To The Moon

Investment gurus build their reputations over decades, but markets have a way of reminding everyone that even the most celebrated investors can be wrong, or right at the wrong time.

The realities facing 2 of the world's most scrutinized investment vehicles - (a) —Bill Ackman’s $Pershing Square USA, Ltd.(PSUS)$ and (b) Warren Buffett’s $Berkshire Hathaway(BRK.B)$, serve as a valid case in point that when it comes to investing, even gurus can be wronged sometimes.

This comes about, even with (a) decades of experience, (b) deep research benches, and (c) billions of dollars at their disposal, the sharpest minds on Wall Street are susceptible to:

• Miscalculating market trajectories.

• Mis-timing exits.

• Enduring prolonged periods of stark under-performance.

Faltering Streak

Bill Ackman is having a difficult year not in theory, but in a concrete set of positions where his concentrated, high‑conviction style has cut the wrong way.

As a result, his net worth has fallen sharply from its peak earlier this year.

Math behind the unforgiving slump:

• Pershing Square data shows that the company's portfolio has dropped by -9.3% this year.

• In contrast, the S&P 500 and Nasdaq 100 indices have jumped by +9.6% and +13.4% in this period.

The dramatic divergence highlights how quickly an investment thesis can turn out to be mistimed or outright incorrect.

Ackman has underperformed other hedge funds:

• Point72 and Millennium gained +14.5% and +10.5% in H1 2026.

• While Pinpoint Asset Management and Dymon Asia returned +16.9% and +15%, respectively.

The underlying mechanics of this underperformance reveal that Pershing Square has struggled because some of its portfolio companies have faltered in 2026.

The “fallen from grace” stocks include:

$Brookfield Corp(BN)$

One of the clearest examples is Brookfield Corporation (BN).

I remembered covering this when I was sharing Ackman’s 13F filings in my 02 Aug 2025 post. Click here ! for the details.

As of 17 Jul 2026

BN a key part in his portfolio, has dropped by +6.43% YTD instead of participating in the broader market’s strength. (see above)  

What was supposed to be a defensive, cash‑flow‑rich exposure has instead acted like a source of negative alpha.

$Amazon.com(AMZN)$

The same is ‘true’ for AMZN. (see below)

As of 17 Jul 2026

While AMZN has risen by +7.11%, it has lagged broader tech momentum as concerns about its massive capex spending persists. (see above)

$Microsoft(MSFT)$

Ackman began quietly building a new position in MSFT during February 2026, with an implied average purchase price in the low $400.

Pershing Square (PS) eventually disclosed the 5.65 million-share stake in its 15 May 2026’s 13-F filing with the SEC.

The tech titan purchase has remained under pressure in 2026. so far. (see above)

As a result of these misalignments with market momentum, key Pershing Square stocks have pulled back significantly:

• Pershing Square Inc (PS) - stock has dropped to $34 from the all-time high of $54.

• Pershing Square USA (PSUS), fund managed by PS, is hovering near its all-time low of $36.75, slumping by over -15% from its all-time high.

• Pershing Square Holdings (PSHD), Ackman’s closed-end fund (CEF) has dropped by -25% from its peak in 2026.

Ackman’s direct personal consequence of these market miscalculations sees his net worth of $14.3 billion (at its peak in early 2026) has fallen to around $10 billion, now.

The lesson is not that process is worthless, but that even a robust process cannot guarantee near‑term success when the market chooses other narratives.

Costly Premature Exits.

Ackman’s struggles demonstrate the pain of (a) holding assets that falter or (b) buying into tech themes at the wrong moment.

At the other end of the spectrum is the recent performance of BRK.B, highlighting a different way an investment guru can be wronged.

It’s by leaving staggering amounts of money on the table due to ill-timed, overly aggressive selling.

At a first glance, BRK.B top-line numbers look impressive.

The equity portfolio is off to a strong start in the third quarter thanks to gains in many of its largest holdings, led by $Apple(AAPL)$ and $American Express(AXP)$.

