Excerpts from my new book, The Art of Playing Defense, which launches in two weeks; Bill and Melinda Gates divorcing

By Whitney Tilson

Tuesday, May 4, 2021

1) My new book, The Art of Playing Defense: How to Get Ahead By Not Falling Behind, is officially launching two weeks from today on May 18.

Further below are two excerpts from the book – the introduction and my favorite section, “The 12 Questions to Ask Before You Marry Someone.”

Unlike the three previous books I’ve written, which all focus on investing, this one is a labor of love. As I wrote in the dedication:

This book is dedicated to my three wonderful daughters, Alison, Emily, and Katharine, who make me proud every day.

If they find even a few nuggets here that help them discover what they want to do with their lives; overcome challenges; avoid setbacks; recover from adversity; seize opportunities; develop deep, loving relationships; achieve genuine happiness; and become the best people they can be, then, to me, the huge effort of writing this book will have been worth it.

And if it’s helpful to others as well, that’s icing on the cake!

To be successful and enjoy a happy life, it’s important to do all the right things: Become well-educated and wise, develop a strong work ethic, always act with integrity, and treat others well.

What’s equally important (but widely overlooked) is avoiding the calamities that can cause you to suffer, go back to square one, or worst of all, die a premature death.

My career has been focused on managing risks with investments. In this book, I turn my attention to the risks in our everyday lives.

The Art of Playing Defense is meant to be a practical and actionable guide filled with common-sense ideas for avoiding life’s 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. 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.

2) Speaking of “The 12 Questions to Ask Before You Marry Someone,” maybe I’ll send a copy of my new book to Bill and Melinda Gates, who are both likely to be asking these questions in the near future now that they’re divorcing after 27 years of marriage.

I’ve met them both and was saddened to hear the news, but not surprised, as I heard years ago that their marriage was in trouble. New York Times columnist Nicholas Kristof hinted at this in his op-ed two years ago, The Bill-Melinda Gates Romance Started With a Rejection. Excerpt:

After the marriage, in 1994, Melinda still struggled, and one flash point was the annual letter that Bill had been writing for the foundation they had established. Melinda was co-chair of the foundation and wanted to write it with him in 2013. Bill didn’t like the idea. “We both got angry,” Melinda writes, adding: “I thought we were going to kill each other. I felt, ‘Well, this just might end the marriage right here.'”

In the end, Bill wrote the letter for 2013 but included a section by Melinda. In 2014, it became a joint letter, but mostly written by Bill. Finally, in 2015 it morphed into a truly balanced letter.

I don’t think either Bill or Melinda made a mistake in choosing who to marry – they’re both exceptional, high-grade people – but, nevertheless, somehow their marriage fell apart over time.

I discuss this concept at length in my book in the chapter on “Calamity No. 3: A Bad Marriage, Often Ending in Divorce.” Marrying a great person is, of course, critical – but then, for the rest of your life, you need to keep your marriage healthy. It’s not easy, as there are so many ways for a marriage to deteriorate – sometimes quickly (e.g., infidelity), but more often slowly…

Book Excerpt No. 1: Introduction

After nearly two decades of managing money, I closed my hedge funds in September 2017 and launched an educational seminar business through which I sought to teach the next generation of investors everything I’d learned from my time “in the trenches.”

My first seminar, with a dozen young investors, was in December 2017. Half of my students were fund managers, while the other half planned to launch funds in the not-too-distant future. Based on their feedback, I developed a curriculum for our five days together that was focused 60% on becoming better investors and 40% on launching and building successful investment-management businesses.

Yet, much to my surprise, over the course of the week, we ended up spending only about a third of our time on investing and another third on launching a fund.

What was the final third?

Life lessons.

It wasn’t my plan to talk about these things, but whenever one of these topics came up, my students would pepper me with questions.

For example, at one point, I mentioned that many of my friends had gotten divorced in recent years. They asked me whether there were any common threads, which eventually led me to develop a list of twelve questions I think anyone should ask before marrying someone.

Another time, one of my students asked how I’d cultivated so many mentors.

Actually,” I replied, “there’s a five-step process…” And another long conversation ensued.

It soon dawned on me that teaching them this “worldly wisdom” was just as important as the formal curriculum I’d developed – and could be the basis for a book.

The Focus on Calamities

When I dove into this book, I started by writing about positive life lessons: work hard, become a learning machine, be nice, have high integrity, etc.

But a few chapters in, I ran out of gas and didn’t write a word for months. I’d lost motivation and couldn’t figure out why. I finally realized it was because I was having trouble finding anything fresh and interesting to say. How many books are there that extoll the virtues of things like hard work and developing good habits? Thousands! Sure, this stuff is important, but it’s all been said and written a million times before, so I didn’t feel like I was adding much.

But the calamities section I’d planned for the end of the book – now that was interesting! How many books are there about all of the horrible things that can ruin your life like cancer, a terrible accident, your marriage falling apart, getting thrown in jail, losing all your money, having no friends, or becoming addicted to drugs or alcohol?

I’d developed a slide presentation on calamities, and each time I taught it, my audience was riveted!

