Good morning, friends!

Jim O’Shaughnessy is a Wall Street legend and the founder, chairman, and chief investment officer of O’Shaughnessy Asset Management, which has $6.2 billion in assets under management.

He is also my friend, so I asked him to write a guest column that has nothing to do with his role as an investor. In this post, O'Shaughnessy reflects on his most important role: a father.

Why Writing Letters to Your Kids Is the Best Gift You Can Give Them as Adults
By: Jim O’Shaughnessy

“Letters are among the most significant memorial a person can leave behind them.” ~Johann Wolfgang von Goethe

I’ve always believed in the written word. Having to put your thoughts in writing helps you understand if you clearly understand what—and how—you want to say something. And if you keep written journals, there is simply no way to let hindsight bias take over, for there, in your own hand, is what you thought about something at the time, with revisions through selective memory impossible.

Writing clarifies. It illuminates. It helps you follow your own growth (or decay) in the way you look at the world and how your ideas have changed—or remained the same—over the course of your life. As someone with boxes and boxes of old journals, if I want to know what 21-year-old me thought about something, all I must do is pull out that journal and read. Sometimes I’m amazed by how much my views have changed—often dramatically—as I have made my way through life.

Yet equally telling is how little some of my foundational beliefs have changed. For the most part, I find that that, if anything, they have become stronger, better articulated, and better supported.

I’m a big believer in reading as much as you can that takes the other side of what you think. We’re all subject to confirmation bias, and a great habit to build is to always search out beliefs that counter your own. If they make you change your mind, as has happened with me, then your original belief really wasn’t that sound to begin with, so, by always challenging yourself, you make your thinking stronger and more truly reasoned.

You should also try to seek out the best arguments for things you don’t agree with—called creating a “Steelman” as opposed to the far more common “Strawman.” You’ll often see nothing but Strawman arguments in popular media and I’ve sadly concluded that, for the most part, popular media stopped presenting serious, well-articulated essays that might help sway you to a different point of view. But there are more great, serious essays available today to all of us than ever before—it’s part of what I call “The Great Reshuffle” which is the ongoing transformation of almost every aspect of our lives that technologies and inventions are ramping up for society at an exponential rate.

We could be living through one of the most interesting periods of human history, and you have a chance to narrate it for yourself and your children. I’ve long advocated writing continuous letters to your kids, but given all the changes we’re living through, it might give you an extra special opportunity to let your kids see it all unfold.

Related: Jim O'Shaughnessy on Bitcoin, Investing Psychology, and the Secret to a Long-Lasting Marriage

This compels me to again urge every parent reading this to get in the habit of writing your children a series of letters so that they too can understand you, and, with luck, themselves better. Having to articulate thoughts in a letter allows you and your children time to reflect on things in a way that is often difficult in the day-to-day events of your lives together.

It’s something that I always wish my dad had done, as we had a rather difficult time understanding each other and I think a series of letters from him would have helped me understand him much better than I ultimately did.

Ideally, you should start as soon as you can and continue to write over the years. I started when my son, Patrick, was 7 days old and continued until my last child turned 21. As each child hit 21, my wife—the true marvel in the parenting hall of fame–would select photos and publish the letters in book form for each of my kids. The last letter of each book was written specifically to the child the book was for, but otherwise, all the letters were for all my kids.

Below is the first letter I wrote, which I hope spurs you on to do this for your kids. Rarely are things 100 percent win/win, but in the case of letters for your kids, that’s the reward for taking the time as your kids grow to have a conversation with the adult they will become.

April 22, 1985

Dear kids,

Firsts are exciting and somewhat perplexing. This is the first entry in a book I’m going to keep for you; its direction not yet known to me. Thus, the thought of giving you something created over the years excites me, but I am also perplexed about what I really want to write here.

I know that I don’t want this to be a diary, detailing the days, for although we already love you we know that a diary of when you eat and sleep wouldn’t be exciting reading. In some ways, I hope to be able to say all the things fathers want their children to know, yet so many times forget, or neglect to tell them.

