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On this episode of the Intentional Investor, Matt Zeigler welcomes legendary investor and entrepreneur Jim O’Shaughnessy. Jim shares fascinating stories from his childhood, including memories of his influential grandfather, his early interest in magic, and how rejection shaped his mindset. The discussion covers Jim’s journey into investing, his thoughts on education and critical thinking, and his experiences on Wall Street. Jim offers insights on topics like the power of journaling, the importance of empiricism, and his excitement for AI and new technologies.
What do you ask the man who has been asked every podcast question?
Jim O’Shaughnessy (aka James, aka JP, aka - just peep the intro) has recorded over 200+ of his own Infinite Loops episodes (I’ve written about multiple episodes here), not to mention he’s made countless other appearances everywhere else (I tried to count and gave up, there are MANY), and suffice it to say, as I did my prep routine for this conversation, I felt the all too familiar sting of… I got nothing. It’s all been done. Even the obscure stuff like when his grandfather got kicked out of college…! But.
Then I remembered the number one rule, for any of these conversations/interviews, for everything that goes into my Personal Archive: you’re the mirror, this is your reflection, f* everything else.**
So the notes got chucked.
The standard Intentional Investor areas of interest were all that matters. I knew I wanted to talk to Jim about his grandfather and his grandkids. I knew I had a funny story from one of his books on my own bookshelf to tell him. I knew if I could just wind him up, especially if I could get him laughing, he wouldn’t want to shut up. If a person can take everything super seriously and retain the ability to get stupid silly, you know I’m going to lean into that. I can reflect that all day long. Full reflection mode was activated, from the moment we pressed record.
I heard some fresh stories here, I think you will too. Plus, plenty of other ones, especially about his youth got fleshed out further than I’d ever heard them. I’ll be awaiting word from Ed Williams, Liberty (Michael G.R.), and Dylano - or anybody else from the OSV camp - if I broke any news. I doubt it, but the point of reflecting these stories, it stands.
Most of all, getting to drill into Jim as a 17-year-old magician, doing mentalist tricks until a woman refused to believe he wasn’t the real deal, I won’t be forgetting that story. It might just explain his passions and trajectory better than any other tale I’ve ever heard him tell. This conversation really cemented its impact in my mind.
Here it is or get it on your podcast player of choice, and here’s to the 6 more parts we’d require if we can ever hope to cover the rest of his incredible life’s experiences (so far!) - Jim O’Shaughnessy is an Intentional Investor, I have proof, it’s live on the Epsilon Theory YouTube channel:
Jim is one of my favorite posters on X.
I really enjoyed the discussion, always great to hear what Jim has to say. I also found the discussion about dispelling doomerism funny in that my dad - also Jim - uses the same exact phrase “winners of the cosmic lottery” to describe anyone born in the post-war United States. Sometimes it can be helpful to take a big step back from the doom&gloom of the waters we swim in and remember how lucky we are.
Griffin,
Thank you for pointing this out for me. It’s taken me most of my life to figure this out. Doh!
boomer jim
Only Matt Ziegler can do justice interviewing Jim O’Shaughnessy.
I laughed tears of joy the whole way through.
Here’s what really hit me.
“Children are voraciously curious. They want to learn.“ Why, why, why,…are we there yet??? His father and grandfather encouraged that. Montessori schooling. His understanding the power of magic at a young age for nudging others into false beliefs.
My parents always said this about me:“You asked so many questions as a child!” Then they would add, “Too many questions.”
What I’ve previously opined on Epsilon was that I stopped asking questions verbally but they continued silently for the most of my life.
Luckily as a stem major in college, I took as an “easy” elective, a course on the history of science which instilled in me the rest of my life what Jim O’s said, “Science, not in a stem sense but in an enlightenment sense. (Scientific method)
What I’m blessed with now is a vocabulary and humility that that the young me could not have. It’s all about the fire hose of questions pouring out.
Wisdom or Delusions of Grandeur? I don’t care, I have nothing to lose. I’m free (to a point of course).
I used to advise my grandchildren on the John Wayne method of speaking:
“You talk low……… You talk slow……. And you don’t say very much.”
Now, I’m adding the Matt Ziegler and Jim O’Shaughnessy method of speaking: Start with a joyful smile connect to the funny bone (not sure where that is, it may be the humerus) with comments that nudge an answer that they feel they came up with it on their own. Immediately reply, “That’s a good idea.”
“Won’t you be my neighbor”
-Fred Rogers.
jim
I love that the answers to doomerism include both being more realistic and woo-ish at the same time (look at the results here, very little doom, AND maybe there’s a little more magic at play, so lean into it!)
Thanks for sharing this Griffin, it made me smile to read.
It’s never too late to speak up Jim, glad you refound your voice. It was a very good idea.
“You’ve made this day a special day, by just your being you. There’s no person in the world like you. And I like you just the way you are.”