From Jared Dillian and Adam Crawford...
Market-Beating Gains from the World’s Most Under-Appreciated Companies
Sky-high P/Es, meme stocks, NVIDIA being 8% of the S&P… this is not your grandfather’s stock market. It’s a market that’s highly imbalanced and increasingly fragile, and unless you think this time really is different, it’s time to invest in “boring” stocks that aren’t on CNBC.
The rotation into boring has already started, but most investors are still positioned for the last cycle. Enter Heartland Investor from Jared Dillian and Adam Crawford. By focusing on undervalued stocks away from the crowd, it’s delivering institutional-grade results: a 75% hit rate as of May 2026, and a win/loss ratio that keeps winners big and losers small.
Heartland Investor’s 75% Hit Rate: Proof That Fundamentals Are Back in Style
When we launched Heartland Investor in 2025, Jared made a bold prediction: The "growth at any cost" party was starting to get old, and capital would soon rotate back into durable, cash-generating businesses.
He was out-of-consensus… and right.
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At Heartland Investor, Jared and Adam teamed up to find overlooked businesses with wide moats and clean balance sheets, in market sectors not getting any headlines.
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So, how are we doing so far? Well, the great Peter Lynch once said “In this business if you’re good, you’re right six times out of ten.”
As of May 2026, here’s how Heartland Investor is stacking up:
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A 75% Hit Rate: 3 out of every 4 current stock picks in our portfolio are trading in positive territory.
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Asymmetric Gains: Our average winning position is currently up 22.6%, while our average loser is down just 5%.
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Active Performance: Across our current open stock positions, we’ve delivered an average total return of over 16%.
From a fuse company that handed subscribers a 60% gain in a handful of months to a global apparel brand up nearly 20%, we are proving you don't need to speculate on crypto or "coin-flip" tech stocks to see double-digit growth.
And we’re just getting started.
Heartland Investor Portfolio as of May, 2026
An “Incredibly Compelling Asymmetric Opportunity”
“It is an incredibly compelling asymmetric opportunity, and incredibly compelling asymmetric opportunities are what I have built my career on,” Jared wrote on November 6, 2025 to Heartland Investor subscribers. And, well, you can see for yourself in the chart…
Small cap is handily beating out the S&P.
You may be asking: Could I just buy the small cap index then? It’s a fair question, but the problem is that, for example, 40% of Russell 2000 companies are unprofitable. There is an awful lot of crap in there.
Trying to find the good stuff in the crap requires a lot of time, energy, and skill. Here’s how Heartland Investor does it:
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Dual-Lens Conviction: Technicals and sentiment from Jared. Fundamentals from Adam. Two distinct perspectives agreeing on the same idea.
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Buy, Trim, Exit Guidance: Exact buy-up-to prices, upside targets, and timely alerts.
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Moat-Score Filter: Adam’s 100-point system screens out fragile businesses so you only hold companies with durable advantages.
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A 75% “Hit Rate”: Three out of every four current stock picks trading in positive territory, with gains, including 30%, 40%, and 60% winners (as of May 2026).
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Built-In Risk Guardrails: Clear position-sizing and risk rules to keep drawdowns small.
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Ongoing Portfolio Updates: Bi-weekly notes on earnings, sector trends, and moat-score changes so you’re never caught off guard.
If the Moat’s Weak, It’s a Pass
Today, the ‘bottom’ 2,000 companies in the Russell 3000 are near their lowest price-to-earnings ratio (P/E) in over 30 years. Buried in that bargain bin are some of the most resilient, cash-rich businesses in America, trading at valuations you only see once or twice in a generation. Of course, there’s a bunch of crap in there too – unfortunately, it’s not as simple as just buying the index.
Pick right, and you could be buying the next decade’s market leaders at 1990s prices. Pick wrong, and you’re stuck with the stuff that’s small for good reason.
Warren Buffett looks for “economic moats” that protect profits like castles behind water. But most investors can’t tell if a company’s moat is real until the damage is already in the share price.
Adam Crawford, the guy Jared Dillian calls “my secret weapon,” has turned the Oracle’s idea into a 100-point, 20-metric score so you can separate the fortresses from the effing disasters, and know which deserve a place in your portfolio.
A Look Behind the Curtain of the Moat Evaluator
Even household names can be traps without a true moat:
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Microsoft Corp. (98/100)
On the surface: Tech titan with dominant software franchises and a fortress of a balance sheet.