Overall, the portfolio is up more than $20 billion since 30 Jun 2026 or about +6.0% by Barron’s estimates, while the S&P 500 is about flat.

The portfolio now totals $356 billion based on CNBC’s running total of its latest value.

BRK.B’s largest holding, AAPL, has climbed nearly +15% in July 2026 to about $330 /share, after hitting a record high of just under $335 earlier on Fri, 17 Jul 2026.

The surge has been driven by investors who are:

• Increasingly optimistic about AAPL’s AI strategy, its sore point in recent quarters.

• Encouraged that the company is not spending as aggressively on AI development as some peers.

Beneath these massive nominal gains lies a harsh reality.

BRK.B has reduced its stake in AAPL more than 75% from its peak, with most of the shares sold in 2024 at much lower prices.

I have covered Mr Buffett’s sales in BRK.B’s 13F filing. click here ! for the details.

With hindsight, Buffett’s decision to drastically reduce Berkshire’s AAPL stake has proved costly.

Apple Inc (AAPL).

BRK.B’s AAPL holding peaked at about one billion shares before falling to about 228 million shares, that still commands a whooping $75 billion. (see below)

Green = Buy & Red = Sell

Bulk of the sale occurred in H1 2024 when the stock traded around $190 a share.

The financial cost of being wrong on this scale is breathtaking.

Barron’s estimates that BRK.B may have left as much as $100 billion on the table given the rally in AAPL since 2024.

Compounding the sting of the missed upside, BRK.B had a sizable tax bill that could have totaled about $20 billion on the AAPL sales.

This is a glaring miscalculation considering their cost basis is around $35 /share, with most of the AAPL purchases transacted from 2016 - 2018 when it traded under 15x earnings (vs currently, it fetches over 30x).

Though AAPL remains nearly a ten-bagger for BRK.B, still the decision to slash its position severely capped what could have been an even more historic return.

Unfortunately, AAPL was not an isolated incident of aggressive selling backfiring.

Bank of America (BAC).

BRK.B have also sold its $Bank of America(BAC)$ stake, equally aggressive too, in the past 2 years. (see below)

Green = Buy & Red = Sell

This as BAC has rallied lately and hit a new 52-week high of $62 earlier on Fri, 17 Jul 2026 as well, thanks to rotation out of semiconductors, storage and AI.

BRK.B still Berkshire owns 513 million shares, having sold the about 500 million shares in the $40s range.

The thesis of owning a scale US bank (for BRK.B) that benefits from normalized rates & fee income, remains intact.

However, trimming its BAC position earlier at lower prices meant BKR.B captured less of the stock's later gains than it would have by holding all its shares.

BRK.B would be higher if Mr Buffett hadn’t decided to slash the AAPL & BAC stakes, back then.

While higher equity prices across BRK.B’s portfolio have boosted estimated book value to around $535,000 /Class A share, up from $522,000 on 30 June 2026, the stock itself has not benefited from the gains in its portfolio:

• Class A shares are down about -1% since 30 Jun 2026.

• Both classes of stock are down -2% this year, well behind the S&P 500’s total return of more than 10%.

The stock now trades for a reasonable 1.4x the estimate of the current book value, that is at the lower end of the range in recent years.

This is down from a peak of 1.8x back in May 2025, just before Warren Buffett announced his stepping down as CEO at end of 2025.

While it can be hard to pinpoint why BRK.B is underperforming or outperforming the index, it could be lagging because it’s the ultimate defensive stock in a technology-led rally in 2026, so far.

Furthermore, the “Buffett premium” has ‘kind of’ vanished from the stock.

Investors may be taking a wait-and-see attitude toward new CEO Greg Abel.

His pace of investments, including a $10 billion purchase of $Alphabet(GOOG)$ in June 2026, remains modest relative to BRK.B’s cash levels of nearly $400 billion and its $1 trillion market value.

