We Put 5 “Buffett Wannabes” Through the Boss Fight — And the Winner Wasn’t Who You Think 🤔

Every few weeks, Wall Street discovers “the next Berkshire Hathaway.”

The pitch usually comes with delicious ingredients:

✅ Founding family still in control
✅ Intrinsic value up 1,000%+
✅ 25%+ annual growth
✅ Biggest discount in 20 years
✅ Management buying back its own shares because they’re “too cheap”

At this point, all we need is a thunderclap, a bald eagle and Warren Buffett appearing behind a curtain whispering:

“Buy now.” 😂

But here’s the problem.

Those numbers may each be true under carefully chosen definitions or time periods. That doesn't mean one company necessarily passes all five tests simultaneously.

So instead of hunting for the secret ticker behind a newsletter paywall, I treated the whole thing like a video-game boss fight:

Find the weak point. Attack it. Move to the next candidate. Repeat.

And something much more useful emerged.

🥊 THE FIVE-COMPANY BERKSHIRE GAUNTLET

And there’s an important sixth name lurking outside the US:

Constellation Software.

Its founder Mark Leonard helped create one of the greatest software-compounding machines around, but it doesn't cleanly satisfy the “founding family still running the show” requirement. So I would study it as a Berkshire blueprint, not force it into the final US shortlist.

🥇 LOEWS: THE TEASER-MATCH CHAMPION

If the question is:

My answer is Loews.

The Tisch family has controlled the company for generations, while Loews owns a collection of businesses including CNA Financial, Boardwalk Pipelines and Loews Hotels.

But its real superpower isn't glamour.

It's capital allocation.

Loews repurchased 8.9 million shares for $782 million in 2025, followed by another 0.3 million shares for $31 million in Q1 2026. Book value per share reached $90.90 at March 31, 2026.

That's important because a buyback only creates value when management buys below what it believes the shares are worth.

Otherwise, it's just corporate shopping.

Weak point: Loews isn't a 25%-a-year growth monster.

And that's exactly why I would not claim it passes every promotional checkbox.

Its attraction is different:

family stewardship + asset value + disciplined buybacks + patience.

🥈 HEICO: THE COMPOUNDING MACHINE

If the question becomes:

HEICO becomes extremely difficult to ignore.

The Mendelson family remains deeply invested in the company, with substantial family holdings disclosed in its 2026 proxy.

HEICO has built an extraordinary acquisition machine around aerospace, defense and electronic components.

Its playbook is simple:

Buy niche businesses → keep good managers → avoid unnecessary interference → reinvest → repeat.

That's very Berkshire-like.

But here's the boss fight:

VALUATION.

HEICO is often priced like the market already knows it's brilliant.

And if you pay a heroic price for a wonderful business, you may discover that your biggest enemy isn't the business.

It's the multiple you paid.

🥉 MARKEL: THE OBVIOUS “BABY BERKSHIRE”

Markel may be the easiest comparison.

Insurance.

Investment portfolio.

Operating businesses.

Long-term capital allocation.

Share repurchases.

Sound familiar?

Markel's own 2025 shareholder letter reported that its estimated intrinsic value per share increased 12% in 2025, compounded at 15% annually over five years and 16% since its IPO.

Those are excellent numbers.

But they also expose one of the biggest problems with the teaser:

25% isn't a normal requirement for a great compounder.

If 15–16% can compound for decades, that's already enormously powerful.

So don't throw Markel away because it doesn't hit an arbitrary marketing number.

🧩 IAC: THE MESSY TREASURE CHEST

IAC is the unconventional candidate.

Barry Diller and members of his family collectively controlled approximately 46% of IAC's voting power as of February 2026.

IAC's game is different:

Build → acquire → grow → spin off → recycle capital.

It also repurchased shares aggressively: between February 3 and May 1, 2026, IAC bought back approximately 2.9 million shares for $111.3 million.

That makes IAC interesting whenever the market applies a large holding-company discount.

But remember:

A discount can mean opportunity.

It can also mean the market knows something you don't.

That distinction is where the real research begins.

🏗️ BOSTON OMAHA: THE BABY BERKSHIRE WILDCARD

Boston Omaha is the intriguing early-stage candidate.

Its businesses span outdoor advertising, broadband, surety insurance and asset management.

