Bill Ackman’s Concentrated Portfolio: 3 Stocks Driving $13.6B Hedge Fund
Explore how Bill Ackman’s hedge fund Pershing Square invests over half its $13.6 billion portfolio in just three stocks, revealing insights into concentrated investing and strategic bets on Uber, Brookfield, and Howard Hughes.
Key Takeaways
- Ackman invests over 50% of $13.6B portfolio in 3 stocks
- Uber is largest holding at 19%, valued near $2.6B
- Brookfield offers diversified assets trading below intrinsic value
- Howard Hughes aims to become a Berkshire Hathaway-like holding
- Concentrated investing reflects high conviction but carries risks
Bill Ackman’s Pershing Square Capital Management isn’t playing the usual hedge fund game of spreading bets thin. Instead, Ackman has boldly concentrated over half of his $13.6 billion equity portfolio into just three stocks as of mid-2025. This focused approach reveals his confidence in select companies that blend growth, value, and strategic innovation. From ride-sharing giant Uber to diversified asset manager Brookfield, and the ambitious real estate firm Howard Hughes Holdings, Ackman’s picks tell a story of conviction and transformation. In this article, we unpack these three key stocks, explore Ackman’s activist investment style, and consider what lessons investors might draw from his concentrated portfolio strategy.
Concentrated Investing Strategy
Bill Ackman’s Pershing Square Capital Management takes a bold stance in the hedge fund world by concentrating over 50% of its $13.6 billion equity portfolio into just three stocks. This isn’t your typical scattergun approach; it’s a high-conviction play that reflects Ackman’s activist style, where deep knowledge and influence over companies matter more than broad diversification. Think of it as betting big on a few horses you know well rather than spreading chips across the entire racetrack.
This strategy challenges the common myth that diversification is always safer. While spreading investments can reduce risk, Ackman’s focused portfolio shows that carefully chosen, high-quality companies can offer outsized returns. However, this also means the stakes are higher—if one of these core holdings stumbles, the impact on the portfolio is significant. For investors, this approach underscores the importance of understanding what you own and why, rather than chasing every shiny stock.
Uber: The Ride-Share Powerhouse
Uber Technologies stands tall as Ackman’s largest holding, making up roughly 19% of his portfolio and valued around $2.6 billion after an initial $2.3 billion investment in early 2025. Ackman’s admiration for Uber goes beyond numbers; he’s a longtime user who believes in the company’s ability to generate strong free cash flow and profitable growth across both ride-sharing and delivery segments.
Despite whispers that autonomous vehicles might disrupt Uber’s business, Ackman sees the company’s vast network of over 170 million users and millions of drivers as a moat. Uber’s partnership with Waymo, Alphabet’s self-driving car unit, positions it as a natural collaborator rather than a casualty in the autonomous future. Financially, Uber’s recent 35% surge in EBITDA and 66% jump in free cash flow year over year paint a picture of a company scaling efficiently. Yet, with the stock up 45% since Ackman’s purchase and trading at a forward P/E of 24.5, investors should weigh growth prospects against valuation and the evolving autonomous landscape.
Brookfield: Diversified Asset Value
Brookfield Corporation, accounting for about 17% of Ackman’s portfolio, offers a diversified mix of real estate, renewable energy, and infrastructure investments. Pershing Square began building this position in 2024 and has steadily increased it to roughly $2.4 billion. Brookfield’s unique corporate structure—with publicly traded subsidiaries like Brookfield Asset Management, Infrastructure, and Renewable—gives investors flexible access to a broad asset base.
The company’s distributable earnings jumped 27% year over year in Q1 2025, helped by strategic divestments and a focus on high-return assets. Management projects cash flow growth above 20% annually through 2029, unlocking $47 billion for new investments or shareholder returns. Trading at 13.8 times trailing distributable earnings, Brookfield appears undervalued compared to management’s suggested floor of 16 times. For Ackman, this represents a bargain—a chance to own a diversified asset manager with strong growth and value potential.
Howard Hughes: Building a Berkshire
Howard Hughes Holdings is Ackman’s ambitious project to transform a real estate company into a diversified holding powerhouse, echoing Warren Buffett’s Berkshire Hathaway. With a 47% stake worth about $1.9 billion, Pershing Square is steering Howard Hughes beyond master-planned communities into new ventures like insurance, aiming to harness float—the premiums collected before claims—as cheap capital for investments.
The company’s assets, valued at $5.9 billion, trade at a discount to its $4 billion market cap, with net operating income expected to grow modestly by 4% in 2025 and 37% longer term. While the deal includes fees paid to Pershing Square, the vision is clear: build a multi-faceted holding company that generates cash flow, pays down debt, and repurchases shares. This transformation is a marathon, not a sprint, requiring patience from investors betting on Ackman’s Berkshire-inspired blueprint.
Lessons from Ackman’s Portfolio
Ackman’s concentrated portfolio offers a fresh perspective on investing myths. The idea that more stocks equal less risk doesn’t always hold when you deeply understand your picks. His focus on Uber, Brookfield, and Howard Hughes shows a blend of growth, value, and strategic transformation—each with unique catalysts and risks.
Investors should note that while Uber’s rapid growth and partnerships position it well, the future of autonomous vehicles injects uncertainty. Brookfield’s diversified assets trade below intrinsic value, signaling opportunity but requiring faith in management’s execution. Howard Hughes embodies long-term vision but comes with fees and a slow unfolding story. Ultimately, Ackman’s approach invites investors to think critically about concentration, conviction, and the patience needed to see big ideas through.
Long Story Short
Bill Ackman’s concentrated portfolio strategy is a masterclass in conviction investing, spotlighting just three stocks that together shape over half of his $13.6 billion equity holdings. Uber’s dynamic growth and strategic partnerships, Brookfield’s undervalued diversified assets, and Howard Hughes’ transformation ambitions offer a compelling trio of opportunities. Yet, this approach isn’t for the faint-hearted—concentration amplifies both potential gains and risks. Investors should weigh the allure of Ackman’s high-conviction bets against their own risk tolerance and investment horizon. While following a billionaire’s moves can be tempting, remember that patience and due diligence remain your best allies. Ackman’s journey with Howard Hughes, aiming to emulate Berkshire Hathaway’s diversified holding model, reminds us that visionary investing often requires time and resilience. For those ready to dive deep, these three stocks offer a vivid glimpse into how focused investing can shape financial futures.