Tax Screw-Ups and People Problems: Experts Reveal Biggest Blunders of Rich Families

There’s no single way to handle massive wealth. There are, however, some common mistakes to learn from.

A famous line in an F. Scott Fitzgerald short story declares that the very rich are different from you and me. The obvious difference: While the 99.9 percent strive to make a living, the 0.1 percent are working out what to do with the wealth they already have. Preserving and investing and donating and spending wealth is more than a full-time job and requires multiple types of expertise. Pitfalls abound, especially within families. Speak to a few family office experts, and you’ll hear the phrase “When you’ve seen one family office, you’ve seen one family office.” In other words, there’s no uniform method for handling great wealth. But press them on common errors, and they have a lot to say about patterns that trip up even those with the best intentions. In these pages a group of professionals from family offices, investment managers, estate planners, art advisers, and other disciplines describe mistakes they’ve seen. Fitzgerald wrote that there are “no types, no plurals.” But it turns out there are some lessons we can all learn.

Matthew Weatherley-White
Co-Founder and Impact Investing Specialist
Caprock Group

There’s almost a predisposition to falling in love with mission-driven impact investments like addressing climate change, or food deserts, or the unbanked. You so want the entrepreneur to succeed that you’re unintentionally willing to ignore negative variables in due diligence, for example. It’s easier to be dispassionate with investments that aren’t philosophically aligned with what you see as your mission in the world.