Bill Ackman Cut Chipotle and Bought Uber — Should You?

TL;DR: TODAY’S EDITION

• Bill Ackman is one of the boldest hedge fund managers out there — known for high-conviction, high-stakes investing.

• He just made Uber his #1 holding (17.7%) and doubled down on Brookfield and Howard Hughes.

• From 2018–2023, copying his top picks beat the S&P 500 every single year.

• But 2024 and 2025 YTD? You’d be in the red.

BILL ACKMAN

Bill Ackman doesn’t do subtle.

The hedge fund legend behind Pershing Square just filed his latest 13F, and it’s a full-on shakeup.

🚨 Uber Technologies (UBER) — brand new to his portfolio — is now his #1 position, weighing in at almost 18%.

🚨 He doubled down on Brookfield Corporation (BN) and Howard Hughes Holdings (HHH).

🚨 Meanwhile, he slashed Chipotle (CMG) by 12% and nearly halved his stake in Hilton (HLT).

But here’s the real question: Does it pay to copy Bill Ackman’s moves?

We ran the numbers — and the results might surprise you.

👤 Who is Bill Ackman (and What’s Pershing Square)?

Bill Ackman is the billionaire founder of Pershing Square Capital Management, known for his activist investing style. He made waves by betting against MBIA ahead of the 2008 crisis, and later for his huge win with General Growth Properties — and his big loss with Valeant Pharmaceuticals. Pershing Square manages billions, built on Ackman’s bold, high-conviction strategies that often attract headlines and debate.

🔍 Ackman’s Current Top 10 Holdings

Pershing Square’s portfolio is anything but diversified — it’s concentrated, bold, and deliberate. Ackman bets big when he’s convinced. Right now, Uber tops the list with a whopping 17.7% weight, despite being brand new. That’s followed closely by real estate-heavy names like Brookfield (BN) and Howard Hughes (HHH) — showing his conviction in long-term asset plays. Other key holdings include Chipotle (CMG) and Restaurant Brands (QSR) on the consumer side, Alphabet (both share classes), and Canadian Pacific (CP). It’s a tight portfolio of high-conviction ideas — the kind where every pick counts, and every move says something.

Here’s what he’s currently betting on (from the Q1 2025 13F):

🚖 Why Uber?

Uber Technologies is booming. Their latest earnings show 14% year-over-year growth in gross bookings and revenue, with record-high active users and trip volumes. Uber isn’t just a ride-hailing app anymore: it’s aggressively expanding into autonomous vehicles through partnerships with players like May Mobility, WeRide, and Pony.ai.

This lets Uber integrate cutting-edge tech while avoiding massive R&D costs — positioning it as the operating system of future mobility. On top of that, they’re expanding into low-density suburbs, scaling up delivery, and harnessing AI for better efficiency. With only 5% of the adult population in its markets using Uber, there’s plenty of room for growth.

📈 Would Copying Ackman Have Worked?

Here’s how a copycat portfolio of Ackman’s top picks (rebalanced each quarter) would’ve performed vs. the S&P 500 over the past 7 years:

💡 From 2018 to 2023, copying Ackman’s moves beat the S&P every single year, with outperformance peaking at nearly +17% in 2019.

💡 But in 2024 and 2025 YTD? Not so pretty. You’d be down –12.6% in 2024 and –5.9% so far this year.

🤔 Should You Follow His Lead?

Ackman is a high-conviction, headline-grabbing investor, with a knack for bold plays and sharp pivots.

After a rough 2024 and a negative YTD in 2025, Ackman needs a new hit to turn the tide. His past wins — from General Growth to Restaurant Brands — were bold, contrarian, and timed just right. Now, with Uber as his top position, he’s clearly betting this is the comeback catalyst. It’s a high-growth story with real momentum — and if it plays out, it might just be the move that gets Ackman back in the outperformance column.

Looking for higher returns — without the guesswork?

While copying Ackman would’ve paid off handsomely from 2018 to 2023, 2024 and 2025 haven’t been as kind. That’s the challenge with following investors — timing matters, and conviction can cut both ways.

With Smart Money Premium, you don’t have to guess which investors to follow — we already did the work for you. You get access to the Top 20 investors across 3-, 5-, and 7-year timeframes — the real long-term outperformers.

Take Institutional Venture Management XVI from our 3-years Top List. They hold just two stocks. If you’d mirrored them in January, you’d be up +118% YTD — while the S&P 500 has barely budged. And they’re still holding on to just these two positions. Want to know what they are? Go Premium now and you can start replicating them today to position yourself for the next surge. Because when the market moves, the biggest profits are made by those who are already in. 💥

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