Warren Buffett's Investment Power — or Donald Trump's Control of a Room: Bill Ackman Picks Which He Would Rather Have

Legendary investor Bill Ackman has long admired Warren Buffett, enough that he wants to copy his conglomerate investment style. But when asked a “Would You Rather” question about Buffett, the answer may be surprising.

Warren Buffett vs. Donald Trump

Ackman recently appeared on the "Katie Miller Podcast" where he answered questions about college, artificial intelligence and social media.

During a round of “Would You Rather,” Ackman was caught by surprise with one of the questions.

"Would you rather have Warren Buffett’s investment instincts or Donald Trump’s ability to control a room?" host Katie Miller asked.

Ackman’s initial immediate response was "both."

When pushed to pick one, Ackman made his pick.

"Commanding a room is very important."

In that sense, Ackman appears more interested in commanding a room like President Trump than in possessing Buffett’s investment instincts.

During another rapid-fire question, Ackman said that Trump is the most famous contact in his phone.

Investing like Buffett

Ackman has admitted to having a strong relationship with Trump in recent months, despite not always agreeing with everything he does.

When it comes to Buffett, the admiration goes back decades, which could make Ackman’s answer a surprising one.

With Pershing Square, Ackman is attempting to copy the investing success of Berkshire Hathaway (NYSE:BRK)(NYSE:BRK), specifically with Howard Hughes Holdings (NYSE:HHH).

Ackman wants to turn the real estate company into a Berkshire-like conglomerate.

“We’re going to operate much the same way Buffett did,” Ackman said on “The Knowledge Podcast” in September 2026.

Pershing has acquired around 47% of the company and is currently working on selling off real estate each year and diversifying into insurance.

Ackman compared the early days of Buffett buying into the textile company Berkshire Hathaway and then exiting that business to turn the company into an insurance company and eventually a conglomerate.

“We’re transforming it into what we call a modern Berkshire Hathaway.”

Taking a page from Buffett, Ackman is making Howard Hughes Holdings an insurance owner.

Ackman said Buffett ran an insurance operation, taking the float generated between premiums collected and claims paid out, investing it in short-term treasuries to pay claims, and investing the remaining balance in the common stock of other companies such as Coca-Cola. This helped Berkshire make a profit on the underwriting side of insurance and earn attractive returns on assets like common stock.

Photo created by Midjourney, Dall-E