Money

Ackman Building Berkshire 2.0 Through Howard Hughes Insurance Transformation

All-In Podcast · Bill Ackman: Investment Strategy, What the Market is Missing, How AI Breaks Businesses · June 3, 2026

All-In Podcast

Bill Ackman: Investment Strategy, What the Market is Missing, How AI Breaks Businesses

"We're going to build this into a compounding machine over the next 50 years. The goal is to build it into a trillion-dollar thing over time, compounding."

Bill Ackman revealed his strategy to transform Howard Hughes Corporation into a Berkshire Hathaway-style insurance conglomerate by redirecting real estate cash flows into insurance operations. Trading at a 40% discount to liquidation value, he plans to replicate Buffett's model of using insurance float to invest in common stocks while building a 50-year compounding machine from a $4 billion starting point.

About this episode

Legendary activist investor and Pershing Square CEO Bill Ackman joined the All In podcast for a wide-ranging discussion covering his evolution from aggressive activist to long-term compounder, his views on AI disruption, and his ambitious plan to build a Berkshire Hathaway successor. Ackman revealed he believes OpenAI's CFO should replace Sam Altman as CEO, arguing she demonstrated stronger leadership qualities and that Altman would be more effective as chairman. On markets, Ackman made the striking claim that established tech giants like Amazon, Meta, and Microsoft are massively undervalued as capital chases AI infrastructure plays, drawing parallels to Berkshire Hathaway's historic low valuations during the 2000 bubble. He disclosed investing in SpaceX at Ron Baron's urging and predicted a potential IPO at $750 billion would represent the lowest cost of equity capital in history. The conversation's centerpiece was Ackman's plan to transform Howard Hughes Corporation from a real estate developer into an insurance conglomerate modeled on Buffett's playbook, redirecting all real estate cash flows into insurance operations with a stated goal of reaching trillion-dollar scale over 50 years. Ackman also revealed his viral March 2020 CNBC shutdown call was specifically designed to reach President Trump, not just share market views. Throughout, he emphasized the critical importance of founder-led companies in navigating AI disruption, arguing professional CEOs face career risk that prevents radical pivots while founders have the authority and incentive to make transformative decisions.

Key takeaways

Ackman stated OpenAI's CFO should be CEO instead of Sam Altman, who he believes would be more effective as chairman.
He claims Amazon, Meta, and Microsoft are drastically undervalued as capital flows to AI chips and semiconductors in pattern similar to 2000 bubble dynamics.
Ackman is transforming Howard Hughes Corporation into Berkshire 2.0 by redirecting real estate cash into insurance with goal of trillion-dollar scale over 50 years.
He revealed his March 2020 CNBC appearance was specifically designed as direct appeal to President Trump to implement national COVID shutdown.
Ackman predicted SpaceX IPO at $750 billion would represent lowest cost of equity capital transaction in world history.
He emphasized founder-led companies have structural advantage in AI era because professional CEOs are incentivized to avoid career-ending mistakes rather than make radical pivots.
Ackman disclosed he invested in SpaceX through Ron Baron's recommendation and now holds positions in X, XAI, and SpaceX via SPVs.