Where Bill Ackman’s Big Bets Lie: Uber, Howard Hughes & His 5 Key Holdings

Pershing Square’s portfolio is highly concentrated in five large public companies, which together make up about three quarters of its $15 billion stock holdings. This concentration reflects not just confidence in those names, but a willingness to accept lack of diversification in exchange for higher expected return through deep knowledge, operational leverage, and control—especially in Howard Hughes, where Ackman is taking on a quasi-operating role. Detailed facts and figures below help assess the strategy’s viability and strategic risks.

Howard Hughes: Building a Holding Company Platform. Pershing Square invested $900 million in May 2025 to acquire 9 million new shares, increasing its ownership from ~37.6% to ~46.9% economic stake and capping control (voting power) at ~40% [2][3]. Ackman is executive chairman and aims to transform Howard Hughes into a diversified holding company akin to Berkshire Hathaway—first major move: acquiring or building a property-casualty insurance arm [1][3][5]. The firm’s asset base (real estate, master planned communities) is seen as undervalued relative to management’s estimated NAV, suggesting potential upside if value is unlocked [5][1].

Core Public Equity Positions: Uber, Brookfield, Alphabet, Restaurant Brands. Uber was bought in January 2025 (≈30.3 million shares), now representing ~19-20% of the portfolio; key rationale is network effects, cash flow, resilient earnings, and upside from autonomous vehicle partnerships [1][2]. Brookfield (BN) is Ackman’s second largest holding (~17-18%), with diversified exposure—including Brookfield Asset Management, infrastructure, renewable energy—and growth in its insurance and wealth solutions business intended to benefit from demographic tailwinds [1]. Alphabet adds exposure to AI, cloud, search, and monetization; though growing, Ackman believes the market is still underappreciating its forward momentum [1]. Restaurant Brands International (QSR) offers an asset-light, franchise / royalty model with strong international growth; the U.S. segment, especially Burger King remodeling and enhancement, is being targeted for improvement [1].

Valuation and Risk Considerations. The concentration, while offering potential high returns, exposes Pershing Square to sector-specific and idiosyncratic risks. Uber’s valuation, trading at ~22-25× forward EBITDA, hinges on maintaining EBITDA growth over 30% and free cash flow conversion—if either slows, pressure may mount [4][1]. Real estate assets in Howard Hughes may be sensitive to interest rates, construction cycles, and regulatory land use. Alphabet, while a bet on AI, faces competition and regulatory risk. QSR’s performance depends on consumer trends, cost pressures, and execution challenges especially in its U.S. brands [1]. Also, the funding of large transactions (like the HHH equity purchase) from cash and negotiations over ownership control raise questions around governance and minority shareholder interests [2][3].

Strategic Implications. Ackman is positioning to leverage both public markets and privately engineered value creation: through activism, operational shifts, asset divestments, and control over entities (e.g. Howard Hughes). Success hinges on execution: delivering on projected EPS growth, integrating new businesses, managing capital allocation carefully, and preserving intrinsic value. The move into insurance via Howard Hughes not only adds float but changes risk profile; similarly, deep ownership in Brookfield and Uber ties returns to macro trends (infrastructure, ESG, AI, regulation). Investors following Ackman should monitor whether portfolio concentration yields alpha net of risks or whether volatility from large exposures drags overall performance.

Open Questions.

• How sustainable is Uber’s estimated >30% annual EPS growth in a competitive, regulatory environment, especially with emerging autonomous vehicle risks and margin pressures?
• Will Howard Hughes be able to build/acquire an insurance business that meets Ackman’s expectations, and what’s the capital intensity and risk there?
• Given the rich valuations in Brookfield, Alphabet, Uber, etc., what sentinel events (interest rates, regulation, slowdown in AI) could sharply alter performance?
• What is the impact of large stake purchases (e.g. new HHH share issuance) on dilution for existing shareholders, and how will governance conflicts be handled?
• Does pursuing such high conviction in few names limit liquidity or flexibility in responding to market dislocations?