A family office built around a $2 billion estate had to prepare for the transfer of wealth from its Generation 1 founder to 23 descendants across three generations. Its holdings included liquid securities, alternative investments, and a substantial hotel and residential real estate portfolio. The existing estate plan had not kept pace with the family’s growth. It did not account for all three generations of heirs, gave no clear framework for who would control the family office and its hotel business, and left the family exposed to a large estate tax bill with limited liquid assets to pay it. When the founder passed away sooner than expected, the timeline accelerated and every workstream came under pressure.