So I decided to change the focus – and title – of this book.

Fair warning: much of this book is a downer. Who likes to think about all the bad things that can derail your life? Most people would rather think optimistically and hope for the best. But if you don’t also think about avoiding calamities, you’re making a big mistake.

The foundation for a successful life is playing good defense. If you want to get ahead, it’s critical to avoid big setbacks.

Why Me?

At first glance, I may seem like the wrong person to be writing a book about calamities because I’ve suffered few of them.

I grew up all over the world in a loving, tight-knit family, I earned degrees from Harvard and Harvard Business School, I’ve been a (mostly) successful serial entrepreneur, my wife Susan and I are still happily married after 27 years and have three spectacular daughters, I’m in great health, and I have many wonderful friends. You can see why I count my blessings every day…

So why am I qualified to write this book?

Let me answer that question by asking one: If you wanted to learn to play tennis better, would you hire me or Roger Federer? For basketball, me or Steph Curry?

Similarly, if you want to learn how to avoid calamities, would you rather learn from someone who’s suffered a lot of them or someone who’s successfully avoided them?

It’s not an accident that I’ve suffered far fewer than my fair share of big setbacks. Rather, it’s primarily the result of two things. During my youth, I had two wonderful role models – my parents – both of whom I love and admire more than anyone. They surrounded me with love from the day I was born and made big sacrifices for my sister Dana and me.

By being excellent teachers and role models, they helped me avoid the calamities of youth: I didn’t get myself killed, stayed away from drugs and alcohol, and got a great education.

Then, as an adult, in addition to having a wonderful wife, I’ve had two more wonderful role models: famed investors Warren Buffett and Charlie Munger.

When I discovered them in the mid-1990s as I was first getting interested in investing, I studied them obsessively, reading everything by and about them and traveling to Omaha to attend the Berkshire Hathaway (BRK-B) annual meeting every May (I’d been to 21 in a row until the coronavirus forced the cancellation of the 2020 meeting).

What I learned from these two wise men about investing was invaluable. In the early days of my career, I had so little experience – and they were such brilliant, inspiring, and patient teachers! Had I not absorbed all of the investing lessons they imparted, I would never have achieved anything close to what I did. I beat the market year after year in my first dozen years and grew assets under management from $1 million to $200 million across three hedge funds and two mutual funds. I also launched successful investment conference and newsletter businesses, appeared regularly on CNBC for many years, was on 60 Minutes twice, wrote hundreds of articles, and coauthored three books.

I’ve come to realize, though, that the most important things I learned (and continue to learn) from Buffett and Munger go well beyond value investing. They fall under the category of what Munger calls “worldly wisdom.”

Much of what they preach is simple (as Munger jokes, “If it’s trite, it’s right!”): work hard, become a learning machine, have high integrity, develop good habits, be nice to everyone, marry the right person and maintain a strong relationship, and so forth.

They also spend a lot of time talking about calamities. I still remember the moment when I was at the WESCO (WCC) annual meeting two decades ago when Munger said, “All I want to know is where I’m going to die, so I never go there.”

Everybody laughed, but he continued:

I’m serious. Once you reach a certain position in life, you should spend most of your time trying to avoid the things that can derail your life and send you back to “go,” or worse. That’s true in investing, but it’s also true in life. What happens to many people is that even when they’ve got it made, they can’t help but stretch to try to grab the brass ring – and fall, bringing themselves to ruin.

Ever since, I’ve been studying calamities. Avoiding calamities is all about assessing risk – and that’s what I’ve been doing full time for more than two decades in the investment world. Most people aren’t very good at it because they tend to focus on vivid but unlikely risks while ignoring far more dangerous ones right in front of them.

For example, when I started mountaineering a few years ago, summiting hairy peaks like the Matterhorn and the Eiger, my mom flipped out. She begged me to stop and, when I refused, tried to enlist Susan in an “intervention.”

I explained to her that she was worried about the wrong thing. I’d estimate that I’m ten times more likely to die riding my bicycle nearly every day on the streets of Manhattan than climbing mountains a few days a year.

Another risk many people ignore until it’s too late is the risk of their marriage going bad. In recent years, I’ve seen this derail the lives of over a dozen close friends and relatives. In each case, I asked them to tell me what happened so I could learn from it and take steps to ensure it didn’t happen to Susan and me.

A final example I’ll cite is car safety. In the past two years, my wife, three cousins, and three friends have been in seven – SEVEN! – serious accidents. In each case, their cars were totaled, resulting in multiple concussions and, tragically, two deaths. This affected me deeply and, even though our 10-year-old Volvo was running fine and built like a tank, led me to buy a new car – the exact same model, but with a lot more safety features. It was a wise decision, as Susan was in a serious accident not long afterward.

Book Excerpt No. 2: The 12 Questions to Ask Before You Marry Someone

1) Are they a warm, kind, and good-hearted person, both toward you and others? Do they have a mean bone in their body? How do they treat people like employees, waiters, and taxi drivers? Do children and dogs like them?

This is so important – and it’s so easy to be fooled because, of course, the person you’re dating is going to be on their best behavior around you. That’s why it’s critical to watch how they treat others, especially those they don’t perceive to be peers. Children and dogs are often much better judges of character than you are!

