How Bill Ackman Leveraged His $14.4 Billion Hedge Fund to Concentrate Capital in Three Market Leaders

When it comes to investment strategy, few names command as much attention as Bill Ackman. His hedge fund, Pershing Square Capital, operates on a principle that challenges conventional wisdom: rather than spreading investments across dozens of holdings like most funds do, Ackman builds fortress positions in a select number of high-conviction companies. This concentrated approach has allowed him to deploy billions into his most compelling ideas and hold them for the long haul. What makes this approach particularly interesting is that his top three holdings now account for more than half of Pershing Square’s entire publicly traded portfolio—a remarkable concentration that reflects extraordinary confidence in these companies’ prospects.

Ackman’s track record of making billion-dollar bets suggests he knows where to find value when others overlook it. His philosophy centers on identifying companies trading below their true intrinsic value, then accumulating substantial stakes over time. By maintaining such a focused portfolio, Ackman avoids the dilution trap that undermines most money managers: when holdings are scattered too widely, the portfolio performance essentially mirrors the overall market, making it nearly impossible to generate meaningful outperformance. Pershing Square’s holdings in just 10 publicly traded companies stand in stark contrast to this industry norm, signaling that every position represents a carefully vetted conviction rather than a casual allocation.

The Ackman Playbook: Why Concentrated Bets in Quality Businesses Matter

What unites the three companies now anchoring Ackman’s portfolio is a shared trait: each operates in capital-efficient businesses with strong competitive advantages, generates substantial cash flows, and trades at valuations that offer meaningful upside potential relative to their intrinsic worth. These aren’t speculative positions; they’re the result of Ackman’s methodical approach to value investing applied at scale.

Throughout 2025, Ackman not only maintained these positions but actively expanded them, signaling unwavering conviction even as stock prices climbed. His quarterly filings and monthly investor updates have become closely watched roadmaps for those seeking to understand where sophisticated capital is flowing in today’s market.

Uber: The World’s Largest Mobility Network at an Attractive Valuation

Ackman’s largest single bet represents 19.7% of Pershing Square’s portfolio. In early 2025, he accumulated 30.3 million shares of Uber Technologies, which subsequently became Pershing Square’s biggest position—a fact revealed in the fund’s first-quarter SEC 13-F filing. Since then, Uber stock has surged approximately 55% from the year’s outset, reaching all-time highs, with a meaningful portion of that rally following Ackman’s public announcement of the position on social media.

But the attraction extends far beyond recent price momentum. Uber’s fundamental business case remains compelling. The company boasts 170 million total monthly active users as of Q1 2025, representing by far the largest customer base in the rideshare and mobility sector. This network represents an invaluable asset that companies scrambling to deploy autonomous vehicle technology would prize dearly. Indeed, Alphabet’s Waymo—the leading self-driving vehicle company—has already executed multiple agreements with Uber to operate driverless services across several cities. Rather than cannibalizing Uber’s business, autonomous vehicles could become a new revenue stream leveraging Uber’s unmatched customer distribution.

Operationally, Uber continues executing on its financial targets. Gross bookings climbed 14% in the most recent quarter, while the company expanded EBITDA (earnings before interest, taxes, depreciation, and amortization) by 35%—a significant jump reflecting improved operating leverage. Even more impressive: Uber converted more than 100% of its EBITDA gains into free cash flow, which surged 66%. With minimal capital intensity required to support this growth, the economics are increasingly favorable.

From a valuation standpoint, Uber trades at roughly 23 times forward EBITDA estimates—a multiple that appears reasonable given that management guidance points to EBITDA expansion exceeding 30% over the coming years. This pricing suggests meaningful room for appreciation, particularly if the company continues to execute.

Brookfield: A Canadian Asset Manager Building a Buffett-Style Conglomerate

Ackman’s second-largest position, representing 18.4% of Pershing Square’s portfolio, reflects a multi-quarter accumulation in Brookfield, the Canadian alternative asset manager. What makes Brookfield particularly appealing to someone like Bill Ackman is its business model: beyond managing assets for third parties, the company operates across real estate, renewable energy infrastructure, and other capital-intensive sectors.

