LESSON 18Identify Your Blind Spots with a Periodic Portfolio Defense

In a 2010 New York Times story about Tiger 21, one of our members noted, “We all learn from each other; that’s the magic of the place.”

The source of much of that magic is the Portfolio Defense (PD), our signature feature. Just about every monthly meeting includes a PD, as we call the grilling that each of us must undergo every year on the critical and often emotional choices we have made in our financial lives. Members often prepare for days or weeks in advance, and the actual defense usually lasts for 90 minutes, no holds barred, and covers every stock, bond, private investment, fund position, and piece of real estate we own—and in some cases, our philanthropic interests. As important as the numbers are in isolation, they come to life when members share their answers to a detailed set of questions about their goals, personal life, family, and their anxieties about protecting their wealth and transferring it to children and charities. More broadly, the questions force our members to explore the broader meaning of wealth in their lives, and in what ways it can be used to lever philanthropic, political, or family goals and interests.

I have been doing an annual Portfolio Defense for 18 years. Yet I still enter the room with a combination of trepidation and curiosity regarding what the response to the latest report on the State of Sonnenfeldt will be. Frankly, not everyone can handle such naked exposure. “I’ve ...

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