Bill Ackman's 39.5% Bet: What the 13F Hides About Insider Skin in the Game

The headline number is staggering: Pershing Square's Q3 2025 13F filing shows a concentrated portfolio where Uber is the largest holding at 20.25% of the $14.6 billion fund. That's a massive bet, a 39.5% allocation to a single stock if you include the parent company's stake. But in the world of insider tracking, the headline is often the trap. The real signal isn't the size of the bet, but who's putting their own skin in the game.

For all the concentrated skin in the game from Bill Ackman's firm, the parent holding company's insiders tell a different story. The most recent trading activity there, in November 2024, shows net selling. On November 13th, Director Bronwyn Curtis executed a net sell of 554 shares, and Director Curtis B. sold 554 shares. That's a clear signal: when the people closest to the firm's capital are trimming their personal stakes, it's a red flag for the smart money. It suggests a lack of personal conviction at the top, even as the firm's portfolio is heavily weighted toward a single name.

This creates a classic misalignment. The firm is making a concentrated, high-conviction bet on Uber's growth, but the insiders at the parent company are quietly reducing their own exposure. In a pump-and-dump setup, you often see insiders selling while the firm hyping the stock. Here, the firm is the hyping entity, and the insiders are the ones quietly cashing out. That's the setup to watch.

Analyzing the Holdings: Catalysts vs. Insider Actions

The fund's massive 30.3 million share position in Uber represents a significant institutional accumulation, but the stock is scheduled to report Q4 results on February 4th. That's the immediate catalyst. The setup here is classic: a concentrated bet sitting on the edge of a major earnings event. The smart money's real signal, however, isn't in the fund's size, but in the lack of skin in the game from the parent company's insiders, who were net sellers in November. When the firm is betting big on a stock's next move, you want the people pulling the trigger to have their own money on the line. The disconnect is the red flag.

Alphabet shares jumped 65% in 2025, their sharpest rally since 2009, driven by AI momentum. The stock's recent surge, however, may have priced in much of the good news. After a tough start to the year, Google closed out 2025 with its strongest performance, but the question now is whether the AI-driven rally has run its course. For a stock that's already up 65%, the next leg higher requires new, compelling catalysts. The fund's position is a bet that the AI story is just beginning, but the market's recent action suggests a lot of optimism is already baked in.

Amazon's Q4 2024 results showed strong fundamentals, with sales growth of 10%. Yet the stock's recent performance has lagged behind Alphabet's AI-driven surge. This divergence is telling. Amazon is executing well on core growth, but it's not the headline story in a market obsessed with artificial intelligence. The fund's allocation to Amazon, therefore, looks more like a value or growth holding within a concentrated portfolio, rather than a pure momentum play. It's the steady horse in the race, not the one leading the pack.

The bottom line is a misalignment of catalysts and conviction. The fund is positioned for the next big move in each stock, but the insider actions at the parent company suggest a lack of personal conviction in the overall bet. When the firm is making a concentrated, high-conviction play, you want to see the people at the top putting their own money where their mouth is. Here, the smart money is quietly cashing out while the firm hyping the thesis. That's the setup to watch.

The Smart Money's Playbook: What to Watch in 2026

The concentrated bet is now a live wire, set to ignite on February 4th. That's the key watchpoint. Uber's earnings call will be the ultimate stress test for the smart money's thesis. A miss on the top or bottom line could trigger a swift fund sell-off, given the sheer size of the position. The market will be watching for any hint that the growth story is stalling, which would directly challenge the rationale behind Pershing Square's massive accumulation.

Beyond that single event, the playbook is simple: watch the filings. The next 13F reports will show if the fund is adding to its Uber stake or taking profits. More broadly, they'll reveal any new institutional accumulation in other holdings, signaling where the smart money is shifting its focus. For now, the fund's massive position is a bet on a single catalyst. The next filings will show if that bet is being doubled down on or quietly unwound.

Finally, keep an eye on the parent holding company's insiders. Their November selling was a clear signal. Any future shift-particularly a return to personal buying-would be a stronger indicator of conviction. For now, the disconnect remains: the fund is betting big on Uber's future, while the people at the top of the parent company are reducing their own skin in the game. That's the setup to monitor as 2026 unfolds.