Bill Ackman, the billionaire investor behind Pershing Square Capital, is known for focusing his hedge fund’s investments on a select few high-conviction companies. With a portfolio of just 10 publicly traded stocks, Ackman’s strategy is to concentrate investments in businesses he believes will outperform the market.
Currently, Ackman has more than 51% of Pershing Square’s portfolio, valued at $14.4 billion, allocated to three standout stocks. His recent updates and disclosures provide insights into his investment philosophy.
Ackman’s Top Three Holdings
- Uber (19.7% of Portfolio) Ackman acquired 30.3 million shares of Uber (UBER) at the beginning of 2025, announcing the position on social media in early February. This has become his largest holding, with shares rising about 55% since the start of the year, reaching an all-time high largely due to Ackman’s investment announcement.
The long-term outlook for Uber remains promising. While some view autonomous vehicles as a threat, this development could also present opportunities. Uber boasts a substantial customer base, with 170 million monthly active users, and its market share continues to grow. Collaborations with Alphabet’s Waymo for self-driving cars further enhance its potential.
Financially, Uber is on track, reporting a 14% increase in gross bookings last quarter and a 35% rise in EBITDA. With limited cash expenditures, free cash flow surged by 66%. Despite its recent price rise, shares are considered fairly valued, trading at an enterprise value of less than 23 times forward EBITDA estimates, especially as management anticipates over 30% EBITDA growth in the coming years.
2. Brookfield (18.4%)
Over the last year, Ackman has built a position in Canadian asset manager Brookfield (BN), which operates in various sectors, including real estate and renewable energy. These cash-generating businesses provide capital for further investments.
Brookfield’s Wealth Solutions, its insurance division, offers additional funding for investments—a strategy reminiscent of Warren Buffett’s approach with Berkshire Hathaway. Over the past five years, Brookfield has averaged a 19% annual growth in distributable earnings per share, with management projecting that trend will continue. The company aims for $6.33 in earnings per share by 2029, representing a 16% compound annual growth rate.
Currently, Brookfield’s stock trades at just 19 times trailing earnings, well below its peers, suggesting it may be undervalued given its growth potential.
3. Howard Hughes Holdings (13.3%)
After acquiring a larger stake in Howard Hughes (HHH) in May, Ackman has returned as executive chairman of the board. He invested $900 million for 9 million shares, securing a 46.9% economic stake and 40% voting control.
Ackman plans to transform Howard Hughes into a diversified holding company similar to Berkshire Hathaway, with intentions to develop an insurance business. The company’s core operations appear undervalued; management estimates the net asset value of its properties at around $5.8 billion per share, while its market cap is just $4 billion.
Howard Hughes generates solid cash flow from selling land to builders and rental income from its commercial properties. Its strategy of controlling land allows for efficient capital spending, positioning the company for future investments.
However, this new structure does carry some costs. Howard Hughes will owe Pershing Square $3.75 million quarterly, plus a 0.375% incentive fee for increasing the company’s value above inflation. Despite this, the partnership provides average investors a unique opportunity to invest alongside Ackman in potential private deals.
The views and opinions expressed in this article are those of the author and do not necessarily reflect the official policy or position of Censational Market.
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