2) If you weren’t romantically interested in each other, would you be close friends? Do you make each other better?

Over time, when the passion and romance aren’t so intense, there had better be a solid foundation of friendship, or you’re in trouble. You want to be with someone who gives you frank feedback and smooths your rough edges – as Susan regularly does with me!

3) Do they have high integrity? Are they a stable, solid, predictable person who you can count on 100%? Do you trust them completely? Are there any issues with anger management, violence, narcissism, alcohol, or drugs?

There can be no compromise in this area. If you don’t trust someone with your life – if you’re not 100,000% certain that they would never cheat on you or knowingly hurt you, directly or indirectly, in any way – then RUN! If you find yourself rationalizing, “Well, he’s great most of the time, but sometimes when he’s had too much to drink…” RUN!

One of my friends who’s dated a lot of people told me that many of them can’t “relax and be themselves” until they’ve had many drinks. If you observe this, RUN!

4) Do you share core values, e.g., self-improvement, giving back/philanthropy, meritocracy, humility, life balance, spirituality, thinking before acting, looking for win-win solutions?

Every person’s list here will be different. I thought about adding “political views,” but you’ll have to decide that for yourself.

5) Are they intelligent and intellectually curious? Do you find them interesting?

This isn’t code for “did they attend an elite college?” My dad is from a prominent family in Connecticut and went to a private high school before attending Yale, while my mom is the daughter of a Seattle fireman and went to public schools all the way through the University of Washington. So what? They’re both smart, intellectually curious, and interesting – and have been happily married for more than 58 years!

6) Do they like to do fun things and have a zest for life? Are they a happy and optimistic person? Do they have a good sense of humor and make you laugh?

There are so many people who look great on paper – they’re nice, went to a good school, have a solid job, etc. – but are just, well… boring. You don’t want to be married to someone like that unless that’s what you’re looking for, of course!

7) Do they have a strong work ethic and a purpose?

Initially, this question was “Do they have a good job or career,” but I changed it because some people choose to do things like write books, raise kids, or do volunteer work – and they’re very happy and are wonderful spouses. The point of this question is that if you’re a driven person and your spouse is a lump, your marriage isn’t likely to last.

8) Do they come from a stable family? Do you want to spend time with them (because you will!)?

The first part of the question here is tricky because it seems unfair to hold it against someone if they happen to come from a messed up family. But I’ll be honest: I’d rather see my daughters marry guys whose families are similar to ours – filled with deep, long-term, loving relationships.

9) Do your friends and family like them?

Similar to the dogs and children question, someone may be able to fool you… But they’re unlikely to be able to fool all of your friends and family. Ask people close to you what they think – and listen carefully!

10) Do they have similar views on big issues such as where to live, children (how many, what religion, how will child-rearing duties be split), whether one of you will stop or cut back on working to raise the kids, and finances (spending habits, lifestyle, debt, the importance of having a lot of money)? Will they be a good parent?

As your relationship deepens, you’ll want to think about these things – and have some conversations about them, however difficult that might be.

Regarding religion, I remember on my first date with my wife, I told her we could raise our kids Jewish. It was certainly premature – I said it with a smile – but it’s a critical conversation to have if you and your potential spouse are from different religions. (I wasn’t raised religious, so it wasn’t a sacrifice for me – and I’m delighted that my daughters are Jewish, as I fully embrace the values of the religion.)

Another huge issue is balancing both of your careers with the demands of raising a family. A lot of guys have the sexist assumption that their wives will sacrifice their careers once kids come along, which can lead to anger, resentment, and eventually, divorce.

11) Have they had long-term relationships in the past? How have they ended? What would previous boyfriends or girlfriends say about them?

When deciding whether to raise children and spend the rest of your life with someone, you should be less concerned with how someone is 99% of the time than with how their worst 1% looks like. Observing or talking to ex-partners is a good place to start.

12) Do you think they’re attractive, and do you have a wild, passionate sex life?

A good sex life is an important element of a healthy marriage, but I have deliberately listed this as the last and least important question in part because so many young people seem to put it first. I know a number of guys who are trapped in miserable marriages with women who are mean, shallow, or otherwise unpleasant – but, boy, were they hot and sexy when they were younger! To quote the old adage, these guys let their little heads think for their big ones… And have been paying a big price ever since.

Best regards,


Whitney Tilson
Get Whitney Tilson’s Daily delivered straight to your inbox.

About Whitney Tilson

Prior to creating Empire Financial Research, Whitney Tilson founded and ran Kase Capital Management, which managed three value-oriented hedge funds and two mutual funds. Starting out of his bedroom with only $1 million, Tilson grew assets under management to nearly $200 million.

Tilson graduated magna cum laude from Harvard College with a bachelor’s degree in government in 1989. After college, he helped Wendy Kopp launch Teach for America and then spent two years as a consultant at the Boston Consulting Group. He earned his MBA from Harvard Business School in 1994, where he graduated in the top 5% of his class and was named a Baker Scholar.

Click here for the full bio.