Get ready for a broad ranging and provocative talk by a notable Wall Street veteran. Whitney Tilson’s career has been focused on managing risks with investments. His book, The Art of Playing Defense is meant to be a practical and actionable guide filled with common-sense ideas for avoiding calamities, such as marrying the wrong person or having a good marriage go bad, getting thrown in jail, going bankrupt, or suffering a debilitating illness or injury.

Whitney says, “I’ve managed to avoid these disastrous outcomes – and hope I can help you do so as well! It’s no fun thinking about all the things that can go wrong in life, but if you want to get ahead, you have to start by not falling behind.”

As a successful investor, we asked Mr. Tilson to share with us his approach which has helped him and others avoid the major market downturns of the 21st Century. We are also curious about his “Twelve Questions to Ask before Marrying Someone” and how his 25-year-old daughter received his advice. With our proximity to NYC, we also couldn’t pass up the opportunity to hear from him about his recent run for the Democratic nomination for mayor in 2025.

Referred to the DMA by Mark Nunan

Whitney Tilson

Whitney Tilson is Editor of Stansberry Research, which provides advice, commentary and in-depth research and analysis to help people become better investors. The business has more than 100,000 paid subscribers. Mr. Tilson founded and, for nearly two decades, ran Kase Capital Management, which managed three value-oriented hedge funds and two mutual funds, with assets that peaked at over $200 million.

Mr. Tilson published his fourth book in 2021, The Art of Playing Defense: How to Get Ahead by Not Falling Behind. He has also co-authored two books, The Art of Value Investing: How the World’s Best Investors Beat the Market (2013) and More Mortgage Meltdown: 6 Ways to Profit in These Bad Times (2009), and was a contributor to Poor Charlie’s Almanack: The Wit and Wisdom of Charles T. Munger (2005), the definitive book on Berkshire Hathaway Vice Chairman Charlie Munger. In addition, he has written for Forbes, the Financial Times, Kiplinger’s, the Motley Fool and TheStreet.com.

He has appeared dozens of times on CNBC, Bloomberg TV and Fox Business Network, was on the cover of the July 2007 Kiplinger’s, has been profiled by the Wall Street Journal and the Washington Post, and has spoken widely on value investing.

Prior to launching his investment career in 1999, Mr. Tilson spent five years working with Harvard Business School Professor Michael E. Porter studying the competitiveness of inner cities and inner-city-based companies nationwide. He and Professor Porter founded the Initiative for a Competitive Inner City, of which Mr. Tilson was Executive Director. Mr. Tilson also led the effort to create ICV Partners, a national for-profit private equity fund focused on minority-owned and inner-city businesses that has raised nearly $500 million.

Mr. Tilson received an MBA with High Distinction from the Harvard Business School, where he was elected a Baker Scholar (top 5% of class), and graduated magna cum laude from Harvard College.

Mr. Tilson is an avid mountaineer – he climbed the Nose of El Capitan in June 2020 and has summited Mt. Kilimanjaro, Mt. Blanc, the Matterhorn and the Eiger. He also regularly competes in obstacle course races, including the world championships pro division. He has run seven 24-hour World’s Toughest Mudders, winning the 50+ age group twice and setting the all-time age-group record of 75 miles in 2016.

Mr. Tilson spent much of his childhood in Tanzania and Nicaragua (his parents are both educators, were among the first couples to meet and marry in the Peace Corps, and have retired in Kenya). Consequently, Mr. Tilson is involved with a number of charities focused on Ukraine (to which he has traveled four times since the invasion and raised more than $18 million), education reform and Africa. Most recently, he was a candidate in the 2025 Democratic primary for Mayor of New York City.

Mr. Tilson lives in Manhattan with his wife of 32 years, with whom he has three adult daughters