Not Exactly What You Expect of a Finance Guy
Jared Dillian is a former Wall Street trader, a bestselling author, DJ, and MFA graduate. He is all of these things, but none of them really explain Jared Dillian.
What they do explain is a career built on curiosity, tenacity, and an obsession with probabilities. For more than two decades, Jared has questioned conventional wisdom, decoded market sentiment, and explored the messy intersection of investing, risk, and human behavior.
As seen in
The Man Behind Jared Dillian Money
Jared is one of the industry’s most original, entertaining, contrarian voices. He is a master of market psychology, has been called the “Dr. House” of trading, and he has a following ranging from casual investors to professional traders and hedge fund managers.
He has never been particularly good at staying in one lane. At school, he split his time between electronic music and classical training in piano and organ. He studied Mathematics and Computer Science at the U.S. Coast Guard Academy, and earned an MBA from the University of San Francisco. At the same time, he served as an officer in the Coast Guard and got a part-time job on the floor of the Pacific Coast Options Exchange.
He later became head of the ETFs trading desk at Lehman Brothers while writing The Daily Dirtnap, an underground market letter that quickly developed a loyal following among professional investors. What started as one market newsletter has grown into investment research services, masterclasses, bestselling books, and a community of thousands of investors at Jared Dillian Money. Along the way, he somehow found the time to earn an MFA in Creative Writing, DJ professionally, and rescue a troupe of cats.
“If you’re not going forward, if you’re not constantly challenging yourself, you’re going backwards. Never get comfortable. Never get complacent. The most important decision you will ever make in your life is what to do with the next 24 hours.”
— Jared Dillian
100k
Readers
20k
Subscribers
4
Investment Services
3
Masterclasses
Jared’s “Rules” of Trading
Some finance people like to pretend markets are governed by elegant theories. Jared knows they’re governed by human behavior, and human behavior is gloriously irrational. There’s a reason he’s known as “the sentiment guy,” and the “Dr. House of trading.”
There’s a reason he believes that the insane trade is usually the right trade… that more information is usually worse than less information… that the goal of investing is to smooth out the volatility in your life. There’s a reason he goes against consensus… that nothing satisfies him more than making 30% when the market is in the tank… and that he’s uncomfortable in crowded trades. It all comes back to people being irrational creatures.
“The one thing you start to figure out when you are in your third decade is that there are no rules,” Jared says. “You do what works. You do more of what works and less of what doesn’t. And then you have the sense to get out before the top.”
That said… after almost 30 years of trading, he does have some rules. Kind of. Here’s Jared:
My Number One Rule of Trading:
1) I have no rules of trading.
But… I do have guidelines:
2) I don’t make a habit of adding to losing positions.
3) I do make a habit of adding to winning positions.
4) But I also often don’t do those things.
5) Sometimes I buy the most horrible looking charts in the world. And I have a pretty good track record of being right in those situations.
6) I always try to confront my own biases.
7) I don’t have any stop losses, because I believe that all stops are meant to be elected.
8) Most of the time I have an idea of where I will close a losing position. Sometimes I don’t.
9) I have found that most people who are religious about cutting losers are also pretty good about cutting winners.
10) You can tolerate a few screw-ups here and there if you play for the really big win.
11) But most people don’t play for the big win. You have to pick up a lot of nickels to become a millionaire. All it takes is for me to have one really good idea.
12) If you want to read more about my trading philosophy, I pretty much agree with Stan Druckenmiller on everything. Especially when it comes to diversification. Or non-diversification, as it were.
Speed Round with Jared Dillian
The average investor’s biggest mistake is...
Overconfidence.
The most dangerous words in investing are…
“Give me some of those SAFE index funds.”
The most dangerous personality trait in investing is…
Ego.
The most useful personality trait in investing is…
Humility.
What’s one of your pet peeves about financial media?
They think they are experts in everything.
Most financial media is…
Useful for trading against.
What are some of your unpopular opinions about markets or money?
You don’t need math. You don’t need to read the news.
What are you bad at that people assume you’re good at?
Stock Picking.
What are you good at that that a lot of people don't know?
Thinking.
Most people don’t need more information, they need…
More game theory.
What’s the best piece of investing advice you ever received?
The key to life is liquid net worth.
What’s your favorite money movie of all time?
25th Hour. The trading floor scene in that is five stars.
What’s your biggest guilty pleasure?
Sitting on the couch with my cats writing something.
What kind of investor tends to stick with you long term?
Someone who loves markets, but also someone who realizes there is more to life than markets. We’re on a journey together.
