By Kristen Oliveri
Editor’s Note: This is part one of a two-part series. Next, we’ll hear from TIGER 21 New York Chapter Head Michael Warszawski, who shares his perspective on many of these same themes around wealth, meaning, legacy and family dynamics.
For many founders, building wealth is only one chapter of the story. The harder question may be what they want that wealth, and the life behind it, to mean to the generations that come after.
Michael Sonnenfeldt has spent decades thinking about these questions from multiple perspectives. As Founder and Chairman of TIGER 21, he has built a global community where wealth creators and preservers can learn from one another.
In this conversation with Wealth Reimagined, Sonnenfeldt reflects on legacy beyond financial assets, the stories and values founders should be sharing with the next gen and why defining a family’s purpose can be just as important as preserving its wealth.
Q: One of the biggest questions founders wrestle with is whether to tell their children about the family’s wealth at all. Why is this conversation so emotionally complex for parents?
A: Two fears sit on top of each other and pull in opposite directions.
The first is that silence leaves a child unprepared for something that will reach them anyway, through a lawyer, a headline, or an overheard call. The second is that clarity removes the pressure that made the parent successful in the first place.
That second fear is the one people rarely say out loud, and it comes from experience. A large share of first-generation wealth creators grew up with real constraints. Some came from modest circumstances, some from difficult homes. The hunger that produced was part of the engine. A founder who has spent 30 years removing every obstacle from a child’s path can look at what they built and wonder whether they took the engine out with it.
Then there is identity. For an entrepreneur, the business and the money are bound up with the story of who they are. Sitting down with a child to talk about the wealth means talking about themselves, including the years they were absent, the risks they took with the family’s security, and the luck they will never fully be able to separate from the skill.
None of that discomfort is a reason to wait. Postponing the conversation is a decision too, and children read the silence.
Q: Is there ever a "right age" to introduce children to the realities of family wealth, or is it more about emotional maturity than a specific milestone?
A: There is no single age, and I would be skeptical of anyone who tells you there is. What I can tell you is where Members come out, and the split is consistent.
Roughly 70 percent want to wait until their children are close to 30 and have established careers of their own before detailing what they might inherit and when. Their reasoning is consistent: they want their children leading independent, productive lives, and they do not want knowledge of an inheritance to distract them or take them off course. The other 30 percent or so start much earlier, in the late teens or early twenties, on the view that stewardship is a skill and skills take years to build.
Both approaches are valid. Families are different, children within the same family are different, and the parent who knows the child is better placed than any framework.
What I would separate is the fact from the figure. Children in a wealthy household work out that they are wealthy long before anyone tells them. The realistic question is when to replace their guesswork with something accurate, and that is where maturity matters more than a birthday. The number can come later. The values and the expectations that go with it should arrive early enough to shape something.
Q: Many founders want their children to have a normal upbringing. How do families strike the balance between protecting childhood and preparing the next generation for future responsibility?
A: A TIGER 21 Member once put it to me in a way I have come back to ever since. He said he was not going to give his children anything, and he was willing to invest everything in them.
That distinction does a lot of work. Investing everything means paying for the education, backing the first business, funding the apprenticeship in an industry they care about, and being present. What comes with it is accountability. The money is attached to something the child is doing, and there is a conversation about how it went.
Normal is worth interrogating as a goal. A child flying private is not living a normal childhood, and pretending otherwise teaches them that the family is uncomfortable with its own circumstances. What is achievable is a childhood with structure: work, consequences, a summer job that is difficult, and the experience of wanting something and having to wait.
Preparation happens over a decade of small moments, where a child is given something to be responsible for and allowed to handle it badly, at a scale where handling it badly costs almost nothing. The first sum a child is trusted with should be small enough that losing it is a lesson rather than a loss.
Q: What are some of the biggest mistakes you see families make when they either wait too long—or share too much too early?
A: The most common pattern I hear about is silence that lasts so long it becomes its own message. A child who has never been told anything concludes one of two things, that the parents do not trust them, or that the situation is worse than it is. Neither is usually true, and both are hard to undo. One of the lessons in Think Bigger is simply not to keep your family in the dark, and it is there because so many Members arrived at it the hard way.
At the other end, timing gets blamed for something that is usually a problem of scaffolding. A figure delivered to a 22-year-old with no context about how it was made, what it is for, what happens if it is spent, or who else depends on it lands as a weight rather than as information.
The version I would watch for most closely is the family where the parents have had this conversation with their lawyers, their accountants, and their peers, and have never had it with the people it concerns. That happens more often than you would expect, and the discovery is usually accidental and always worse for it.
Whichever end a family errs toward, the correction is the same. Communication. Communication. Communication.
Q: Beyond discussing assets, what are the most important values parents should be passing on alongside financial wealth?
A: Financial capital is the easiest of the four to transfer and the least predictive of what happens next. The others are social capital, reputational capital, and intellectual capital. Families who are explicit about all four tend to hand on something more durable than a balance sheet, and a child who understands what the family stands for starts from a stronger position than a child who only knows what it owns.
Underneath those, stewardship. When children inherit great wealth, the first challenge is teaching them to be stewards of it. A steward understands that the capital came from somewhere, that it is going somewhere, and that their job in the middle is to hand it on in better condition. That framing takes the pressure off in a way people find surprising. The child is not being handed a score to beat.
Humility belongs in the list as well. I have watched brilliant people lose money because they assumed that being right about one industry made them right about all of them. That mistake is much cheaper to inherit as a caution than to learn firsthand.
And work, for practical reasons as much as moral ones. Purpose is the one thing the money cannot buy, and its absence is the most common source of unhappiness I encounter among people who have everything else.
Q: We've talked a lot on Wealth Reimagined about the idea that legacy is about much more than money. How can founders use these conversations to share the family's story, purpose, and vision?
A: An estimated $84 trillion will pass to younger generations over the next two decades. That is the largest transfer of capital in the history of the country. Who receives it is already largely settled. What they do with it, and whether anyone gave them a reason to do anything worthwhile with it, is still open.
Which is why I would begin with the story rather than the structure. Every family has one, and children almost never have the whole of it. They know their parent runs a company. They do not know about the year the payroll was covered on a personal credit card, or the partner who walked away, or the decision that could have gone the other way. Those stories carry more information about values than any set of documents, and they establish something important: this was earned, it was uncertain, and it could have failed.
From there the conversation opens naturally onto purpose. What was the money for? What does the family want to be known for in 50 years? What problems does it care about enough to put capital behind?
I have seen accumulation harden into a fortress mentality, where people who built something remarkable retreat behind walls out of fear of losing it. Involving children in questions of purpose is one of the better antidotes I know. Independence without interdependence is an illusion, and that lesson lands earlier when the family works it out together.
Q: If a founder has avoided this conversation for years because it feels uncomfortable, where should they begin? What's one first step that can make the discussion feel less intimidating?
A: Start small, and start with something other than the number.
The single most useful first step is a conversation about the family’s values, held with no figures in the room at all. What do we care about? What do we want to be known for? What would we want to be true about this family in three generations? That conversation is safe, it is genuinely interesting, and it costs nothing to have. It also does something quiet and useful: it establishes that money is a subject the family can discuss without the temperature rising.
The second step, when it comes, might be philanthropy. Give the children a modest pool of capital and a decision to make together about where it goes. They will have to research, disagree, and reach a conclusion. That is a rehearsal for every conversation the family will have later, at stakes where a mistake costs nothing.
Founders should also give themselves permission to do this badly the first time. Treat it as a habit rather than a performance. An awkward first attempt matters far less than whether there is a second one.
Almost no one I know regrets starting. A great many regret waiting.