Thursday, December 25, 2025

The Biggest Mistakes Billionaire Families Make With Wealth Transfer

If the rule stands that you shouldn’t discuss money at the dinner table, then there will likely be some awkward conversations happening over the next couple of decades.

In the next 25 years, an intergenerational wealth transfer of $74 trillion is expected, according to a June report by UBS. Among the ultrawealthy, this transfer is accelerating: By 2040, the world’s billionaires are expected to pass down $5.9 trillion to their children, UBS estimated in a December report, which focused on billionaires.

That amounts to the greatest wealth transfer in history — and plenty of familial expectations.

The billionaires surveyed by UBS have high aspirations for their children: 82% hope their kids “develop the skills and values to succeed independently,” and 61% hope their children are “happy/comfortable with managing the family’s wealth.”

Richard Orlando, the founder of Legacy Capitals, a consulting and advisory firm for wealthy families and family offices, aims to help that transfer, and the expectations that come with it, go as smoothly as possible. He works with clients to educate them and cement plans around succession, investing, giving, and — the big one — inheritance.

While more money can mean more complex problems — Legacy Capitals families are worth between $20 million and $3.5 billion — everyone can learn from a thoughtful approach to these topics, he said.

“Any family who’s more intentional about transferring values, educating, and preparing the next generation for stewardship, whether that’s $2 million going to the kids or $200 million,” sees better results, he told Business Insider.

He broke down three common mistakes families make when dealing with inheritance — and how to correct them.

1. Silence is not the solution

Many wealthy parents shy away from discussing money with their children, fearing it may lead to entitlement.

The problem with that, Orlando said, is that it can leave a child totally unprepared until “someone dies and the estate plan speaks,” Orlando said. “It’s almost like a lottery winner.”

There are ways to be more open without showing your kids your bank statement or breaking down every asset.

“Move toward transparency” gradually, Orlando suggested, adding that families shouldn’t expect to flip a switch overnight.

One of Orlando’s clients planned to leave each of their children $100 million, he said. Up until then, their kids had largely been supporting themselves, with no idea they would soon have nine-figure fortunes.

Orlando convinced the parents to put $5 million into wealth management accounts in each of the children’s names to prevent a shock to the system.

“Let’s get them to start developing skills,” he said. “If you want your children to be responsible for $100 million, don’t stay silent.”

2. There is no plan

A large part of Orlando’s work revolves around creating policies for families around everything from communication to investing.

If a family owns a business, there should be a conversation about who will take over control and ownership of it. If there is a foundation, there should be a conversation about its goals.

For example, say a grandparent is conservative and a grandchild wants to give all their money to Planned Parenthood. There will likely be a disagreement. Orlando’s suggestion: Find common ground, agree on a few key causes, and incorporate those into a philanthropy mission statement.

Guidelines help prevent future conflict, he said.

3. If you want to produce leaders, stop controlling them

According to the UBS survey, 43% of billionaires hope their children “grow the family’s business, brand, or assets, ensuring the family legacy continues.”

But that expectation can lead to conflict.

Orlando pointed to two billionaire clients with family businesses. The problem, he said, was that in both cases, the next generation wasn’t prepared because the patriarch or matriarch didn’t trust them with any decisions.

Think Logan Roy in “Succession” calling his kids “not serious people.”

The solution is for the leader not to micromanage, but to gradually hand over the reins through projects that are low-risk and allow the children to voice their opinions.

“That way we can go from a voice to a vote,” Orlando said. “There are these progressions.”



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