The Heart: Lunch With Jim O’Shaugnessy

When I first started writing here on I heart Wall Street, it was simply out of frustration.

The title came to me serendipitously while talking with Meb Faber about the ills of Wall Street, the existential crisis of Wall Street, if you will. It was a very I heart Huckabees moment for me.

And that was it — I was stewing in the reality of what it is vs. what it could be.

Are we connected in the blanket of the universe or destined to play out a nihilistic future full of futility — and petroleum?

To me, and my middle-class upbringing, what Wall Street represented was an opportunity to shine. Very Trading Places inspired, to be clear. Anybody with the right skills and knowledge, whether it be street knowledge or book smarts, can do what I do. There’s no precise formula when it comes to giving good advice. It takes a whole bunch of chutzpah…and heart.

We’ve all had our fill of the evil. “Greed is good.” You know the schtick. But here’s the thing… it’s not really like that. At least not always. There are good stewards and good people who really are trying their best not to shave your pennies just for them, but to really add value to the world — yours and mine.

I’m lucky enough to have met one of them recently. Jim O’Shaughnessy. This man is one of the great minds on Wall Street. And, he invited me to lunch because of this tweet.

Two months later, sitting across the table from him in Manhattan, I couldn’t stop smiling.  We talked about psychology, science, markets, genetics, politics, religion, medicine, health, family, and history. It was a dream come true. He’s a fountain of knowledge and my cup was never empty.

I told Jim I thought Wall Street was the Hollywood of business. You don’t need to go to Harvard or Julliard to be listed. You don’t need to sell out either. You can mold the matrix to you if you have what it takes. He laughed. He “never thought about it like that.” Maybe it’s because I am naive still, but I think he heard it and the laugh meant he knew it was true. Maybe he didn’t. I can’t tell you for sure. I can tell you some things I did learn, though, at the knee of Jim…

You might be lucky. You might have a head start. That doesn’t mean you finish strong. No one is guaranteed success. That takes mindful care. That takes principle. That takes diligent work no matter where you start or how lucky you might be. Jim was born into a wealthy family. By most measures, he had a head start. But it wasn’t the money that gave him that head start. It was what the family brought to him in the lessons and virtues they gave him.

That’s, to me, what’s so powerful when you meet someone like Jim. Proud, loving father. He’s a gracious and giving friend. An unassuming man who’s educated and polite, casual and friendly, approachable and warm, curious and ready to listen, personable and welcoming, caring and sharing. That happens at the family dinner table way before it happens at the table in the boardroom.

You might have some picture in your mind that the ‘elite’ are a bunch of pompous assholes who don’t care and who lie, cheat, steal, scrape, and kill for what’s theirs. You might think that the game is underhanded and that you can’t succeed unless they fail.

You couldn’t be more wrong. There is Heart on Wall Street. And, it’s alive and well with people like Jim.

He gives back because he is so lucky, and he knows it. There’s nothing wrong with luck, particularly when it’s good luck. He also gives back because he knows — we’re connected in the blanket.

I learned some other things too.

He is a lifelong learner because he is relentless in the pursuit of knowledge and his quest to keep improving himself.

He read to his kids for years after they were reading on their own. All his children are successful because he wasn’t trying to mold them into him.

He wouldn’t let his son, Patrick, quit karate when he was 10 just because he wanted to. His son needed to convince him.  Patrick did eventually– as only he could — with logic, reason, and heart.

Patrick also didn’t start at the top just because his dad had forged a path. He had to find his own way in the world. And he did, because Jim taught his children that’s the way it works if you want to endure and really make your mark in the world. Never settle for less with your own children.

Jim is a great father, which as a fellow dad, is humbling to witness. There are a million sad father/son/daughter stories on the earth. That’s not what Jim has with his family. He has led by example and encouraged each of his children to find their own answers. “Great question, look it up…” as he pointed to his library, is what he told me. And they have. This mantra, his mantra, to “look it up” as a parent has served his family well. It will also serve mine well now.

I also learned that Jim is like me, and maybe you. He does dumb things. He also gets back up, laughs, dusts himself off, and tries again. That’s chutzpah. That’s heart.

I could and would share more, but I didn’t even tell him I was going to write this. So, I’ll close with something he shared with all of us…

Hopefully, I captured the spirit of what he intended to share with me, with you. I don’t know. What I do know is this…the ‘heart’ of I heart Wall Street beats with people like Jim. Don’t ever get that confused.

Reminder: The Blanket

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