Escaping the Caterpillar Pillar with Jared Dillian

Hello everyone,

I had the pleasure of chatting with Jared Dillian, author of The Daily Dirtnap and We're Gonna Get Those Bastards, about his new book Those Bastards. Years ago, I read his book Street Freak and I fondly remembered his wit, candor, depth of introspection, and keen eye for the antics of markets.

Those Bastards is a collection of Jared’s essays on life, death, meaning, friendship, marriage, luck, ambition, suicide, and much in between (including a few great bits on markets and finance). It’s refreshingly honest and fun and led to a lot of reflection.

In our conversation we touched on writing and finding your voice, escaping the caterpillar pillar, how markets are ruled by fear, being the guy who knows a guy, mental health and the power of writing, making meaningful memories, the right temperament for markets, why people don’t change, and why you should ask people if they are lucky.

A few highlights from the conversation:

A lot of people think that markets sort of oscillate between fear and greed, right? But it really isn't fear and greed. It's fear and fear. It's all fear, right? Greed is fear of not getting something that you want. So working in the markets is, if you have any background in psychology, it's a very depressing place because the markets are filled with fearful people, like acting based on fear. But the thing is that it's very predictable. People behave in very predictable ways. So that's been my thesis about markets all along.

I like to know lots and lots of people. Now, having a newsletter has been the perfect way to do that because a lot of times if I have a question about like air conditioning, I can put it in my newsletter and I get 20 responses. I know somebody who owns an HVAC company. I know people in all different kinds of industries and if I ever need help, I can reach out to them. I like to call that having a big world. I like to have a big world. I like to know lots of people. That's just my personal philosophy.

I learned that people had similar experiences, they just would never talk about it. There are things you cannot talk about in polite conversation, but you can do it with words, you can do it on the page and you can bring people into this world. And that's the magic of it. My Substack is like a safe space for people to read this stuff and think about these issues, really the only place you can talk about 'em is with a therapist or something like that.

The top five memories piece came from the show Lost. There's a character named Charlie and he has a premonition that he's going to die. He knows exactly when it's going to happen. And so he sits down and he starts thinking of his top five memories of all time.

And it got me thinking like, that's actually a really good exercise. Like what are your top five memories of all time? I think one of mine was marching band in high school. One of mine was DJing. Really your goal in life should be to make more of those top five memories and keep doing that over and over again.

I had a trade that made 15 million bucks. That was a great trade. But it doesn't make my list of top five memories, because top five memories are about relationships and achievement and things like that. Lehman was a great place to work, but ultimately that's not what we're here on earth for.