Under the hood: Perfect scores on recurring revenue, ROIC, and market share. Evidence its moat is rock-solid.
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Campbell’s Co. (65/100)
On the surface: Steady dividends and pantry staples you trust.
Under the hood: Zero points on gross margin and limited pricing power, indicating its once-reliable moat is crumbling.
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Pfizer Inc. (61/100)
On the surface: Blue-chip pharma with blockbuster drugs and generous yield.
Under the hood: Weak customer-satisfaction and return metrics shout vulnerability under the surface.
Bottom line: the Moat Evaluator adds a key quant layer to Heartland Investor, revealing strengths and weaknesses that fundamental or technical analysis alone can miss.
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Adam runs every pick through the fundamentals gauntlet: which includes both the quantitative Moat Evaluator and his own qualitative research. Meanwhile, Jared analyzes it through his technical and sentiment lens.
If the stock under the microscope doesn’t get a “yes” from both Jared and Adam, it never reaches you in Heartland Investor.
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Sound good?
About Adam Crawford
A Missouri State grad and resident, Adam has spent the last decade turning footnotes and 10-Ks into market-beating stock ideas, proof that deep, roll-up-the-sleeves research, not fancy credentials, uncovers real opportunities. As Senior Equity Analyst at Jared Dillian Money, he built our 20-metric Moat Evaluator to quantify true competitive advantages and cash-flow powerhouse to Heartland Investor.
“Adam Crawford does thorough analysis of the companies he recommends for investment. The moat concept is critical.”
— Menno S.
Heartland Investor Subscriber
The Verdict from Heartland Investor Subscribers
“I like Adam's approach: Finding under-appreciated, solid companies with real businesses and products.”
— Mark B.
“Heartland Investor results have been very positive and research is detailed.”
— Richard F.
“I have already locked away treble the price of the subscription.”
— Jeffrey C.
“Very well thought out portfolio that includes excellent research. The proof is in the repeated hits.”
— Brent S.
“Investment returns have been excellent. Highly recommend.”
— Paul L.
“Under-the-radar gains on way less volatile companies.”
— Alan M.
A Heartland Investor Case Study: A 37.8% Return in 9 Months
In August 2025, Adam flagged Landstar System (LSTR), a trucking "matchmaker" most investors had never heard of, even though its top 100 customers had been with the company for an average of 27.7 years.
The Crawford Moat Score: 90/100. On par with Hershey and Google. Near-perfect marks on network effects (Landstar connects 78,000 truck owners with 30,000 shipping customers), customer retention (it kept 100% of its top 100 customers in 2024), and balance sheet strength (cash on hand covered long-term debt three times over).
Why the Market Missed It: Landstar is a cyclical business in an unloved industry. The freight market had been in a multi-year slump. Wall Street had moved on. The stock had drifted from $190 in late 2024 to $132 by August 2025: a 30% drawdown while the S&P 500 was making new highs.
The Dillian-Crawford Process in Action:
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Adam's lane (fundamentals): Moat score of 90, bulletproof balance sheet, $2 special dividend paid for six years running, 30% reduction in share count over 15 years
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Jared's lane (technicals and sentiment): Beaten-down cyclical near multi-year support, with sentiment so negative that even a little good news would move the stock
The Trade:
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Entered: August 19, 2025 at $132.49
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Exited: April 23, 2026 at $179.80
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Dividends collected: $2.80
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Total return: +37.8% in nine months
Why We Closed the Trade:
By April 2026, the trucking recovery thesis had played out in the share price. Investors had bid LSTR up to a point where the risk/reward no longer justified holding. “It's a cyclical business,” Adam wrote to subscribers. “I do not view Landstar as a secular growth stock that should be held for a long time. You buy shares when things are bad and sell when it looks like things are about to get better.”
What Made This a Classic Heartland Trade: A boring, cash-rich business bought when nobody wanted it and sold when Mr. Market started to take notice. A zig when others zagged.
Zig When the Headlines Zag with Heartland Investor
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Monthly Issues: A high-conviction stock pick that passes the Dillian-Crawford check, delivered with a plain-English write-up on the last Wednesday of each month.
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Proprietary 100-Point Moat Evaluator: Every stock featured in Heartland Investor will go through Adam’s Buffett-inspired grading system, built on 20 hard metrics.