If nothing else, you will see how I changed, from a 24-year-old brand new father, to one who has watched you grow up, and, with luck, grown up myself.

Most of all, you may be able to know both me and yourself better through this collection of “letters” and we must all strive to understand ourselves and those we love, for through our understanding and experience comes the wisdom that no one person can teach another, no school can transmit it. It must come from within, from learning, from logic and experience. If I could, I would describe it for you; I can’t. Perhaps you will agree when you are older.

I also want to tell you about me, my life, my thoughts, perhaps you can gain some understanding of yourself through understanding me. If I was going to describe my own impulses in a paragraph, it would be advice to you as well, so here, in Lao Tzu’s words, it is:

“He who knows much about others may be learned, but he who understands himself is more intelligent. He who controls others may be powerful, but he who controls and has mastered himself is mightier still. He who receives his happiness from others may be rich, but he whose contentment is self-willed has inexhaustible wealth. He who occupies a place provided for him by others may live a long life, but he who dwells in his own self-constituted place, even though he decays, is eternal.”

That bit of wisdom really embodies many of my goals, and many of my beliefs.

You will always be only as good, only as happy, only as successful as you perceive yourself to be. Happiness springs from within, never from without. Virtue too; honor; and love. All the things that make a life worth living. Thus, if you are unhappy, don’t look outside yourself for causes, the reside within; likewise, if, like me, you are happy, understand the source within your soul.

Love,

Dad

Tweet This Article

—

THE PROFILE DOSSIER: On Wednesday, premium members received The Profile Dossier, a comprehensive deep-dive on a prominent individual. It featured Jeni Britton Bauer, the artisanal ice cream scientist. Become a premium member & read it below.

The Profile

The Profile Dossier: Jeni Britton Bauer, the Artisanal Ice Cream Scientist

Jeni Britton Bauer is something of a scientist or a mixologist of ... ice cream. Britton Bauer has perfected nearly every step of the ice-cream-making (and eating) process. She doesn't use stabilizers, emulsifiers, or egg yolks to create her ice cream — and that's by design…

Read more

4 days ago · 1 like · Polina Pompliano

—

The following is the first edition of "The Best of The Profile” series, including some of my all-time favorite profiles, podcasts, documentaries, interviews, and podcasts.

PROFILES.

— The NFL coach searching for his family [**HIGHLY RECOMMEND**]
— The world’s most feared investor
— The In-N-Out burger billionaire
— The LeBron James of short selling
— The grandfather of entertainment
— The modern-day explorer
— The godfather of modern surveillance

PEOPLE TO KNOW.

The NFL coach searching for his family: I’m normally suspicious of stories with headlines that claim they’re “jaw-dropping,” but this one totally lives up to the hype. At 44 years old, Kansas City Chiefs running backs coach Deland McCullough went searching for his biological parents. What he found out will stop you in your tracks & make you realize life is just a series of weird coincidences. This is one of my favorite profiles. (Sports Illustrated)

“Being irresponsible is not neutral. When you’re irresponsible, someone becomes responsible for what you’ve been irresponsible for.”

The world’s most feared investor: Paul Singer, the head of hedge fund Elliott Management, has developed a uniquely adversarial, and immensely profitable, way of doing business. He has been called "aggressive, tenacious and litigious to a fault," and named "The World's Most Feared Investor." This is a comprehensive look at what happens when this ruthless activist investor begins to sniff around your company. It’s not so pretty.

“What I came to feel relatively early on in my career is that manual effort was actually not only a driver of value and profitability but an important way to control risk, dig yourself out of holes when you slip into a ravine.”

The In-N-Out burger billionaire: With a net worth of $3 billion, Lynsi Snyder is the sole owner of burger empire In-N-Out. Snyder’s past lies in stark contrast to the company’s long-standing stability — she never graduated from college, battled through drug use, and went through three divorces. Taking over the franchise in 2010 gave her a sense of purpose. “When you persevere, you end up developing more strength,” she said. (Forbes)

“It’s not about the money for us. Unless God sends a lightning bolt down and changes my heart miraculously, I would not ever sell.”

