The people who build the most remarkable fortunes tend to share certain traits: drive, vision and a relentless focus on the next opportunity. Too often, they share one more: an estate plan that never caught up with their success. When a prominent wealth creator dies unexpectedly, and sometimes far too young, the gap between what they built and what they planned for can leave their families, businesses and legacies exposed to a costly and very public attack.
Key takeaways:
Founders, entrepreneurs, and family business owners often have fast-growing wealth, complex assets, and a public profile, and they tend to put off uncomfortable tasks like estate planning.
Having no plan, or an outdated one, is the most common cause of family conflict after death. Estate documents should be updated after every major life event, such as a marriage, a child's birth, or a sudden change in wealth.
Plan for the worst case, including for the business. A plan should include contingency bequests and named successor executors and trustees, in case family members and trusted advisors all die at the same time. Business owners, even younger ones, should name contingency managers and leaders because a gap in leadership can quickly destroy the business's value.
Set up assets so the family has cash for estate taxes. Some US relief provisions let families pay estate taxes over 15 years and avoid a "fire sale" of business assets. However, the assets have to be structured in advance to qualify.
Treat reputation as part of the estate and keep thinking ahead. This matters because a public figure's reputation can directly affect the value of their estate.
When the headlines become the cautionary tale
Two recent disputes illustrate the stakes. After actor Chadwick Boseman died without a will, his brothers sought to remove his widow as administrator of his estate. Following the death of actor Malcolm-Jamal Warner, his widow pursued a $1.2 million claim arising from a decades-old estate plan and prenuptial agreement that Warner had never updated. As NBC News reported, estate planners view these cases as reflecting the most common mistakes that fuel family conflict after death: having no plan at all or relying on one that no longer fits the family's circumstances.
These are hardly isolated examples. Lengthy estate disputes have plagued famous figures for decades, including Jimi Hendrix, Amy Winehouse, Prince, James Dean and Aretha Franklin. Many prominent individuals simply lack guidance in organizing their estates and do not think of doing so themselves. Combine that with statistical trends showing that celebrities often die earlier than the public, and the result is outsized risk.
Why wealth creators are especially vulnerable
The lessons extend well beyond Hollywood. Founders, entrepreneurs and family business owners face many of the same pressures: rapidly growing wealth, complex assets, a public profile and a natural tendency to postpone tasks that feel uncomfortable. Many people view creating a will like getting a root canal. It’s something they think will be painful, and they put it off as long as possible. But once it's done, it’s comforting to know that if anything happens, there are safeguards in place.
Five lessons for families of significant wealth
While it may seem daunting at first, there are five steps that individuals can take to make planning more approachable:
Make a plan and keep it current. A will is only the starting point. It’s important to update estate documents after every major life event, including marriage, the birth of a child or a sudden change in wealth. The Warner dispute shows how an outdated plan can be nearly as problematic as none at all.
Plan for the unthinkable. There should always be contingency, or “wipeout,” bequests and designations of successor executors and trustees in place in case immediate family members and trusted advisors all die simultaneously.
Protect the business, not just the family. Even a young-to-middle-aged owner of a large family business should have contingency management and leadership designations in place. Leadership vacuums can quickly destroy enterprise value.
Structure assets to preserve liquidity. Certain US relief provisions allow families to pay estate taxes over 15 years and avoid a “fire sale” of business assets, but only if the assets are structured to qualify. There’s no substitute for a solid plan.
Manage reputation as an estate asset. For ultra-high-net-worth and prominent clients, retain a media advisor or crisis manager, and write positive obituaries in advance. A public figure's reputation can directly affect the value of the estate they leave behind.
Thinking several moves ahead
As Citywealth reported, estate planning is like playing chess. It’s important to plan multiple moves ahead because you cannot control everything and must be prepared for what comes next. For those who have spent a lifetime building wealth, a thoughtful and regularly reviewed plan is the final, and perhaps most important, move in protecting what they have created.
Join us in New York City
To explore this topic further with Katten's Private Wealth team, attend the upcoming 2026 Private Wealth and Fiduciary Seminar New York on November 4. Space is limited; register today to reserve your seat.
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