The genius of Brookfield’s structure mirrors the approach that Warren Buffett famously employed at Berkshire Hathaway. The company generates cash from its asset management division and reinvests those flows into operating businesses and additional acquisitions. Adding another source of capital—Brookfield Wealth Solutions, its insurance business—provides a float pool that management can deploy into new opportunities. Ackman has previously stated his interest in adopting a similar model, making Brookfield’s template particularly relevant to his long-term vision.

The financial track record speaks for itself. Over the past five years, Brookfield has grown distributable earnings per share at an average annual rate of 19%, with management projecting a 16% compound annual growth rate through 2029. In the most recent quarter alone, the company delivered 30% growth—a pace that far exceeds overall market expansion. Yet despite these stellar growth metrics, Brookfield’s stock trades at just 19 times trailing earnings per share, a significant discount to comparable diversified asset managers and financial conglomerates.

This valuation gap suggests the market has not fully appreciated the company’s dual growth drivers: the steady cash generation from its existing operating businesses combined with the scalability of its asset management platform. For Ackman, who has demonstrated a talent for identifying mispriced assets, Brookfield appears to represent both stable cash generation and substantial appreciation potential.

Howard Hughes Holdings: Transforming Real Estate Into a Diversified Operating Company

The third pillar of Bill Ackman’s current strategy, comprising 13.3% of his portfolio, involves a deeper commitment than simple stock ownership. In mid-2025, Ackman negotiated an agreement to acquire an elevated stake in Howard Hughes Holdings, with Pershing Square investing $900 million to secure 9 million shares. This transaction granted Ackman a 46.9% economic interest and 40% voting control—and returned him to the board as executive chairman.

The transformation potential is significant. Ackman has openly discussed plans to evolve Howard Hughes from a pure-play real estate company into a diversified holding company framework, again drawing inspiration from the Berkshire Hathaway model. His stated priority is to acquire or build an insurance business—a move that would generate the float Ackman could deploy into additional value-accretive opportunities.

On a standalone basis, Howard Hughes’ existing real estate portfolio carries substantial embedded value. Management has estimated the net asset value of its master-planned communities, residential units, and operating properties (after accounting for corporate debt) at approximately $5.8 billion—a figure that does not yet reflect the boost from Ackman’s capital infusion. The company’s market capitalization, however, sits at just $4 billion, implying a significant discount to underlying asset value.

The operational fundamentals remain robust. Howard Hughes generates strong cash flows by strategically selling land parcels to homebuilders and collecting rental income from its commercial and multifamily properties. Crucially, because the company controls the entire acreage within its master-planned communities, management can calibrate supply to match demand, ensuring attractive returns on each dollar of capital deployed. With the new holding company structure and access to Ackman’s investment network, Howard Hughes gains optionality to deploy this cash into accretive acquisitions and investments.

The arrangement does impose costs: Howard Hughes will pay Pershing Square $3.75 million quarterly plus a 0.375% performance incentive fee tied to value creation above inflation. For average investors, however, the new structure presents an interesting opportunity to gain exposure to Ackman’s private deal-making and capital allocation expertise through a publicly traded vehicle trading below its intrinsic worth.

The Bigger Picture: What Ackman’s Portfolio Reveals About Market Opportunity

The concentration of Bill Ackman’s capital into these three positions reflects a deliberate bet that exceptional opportunities exist in today’s market. While headlines may suggest valuations have become stretched, Ackman’s thesis counters that premise: when examined against their growth trajectories and competitive positions, these companies offer compelling value.

Each company generates substantial free cash flow, operates with durable competitive advantages, and faces significant expansion runways. Uber has global rideshare dominance to defend and autonomous vehicle upside to capture. Brookfield possesses capital deployment capabilities that few diversified asset managers can match. Howard Hughes owns a transformational playbook under new ownership.

For investors seeking to decode sophisticated capital flows, Bill Ackman’s concentration into these three holdings offers a masterclass in value identification. Whether or not these precise companies suit individual portfolios, the methodology behind selecting them—hunting for businesses where intrinsic value exceeds market price, accumulating meaningful stakes, and playing the long game—remains universally applicable.