The LeBron James of short selling: Jim Chanos is the founder of the largest exclusive short-selling investment firm, Kynikos Associates. He has been dubbed a "catastrophe capitalist" because he succeeds when others lose money. Kynikos is the lone short-selling hedge fund of any size — and the only one that that has been in business since 1985. He gained star power on Wall Street when he accurately predicted the demise of Enron. (Institutional Investor)

“People end up getting more enthralled with the story than they are with the numbers. When this market starts to crack, and they always do, there are a lot of investors who will come running to Chanos.”

The grandfather of entertainment: Quincy Jones has an insane story about every famous person you can think of — Michael Jackson, Elon Musk, Frank Sinatra, and Tupac. But nothing compares to the tale of his upbringing. At 7 years old, he had to go out and catch rats so his mom could cook them for dinner. He stops and reflects on the fact that the poor kid who ate rats is now an 84-year-old music legend telling the story from a hilltop mansion. He says:

“Your dreams always have to be big. And mine were huge."

The modern-day explorer: Sarah Marquis is redefining what it means to be a modern-day explorer. She’s a hiking specialist who spends months, sometimes even years, walking across scarcely traveled swaths of earth. From 2010 to 2013, she trekked 10,000 miles from Siberia to the Gobi Desert, then (after 13 days on a cargo ship) across Australia. She has camped in minus-30-degree cold and endured blizzards, sandstorms, mudslides, dengue fever, and an almost fatal tooth infection. Yet she has no plans to stop. (Outside Magazine)

"How does a restless person find a still spot in the world? How can a nomad make a home, that is at once sustaining and invigorating, not boring?"

COMPANIES TO WATCH.

The godfather of modern surveillance: Over the years, Palantir has worked with some of the government's most secretive agencies, including the CIA, the NSA, and the Pentagon's Special Operations Command. This profile delves into what it means for a tech company to be marketing itself as the most powerful weapon in the national-security state’s arsenal. (New York Magazine)

✨ This installment of The Profile is free for everyone. If you would like to get full access to all of the recommendations, including today’s audio and video sections, sign up below.

AUDIO TO HEAR.

Hilary Swank on conquering her mind: For the film "Million Dollar Baby," Hilary Swank managed to pull off the physicality of a female boxer in only 90 days. Her mind screamed at her every single day, she says. "Just show up, and put the work in," Swank adds. "And next thing you know, you're breaking through barriers that you never thought possible." In this podcast, the legendary actress shares the techniques she uses to shatter her fears. (Link available to premium members.)

Mark Cuban on building wealth: In this podcast, Mark Cuban gives listeners the keys to getting (and staying) rich. "Everyone's a genius in a bull market," Cuban says. "The great stock pickers aren't only the ones who make money when things are going up — they make money all the time." This is a masterclass on building a business, investing your money, and keeping your ego in check. (Link available to premium members.)

VIDEOS TO SEE.

Chris Voss on the power of nuance: Nothing in life is fair, people aren’t rational actors, and you should never compromise. In this wide-ranging interview, Voss explains the importance of nuance in high-pressure situations. For instance, there’s a lot of power in recognizing the facts while also understanding how the other person interprets those facts. It’s called perspective. Deconstructing a situation and seeing it from multiple angles is key in gaining the upper hand in a negotiation. (Link available to premium members.)

Lori Gottlieb on the unreliable narrator: We are all the unreliable narrators of our own stories. I am. You are. So is everyone you know. In this talk, psychotherapist Lori Gottlieb explains how two sets of facts can be twisted, emphasized, and minimized depending on the person telling the story. You're already a good writer of your life story. Now, how can you become a good editor of it? (Link available to premium members.)

Jeff Bezos on why the brilliant is found in the mundane: In this speech from 13 years ago, Amazon founder Jeff Bezos explains his idea for the creation of Amazon Web Services (AWS). He breaks down Amazon's strategy: Rather than focusing on short-term profit, Amazon always had an eye on the longer-term gains. “If we’re not the leader 5 to 10 years from now, it’s because we didn’t execute well," he said. (Link available to premium members.)