Did you know Bill Ackman publishes commentary on his best ideas every quarter?
Pershing Square just released their Q2 2025 letter with details on their best ideas in the portfolio....
(Link here)
When I worked at Blackstone's hedge fund group in 2016, we got exclusive access to quarterly letters just like this from elite managers.
These deep dive thesis documents are typically reserved for investors who commit millions to the fund - but Ackman's publicly traded structure means retail can now access the same institutional research that used to be behind closed doors.
Here's the problem: you can't trust the words alone.
Ackman is famous for his "world is melting down" CNBC rant during COVID's bottom - while simultaneously unloading billions in put options for massive gains.
(His public narrative doesn't always match his private positioning.)
However, by using AI to combine the qualitative letters with official SEC data showing what he actually bought or sold can give us a ranking of his top conviction ideas....which we can use to copytrade.
(Spoiler: AI says he's most bullish on $HHH, $UBER, and $QSR)
I'm going to show you an AI technique that cross-references Ackman's written thesis with his actual 13F position sizing to generate conviction scores on his holdings.
Here's the plan:
- AI extracts every stock thesis and market view from the Q2 letter
- AI maps his 13F buy/sell/hold patterns against these written views
- AI generates conviction scores based on word-to-action alignment
- AI flags potential copy trades where thesis aligns with our worldview
This helps us sort idea generation for our own portfolios. If Ackman's thesis aligns with our market view and his capital allocation backs it up, we can consider deeper diligence on the same names.
The Prompt
Let's use ChatGPT's Thinking Mode
Prompt 1:
You are a senior buy-side analyst. Analyze Bill Ackman’s Pershing Square June 2025 interim letter (https://assets.pershingsquareholdings.com/wp-content/uploads/2025/08/20192925/Pershing-Square-Holdings-Ltd.-June-2025-Interim.pdf) and Pershing Square’s last 6–8 quarters of 13F filings.
Task:
Extract the investment theses Ackman states in the letter for each stock he discusses.
Compare those theses to actual 13F position changes (adds, trims, holds, new, exits).
Produce conviction scores for each holding.
Output: Return only the following 5 tables in this exact order. Do not output any narrative text after them.
Executive Summary
| Worldview (2–3 bullets) | Highest conviction names (ticker + reason) | Key catalysts (next 6–12 months) |
Letter Thesis Map
| Ticker | Company | Theme tags | Thesis (2–3 bullets) | Catalysts cited | Risks cited | Letter pages |
13F Position Changes
| Period end | Ticker | Shares | Market value | QoQ % change | Action (Add/Trim/Hold/New/Exit) | Notes |
Reconciliation
| Ticker | Letter stance (1 line) | 13F action summary | Alignment (Green/Yellow/Red) | Evidence refs (page + period) |
Conviction Scores
| Ticker | Score (0–100) | Thesis clarity (0–20) | Capital allocation (0–20) | Position trend (0–15) | Time in trade (0–10) | Catalyst density (0–10) | Risk acknowledgment (0–10) | Insider alignment (0–5) | Macro alignment (0–10) |
Rules:
Always cite page numbers for letter evidence.
Cite 13F by quarter end date.
Normalize for splits and corporate actions.
Label alignment Green if letter + 13F agree, Yellow if mixed, Red if contradict.
Use concise bullets inside table cells.
The Result
Full output here: Link
Our AI analysis reveals Ackman's actual conviction hierarchy - and it's not what the headlines suggest.
HHH (92/100) emerges as his highest conviction play. AI caught what most missed: Ackman's $900 million primary capital injection sits outside normal 13F mechanics, meaning his true economic exposure is far larger than reported filings show. Combined with his executive chairman role, it's clear he's investing more than just capital here.
UBER (88/100) ranks second with perfect word-to-action alignment. Ackman initiated the position in Q1 and held steady through Q2 while NLP detected strong conviction syntax when discussing Ackman's thesis in the letter. The AI flagged this as a "core" holding based on both letter emphasis and position sizing relative to portfolio.
Most surprising: CMG drops to 7th place (76/100) despite Ackman's bullish commentary. The AI detected the disconnect - he trimmed shares in Q1 while still praising the concept. If you only read the letter you would have missed that he's actually reducing position while saying it's a great opportunity!
Two conviction patterns emerged:
- Green flags (92-79 scores): New positions (UBER, AMZN) or structural plays (HHH, BN) where thesis and capital allocation perfectly align
- Yellow flags (76-70 scores): Legacy positions (CMG, HLT) where valuation discipline trumps narrative love
The AI also surfaced that Ackman's 2025 portfolio moves favor "AI beneficiaries with cash generation" over "pure growth" - adding UBER, AMZN, and GOOGL while trimming high-multiple names like CMG and HLT.
Copy trade candidates: HHH and UBER show the strongest thesis-to-allocation alignment for investors seeking to mirror Ackman's highest conviction bets rather than his most publicized ones.
