Gain From Disorder With Street Freak
Jared Dillian's Investing Services
Jared’s Street Freak is an aggressive stock-picking service for investors who are not bashful about taking risk – but aren’t the “put it all on black” type either. Think outsized gains, downside protection, and not a consensus trade in sight.
“There are tortoise portfolios (get rich slowly) and hare portfolios (get rich quickly but risk losing it all), and then there is Street Freak. We try to make a lot of money at Street Freak, but we do it while also focusing a lot on risk management. It’s an unusual combination, probably because it’s so hard to do.
My goal with Street Freak is to underperform a little bit in good times and outperform massively in bad times. To me, there is nothing more satisfying than making 30% when the market is in the tank and everyone is getting killed.
And for the last 10 years, we’ve been very good at that in Street Freak. I tend to build portfolios that gain from disorder. I have scars on my knuckles and cauliflower ears from trading through the Tech Crash and the Great Financial Crisis, and so I am a crisis trader at heart.
If making money while markets are falling apart sounds good to you, I think you’ll like it here.”
— Jared Dillian
“I Am a Crisis Trader at Heart”
Overview:
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Investment Risk: Medium
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12 monthly newsletter issues
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2 portfolio updates a month
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Trade Alerts as needed
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Immediate access to the portfolio
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Access to the archives
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90-Day Money-Back Guarantee
Street Freak is Jared’s most aggressive service. The portfolio is made up of positions that reflect his most high-conviction ideas, and it’s mostly long, but there are some shorts. Typically, it is about 80% long and 20% short, though it can be as much as 40% short, depending on the situation.
There is also the occasional index hedge. It’s semi-diversified across sectors, though there are big sector bets. There is definitely a value bent, with a focus on dividends, and there is market timing. And in the search for high returns, it stays away from stuff like FANG and the AI trade.
But even though it’s aggressive, that’s cushioned with savvy risk management. “When I pick stocks, I am not just picking a stock that I like,” Jared says. “I am thinking about how it fits into the larger context of the portfolio, and how it reduces risk. Our success at Street Freak isn’t about one idea or call. It’s about discipline and ironing out volatility. Drawdowns are the enemy of investors. If you have $2 million, you don’t want to go to $1 million on the way to $4 million. You will be miserable. You will have a heart attack.”
Aggressive, But Never Reckless
STREET FREAK
+37.7%
S&P 500
+16.4%
S&P 500 EW
+8.8%
And the most recent full-year results: In 2025, the Street Freak portfolio finished up 37.7%, while the S&P 500 and the S&P 500 Equal Weight indices were up 16.4% and 8.8%, respectively.
2025 Full-Year Results
A Look Under the Hood at Those Returns
As of July 2026, there are 16 open positions in the Street Freak portfolio, which is about the average number in there over time. 12 of those positions are picks in Jared’s two highest conviction themes – which is how Street Freak normally works.
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To give you an idea of Street Freak without annoying subscribers by sharing current positions, here are the positions we’ve closed out so far in 2026:
Bancolombia SA
+94.1%
HDFC Bank
+7.9%
Jack Henry &
Associates
-28.8%
Banco de Chile
+39.4%
American Electric
Power Company
+51%
Suncor Energy
+68.2%
Bancolombia SA
+16.4%
HDFC Bank
+7.9%
Jack Henry & Associates
-28.8%
Banco de Chile
+39.4%
American Electric Power Company
+51%
Suncor Energy
+68.2%
So, Is Street Freak a Good Fit for You?
Probably Yes, If...
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You get excited when everyone else is panicking.
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You don't mind looking a bit crazy if the thesis is right.
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You'd rather thrive in a crash than win a bull-market popularity contest.
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You understand that avoiding big losses is half the battle.
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You enjoy buying things the market has given up on… or isn’t thinking about yet.
Maybe Not, If...
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You think the best investment is whatever CNBC is talking about.
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You need constant reassurance that your portfolio is "normal."
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You think "risk management" is something other people worry about.
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You'd rather own the Magnificent Seven than spend time looking for the next opportunity.
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You want a set-and-forget portfolio you barely have to think about.
Why Should I Listen to This Guy?
Jared Dillian didn't learn about risk from a textbook. He learned it on Wall Street, running Lehman Brothers' ETF trading desk through one of the most chaotic periods in modern financial history. And before that, he got his first market scars at the Pacific Coast Stock Exchange.
He has traded through the dot-com crash, the Global Financial Crisis, COVID, inflation, and just about every other variety of market panic you can think of. Those experiences shaped the way he invests today.
Jared calls himself “a crisis trader at heart.” While other investors are trying to survive disorder, he's looking for ways to profit from it. And that’s why Street Freak’s portfolio is built to outperform when markets are falling apart.
Managing the Street Freak portfolio, Jared thinks constantly about position sizing, downside protection, sector exposure, hedges, and how every holding changes the risk profile of the portfolio. Street Freak is aggressive by design, but recklessness has never been part of the strategy.