And management is actually buying shares: it repurchased 375,286 Class A shares for $4.8 million in Q1 2026, after repurchasing 444,753 shares during 2025.

There is also a $30 million repurchase authorization running through December 2026.

But don't confuse:

“small Berkshire-like company”

with

“Berkshire-in-training guaranteed to succeed.”

It has far less history and scale.

That makes it potentially interesting.

It also makes it much riskier.

🎯 SO WHO ACTUALLY WINS?

Here's my final verdict:

Best match for the mystery teaser: LOEWS

Best operating compounder: HEICO

Closest Berkshire structure: MARKEL

Most interesting early-stage wildcard: BOSTON OMAHA

Most unconventional capital allocator: IAC

And that's a much better answer than pretending one stock magically passes every checkbox.

Because intrinsic value isn't a number carved into Buffett's desk.

It is an estimate.

Different assumptions produce different values.

So the real question isn't:

It's:

Now we're investing.

✅ THE MINI-BERKSHIRE CHECKLIST

Before buying any supposed compounder, score it from 1–5:

Don't buy because it scores 10/10.

Buy only when you understand why the market is mispricing it — and what could prove you wrong.

For trading, this same framework becomes useful as a watchlist filter: identify high-quality businesses first, then use valuation, market regime, price trends and position sizing to decide when to enter rather than chasing whatever stock is currently screaming loudest.

☕ WHERE WEALTH BUILDER FITS

Retail investors don't usually suffer from too few ideas. They suffer from too many ideas, too much noise and too little process.

“Next Berkshire” pitches amplify that problem by turning complicated valuation questions into seductive headlines. Newsletters such as Wealth Builder, passive-income research and investing frameworks can help solve this by converting noisy stories into checklists, watchlists and repeatable decision processes.

The goal isn't to outsource your brain or blindly follow a ticker. It's to help you ask better questions, compare opportunities, understand valuation and build wealth systematically. Because the biggest investing advantage isn't knowing tomorrow's hot stock.

It's developing a process that keeps you from doing stupid things today. 😄

🚀 THE REAL BERKSHIRE SECRET

Maybe the next Berkshire isn't HEICO.

Maybe it's Markel.

Maybe Loews quietly compounds for another 20 years.

Maybe Boston Omaha surprises everyone.

Maybe IAC unlocks value nobody expects.

Or maybe none of them becomes Berkshire.

That's okay.

Because the real lesson isn't finding the next Buffett.

It's learning to recognize:

great businesses + great managers + sensible prices + long time horizons.

You don't need to predict the winner.

You need to build a process capable of finding winners repeatedly.

And if you enjoy discovering unconventional investing ideas, passive-income strategies, compounders and practical wealth-building frameworks, explore other like-minded newsletters here.

Because sometimes the best investment isn't hiding.

The market is just looking somewhere else. 👀

🔥 FINAL 3 WORDS

FIND. FILTER. COMPOUND.

📚 Sources & Notes

Primary company sources: Loews 2025 results and 2026 quarterly disclosures; Markel Group 2025 Shareholder Letter; HEICO 2026 Proxy Statement; Boston Omaha 2025 annual results and 2026 Q1 results; IAC 2025 Annual Report and 2026 Q1 disclosures.

CAGR = Compound Annual Growth Rate, the annualized rate at which something grows over a period.

FCF = Free Cash Flow, the cash a company generates after necessary capital expenditures.

IPO = Initial Public Offering, when a company first lists its shares publicly.

ROIC = Return on Invested Capital, a measure of how efficiently a business generates returns from the capital invested in it.

SOTP = Sum-of-the-Parts valuation, where individual businesses or assets are valued separately and then combined.

NAV = Net Asset Value, broadly the estimated value of assets minus liabilities.

Intrinsic value = an estimate of what a business is worth based on its assets, cash flows, earnings power and other assumptions. It is an estimate, not a guaranteed price.

PMA = Parts Manufacturer Approval, an approval issued by the U.S. Federal Aviation Administration for certain aircraft replacement parts; this is relevant to HEICO's aerospace business.

This newsletter is for education and idea-sharing only. Nothing here constitutes personalized financial advice or a recommendation to buy or sell any stock, exchange-traded fund (ETF) or other asset. Valuations and business conditions change. Readers should conduct their own due diligence and consult multiple independent sources before making investment decisions.

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