Complex assets do not always have an obvious exit.

Complex assets do not always have an obvious exit.

A publicly traded stock can be sold before lunch.

A position in a closed-end private equity fund may be locked up for ten or more years, with no secondary market and no ability to exit on demand.

A direct ownership interest in an operating business may be saleable, but only at a time, price, and structure that works for both buyer and seller - which is rarely the moment of death.

Even personal residences can be difficult and time-consuming to sell if families end up selling at the wrong time.

Wealthy families tend to hold complex assets for longer than they originally intended. They have a tax incentive to hold since selling triggers gain recognition, often on assets that have appreciated over many years. The step-up in basis at death can eliminate that gain entirely, making the "wait until death" strategy look attractive on paper.

The result is that many families hold complex assets until death without ever making a deliberate choice to do so.

Part of Wealth Machine, a Secret Art of Planning series.

Register for Notre Dame, October 28–30, 2026, and attend my presentation and the other sessions.
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