Also, he literally wrote the book: Street Freak: Money & Madness at Lehman Brothers.
“Entertaining way to actively learn more about investing, especially for someone who also has a regular day job outside of the investment markets.”
— Jamison N.
“Outside the box thinking with outside the box stock picks. Not all of the picks work (true of any letter) but the ones that do usually work REALLY well.”
— John Mc I.
“Your recommendation was sensational. I sold it last week as 3-baggers and 4-baggers, again on your recommendation. You are the best.”
— Francis W.
“I absolutely love Jared Dillian. He is brilliant, uncommonly honest, funny, and extremely knowledgeable. What a gift he is!”
— Demi W.
“Street Freak is an unconventional newsletter in that you will find research and recommendations outside of the usual "safe" stock picks by legacy advisors.”
— Joe S.
“Original advice, well-constructed portfolio, unconventional thinking, smart risk management… Honest and unfiltered perspective.”
— Daniel C.
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“Good insights on market sentiment and a check on popular news cycle that forces you to think. Actionable specific investment recommendations, but also a thought process that is communicated in a way that sparks other ideas you've been thinking about.”
— Nate K.
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“It offers a balanced portfolio outside heavily concentrated sectors while also recognizing and employing valuable investment themes before they become popular. It offers a good combination of advanced investment guidance without significant time commitment.”
— Dan B.
“Like Goldilocks and the porridge, the portfolio doesn’t run too hot, doesn't run too cold... It runs just right, and I'm eatin it up!”
— Michael R.
“I've been meaning to thank you for saving my portfolio.”
— Jim K.
What Street Freaks Think
STREET
Freak.
Most investors spend market crashes watching their portfolios shrink and wondering when the pain will end. Street Freak is built on a different idea: that periods of fear, forced selling, and general panic create some of the best opportunities you'll ever get.
That's why Jared has built a portfolio that gains from disorder. If that sounds like the way you'd like to invest, Street Freak is $2,495 a year. That’s not cheap, but Street Freak subscribers say it’s worth every penny – and you can try it out risk-free for 90 days. (Remember, we’re all about risk management around here.)
Here's what's included in your membership:
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12 Monthly Issues: Every month you'll get Jared's macro outlook, The Month in Charts, and a full portfolio update explaining what he's doing and why.
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3 Portfolio Briefings a Month: Separate updates focused entirely on the Street Freak portfolio, so you always know where things stand.
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Trade Alerts, As Needed: When Jared opens, closes, trims, or adds to a position, you'll know about it.
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90-Day Money-Back Guarantee: Try Street Freak for yourself. If it isn't the right fit, let us know within 90 days for a full refund.
Start Looking Forward to Bear Markets
“A lot of people do this mental accounting where they say ‘I've got my safe money and my aggressive money’. Street Freak is for aggressive money. With higher risk and conviction, you get a much higher potential upside on your returns.”
— Jared Dillian, co-founder Jared Dillian Money
Questions,
Answered.
Still stuck?
Email support@jareddillianmoney.com and a real human will reply.
Nope. Stock picks are the output, not the product. Street Freak is a complete portfolio built around Jared's highest-conviction themes, with every position chosen in the context of the others. Risk management is just as important as finding the next big winner.
Plenty of subscribers do, but many use Street Freak as an idea generator. They might own a handful of positions, borrow a theme, or simply use Jared's research to challenge their own thinking. Another common strategy is allocating a small percentage of your portfolio to Street Freak, and a larger percentage to the Strategic Portfolio.
Absolutely not. This is for intermediate and experienced investors who want a more aggressive approach to mid- to long-term investing.
Yes, provided you're comfortable with a more hands-on approach than a buy-and-forget portfolio. Street Freak is for investors who enjoy following markets, thinking independently, and acting when opportunities arise.
Street Freak comes from Jared’s memoir, Street Freak: Money and Madness at Lehman Brothers. It was Businessweek's #1 general business book in 2011. The name fits his style and philosophy perfectly— he takes more risks here than he does in his other services. It's also a great book.
You can take a look at our full FAQ here, or drop us a line at support@jareddillianmoney.com.
About Jared Dillian Money
Jared Dillian Money is a financial research and education company focused on helping thoughtful investors act decisively and manage risk like professionals. Investors don’t want more noise – they want clear thinking from someone they can trust. Not only that, they want to develop their own thinking, which is why Jared “teaches how to fish.”
Jared Dillian Money offers a range of services, including Street Freak, The Strategic Portfolio, and The Daily Dirtnap, and a growing library of Masterclasses. What they have in common is straight-talking financial wisdom - the kind that comes from 25+ years of trading experience, deep market insight, and a touch of cynicism.
Everything at Jared Dillian Money is designed to help you invest smarter, stay grounded, and avoid blowing yourself up. Whether you’re trading your own account or managing money for others, this is a place for people who take markets seriously… and aren’t afraid to take the other side of the trade.
