Two days after Warren Buffett announced his retirement as CEO of Berkshire Hathaway in early May, outspoken investor Bill Ackman started his rival program.

As investors are still dealing with the future of the world's most valuable financial companies, no 94-year-old architect touts his plan: Change Howard Hughes Holdings, an American property asset assembled by billionaire industrialists hidden in Berkshire's "diversified debt company."

Ackman initially proposed four months of effort in a letter to investors to start a deal to start his efforts.

"Howard Hughes will become the modern Berkshire Hathaway in the case of apologizing to Mr. Buffett, which will gain control of the operating company," Ackerman said in the letter.

According to a deal with a company with a $4.2 billion market value in Texas, Ackman and his investment team in Pershing Square will change Howard Hughes’ strategy to focus on using cash to buy stakes in the company.

However, the hard-working hedge fund manager faces a long chance to achieve high-temperature financial engineering behavior.

His vehicles had to deal with high capital costs and challenges involving real estate empires, and once the competitors were called "shitco" cost-making machines, all without the advantages of Buffett maximizing such as cheap financing costs and companies willing to sell to him.

Ackman has been supporting Howard Hughes for 15 years. But the new deal involves his Pershing Square company investing $900 million in additional cash into real estate developers that own suburban communities in places like Nevada, Texas and Maryland.

The deal was concluded in early May, holding Howard Hughes of Pershing Square to 47%.

But the outspoken hedge fund billionaire – who was part of Donald Trump’s cheerleader when he won the U.S. presidency last year, his investors are already in the water on new bets.

Ackman used cash raised from outside investors to pay $100 per share last year to buy Howard Hughes shares. But investors have been lukewarm in trading. Howard Hughes shares have risen, the deal has been announced at about 6% to $71, while slightly above the S&P 500 but still below the purchase price.

Buffett will skillfully raise funds by once a Massachusetts textile manufacturer, using beautiful investments in insurance companies to turn it into a financial royal family. Ackman is now trying to achieve a similar feat and has made plans for nearly two decades.

Ackman fell into more than 20% of general growth in bankruptcy in 2008, a bet that put him in over $1.5 billion when the crisis cash crunch proved temporary.

With the general growth of bankruptcy, Ackman set up an agreement to demolish the once scattered residential land plots to form Howard Hughes. He became the largest shareholder.

A residential development (commonly known as a "master-planned community") is a mini suburban empire with housing, shops, offices and entertainment activities. They have schools, churches and golf courses, with quiet names like "woodland", which provide opportunities to live in privately run communities.

Ackman's cash will initially be used for assembly investments and build an insurance company like Berkshire, which will fuel a stable premium for policyholders.

Ackerman told the Financial Times that referring to Berkshire's earliest iteration, unlike the state of the textile industry in the United States in 1965, building cities in places where people live is actually an amazing business. ”

The billionaire financier has a different record of betting on past M&A matches.

Although Ackman bets on the merger of Burger King and Tim Hortons, he also lost billions of dollars in support of the plan to support Valeant Pharmaceuticals to become a tax-promoted pharmaceutical industry. In the 1990s, Ackman also suffered huge losses on his bets, accumulating assets through the Truct Trust First Union. The loss led to the death of his first fund Gotham partner.

Ackman maintained his courage and the first union investment, a very different pursuit made a few years ago and had nothing to do with Howard Hughes's plan.

Meanwhile, Howard Hughes itself has stagnated as a public company over the past decade.

“This is not the business that Wall Street allocates for the right value,” Ackerman said. “We are a low-investment-grade company today, and stock investors allocate high capital costs.” This recipe makes buying currencies expensive.

He predicts that the cash injection in Pershing Square will improve Howard Hughes’ credit rating by creating portfolios, resulting in earnings that grow over time and independently from the real estate market.

When Ackman served as Howard Hughes’ chair from 2010 to 2024, it bets boldly in New York City, burning shareholders’ estimated price of about $1 billion to change the historic South Street Harbour of Lower Manhattan.

Ackerman said the effort involved huge spending on entertainment and dining omelets that failed to generate substantial profits, which was probably "our biggest disappointment."

“It’s all on Ackman in terms of the value disruption of the harbor,” said a large Howard Hughes shareholder. “I don’t think there is any evidence that Ackman did a great job for Howard Hughes.”

Ackerman will also introduce a charging structure to Howard Hughes, which unlike Berkshire, does not charge any administrative or incentive fees. Pershing Square will charge an annual management fee of 15mm, with earnings of 1.5% per share higher than inflation.

Howard Hughes made savvy acquisitions under his watch, such as a deal to buy partners in his community, while Pershing Square costs less than his other funds, Ackerman said.

Some investors see Ackerman’s vision for Howard Hughes as a boon for the business.

"The deal essentially improved Howard Hughes' credit profile," said James Elbaor, founder of hedge fund Marlton, an investor with Howard Hughes and Ackman's hedge fund, who added that Ackman "paid the appropriate price" and that the fee arrangements were "fair to Howard Hughes' shareholders," he added.

The early steps of Ackman's broader plan are economically dangerous times, with global markets volatile in amid the global markets triggered by Trump's trade and tariff policies.

Ackerman thinks it's an opportunity.

"I think our timing couldn't be better," he said. "The best time to deploy capital and buy a company... is at times of volatility and uncertainty. That's when cash is most valuable."

Ackman disputes Howard Hughes's obstacles are more than Berkshire's. "We're very good at starting positions with Berkshire in the 1960s," he said. "It's an opposite of the disadvantage."