How Bill Ackman Concentrates $7.4 Billion Across His Most Conviction-Driven Holdings

Bill Ackman operates Pershing Square Capital Management with a philosophy fundamentally at odds with traditional indexing. Rather than spreading capital thin across dozens of positions, he builds outsized stakes in a carefully selected handful of companies trading below their intrinsic value. This concentrated approach—with just 10 publicly traded holdings in a $14.4 billion portfolio—has become his signature strategy. And in 2025, Bill Ackman doubled down on this conviction-based methodology by deploying billions into three exceptional opportunities that collectively account for over half of the fund’s publicly traded assets.

The power of conviction investing lies in the ability to truly understand a business and capitalize when price disconnects from value. Ackman’s willingness to commit multi-billion dollar positions allows him to influence capital deployment decisions and shape long-term outcomes. His recent filings and quarterly updates reveal precisely where he sees the most compelling opportunities in today’s market.

Uber: Capitalizing on a Transportation Empire in Transition

Uber represents 19.7% of Pershing Square’s portfolio, making it the largest single holding. Bill Ackman’s team accumulated 30.3 million shares in early 2025 before publicly announcing the position in February, and SEC filings confirmed it became Pershing Square’s dominant position by the first quarter. The stock has surged roughly 55% since year-start, reaching unprecedented heights.

Yet the most intriguing opportunity lies ahead, not in past performance. While skeptics view autonomous vehicles as an existential threat to Uber’s ride-sharing model, Bill Ackman sees an asset that few competitors can replicate: Uber’s 170 million monthly active users on its transportation platform. This unparalleled customer base represents a distribution channel that autonomous vehicle companies—including Alphabet’s Waymo—are actively seeking to leverage. Waymo has already inked operational partnerships with Uber in multiple cities, validating the platform’s strategic value.

From an operational standpoint, Uber is executing at scale. Last quarter, gross bookings grew 14%, while EBITDA accelerated 35% thanks to improved leverage. The company converted over 100% of EBITDA into free cash flow through disciplined capital management, generating 66% growth in that metric. These improvements suggest the business has reached an inflection point toward sustained profitability.

The valuation remains compelling even after the run-up. At roughly 23 times forward EBITDA, Uber trades at a discount to companies with slower growth trajectories. Management projects EBITDA expansion exceeding 30% over the coming years—a rate that more than justifies current multiples and suggests significant upside remains for patient investors.

Brookfield: The Buffett Blueprint Applied to Alternative Assets

Brookfield occupies 18.4% of the portfolio, reflecting Bill Ackman’s methodical accumulation over four quarters. The Canadian alternative asset manager operates a diversified ecosystem spanning real estate, renewable power infrastructure, and asset management—precisely the conglomerate structure that Warren Buffett pioneered at Berkshire Hathaway.

What distinguishes Brookfield is its capital generation engine. Beyond managing $900 billion in assets (generating recurring fees), the company operates profitable businesses that produce cash available for reinvestment. Additionally, Brookfield Wealth Solutions’ insurance operations provide float—a financial engineering tool that Ackman has publicly expressed desire to employ himself. This multi-layered cash generation model allows management to continuously acquire high-return assets while returning capital to shareholders through buybacks.

The results speak for themselves. Over five years, distributable earnings per share have expanded at a 19% annual rate. Management has guided to $6.33 per share by 2029, implying a 16% compound annual growth rate from 2024 levels. In the most recent quarter, earnings expanded 30% year-over-year—demonstrating the business continues firing on all cylinders.

Despite this trajectory, the stock trades at merely 19 times trailing earnings—well below comparable conglomerates and alternative asset managers. Bill Ackman recognizes this valuation disconnect as an opportunity. The market has yet to fully price in Brookfield’s compounding machine, leaving room for material appreciation as consensus recognition grows.

Howard Hughes: From Real Estate Operator to Ackman-Controlled Holding Company

The third pillar of the portfolio is Howard Hughes, representing 13.3% of publicly traded assets. However, this position tells a story of transformation. In May 2025, Bill Ackman facilitated a transaction through Pershing Square, investing $900 million for 9 million shares that granted him both a 46.9% economic stake and 40% voting control—positioning him as executive chairman.

The strategic vision is ambitious: converting Howard Hughes’ real estate operations into a diversified holding company modeled after Berkshire Hathaway. Bill Ackman’s stated first move involves acquiring or building an insurance business to tap into float economics, mirroring Buffett’s decades-long playbook.

Today’s core business remains undervalued by a wide margin. Management estimates the net asset value of master-planned communities, residential and commercial properties, and operating assets at roughly $5.8 billion per share—this figure excludes corporate debt and was calculated before Pershing Square’s capital infusion. Howard Hughes’ market capitalization, by contrast, sits at only $4 billion, suggesting significant embedded optionality.

The cash generation model reinforces the value case. By controlling all acreage within its master-planned communities, the company calibrates residential and commercial development to precisely match demand, maximizing capital returns. Operating cash flows from home sales and rental income fund new investments, increasingly deployed through the holding company structure now being erected.

The restructuring does carry costs. Howard Hughes will compensate Pershing Square $3.75 million quarterly plus a 0.375% incentive fee tied to value creation above inflation. However, this arrangement allows retail investors to gain indirect access to Bill Ackman’s dealmaking capabilities and private market opportunities historically reserved for institutional partners.

The Concentrated Conviction Bet

Bill Ackman’s $7.4 billion concentration across three holdings represents either exceptional foresight or catastrophic overconfidence—history will determine which. What cannot be disputed is the internal logic: each company operates with pricing power, generates substantial cash, and trades below conservative estimates of intrinsic value.

The portfolio tilt reflects a specific thesis: scale and defensibility matter more than pure diversification. Uber’s network effects, Brookfield’s cash engines, and Howard Hughes’ geographic moats each represent businesses capable of compounding capital at rates substantially above the cost of capital. For an investor with conviction and staying power, concentration becomes not a liability but a feature.

For those inclined to follow Bill Ackman’s moves, these positions offer a roadmap to where deep value may still be found despite the strong equity markets of recent years. The real catalyst—time—remains ahead.