While BRK.B’s AAPL and BAC sales now appear ill-timed, the stock seems to be getting unfairly discounted even as the BRK.B portfolio advances.

Berkshire Hathaway Inc (BRK.B).

If there is a bright spark (left), it’s that BRK.B appeared to have ramped up its share buyback in the second quarter.

According to Barron’s estimates:

• BRK.B has purchased between $5 billion - $11 billion of its stock in the second quarter and the first two weeks of July 2026.

• Compared with just $235 million in the first quarter.

The calculation is based on a filing Warren Buffett made earlier in the week regarding his BRK.B ownership stake.

With BRK.B slated to report its own quarterly earnings tentatively on 01 Aug 2026, will there be a late-stage magic to help turnaround its stock price, before that ?

Two wrongs don’t make a Right !

By bring these threads together, Ackman & Buffett illustrate 2 distinct ways in which investment gurus can be wronged by markets and timing.

Bill Ackman.

In Ackman’s case, the “wrongness” sits in the performance of specific names versus benchmarks over a defined period.

• Brookfield, Uber, Hertz, Restaurant Brands, Freddie Mac, and Fannie Mae are all logically defensible bets, each supported by multi‑layered theses.

Yet collectively, they have underperformed in 2026, when passive index exposure and less concentrated peers do well.

The consequence is a visible performance gap that erodes the halo effect of past successes and reminds investors that high‑conviction concentration magnifies both skill and error.

Personally, I think Ackman did not fail on his stocks pick.

He failed to understand the sitting president’s (a) chaotic thought process and (b) unorthodox, shortsighted style of running the country by force, plunging it into an abyss.

Warren Buffett.

As for Buffett, the “wrongness” is less about picking bad businesses and more about trimming great ones too soon.

AAPL and BAC, are not broken stories; they are thriving positions that have rallied strongly.

The error lies in monetizing them aggressively at levels that, (with hindsight), were still early in their re‑rating.

BRK.B’s portfolio and book value benefit from 2026’s rally, but the stock’s muted multiple and lagging total return suggest that the market is:

• Discounting the opportunity cost of those sales.

• Layering that narrative onto existing concerns about (i) succession and (ii) capital deployment.

Both episodes reinforce the same overarching theme:

• Long track record does not confer immunity from mis‑timing or from the tyranny of reporting periods.

• Even well‑reasoned, analytically sound decisions can look deeply wrong in hindsight when the market’s path diverges from the base case.

• The market judges outcomes, not process, and does so in real time, even when the underlying process is designed for multi‑year horizons.

It is true that Mr Buffett has sold the stocks too early vs had he held onto them, BRK.B would have been even more cash rich.

Personally, if investors looked at the sales in ‘half full’ mentality, Mr Buffett still made a lot of money for BRK.B, despite the post’s narrative.

For investors, the takeaway is not that we should dismiss gurus or ignore their frameworks.

On the contrary, Ackman’s and Buffett’s stories show why process and discipline matter.

This is because they enable recovery from missteps and prevent panic when the market temporarily punishes a stance.

However, the same stories also caution against hero worship.

No manager, however skilled, is exempt from periods where the stocks that once demonstrated their brilliance now underline their fallibility.

In that sense, the stock examples quoted of BN, AMZN, MSFT on the Pershing side, and AAPL & BAC on Berkshire side, they are not footnotes (small details).

They show that “investment gurus can be wronged sometimes, too” is not a theoretical statement about risk, but a live reality playing out in some of the most closely watched portfolios in the world.

They are real-life proof that even stock market gurus can get it wrong, a reminder to investors (like me) that nobody gets it right all the time. Agree ?

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• INTC : Q2 Earnings is Proof of Return ?

• Do you think Ackman’s underperformance this year stems from poor stock selection, or from his concentrated style getting caught on the wrong side of broader macro trends?

• Do you think Buffett’s decision to reduce AAPL and BAC stakes was a rare misstep, or a disciplined cash-raising move that investors are judging too harshly with hindsight? ?

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