Somewhere this week, a family handed its money to someone. Maybe a sister in Houston wired three years of savings to an uncle back home who promised to handle the purchase of a plot. Maybe a founder...
Somewhere this week, a family handed its money to someone. Maybe a sister in Houston wired three years of savings to an uncle back home who promised to handle the purchase of a plot. Maybe a founder gave the shop's best-ever quarter to a friend who knows shares. Maybe it was the treasurer of a SACCO, a member-owned savings cooperative, or a broker app promising twelve percent, or a fellow church member with a forex opportunity that only needs a little faith. The handover always arrives with the same feeling: relief. Finally, someone who understands this is dealing with it.
The relief is exactly the problem. The moment money changes hands is the last moment your questions carry any power. Every question you fail to ask before the handover, the money will answer for you afterward, and money answers slowly, expensively, and without sympathy.
Gregory Curtis spent more than thirty years watching wealthy American families live through that moment. He founded Greycourt & Co., a Pittsburgh firm that advises rich families, after years spent stewarding Mellon family money, and in 2012 he distilled what he had seen into a book called The Stewardship of Wealth: Successful Private Wealth Management for Investors and Their Advisors. Let us be honest about that book before we mine it. It was written for families who have private banks, lawyers on retainer, and a shortlist of advisory firms competing for their business. It is also, by now, a book of its era: its regulatory references, its industry vocabulary, and its crisis stories are American and dated. Most of its machinery simply does not exist for the family we write for, the family managing its own money across a kitchen table or a WhatsApp group, sometimes across an ocean.
But buried in Curtis's chapter on choosing an advisor is a discipline that costs nothing, requires no industry, and travels anywhere: two questions a family should answer before trusting anyone with its money. Notice the grammar. These are not questions to ask the person you might hire. They are questions the family asks itself.
Curtis teaches them through a family he presents as illustrative, the Schulbergs. In 2005 the Schulbergs held $23 million in liquid assets, a large sum that was nonetheless dwarfed by the family's real wealth: a regional cable television business already worth an estimated $100 million. Before choosing anyone to manage the liquid money, the family asked itself two things: "What business are we in as a family?" and "How do we feel about conflicts of interest?" Their first answer was clear. They were in the business of running a business, so the liquid money was a sideshow, and they hired an all-in-one advisor to take the whole problem off their hands while they built the company.
Seven years later they sold the company for nearly $300 million, and here the story turns. The family asked the same two questions again, and the answers had changed. They were no longer in the business of running a business; managing money was now, in Curtis's phrase, "the entire ball game." And they discovered the hidden price of the convenience they had bought: in almost eight years, the family had learned nothing about how its own money was managed. Curtis's verdict is quietly brutal: "the family had become an intellectual ward of their advisor." They fired the comfortable firm and hired one that would make them participate in every decision, precisely because they had so much to learn.
"What business are we in as a family?" sounds like a riddle until you watch it work. It is not asking what the family does for a living. It is asking where the family's real risk and real attention must live this year, because that answer decides what kind of help you need and, more importantly, what you can never outsource.
A family whose wealth is one busy shop and next term's school fees is in the business of running a business. Its money help should be boring, cheap, and safe, because the family's attention belongs on the shop. A family that has just sold land, or received a payout, or buried the founder and consolidated the accounts, has changed businesses without noticing. It is now in the business of managing money, and the standard has changed: help that merely takes the problem away is no longer good enough, because the family itself must now understand what is happening to its wealth.
The diaspora household deserves its own sentence, because it changes businesses most often and notices least. Sending support home is one business; building assets at a distance is another. The month a sister stops sending money for consumption and starts sending money for a plot, a matatu, or a share of a cousin's venture, she has entered the second business, and it demands different help, different reporting, and far more of her own understanding than the first ever did.
That is the deeper point of the Schulberg story, and Curtis says it plainly elsewhere in the book: a family does not need to produce professional investors, but it must gain enough understanding "to enable the family to be an astute consumer of investment services." Convenience is a real product with a hidden price. Every year someone else does your thinking, your family learns nothing, and that is a fine bargain while money is the sideshow and a fatal one the day money becomes the ball game.
The Schulbergs' second question, "How do we feel about conflicts of interest?", sounds abstract until you hear what Curtis thinks of his own industry. His chapter on the 2007 to 2009 financial crisis lays down one of the harshest verdicts a working insider has ever published about his profession: "The root cause of the crisis was the gradual but ultimately complete collapse of ethical behavior across the financial industry." What he means specifically, he says, is "the disappearance of any sense of fiduciary responsibility to the ultimate client": the firms stopped treating the customer as the reason the business exists. He even quotes the industry's own bleak joke about how it makes money: "No conflict, no interest."
