Jim O’Shaughnessy

Supported by Greenhaven Road Capital, finding value off the beaten path.

Jim O’Shaughnessy joined his Patrick O’Shaughnessy on the Invest Like the Best podcast to share some life lessons. Serendipitously I listened to Sean Iddings on Five Good Questions and he mentions the book Thirty Lessons for Living. Jim would make a good addition to the book. What I liked most was Jim’s attitude. “Everyday I woke up and said, boy I’m lucky to be alive today because I’m going to go in there and figure out more.”

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Jim’s learning started early. He remembers being a kid at the family library and hearing the adults discuss investment choices. The debate centered on personalities. That’s interesting, thought Jim, what about the numbers? He snuck off and did some research and found that the best returns were from companies with low P/E ratios, not dynamic leaders.

Often the genesis for better ways is someone seeing the old way and thinking, that’s not how I’d do it.  Eric Maddox questioned interrogation techniques. Ray Kroc questioned why a sleepy town had a great burger place. Daryl Morey questioned a Sports Illustrated cover.

But because a new idea is better, doesn’t make it easy. Just because Jim unearthed something that worked didn’t mean he could do it. Behavior is simple but not easy. 

“Investing is like dieting. There are a million diet books on the market today. Most of them have simple, easy to execute plans and it is remarkable difficult to get anyone to use that simple system. It’s all emotion.”  – Jim

“A lot more than people think is pure discipline.” – Patrick

“I couldn’t agree with you more.” Jim

To hijack a quote Jim would appreciate: “The name of the thing is not the thing. The stated returns are not your returns.

Trouble begins when you deviate from a good plan, says Jim. “The four horseman of the investment apocalypse are fear, greed, hope, and ignorance.” The first three are all about emotions.

Once Jim figured out what to do (use the numbers) and how to do it (with discipline) he started to build out his company. He gave four pieces of business advice.

  1. Hire adults for decentralized command. “You tell me the way to do it and that’s how we’re going to do it.”
  2. Be consistent in your actions. Jim says he has a low standard deviation.
  3. About meetings. “Meetings, for the most part, are a waste of everyone’s time
  4. Reputation. “Our business is based almost entirely on trust.”

Through all this, Jim had an attitude of discovery and the work didn’t feel like work. Phil Jackson opened his book this way:

“When you do things from your soul, you feel a river moving in you, a joy.” Rumi

And with this attitude, you’re motivated to practice and do many repetitions. Jim says that if you want to learn about art, “you want to look at tons of art.”

Here’s how Arnold Schwarzenegger put it:

Here are the books Jim O’Shaughnessy suggested:

  • The Tao De Ching. “I’ve been reading and reading this book since I was in my early twenties and every time I open the book I find yet another interpretation I hadn’t thought of.”
  • Adventures of a Bystander. “You look at this and say, ‘this has to be a work of fiction.'”
  • Surely You’re Joking Mr. Feynman. “This guy really had it all.”
  • Zen and the Art of Motorcycle Maintenance. “A great book.”
  • Cloud Atlas. “A tour de force.”
  • The Misbehavior of Markets. “The chapter on the destruction of the efficient market theory is worth the entire book.”
  • When Breath Becomes Air. “I’m not a crier but at the end of the book I did have tears in my eyes.”
  • For better communication, O’Shaughnessy suggested On Writing Well and How to Win Friends and Influence People.

Jim O’Shaughnessy also spoke about luck and in this last quote we circle around to where we started.

“Luck is the hand you’re dealt, talent and achievement is how you play that hand.”

Thanks for reading.


8 thoughts on “Jim O’Shaughnessy”

  1. […] Jim O’Shaughnessy said much the same, “Investing is like dieting. There are a million diet books on the market today. Most of them have simple, easy to execute plans and it is remarkable difficult to get anyone to use that simple system. It’s all emotion.” […]


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