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Ongoing Portfolio Intelligence: Bi-weekly notes on earnings, deals, sector shifts, and moat-score moves across the Heartland Investor portfolio, so you’re never caught off guard.
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A Strong Hit Rate: A 75% hit rate and risk management that keeps winners big and losers small.
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Heartland Kickstart Report: “This Is How We’re Going to Do It”: A step-by-step playbook for the coming rotation, plus Adam’s full stock-selection checklist, prereqs, priorities, real-world case studies, and precise sell triggers, so you know the game plan from Day 1.
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Inside Adam’s JDM Moat Evaluator Report: A behind-the-scenes look at Adam’s 100-point, 20-metric system for scoring companies, and how it shapes every pick in Heartland Investor.
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90 Day Guarantee: Try Heartland Investor for 90 days risk-free. If it’s not the right fit for you, just let us know within 90 days and we’ll refund your membership fee. Worst case, you read three months of research and get your money back. Best case, you catch a 10-year cycle from (almost) the start.
“I am very proud of Adam, and I am very proud of this newsletter. The goal here was to give people exposure to an asset class that I believed would outperform for 10+ years and then do some stock picking above and beyond that to make the returns even better. We have very satisfied customers so far. And hey, we want you to be a customer. Hope you can join us.”
— Jared Dillian, co-founder, Jared Dillian Money
Questions
Answered
Still stuck?
Email support@jareddillianmoney.com and a real human will reply.
…just buy a small-cap value ETF? Because 40% of the Russell 2000 is unprofitable. The index is a haystack with a few needles in it. Heartland Investor is the needles, hand-picked.
…a financial advisor? Because a typical advisor charges you 1% of assets to put you in the same large-cap index funds as everyone else. They aren't reading 10-Ks to figure out if the moat is intact.
…another newsletter? Most newsletters pitch you on AI, crypto, or "the next NVIDIA." Heartland Investor pitches you on companies you've never heard of, that pay real cash flows, in industries you'd find on a state fair vendor list. Different game.Jared is hands-on in every issue. Think of him as the coach in the press box: Adam calls the plays and Jared makes sure each pick fits the macro and technical side before each issue is released.
Adam has been Jared’s senior equity analyst for almost a decade. Because of Adam’s deep fundamental analysis skills and his bias toward finding bargain, cash-rich businesses, Jared asked him to take more credit for his work and lead Heartland Investor. Over the past decade, Adam’s built a reputation for finding wide-moat, cash-generating companies which don’t get thrown around by volatility.
Yup – if you’re interested in fundamentals rather than headline stocks. In every issue, Adam guides you step-by-step through the moat-driven, valuation-first framework he’s refined for Jared over the past decade. Even if you’re just building your portfolio, you’ll learn a repeatable system for identifying durable, undervalued companies that have significant upside.
Definitely not. Heartland Investor is designed for mid- to long-term investors who, as Heartland subscriber Mark B. put it, want to “find under-appreciated, solid companies with real businesses and products.”
Not at all. All 100-point moat grades and timeline charts are fully integrated into each issue—no downloads, no plug-ins or downloads needed.
Every ticker we cover is liquid, U.S.-listed, and available on major brokerages, just like any other stock you trade.
Sure do - every pick comes with a buy-up-to price, an upside target, a suggested weighting, and updates when it’s time to trim or exit.
You’ll get an in-depth issue on the last Wednesday of each month, plus portfolio news and updates bi-weekly.
Everything’s right there in our online subscriber portal (mobile- and tablet-friendly). Missed an edition? It’s always waiting in the archives.
Just let us know within your first 90 days, and we’ll refund 100% of your subscription, no questions asked.
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.
About Heartland Investor
Heartland Investor was built in 2025 to help Jared Dillian Money subscribers benefit from what Jared saw as the coming renaissance of small cap value – a sector that had underperformed for decades. Jared brings sentiment and technical analysis, while Adam – his long-time analyst – delivers deep fundamental analysis. Together, they bring Heartland Investor subscribers undervalued stocks with strong balance sheets and in stable industries.
Despite small cap value’s reputation as volatile, Adam Crawford’s moat evaluator and Jared’s “get rich slow” mentality means that Heartland Investor’s portfolio won’t keep you up at night. In a landscape of tech and growth focused services, Heartland Investor stands out as a genuine oddity – a newsletter service focusing on fundamentals that delivers market-beating returns.