Two honesty notes belong here. First, the crisis he is dissecting is a specifically American story from 2008, full of mortgage products and rescue programs that mean nothing to most readers and are, fourteen years after the book, history rather than news. Take the transferable point and leave the machinery: when the person advising you eats from the transaction rather than from your outcome, the advice bends toward the transaction. Second, keep Curtis's own position in view. He is an insider indicting his industry, and his prescription, at the end of the indictment, is to hire a better version of his own kind of firm. His diagnosis is more trustworthy than his prescription, and it is the diagnosis we are taking.
Now translate the question out of Wall Street, because conflicts of interest do not require an investment bank. The land broker is paid by the seller, so his enthusiasm is not information. The cousin recommending a plot has a part-interest in the plot. The SACCO official voting on loans has a loan application of his own in the drawer. The "opportunity" moving through the church or the clan network arrives pre-trusted, vouched for by people who have verified nothing, because in tight communities vouching substitutes for verification. And the relative abroad discovers, too late, that the person holding the building money and the person deciding how it is spent were the same person all along.
The question is never "is this a good person?" Good people follow their incentives too; they simply feel worse about it afterward. The question is: on the day my interest and this person's interest point in different directions, which way does their income point? If you cannot answer that, you have not finished your diligence, whatever their reputation, their credentials, or their surname.
Curtis's actual selection process is a museum piece for our purposes, and we should say so rather than pretend. His families narrow the field to four or five firms, send formal request-for-proposal documents, hold interview days, and negotiate custody arrangements with banks. If you do not have a private banking industry competing for your family's business, you will never run that process, and imitating its paperwork would be theater. But look underneath the process at what it was for, and everything transfers. It forced the family to know its own needs before hearing any sales pitch. It compared more than one option. It separated the person who holds the money from the person who decides what happens to it. And it put everything in writing.
The household version fits in four habits. Ask, out loud and early, "How do you make money on me?"; anyone offended by the question has answered it. Never let one person both hold the money and direct it: money sits in a bank, a SACCO, or a mobile wallet in the family's name, and the trusted person instructs, with a record, rather than pockets. Start small and watch one full cycle before trusting a large sum; a person who handles one season's modest money honestly and reports on it without being chased has shown you more than any certificate can. And insist on paper, however humble: a statement, a receipt, a two-paragraph written agreement, because the person who resists writing things down is telling you which version of events they plan to rely on.
One more thing must be said gently, because it is the real obstacle in many of our families. Asking a relative how he is paid, or asking for a statement, can feel like an accusation, an insult to the trust the family runs on. Turn that around. The question is what protects the relationship. Money lost in silence takes the relationship down with it; there are families that have not shared a meal in twenty years over an unexplained plot. Money guarded by clear questions leaves the relationship standing whatever happens to the money. The families that stay close are not the ones who never asked. They are the ones who never had to wonder.
It would be easy to read all this as a case for trusting no one, and Curtis closes the door on that reading himself. His advisor chapter ends with a warning that cuts both ways: "A family without an advisor is like a ship without a rudder. But a family with a bad (incompetent, venal, conflicted) advisor is probably in even worse shape." Doing everything yourself is not safety; it is just a different unmanaged risk, the risk of your own blind spots compounding quietly for years. The goal is not zero trust. The goal is tested trust: help you chose on purpose, whose incentives you can state in one sentence, whose work you can see on paper, and whose performance you are competent to judge because you never stopped learning.
That last habit is where a tool earns its keep. The plainest version of this whole discipline lives in the LegacyPot Cash Log: every time money leaves the family's hands for someone else to manage, hold, or spend, it gets an entry, with the amount, the date, what was agreed, and one line on how that person earns from the arrangement. A year of those entries is a complete record of who the family trusts, on what terms, and how each trust performed, which is exactly the knowledge the Schulbergs paid eight years and a fortune in convenience to discover they lacked.
Before the next handover, however small, sit down as a family, or as a couple, or alone with a notebook if the money is yours to steward, and write two answers down. First: what business are we in as a family this year, in one sentence? Running a business? Managing what we have built? Building assets at a distance? The answer tells you what kind of help you need and what you must learn yourself. Second: how does the person we are about to trust get paid, and which way does their income point on the day our interests part ways? Ask them the question in person, in those words if you like. Then start smaller than you planned, put the agreement on paper, and watch one full cycle before you scale the trust.
And if family money is already in someone's hands, run the overdue test this week: ask for a statement. Not an interrogation, one written statement. The reaction is the report.
Curtis's families had lawyers to run this diligence for them. You have two questions and a log. Used every time, they are enough, and they are more than most families, at any level of wealth, ever bother to use.