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Lessons from celebrity-estate planning cases for advisors.

Celebrity Estates: All the President’s Money with Megan GormanCelebrity Estates: All the President’s Money with Megan Gorman

From George Washington to Donald Trump, Chequers' Megan Gorman explores U.S. presidents' financial decisions.

David H. Lenok, Senior Editor

February 24, 2025

With Donald Trump appearing at his recent inauguration flanked by tech billionaires, the connection between presidents and the almighty dollar is more apparent than ever. However, Trump is not the only president with an interesting relationship with money.

In this episode of the Celebrity Estates podcast, host David Lenok welcomes back Megan Gorman, a wealth and tax planning expert and founding partner at Chequers Financial Management, to discuss her new book, All the President’s Money: How the Men Who Governed America Governed Their Money. Listen as they delve into U.S. presidents’ financial decisions and estate planning strategies, uncovering common challenges such as procrastination and poor communication with heirs.

Through historical examples, Megan and David emphasize the importance of clear estate planning, communication with heirs and considering the legacy one’s financial decisions leave behind. The discussion underscores how estate planning lessons from historical figures can be applied to modern financial planning, making it a compelling episode for advisors and individuals alike.

Key insights include:

  • Insights into Harry Truman’s “letter of wishes” 

  • The surprising financial savvy of Warren G. Harding

  • How George Washington’s estate plan unintentionally endangered Martha

  • Abraham Lincoln’s lack of an estate plan despite his legal background

  • And more

Resources:

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About Our Guest:

Megan is the founding partner of Chequers Financial Management, a fee-only planning firm that specializes in high-net-worth and ultra-high-net-worth families in San Francisco, California. Megan heads the firm’s family office services practice.

As well, Megan is a Senior Contributor for Forbes in personal finance and tax. She is also quoted regularly in the press as a tax and financial planning expert including such publications as The Wall Street Journal and The Washington Post. She blogs at TheWealthIntersection.com, has appeared on numerous podcasts, and is a regular weekly commentator on The Money Tree Podcast.

Listen to the Celebrity Estates Podcast

About the Author

David H. Lenok

Senior Editor

David Lenok is a senior editor for Wealthmanagement.com and Trusts & Estates. He's an attorney admitted to practice in New York and writes about general wealth planning issues.

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