Where to Start
If you've made it this far, you've probably already worked out whether Jared is your kind of investor and thinker. Here's where most people begin:
Investment Research
Research, portfolios, and market commentary grounded in probability, risk management, and independent thinking. Learn More
Masterclasses
Deep-dive masterclasses that simplify fiendishly complex mathematical subjects for the investor who wants to understand what they’re trading. Learn More
Market Nonsense
A free weekly newsletter for people who enjoy questioning consensus and finding opportunity in absurdity. Learn More
Michael Kane
Marketing
Rachel Almeida
Marketing
Jo-Ann Ring
Operations
Conor Cook
Marketing
Samantha Dube
Communications
Cameron Hagler
Managing Editor
Cameron works alongside Jared to edit and publish everything from investment research to Masterclasses and Market Nonsense. Around here, we call him the ‘Chief Wrangler.’ Nothing gets published without his eyes on it first.
Adam Crawford
Senior Investment Analyst
Adam leads the research behind Heartland Investor and brings a fundamental, business-first approach to stock analysis. He’s also what Jared calls his “secret weapon” in Street Freak and The Strategic Portfolio.
Who's Doing the Work
Why Readers Stick With Jared Year After Year
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“I’ve been an avid reader of Jared Dillian for 20 years... He writes for his readers and his readers only, combining deep investing experience with an authentic, truly independent voice that has become an indispensable perspective for me and so many others.”
— Ben H.
“You are sacrilegious and contrarian, in a good way”
— Charles G.
“Very well thought-out portfolio that includes excellent research. The proof is in the repeated hits.”
— Brent S.
“Not only have you educated me, you’ve entertained me. And made me money that I wouldn’t otherwise have. From the working stiff hiding under a rock, thank you. You’re money well spent.”
— Benjamin V.
“Thank you for being one of the best voices out there today. In my long career I place you with Art Cashin and the young James Grant: observant, thought provoking, and entertaining.”
— Peter M.
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“Your blend of thoughtful and experienced (longer term) trading suggestions, human interest wisdom, and impactful diversification (e.g. a book writer as well) are exceptional. Your transparency is so damn authentic. If you could put that in a pill and distribute the world would be better off to be sure.”
— Stan B.
“I’m convinced you are a mythical anomaly. I’ve been following you for years now, and I only get more impressed over time. The calls you make… the timing… the instinct… the intuition… Telling you, it’s different man. On another level.”
— Joshua B.
“I absolutely love Jared Dillian. He is brilliant, uncommonly honest, funny, and extremely knowledgeable. What a gift he is!”
— Demi W.
“An alternative to the cookie cutter approach by most investment letters.”
— Joel K.
“I absolutely love Jared Dillian. He is brilliant, uncommonly honest, funny, and extremely knowledgeable. What a gift he is!”
— Demi W.
Questions,
Answered.
Still stuck?
Email support@jareddillianmoney.com and a real human will reply.
Yeah, but not for the sake of it. He's interested in understanding why the crowd believes what it believes, and whether it's right. Sometimes that means agreeing with consensus, but more often, it means asking uncomfortable questions and going in a different direction from the crowd.
Definitely not. In fact, he'd probably worry if they did. Jared's goal isn't to build an echo chamber. It's to challenge the way people think about markets, even if they end up reaching a different conclusion.
Market Nonsense is free, it comes out weekly, and it's the fastest way to get a feel for how Jared thinks before you pay for anything. If you’re ready to go deeper, here’s a good place to start.
He ran the ETF trading desk at Lehman, where he moved more than $1 trillion. Was he a good trader? Here’s his answer: “I was an above average trader. I had strengths and weaknesses. I tried to be free of bias, but I wasn't. I tried to be rational, but I wasn't always. But I think I was better than most. I was aware of my own limitations.”
He’s not blindly one way or the other. His job is to see markets as they are, not as he wants them to be. However, he does “always, always think about the risk of ruin,” he says. “The ‘number go up’ attitude espoused by the index fund simpletons is highly simplistic.”
We have no clue. Let us know if you find out.
Six: Wendy, Vesper, Tars, Xenia, Stripe, and Yellow. They have their own Cat Wing at The Daily Dirtnap World HQ in South Carolina. Yes, it’s a lot of cats. Even as a toddler, Jared didn’t play with bricks and blocks—he played with stuffed toy cats.
You can take a look at our full FAQ here, or drop us a line at at support@jareddillianmoney.com.
The Guy Outside the Markets
Spend long enough around finance and you'd be forgiven for thinking traders only read finance books and read Bloomberg all day. Jared has never really fit that stereotype. He's written novels, short stories, and essay collections, and earned an MFA in Creative Writing. Music has been a constant too, from childhood piano lessons to DJing professionally.
Behind it all is a belief in stochasticity, the quality of being random, unpredictable, and probabilistic.
“Life is stochastic. Markets are stochastic. Music is stochastic,” he says. “You can't control every outcome—but you can build systems that work through uncertainty.”