Between January and July 2025 there were 262 sales at $10m or above across Miami-Dade, Broward and Palm Beach counties, according to MIAMI REALTORS. At that level the paperwork stops distinguishing anyone. Terms converge, counsel is drawn from the same short list of firms, and two competing proposals can arrive at a family’s desk looking close to identical on every measurable axis.
Tommy Shields is Head of Investor Relations at Onyx Reserve, a private investment firm operating in South Florida, which puts him on the side of that decision nobody documents. The exchange below was edited for length. The questions were written to press rather than to invite, because the flattering version of this subject has been published many times and is not much use to anyone.
Q. The premise of the question is doing a lot of work here. When two proposals genuinely are comparable, is it not simply true that the choice comes down to who the family liked more, which is another way of saying the decision was not rigorous at all?
“That is the fair version of the criticism and it deserves a straight answer rather than a defence of the industry. Liking someone is not a criterion. But watching how a person behaves across four meetings is a criterion, because it is the only evidence available about how they will behave in the year the plan does not work. Documents describe intentions under good conditions. Nobody writes down what they will do when a projection slips by eighteen months, and nobody can, because the honest answer depends on temperament. So the family is not choosing on warmth. It is choosing on the only sample of conduct it has been given.”
Q. BlackRock surveyed 175 single family offices holding more than $320bn between March and May 2025 and found 32% intending to raise private credit allocations and 30% infrastructure. Those are portfolio decisions, made by committees, with models behind them. What exactly is a meeting supposed to add to that?
“Nothing about the allocation. The committee is right to decide that on its own numbers and a relationship should not move it by a basis point. What a meeting settles is a separate question, which is who the family wants standing next to that decision for the decade it takes to play out. Someone can be entirely correct about private credit and impossible to reach in March. Those are independent variables and only one of them is in the model. The mistake is treating the meeting as a second opinion on the allocation. It is not. It is due diligence on the person, and it is the only place that diligence can be done.”
Q. What does a person actually notice in a room that never survives into a document?
“Who the visitor talks to when the principal leaves to take a call. Whether the answer to a question the person did not expect is shorter or longer than their prepared answers, because both tell you something and the long one usually tells you more. Whether they correct a colleague in front of a client, and how. Whether the junior person who did the actual work is in the room at all, and whether anyone says so. None of that goes in a memo, partly because it would read as gossip and partly because it cannot be evidenced. It still determines the outcome about as often as anything that does get written down, and pretending otherwise is a courtesy nobody in the room actually extends.”
Q. Commercial Observer reported that South Florida transactions above $10m and above $30m both doubled year on year in the first quarter of 2026, while Douglas Elliman and Miller Samuel recorded Miami Beach luxury single-family homes taking 251 days to sell in the fourth quarter of 2025 with inventory in that segment up 32.7%. Parts of the market reward decisiveness and parts of it punish nothing but impatience. Does the slow relationship not simply lose to the fast one where it counts?
“Frequently, yes, and anyone who says otherwise has not been outbid. Speed wins individual transactions. It does not survive a bad year, and every ten-year period contains at least one. What the fast version cannot do is produce the phone call where somebody says the thing that is going wrong before it is fully going wrong. That call only happens between people who have already had a hundred boring conversations. So the trade is real and it should be named honestly rather than argued away. A patient approach loses deals it would like to have won.”
Q. UBS surveyed 307 family offices holding $627.4bn between January and March 2026 and found only 27% run structured next-generation education programmes, with just 35% holding a defined succession plan. The audience for this conversation is routinely described as sophisticated. Is that description accurate?
“For a minority of it. Sophistication in this segment is wildly uneven and the polite convention is to pretend otherwise, which does the less-prepared families no favours at all. There are offices that run a genuine investment committee with a written policy and a documented process for disagreement. There are others where a very successful person makes decisions alone, quickly, on instinct that worked in the business that generated the money and may not transfer. Both are called family offices and they need completely different conversations. Flattering the second group as though it were the first is how people get hurt.”
Q. Deloitte counted 8,030 single family offices worldwide in 2024 and projects 10,720 by 2030, with assets rising from $3.1trn to a projected $5.4trn. A larger cohort means more first-generation wealth entering. Does money that was earned ask different questions from money that was inherited?
“Completely different questions, and the difference shows up in the first twenty minutes. Someone who built the business asks about the operator, because they ran an operation and know that is where outcomes are decided. They want to know who is actually doing the work and what happens when that person leaves. Someone who inherited asks about the structure, because they have watched a structure hold or fail to hold across a generation and they know the founder will not always be there. Neither instinct is better. But answering the structural question with an operator’s answer, or the reverse, reads as evasion even when it is just a mismatch, and it costs more relationships than any disagreement about strategy ever has.”
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