. He described himself as just a kid from a trailer park who did a lot better than he expected to, and said that experience is what drove him to write the book as much for himself as for anyone else. The question he keeps returning to is how a person anchors themselves in the permanent and important things: spiritual, mental, and physical health; meaning and purpose; character and virtue; deep and positive relationships. Those are the things that make a life good.
The money question, then, is not how much. It is whether what you have accumulated, and what you are still building, makes those things more possible or less. That is the whole test. Everything else is scoreboard.